Scott’s Career Advice: Imposter Syndrome, Startups & Networking
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Welcome to Office Hours with Prop G. Today, we're kicking off a special two-part series all about careers, navigating them, advancing them, maybe even surviving them. I'll be sharing my best advice, which may not be very good. No corporate speak, no bullshit. I am going to tell you exactly what I'm thinking. And it might offend you and it might upset you. And guess what? We're both going to be fine. Let's bust right into it. First question.

Hey, Prof G. My name is Hank, and I'm an American that's been living in Stockholm, Sweden for the last eight years. And I've really loved your office hours advice, listening to you and getting your opinion on things. And what I thought that would be very helpful to get your thoughts on is dealing with imposter syndrome.

All the time, I feel like when I'm working, that, I don't know, maybe I'm not good enough, even though from all my previous jobs, all the feedback's been great. And now I'm about to move on to a CMO role, which I think is kind of way out of my league, even though all the interactions with the CEO and all the interview processes went really well. So

So I don't feel like I should have those feelings, but again, they're still there. Just wondering if you've ever faced this in your life and if you have any strategies to kind of get over this. Anyway, looking forward to your thoughts and thank you so much for everything. Hank from Sweden. The data says with imposter syndrome that you're supposed to practice self-compassion, be kind to yourself.

acknowledge and accept your feelings, challenge negative thoughts, say, well, the market and other people who are smart think I'm in the right position. So maybe there's something to their views. I find that talking stuff out really helps like telling people, Jesus, I feel like I'm in over my head or I don't deserve it. I just feel like

you know, getting those thoughts out, help address them. And hearing yourself talk, you start to solve that type of thing. Being positive. I mean, eating, you know, eating well, being in good shape. And I think you just start to feel more confident across all areas of your life. Like I'm strong and I'm healthy, which means I'd be really good at anything, including my job.

So it's imposter syndrome is a form of intellectual self-doubt that can affect anyone, regardless of their job. People with imposter syndrome often feel like they could have done better, even when things go well. I think if you don't have a little bit of imposter syndrome, it probably means you're a bit of a sociopath or arrogant because the whole point, the reason we're so competitive is

is that it's good for the species, right? I want to do better than the guy or gal next to me, which creates better performance, which results in a better society, and onward and onward, and things get better. So this competitive spirit is important. Constantly referencing and comparing yourself to others is natural, and that's part of that competitive instinct, but it can result in a lot of self-doubt. And I just think, well, first off, a lot of people have this. I just said on a previous Office Hours that

I've never felt like I was qualified to do anything I did. And then I realized when I showed up that everyone else is an imposter too, and everyone else feels as if they're an imposter. So it sounds like you're doing really well. Acknowledge everyone around you that they might be smarter than you think, and it picked you for a lot of good reasons. I would say be kind to yourself, try and engage in things that make you feel positive. I think working out and eating well make you feel talented and healthy, and that you would be good at almost anything because you're this strong person.

a healthy person, but recognize everyone feels a little bit of that. And again, go back to the notion that the market may be smarter than you think, and you deserve to be where you are. Thanks for the question. Question number two. Hi, Prof G. My name is Nicholas, and I'm a huge fan of your podcasts. Special shout out to Ed for having to laugh at your dick chokes. Anyway, I'm 36, Canadian, and have about 10 years of experience as a business generalist.

I started as an engineer, got a top MBA, and then spent about five years in Luxembourg at McKinsey and Amazon. Tired of corporate, I've moved to the south of France to join my in-laws' family business, only to confirm your thoughts about that region. Great place to spend, but not to earn. So, my wife, two kids, and I have moved to Toronto for better opportunities.

Now, I think my best move would be to join an early stage startup as a COO or chief of staff to build a company and some wealth along the way, which sounds super interesting and challenging. My question to you is this. Knowing the high failure rate of early stage companies, what advice do you have for picking a winner? How can I assess which startup is worth betting this next chapter of my career on? Thanks and keep doing what you're doing.

Thanks very much, Nicholas from Canada. What an interesting life you've led and how it's kind of good to be you. Okay, so it sounds like you want to go to a startup.

So first off, nobody knows. And there's hints. What I've always done is I've always picked people, not companies. And that is, if you have the opportunity to interview with small firms, you want to go where you think the people are most impressive. Because a lot of times with small companies, they end up doing something that they hadn't originally anticipated. But if the people are super smart, they can more often than not figure it out. So I think you want to go somewhere where you think the person I'm going to report into, I'm going to learn a lot.

and these people just seem really together. Now, hopefully if it's just a stupid idea, then fine. There might've been a lot of smart people with that dog walking app backed by SoftBank, but that was just a stupid idea. But you basically want to go into battle with people that you would want to go into battle with. And then also I think where the company is in the life cycle is sort of interesting. My general experience is that joining a company with zero to 10 employees

is that the risk reward ratio isn't there. Now, if the company works, those people make a shit ton of money. But those are the people we read about in the newspaper. We don't read about the six out of seven companies and end up with a zero. Even worse than that, sometimes they go three, five, 10, 20 years and then end up with nothing. That happened to me at Run Envelope. I was there 10 years to work my ass off, invested $3 million of my own capital to end up with nothing. That story doesn't get told a lot, although I tell it a lot.

But the zero to 10 is huge upside. But I would argue like if you're not the founder and you're not going to get 20 or 30% of the company, I'm not sure the risk reward is there. At the same time, when you join a company that's already at a couple thousand people, unless it's a moonshot like a Google or a Salesforce, you'll make good money, but you'll never make super, super huge money. I find that the sweet spot from a risk reward standpoint is kind of

20 to 200 employees. And that is, you're still early enough to get significant equity, but if they're at that point, it means that they have probably some level of product market fit. So I find that sort of the sweet spot of risk to reward, especially given that you have

you have a family. In addition, there's other signals. Who are the people who have backed the company? How much capital have they raised? How much press have they received? There's, you know, not all of these are, you know, it's sort of the good housekeeping stamp of approval, which by the way, approved talcum powder, which ended up giving people all sorts of cancer. So it's not a guarantee, but when there's good people and VCs who,

or customers involved, there's signals you should be able to discern around how the company is doing. But again, I like the sweet spot of kind of, there's some limited evidence of product market fit, but at the same time, if I show up, I'm still gonna get quote unquote real significant equity. But again, this is a good problem. And also you gotta let the market decide, you gotta get the job first. So your first objective is to get one, ideally two offers so you can play them against each other.

But let me finish where I started. With your background, living in Toronto and a family, it's just good to be Nicholas. Thanks for the question. We have one quick break before our final question. Stay with us. Fox Creative. This is advertiser content from Canva. ♪

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Welcome back. Question number three. Hi, Scott. My name is Sasha. I'm a big fan of your podcast, and I'm a sophomore in college in Boston, and I find your career fascinating. With that, I need help understanding networking. As a student interested in a career in consulting, there's a lot of pressure to quote-unquote network. How can I do this authentically? And I'm lucky to already have connections at MBB, but what can I ask those connections to really do for me? Thank you for your wisdom and considering my question. Thanks, Sasha. So,

I say yes a lot. Business school and college are fantastic ways. You get invited to all this crazy shit. You get to go see, I remember, I don't know why this popped into my mind, I went and saw Don Valentine speak at an event at Haas. And you as a student can go up to Don Valentine and say, hi, I'm Scott Galloway. And I found out he ran this firm called Sequoia. And I don't think I leveraged that content, but I eventually ended up raising a lot of money from Sequoia.

But you can kind of call on anybody from a professional standpoint, and they'll meet with you, have coffee with us. When students call me, and I'm not suggesting you do this, and say, I want to have coffee, I'm much more inclined to have coffee with them than even at this point, like a CEO of some company right now. You just have currency to meet people. And I would take advantage of that, both professionally or kind of networking at these sort of corporate events. But also a different type of networking is just to try to make as many friends as possible. Right.

and have fun, say yes, go to football games with people or whatever it is they do at your college, go out for a drink. Also invest in relationships, send people nice notes, be happy to see them. There's this great study that looked at who are the most popular kids in high school. And was it the athletes? Was it the best looking kids? No, you know what it was? It was the kids who liked the most people, not the kids who had the most people who liked them,

But the easiest way to get someone to like you is to like them. The kids that were friendliness, waved at other people in the hall, were confident, those kids were the most popular. I thought that was so obvious but fascinating.

So what do you want to do? You want to go to as many of these kind of networking events as is, you know, doesn't get in the way of your studies. Say yes to stuff with your friends. Be nice to people. Be friendly. Like as many people as you can. And take advantage of the fact that people want to meet with you and you have access to all this incredible stuff. And more than anything, try not to be in your dorm room or your fraternity or wherever you're living more than eight or ten hours a day.

Be out, be out in the wild, be out in the jungle, meeting people, running into unusual opportunities. That's what I worry about with most young men is there's too many temptations to sit at home and believe you can have a reasonable facsimile of life with a computer and an algorithm. No, get out of the house, go on campus, go to these events. Another trick I do, I did this whenever I walked into a room, whether it was a networking event or a corporate event, a business school or a bar,

I would demand that within 10 seconds, I'd lock eye contact with someone and I'd walk up and introduce myself. I'd break the seal. Because it's easy to sort of walk into a room and you don't know anybody and you just kind of sit there and you look at your phone to pretend you're doing something. And before you know it, you're just sort of

you know, sequestered and you're getting too used to not talking to people right away, you roll into a situation, you're going to go up to a group of people or to someone and introduce yourself. Just break the seal right away. Anyway, Sasha from Boston, thanks for the question. That's all for this episode. If you'd like to submit a question, please email a voice recording to officehoursatpropertymedia.com. Again, that's officehoursatpropertymedia.com.

This episode was produced by Jennifer Sanchez. Our intern is Dan Shalon. Drew Burrows is our technical director. Thank you for listening to the PropG Pod from the Vox Media Podcast Network. We will catch you on Saturday for No Mercy, No Malice, as read by George Hahn. And please follow our PropG Markets Pod wherever you get your pods for new episodes every Monday and Thursday.

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