Oh, by the way, before we get into this episode, I would love to tell you a little bit about Life Notes. Now, Life Notes is a weekly-ish email that I send completely for free to my subscribers, and it contains my notes from life. So notes from books that I've read, podcasts I'm listening to, conversations I'm having, and experiences I'm having in work and in life. And around once a week, I write these up and share them in an email with my subscribers. So if you would like to get an email from me that contains the stuff that I'm learning, almost in real time as I'm learning it, you might like to subscribe. There is a link down in the show notes or in the video description.
I need to save so much money that I don't have to work a job I hate. Work is not fun. I don't like working. So if I don't like working, what am I going to do for the rest of my life? I just got laid off.
I feel like there's a lot of people in this situation. What if we put together a conference where a bunch of laid off people could all share ideas? So I ended up saying, well, I'm not going to get a job, so I might as well see what happens. I got the chance to go do venture capital, which I think was the most fascinating job ever. I just get to go see what people are building, listen, understand, invest in things that I believed in and watch them evolve and grow. And that was amazing.
So I think my outlook on money is I don't want to spend it if I can avoid it, but I do want to have great experiences. I think that's like the whole theme of my life is trying to find ways to upgrade your life, your money, your travel, everything while spending less and saving more.
This season is once again being sponsored very kindly by Trading212. Now, people ask me all the time for investment advice because they see that I've made money and I've made videos talking about where I'm investing that money. The thing that Warren Buffett and basically everyone who's sensible in the space recommends, which is to invest in broad stock market index funds, which you can do completely for free using Trading212.
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This episode is very excitingly brought to you by Huel. I've been a paying customer of Huel since 2017, since my fifth year of medical school. And it's absolutely fantastic for those occasions when you need a meal, but you don't have the time to necessarily cook for yourself. Now, these are some of my favorite product that Huel offers. This is the Ready to Drink
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This episode is sponsored by Kajabi, and they've actually got something really valuable for all of our deep dive listeners. Now, if you haven't heard of Kajabi, it's basically a platform that helps creators diversify their revenue with courses and membership sites and communities and podcasts and coaching tools. So it's one of the best places for creators and entrepreneurs to build a sustainable business. We started using Kajabi earlier this year, and as soon as we started using it, we were like, oh my God, why haven't we been using this product for the last three years? It's got everything you'd possibly need for running an online course or hosting an online community or building an online coaching business.
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Chris, thank you so much for coming on. Thanks for having me. We're meeting in real life for the first time because you're here in London. I know, we talked about doing this and I was like, well, I probably won't make it to London. And then I was like, hey, I'm coming to London. And we're recording this at like 10pm. Yes. So this is going to be super fun. I'd love to get started with, so you've got this podcast, All The Hacks, which I discovered because you interviewed Tim Ferriss on Tim Ferriss' podcast about growing a podcast. And I listened to that episode. I was like,
hey, that's really cool that all the tips about growing a podcast. But then I was like, who the hell is this guy? Like, how did he interview Tim Ferriss about growing a podcast on Tim Ferriss' podcast? And then you managed to randomly email me like some weeks after I listened to that. I was like, oh, I know this guy. And so that's how we kind of got connected. But I guess if we rewind the clock, like, how did we get here? How did you come to be in this place where you're recording podcasts about hacks?
hacks and stuff and being friends with people like Tim Ferriss? And how did we end up just kind of talking here? It's so interesting. My whole life, I've always kind of been that person that's like, ah, maybe there's another way to do this. Maybe there's another way to get a deal. I've always been a fan of optimizing everything, like everything.
in high school, I wanted to order, I went to boarding school and I really wanted to like get pizza like everyone else did at night. Everyone would order a pizza for delivery, but my parents didn't give me like an unlimited budget in their credit card. So I would order pizza, I would sell seven slices and I would get one for myself and I'd make a little profit. If I was hungry, I'd sell six and eat two. And so, you know, I was kind of like trying to find a way to get the experience that I wanted without having to spend the money.
And that was really like, I had those little things. I never knew it was going to be a real thing. And then after college, I got a job in investment banking.
Not because I wanted to be an investment banker, but because I didn't know what I wanted to do. And everyone said investment banking is the best job. And I was like, well, I don't have time to figure out what I want to do. So I'm going to do the thing everyone told me was the best job. And I was like, oh, this job is not for me. It's not the kind of job that entrepreneurs enjoy. And so then I went to management consulting, which I thought maybe would be better. And it was kind of the same thing. And I was like, gosh, work is not fun. I don't like working. So if I don't like working...
what am I going to do for the rest of my life? Well, I need to save as much money as possible, like fire financial independence style without really knowing what that was. But it's just like, I need to save so much money that I don't have to work a job I hate. And that took me down this path of, okay, well, I don't want to live a crappy life. So let's find a way to do everything I want to do. Like, let's go through, okay, I like to travel. Okay, I want to live. Okay, how do I house hack? Oh, how do I do these things? Just trying to find a way to make that work. Eventually, I found jobs I liked and
But I was still so far down the optimization train that it just became a thing I love doing. Damn. Okay, cool. Okay, so let's, I want to kind of take us back to the beginning, I guess. So what did you study in college and how did that lead you into the investment banking route?
So I went to Colorado State University, not a highly ranked university in the States. And honestly, I went because this girl I was dating was going to go there. And I was like, let's go there. I thought maybe I would have a better outcome going to a worse school and standing out than going to like a tier one school and just being one of a bunch of people.
I think that ended up being true, but my parents were not happy. They were like, why didn't you want to go to some Ivy League school? I was like, eh, this seems great. We broke up right away. So a little bit of I told you so, but it worked out. And I was like, well, I want to start a company. I want to be an entrepreneur. I'm going to get a business degree.
And then I looked at the majors that we had and it was like, well, IT, finance, marketing, management. And there was one other, I can't remember. And I was like, well, if I run a company, I'll probably hire someone to do them. And accounting. I was like, I'll probably hire someone to do finance and accounting. Marketing, finance.
seems, I don't know, I'll do marketing. Like I was just, I didn't know what to do. I was like, management seems like a skill that you kind of just either have or you don't. I didn't know what I was talking about. So I did marketing. And then I took a bunch of other things like French and, you know, entrepreneurship and math, but yeah,
I went home over Thanksgiving, which, you know, it's like maybe five months before graduation. And all my friends who went to these Ivy League schools had jobs. And I was like, wait, you have a job? Like my school had not prepared anyone for a job yet because most people weren't going to the kinds of jobs you need to plan six months in advance for.
So I was like, what are you guys doing? And they're like, oh, the best job is investment banking management consulting. And I just went back to school and I went to the dean's office in the college of business. And I went and I said, I need your help to get a job in investment banking and management consulting.
And somehow the dean of the College of Business knew one guy that worked at an investment bank and one guy that worked at a management consulting firm. Great. Gave me interviews. I missed the deadline. So one of them offered me an internship and one of them offered me a job nine months after graduation. So I took both and I thought, I have a backup plan. So I did one, didn't like it. Did the other, didn't like it. Damn. Yeah, so it's...
I guess basically everyone I know who did a non-medical degree went down the either investment banking or management consulting route. And actually a lot of people I know who do have medical degrees are now trying to go down those routes because they're like, oh, this is my exit strategy for medicine. They do medicine for a bit. They realize they don't like it. And then they're seeing, oh, there's a lot of money over there. There's a lot of money with those people with their fancy suits and stuff. What was investment banking like for you?
Investment banking. Imagine I have no idea what investment banking is because I actually don't really know what an investment banking is. I didn't know what it was either. I was getting this job and I was like, well, I got to go buy a book about what is investment banking. And I was like, do I work in a bank? So basically, you're supporting people. At my level, four tiers down from the person actually doing the job, I'm making space.
Okay. And the whole idea was an investment bank works with companies and either helps them go public or acquire companies or get acquired and kind of strategic financial transactions like that. So my job was like, let's go. Some company wants to get acquired. They want to... Or some company...
Someone wants to go buy a company in a space and they're like, what should we pay for this company? Let's go look at all the private transactions that have happened in the space and let's try to get an idea of what the valuations were relative to their revenues or relative to their profit. And what are all the public companies in the space valued at on these metrics? Let's come up with an idea of what's a fair price.
At the end of the day, you're really just trying to come up with a way to justify the price that you agreed on because it's a negotiation. So it seemed like a little bit of show. But sometimes it's literally like we actually need to do the show to send to our shareholders so that we show that we did diligence. Yeah. But at my level, it was like, hey, I'm going to go home. Why don't you make this spreadsheet till four in the morning? I'll be back at eight tomorrow. I hope you're back.
And I remember a week went by where I went home and my girlfriend at the time was asleep and I left before she woke up and I was like, this is horrible. Like I don't, I'm not even seeing the person I live with awake. Um, and I was like, I think I got to take this other job, which was a management consulting job. Um, which wasn't that different. Except you're, you're making PowerPoints. Yeah. Yeah.
Okay, so you were in investment banking for a few months before realizing that it wasn't for you? Yeah, so I did the internship. At the end of the internship, they offered me the full-time job. And I was like, okay, I'll take the full-time job. Because I was like, oh, I need to pay rent. So I took the full-time job up until this management consulting thing started. And I was like, hey, I'm going to leave. I'm going to take this other thing. And they were kind of like, okay. Like they weren't upset. I kind of was in this weird spot where they didn't offer me like...
They kind of said stay on as a full-time intern instead of here's a full-time offer where you're going to get a bonus and you're getting all this stuff. They were kind of like, well, we want to keep you. So as soon as there's an opening, we'll give you a real job. Until then, you can be a full-time intern. We're going to pay you a little bit more.
But it wasn't clear that I had a full-time job. It was kind of a weird spot. And so when the consulting job was ready to start, I was like, thank you. This is a great experience. I learned a lot. Let's see what that's like. Nice. Okay. So you've done your stint in investment banking. Did that teach you anything other than the fact that you didn't like investment banking? I mean, I think you just learn how to grind through anything. You know, I think there are some jobs where...
Especially now I meet people who are like, oh, you know, I'm just kind of cruising, having fun. I'm living in a van. Like this was, you were working sometimes 22 hours in a day. And you just have to like grind through things. And you're working with very, very smart people. Even just the interview process. Like absolutely.
If I never even took the jobs, having to go through these interview processes where they're asking you to do these complicated case studies and like one time it was with a team. And so I was interviewing with other people who were interviewing together working on a project and then asked to give feedback on the people I was interviewing with.
So I think I just learned a lot being surrounded by really smart people. And that was fun. But at the end of the day, I think the problem I had with both of those jobs was that it was very hierarchical. It was like there was a moment in management consulting where we were trying to close a deal as a firm with, you know, like a Fortune 500 company. And I obviously wasn't the one selling the deal. That was like the managing director. And I was this low level, you know, first year. But a friend of mine had a deal.
I happened to have the CEO of that company was his stepmom. And I was going to hang out at his birthday party and she was there. And I remember asking the managing director, I was like, hey, I'm actually going to go to the CEO of this company that we want to win business from. I'm going to be at her house this weekend. Do you want me to talk to her about this? And he's like, no, that's not your job. And I'm like, I know that's not my job, but it seems like there probably could at least be a conversation worth having here. And it was like, no, that's not your job. And I was just like, it feels...
And maybe I was too full of myself, but it felt a little irresponsible for the company to not entertain whether it was a good idea. So it just didn't seem right. And then at the end of the day, everything in my kind of life trajectory changed when I went to this event called Startup Weekend, which was...
A guy in Boulder started this thing where he got a bunch of people together, engineers, designers, product people, just business people for a weekend. And you all broke into groups and built companies. And I drove up to Boston from New York City and we built this company. It was silly. It was called Desk Happy. It was a Windows app that every like some random number of time, like 45 to 90 minutes, it would pop up a thing and it would give you an exercise. Like a
A five minute exercise, like stretch or, you know, you know that thing where like the Apple Watch will buzz and tell you to do something. It was that for Windows, but like a decade ago. And I was like, oh my God, we built a company in a weekend. Nobody downloaded the app. Like it never went anywhere. But I was like, I want to do this. Like, this is amazing. And everyone's like, well, you should probably live in San Francisco. Like everyone in San Francisco is building tech companies. And I was like, I will do that.
So I immediately put in a request. I said, hey, could I move to San Francisco? I'd really like to work in the San Francisco office. They said, sure. I was like, wow, that was so easy. And then like a week into working in San Francisco, I got this call to go to a meeting with a guy I'd never met. And I was like, wow, this senior person wants to meet with me. This is cool. And he was like, you're fired. Oh, this was a management consulting thing. Yeah, yeah. So it was 2008, middle of the financial crisis. I had thought, you know, they kind of were like, oh, you're this person that just transferred offices.
you've got nothing on your plate. You're a great person to let go. So I was fortunately, uh, you know, given an opportunity to go do something else. And I think at the time I was kind of disappointed, but in the long run, I think it, it was a huge impact because it forced me to go find something else to do.
Yeah. Okay. So at this point it's 2008. You're probably like mid twenties. How old are you at this point? 2008. I'm like 24. 24. Okay. And 26. You've just moved to San Francisco where presumably rents are quite high and you've just been fired from your job. Like how does, how does that feel at that time? Yeah. I'm not good at math because it was actually 22. Oh wow. Okay. Um, no, no, it really sucked. Uh, I got laid off in November. So I was like, oh man, the holidays around the corner. No one's going to hire anyone in the U S between Thanksgiving and Christmas at the end of the year. So I was like, what am I going to do?
And so I actually had no idea what I was going to do. Fortunately, my girlfriend, who's now my wife, had a job. So we were like, okay, great. She had flown out to San Francisco a month early, found a job. And maybe two weeks before I got laid off, she got a job. So it's like, we at least know how to pay the rent. And I really didn't have a clue what to do, except that I had gone to this weird event called Bar Camp.
which is kind of like this tech conference, but it's not really about tech. It's kind of about life. And it was an unconference where people just threw up ideas of what they wanted to talk about. And it was, you know, it was just like a fun place to be. And I was like, well, this is really interesting. I just got laid off.
I feel like there's a lot of people in this situation. What if we put together a conference where a bunch of laid off people could all share ideas and you could bring entrepreneurs, you could bring freelancers, people could learn skills. Like maybe I have a skill I could freelance. Maybe someone wants to start a company and I could do that with them. So I ended up saying, well, I'm not going to get a job. So I might as well see what happens. And so I made this thing called laid off camp.
And I can't even remember where I posted it. I posted it somewhere on the internet. Nobody really found out about it at all. But it was just in the zeitgeist enough that TechCrunch wrote an article about it. Oh, wow. Okay. And at the time, I thought it was fake because this woman emailed me and she was like, I'd love to write a story about this. I found it somewhere. I work at TechCrunch. I was like, oh, I felt like I was on top of the world. I called a friend of mine. I was like, I just did this interview with TechCrunch. And
And he was like, who was the reporter? And I told him her name. He's like, I work with TechCrunch a lot. I don't think that person works there. And I was like, oh. And it turns out the woman who wrote the – that was the first article she'd ever written at TechCrunch. So nobody actually knew she really worked there. But that kind of caught Silicon Valley kind of central zeitgeist around the –
recession at the time, you know, it got picked up in the San Francisco Chronicle. And by the time we did the first event in San Francisco, we had NPR there, we had the Wall Street Journal there, we had the New York Times there, CNN. And, you know, it was really like a big thing. I didn't make any money. It wasn't a for profit enterprise. I open sourced the whole thing on a wiki and let people run 20 or so other laid off camps around the country. But it
It was a great opportunity to like test those entrepreneurial muscles, meet a bunch of interesting people and kind of see what a new world might look like for me.
So what happened at Ladoff Camp? Like, what was the story there? Yeah, I mean, I never knew. It's funny, someone asked me a few days ago, they're like, maybe you should start this back up again. Sounds pretty good, yeah. No, nothing really happened. It kind of fizzled out. The recession kind of stopped being a thing people were talking about. We'd done one in almost every city in the country that was a major metro area. And I said, okay, I need to find a job.
I had met a couple companies through this process that had hired me to do random freelance things. One startup was like, well, you could have worked in a investment bank. Maybe you can help us build the models we need to go raise a late stage round of financing. It's like, great, I'll do that. I need money. Another company was like, well, you put on all these events. We want to start putting on events in the community as part of our business strategy. Will you help us throw events? Great, I'll do that.
So I did a few freelance jobs and I decided I wanted to find a job at a company. But before I do, all my freelance jobs are coming to an end. My wife hated her job. I think still girlfriend at the time, but really hated her job. It was pretty terrible. She was like, I got to find something new. And I was like, gosh, well, my freelance things are over. You hate your job. Maybe we should take one trip. And like, we have a little bit of savings, not much. We'll take one trip. And then after that, we'll hit it hard. You'll find a new job. I'll find a new job. We kind of have a better sense of what we want.
One thing led to another. We rented out our place furnished for more money than we were paying in rent. So we're actually making money because it looked, it turns out the Delta between like a furnished apartment that you can rent for a month or two and like apartment you have for a year unfurnished is actually a margin, you know, profit margin business. And we bought a one way ticket with points to South Africa and we just backpacked for seven months.
The goal was to get from South Africa to Singapore by land. There were a few borders we couldn't cross and we had to fly. But...
Yeah, that was not what we intended. Like, you know, I was gung-ho, ready to work in tech, ready to get back into it. But it just seemed like an opportunity we couldn't miss up. And we put this whole map on the wall. We were like, let's put pins on countries we think would be cool to see. And we're like, that's a lot of countries. How are we ever going to, you know, the average person takes a trip like I'm on now. You go to London and Paris for a week and a half. It's like, how am I going to see 40 countries around the world if every year we can go to one or two of them?
And then I'd read this book, Vagabonding. Oh yeah. And, uh, Rolf Potts is awesome. I got a chance to interview him on my podcast. And, um,
I was like, maybe we could just do this long-term travel thing. And it's so much cheaper because you're taking buses and trains and couch surfing instead of flights and staying in hotels. And so we did this whole trip on like $7,000 for seven months, which still seems crazy to me. About $1,000 a month, about $30 a day. And it was like one of the most amazing life-changing experiences ever.
And then I submitted a talk to talk about all these things at South by Southwest and it got approved. And they were like, we want you to come speak in March. And I was like, well, now I know when the trip ends. So, you know, in November or something, we booked a one-way ticket from Singapore to Austin to go to South by Southwest. And, you know, that was the transition to the next chapter of my life. Yeah.
So much to talk about. So, yeah, ever since I read Vagabonding, I think an episode of the Tim Ferriss show probably turned me on to it. And then started listening to Rolf Potts' podcast as well. It was always in my mind as a thing that it would be really cool to do.
But I was always in this traditional job. And so in 2020, when I took a break from medicine, I was like, right, this is going to be my chance to do my little vagabonding trip. But then pandemic and everything closed. And so I've not yet done my vagabonding trip. But I'm trying to talk my girlfriend into it at some point where we'll do the traveling around the world for a year somewhat later.
aimlessly kind of thing. The sooner you do it, the better. Yeah. Because what I've learned is my standards have risen over time. And, you know, we stayed at a hotel in India that I think was $1 a night. I don't think that I could, like, I don't, I want to say that I could go do it again, but I feel like I've gotten old enough. We have two kids, like, what am I going to put my kids in a room that like barely has running water. The windows are just holes in concrete walls. Um,
Probably not. So the younger you do it, the sooner you do it, the more comfortable with the grit and the grime, the more you can take a trip that I just think as a trip you can't replicate. You can't replicate staying in some $2 a night hostel down an alley when you have a family, if that's in the cards. Yeah, I've heard that this is very much a thing that you kind of are able to do in your 20s and then not really beyond that.
And it's almost like... I think I was reading Die With Zero that talks about this and a few other things that talk about how...
It's not just when you're old and like you've got illnesses and stuff or like families and stuff where you can't take trips like that. It's actually just when you don't want to do that anymore because going around hostels and stuff at the age of 19 is very different to the age of 31, for example. Yeah, it's funny. I interviewed Bill Perkins who wrote Die With Zero and I said, you know, do you have any regrets of things that you didn't do? And his one was I didn't take a gap year. I didn't go explore when I was younger. And now it's just a different experience I would have.
And that's not to say, you know, I got an email from one of my listeners who has a family and they've been living nomadically for years. So it's not to say you can't travel with kids, you can't travel with a family. I just think there's a certain type of travel where you're like, I don't know where I'm going to go to tomorrow. And I'm just going to wander around until I found a place to sleep. And I remember doing that in Zanzibar off the coast of Tanzania, or I guess it's in Tanzania. And we were just like, for three hours, we were trying to find a place to stay.
because we didn't have a plan and we went into a hotel. Things were fully booked. Finally, we found something. But you just can't do that with kids. Like you can't. Maybe at some age, but our kids are two under three. It's just not going to work. So there are some elements of a trip that you could do at any age, but there are some that I would highly advise you to do before you start a family if that's something you want to do.
Often on hearing that kind of advice, some people would be like, oh, but what about the gap in the resume? What about like the dot dot dot? How would you approach that kind of fear? It's funny. I applied for a job once and the guy that reviewed my resume was like, oh, you've changed jobs too much. And I was trying to explain. I was like, well, no, actually, I had this investment banking internship and like it wasn't supposed to be forever. And then I did this management consultant and then I got laid off. It wasn't my fault. Like, it's not like I'm a flaky person. It's just I had these series of things and he was kind of very rigid in the way he thought about it.
And I was like, well, I guess my answer to you would be that person is probably going to wonder what's happening. I think for every one person like that, there's probably 25 or 30 people who are going to be impressed that you took that trip, want to know what it taught you, you know, jealous that they didn't take it themselves. And so...
I don't think there are very many people who would look at a year off and judge you or hold you against getting a job because of it. So I don't know. I would tell someone that obviously you might spend money and be broke. That's like an important thing. So make sure you have the savings to do it or go on one of those trips where you work on a farm. There's lots of ways to do it. But I wouldn't let taking a year off and the impact it would have on your resume stop you from doing it. And I don't think very many people...
who've lived long enough to reflect on that or are older would say that. In fact, I don't think I've made a resume for a while. I don't know if you have a resume that's current. Like I have a LinkedIn page, which kind of is enough. Yeah. A lot of people say that when they do a sort of extended travel thing, that it changes them, it teaches them a lot. Having not done one of these trips,
I almost can't imagine what it would be like. I guess, what did you learn on that trip? How did it change your outlook? How did it change your life? I think there are a few small things that happened that maybe had big impacts. But I didn't have one of these like eat, pray, love moments where I was like, I left and I was a changed human and all these things. You know, you kind of got to the end and you're like, oh, okay. Like, there wasn't that moment for me. But there were a few things that I think were important. One was...
When you travel, especially when you travel outside of, if you live in the States and you come to London, it's not going to be as different as if you go live in Southeast Asia or you trek through Africa or you go to South America or a place that's kind of a very different way of living. And I think what I learned that was super fascinating was that all around the world, people have found ways to be happy and they found very, very different ways to be happy. And I think the thing that has led me down this like intense optimization part of life
is not believing that any particular way of doing something is just by default the right way.
So there's a way that most people do things and just because the people you're surrounded with say, "Oh, well, you know, this is what you do. You go to a job and you don't take a year off." Well, in the UK, I feel like almost everyone takes a gap year after college. But in the US, maybe that would be frowned upon because most people don't do that. So I think the biggest lesson I took away was there are people that have wildly different days. The structure of their days, the way they work, the way their family works, the way their family lives.
and it all just works for them. So it made me question, maybe to a level that many of my bosses, managers, friends don't like. It's like anything we do, there could be a better way to do it. So someone says, oh, let's do this. I'm like, well, is there a better restaurant to go to? Is there a better way to get there? Is there a better deal to be found? I think that's one of my biggest takeaways. And then
I think from a material possession standpoint, I feel like there's an inverse relationship between just general happiness. Like the people who I met that had the least seemed the most content with life. And the people that I met that had the most seemed the least content with life. And so not to say that I don't have things and, you know, I'm not a minimalist by any stretch of it, but it's just like, it's very easy to be happy.
Just running around in a field and like kicking a soccer ball or even like something that is a bag, a bunch of trash bags balled together to resemble a soccer ball. So I don't know. Those are two important lessons, but I didn't have a,
I knew what I wanted. I thought I'd come back and I'd be like, I know what to do with my life. No, none of that. It's a broadly pretty fun trip, $30 a day, like trying to get from South Africa to Singapore. Yes. Where do you have to fly? Like what were the borders that you can... So we couldn't get over the border to Sudan. Oh, yeah. And so that was a tough one. Iraq, Iran, Afghanistan. Yeah. And...
Burma, Myanmar was one where you could go, but you could only fly in. And so in each of those three areas, we ended up flying over. So we flew from India to Thailand. We flew from like the Middle East over to India. And then we flew over Sudan. Were you concerned about your safety at any point during this trip? That's another thing that often seems to come up.
Not really. I think there was like one point where I think we're in the middle of a really busy market in the evening. And I was trying to figure out where to go. And I had the map on a PDF on my computer. It was like this cheap $200 mini PC, this Dell computer. And I remember opening up my laptop. My wife was like, you probably shouldn't just open a laptop in the middle of the street here. So maybe that moment. But there really wasn't a moment where it was like, wow, I feel...
you know, very scared right now. There are moments where we're like, I don't know what to do. We get to a bus station, there's no bus and there's no place to stay. And it's like, okay, well, let's go to the only store that's open and ask everyone that comes into the store if they're driving. This is in Malaysia. So we're just like, are you going to Kuala Lumpur? Nope. Are you going to Kuala Lumpur? And we just kept asking until someone was like, no, but like,
This other guy I know is, let me give you a ride to this semi truck where he's going there. And then we just like get in a semi truck with some guy who says he's going to Kuala Lumpur. And like, you know, we're just like hanging out in his car and he was listening to Britney Spears, but he didn't speak English. So it was like this amazing moment of someone like singing to American music, but not really actually speaking English. Yeah.
Went through a border crossing and he closed the curtain in the little area behind in the bed of the truck where we were hiding. I was like, are we being smuggled through? So I would say that was maybe a moment where we were a little nervous. But I think by that point, we'd already had four months of just serendipity, making things better. They were like, I don't know, we haven't hitchhiked a lot. So this will be a great story. Let's give it a go.
Okay, so I definitely want to talk more about the kid stuff and the optimization stuff. Before we do that, so you finished your seven months of traveling, you're at South by Southwest. What did you talk about in the talk? So the talk I submitted was like a fun, I think it was called like fun employment. And I invited a friend who'd never been laid off to like co do it with me as a panel just because we were both trying to optimize for,
getting a talk. And he was like, well, what you could talk about is more in the zeitgeist. And I was like, well, you work at a company that's like a really hot, cool company right now. So like the combo of that surely will be approved as a talk at South By. And sure enough, it was. That South By was really interesting because...
It was this weird opportunity to just go meet all these people in this industry that I wanted to get into. So the talk was rather, you know, it was like, what does it mean to be unemployed? How can you make the most of it? It was kind of one of these, if you're trying to understand the world of getting laid off and figuring out what to do with it, come to this talk. So I wouldn't say the talk was anything, like if there was a recording of it, I would not recommend you go watch it.
But that entire experience of immersing yourself in a new community of people and trying to figure out what you want to do in that community was a very profound moment in my career. And it was back when South by Southwest was a small conference that not a lot of tech people went to. And over the next 10 years, it kind of totally went the other end.
It's a wonderful deal. Because the only context in which I've heard about it is a four-hour workweek launch thingy. And listening to the audio of that like a few months ago and thinking, wow, that was actually a really good talk from back in 2007 or whenever it was. And also...
I think it got canceled in COVID. Like that's literally the only two data points I have about it. So what is South by Southwest? So what was it? When I first went, it was like primarily a music festival. It was like a two week music festival. Then they, I think they added film and then they added this like emerging interactive component. So it was very much known when you first went to South by, I was like, Oh, I'm going to South by Southwest. It was like, Oh, you must love music. I was like, actually, I don't really like live music. And people were confused. Um, but it was this like the internet conference, uh,
And all the early kind of internet tech people were there. Companies like Digg were throwing big parties. I remember spending a lot of time in the early days with like Gary Vaynerchuk, who was like running around, like throwing events.
So it was kind of like that early web creator-y world that didn't really have an event, and South by Southwest was the event. And I remember for probably eight years, it was like every year, there was not a conference that I missed
Southwest was like the one conference that I wouldn't miss because it was when all the people I knew, whether they lived in New York or the Bay Area, everyone would convene on Austin and there'd be, you know, all the events, the parties, everything. It was just a great place to meet all those people. And a lot of the fun stuff happened in like, you know, people's hotel rooms late at night where you're just kind of jamming on random ideas and,
The number of companies that came out of those jam sessions of people that were just like, I have an idea. Everyone's like, what's this person really doing? And it's like, oh, that was Travis Kalanick who went on to start Uber and like all this crazy stuff out of these rooms. But yeah, it was, you know, I just, it was like a very right place, right time kind of moment for me where I just kind of like entered this industry of tech in Silicon Valley and met a lot of interesting people. And I was like, this is going to be my career for the next decade. How important do you think that is
These days, like the whole finding a community, finding a senior, as Austin Kleon talks about. Is that something that you've seen like sort of beyond that point has been helpful for you or for other people that you know? I think the network of people that I got to know and built in the, you know, let's call it like broadly speaking, like the internet, you know, entrepreneur software creation community, like Silicon Valley, but like extended to the country startup world,
was like the most valuable thing towards any of the path that I took. So it was like when I wanted to get a job, you know, it was being able to have people who I'd met who'd gotten to know me and my personality and seen that I did this crazy thing with laid off camp. We're like, oh, you should take a bet on this kid. He's got a lot of like audacity to go start random stuff. That community of people was what made all these things possible.
And even today, when I'm now in a different world, a creator world, a lot of those early relationships, you know, are still really important. There's a...
different but kind of overlapping circles of like startup entrepreneurship investors and creators. And I think we've kind of, we're in like a WhatsApp group that merges those two really well. But I don't know, I'd say it's the most valuable thing that I ever did was go to South by Southwest and start to build a community of people. Now, had you done that 10 years later,
I think it would have been hard because at that point there were every brand was there sponsoring things and it was probably hard to find your community. So I would say when new emerging things are happening, new events, new conferences, like that's a really great opportunity versus, you know, like CES now is like probably not the best place. There's certainly good events and you can probably go meet interesting people, but you might have to
Go a little more niche or a little more emergent of kind of events to go find that or a little more. And by niche, I mean, it could be category. It could be like, I really want to get involved in FinTech. So I might go to a conference there. Or it could be like, I'm going to focus on people in the Bay Area or people in London or people in New York, rather than trying to go to like the big thing. But yeah, I would say find people anywhere they are and build that community. Yeah.
Yeah, I think about this a lot whenever, you know, these days it's nice because I get invited to go to conferences and I'm going to Sharjah and the UAE tomorrow to give a talk and stuff. And before going to one of these things, I'm always a bit like, oh, it's a long way to travel and it's like, woe is me, et cetera, et cetera. And then I get there and I meet the people who are there and I'm like, okay, cool, this was 100% worth it. This was super, super fun. And just the, I think the serendipity that you unlock by actually going to things where there are other people doing a thing
Like even, you know, one conversation I had with our mutual friend Erica Kohlberg like a week ago in Dubai. She and I had never met before then. We kind of talked on Instagram DMs a little bit. But that conversation might be the most ROI positive conversation I've had this year in terms of the decision we're going to make for the business. And it's just always I found a lot of times in my life connecting the dots looking backwards is always from has been from a moment of a serendipitous interaction that I could not have predicted at some sort of event where I was
put the effort into going to the thing rather than like oh i'll just sit in the hotel room i'll just like i'll just do some work and i always find that the expected value of actually putting yourself out there is stupidly high yeah the worst part is it's not always high like it's it's um
You know, the CEO of Wealthfront, a guy named Andy Ratcliffe, always talked about when you're building products, he's like, I care about the slugging average, not the batting average. And for the international folks, this is an American baseball reference, and I don't even follow American baseball. But the general idea is, it's like, how often are you hitting a home run and scoring points versus how often are you hitting the ball? And so if I go to five events, conferences, whatever it is,
I care less that I meet five interesting people. I care that at one of them, I had, like you, a meaningful conversation that will change the trajectory of my business, my personal life, or something.
And it doesn't happen every time. But I would rather have four conferences where every fourth conference changes my life or my business than have four conferences and the other three do nothing than four conferences where each one I meet an interesting person. I'm not saying I don't want to meet interesting people. Hopefully I meet an interesting person at all of them. But I'm going for those really, really big moments. And they don't happen every time.
And so it's funny when I was thinking about, you know, do I go to business school? And I was like, no, no, that's just like management consulting, investment banking 2.0. But I was talking to someone, I was like, I bet if you just bought a business class ticket from New York to San Francisco and you just flew back and forth, back and forth, back and forth and talked to the person sitting next to you.
You would probably unlock a similar amount of value as if you spent the same amount of money, you know, going to HBS. I'm sure many people listening, especially the ones who went to HBS, were like, no, no, no, no. Like, I totally disagree. But the idea being, you will probably have six or seven of those flights where nothing happens. And then every six or seven, you might have one really, really powerful, interesting conversation that leads to some crazy opportunity. The hard part
is if you have the six or seven bad ones first, continuing to go for the next one when it's not there. And so I have definitely been to conferences where it was just totally not worth it or have flown to an important meeting that didn't pan out.
It's happened enough times that it's like, I think I got to keep trying. And so I think it's a hard thing, especially if you're, you know, now we have kids. I'm like talking to my wife. I'm like, okay, I'm going to go to this conference. I really appreciate you helping out extra so I could be out of town. And then I come home and I was like, you know what? That was a waste of time. I shouldn't have gone.
But I promise that if I do this five times, one of them won't be a waste of time. But it's really hard when you have the waste of time when the opportunity cost is high and all that. But I still encourage everyone listening to go put themselves out there a little bit more and try to find that community and look for those super high ROI interactions. What do you think is the balance between
Put your head down and do the work versus go to conferences and meet people. Just to weave a somewhat false dichotomy between those two things. I mean, it depends where you are at what stage in your life. If you're working a job and you're trying to figure out how to transition somewhere, just doing the work is probably not going to have that impact. If you just started a company and you're trying to find product market fit for the business you started, going to the conference is
might be helpful to give you a new perspective, but like sometimes you just need to do the work. And so I don't think there's a real answer. I think I've definitely had moments. I remember a fun moment where a friend of mine were joking about how this one friend of ours who started a company seemed like he was way too down the conference path. And so we were like, gosh, this guy just needs to like sit at his office and work and like with his team for like two weeks straight. And
So we created this idea where we found this person who is a professor at some university who did a lot of research in Antarctica. We made up a fake email address pretending to be them and invited our friend from this email address to come to an all expense paid trip to South or to Antarctica for a conference for tech leaders.
So we went back and forth. We talked about how we were comping all of the flights. We started scheduling the flights for this person. We had it all like planned out. We even like made up fake, I think we said like Jack Dorsey's coming to this conference and all this stuff. And then finally, like maybe two weeks before we were at this bar and we were like, he was, you know, I'm so excited. I'm going to Antarctica. It's going to be so cool. And we were like, yeah. And so we finally like broke the news that we'd made this thing up. We're like, but good news. Now you have two uninterrupted weeks that you can get work done.
And I don't think he appreciated it like we thought he would. We haven't really caught up since then. Right. You know, on this topic at least. Okay, right. But yeah, I do think you can go too far down the path of like, oh, I'm going to the next thing. I'm going to the next cool thing. But it really depends where you are at the stage of your company. When I talked to other founders and CEOs when I was running one of my businesses, they
It was interesting how so many of them were like, I need to spend like half my week unscheduled just to find the right thing to work on. And I can't plan it. So in that stage, it's like, it's not just grinding. It's like...
leaving room to think and see what's next. What's the thing in your business that you're missing? What's the thing in your career, your life that you're overthinking? So I think it's important to do that, but maybe time box it. Be like, okay, there are two conferences this year. Around those two conferences, I'm going to go. I'm going to leave a couple days after to process everything. Great. But don't be looking every week for the next thing. Yeah, nice. In terms of optimizations, hacks, all that kind of stuff, any tips for conference attendees? I'd say you're at a conference, it's like...
What do you do at said conference to, I guess, make the most of it? Yeah, so here's one thing I do, which I don't know if this is crazy or not, but I always email the conference org. Some conferences just give you the list of all the attendees. Great. Most of the times that list doesn't also include the speakers. But the speakers is always the one thing that's public. And so I try to combine those two lists so that I have a list of everyone that's going.
I try to figure out who, and the funny thing is, I would say 50% of the most impactful conversations I've had at conferences are with people that I didn't even know who they were. I just randomly met them. What about 50% of them were with a very targeted set of people that were often speakers at the event or like, you know, successful people who were attending, but maybe not speaking. So I'll go through the list one by one, trying to figure out who at this conference do I want to interact with?
If they're giving a talk, I know they're probably going to be in the room that they're giving the talk. And so before or after that talk might be a good time to run into them. But I will actually go and pull like LinkedIn photos or some photo of a person. I'll put them all in a notes doc on my iPhone. And like I'm in a room and I'm in the corner. I'll pull up my phone. I'll be like looking at all the faces just to kind of like brush myself. So when I'm walking around the room, I'm like looking out for those people that I want to engage with and try to find them.
So I'm like, you know, it's kind of, I kind of feel like I'm like a mercenary in the corner. I'm like, okay, I got to go find this person with brown long hair. I'm like walking around looking for them, but I'm very tactical about it. Trying to have those conversations. I usually only end up hitting about, you know, 30, 40% of the people I wanted to find, but I do hit 30 to 40% of them. And I don't think I would if I wasn't sitting in the corner of the room every now and then running through my list, trying to be like, oh, there's that person I want to go engage with. Let's walk up. I think walking up to a random person is like one of the
things that one can do. And so one person gave me this advice. I did an episode of my podcast on kind of networking at events and asked about this. But one person was like, just practice it in low stakes environment. Go to a
Go to a bar where literally it doesn't matter who you meet and just walk up to random people and start conversations. It's probably easier than you think. And if you could do it in a low stakes environment where it doesn't even matter, maybe when you're traveling, you're never going to see these people again. You don't have any friends in common. Like if you can really build that muscle of like just walking up to someone and being like, Hey, what's going on? Um, was one. And then leaving, always being the person who leaves first. It's like everyone at this conference, especially if you're going to these speakers, um,
They do not, they probably want to leave after a few minutes. Maybe you're really exciting. Maybe you're really engaging. But, you know, so it's kind of like a power move to be like, all right, you know, I'm sure you've got lots of important stuff to do. I do too. I got to go. Not being the person that just sits there talking to them forever and trying to get them to commit to some next thing in person. It's so much harder. If you're a podcast host and you want someone to come on your podcast, you're going to have to do it.
Don't be like, "Hey, can we email later about XYZ?" Be like, "Hey, could you..." Get them to soft commit in person to whatever the next step is, whether it's grabbing a coffee, making an introduction or something. It's so hard to say no to things in person. I know. I get this all the time. Usually we have Gordon, our videographer with us, and he's like, "Ali, you've said yes to too many things. You need to start giving Dan's email, my assistant, rather than your own." All this kind of stuff. Yeah. So ask people to do whatever you want in person because people like Ali are much easier to get to commit in person. It's hard enough to say no by email. Yeah.
And they just know what they look like so you can go find them. Yeah. Do you talk to people on planes? I feel like you seem like the sort of guy that would strike up conversation, but I don't know if you do anything interesting like that, like planes, buses, coffee shops, that kind of thing. I think...
less and less. I think if I'm flying by myself and I'm sitting next to a person and it seems like maybe there's something worth having a conversation about, I'll say hi. But I wouldn't say I'm like the person who's always striking up the conversations on the plane. I think it's probably, I don't know, if I were sitting next to a random other person by myself not traveling with my family, I might end up having a conversation one in four times. But I'm not a four in four like, hey, how you doing? Yeah.
I've been I was rereading this book called The Luck Factor by Richard Wiseman. He's this like psychology professor who I had on the pod a few months ago. And this is like one of the OG self-help books that was really recent, like 2002. I first read when I was like 16 years old. And it talks about the factors that like people who say that they're lucky versus people who think that they're unlucky. Like what are the different kind of behaviors?
And one of the main ones is the people who think, who call themselves lucky tend to be the sorts of people that go to conferences and say hello to people and will talk to random strangers in coffee shops. And I was like, damn, I go to conferences and I say hello, but I don't do the coffee shop thing. So I'm kind of glad that you don't either. Yeah, that makes me feel better. It sounds like I might do it a little more than you. But yeah, I just feel like,
I'm a big proponent of saying yes to random things. If someone's like, hey, do you want to come to this thing? It's like, yeah, let's just do it. But I don't know. I don't know if you have to talk to the person in line, unless there's a reason to. I don't know if you have to be that person to be lucky, if you will. Yeah. Yeah. I think my heuristic for a lot of things is, would I be likely to regret doing this? And usually the answer is no. And so I just kind of do the thing, even if it comes at the expense of
Like, for example, this podcast recording tonight where I'm kind of recovering from the flu and I was like, oh, I don't know. You know, I should probably just sleep early because I've got a flight tomorrow. I was like, you know what? Am I going to be likely to regret meeting up with you in real life while we're in the same city for the first time in God knows how long? Probably not. Let's just see if we can make it happen at like 10 p.m. And I'm super glad we did. And so it's just things like that where often taking a bit of a hit in terms of like sleep or...
recovery and stuff, I do find to be like, I've so rarely regretted kind of staying up a little bit late to do something that seems cool. Yeah, I think I feel the same way. Yeah. This next season of your life. So we talked about the travel thing. And then you went to South by Southwest and you decided, all right, cool, I found my tribe. What happened in this next season of your life? So I decided I'm going to work at a startup. Like this was the plan from three years ago. I was like, I'm going to move to San Francisco and we're going to start up. And then I was like, well, I got laid off. I did freelance. I traveled.
So I basically went around and I was like, I was trying to figure out what the hottest companies were. And as a proxy for that, I was like, who's raising a bunch of money? Who's doing interesting stuff? The iPhone 3GS had just come out, had location and GPS. And there was a company that was started by a bunch of ex-Dig people. And Dig was like a really hot internet company. I was like, I'm going to go work at this company, Simple Geo.
Like, my tactic wasn't apply to 10 jobs. It was I'm going to work at Simple Geo. That was it. I didn't have a plan B. So I didn't know anyone that worked at Simple Geo. But I asked someone I knew who knew one of their investors if they could connect me with the investor. And I was just like, look, I am so excited about this company. And I made this probably like 20-page PowerPoint presentation about why I was so excited about the industry and the company.
Looking back on it, I was like, I didn't know anything. Like I was like, it was ridiculous, but that didn't matter. What mattered was that some random kid was so excited that they made a presentation about their company. Like most people are trying to hire, convince people to work for them. And I was out there trying to convince them how excited I was about what they were building. And I think they saw that. And I now know having been on the other side of the situation, like if anyone does that kind of work, you should at least entertain a conversation of whether you would hire them. Yeah.
And so they were like, come on, and you can do business development. I was like, great, what's that? I feel like the theme of my career is like, you're going to be a investment maker. Great, what's that? You're going to be a management consultant. What's that? And so the idea was we built this product, but we didn't know who to sell it to. So it was like, can you go meet people and see if you can sell this thing we built and maybe kind of tell the engineers who are building it what they could change so that you could sell it.
That wasn't a successful endeavor. Like the company wasn't. It turns out we had a really cool technical product that this, like the actual software we built was really, really fascinating, but there wasn't a really monetizable use case for it. And so the business didn't work out, but yeah,
I think joining a company that had a really great reputation, that was right in the middle of some kind of theme emerging, that was founded by a bunch of notable people, or at least people who'd left a notable company, meant that even though that company went under,
10, 15 years later, when I talk about having worked there, people are like, oh, I remember that company. Like it still stands out even though it failed. Um, and the network of people I've met at that company because it attracted similarly other really, you know, amazing people, um,
You know, we're people that I stay in touch with and I've worked with since. And so it was all worth it, even though the whole thing, you know, only lasted a year because the company kind of didn't work out. Yeah. But in that process, I met a few other people who were like, hey, we're starting this other company. Do you want to come over here? And I was like, great, let's go do that.
And I was like, what should I do here? And they're like, well, we don't really know what you're going to do. We just know that we're not going to hire a person to do really anything other than design and engineering. So you're going to do all the other things. I was like, great. I'm going to learn to be a product manager and a researcher and an accountant and all the things. So I kind of played that like, go start another company. And that company ended up lasting about a year before we got acquired by Google.
So I went to Google and I interviewed at Google. And at the end of the interview, they were like, you are a product manager. And I was like, great. I don't know what that, I had no idea what that was. And so they send you to training and they're like, this is product manager training. And I was like, great. Now I know what my job is.
And I worked at Google for about three months as a product manager. And then we had this unique opportunity to go to Google Ventures. And I was like, do you want to go be a venture capitalist and invest in startups professionally for three years or continue down this product management path? And a small part of me
thinks that I might have had a much more interesting path if I had stayed. But the vast majority of me thinks, of course, I made the right choice. But I do think there was something to be learned from, you know, Google is an incredible product building machine. And had I stuck it out and learned in multiple different areas of the company how to build products the way Google does, I think that would have been a great learning opportunity. Just not as great as seeing what it's like to invest in, I don't know, I think in my time,
At the fund, we invested in 150 or 200 different startups, took pitches from thousands. So that experience, I think, was far outweighed it. But I still wish that I'd gotten to kind of peek behind the product curtain at Google for a little bit longer. And I guess you enjoyed these jobs, unlike investment banking, management consulting, that kind of thing. Yeah, I mean, the product management one was a bit weird because I landed at Google+.
Which, at the time... I haven't heard that phrase in ages. At the time, Google Plus had about 1,000 people working on it. Which I think the internal funny joke was like, at any given point in time, there are more people building Google Plus than using it. At least actively using it. So I think I didn't love...
That org was so big, but it probably didn't need to be anywhere near that size that everyone was working on some tiny insignificant thing. But the core product didn't even have product market fit. So it's like, can you work on the notifications for a feature that no one's using that's part of a bigger feature in an app that no one's using? Like it felt insignificant. But Google pays you well. So you're like, oh, maybe I'll keep doing this.
But fortunately for anyone working on a product like that, Google, eventually they realized that and they're really good about letting you move on to other teams.
I got the chance to go do venture capital, which I think was the most fascinating job ever, which was like, I just get to go see what people are building, listen, understand, invest in things that I believed in and watch them kind of evolve and grow. And that was amazing. And lasted about three years before I was like, I'm ready to go do it again. And so eventually left to go start another company. But yeah, it was, I finally found a job where I was like, I kind of like doing this. This is cool. You can enjoy a job.
And how old were you when you started at GV? Like, what was the... 28. Okay. So sort of seven years into the world of work, I guess, in inverted commas, you finally found the thing like, oh, I actually really enjoy this. This is good fun. Yeah, it was funny because about three years into investing, I had this thing. So some of the best investors are not people who've ever built companies. So it seems counterintuitive. You think, oh, the best investors in startups, you would think maybe, or at least I did, were successful founders. They built companies.
Some of the most successful ones are actually people who love investing, right? They're looking at it as an investor, not as a founder. But I kind of had this imposter syndrome where I was like, gosh, how could I be trying to help entrepreneurs figure out what to do in their business when I've never built a business that grew past 10 people?
And so I think the thing that ultimately, and as you invest in smaller companies, I was investing first in companies with three or four people. And I was like, well, I've done that. I've been a company of three or four people. And then as I moved to bigger companies, I was like, how am I supposed to convince someone who's running a company with a thousand people that they want me on their board? They want me to sit at their, you know, at the table and advise them on what to do. I was like, I can't do that.
I've later learned that just a passionate, smart person who is really invested in your business can bring a perspective that is really valuable. But at the time, I felt like in order to earn the right to sit at that table, I needed to go back on the other side.
Okay, so I definitely want to go into the follow-up story of the company that you then started. Two tangents I want to explore before we get there. The first one is that you mentioned that when you were at SimpleGeo, a lot of the people that you still keep in touch with and stuff, you're still kind of friends to this day, that kind of thing.
You're, I feel like you're sort of way above average in terms of people I have on my WhatsApp who are, I feel are good at staying in touch with people. And I always like, you know, you've emailed me, I think two or three times in the last, in the last few months, just like for no reason at all, just like very kindly sending me your like grain recording of like podcast growth strategy. And every time I get one of those emails, I'm just like, wow, that's so good. Like purely like,
you aren't expecting anything in return. You're literally just being super, super helpful and super, super nice. And it takes me for six months to reply to the email and I feel terrible. I'm like, oh, why am I so bad at keeping in touch with people? Why is Chris so good at it? How do you do such a good job of staying in touch with people? I would say some of the answer comes at the...
at the counter to why am I not focusing more on the things that are the most important? Maybe I'm good at staying in touch with people, but I could be spending more time on all the hacks of the business. So maybe there's one element of that there.
I wish there was this app, this amazing app a long time ago called eTax. It doesn't exist anymore. But what it would do is it would similar to how a lot of these banking apps, you'll give them your login, they'll go to your bank, they'll log in with on their servers and they'll download your transactions. It did the same thing for your cell phone carrier.
And it would log, it would go download your bill or your usage data of all the text messages you've sent before there were WhatsApp and iMessage and all that and all your phone calls. And then it would also sync with your Gmail and it would take your address book and it would be like, we know based on whether you texted, called, emailed, or had a calendar invite with someone when the last time for every one of your address people, you know, you've communicated with them.
So it'd be like, okay, you haven't talked to this person in a year. And you could set reminders. You could say for all these people, if I haven't talked to them in a year or for this person every three months, remind me. And then it would look at all the data and reset the timer every time you communicated with them.
I wish that existed because I would definitely use that. I don't have a sophisticated system. I wish I did, but I'm one of those people that when I'm walking, I'm like scrolling through my phone book all the time. That's like my habit. And I'm just like looking. And if I make it to the Ds, then the next time I try to remember that it was, I left on D and the next time I'll just scroll from D and I'll just find someone. I'll be like, oh, I haven't talked to that person in a while. I wonder what would be interesting to send them. Like say, hi, how are you doing? Or maybe there's something.
That's one element of it to the point that I've even created like subgroups of my address book that are like, one of them is called walking calls. And they're like people that if I'm going on a walk, I feel like I could just randomly call them. So I'll go to that group. So that's one is just like using my free kind of mindless time to try to find people that I want to stay in touch with and just forcibly staying in touch. The other is, and I think this comes from content creation as a thing that I've found later in life.
I love going deep and learning things. So in the case of what I sent you, I was like, I went really deep and I tried to figure out all of this stuff about podcast growth. And I realized that I was having the same conversation with lots of people. They're like, oh, I'm really interested in podcast growth. Can we talk about it? And we talked for 30 minutes and I was like, oh, I should probably record that. And the idea came from this guy, James Beshara, who has a podcast called Below the Line. And we'd been talking about something and I sent him an email and he was like, hey, I
I'm really trying this asynchronous communication thing. So could you just send me a loom? And I was like, you don't even want to talk to me? And I was like, okay. And then I was like, wow, this is magical. Because then when we're communicating this way, I can listen to everything you tell me on 2X. So like life's more efficient. And then I was like, oh, and if I record something, I can share with more than one person. And so I thought, oh, I gave this talk at a conference about podcast growth.
why don't I just actually record a version of it that I could just send to people? And it wasn't like published on YouTube. It didn't have, but it was something I could send to people. And now I'm starting to think about, Oh, every time I learned something interesting, what if I found a way to share it with people? So I do that with the podcast, which I think seems almost too public. If I'm like, Hey Ali, I found this, I recorded an episode. Here it is. You'd be like, okay, well that's like anyone could go subscribe to the feed. I've started doing like the private version of it. And,
And I would encourage lots of people to try to experiment in this way. It takes different forms. This guy, Nick Gray, who wrote this great book called The Two-Hour Cocktail Party. Oh, okay. It's literally like he has optimized throwing an event to meet and build relationships with people to the nth degree. It's fantastic. Sick.
Sick. He has a friend's newsletter where he just puts his friends on this newsletter and he sends an update maybe once a month about what's going on in his life, some cool links he's found, just as a way to keep people in touch with what he's doing in life.
So you can send a friend's newsletter. That's nice. I love it. You get this friend's newsletter. He's like, oh, I found this cool thing. And every time he goes deep on something in his life, he's like, you know what? I feel like Calendly, which he uses for scheduling, could be a little more dialed in. So he goes really deep and he's like, you know what? Here's how I think you should change the default settings. Here's what I think you should put in the thing. And then he just writes a little blog post. And then he's like, I'm going to send it to the people I think might find this interesting.
So now every time I come up with something I think people might find interesting, I'm like, who might find this interesting? Let's just send it to them. I'm not like, hey, you have to watch this. I'm watching the links. If you don't click it, you know, I'm going to be upset. It's just why not send people things that they might find interesting and helps you stay in touch. So if there's something you've learned recently, if you're listening to this or an idea or a tip you have,
Don't feel like you have to go to the extent of like, I'm going to create a blog or I'm going to record a YouTube video. The video I send you on podcast growth is not worthy of YouTube in its kind of view, you know,
in the quality of the production, right? It's like me recording myself, like running through slides and keynote. So I don't feel great about putting on YouTube. And if I wanted to put that video on YouTube, I feel like I need to go hire an editor or like learn all this stuff. And so it was a really big hurdle for me, but to just record it, send it to you. I'm like, you're not going to judge me for not having a super high quality thing. If the content's good.
So I think for anyone listening that there's something you're dialed into or you learned a lot about, maybe try recording a Loom video or an audio note or writing it out and just send it to anyone you think might find it interesting. And I think you'd be surprised how if you've done a little bit of research, people will find that valuable, especially if you go to a place.
I have friends that every time they go to a place, they create like a, even like a Google doc of like my Paris recommendations. Oh, that's so handy. And then, and then someone's like, you hear someone, they're like, oh, I'm going to Paris. You're like, hey, let me just send you this Google doc I have of Paris stuff. And now I have one of London. Like, you know, I think it's just something that's so easy because you've already done the research. So take the research you've done on anything in life, share with people you might find interesting, and it makes it really easy to stay in touch with them. Yeah. That's so good. Those are fantastic. Okay. Yeah.
how do you manage your WhatsApp? So it's really easy when you live in the States. I have like three people on WhatsApp. So managing WhatsApp is like the easiest thing in the world. Is it iMessage for everyone else? Yes. Okay. Yeah. I don't, I have like the group that we are in on WhatsApp and one friend that lives in London. Oh, wow. Okay. So like WhatsApp for me. How do you manage your iMessage? Yeah. Yeah. So I,
I use iMessage on the computer and I'd say like 90% of the texts I send are all done on the computer. It's not the most organized. I don't have like a system other than that I hate red dots. So like I've got to respond to it. And until they had mark unread, which still leaves you the red dot, but like there was just, it was like, I've got to respond. So I would say no system, no fancy way to manage iMessage other than like... But basically inbox zero in terms of unreads. Yes. Yeah. I'm not someone who has like a million unread messages. It's like, I've got to respond. Okay.
Do you have a lot of red dots? Oh God, I have sort of hundreds of WhatsApp unreads, hundreds of iMessages. And it's one of those things that I really, I aspire to be the sort of person that will respond in a timely fashion when someone messages me.
And every time I set that intention for myself, I decide, you know what, I'm on the toilet right now. I'm here for at least 15 minutes. Instead of scrolling Twitter, I'm going to scroll my WhatsApp messages and reply to people. But then it's sort of like email. Any reply I send generates more. It becomes an infinite kind of infinite loop, an infinite well of things that I then feel like I have to respond to. And then if I don't respond to it in a timely fashion, I feel like, oh, it's been like two days already. It's like it's too late to respond now.
I think everyone feels this way. How do I get over this? I think everyone feels this way. So if you respond two days later, I don't think that's a problem. I think...
who I just thought of because you have a book of his over on the wall. But I think he's like, I process things like irregularly. He's like, I don't even like to respond the same day. Even if I am here, he's like, I'll wait a couple of days. So I now, I like kind of respect people that take a few days to reply to things. Cause I'm like, Ooh, like this person, you know, is prioritizing their time. This wasn't that urgent. Um, so I definitely wouldn't not reply cause it's been a few days. That's it. And I definitely wouldn't feel like you owe everyone a reply. I,
I feel like that's something hard to get over as someone who has like an audience and everybody that writes you. I feel like it's really hard. I would try to come up with scalable ways to solve that. If you have a bunch of listeners that send you questions and you want to answer them, maybe do a listener Q and a episode, maybe do something like that. Yeah. But for just general friends and stuff, um,
I don't know. You just decide, is it important? If it's not, that's fine. If it is, I'm sure there's time. I think that like the funny thing about time management, someone, I can't, I think Laura Vanderkam uses this example of like, look, if your water heater breaks, you're going to find a way to get it fixed because you need hot water. Especially if you're in London this week, you definitely want some hot water in the shower. But yeah,
You didn't have six hours that day. But when you needed to solve a problem, you found the six hours. So I think you can always find the time. If it's not important, that's fine. But if it's making you frustrated feeling like, I don't want to be the person that everyone's like, God, this person never responds. You just have to prioritize it. You just have to decide, okay, let's block an hour for going through WhatsApp and responding to things. Yeah.
I wish there was a, sometimes I like to work offline with email where I'm like, I'll send all these emails. And even if I'm not offline, it's like, I'll send them all at 4 p.m. I use a lot of send later with Superhuman just so that I don't, before I'm done triaging the inbox, I don't have a bunch of stuff coming back in.
So that's an easy one, but I don't think it works on WhatsApp. It doesn't work on iMessage. Have you tried text.com? Text.com. Text.com. Oh, it's amazing. It's like superhuman, but for all of your messaging services. Including iMessage. Including iMessage. Including WhatsApp.
That's been the thing that's allowed me to most because then it sort of it's like WhatsApp web, but just better. And it's like iMessage, but better. And it's all in the same interface. And you can even do fancy things like have groups and stuff. And I haven't gotten to that fancy level yet, but it's just sort of superhuman level keyboard shortcuts in terms of being able to archive things and search conversations. And so that's been that's been one thing that's actually helped me probably two or three X my ability to respond to people.
even though it's still not quite at the level that I would like. But I think, yeah, you're right. I just need to prioritize it. And currently it's not really a priority. I'm just like, whatever. And at the point where it becomes a priority, then maybe I'll start thinking about it. So that was one tangent on keeping in touch with people. I wanted to explore another tangent, which is, I'm curious, like, how do you think about money? Very broadly. Just broad, you know, like just money. Yeah, just psychology of money. Let's go. Yeah.
I think my outlook of money has had a fun evolution through my life. I think early on, I was like, well, I just need it to live. And it was like, oh, now I need as much as possible. So I went down the financial independence path pretty deep because I was like, I need as much money as possible because I haven't found a job I love and I don't want to work at a job I hate. So my relationship with money there was I need as much of it as I can save. However, I think one theme that has stayed relevant the entire time was
was I'm not willing to sacrifice the kind of things that I enjoy doing. So it was like, I want more money so that I don't have to work a job I don't love, but I still want to travel. It's not that I was unwilling. I was unwilling to give up those things
But not at the expense of spending the money, just at the expense of finding creative solutions. Like you can play the points game if you want to travel for free or you can find interesting deals or you can go couch surfing. If you want to live in a nice place, you can go down the world of house hacking and like get an apartment that lets you rent out a room and maybe you can get one that has a separate entrance so you don't even have to have a roommate, which we did. So...
I guess I had this process where I looked at all the way we spent money. And I was like, let's go through each thing we spend money on and find out, is there actually a way that we could spend less money on this without having to give that much up? So I don't know, little things. Like we wanted, we found out when you have kids, you stop eating dinner at 7.30 and you start eating dinner at 5.30.
Well, we were almost never done with work by 5:15, 5:30. So we were like, how do we cook dinner? So one option was you end work early. And then the fancy version was what if we had a chef? Like wouldn't that be nice? You just have a chef come to your house and cook dinner for you. It's like wonderful. So we were like, that would be great. But that's really expensive.
So I put an ad out on Craigslist. I was like, does anyone that lives in this general region like cooking? I don't need you to be a fancy Michelin star chef. I don't need you to come to my house. But could you just cook basic meals and put them in glass Tupperware and once or twice a week drop them off at our house? And we found like 20 people said they could. We found a few. And then someone would drop it off. It ends up costing about halfway between like DoorDash or, you know, whatever other delivery service, Uber Eats, and just going to the grocery store yourself.
But you don't have to do the cooking and you don't have to do the grocery shopping and you can kind of plan the menus in advance. So it ends up having this added health benefit to if I'm at the grocery store by myself, maybe I'll pick something unhealthy. I know for sure if I'm ordering food, I'm picking something less healthy. So it's like you get a health benefit and a time benefit and it's not that much more expensive.
Now, if I hired a chef, it would have been way more expensive. So I feel like, you know, in that window of time, I felt like I had a chef in our house, but I didn't. So I think my outlook on money is I don't want to spend it
if I can avoid it, but I do want to have great experiences, whether they're travel or lifestyle or anything. So I think that's like the whole theme of my life is trying to find ways to, you know, upgrade your life, your money, your travel, everything while spending less and saving more. Oh, love it. Is business class worth it? Business class? Yeah. And flying. Oh, flying. Yeah. I mean, worth it is interesting. Have I paid for business class?
I don't, if I have, it was like one time on a domestic flight when it was like, oh, do you want business class for an extra $100? Have they ever paid $1,000 for business class? No, or more, never. Have I crossed an ocean in economy in the last seven years? Probably not also.
And so the answer and for people who live outside of the States, this is maybe not the most fun answer. But like in the States, it's just so easy if you play the points and miles game to accumulate enough miles and points that you can, you know, fly business class for free. So I've just got it. Yeah, it's totally worth it if you have a way to do it without spending a lot of money.
And the opportunity cost for me is I could probably go on twice as many trips in coach as I could in business because it usually is about two times as many points to fly in business as it is in coach. So I think it's worth 2x. The arbitrage opportunity is that when you go buy business class, it usually costs like 6 to 10x. So the points needs are like 2x and the dollars needs can be 10x. Do I think business class is worth it at 2x?
Yeah, probably. It just unfortunately never is. And funny enough, when you add in the cost now, at least for certain destinations of like, oh, I want to pick my seats and I want to check bags, which you have kids now you're checking bags. Now you're like, wow, it's really getting close like to 2X. And because business is often like 2X the base fare, right?
but it includes the free check bags. It includes, you know, picking your seats or maybe you don't care because all the seats are good. So I don't know. It seems like I would say, yes, it's worth it, but no, it's not worth paying for. Have you, what about like, okay, just some more specific questions on this stuff. Have you found, let's say if you're staying in a hotel and
Hotels range from like 10 pounds a night to 10,000 pounds a night. What is a good sweet spot in terms of nightly cost? Has someone done an analysis on this? I'm kind of slowly doing one myself in my head, but like, I'm sure this is a solved problem.
I mean, I think at the end of the day, the challenge is like, okay, so what are you optimizing for? And I think there are a lot of ways around this. So one, I became a travel agent. That helps on that. Oh, wait, what? Two, you can use, there's a great travel hack that is probably one of the ones that's been most valuable to everyone that listens to my podcast, which is,
Book a hotel. Book directly with the hotel. Don't use booking.com. Don't use TripAdvisor. Book directly with the hotel. Email the hotel after you book. And if you can't get their email address, call the front desk. Say, I need an email address for a general manager, you know, someone. And just email and say, hey, I just booked a night at your hotel or a week at your hotel.
I'm coming with these people in my family or just me. I'm really excited. If you're celebrating something, great. If you're not, that's fine. Don't mention it. I'm not someone who's like always telling someone it's our honeymoon. It's our honeymoon. I'm kind of pretty straight, straight and narrow for that one. But, and just say, Hey, we're coming. Really excited to stay looking forward to stay in your hotel. And then three days before check-in follow up and say, Hey, just want to let you know, we're still coming. I'm really excited for this day. I have seen almost,
let's say 50% hit rate on getting upgrade, free breakfast, bottle of champagne, chocolate-covered strawberries, one time initials embroidered on the pillows, all kinds of stuff from an email. Literally just sending an email where you're not even asking for anything, you're just saying, "Excited to be staying." You're not asking for anything. And the crazy thing is that this whole industry still thrives on hospitality. And it's still so deep in the culture of hotels.
But when you book through all these other channels, they have no way to build a relationship with you because the relationship is owned by booking. The relationship is owned by TripAdvisor. And they have to give up such high commissions to those companies that, you know, in general, they're like, well, this person doesn't care about staying at our hotel chain. This person just cares about getting the cheapest price. And next time they're going to go stay somewhere else.
But when you're like – when you take the time to book with them, they're like, well, you took the time to book directly with us. You must want to build a relationship. We should build a relationship with you. So that didn't answer your question at all. But it does increase the likelihood that if you book something slightly lower in price, you'll get a better experience. For me, it's really like –
a balance of where you want to stay, what you need in that hotel, trying to find a deal. There are some times that I won't book direct because I could find a great deal. So if you follow at hotel on Instagram and you send them a DM, they'll respond and they'll give you a link to go to their website and book. And you can get anywhere from like,
20 to 60% off different hotels booking through them. Oh, wow. From this interesting arbitrage thing where hotels are not allowed to sell a room at a lower price than they give to everyone. Okay. So hotels sometimes pay 10 up to 30% commission on sites like Booking and TripAdvisor. Hmm.
If they sold that room for 30% less on their website, they would make the same margin on that room, but they're not allowed to because the agreements they have with all these agencies are that they won't price below what they tell them to the public. But when you DM Hotel on Instagram and you get a response from them,
then they take you to a site that's not available to the public. And you could argue it is because all you had to do is DM them. But it is not a website anyone could just type in the URL. So they're able to offer you these crazy deals. And so as much as I love booking direct, if I could book a room for 60% off, I'm happy to not have any chance of getting an upgrade. You could probably just book the upgraded room and still come out ahead. So...
I don't know. I feel better about getting the best value. Like I almost optimize more for making sure that I'm getting the best deal than that I'm, you know, spending a certain amount. Like at the end of the day, if I want a hotel that has XYZ features and is this level of clean and central, like I might just have to spend a certain amount of money for it. I just don't want to spend any more than the bare minimum I could possibly spend to get that quality room. Yeah. What's the deal with having an au pair?
What does an au pair do? And to what extent is this a hack for having kids? Yeah, so if both people work and you need to have some kind of childcare, the options generally are you send your kids to daycare until they're old enough to go to school. You get a nanny that comes to your house and helps the kids during the day and then leaves.
You could get in a live-in nanny or you can get an au pair, which is someone from another country. I think they have to be between like 18 and 27 and they stay with you for a year. And it's part of, at least in the US, it's part of a cultural exchange. So the idea is they're like getting to experience America. They're part of the family. They stay in the house. We, you know, eat meals with them. If we go on a trip, we'll bring them with us and all those kinds of things. So it's something that not everyone wants. Like not everyone wants someone in your home. Hmm.
But, you know, I remember I was listening before I came over. Our daughter was going to bed and our au pair was helping her with bedtime and they were singing songs in Spanish. And my daughter, she's from Spain, our au pair. And so, you know, it's like this cultural experience for our daughter getting to, you know, experience someone from another country and learn a new language. We love just like traveling and getting to meet interesting people. So for us, having someone in our home wasn't that big of a deal. But I know that's probably the biggest deal breaker. Yeah.
But from a cost standpoint, if you live in a high cost of living area, even if you pay above the minimum – like in the States, they're like here's the minimum stipend you're supposed to pay each week. I'd say probably 50%, 70% of people are paying that. Even if you go above that, you're still at a significant discount to a nanny who has to pay for housing in the city you live, which can be expensive. Yeah.
You have to commute to where you are and needs a car and all these other things. So I don't know. I think it's an amazing thing. I think if it were the same cost, we'd probably still do it because it's an experience we like. It just happens to be a lot less expensive. Yeah.
When I was a kid, my parents, we had an au pair. We had four au pairs four years in a row, all from Norway. And like, I remember this one guy, Espen was like, and who knows how much of this is true because I was a kid, but I swear he was the best Lego builder in the world.
And I have all these amazing memories. I was upset. I thought my au pair was the coolest person ever. I brought him to show and tell. One day for school, it was like, bring something cool to show off to your friends. And people were like, here's a cool rock or here's my skateboard. And I was like, here's this 24-year-old man. But I thought it was so cool. And I had all these great memories as a kid of this person who was living at home. And I got to get to know them. And we were having a good time. And
I don't know. So it was just something that we wanted to try and the experience for us has been amazing. Nice. That's pretty cool. I'll definitely hit you up as I'm going to have kids to be like, right, I need more hacks about the whole kids thing.
So here's another great example. I made a Notion page that's just like, you know, my baby planning thing. It's like, here are all the things that I thought we wanted to buy. Here's some ideas. Here's some resources. Here are my favorite books and resources, like all that stuff. And so anytime I meet someone that's like, oh yeah, you know, we're having a kid. I'm like, great. Let me just send you this doc. That's handy. Like, and then they're like, oh wow, thanks for thinking. That's so cool. So, you know, just another example of like my podcast growth video and this thing. You know, this is a great idea. So like, I've, I found myself doing this
You do this. You have your like gear guide on your website. Yeah. But that's more like a sort of public for audience rather than for friends. Yes. But you have, I'm sure there's something in your own personal life. So one thing that me and my girlfriend do is regular relationship reviews. And we have like a notion page where we answer these like 10 questions every couple of weeks. And everyone I've mentioned this to is in a relationship says, Oh, I'd like some of that for myself. And I'm like, Oh, okay, cool. Let me go and screenshot it, like a drop of all that kind of stuff. I could just copy and paste it into like a
more public Notion page. It'll be like, I'll send you a link. And this is a very easy thing to do. And it also makes people feel like, wow, you sent me this cool thing that you don't give everyone. Even if you've given it to hundreds of people, it still feels really interesting. Yeah, I have no idea how many people you sent the podcast thing to, but I feel so special when you sent it to me without a BCC or a CC chain or any of that kind of stuff. It's so good. So you probably already have these in your life and you can start doing them. And even little things, like I imagine...
If you took a list of like the 10 restaurants that you love in London, you sent me one. I'd happen to already go there. But like anytime you hear someone's coming to London, you're just like, hey, here's a few things that I love doing. You don't need to provide me with a six-day itinerary. Though for anyone listening, I literally by the time this comes out, we'll have done an entire episode on London. So maybe, you know, we'll see. Ali's guide, my guide, we'll see which one's better. We'll see, yeah. I don't know. I feel like the bar...
It might be harder for you because you're so used to creating such great produced content. And so you're like, oh, do I really want to make like a friends YouTube? No, no, just make something simple. No, just like a quick notion page. It'd be so easy. Yeah, it's because when you asked me any restaurant recommendations, I was like, huh, that's actually a good question. And it's like, I've been to lots of good restaurants and I've kind of saved some of them on Google Maps, but some of them not like,
I could just make a notion page because so many people ask me for restaurant recommendations when they come to London. It would be such an easy thing to do. Yeah. Or even if you go to another place. Like I just went to London and I'm like, wow, now I have some recommendations. I have a bunch of recommendations for Japan. If people are going to Japan, I'm like, here's all the stuff I love. I think it would be so easy. And then it creates this cool thing that anytime someone's going through something. And by the way, when someone's trying to plan a trip or have a kid or do any of these moments in their lives,
They're probably overwhelmed with information. So you're like, hey, I've got you. Like, I've got this thing. Trying to grow your podcast. Trying to, you know, I don't know. I feel like you're going to have great relationships in 2023. Okay. So at this point, you've been at Google Ventures for three years. Going back to the backstory. And you decided you're going to start your own thing. Yeah. What was the story there? So, we were talking about money. So, yeah.
I've always been someone that people are like, hey, you seem to have money figured out. Not that I had so much of it. It's just like it wasn't a thing that stressed me out like it does for so many people. I assume this is a global phenomenon. But in the U.S., money is the number one cause of stress and the number one cause of divorce. I imagine it's very similar here and in most Western countries, if not all countries. And so...
I just was someone who was very pragmatic about it. I was like, okay, well, here's how it works. Here's what it does. I go read these books and I think about it. And most people don't like thinking about money. I think that's the difference. It's like, if you love thinking about money, it can be really easy to figure out. If you don't, you can't. Or if you don't, then it's harder.
And so people are always like, oh, what do I do? Like, what should I start doing in my 20s or my 30s? Or like, we're having a kid or we want to buy a house. And I was always like, oh, well, when I bought a house, I was like, okay, here's all the mortgage options. Here's how I thought about how to buy the house. Here's how I, you know, house hacked our way to buy a house that I think was a way better deal than anyone else could have found if they were trying to just look for a normal house. And, you know, we did this weird thing with real estate agents. And, you know, we could go pretty far down just that, but we won't. And...
I realized that everyone was all stressed out. And there was a process that many people use called financial planning. And there are professional financial planners, there are certified financial planners, there's kind of a thing they do, which is like, let's understand how much you're saving, how much you're spending, let's understand what your goals are, let's understand how your money is invested, what your risk tolerance is, and let's come up with a plan, see if you're on track for what you want. And if you're not, let's come up with a plan of what you need to do to get on track. Like it's, it's not actually rocket science, what you do.
And in many ways, most financial planners and financial advisors are probably more therapists than financial professionals. But the process of going through financial planning is something that almost everyone I've talked to that's done it goes in stressed out and comes out feeling a lot less stress and more peace of mind. That doesn't mean they have all the money they need and everything's already perfect, but they're just less overwhelmed.
So I was like, wow, why doesn't everyone do this? Like, why doesn't everyone go through financial planning? It's like, hmm, well, the average cost of financial planning was like $2,700 or $2,600. It's like, okay, well, that's pretty expensive. That's a high price ticket. That's probably a big barrier. Turn
Turns out there were other barriers that I didn't know at the time. But I thought, okay, clearly that's a big barrier. I know a lot of people aren't willing to spend a few thousand dollars. Why does it cost so much money? And you go talk to financial planners. I interviewed a ton. It's like, okay, well, to get to know you, I have to ask you to bring your financial statements and email me all these PDFs. And I was like, why aren't they building software that aggregates all your accounts? Mint has been doing this for years. There's Plaid and Yodlee are aggregating tools. Why is no one doing this?
And the short answer is most financial planning clients, because of the price, were all a much older generation. And they didn't want those services. So the tools they were using weren't really built for this new generation. There wasn't really a thing there. And...
So I was like, okay, well, what if you just automated away all of the time? So if you looked at how advisors spend their days, half of it is attracting clients, not half, but like a good part is attracting clients because the way they do it is they take people out to lunch because that's what you need to do when you're charging $3,000. Another way they spend their time is collecting all this information, processing it, then like manually entering it into this like old school financial planning software. It was like, what if you just,
Use software to replace all of that. And you use the humans for the things that are the most important, which is having a conversation with someone about their goals and helping them think about the prioritization. That seemed to be the thing that was necessary.
So I was like, great, this is my great idea. We raised money, I think in total, like $10 million over the course of a couple years. We built a team of 20 people. We had almost a dozen financial planners. And it was working at some scale where we had hundreds of people that were paying customers. But one interesting thing happened, which was we asked people that wanted to lock in the introductory discounted price to put $100 down.
And this ultimately led to us raising a bunch of venture capital money. And we collected $100 from a lot of people. And then we said, hey, it's your turn finally. We've hired the advisors. We're ready to onboard you. Do you want to go? And they're like, not right now. And we're like, oh, we're so sorry. Do you want your money back? And they're like, no, no, no. I don't want my $100 back. I just don't want to do it now. And we're like, hmm. You paid $100 to get early access to this thing. Now that we're ready for it, you don't want it.
And what we learned slowly over the course of, you know, maybe a year, a year and a half is that financial planning is just never a priority. Like people have so many priorities in their mind and in their lives and with their families that it's like to stop everything and go through like a multi-hour process for something that has very little impact in your day, week, month, or maybe even year.
It's really hard. People have so much going on. You got to figure out what am I doing this week? What are we making for dinner? Like, where are we going for holiday? Like, there's just so many things happening that you actually have to solve. I have to file my tax return. You know, like there's stuff that's really deadline centric. And this is something it's like, well, this will make us feel better. But practically, it'll probably help us more 20 years from now than next week. Hmm.
So people punt on it and punt on it. And so no matter what we charged, we just couldn't get people to sign up at any fast rate. It cost us almost $1,000 to acquire a customer. Meaning like we would spend $10,000 on marketing and social media advertising, all this stuff, and we would get 10 customers. But we're only charging like $600 a year. So if you spend $1,000 to bring someone in who pays you $600, and of that $600, some of it goes to pay financial planners, the math doesn't work.
That was a problem. So we tried a bunch of different alternatives. And ultimately, at the end of the day, I hope someone solves this. I've probably gotten 20 people who've been like, hey, I'm starting a company. It looks like it's just like what you did. Could you give me your advice? And I'm like, can you acquire customers scalably? And they're like, well, we're going to build this awesome product. And then we're going to figure out how to acquire customers. I was like, you should probably figure out how to acquire the customers first, because that's the problem. It's getting people to care about financial planning enough that they're willing to do something and spend money and time.
So we ultimately decided that we didn't think it was going to be a good, like the company wasn't going to work. We still had about $4 million in the bank, but we didn't want to just like burn through four more million dollars of our investors' money if we realized that financial planning wasn't the answer. And what we ultimately thought was that financial planning had to be a second product. There had to be something that would get someone in the door that you could build a relationship with them that provided immediate value. And once you provide that immediate value, you can kind of earn the right over time to do financial planning. Mm-hmm.
But what we also realized was that if you could get them in the door with some product that was good, like I'm not trying to like bait and switch you. I'm just saying if you could offer a core product that's valuable and you could learn enough about people, what's more valuable? Is it helping them feel better by having conversations or helping them feel better by starting to do the right thing? And so I met Andy Ratcliffe, who ran Wealthfront, which is a large investment management platform in the United States.
And he was like, yeah, we have this vision for self-driving money where we could just build software that will automate and optimize your entire financial life. And it's really about like taking the best of financial planning and putting it into automation. He's like, would you be interested in bringing your team over and figuring out how we could build something like this? I was like, this seems like this perfect opportunity. And so we kind of wound down Grove. Some of the team came over and started working on this. And
I think it was ahead of its time. I think it was this amazing piece of software that you could say, hey, make sure there's always $7,000 in my checking account. And if there's ever more than $7,000...
I want you to first fund my emergency fund until I have six months of living expenses. And once that's hit, then go and make sure you put enough money in my retirement account. And then go and make sure you put enough, like up to $500 a year or $500 a month into my kid's college fund. And then if there's anything left over, just put it in my investment account. And you wouldn't have to think about it. We call it autopilot. It just would run in the background. You wouldn't have to do anything. I was like, wow, this is awesome. I think people weren't quite yet ready to trust...
Similar to the last story, I think they still needed to build a relationship with you, the brand, in this case Wealthfront, before they were ready to automate it. They weren't going to come over to do automation, but if they were already there, they were willing to automate. So it was a really great product for Wealthfront customers, and I still think it's a really great product for anyone, but I don't think it's the marquee thing that brings people in the door.
But something like, you know, really great investment management or really, you know, high interest cash account, those kind of things bring people in the door. They get to know you and then you can automate everything. And so I actually think for some people that kind of coaching and financial advising from a human could add a lot of kind of therapeutic value. Yeah.
But I almost would rather just help people automate everything and just put the best practices into place. And so that's, I think I went a full 360 or I guess 180 on what I thought, you know, needed to be existing in the market. And, you know, now I love automation. I'm like, automate my entire financial life so I don't have to think about it. Move the money to the right place. I don't know. That's not, you said, what do I think about money earlier? It's like, yeah, I think it should just be automated. You should just keep it simple. So,
So after winding down Grove, you moved to Wealthfront? Yeah, it was kind of like this weird acqui-hire-y thing where they were like, well...
We'll let your team come over here. We'll give everybody jobs. Your investors, the money that was still in the company could invest in Wealthfront. Wealthfront took over our offices. But like no one got a payday. Yeah. We got stock like you would when you join a company. So it was somewhere in between like getting a job and getting acquired but not making any money. Yeah. Obviously, I had a salary. And so, yeah, I spent –
you know, three and a half years building different awesome products in investing and savings and banking and automation and financial planning. And it was awesome until, gosh, like a couple of weeks ago, decided to go full time creator. Oh, awesome. When did the podcast start? Like, how did that come into this whole journey?
Yeah, so during the pandemic, you know, we talked earlier, like I love sharing all these things and I do all this research. Pre-pandemic, I'd go to dinner and I'd be like, hey guys, like I just went on this crazy vacation and everybody'd be like, how did you go on that vacation for free? Like we just went on vacation, it was super expensive. I would like to save money. I would like to go on, you know, so much of,
talking to people that are like deal seekers is like, oh, I know how to go on the cheap vacation. Why don't you rent this really cheap condo that's like 10 miles out of town and take the bus in and you'll save money. And then if you want to go to the beach, you can go to the public beach and you can buy your own chairs. And like, you're like, well, now I'm not really having a great vacation. And then I would come in and be like, oh, guys,
I have this great thing and I'll just tell some crazy story about some awesome adventure and how it costs nothing or how I got a great deal on it. People are like, yeah, so that's what I want to do. Like I want to, you know, I want to live the upgraded awesome life. I just want to do it at a lower cost. And so...
I was like, oh, I was kind of missing having those conversations with people because there were no dinners. I wasn't a blogger. I tried writing a couple medium posts and that never stuck. I tried posting about it on social. That just wasn't my format.
And so funny enough, we were having a child and I did all this research. I went super deep on planning for kids and I built this notion page. I was like, I'm going to start a podcast all about parenting because like I'm deep down the rabbit hole. I'm super interested. So I bought a microphone. I was like, I came up with a list of all these cool guests I wanted to interview. And then we had the child and I was like, wow, I don't know if parenting is like my thing as much as parenting.
optimizing a thing is my thing. And so sure, I can have an episode on parenting, but I don't think I want to have a parenting podcast. And so I realized as I started thinking, I have this microphone, I might as well start recording something and see what happens. What do I love doing? And I was like, well,
I love optimizing travel. I love money. I love life. I love health. I love like productivity, like all these different parts of my life. I like kind of going a certain amount deep till I figure like it's dialed in. And then instead of taking that last 10, 20%, maybe let's find another thing in my life and go deeper there. And so that became my thing, launched this podcast, put out in the world. And I was like, Oh wow, people like this thing. Like, I guess my idea was put it out, do six episodes and commit to a season one of six episodes and see what happens. And,
And it just worked and people liked it. And, you know, I think I had the fortunate, the good fortune of a few people helping share it on the early days. But you can have all the promotion in the world and all the marketing success. But like, if it's not good, people aren't going to come back. And so I think I was fortunate to have the kind of amplification during launch that not everyone has.
But lucky that the thing that I decided to talk about was something people wanted to come back to. And I think I was like, wow, if people are going to come back every week, like I need to produce content every week. And the one goal I had was I was going to be a weekly show. It's going to come out every Wednesday at 2 a.m. Pacific. And
I don't think I've missed a Wednesday yet. I know I haven't missed a Wednesday yet. I have missed 2 a.m. Pacific. Technically, I hadn't, but there was a button that's like, mark this episode private. And somehow that button got clicked. So the episode went live at 2 a.m., but no one could find it until about 4 a.m. But yeah, so it became this thing. And it's about one-third travel.
So it's not just miles and points, but like, you know, we talked about some cool travel hacks. It's about one third money and then one third everything else from, you know, health to, like I said, planning a cocktail party or anything. Well, how did you get the amplification in the early days? So I got this weird email.
from a YouTuber or I guess a internet video maker, Nas Daily, who you've probably met, I'm guessing. And it was this weird email. I'd never met him. I didn't even know who he was. And the subject was from television ASAP. And I read this email. And I'd later have met him and told him this story. And he was like, you have to send me this email. That doesn't sound like something we would send. I was like, it was. So he sent me this email. He was like,
He didn't. Some person did. And they were like, oh, we want to make a video about you. You have all these credit card points. At the time, I had done this weird article on CNBC about having 12 million frequent flyer miles. And they were like, we're going to come to your house and make this video. I was almost convinced that it was a scam. Yeah.
It was poorly written English. It was like nothing about it seemed legit. And then like an hour later, I got a LinkedIn message. And they were like, it was almost the same message. And then like two hours later, I got a WhatsApp message. And I was like, wow, this person is really. So finally, I was like, maybe I should actually read it. I was like, maybe this is true. Like what's the risk in saying yes? Like if no film crew shows up, then we're not going to make a video.
So I said yes, and we made this video. And so Nas Daily made a video about me. And that was like when he said... Honestly, it was funny because he's in the video. But the entire time making the video, we never met. I never communicated with him. Anything. So I say him, but it wasn't him. Yeah, he's got a very dialed-in operations team everywhere in the world. And the only thing I asked, I was like, if you're going to make this video, could you at least...
just mention the podcast. Because I'm not getting paid to make this video. So I was like, if you're going to make this video for your content, I'd love it if you just mentioned that I have a podcast. So we made the video. And I was like, what day is it coming out? And they're like, this day. I was like, that's the day I'm going to launch a podcast. So I launched the podcast that day. His audience is very international. And my audience now is very kind of US, Canada, UK, Australia. And so I think it helped to spread the word. So that was part of the early thing.
Similar to Nick Gray, I've been basically every time I've done something, I've created a newsletter.
When I traveled around the world, I had a newsletter. I randomly had this like annual life updates newsletter. And then when we ran Grove, I had like a newsletter for people. We wrote like a financial newsletter. And I was like, okay, well, all of these things are newsletters of mine or my companies. And they're all related to me, life, travel, or money. So it seemed reasonable to send an email to all of them being like, hey, I now have a podcast about life, money, and travel hosted by me. So like...
So I sent it to four different newsletters I'd built over the last 15 years for random other purposes.
And then, I don't know, you always have one or two people in your life that you could ask a favor for, but you're not going to ask a lot of favors for. And I was like, well, if I'm going to launch a podcast, this seems like the time to ask for that favor. And so I just said, hey, I don't ask for a lot, but do you think maybe you could help reshare this thing that I'm launching? So put all that together. That created enough of an initial momentum to put it out there. And then I just kept making content and asking people if they liked the content to share it. And
Unlike YouTube, podcasts have no inherent growth mechanism. It's like there's no show this to 100 people. If they like it, show it to 100 more. It's just they spread when people share it. But, you know, it's been a slow growth path since then. But with growth and, you know, now it's enough that it was easy to walk away. Easy is a hard word. It was reasonably easy to walk away from a job to do this full time because it's now a business.
Um, still feels crazy because it's not like I, you know, it's not like I've signed any sponsor deals that are going to generate any revenue beyond like six months. So it's a little bit weird, but, uh, you know, it's something that I'm excited to focus on full time. And gosh, it's only been like 18 months. What's it like being a full-time podcaster? What does your week look like? I spent a lot of time trying to figure out what I want the show to be about. I think one of the easy things was if I had done this parenting podcast, I
There's an easy list. Every person that's written a parenting book, every person that's started a company that makes things for kids, every person that is a professor about childhood psychology, childhood education. It seems like there was just – it's so easy.
But when you make a podcast that's about optimizing something, it's a very specific kind of person you'd want to talk to. And oftentimes it's hard to find the person that has the knowledge you want and is, you know, also the right person to come on a podcast and talk about it. So I'm like, okay, I want to do an episode on vacation homes. I was always fascinated, like timeshares, like, are those a good deal? You know, Airbnb is all this stuff. I couldn't find a person. So I was like, I'm just gonna do this episode by myself.
But a lot of it is like trying to figure out what are the things that I think are interesting, going deep on it. I think I wrote 7,000 or 8,000 words today.
about vacation homes for that episode. So there was just like research and a lot of organizing of information. So I'd say it's like a lot of just trying to figure out what the plan is for what we're going to talk about, reading the book of the person I'm interviewing, trying to come up with staying on top of all the deals. Like if I'm going to talk about all the greatest deals and travel stuff, I need to make sure I'm dialed into what's happening. And so...
So literally I feel like part of my job is scrolling this one Twitter list of people who promote deals because I want to make sure I can deliver. And I don't know, trying to figure out what else to do. I started a newsletter.
that was at the beginning, I don't know why, completely different, but also the same. So it was like both under the brand, all the hacks, both about upgrading your life, money and travel. But I would write a newsletter about insurance. And I think in my mind, the podcast at the beginning was an interview podcast. And I was like, I don't know who I'm going to interview about all the types of insurance. Because I didn't think like insurance salespeople were the right audience. But if I'm going to talk about life insurance, health insurance, car insurance, there's no one person who's
So it was so natural to write a newsletter about all of them. And it was so much content that I wrote two newsletters back to back about all the kinds of insurance. It never crossed my mind when I was doing that, that I should do a podcast about it because I didn't have a person to interview. And so I was writing a newsletter and
with the same general theme as a podcast, but they were not connected in any way. And now I realized after doing a survey of the audience that there are a lot of people that don't like to listen to podcasts. They're probably not the people listening to us talk right now, though maybe they're on YouTube. But there are a lot of people who like the same content but want to read it. So I was like, oh, well, if I'm going to do a bunch of research or interview someone to learn a lot about a thing, I should probably take that information and put it in other places. So now I'm spending a lot of my time thinking about
Well, there's some people that like to watch five minute videos. So what would a conversation with someone talking about vacation homes look like? Well, maybe it's, here's everything you need to know about, you know, luxury rentals. Here's everything you need to know about timeshares, breaking it into a bunch of five different or five minute segments. So now I spend a lot of time trying to think about if I'm going to do all this research on one topic, how do I make sure that all of that information makes it to all the people that could benefit from it?
which means it's got to take different formats. And so that's a lot because I'm not a professional YouTuber or newsletter writer. None of what I'm doing is something I have kind of background in. Yeah, that's pretty cool. Yeah, I think it'll definitely be interesting to see how your journey evolves as a full-time podcaster now. Yeah. I guess the final thing I want to talk about is you have these principles for life optimization that I wonder if we can just kind of go through briefly.
and just kind of riff on a little bit. What's going on there? Yeah, so I think a lot of people have always asked me, like, why are you this way? Like, you know, most people don't, you know, walk into a restaurant and they're like, how do you get a deal here? And to be honest, I don't think there are a lot of deals at restaurants, so I wouldn't worry there. But like, in general, I'm always like, what is the way to get a better outcome here? And most people don't do that. So...
I was trying to figure out why. And someone had actually told me, they said, oh, you should write a book. And I was like, well, why should I write a book? And they're like, well, not everyone likes to listen to podcasts every week. Some people are like, I just want the version of everything you've learned, but with a finish line. And a newsletter and a podcast, they don't have a finish line. I was like, well, what would the book be about? Because it wouldn't be about something that changes. Like it's not going to be about travel hacks because those change over time. And you're not going to read that book 10 years later. Some of the principles of money are there, but I feel like my thing is more about optimizing lots of things.
And then I was connected with this woman and I,
She was basically referred to me as someone who is really great at helping people figure out their unique perspective on life, but actually turn it into like a thing, whether that's a framework, a set of principles or something. So we worked together for five sessions. And at the end, I actually came out with like what in hindsight seems so obvious to me, but like actual principles that are, I think, what allow me to live this kind of optimized life.
So number one was like conventional wisdom sucks. And for anyone listening, these are not final. I won't, I won't hit all nine of them, but, uh, it's something I'm working on and I think will probably be the foundation for either a really long post, a series of podcasts, a book, something nice. But, uh,
Yeah, one was conventional wisdom sucks. Like every time I'm meeting someone and someone says, oh, like this is how we should do it. I'm like, is it how we should do it? Like, why should we assume that because this thing is how we've always done it, it's what we should be doing? Maybe there's a better way to do it. You think that we should, in London, everyone, no one eats lunch before noon.
So I asked a few people and they're like, well, yeah, you got to change your schedule for your kids because things don't open until noon. It's like, well, no, like if you dig around, there are places that do open at 11 and there's places that, you know, so like I wasn't just going to take anything at face value. It can be quite annoying, I think, to be my manager or friend sometimes because someone's like, oh, this is how we should do it. I'm like, well, is it really how we should like, you know, I have to learn to dial that down. So that was one. I think questioning the outcome you want was another big one. I've met people that say, okay,
You know, I need more money. I'm like, why do you need more money? They're like, well, I need more money so that I can retire a little earlier. Why do you want to retire earlier? Well, I want to spend more time with my kids.
Right now I feel like I don't see them that much, but if I could retire earlier, yeah, they'll be a little older, but I'll get to spend more time with them. It's like, well, if you want to spend more time with them, what if you could spend it now? Oh, I can't spend it now because I have this job. It's like, well, the thing you really want might be to find a way to work a job that has more flexibility. And maybe you don't actually care about retiring five years early. Maybe you actually care about having flexibility now.
But we started this whole conversation about you wanting more money. So in product management, there's this thing called the five whys where a customer says, oh, I want this thing. And you're like, why? And they're like, well, this. And you're like, why? And you just keep asking why until you get to the point like, oh, that's what your unmet need really is. And I think we might do this as product managers doing research, but we don't do it with ourselves.
So you're asking, why do you want this thing? Dig, dig, dig deeper to figure out if maybe the thing that you actually wanted is something completely different. And that allows you to change your perspective. Sick. Please keep going. This is great. This one, I encourage anyone listening to shoot me an email, chris at all the hacks.com. I don't have a catchy name for this one, but it's basically structured information gathering. So I need to come up with a name, but yeah,
Let's take daycare or not daycare activities as an example for your kids. So my wife and I were thinking, gosh, we met someone and their kids are age and their kid goes to gymnastics class once a week. Should our kid go to gymnastics class? And I was like, well, before we just decide gymnastics class, what are all of the classes they could go to? Like, let's go build a notion page for all this stuff and start to categorize everything. And.
My initial instinct was like, let's just start searching. But what I've become really good at over time is let's think about what I want to collect when I'm doing the searching. So I made like a simple table on a notion page that was like, okay, if I'm going to go search for all this stuff, let's, let's figure out like, when are the classes? What's the age range of the classes? How much do they cost? You know, like how, how frequently do they happen? How, what do you have to commit to? Like, you know, trying to think of that so that I'm not one wasting my time. Hmm.
Which I imagine had I not done that, I would have gone and I would have come up with this list. And then my wife and I would have sat down and be like, oh, yeah, there's this one class. She's like, oh, okay, well...
How much does it cost? Oh, let me go look it up. And now we're wasting our time gathering all this other information or we're punting and saying, well, let's talk about it next week. When the goal was to actually go and decide what the class we want our daughter to take is. And so if we want to be optimized with our time and with the outcome, let's have a little more intentionality with how we collect information. And in many cases, this is just like, think of the, you know, cells in a table that you want to fill out in advance. But I think by doing that, it changes what you collect and
And it lets you process that information a little more easily, or at least a little bit more efficiently after the fact. Dude, that's such a good, that's so good. I've been, for the last year and a half of living in London, I've been thinking every week, I should join a kickboxing class.
And I've never once sat down with a Notion table to just think, "Okay, let me actually look at these options." Because I'm also not sure kickboxing versus boxing, but some kind of combat sport. But then I look at a website and I'm like, "Oh, I've got to ring them up." I'll do it next week. And I've been pushing this off next week, next month, literally for the last 18 months. And all it would take is to just make a table and just be like, "Let me actually find out all the kickboxing and boxing classes in and around my area with the time, the date, the price. Good." And then I can make a decision. Yeah.
Yeah. And you could probably just thinking from the deal standpoint, I bet one of them probably has like a intro offer where they're like first class free. Yeah. If you found the one you wanted, I bet you could email them and say, hey, I'm thinking about joining a kickboxing gym. This other kickboxing gym offers a first class free. I'd really like to try out your gym. I bet they'd match that offer. Yeah. Maybe you can go to seven kickboxing classes for free. Yeah. Just try all seven of them. See which one I like. So good. So, yeah. So I think the one that's been the hardest for me is knowing when to stop. Yeah.
And I think it's become something that I've gotten much better at, but at the beginning was really hard. So it's like, now let's go back to a trip that we took to Greece. And we were like, oh, you know, we're going. It was our first trip we took without children a couple year, year and a half ago. We were like, we want to stay in a nice place. We narrowed it down to three places.
And we had our notion table. And now we're like, how do we pick? And I think we probably went too far. We were like, ooh, let's try to imagine what the rooms are laid out. Like we just went down. Any one of those hotels would have been fine. We've now gotten to a point where both personally and with my wife, we're able to look at each other and be like, should we keep going? Like we have these mental moments where we're like, did we optimize enough such that we'd have more value figuring something else in our life to spend time on than continuing here?
So I think learning both practical ways to do that, which is just like literally you could set a timer. Like we're going to talk about where we should stay and 20 minutes in, we're going to stop and ask ourselves, do we need to keep going or can we just pick? Yeah. Um,
A great example, Patrick McGinnis, who is the guy who coined the term FOMO, his thing to me was he's like, if it's an unimportant decision and you wear a watch, which I don't, but let's pretend I do, look at your watch and be like, okay, if you narrow it to two choices, it's like if the second hand is on the left, do that one. If it's on the right, do that one. Like find whatever the easy, simple way is to make a decision. The less important the decision, the easier it is.
I don't trust Wirecutter.
What are the other things the Wirecutter looked at? Is there one down there where they were like, we didn't review this one yet, but it looks promising. Maybe I should go build my own. It seems so easy for me to process stuff for other people. If you have someone that's like that in that area of your life, maybe just ask them. If you're stuck. I have a few things like that or ways to get unstuck to stop going too far down the optimization rabbit hole. Solid.
So I don't know. Those are a few pieces of these kind of principles for living an optimized life. And people can check out the podcast to find out when more of these principles will drop. Come subscribe and I'll share them as they develop. Final question. Productivity. What are your hacks for productivity? I think outsourcing things you don't love is like a great one. So we already talked about meals. If you don't love cleaning your house, there's an option. You don't love doing your laundry, there's an option.
You do love doing your laundry, but you spend all weekend doing it. Try to fit it in during the week. I feel like there's a lot of times where if you're working from home, especially if you're not, this is a lot harder, but this is a, like a simple productivity thing. You always want to make sure you're home for changing the laundry. So it doesn't sit in the, you know, in the wet, wet, wet washing machine forever.
But you could just fit that in usually to your work day. So instead of trying to do it on a Saturday or a Sunday when you're like, okay, well, I've got to be home for three hours to do laundry. Maybe you just do it in the work day and like slip in in between a meeting to change the laundry over. So that was a good one. I can't remember where I picked that one up. On the computer, I'm a big fan of Alfred. I'm a big fan of Superhuman and like any app. I've recently, I don't know if this is productivity or not, but I've been playing with a new thing that's not out yet called Rewind.
Rewind. I think it's rewind.ai. And I can't tell if this is like the most insane privacy violation in the world or the best tool I've ever used. But I think one of the things that saves me a lot of time, so in the bucket of productivity, is not having to document everything. So I loved how I was talking to Tiago Forte, whose book I also see on your wall. And he's like, you know, you think I'm building the second brain, but
And I'm putting everything in it. I'm putting like one or two notes a day in it. I'm not trying to put everything in it. And so one of my challenges is like I spend a lot of time collecting information and doing research, but I feel like I have to save it all. So what Rewind does is it records everything you do on your computer. I'm pretty sure I think it also records your microphone. Like it records everything.
And if you're on a website, you're in an app, it not only records it, but it OCRs it and recognizes the text. Oh, funny. So just for fun, I started using this and I searched tea yesterday. And it pulled up the Google Spreadsheets page for a London itinerary where I had go to the afternoon tea. It pulled up a Wikipedia page I was looking at about something around tea. It pulled up all the pages of the sites. I was like, wow, how...
How many times, and maybe this is just me, but have I like tried to go find this information or tried to figure out how to save it or tried to search for it? It took me so much time trying to find this thing. So it's basically like imagine if you could search through everything you've done on your computer. Yeah. And conceivably, I believe that it's also recording audio. So it could search through the audio of what you've said, the websites you visited, the things you've written. Yeah.
I honestly don't think I've done, you know, it's kind of like early beta invite from friends, but I got to think more about the privacy side of it. Like, yeah, that sounds pretty cool. I believe it's all local. So it's not, it's not getting web processed. You're not like uploading your audio files. Yeah. I saw this on product on a few weeks, months, months ago when it came out. Damn, that sounds sick. So I don't know if that's really, I struggle to decide whether that's productivity or not, but I'm going to put it there. Love it. That's so good.
Amazing. All right, Chris, thank you so much. It's been absolutely wonderful. It's midnight now, so I think it's a good time to end this. And we can definitely do a part two when I come visit the US at some point in the new year. I would love to do that. All right. Any final, any requests, any asks of the audience while we're here? People who might have listened to the last two hours and 15 minutes of this podcast. Okay, I'm going to leave you with two things. Nice. I'm going to give and then I'm going to ask. So first...
When you're buying anything, I love getting a deal. If you haven't gotten that so far, I don't know. If you're shopping online, I'll just share like a fun thing that I do. So I'm going online, I'm trying to buy something.
Step one, I always make sure that if there's some shopping portal like Rakuten or anything on Cashback Monitor that there's some way to get cash back for shopping online. I'll do that. Okay. I'm also using whatever site to find promo codes. I find that's really hard. It doesn't always work that much anymore. But the few other things that I'll do, which are fun, I'll search online for coupons that I could buy. So every now and then you'll find, you know, in the States I do it on Craigslist.
some classified sites, even just sometimes searching, there are people who like find these coupons and they actually just sell them. But if you're spending $1,000 and you can buy, you know, a 15% off coupon that you couldn't get just searching for promo codes, that's one. I love asking live chat, similar to the style of Airbnb discounts. I'll just be like, hey, I'm on your website, would love a discount. I would say 50% of the time, someone's like, here's a discount. I'm
50% they're like, nope, we can't offer you a discount. One time someone said, I can't offer you a discount, but we do have this great referral thing that if you can find anyone that can refer you, you'll get a discount. And I just go to search.twitter.com and I search for the name of the product and use my discount or something and then I find someone's referral code and they're going to get a great referral, so that's great for them. And then...
Another fun version of this. So I'm like always trying to figure out how to get like the best deal. It feels so satisfying. Even if I just save like $5, I just feel really good. And it's probably a waste of time and anti-productivity. But gosh, knowing you got the best deal out there. The last one is, let's say you have a credit card that earns you some type of bonus on something, whether that's at Amazon or whether that's at grocery stores or office supply stores. There are so many places these days that sell gift cards. Hmm.
So if I'm going to go buy something from Home Depot, you know, like a, I don't even know what you kind of call it, a home improvement store in the U.S., I'll go and I'll first search for a coupon. I know there's this website, savendeals.com, that sells Home Depot coupons. They also sell like crate and barrel coupons and all this stuff. So I'll go buy the coupon. I'll go through the cashback portal. But I don't have a credit card that gives me four or five points per dollar on Home Depot. Right.
So I'll go to the grocery store or I'll go to Amazon where I've got an Amazon card and I'll just buy Home Depot gift cards. And I'll get the 5% cash back on Amazon for my Amazon card or I'll get the four points per dollar at the grocery store. Nice. And then I'll buy the thing I want from Home Depot with a Home Depot gift card. So I'd say like if you're shopping online, there's more than one way to get a deal. So I'll leave you with that. If you're still here and you like upgrading your life, your money, your travel, you want more deals, you want all the hacks,
check out my show. You're listening to podcast. It's probably easy to find. Just search all the hacks. Or if you prefer email, I don't know why you're here listening to podcast, but you can go to all the hacks.com slash email. Chris, thank you so much. Thanks for having me.
All right, so that's it for this week's episode of Deep Dive. Thank you so much for watching or listening. All the links and resources that we mentioned in the podcast are gonna be linked down in the video description or in the show notes, depending on where you're watching or listening to this. If you're listening to this on a podcast platform, then do please leave us a review on the iTunes store. It really helps other people discover the podcast. Or if you're watching this in full HD or 4K on YouTube, then you can leave a comment down below and ask any questions or any insights or any thoughts about the episode. That would be awesome. And if you enjoyed this episode, you might like to check out this episode here as well, which links in with some of the stuff that we talked about in the episode.
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