A Billionaire Investor's Advice Is Not What You'd Expect

- March 9, 2026 (6 days ago) • 51:21

Transcript

Start Time	Speaker	Text
00:00	MFM	If you're crafting your own personal career and your high-agency AI is like a jet pack, we've taught children and young adults how to grind. We've taught them to persevere for the sake of perseverance. And if you're stuck... you're stuck.
00:13	Sam Parr	In order to do these exercises for finding your passion, you sort of have to be a ruthless asshole.
00:18	MFM	Think—unless you're trying to find that edge, somebody else may be...
00:22	Sam Parr	You have to understand the difference between risk and uncertainty.
00:26	MFM	People most threatened by AI are those who aren't continuously learning. They're the ones who are just doing the same thing they did ten years ago.
00:33	Sam Parr	"How many times, when you were doing it, did you want to quit?"
00:35	MFM	"I don't ever remember wanting to quit." </FormattedResponse>
00:37	Sam Parr	Really, really... What did the voice say when it was like, "I found my calling"? I want to talk about the book because there are a bunch of crazy stats in it. I want to talk about the Nobel laureate thing — that was interesting. But the craziest, like, one of the craziest things early in the book: I think, did you run this survey? It said that six or seven out of 10 people hate their job.
01:03	MFM	Yeah, so I had a co-writer, co-researcher on the book, and we spent a ton of time together on Zoom calls. Someone encouraged us to dive into a bunch of academic literature. We came across this Gallup poll that said 53% of people aren't engaged at work. So we had this idea to ask about 1,000 people: "If you could start your career over again, would you do it differently?" Seven out of 10 said yes. We then took that to work with people analytics to do the official academic version to make sure the statistical data was correct. Their number came back 6 out of 10—so still a really big number. There's a great book by Daniel Pink called The Power of Regret, and he has somewhat similar longitudinal survey data through people's lives. As you get older, regrets of inaction start to really weigh on you and ruminate in your brain. A regret of inaction is actively choosing not to do something, versus a regret of action, which is "I made a mistake." Humans are really good at allowing themselves to make a mistake, but the path I never traveled—the door I never opened—is heavier in their mind. The survey might have been getting at that: people thinking, "Wow, what if I had done something differently?"
02:25	Sam Parr	Well, the reason I was asking is I kind of want this whole—I'm kind of obsessed with the idea of finding your passion. Not just because of your book, but one of my favorite books is Mastery by Robert Greene.
02:35	MFM	Yes, I'm familiar with it.
02:36	Sam Parr	Which changed my life. That changed my life. But the reason I'm interested in it is because I previously had a company that I sold, and it was very successful by all the traditional measurements. I have a company now that's quite successful, and I like what I do. In the back of my mind, though, I think—maybe you can tell me if I'm wrong—that even grown-ups who are successful still ask themselves, "Am I following the right path? Am I going to be in that six out of ten or the four out of ten?" Do you find that even when you left Compact and eventually got into VC [venture capital]—which I imagine would be your calling—you still questioned it?
03:16	MFM	After the engineering degree, I went to Wall Street for three years, so I...
03:20	Sam Parr	You were, like, in research.
03:22	MFM	I was a sell-side research analyst. Yeah — I had two stops before I made it to venture, and in both cases I had a moment of reflection. It's more clear to me now than it was then, but I asked myself: "Do I see myself doing this 30 years from now?" In many businesses there's a "lifer" in the room — someone who's done it their whole life. I don't mean that judgmentally, but it gives you a way to reflect on whether that's the place you want to be, because they did it. In both cases, after about two or three years, I got to a no, even though I was doing well in those jobs. Thinking, "Do I want to still be doing this 30 years from now?" was clarifying for me.
04:10	Sam Parr	But you said something interesting. Alright— I thought the book was amazing. The best chapter, the best part, was the early section about finding your passion. You said, "That's the hardest part." And, as you just said, "It didn't seem clear to me then, but it does seem clear to me now." I was questioning that.
04:26	MFM	Well, I did that exercise in my brain, and there's another exercise that Bezos is famous for: what he calls the "regret minimization framework." He asked, "What would my 80‑year‑old self advise me to do in this situation?" This is another way to get at what I was doing and to reach this notion of — you only have one life. Are you really thinking about this decision with a reflection of your whole life? Your 80‑year‑old self is probably more risk‑seeking than you are in that moment, because he's trying to minimize that regret. </FormattedResponse>
05:01	Sam Parr	What was the exercise you did then? How old were you? </FormattedResponse>
05:03	MFM	The thing I did is what I already said. I asked myself, "Do I still want to be doing this 30 years from now?" I did it once when I was an engineer, so I was 23 or 24.
05:15	Sam Parr	But was that voice loud?
05:17	MFM	I think it was loud. I had no inhibitions whatsoever about walking away — it didn't bother me. I may have benefited, in the back of my brain, from the fact that my father went across the country. He took a flyer and a job; he was recruited from Virginia to Houston to be one of the first employees at NASA.
05:39	Sam Parr	That's cool.
05:40	MFM	And I knew he had done that. So, I didn't come from... I think if you come from a family where multiple generations have stayed in the same town, it may feel really wild to just "take flyers." </FormattedResponse>
05:56	MFM	Alright, so this episode is all about excellence. A while back I shared my personal framework for building excellence in my own life, and the team at HubSpot turned it into a 30-day operating system you can check out right now. It breaks down the systems it took me 10 years to figure out and shows how I actually use them day to day. These are systems that genuinely changed my life. So if you want to build a good life, scan the QR code or click the link in the description [link in the description]. Now let's get back to the show.
06:26	Sam Parr	When I was 21 years old, I'm from Missouri. I went to school in Nashville, Tennessee. I had a hot dog stand, and that's how I paved my way through college. It was called Southern Sam's Wieners — the wieners were as big as a baby's arm — and we had a bunch of locations. It was really fun, but I was like, this is so hard... being out in Tennessee with a hot dog stand was so difficult. I was obsessed with the internet, but I didn't even know where internet companies "lived," so I googled, "Where do internet companies live?" It said San Francisco, and I was like, what internet companies are cool? What’s the hot thing? At the time it was Uber — it was still called Uber Cabs — and something called Air Bed & Breakfast. I started looking into this Air Bed & Breakfast and cold-emailed a guy named Brian, the CEO. He didn't reply, but I found another employee named Justin and emailed him: "I'm going to be there on Monday. Can I interview for this company?" Obviously, Air Bed & Breakfast became Airbnb. They asked if I lived in the Bay Area, and I said, "Yeah, yeah, I live there" — which, of course, I didn't. I was in college in Tennessee. I flew out the next day, got the interview, got the job, went back to Tennessee, dropped out of college, and sold everything I had. My parents are entrepreneurs in Missouri. They started their entrepreneurial career owning a fruit stand. I remember telling them I was going to leave school to join this thing. They asked, "What's a startup? Does it have health insurance?" I said, "It has health insurance, and it's paying $22 an hour. I think it's going to be fine." They said, "Okay, cool — we'll come pack up your stuff." That emotional support was one of the biggest things that separates people who win versus those who lose. I have met so many people — a lot of my friends are immigrants — and the immigrant experience is interesting because it seems to fall into two categories. One category came here with nothing, so they're willing to do anything to win and go down that path. The other path is, "I came here to create a big life — don't screw this up," so they take the safe path. My parents were not the safe path, and that support was the most amazing thing they could have given me.
08:24	MFM	I'm so glad you told that story. Even though the person this book is written toward is the person on the career path—and I mean that—we don't have a chapter on how to advise people; it's not written for the adviser. But I think it will be particularly interesting to parents and advisors to test whether or not they're willing to help support people in the way that your parents did.
08:52	Sam Parr	Well, I think that's a big deal. For example, you go to the doctor to get your basic stuff checked. I go to Cal. I go to school to get good grades. But no—do they ask, "Are you happy doing this?" I think that's why—I'm not sure I've ever formally learned how to find what I call ikigai [Japanese term]. It's this concept like a Venn diagram with four circles: what the world wants, what the world wants to pay for, what you're good at, and what you're passionate about. The goal is to find something right in the middle, but no one teaches that. So it's interesting—the reason I like your book is because that's what it's about.
09:31	MFM	In the chapter titled "Chase Your Curiosity," I tried to borrow as many of those types of exercises as possible. I even went out — I'm surprised I didn't find that one — but I found about ten others and I put them all in there. I'm trying to give people as many of those pathways as possible, because I think the very hardest part is to figure out actually what it is that drives you in this way. That's what's going to make it very easy for you to differentiate yourself. It's funny — you mentioned that one. There's a story in the book about this guy, Bert Beveridge [Tito Beveridge], in Austin, Texas. He's 40 years old and he's watching a PBS show, and they say: "Take a sheet of paper, put it horizontal, draw a line down the middle. Write on the left what you love to do and on the right what you're good at, and try and find something in the middle." Through that exercise he quit being a mortgage broker — he had been a seismologist before that — and launched a vodka company called Tito's at the age of 40.
10:35	Sam Parr	I think there's this famous Mozart quote where someone was asking Mozart, "Do I have what it takes to be the man?" Mozart replied, "If you're asking that question, the answer is no, because the conquerors just conquer." I hated his reply to that because I'm... but I'm curious. I don't even know all of the companies you've invested in, because you've been doing it for so long. I don't know how many accords you've invested in.
10:58	MFM	"I don't."
10:59	Sam Parr	I don't know... dozens, sure — a lot. Yeah. And you've been around all the movers and shakers, whether you invested in them or you passed or not. You have somehow touched all these amazing people. Did they follow a similar path? </FormattedResponse>
11:12	MFM	For the founders, I think you'd find a lot of different stories and different pathways that got them to where they are. I mean, the Zuckerberg story is pretty famous: he's at Harvard, messing around. That's very different from the path the Gates took, or even Bezos. So I don't know that there is a single pathway to that place. I'll tell you, I once asked Jeff Bezos, "How could you possibly be good at angel investing while running this company?"
11:40	Sam Parr	What did—what did he do, angel-wise?
11:42	MFM	Oh, he did Google "Uber" — like, it's a murderer's road. </FormattedResponse>
11:46	Sam Parr	He was in the seed round of Google. Yes—wow, that's amazing. What was the valuation then?
11:53	MFM	I think that first round was a "10 poster" [unclear]. But to get to the... he said the only thing he looks for is this insane determinism. He wanted to believe the person was going to go do this no matter what—come hell or high water. I think that may be a common trait of a lot of founders: they're just really, really determined and pushing against this thing. The other thing that's true of any tech founder is they're hyper curious about the edge of what the technology can do. Anytime there's a big disruption—AI being the most recent—but before that there was social media, the mobile wave, and the SaaS wave. All these waves create opportunity because incumbents are usually slow to embrace them, so you can run at these things fast. That requires you to be hyper curious about where the world is going and what's changing, so that you can master it before anyone else does.
12:51	Sam Parr	"You—there's this cool book called Grit. We talked about it a ton here on this podcast, and you cite it a bunch." "Yeah, it's awesome. Forget the exact equation, but it's basically like—she, Angela Duckworth, she's like, 'I...'..."
13:02	MFM	I think she started the original book with "50% passion, 50% perseverance." One thing we highlight — and I'm super grateful we had a chance to talk to her — is that we found a podcast she did ten years later where she said, "It probably shouldn't have been fifty-fifty. It needed to put more weight on passion." Her fear is that we've taught children and young adults how to grind — to persevere for the sake of perseverance. She believes that now this leads to burnout. If you have all this effort without the love for it, it feels more like work. One of my second principles, after you chase your curiosity, is to hone your craft. That's a lifelong journey: always learning. For people who are in the right space, that comes naturally — you just do it. You wake up and want to do it; you're drawn to knowing more about the craft. I think that correlates nicely with where she came out: it's hard to do all the things I recommend in this book if you don't truly love it.
14:14	Sam Parr	I didn't realize it, but passion—I think it's probably... I think "passion" is kind of a bad word, because passion implies that I'm going to like everything I do. If you talk to a lot of athletes, they're like, "I love competing. I do like practicing, but there are definitely days when I hate doing it. I'm a pro and I'm going to do it no matter what, and I love winning."
14:32	MFM	We highlight in the book that that word's kind of cliché and overused. Seinfeld gave a talk at Duke where he said, "fascination" was a better word. I think "obsession" is a good word. We titled the chapter "Chase Your Curiosity." Like, what—what is it that you can't ignore? What is this thing that you love so much that you always want to know more about? </FormattedResponse>
14:57	Sam Parr	"You know what? You did a good job of listening to all these exercises to find it. What was the most productive one that you found?" </FormattedResponse>
15:05	MFM	I mentioned the one that Tito had used. The team that wrote Designing Your Life has one that they say is most popular, which is "battle carting" [possible transcription uncertainty]. The exercise is to come up with three to five (3–5) potential career paths—not just one—and let your brain roll around in them for a while. Especially with AI today, you can imagine, "I'm going to do this—what does it look like two years from now? Who will I be working with? What might I like? What might I not like?" You can play out different scenarios and then ask, "What if it were this or this?" I think having the mental relaxation to not treat a path you've tried as an irreversible cost is important. Try it: "I'm going to go try this, and if it works, great; if not, I'll do something else." As your parents said, "it's okay to quit college and go work there." It's okay to quit the job you're in as well. I just fear we put so much weight on economic stability. You mentioned some immigrant families and what they push—there's a burden to prioritize that above and beyond what might be fulfilling in your life. I think it'd be better if we moved away from that, or at least balanced it a bit. We've gone pretty damn far to one side—let's bring it back a little.
16:27	Sam Parr	Have you messed up with your—like, have you had to pull yourself back with your kids?
16:32	MFM	Yeah. I think there is—and having them all in their early twenties, they're trying to find it. I don't know if they're even there yet, but there is this intuition as a parent, and I think it's well-intentioned to worry: to feel like they're on a safe path. "Safe" is usually economic, but it's also... risk feels like your risk. I love the story of what your parents did, and I've got a few anecdotes I found since we finished the book that are great and very similar to what your parents did. But I think it's the exception; I don't think it's the rule. I think a lot of parents would have tried to convince you to finish out and get your degree. I think that's built into most parents. And there are other people, besides myself, who have highlighted that—I’d call it the industrial college-matriculation path—has gotten very rigid, and it's competitive and it's grindy.
17:35	Sam Parr	Getting into college now is significantly harder.
17:39	MFM	Yeah — they've expanded the enrollment at these schools, but the number of people who want to go to college has gone way up.
17:47	Sam Parr	It's crazy.
17:47	MFM	It's crazy. Starting around sixth grade, well-intentioned parents start building the resume to get into college. We overschedule children today compared to when I was young, for sure. They're scheduled from when they wake up to when they go to bed. There's actually a chapter in Jonathan Haidt's book The Coddling of the American Mind called "The Decline of Play," where he argues we've made it harder for a child to explore and try on different ideas because they're caught up in this game to try and get into college.
18:22	Sam Parr	You had this crazy stat you said. I think it was about people who won a Nobel Prize in science—the scientists who won Nobel Prizes. Correct me if I'm wrong, but they were 22 times more likely to participate in things like acting or dance classes and things like that. What was that stat?
18:40	MFM	So this was work that Keith Holyoke had done at UCLA, and it relates to a lot of the concepts in the book Range by David Epstein. The finding was that people at the top of their field are much more likely to have a breadth of hobbies, speak more languages, do more things, and—almost, I think—have a broader lens on the world because they were able to try so many different things.
19:11	Sam Parr	So I read the book Mastery, and the premise is that being a generalist is kind of nonsense. You have to specialize in something, but once you specialize, you become a generalist. </FormattedResponse>
19:20	MFM	I think that's the right pathway. I do think you want to get started in an area where you can differentiate yourself. And then, in both the principal chapter on mentors and peers here, and even in the learning principle, I recommend—at a more advanced level—once you get up to this level, go broader: start to learn outside your field, find mentors and peers outside your field, and you'll get pulled in more innovative ways. </FormattedResponse>
19:50	Sam Parr	So, tell me more about that. That... just kind of blew my mind.
19:53	MFM	Well, I think what Keith's work highlighted was that some of the people who are able to reach the top of their field can draw on mental models from a variety of different places. Where a hyper-specialist... and David Epstein's book Range is all about this specialist versus broad thing — that's really the whole of the book. He quotes Holyoak as well. Many innovations in science have come from people who moved from one field to another: a chemist who becomes a physicist, for example. A person who's a lifelong physicist can develop mental models that become pretty rigid over time, because that's all they know. Once again, I think this is an advanced skill. I don't think it's the pathway to the beginning of success, because you'd be too broad early on. After you start succeeding, you begin to do this. Some of the smartest people I know — one person profiled in the book is Danny Meyer, the great restaurateur — when we asked him about his mentors, one of the mentors who influenced him the most wasn't from the restaurant industry. So, it is a more advanced skill, but it's a way to differentiate yourself along the pathway. It's a great, more advanced way to take yourself places you wouldn't have thought of.
21:19	Sam Parr	"You had this cool line. You said, 'If there's one takeaway that you should have from this book, peer groups — more so than coaching, consulting, courses, whatever — are probably the most powerful thing that you could use.' It's underdiscussed because it doesn't feel intuitive to want to be peers with someone who might take the same job as you. Yeah, but it's really powerful."
21:40	MFM	I think the way you describe it is right: everyone talks about mentors and no one talks about peers. I do have a chapter on mentors, and I offer a ton of very practical advice about how to play that correctly. But the peer thing—the idea is that when you get on that first rung of the ladder and you're trying to climb it, if you can develop a friend group (it might be four, it might be six) that are also on the same journey, that's helpful. Hopefully, I think outside your organization. You could start maybe with one person in your org, but for all the reasons we just talked about—how breadth of knowledge might give you insights you wouldn't have otherwise—if they're outside your organization they're going to see different cultures, different management structures, and they'll bring a different viewpoint to you than someone inside would. And then, with today's modern tools—if you're adventurous, create a Slack channel. If you just want something simpler, do a WhatsApp group or a Signal group—and share your learnings along the way.
22:42	Sam Parr	When I moved to San Francisco for Airbnb, I didn't actually end up getting to start the job. They had offered me the position and I had accepted it, but when they found out about something from college — I got a DUI — they said, "You lied on your resume; you said you didn't have a criminal record." I'm sober now. I don't do any drugs or alcohol; I'm completely clean and by the book. So I didn't end up getting to start, and I was stuck out in San Francisco. I was like, "What the hell am I going to do?" I ended up starting a company, and it worked out well, but it was a super low point in my life. When I got there, I created this thing called the Anti-MBA. It was my version of a book club. We met once a week. Each month we chose a book; we read a book over the month and discussed about a quarter of it every week. It changed my life — having that group of guys. I think you need a few things to make a group like that work: rules, rituals, and you have to take it seriously.
23:36	MFM	Yeah, and I think if there are people that are sharp-elbowed — climbers that step on other people — you kick them out. I think you need like-minded people who are equally gracious to one another.</FormattedResponse>
23:50	Sam Parr	"Who is in your group now? That's, like, a big shot now."
23:52	MFM	Well, one thing I've discovered lately is setting up different groups, like WhatsApp or Signal, for different topics. I think, for someone coming in early in a career, it's better to have people who are on that exact journey. I'm not in that place anymore.
24:09	Sam Parr	I have a company called Hampton — that's my main company. Are you familiar with YPO? It's like YPO. We have thousands of members all over the country, and [unclear phrase: "and you it's chris peer group"]. We also have executive coaches who lead the conversation. It's for CEOs, so the average member has around $20,000,000 to $30,000,000 in revenue or so. It's been really cool to watch these members team up. I'm in a peer group — we call them core groups. I'm in one as well, and it's like you have this a bunch of lines in there about peer groups, and I'm like, "Oh, you're writing my ads for me." </FormattedResponse>
24:39	MFM	Yeah... those things exist with YPO and with your thing for CEOs, but they could be done by anybody. </FormattedResponse>
24:46	Sam Parr	For sure. I mean, my wife, when she was pregnant, she had one for moms. I've got a buddy of mine who has one for Jewish dads. It could be anything, you know what I mean? But it really does change things.
24:59	MFM	It does. It really does. I think it can, and almost all of the other principles are accelerated, so your learning is accelerated. There's a great story in the book about MrBeast that ties to that. Your network is accelerated, too—so your network isn't just your network; it's now the network of the group, if people are willing to share introductions and that kind of thing, both for mentors and other peers. The group can be really helpful on bad days—everyone's going to have bad days—and there's a support element that comes into play that I think is really useful. Also, you may be at a shitty company. Your dream job may be the one you're in, but you might be at a shitty company. If you're alone, you have no way of knowing if that's normal or not—like the stuff you're exposed to. Whereas if you had a group of eight people who were all doing this in different companies, you'd get different perspectives on that. </FormattedResponse>
25:58	Sam Parr	What did the voice say to you when it was like, "I found my calling"?
26:03	MFM	"There was a lack of that voice that kept asking, 'Is this what you want to be doing thirty years from now?' That worry was gone. I wasn't having those negative thoughts, if you will."
26:15	Sam Parr	"And what was the thing that you were doing—investing?"
26:17	MFM	Yeah. Once I became a VC, I just adored every minute of the job. But a lot of that fits my individual personality. Now, there are people who... they say, "Oh, you can't be a VC because you're not the one actually doing the work." That never bothered me. I'm someone who's really drawn to intellectual breadth, and a service job—whether it's working in banking or working as a VC—gives me a window across many more companies than if I were working in just one. Also, I'm fairly certain I have ADD, and focusing on details is not something I'm good at.
26:54	Sam Parr	Like, whenever—when people... I've heard Jeff Bezos or Warren Buffett. Someone was like, "I tap-dance to work every day," and then you're saying you "adored every minute of it." It's like, "I think I found my passion," but I probably—like, running a company sucks 85% of the time. I did that in my last company that sold, and it was great. If you talk to my wife, she was like, "You laid on the floor all the time saying, 'I can't do this. I want to quit. This sucks.'" Like, is "I adored every second of it" right?
27:21	MFM	I don't know. I won't. I'm—I'm telling you the ex post kind of summary of it all.
27:27	Sam Parr	"But how many times, when you were doing it, did you want to quit?"
27:30	MFM	I don't ever remember wanting to quit — really, really.
27:32	Sam Parr	"That makes me feel horrible."
27:35	MFM	I think the CEO job is the loneliest job in America. I've said that many, many times before. It's hard. One of the things that makes it particularly hard is that you need to run culturally opposite to what's happening at the company. If the company's doing poorly, you have to bring the positive energy and make people believe it's possible. If the company's running hot, you want to bring them down to earth. This is my theory on why the CEO job's so hard: running counter emotionally to what everybody else in the organization feels is exhausting.
28:10	Sam Parr	It's exhausting in a world where I've grown to dislike the word and the idea of authenticity. It's sort of like when you're a young kid and you're trying to meet girls—people say, "Just be yourself." I'm like, girls don't like myself. If I want to be myself, I need to change and be better. Then people are like, "Be authentic," and I'm like, "But I'm not a good leader—I need to be better," you know what I mean? So they'll say, "Be authentic. Be transparent with your team. Tell them that you're not feeling great." I'm like, no—like, you have to convince them that we're going to figure this out somehow.
28:42	MFM	You know what I mean? Leadership is really, really hard. I think one of the things that is often not talked about enough — both in Silicon Valley and in the broader celebration of the founder — is that if you're successful and your company grows, you're going to go from 10 employees to 100 employees to a thousand employees. Eventually, leadership is going to be required and it will matter. You don't have a place to learn that. There's no book that teaches, "Here — you're a founder; you want to learn to lead people." It's not discussed much. But the Zuckerbergs of the world... I know for a fact that Larry and Sergei — there's this gentleman named Bill Campbell, who's unfortunately passed away.
29:31	Sam Parr	He was the "Trillion Dollar Coach."</FormattedResponse>
29:32	MFM	Yes, Campbell was there ten years after the IPO, still running the weekly team meetings with Larry and Sergey.
29:38	Sam Parr	"Were they just bad leaders? I mean, what—what I..."
29:42	MFM	I don't know. Steve Jobs used Bill also, so I don't know that makes him bad. I'm just highlighting the fact that there's no reason, from a DNA standpoint, that a founder should naturally be able to lead a thousand people. There's a skill set required to lead that many, and no one's taught it to you. </FormattedResponse>
30:00	Sam Parr	"Can you learn it?"
30:01	MFM	Yeah, I think you can learn it. I think certain people have. I think Zuckerberg has learned it. I think Bezos didn't have any leadership skills going in — he had never run a large team.
30:11	Sam Parr	"What do you suggest to someone who wants to learn how to be a better leader?"
30:13	MFM	Get to know Bill Campbell, but he is no longer with us. I've often said: get two or three mentors who have run large groups. They will all have their own leadership philosophies and patterns—try those on and see which one fits you best. That's maybe the middle ground between being authentic and not. Having a programming philosophy is better than having none. I can't tell you how many founders have gotten to 200 employees and they're not running a weekly meeting; they don't know how to do it. Some structure is better than no structure. Therefore, rather than saying one of those CEOs you talked to is absolutely right, find out what they're doing and see which one feels best for you and your org.
31:02	Sam Parr	Well, you talked about that with Danny Meyer. Danny Meyer is probably most known outside New York for founding Shake Shack. You said that he thought he was going to be a lawyer or something, and he hated it. He went and toured a bunch of restaurants. His uncle was like, "Dude, what are you doing? You gotta get in the restaurant business." So what he did was take a field trip to tour restaurants, and then eventually got a part-time job working at a restaurant before starting his own.
31:28	MFM	Yeah, he also did a tour through Europe as a "stache," which is a fancy word for "work for free."
31:33	Sam Parr	But in the book you're like, "He still does that." So whenever they're opening up a new restaurant, he goes on field trips. When he opened — I think — a barbecue place, he went back to St. Louis and tested stuff. Is there a world where a white-collar person can take these field trips?
31:52	MFM	I think so—or at least the notion of it. One of the arguments I make—I pound the table in the learning chapter—is that most people don't think about continuous learning in their job. Founders do because they're learning new technologies, and maybe doctors do because it's required by law. But most people who get into a field: the college and high school experience were so exhausting that they're worn out and glad they're done learning, and then they go to work. Whatever you do, I guarantee you that with AI out there there's some nuance of what you could be doing that's new. Unless you're trying to find that edge, somebody else may be. I think the people most threatened by AI are the ones who aren't continuously learning—people who are just doing the same thing they did ten years ago because they're kind of a "widget," and that work could be automated. The people who are curious about what's possible are naturally going to see this AI thing pop up and say, "Wow, that's a new tool; I better figure out what it can do for me." Those are the people who are hardest to replace. If a company is trying to figure out AI and one of your employees is spending more time on it than everybody else, they're the last person you're going to fire.
33:19	Sam Parr	I think that what I've been trying to tell a lot of young people—particularly a lot of young men—is this: you have to understand the difference between risk and uncertainty. Risk is oftentimes a lot less than people think, but uncertainty will always exist no matter what. You just have to get comfortable with that. I also think that, in order to reduce risk, people don't realize how many things in life they can try before they buy. For example: I moved from Texas up here. I rented an Airbnb for two weeks in a neighborhood I wanted to check out and tested it. I actually realized I hated that neighborhood, but I liked this other area.
33:54	MFM	Yeah.
33:54	Sam Parr	Or, you could do that. I remember one time I wanted to buy a fancy car. I tested it on Turo and I was like, "Ugh—I don't want to own this car; this is a pain in the ass." You can email someone—you'd have to email probably 50 people—and you could actually shadow them. I mean, most decisions are reversible, and there are ways to reduce risk.
34:14	MFM	No doubt. When I was an engineer, and before I went to Wall Street, I had read Peter Lynch's One Up on Wall Street. I was trading stocks in my spare time, so I was unconsciously testing the field I would eventually go into. So yes—don't quit your job tomorrow just because you're unhappy. Start figuring out which direction is the right one to move toward. </FormattedResponse>
34:40	Sam Parr	Some of the people that you talk about — for example, in the book you talk about Robert Zimmerman, aka Bob Dylan. You say he "found his fascination" and he followed it pretty ruthlessly and became Bob Dylan. But you also, only briefly, mentioned that he's notoriously prickly — he's hard to get close to. I know you've worked with Travis Kalmyk, who's a pretty wild guy. The people who, in order to do these exercises of finding your passion, you sort of have to be a ruthless asshole, you think?
35:13	MFM	I don't think so. I mean, Danny's one of the nicest humans I've ever met in my entire life. Even someone like Bobby Knight, who we have in the book, is known as being that way. He's probably got the biggest coaching tree in the history of the sport, which means people have developed underneath him — both as coaches and players — and become coaches themselves. So even if, you know, this prickly guy you see throwing the chair is not the one that developed all these humans and put them on their way and on their path, one of the things I love about a lot of the stories in the book is that these people reach a place where they're touching so many people in their field. I think that's a more fulfilling test of "Were you successful?" than "Did you hit some milestone?"
36:05	Sam Parr	Yeah, but it's a lot easier to do a bunch of stuff—like following your passion—when you have hit milestones. Sometimes, when people say, "follow your passion," what I really want to tell them is: basically, this sounds crude, but if you can get rich fast, do that.
36:21	MFM	Some people get in a position where they spend right up to what they earn. Then they don't have any savings, so they move from one town to another. A lot of the people in the book do that. If you're stuck, you're stuck. You might have to stay in a job because you've built an expense burden that goes right up against the top of it. I saw a ton of those people when I came to New York.
36:45	Sam Parr	What did you see?
36:46	MFM	"I mean, we were getting paid decent money... for..."
36:48	Sam Parr	This was when you were a researcher.
36:50	MFM	Yeah. For entry-level jobs, they'd run and get... they'd go get the place in the Hamptons, they'd join the private club, and they'd run their budget right up to the top—sometimes above it. It's weird: if they don't get the bonus, they're underwater.
37:04	Sam Parr	I know people who make seven figures a year — $1,000,000 — and literally have $0 in savings.
37:09	MFM	I understand.
37:09	Sam Parr	When I was early on, I used an app called My Weekly Budget. I created a budget and kept a spreadsheet that tracked how much cash I had saved. For example, $10,000 to $20,000 — it showed how long you could live without any income. The name of the game was to square away as much cash as possible while keeping expenses low. Anything above six months was your "F-you number," meaning you could go and try and experiment.
37:35	MFM	Yeah, it gives you flexibility.
37:37	Sam Parr	Yeah. It was ruthlessly disciplined to make that number bigger, even though I didn't make a lot of money. I was living very frugally, and I don't think people understand that. Things like college debt—which, I'm very privileged to say, I didn't have—completely ruin it. So there are a bunch of these irreversible decisions that can really screw you up when it comes to being able to chase down some of these things.
37:57	MFM	I agree with it.
37:58	Sam Parr	Last night was special because I sat across from Jim Cramer. Next to him was Henry Blodgett, who founded Business Insider. It was just a lot of crazy people. When you knew these guys when they were younger, was it clear that you were all going to succeed? Or have you been surprised that someone has been as successful as they are?
38:15	MFM	Well, I think it goes back to our discussion on peer groups—like connecting with people. I've just always found, and I think I got more attuned to this the older I got, to have a big tent mentality: have as many friends as you can, try not to judge people too much, root for people to be successful when you can, and it'll come back to you in spades. Now, I guess I've never been surprised that the people that end up, you know, in Silicon Valley—in the middle of it all—continue to move forward, just because it attracts so many ambitious people. So I don't know... I haven't been radically surprised by anybody's staying power. Keep in mind I'm 59 years old, so I have the benefit of time to build that network. I had 25 years as a venture capitalist.
39:13	Sam Parr	But I think you were on the board of—what's the one with you and Danny Meyer? You were on the board of OpenTable; that was, like, twenty years ago.
39:20	MFM	Mean, yes.
39:20	Sam Parr	It seems like you kinda hit...
39:21	MFM	It was.
39:22	Sam Parr	Right — up pretty early in. Yeah, into investing, right?
39:25	MFM	"That's kind of key in venture."
39:26	Sam Parr	What do you mean?
39:27	MFM	Oh, just to be in front of the wave—or whatever rolls out. You can't be late.
39:34	Sam Parr	With AI going on right now, does this—does this remind you of a different... [unclear: "in venture"]?
39:38	MFM	I've never seen it quite like this. Really. One thing I think: throughout my career, venture capital has only gotten more competitive. And now, as I'm hanging up my boots and watching the next generation, it's even more competitive. The burn rates that VCs are comfortable experimenting with are bigger and bigger than ever. I thought our $2 billion-a-year burn rate at Uber was pretty frightening. OpenAI is burning way more than that.
40:09	Sam Parr	How much are they burning?
40:10	MFM	I don't know. I've seen different numbers. I don't have access to their financials, but... </FormattedResponse>
40:13	Sam Parr	Uber was losing 2 billion a year.
40:15	MFM	Yeah, but OpenAI is at like eight or ten.
40:17	Sam Parr	"What does it make you feel when your company's losing $2 billion a year?"
40:20	MFM	Scared shitless.
40:21	Sam Parr	Really.
40:22	MFM	Yeah. Oh, yeah.
40:23	Sam Parr	How did you map that out? How do you go to bed at night knowing that? Are you—what do you tell yourself? You're like, "Well..."
40:28	MFM	I didn't sleep much. There was a piece of it that I think — as the venture industry gets more industrialized — was a problem. I think the Lyft investors knew they had to keep funding liquidity. For a bunch of reasons that relate to network effects, it was always supposed to be kind of a single marketplace that would win. But if you don't have the constraint of financial viability, you can lose money to create the perception of liquidity. You can pay drivers to be present when they wouldn't actually be there.
41:06	Sam Parr	Yeah, I used to joke: my last company in San Francisco—we didn't take venture capital, but we used to say we were still VC-funded, because Uber and all these companies would give the craziest referrals. I remember giving my referral to everyone: "Oh, I ride on Uber for free."
41:22	MFM	I get it. It wasn't until Lyft went public first — which is probably the best thing that could have ever happened to Uber — that Wall Street held them accountable for being profitable. It's at that point when things really tipped, and Uber was able to take advantage of the network effect by being larger. It now spits off well north of $10 billion a year in free cash flow.
41:48	Sam Parr	"That's how big it is now? That's insane. Did you do that? Is that bigger than your prediction?" </FormattedResponse>
41:53	MFM	Oh, I made a prediction about the market cap. It had a bunch of ranges. I don't have it in front of me, but Dara got it to a $200 billion market cap. I don't know if that was in... I assume you're referring to the blog post I wrote.
42:06	Sam Parr	No, I haven't read.
42:07	MFM	Oh, okay.
42:07	Sam Parr	Yeah, what did you say? Or... what was the...?
42:10	MFM	Another professor at NYU wrote a blog post that said, "it would only be worth 4 billion," and I pushed back.
42:16	Sam Parr	Remember—that we did talk about that. Yeah. Did you see the blog post the other day on Substack where they're like, "AI is gonna make the economy worse"? Do you see how one blog post, like, brought down...
42:26	MFM	It's pretty.</FormattedResponse>
42:26	Sam Parr	Amazing — that's crazy, right? Yes. Did your blog ever do that?
42:30	MFM	Not—not of that scale, no.</FormattedResponse>
42:32	Sam Parr	Yeah, that was — that was insane.
42:34	MFM	Insane — there's a lot of fear out there. Just remember Warren Buffett said, "Be greedy when others are fearful and fearful when others are greedy." The first wave of AI was a lot of people being greedy, and now all of a sudden there's fear for the first time. So if you're a net buyer of stocks, this is when you this is when you sharpen your pencil.
42:56	Sam Parr	You've seen all these interesting founders. Other than—I mean, I don't want to hear Travis or some of the big-name ones—who have stuck out as particularly sticky and formidable?
43:06	MFM	Well, one of the most impressive people I know is a guy named Rich Barton. He founded Expedia and then Zillow. Expedia was acquired by Diller, so he knows Barry and all that. Rich has this remarkable ability to be in the top one percent as a product/technology disruptor, but also as a leader — that thing we were talking about before. I usually see people tilt one way or the other, and not both. He's this rare person who does both, and so I frequently lean on him for advice.
43:44	Sam Parr	Do you have an example — like a story — of where good leadership changed...?
43:49	MFM	Getting companies to pivot fast when they need to. I mean, now with AI, any companies out there... You mentioned what happened with this report: that DoorDash is down 5% because the report said, "you could build DoorDash for free," which I don't believe, but you know, whatever.
44:05	Sam Parr	Yeah. And that report, by the way — for the listener — was basically this: "What happens in the world if AI is so efficient that we don't have jobs? And if we don't have jobs, then we're not buying stuff?" It was just a story. It was an idea.
44:17	MFM	But how do you get—so, the thing I was going to mention is: how do you make sure your company is properly aware of this new wave, and how do you get everyone super excited about figuring out what it's going to mean for your company? That's not easy to do. I'm back on the board of Zillow, so I watched them do that recently. It requires having both the conviction to make that kind of pivot and move, and the ability to get people to follow you.
44:47	Sam Parr	That's funny that you said it was like being good at product and being a good leader. I think you also said — you also say — that Jeff Bezos is one of those guys who does two things really well.
44:57	MFM	It would be a good exercise for someone to write down the leadership techniques of Jeff Bezos, because Amazon remained innovative after it grew to about 100,000 employees. That's very hard to do. It's not just one human—it's one human creating a system that reinforces whatever he thought. You see what I'm saying? How do you make that system keep doing that even on days you're not there? With him and Elon, I just don't think people fully grok how they're able to lead.
45:31	Sam Parr	A lot of these people — the titans of industry — do you think there's any correlation, or reverse correlation, with happiness?
45:41	MFM	I don't know anyone who laughs louder than Jeff Bezos. If you've been around him when he lets go one of his guffaws, man — I think he really loves life. I'm just saying that I don't think there's a correlation. I mean, every chance I get, if Toby from Shopify does a podcast or something, I'm eating it up, and I find his attitude on leadership and life to be light-hearted... He...
46:14	Sam Parr	Seems like another one of these product leadership guys. He's got a very unique flavor of leadership. He has a very wise...
46:20	MFM	He has something wise about him—years, roughly.</FormattedResponse>
46:23	Sam Parr	Yeah, there's something wise about him. Do you see where he took screenshots of his computer screen every ten minutes for the last twenty years? He was just—he's like, "I'm a nerd, and I just love having this diary of what was on my screen." He was tracking all of this and said, "I didn't know what I was gonna do with this. Now that AI exists, I can upload this and it could teach me about myself." He's got this really cool— I call it nerd wisdom. You know, Dharmesh at HubSpot.
46:50	MFM	I have met him, but I don't know him as well.
46:52	Sam Parr	He's kind of the same thing, where there's this group of guys who are, like, very... When you think of a leader, sometimes you think of a Napoleon—rah-rah, rile people up. But there's this other group of fairly introverted people. They're quiet, and when they talk, you listen. I think they're both useful. For someone who's 18, 19, or 20 listening to this—you did all this research for this book—what biographies do you suggest they go read?
47:16	MFM	I mean, I think it would be heavily dependent on what interests them. </FormattedResponse>
47:20	Sam Parr	Or rather, what made the biggest impact on you?
47:21	MFM	I don't know if I was reading biographies at 17. I really got into reading when I got to business school. They're all listed in the back of the book — there are 35 books listed. But I think the key is this: it doesn't even have to be reading. There are so many podcasts (like the ones you do) and YouTube interviews with people. It's so easy to go learn about something. So, "whatever interests you, go learn more about it" and see if that takes you somewhere. See if it makes you excited, if it makes you want to pick up the next one. If it does, I think you're probably in the right lane. If not, just pay attention to what fascinates you — pay attention to what interests you. I'm a big believer that more people can chase careers in their hobby than others might think. If there's something you're super passionate about, even if it's a hobby, you might be surprised — there might be a way to make a career around it.
48:24	Sam Parr	Well, it's a lot easier now with the Internet.
48:26	MFM	This is... but, by the way, I'd love to close with this: that you just made. If you're—like I said—someone who's disengaged at work and went through some process you didn't care about that much, I can understand why this AI thing would feel threatening to you. If you're crafting your own personal career and you're high-agency (I think that's the word you used earlier), AI is like a jet pack. You can do more stuff than you ever could before. You can learn faster than ever in the history of time. You can find people to connect with; you can network faster than you ever could before. So, if you have agency, direction, and you're headed in [that direction], AI is going to make things way better. I think it's just this interesting paradox: there are people out there who fear that it's going to dismantle them, and there are people who are like, "Oh my god, I can't..." I've met so many—what I would call—SMB founders or regional founders running, you know, businesses that are laundromats or a storage facility, and they've discovered all the things they can do with AI, and now they feel superhuman.
49:40	Sam Parr	So, I'll wrap up with this story — you'll dig this. My mother-in-law, her name's Smithy. She came to America from Haiti at 14 years old and didn't speak English. She married my father-in-law, Jeff. Jeff owned a moving company. Smithy was a stay-at-home mom for a long time. When the kids grew up she said, "I'm kinda lost. I need to do something. What's going on?" About five years ago she said to me, "Sam, I think I'm gonna start an online store that sells pillows." I was like, "Pillows?" She persisted, so I told her, "There's this thing called Shopify. Just start there." It's been five years since then. She now has a pillow company that sells over $1 million a year. She has a warehouse in New Jersey with five full-time employees selling pillows. She was just in the pod [podcast] and she uses AI all day. She's like, "How do I buy an ad?" and ChatGPT teaches her. Or she'll ask, "How do I—?" and YouTube and ChatGPT tell her what to do. She didn't know the word "e-commerce." She didn't know what that meant. She basically just knew what Google was. Now, in her late fifties, she started an e-commerce business that does millions of dollars a year. That's amazing. Crazy, right?
50:51	MFM	Yeah, no. But there's never been a better time to propel yourself forward, if that's what you're prepared to do.
50:58	Sam Parr	To do well — you, for doing this, brother.
51:00	MFM	Alright, alright. God bless. Take care, yeah.

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A Billionaire Investor's Advice Is Not What You'd Expect

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