Dave Asprey: Silicon Valley to Bulletproof — A Biohacking Journey | E135
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There's something called rejection therapy. It's my most powerful piece of advice. If you're afraid of hearing no, you're going to have a hard time selling because you may have to ask more than one time. And so what you do is you make a goal every day for 30 days, you're going to ask for unreasonable things until you get a no. And it feels really scary, but you'll be amazed.

how many times people say yes. And by the end of 30 days, you'll be sitting there going, I can't think of anything to ask for that people won't say yes to. And it's getting over that fear. At first, it feels like no one loves me, like I'm going to die. They said, no, something must be wrong with me. And you want to be able to sell it. You have to be able to hear a no. Welcome to In Search of Excellence, where we meet entrepreneurs, CEOs, entertainers, athletes, motivational speakers, and trailblazers of excellence with incredible stories from all walks of life.

My name is Randall Kaplan. I'm a serial entrepreneur, venture capitalist, and the host of The Search of Excellence, which I started to motivate and inspire us to achieve excellence in all areas of our lives. My guest today is Dave Asprey. Dave is a serial entrepreneur, lifestyle guru, best-selling author, and is widely considered the founder of the biohacking movement.

He started several companies, including the food and supplement company Bulletproof Coffee, Bulletproof 360, Danger Coffee, and Upgrade Labs. He was also a pioneer in e-commerce and was the first person to ever sell something on the Internet. Dave is also a four times New York Times bestselling author. His books include Superhuman, Fastest Way, Smarter, Not Harder, Bulletproof Diet, and Game Changers.

Dave is also the host of the Top 100 podcast, The Human Upgrade, which has been downloaded more than 500 million times. And he is the ex-chairman of the anti-aging nonprofit organization called Silicon Valley Institute. Dave, welcome to In Search of Excellence.

Thanks for being on my show. Randall, it's a pleasure. I love getting to talk about entrepreneurship. It's one of my favorite things. It's how we change the world. We've got some great things to talk about. I want to start with family. You were born and raised in Albuquerque, New Mexico. I was. The gene runs in your family. Tell us about your grandmother, Los Alamos-

laboratory and then the one living in Roswell, New Mexico, and your parents, both engineers as well. Tell us about the family influence and what influence did your parents have on you? Well, my father's side of the family, my grandfather wrote

And he wrote for Encyclopedia Britannica underneath what is chemistry. And he was a renowned physical chemist who helped to figure out how to purify plutonium the same way we do for reactors today. And my grandmother was a PhD nuclear engineer. And they met on the Manhattan Project and spent their lives figuring out how to do clean nuclear power. So a little bit nerd in the family. I think my grandmother was very clearly Asperger's. In fact, so does she. And then my dad worked for a national laboratory as well.

And on my mom's side of the family, it's from Roswell. So I've got nuclear stuff on one side and aliens on the other. And that explains a lot. So tell us about the influence your parents had on you. They were both engineers. Did watching them work in that field say, one day I want to be an engineer myself? Well...

There was definitely pressure. I think all my dad's siblings are in hard sciences. And it was one of those, if you want to be loved, you need to be right. So there's a really profound skepticism, almost cynicism in the family, especially about anything natural or alternative, which is kind of funny because my grandfather was a master gardener and a Boy Scout leader. And

and, you know, spent a lot of time in nature, yet anything at all spiritual was just not worthy. And they would, I would say, actively make fun of anyone who would, you know, consider anything spiritual. And I certainly absorbed that. I studied computer science and information systems. My undergrad degree had a concentration in AI. So I was early in that stuff.

And that was an influence. I remember I told my dad when I was 16, I said, you know, I think I want to do marketing. It sounds really interesting. He goes, if you want to do marketing, just go market. You need to go to college for that. And you have to go to college. So I'm not going to help unless you study engineering or science.

So I started out studying electrical engineering. I realized that physics was an absolutely evil course to weed people out. But if I studied computer science, I didn't have to take physics till later. Done. So that was why I ended up in fields. I became a computer hacker early on. Let's back up because I want to know what you were like as a kid. Tell us about five to 12 before we get to your teen years.

I had Asperger's syndrome. I grew up in a basement that had toxic mold, which is one of the causes for that kind of a thing. I was constantly challenged with health things. I had sinus infections or strep throat every month. I was on antibiotics almost every month for 15 years. Lots of brain fog.

I was a relatively good student in terms of grades, but man, there was a lot of bullying. And when you're the biggest guy and you have no social skills, it's, it goes double because the little guys have Napoleon complex and always want to get in a fight with a big guy. So I think I've been in like a hundred fights and I didn't lose any of them, but I never started one with the first punch. I might've started them verbally, but,

but that doesn't, it doesn't do good things for you to be bullied that much. I would have bullied stuttered my whole life. I had a little stutter too. I used to have the facial scrunching, ODD and OCD making all the contortions. Yeah. I'll scrunch my nose or I do this like stimming thing with my fingers. And I had ADHD and mostly the Asperger's is tough because it's just a mystery. Like why people do what they do. It doesn't make any sense because it's,

Your brain doesn't have enough energy and enough signal from the world to really pay attention to that stuff. So I wouldn't know the names of more than two or three people in my class by the end of the year because my brain just couldn't do it. Being bullied had a huge impact on me. I said, one day I'm going to not stutter. I'm going to go through speech therapy and do all the time and do all the work. And it was...

thousands of hours of work, right? To learn how to speak. And, but it had a profound impact on me and my motivation. Did it motivate you and say one day, gosh, this is terrible, it's cruel. Did you come home from school crying and say, hey, one day I'm not going to be bullied. I'm going to be something and make something of myself? No.

Uh, I didn't like being bullied. My dad had been also profoundly bullied. Um, he grew up in a small town. He was the only white family in New Mexico. So he literally had gangs coming after him. And so he said, well, Dave, here's what you need to know.

It doesn't matter if they beat you up. As long as you hurt them enough, they won't come back. All right. So that was my, that was my thing. So I just made sure that I always got a few good punches in and it just so happens because physics like I'm 50 or 70 pounds heavier than these guys. So of course I was one of the fights, but it's terrifying because when you're a kid, it feels like you're going to die in a fight until you just get over it and realize that's not real. So I don't,

I don't think that I was successful because I was bullied. And I've had a lot of clients come through my personal development program with neuroscience where they'll say exactly, oh my gosh, I started my career because I just wanted to prove something to someone. I wanted to prove something to myself, not to others. And I just remember we were building the early internet. This is going to change the world. I was just excited. I could see the future happening and I just wanted to make it. It was this deep curiosity.

I was also really profoundly angry probably as a result of the bullying, but it didn't turn into motivation. And what I learned is that anger is a great fuel, it's a great spark to light a fire. But if you use it as your fuel, it will burn you up, it'll eat you up. So it's fine to be pissed off about a problem or pissed off about a situation. I'm going to change it. But if that continues to be your motivation, it's no good. But for me, I was profoundly unhappy and I didn't know why.

And so I said, all right, let's try making a ton of money. That was my focus. I'm going to be rich because therefore I'll be happy. When I'm 26, I made $6 million. These were pre Biden dollars. That was real money. We're going to get to the, we're going to get to all the money stuff in a little bit. So, but like the motivation, it was, it was, I wanted to be happy and I wanted freedom. It wasn't that I wanted to show someone I was good enough. I don't think that was in there.

Did you come home from school some days saying, hey, mom, or crying and people saying I'm fat or have acne? I might have cried a little bit when I was in third grade or something, but after that, I'd just come home and say, I will punch them. I was pretty angry.

So you go to UCSB, University of California, Santa Barbara. Yeah. And you created something and made a t-shirt. Talk to us about the t-shirt and how you were the first person ever to sell something on the internet. Now, some people hear that and say, that's not real. The internet was very small back then. We didn't have web browsers. What year was this? This would have been 1993, 1992. Okay.

There was something called Usenet. It was like Reddit, but text only. And it was very small. So you could actually read everything on Usenet in the very early days of the internet. And I was in the alt.drugs.caffeine news group. And I was like, I need to start a business because I'm trying to pay for my tuition. I'm scooping ice cream at Baskin Robbins. I'm putting auto parts in boxes during summers. And I'm trying to pay for my tuition. And

And I was like, if I start a business, I can do this. So my main business was to sell Halloween t-shirts. It's a giant party at UCSB. So I'd make 10 or 15 grand in a week selling t-shirts. I'd hire salespeople to go around and it was a whole big deal. I know t-shirts. Why don't I make one for these people on Newsnet?

And so I went in and I ended up selling t-shirts to 16 countries. And a month or two later, a Rutgers professor comes online and says, and one of the internet marketing groups, no one's ever going to make money on the internet. And I'm like, Oh yeah, Mr. Mr. Ivy league. I'm already doing it. And the next day the Miami Herald called. And then I was in entrepreneur magazine with my photo and I'm 23 and I'm

Fast forward years later, people are like, "You weren't fat." I go, "Here's a picture from an entrepreneur. I'm pretty sure I'm fat." You can't argue with that. The day after I did that, a company called Virtual Vineyards sold the first wine online. But as far as I could tell from all historical records and my own being there, this was the first product ever sold. But e-commerce wasn't a name. We had invented the name e-commerce.

So a group called Meta, it was an early research group, came up with a name for e-commerce. I was in the room when they were trying to figure out what do we call this? And e-commerce was the name that eventually came out of it. So at the time, I'm just trying to have good food and pay my rent and my tuition. And eventually, I just shut it down because...

It was too much work to put t-shirts and boxes and bags and send them all over the world. I didn't have the concept of hiring people or even accepting help. My belief was I had to do everything on my own. And I kind of laugh because I wrote an article comparing the first two web browsers to each other when I became an internet journalist. And so Marc-Andres and I are the same age.

And he writes the first web browser, but he calls Jim Clark from Sun and says, will you teach me? And I'm like, I'll do it all by myself. Mark's a multibillionaire. I'm not. I'm not jealous. We're both doing great. But he just had the wisdom to understand that people wanted to help. It took me a lot longer to get that message. So what's your advice to all the entrepreneurs out there, doesn't matter the age, who are afraid to reach out for help? Number one, you don't owe someone anything.

If you ask for their help, that's not how it works. The people who want to help, they've suffered a lot and they just want you to not suffer the way they did.

And understanding that you can just say thank you. That's what they want. So I help a lot of entrepreneurs and it's because I want to help. And they're actually doing me a favor by allowing me to help them. Because acts of service are one of the things that make you younger. They put you in a flow state. So receiving isn't about transactional stuff. It's about someone wanting to see you succeed.

You have a lot of followers, though. You have over a million followers on Instagram and on a whole bunch of other platforms as well. LinkedIn. I have 30-something thousand followers on LinkedIn, and I get every day, I'm interested, I'm an entrepreneur, I'm in school, do you have 15 minutes for coffee? I can't do it. I work 70 hours a week. I'm running five different companies at the same time. I'm writing a book called Extreme Preparation. But I will meet with everybody who earns the meeting.

Mm-hmm. Tell us about what someone has to do to get a one-on-one meeting with you because you can't meet with everyone who asks. It's pretty tough to get a one-on-one meeting with me. You have to have a reason and you're going to go through my team. So I don't usually answer cold calls like that. Some of the more interesting ones are people go to an event where I am and they'll say, hey, I've got this thing. Here it is. And they'll just talk to me about it. And what I've learned over time is to kind of ignore what the thing is.

And so who's the person and having worked for a venture capital firm and been an angel investor and advising lots of startups and the Apollo group, I, I,

I look at the person and the best investors are saying, well, who's the team? Because the team is going to change what they do if it's not a good fit. But if you have a great idea and a team of people who aren't good people, it's not good. So my big learning over the last 30 years has been just discernment. Like, how do you know that they're a good person?

And the more power, the more fame, the more wealth you have, the more you'll attract narcissists and sociopaths to you. This is why celebrities are also weird because you just don't know who to trust. Right. And it, it creates a lot of psychological dissonance, a lot of stress until you just learn discernment.

Let's go back to one of the things we have in common. We're going to talk about a lot more today, but I sold t-shirts in college as well, but not online door to door. I went to Michigan, go blue, greatest place on earth. And I saw someone else doing it. And I thought, gosh, you know, I can do that. So I took $500 of my Burmese money and

And as you said, there's no online. You couldn't look up where to get t-shirts. You know, today there's a hundred places. You can tell the cotton, you can see the reviews. So I'm in the yellow pages. People don't even know what that is. And I call someone close. I said, all right, I want a cotton t-shirts.

Short sleeve, $5. Long sleeve, $6. Solo for $18. I went door to door. I went to every single door. That's totally what I did. I mean, it's a great margin, right? For an extra dollar, the margin was huge. I was making $50 or $100 an hour compared to $4.25 scooping ice cream. It was so much better. Yeah. Yeah. So...

Have you used cold calling as I did going door to door in your career to get successful? And what's your advice to people who are afraid to reach out to somebody the same way they're afraid to reach out to a mentor? There's something called rejection therapy. I did a podcast on it a while ago, and it's my most powerful piece of advice for that. If you're afraid of hearing no, you're going to have a hard time selling because you may have to ask more than one time.

And so what you do is you make a goal every day for 30 days, you're going to ask for unreasonable things until you get a no. And it feels really scary, but you'll be amazed at how many times people say yes. And by the end of 30 days, you'll be sitting there going, I can't think of anything to ask for that people won't say yes to. And it's getting over that fear. At first, it feels like no one loves me. Like I'm going to die. They said, no, something must be wrong with me. And you want to be able to sell it. You have to be able to hear a no.

So my dad told me something a long time ago, and he said it in a context I'm not going to say on the show. So we'll... A dating context. He said it in a dating context. He went a little further than just a date, but we'll use dating as an example. He said you go up to a woman.

who you don't know and say i'd like to take you on a date and she says no the first 99 times you know you just crash you go back there and say man this really it's terrible but when the 100th person says yes you forget about the other 99. it's totally true and one of the things is look

Some people like tacos. Some people like Thai. And if you're a taco and you say, hey, you want to go on a date? And they say, no, it's not because there's anything wrong with you. It's because they like Thai food instead of tacos. So we have our own preferences. We internalize no's as being something is wrong with us deeply. It just means they didn't want it. Or it means that you did not ask. I want to go back to college again. And you started at UCSB and you graduated from a different university. Yeah.

with a degree in some form of AI. And we talk about what that means today, what it meant back then is just something completely different. So can you explain exactly what you did back then? And is it any comparison to the AI that we know today?

We, well, I studied computer science for four years and I got really frustrated. I'm running an internet business. We've done nothing with computers that is useful. Like write code, did solve these esoteric problems. And it was just too cerebral. Like tell me how to run a business with computers. Tell me to do something with

And I left UCSB in part because my GPA wasn't very good. And I got a degree in computer information systems with a concentration in decision support systems. And it was AI, but we weren't allowed to call it AI because they believed it would never come true.

So we studied all of the things you would study for AI, but we didn't have the techniques we have today, where you basically take the output of a system, put it back into the input, and then it self-learns. But we did study how to use software to make software and how to increase human decision-making capacity. So it would have had elements of library science, how do you organize information, and then how do you make it so information is usable?

And to me, I mean, I have an enormous amount of information about longevity and cognitive enhancements, human performance, but how do you make it usable? How do you make it teachable? How do you make it actionable? So I've been a tech guy, uh, you know, at sizable tech companies for most of my career. And that, that training about how do you make it useful? It's just been

been transformative, but it wasn't the same AI techniques we have today. But the thinking about what will we do with AI, that's what I learned. Give us all a sense of, and again, my demographic for the show, the primary is 18 to 39, and then we go 39 to 49, et cetera, et cetera. So let's simplify it for people. So what kind of computing power

What are we talking about when you graduate college? And what's the multiple of the computing power that we have today? In that span of 20, 25 years, how far have we come? It has to be billions to trillions times more compute capacity now. The iPhone that I'm carrying has more power than the entire $25 million computer science lab that was full of SGI computers that we worked with. Probably more than supercomputers back in the day. Oh, much more. Yeah.

Which, for those people who don't know, tell people what that looked like. There were supercomputers the size of a giant room. And in fact, I have the first personal computer ever made. It was Bill Gates and Paul Allen made 2,000 CPM machines. No, this wasn't CPM. What is this? Anyway, I'm forgetting his name. It's in my little museum. And it's funny because...

That computer has less power than a calculator watch and it sold for $5,000. And I bought that because when my mom was pregnant with me, she worked for that company. She was the first employee of the company that became Microsoft. She answered phones when she was pregnant. And one of the Microsoft founders bought my crib.

I love that. My first computer was an Apple 2E. Okay. It's a little bit later. If you remember that. I do. And then the one that I actually used was a Macintosh, which I got my freshman year at Michigan. I remember that. There were these wars over, which is better, you know, Microsoft versus Apple and all these things. And I was profoundly in the Microsoft camp just because, I don't know, I hated apples. So that, because as a computer science guy, you couldn't

manipulate them as well. So there was this whole hacker culture that developed that was really beautiful. The cyberpunk thing where hackers weren't about breaking into stuff. It was about how do I take control of something? How do I find the ways around it? And that training is what led me to become a biohacker.

Right. It's hackers. You see a system, but you don't know what's in there, but you want to change its behavior. Well, that's what we do in health. We don't really know what's going on in our bodies, but we use the techniques of systems management in order to change ourselves. So all of that experience where I was in pokedown systems where maybe I shouldn't be or learning how to build those systems directly led to being able to think about health the way I do. We all have seminal moments in our life that really change the trajectory of what we do personally and professionally. Right.

You had one of those when you went to Wharton. First of all, why did you go to Wharton? And then what made you say, gosh, it's time to change?

I'd had a profoundly good career in my 20s. I co-founded a part of Exodus Communications. We grew to be worth $36 billion. The part of the company I founded did $100 million a quarter in revenue. Which part was that? It was the professional services group of the company. Okay. So we built the architecture for Salesforce.com when it was eight guys. And Google came in with two guys and two computers. This was a crazy, amazing time in tech history.

And we have the data centers. And so we'd run all these systems. It was the funnest thing ever. But you asked me a question there, but I got sidetracked. What were you? About Wharton. What was the seminal moment where you said, it's time to change? So I started doing strategic planning instead of just the hardcore tech stuff. And they invited me to attend board meetings. I'm 26 years old. I'm not allowed to speak in board meetings, but I attend all the senior leadership meetings, even though I'm not a VP because I'm the guy who knows how everything works.

And I realized these people are insane. And I read 48 laws of power by Robert Green. I've had the honor of interviewing a couple of times and it just changed my whole view. I'm like, oh my God, there's a whole different operating system for humans that I'm not aware of. It's not the nerd engineer culture. It's power culture. So suddenly it was like someone lifted a veil. And I worked for a guy from Harvard named Peter Fornbach, who is just such a great leader. And he showed me this stuff and he said, Dave, you might consider doing this.

There was a dot-com crash. I said, all right, businesses are all drying up. I'm going to go to Wharton. And it was mostly because Peter suggested it. And I already had a job that most MBAs would kill for, running strategy for a big company. I just wanted partly the name and the network and the knowledge. It was just something I hadn't done. And maybe part of me, my family was

like academically a little bit blue collar you could say it's like they went to you know ucs and california states and there was sort of like those ivy league people i'm like i guess i'm going to be ivy league so i went to wharton and i had a profoundly good time and really learned some things about leadership and i was failing out of my classes though and i was starting to think maybe i'm actually dumb because i'm trying really hard but i just i'm failing on these tests so

I already knew that I had some weird cognitive dysfunction. I had chronic fatigue syndrome, serious brain fog, big dips in energy. I tried all the different diets. I was taking smart drugs. And I went and got a brain scan from Dr. Daniel Amen, who's now a good friend of mine, his board of directors. I saw him actually two days before we filmed this. He's going to be on my show as well. I can't wait to have him. He's a great human being. And his point was,

It's a hardware problem. So we got my brain scan back. And I remember the psychiatrist looked at me and he said, oh, God, Tech Bro wants Adderall. I know this type. And when I came back from my brain scan, he just looked at me. I'll never forget this. He says, Dave, inside your brain is total chaos. I don't know how you're standing here in front of me. You have the best camouflage I've ever seen.

And I started taking modafinil, which really, really helped. And it was that day, though, that I realized I don't have a lack of trying or a moral failing anymore.

I have a hardware problem and I can fix that. I can change that. And there would be no biohacking if it wasn't for Daniel Heyman, because I'm like, oh, let's fix the hardware. So then the software will work better. And then I can edit the software. And what a, what a lesson that was. And it was partly medication, but it was just understanding. It's not that I'm not trying. It's that I'm doing something wrong. That's not supporting my brain.

I want to go back and we're going to go through your tech career. All right. We're going to talk about some similarities we have now that you may find very surprising. When I started my career as a lawyer in 1993, went to Northwestern. I laid off five and a half weeks after moving to LA and $3,000 in the bank. I was going to wait tables again. I'd waited at Chi Chi's during law school, had bad groceries in high school at Kroger and was worried about my career. So

So I ended up getting a job in Costa Mesa, which I never heard of. I'm from Los Angeles. I leave my house at 530 in the morning. I say Suge Knight three mornings a week at the bagel store when it opened. So I was couldn't wait for the hot bagels. Took me 90 minutes to get to work minimum. He was rolling in, had this Ford Bronco, by the way.

You know, the cool ones, the old ones. And he's got the music blaring in the neighborhood. He had a bodyguard. He's huge. The bodyguard is huge. So we had a nodding relationship. But after six months of that commute, I was working. I'd leave at 530, come over at 11 o'clock every night, six days a week. It was not good. I had no friends here. I knew nobody out here. And so I went to the managing partner of the firm in Los Angeles and said, I want to move. He said, no, you got to move down to Costa Mesa. I wasn't doing that.

Three jobs in eight months. Wrote letters to CEOs using LexisNexis. Very detailed. 300 letters. Got 80 meetings. Eli Broad at Sun America, who is a Ford 400 member, hired me assistant to the chairman. So now I've gone from 10 miles deep to 10 miles up on my 27th birthday. Wow. Great job. Yeah. Stock options.

Five-year grant, I got three vested, and then I left to start a technology company, Akamai Technologies, which you know well. I know very well. You guys were brutal, by the way. Well, I mean, we're going to talk about Exodus now in a second. And the option thing as well. But I left $2 million of non-vested equity on the table. I had another two years to go. All I had to do was sit there.

and do nothing else. And I was paying for my own wedding, engaged, and I left. Three months later, Eli sells a company, AIG full vesting event. We're going to talk about your full vesting event in a minute as well. And so I left to start a company, unproven, untested technology. We were going to revolutionize the way that information was sent on the net, which is exactly what we did. But we had no funding, no

no CEO, and I was commuting to Boston every week. And they said, all right, we've got this hardware. Now we need to put it somewhere. Yes. So Alan Hancock, our old CEO, your old CEO says, we got data centers for you.

And we're going to give you free rack space because you can help us decrease our bandwidth costs, which was your primary cost back then. I was part of the analysis for doing that back then. So, and she didn't quite realize at the time that we were going to cannibalize her business. I knew it, but we really needed the bandwidth. You needed it. So, explain the problem. You guys were selling bandwidth. Yeah. We could lower your cost.

And we were basically charging our customers for the bandwidth. So just talk about in business sometimes, it's not black and white, right? You're going to weigh benefits versus the cost. What were you guys thinking at the time? Because ultimately, it really helped ruin your company, what we were doing. Okay, but talk to us about the difficulty of weighing the pluses and minuses where there's

So levers are going to shift. Let's explain what the business was. So Exodus built the first internet data centers. And what happened was the guys who started Hotmail couldn't buy bandwidth, like T1 lines, fast enough.

Tell people what a T1 line is, a T3 line, and the problem with sending the data. The problem is if you want to run a website back then, you had to run it out of your office. And you had to call the phone company and say, I need a really big pipe to the internet. And they say, we can get you one in six months. I mean, your business is tripling every day and you're stuck. So then you can't do internet business.

So the guys at Hotmail ran into that problem. So it turns out Exodus had a couple of small data centers they'd built. And on a whim, the founder, KB Chandra, said, why don't you just put your computers near our bandwidth? And this ended up...

being a $36 billion market cap business, and we grew to 42 data centers just because we had lots of connections to the internet and we had lots of electricity where you could put your computers. We had big air conditioners. So it's more like a real estate play. It's like a hotel room for your server. And...

The problem was we had to pay a lot to get the connections into our data centers, a huge expense. And then we would resell that bandwidth. And when you guys came in, you said, well, you know, we'll put our computers there for free, which reduced the amount of money we'd spend on bandwidth. But it did mean that basically some of the things we would have sold for bandwidth would go through you guys, but it reduced our costs. We were hitting capacity limits on our bandwidth. So

In fact, you saved us bandwidth. Yeah, you cannibalized some of the business, but you cut our cost of goods a lot. So we were okay to do that. Right. And just to tell people what we're talking about. So the T1 line, think of it like a circle and a tube. And back then and still today, every video file gets broken down into...

bits, ones and twos of codes. And people don't really think about this, but it gets sent, disassembled into a bunch of ones and twos, hundreds of millions of lines of code, basically, and then it shows up on your computer. When there's a big news event or Victoria's Secret fashion show, which we broadcast online, every website would go down because they didn't have the bandwidth. So what people were doing is they were buying these T3 lines and even bigger,

not using the space for when something big happened. And one of our benefits is we solved that problem. It's called the flash crowd problem. And so that was, we could increase your performance speed because what we did is we created a network of servers throughout the world. And so what would happen is that piece of content would get replicated wherever it was in our computers close to the user. So rather than go back

CNN was one of our beta clients, one of our biggest clients. So every video file would go back and forth to their data center in Georgia, Atlanta. And by the way, they had three times more people in the data room than the newsroom making three times as much money. Wow. Which is crazy.

Yeah. Right. And so rather than that video file going back hundreds of millions of times, it was sent if you're in Boston, you get it from a server in Boston much faster. So we could serve it faster, guaranteed online, no downtime. Yeah. And the flashcard problem. But it was interesting because that deal helped make our company. Normally you'd have to pay for Rackspace. Yep. And it's very expensive.

So that was a seminal deal for us in our company. So there's a lot I want to talk about in terms of compensation here. But let's talk about, like you said, you were $36 billion. Your stock went from $90 to $5. I experienced something similar. Our high was $45 billion. It went down to $0.49.

I remember talking to someone about the fact that they should buy Akamai at the time, like a hustle takeover thing, some investment banker, because you guys were just way undervalued. Our market cap was over, it was less than $100 million, got delisted from NASDAQ. It was a NASDAQ small cap. And I'm thinking, oh, God, like I left the company already. I still had a bunch of stock. Thinking, what have I done? So let's talk about that issue. So you could have...

made $6 million. All I had to do was quit and sell all my shares. Right. But you weighed in and said, God, I could make 10 million was your number. Yep. And you had some unvested equity. Yep. And I share similar qualities, right? Didn't sell at all when I could have. And so what were you thinking at the time? Let's explain this. A lot of listeners, I find people under 30 oftentimes don't understand or even value stock options. This is what makes you have life-changing money.

So this is your company. If you negotiate, right, we'll give you a right to purchase the shares for almost nothing. And you only have to use that if the company has, if the stock is worth a lot, right? So this is like a lottery ticket, but if your company does well, it's very likely you could make hundreds of thousands or millions of dollars. In my case, my 3000 shares were worth $6 million, right? That was an outsized win, great timing and all that. Okay.

And you're 26 years old, right? Yeah. It's a ton of money. It was still a ton of money today, but really back then it was a little bit massive. Yeah. It's more like 18 million today. Yeah. And I was just sitting there going, this is amazing. All I have to do is just invest the rest of the time.

And this is one of the problems that entrepreneurs and just all humans have is losing hurts more than it feels good to win. So I could have said, I have gratitude for $6 million. I'm set for life.

But the idea that I might lose an additional four or five million of additional growth. And like, why would this company ever fail? Like, we've changed the world. We've done all this good stuff. And, you know, I'm motivated. And, you know, there was definitely some, I like this word, skullduggery. There were some behind the scenes things where some people became very wealthy at the expense of all the shareholders. And there's a lawsuit over that. But

I wasn't on the list of people who made a ton of money by the company failing, but it got set up so most of the execs would get a $20 million bonus when the company went bankrupt. And magically, it went bankrupt. Who would ever imagine? Yeah.

And that was post Ellen Hancock, by the way, that was the person after her. So it was, it was a time where I was like, how could this happen? I remember we built two six story office buildings. I had an office at the top of them. I spent one day in the office before we went bankrupt. And it was just one of those stunning things. And I look back, what I recommend to people today is if you're in a situation like that, sell half and put it in something safe.

And entrepreneurs like me, we're not about not losing, we're about winning. But having someone on your financial management team whose job is to not lose, then you have the nest egg, you have the fuck you money, and you can do what you want.

Even if it's, I'm going to say just a million dollars, that's a lot of money. But if you could have had 10 million, but you have 1 million safe and you lose the other nine, I've had multiple times in my career where I should have made 800,000 or a million or something. And then it doesn't happen for whatever reason. And usually it doesn't happen because someone else is making money in a way they probably shouldn't. And this is why attorneys are so useful.

I'm sure you meet with a lot of young, hungry entrepreneurs. Many of them are going to be massively successful. The fact that they're meeting with you, there's something about them that you really like. And that means they're probably very good. I've counseled hundreds of people coming through my office and I made similar mistakes to you. I'm still more than fine and I'm very financially comfortable. Right. And I have everything that I need or could want.

It's amazing how many people have the opportunity to take some money off the table, like you said, who don't. What's your advice to every entrepreneur out there who has a chance to take money off the table but keeps thinking, I'm going to get more, I'm going to get more, this is going to be bigger? When I had $6 million in the bank, I looked at a friend of the company and I said, I'll be happy when I have 10. And I know that if I had 10 million, I would have said, I'll be happy when I have 20.

Money doesn't make you happy above about $70,000 a year in income. And there's studies that support that. So...

If you're pursuing happiness, it's a skill independent of money. Money is nice to have. It can help you have freedom and flexibility. It lubricates things. But always having more is a realm of hell in Buddhism. They call it the hungry ghost realm. No matter how much you eat, you're always hungry. So take half of the money, even though you might make $100 million, you don't have $100 million in the bank. If you just get $10 million and put it in the bank,

and you only make $50 million instead of $100 million, you'll be happy. But if, God forbid, you don't make $100 million, you lose everything, you still have $10 million. So once you have enough money that it doesn't matter, play for the big things. But what most of us do when we're young is we're overconfident. We don't understand all the dark figures lurking who are there in a system designed to take your money.

and something unforeseen may happen. And if you just take half of what you made and take it off the table, it'll do well. I tell people all the time, when you're raising venture capital money, you tell them, look, you just gave me a $10 million check. I want to sell you additional shares. I just want to take $2 million off the table. And you say, but my company is going to be worth more later. It doesn't matter. The $2 million you have now is...

is going to buy you flexibility and you fly business class, you're less tired and you'll eat better food and all that. And unless you grew up thinking that way, you're probably not going to do it because I got to leave it all in the company. It's dumb. The thing to do is always take some off every time you have a chance. Just take some off the table and put it in something that's not another startup. Right. By the way, I didn't follow that advice. I still have a hard time with it. I'm going to tell you a story that doesn't apply to just young people. I have a friend, great entrepreneur,

His company went public. I never invested in his company. We just do things a little differently. He lives on the edge and I don't like to live on the edge. I'm more conservative. And we were skiing in Yellowstone Club, which is a very fancy private ski mountain

And we're on the chairlift. This company had gone public a few months before. It had done okay. It went up a little bit. I think the market cap was roughly a billion dollars. Okay. And he told me that if the company hadn't gone public the day I did, they would have had to go bankrupt. Wow. So my wife and I go to his house that night for dinner. He said, come on over. There's a chef. I don't know what the private chef costs. It's during Christmas, probably $3,000. Wow. He flew private there.

I'd call another $150,000. And his wife said to me, Randy, what would you do? His stock was worth around $120, $140 million. I gave him the advice that you just said exactly. I said, I'd take $40 or $50 million right off the table. Now, the public doesn't like when you sell your shares if you're a CEO, but they'll give you one time for family planning purposes. So you get one freebie.

Right. And so I said, when you're done paying taxes, you'll put away $40 million. You got four kids so you can pay for a beautiful house in Los Angeles, a nice house. You know, you could get a beautiful house in Bel Air, which he had for $10 million. Yep. Right. And then he's set for life and doesn't have to worry about it. He didn't do that. So the stock was at 20 bucks and he said it's going to 80. He borrowed money to get there. And I said, you're insane.

The stock, and he explained why and he was so confident, lost their biggest customer. The stock went from $20 to $6 a share. I remember we have a home up in Coeur d'Alene, Idaho. And I used to take the 7 a.m. flight. So I'm sitting there in the airport and I see his wife post something on Instagram.

And it said something weird, cryptic. It said, I wish we had listened. And I'm looking at it. I said, God, that picture looks very familiar. I said, wait a minute. That's a painting in my living room. Oh, wow. And so it said, oh, shit. So I get on the phone. And right as I did that, I read the Wall Street Journal that my friend had got kicked out of the company due to a margin call. Crazy making. So my advice to everybody, it doesn't matter how...

old you are, if you have a chance, especially if you have fuck you money. And again, like you said, I mean, everybody's fuck you number keeps going up as they get older. But take money off the table when you can. Yeah. You have to. You have to. Greed will hurt people badly. It'll hurt people badly. And understand...

You have this operating system in your body that makes things feel bigger or smaller than they are. This is your body manipulating you to survive. And losing money feels really, really bad.

So the idea is if I sell the shares, I'm going to lose this money I could be getting. It's the same system that makes sure you don't starve to death. But if you let that run things and you believe those feelings as being a reflection of reality, you will make terrible financial decisions. So you've got to set that aside and say, all right, I'm going to sell some. And yeah, I might make more. I might make less. But this is real money versus maybe money.

Exodus to Spadera, which was sort of a competitor to what we were doing, but a much smaller company. So we buy you $130 million in stock. Full vesting event for you. Now you've got $6 million you took off the table in that deal, correct? Oh, from Spadera? No, I didn't make any money from Spadera. You didn't make any money from Spadera? No. I didn't have stock options in Spadera.

That was an interesting thing. The CEO at Spadera just had an interesting way of running the company. And I mean, you know, all the back channel stuff that was happening there. One of the things, and this is all okay to talk about now because it's years ago, the CTO at Spadera had figured out a way to know every one of the leads you guys were looking at.

Was it Keynote Metrics? Yeah. So, and unbeknownst to everyone else, he'd come in with a list of leads every day. There were always hot leads. And eventually...

Akamai Castleworth. Yeah. Or Akamai Leeds. Okay. So we were growing rapidly. And then one day, you know, the FBI comes in and there was some way from the computers and all. I think you guys initiated that for illegal computer acumen. It wasn't illegal. Like it was publicly available data. So there was, I think we were spending a million dollars a month on legal fees defending against Akamai. No, it makes sense. You're an attorney.

So you guys were challenging competitors for content distribution. And finally, it looked like we were both beating each other over the head. Like the obvious move was to buy the company. And then Akamai skyrocketed after that. So it was a great exit for the people who had equity. But Ajit, we'll say, didn't do a lot of stock options. And

And that was all right. I was going to Wharton and, you know, other things wasn't my primary focus. But it was really interesting to watch the competitive dynamics. So you guys really played the long game and you used the legal system really effectively. Okay. And to be perfectly clear, I wasn't there anymore. So whenever I write it, oh, there's another acquisition by Akamai. Yeah. So what happened there is there was just a brutal war between the two companies, right?

And it was a lot of it was fought in courtrooms, you know, and trying to invalidate patents and trying to do this. And to his credit, Bajit, the CEO at Speedera,

And I remember I took him in to see a VC once. And they said, well, what kind of value add can we do as VCs? And he was just tired. He goes, because guys, I pitched 500 VCs before I got the last round. And now our numbers are much better. He goes, I don't need your advice. I need your money. And so he was this kind of like, just pitch. He just believed in the company. And he finally did get the sale to happen. And I think the combination of two companies was really good. At some point, you hired a financial advisor. You were doing...

options trading on margin and that didn't go very well so i made about 15 when i was trading i would day trade stock options and i realized i was spending all this time and you get all the dopamine hits of gambling and i was making about 15 a year with a lot of risk and you know it would go up in dollar time like why am i doing this it's one of the reasons i never got into crypto

Like, this is going to be big, but I don't want to be trading crypto because it takes all your time and attention and it doesn't add any real value to your life. It just like, it feels really good. I'm so smart. I picked this one. I picked that one. And so I did do quite well in crypto, but I had other people invest in crypto for me, same as I would do in the stock option. I think, once again, as part of my coaching, I met a lot of young people with money or they're going to come into money. Randy, what do you do? What should I do with my money? And I said, hire financial advisor,

who's been in the business for a while, who's not 30 years old, who has seen the markets go high and low, because if you hire the wrong person, it can really hurt. I've hired two financial advisors at various times. And one of the things that seems like it wouldn't be a problem when you first come into money is managing all that money is a huge pain in the ass. Like there's all these tax things you have to do

The California state tax board wants this, and this other thing wants that, and you have to pay this fee. And you can get in trouble quickly, but you don't know who to hire. So I hired a wealth management company, and they convinced me to

donate my money to my own charity so I would reduce my tax bill a lot and I could use the charity. That's called a CRUD for people that have done a charitable remainder trust. Yeah, except the way this one was set up is two years later they changed the IRS regulations and it wasn't really my money anymore. And I'm like, oh, geez. And that was kind of traumatic. So it turns out there's a lot of sharks in wealth management.

So what I like to do is talk to several friends who, who are wealthy, who have been with wealth managers for several years and had good results and get a really strong referral. Um, because I've, I've definitely hired a few, I'd spent a lot of money on and all they did was overcharge me for legal services or, or, you know, $200 an hour for basic accounting. And you realize, wow, I'm kind of paying a hundred grand a year and they're, they're screwing me.

And I'm with someone I really appreciate now who doesn't do that, but it was my third try to get there. So you can lose a lot of money if you just blindly trust your money managers as well. So there's kind of sharks everywhere. Lots of money just brings out the worst in people.

I did something very similar as well. So I knew at some point that I was going to make a bunch of money. Pre-IPO, the valuation of the company keeps going up and up and up. I'm doing the math. I mean, in every calculation, then we file our public offering. And what I did is I went to a bunch of wealthy friends and I said, who do you use to manage money? And I interviewed all these people.

And everyone had a deck. We beat the S&P 500 and the model back then, they're picking stocks. There's some guru at Morgan Stanley, Goldman Sachs, was picking these stocks. So I figured, all right, I'm going to hire four people. And by the way, this was so crazy because when we filed our document to go public, I remember landing at O'Hare.

I'm driving in and rush hour traffic in the cab. There's no Uber back then. And my cell phone rings. It's a broker at Bear Stearns who read the S1. It had been filed three hours before. Hey, Randy, see what you do and blah, blah, blah, blah, blah. But when people know you have money, they're going to come after you. I made a mistake. So I hired mostly younger teams, 30 years old, MBAs.

people that I would get along with. And I didn't really know how they were charging. They would sell me bonds and, you know, the commission on bonds are hidden. Today you have to disclose them. But back then you buy a bond for a million dollars and there's a $20,000 brokerage fee on the bond, which you can't see. Yep. And there's all this stuff. And if

If you use more than one money manager, they're buying the same thing. And so you get into trouble on something called lost, uh, wash sale rules where you can take the loss of someone else's is buying the stock within a three day period of time. And that was a mess when the market crashed.

Everyone got clobbered more than the S&P 500 lost. And so I thought, okay, you know, it's time to take over. I was financially sophisticated. I was self-taught. And when I took over, I learned to manage my money and really made that a job. And it became sort of a full-time job just getting, you know, I had a venture capital firm and I had stocks and hedge funds and I really had to get it together. But my performance increased substantially more. And as if I had,

someone else managing it. And for me, the lesson was no one manages your money as well and closely as you do. It's totally true. If I didn't start Bulletproof and I managed my money, I could have done really well with it, but I created a lot of value there. And it comes down to what do you want to do?

And I don't want to spend my life managing money. I think it's boring. And there are people who really get off on that and then to them, it's exciting. And so I don't mind paying people well who manage money well. And if they manage it poorly, then I don't work with them very often. And I just, I realized that's not what I want to do with my life.

I want to do other things. And this is the big problem is that you can do better if you do it. I haven't found a way to do it reliably and securely and to take enough of my attention to managing money. And it's cost me greatly, I'm sure. I tell everyone, put all your money in the index. S&P 500. Nobody beats the index over a long period of time. Nobody. Warren Buffett, if you were lucky enough to meet him in

Nebraska, you know, in 1963 when he started, you know, good luck to you, but you're not going to meet the next Warren Buffett. Yep.

Before we got here today, I was wolfing down a burger right across the street. And I said, all right, I'm just curious what Dave's $6 million would be today, S&P 500. And I'm not going to make you sick, but you may know. Well, I got here thinking, oh, shit. So it would be worth $35 million today. And do you know how much time you would have had to spend managing that?

Zero. It would be worth $35 million, except I would have invested right before the dot-com crash. It would take me a long time to climb out of that hole. No, that assumed that on that day, I put the exact date in. Okay, cool. And so it would still be worth $35 million. It's incredible. And this is not how entrepreneurs think. And that's the thing. So you want your money, at least the stuff you take off the table, to be in things that are just not correlated with being an entrepreneur. Yeah.

I'm still way over allocated in investing in startups and angel things. And I've done reasonably well. I have a couple that look like they're going to be very successful, but I've also had 10 or 20 that do anything.

And one of the things that new money and entrepreneurs will do is you'll get pitched on all these startups.

They do a lot of diligence and they only write one or two checks a quarter, right? Or they do it with friends. And so early on, I would probably say yes a lot more than I would now because I've been on a sector instead of on a team. And now I'm pretty judicious. I also do a lot of advisory work for equity. So I have...

equity in a bunch of different companies and some I also write checks for. So I got out of Spadera and I didn't make money there. There were stock options promised that weren't delivered. And this is like a pattern. I do work where I should have made a bunch of money and I don't. And so I went to Tibet and I'm just going to go learn meditation from the masters. I wandered around for three months and just learned a lot of stuff.

And I came back and I'm like, okay, the world's a little bit different than I thought it would be. I did another big personal development retreat with holotropic breathing, a bunch of transpersonal psychology. Like, oh, wow, I'm living in a world that's a little bit more spiritual than I thought it was. And I'm willing to be curious and scientific about it. And I'm not going to say that cannot be, therefore it isn't. Because if you have a direct experience of something, it's of some value.

So I decided I would have curiosity instead of skepticism, which was really beneficial for me. And I came back from Nepal and Tibet. I ended up getting remarried and I just have one very young baby. And I just feel this calling to go do a vision quest. And I didn't know why. And what I've learned is that sometimes your body just knows what you need if you're willing to listen.

And to the point of like, I don't, I just don't need that. Like there's a reason. I don't know what the reason is. My body knows the reason. Like there's an innate invisible wisdom inside. In fact, the best investors harness that as well when they're picking a team. So,

I find a shaman online and decide I'm going to go to Sedona and get dropped off in a cave for four days. And I knew I'd already lost most of the weight, but I knew that I would eat if I was lonely. I felt lonely a lot. And I knew that I had this feeling that if I didn't eat six times a day, I'd go into starvation mode, which is death. And I was uncomfortable with that.

So I figured, look, if I get dropped off in a cave with no food, I can be hypoglycemic and hangry. And I'm just going to face loneliness and hunger at the same time and just see what happens. So she drops me off in a cave. It was called First Woman Cave.

It was according to the local indigenous people. This is where like their Adam and Eve came out because it shaped like a giant womb. So I spent four days alone in Hungary and it was actually transformational. I came out of it instead of being starving and weak, so energized that I ended up walking for 10 miles, climbed the wrong mountain to find my ride out and was completely unfazed.

No food, no water. There's water for four days in the desert. Yeah, you need that. But I just had water and a fire and that was it. And a sleeping bag. When you came out of that, you talked about the importance of mental health as well. So let's go into the realm of mental health. Why was that transformative for you mentally? And then what's your advice to people today who are suffering from mental issues, who

who aren't doing anything about it. I mean, we hear every day now people who had no previously reported depression, they don't tell people, and then the suicide rate has just gone through the roof. It's pretty crazy right now. There are some animals where if the animal's sick, it'll self-isolate to save the tribe or the herd or something. And as a regenerative farmer, sheep are not like that. If there's a sick sheep, it'll hide it because it doesn't want to get kicked out of the tribe. Humans are like that.

So if you're feeling anxious and depressed, you're not going to tell anyone because you might lose social standing and you might be ostracized and all these weird thoughts. So there's a lot of people who act one way.

And they feel another way. And I was one of those, that psychiatrist who said, you have the best camouflage I've ever seen. I'm like barely holding it together. But outside people didn't know my boss at Spadaro. I sat down once. I said, I need 10 days off. And he goes, what the hell? Like we're a startup. I said, I'm getting divorced. And he goes, what? He goes, how long has this been happening? I said, six months. You never said anything. You didn't change your performance. I didn't want it to interrupt my, like I was just hiding the amount of pain that I was in. Cause I'm like, it's not acceptable to be weak. And yeah,

So it's happening to lots of people. My advice is you can get help because you're not alone. It's happening all over the place. And if you're willing to talk about it, you'll find other people in the room have the same thing. And if not, hire a therapist. I had great resistance hiring a therapist because that means something's wrong with me.

And here's what's wrong with you. You're not perfect. You want to be perfect, right? Or at least better than you are. Well, okay. Then of course there's something wrong with you if you want to do it. There's always opportunities for improvement. So a good therapist is more like a coach to help you improve wherever you are. And I actually had great anxiety. I had no idea. I didn't even know what fear felt like. I had this mental loop that said, if there's no reason to be afraid, therefore, whatever I'm feeling is not fear.

And I lived my life that way. And it was only when a really wise woman in her 80s sat down and explained fears and emotion, it doesn't have to be logical. So if you're dealing with all this stuff, it's not hard to get out. I teach in some of my books, I write about this. There's something called EMDR. It's a really easy, accessible way to go in and find the thing that's most important, that's causing your pain and just train your system to be non-reactive to it. My whole next book that comes out

In Q1 of 2025, I'm writing about all these techniques. If something's triggering you to feel anxiety or anger or stress, there's a reason. It's just probably a hidden reason. And it's a reason that you can edit out so that you're no longer triggerable. What most psychologists will teach you is,

You'll have lots of strong feelings. Acknowledge that they happen. Set them aside. I'm like, screw that noise. I don't want to spend my energy on strong feelings and setting them aside. I would like to train my system to not feel fear from things that aren't actual threats. And so I've spent six months of my life with electrodes glued to my head.

I'm learning how to do very advanced meditation. And I've done this for 11 years for executives because you can turn off your triggers permanently so that all the energy goes into creating something that matters towards evolution. But in the meantime, if you're just feeling crappy right now, it's probably because you don't know how to sleep. And it's probably because you don't know how to eat. You might start with just taking care of your hardware. And sometimes that resolves it. And then talk to a therapist.

You're listening to part one of my awesome podcast with Dave Asprey, the founder of the biohacking movement. Be sure to tune in next week to my awesome interview with Dave.