Tim Ferriss at a Career Crossroads: How Should He Shape His Next Chapter?

BRIAN KENNY: Welcome to Cold Call, the podcast where we dive deep into the stories behind groundbreaking Harvard Business School case studies. Tim Ferriss has been called the Oprah of Audio. His podcast, the Tim Ferriss Show, surpassed a billion downloads and reshaped the digital media landscape. Yet at the height of his success, Ferriss found himself at a crossroads. With podcasting becoming a crowded competitive space, he wondered whether the medium that had defined his career was still the best vehicle for his curiosity, creativity, and impact. How should a creator who has always thrived by reinventing himself decide what’s next?

Especially when personal priorities, like starting a family, collide with professional ambitions. Today, on Cold Call, I’m joined by Professor Reza Satchu and case protagonist Tim Ferriss to discuss the case, “Tim Ferriss, What Might This Look Like If It Were Easy?” I’m your host Brian Kenny, and you’re listening to a live taping of Cold Call coming to you from Klarman Hall on the campus of HBS, Harvard Business School. Make some noise, folks. All right, can we have a warm welcome for our guests? Reza Satchu teaches entrepreneurship at Harvard Business School, including the Founder Mindset and Founder Launch, both courses that he created. He is also a serial entrepreneur, having founded multiple highly successful ventures. Reza, welcome.

REZA SATCHU: Thank you very much. Thanks for having us.

BRIAN KENNY: Tim Ferriss, the subject of today’s case is a bestselling author, entrepreneur, speaker, and early stage investor. You may have heard that he hosts a podcast. Tim, welcome.

TIM FERRISS: Thanks. Thanks for having me. Hi, everybody.

BRIAN KENNY: It’s great to have you here. I’m a little nervous actually because your podcast gets a lot of listens, so I want to make sure that we do this right.

TIM FERRISS: I’m sure you’ll be fine. You have a better voice for radio. We were both commenting, the intonation and delivery. I thought it was so good. I was like, man.

BRIAN KENNY: Why don’t we just dive right in? Reza, I’m going to start with you. Can you tell us what drew you to Tim’s story? Why did you think it was a good subject for a case study, particularly for the Founder’s Mindset class, and what makes it particularly relevant for aspiring founders today?

REZA SATCHU: Yeah, so look, I think I was thrilled. Actually, my research associate who’s here, Denise Koller, came up with the idea of interviewing Tim. Initially, I thought, “Does this make sense?” The more I got to know Tim and study his work, his mindset is exactly in sync with some of the things that we’re trying to get our founders to think about, starting with, he imagines a world that doesn’t exist today. He imagines that there are things he can do that are different than are existing today. He imagines a space where he can actually think about something, take a series of actions, trust his judgment, and hopefully build something of consequence.

So many people stop at that first point, which is, how could I possibly do something different? It started really there, where I thought, “Here’s someone who has done many different things well, trusted his judgment.” Really, that’s a key part of being a founder.

BRIAN KENNY: Yeah. Tim, let me turn to you the case. Like any good HBS case, it opens up with you thinking pensively about what you’re going to do. You’re probably staring out a window looking at something. I’m wondering, actually, if you can take us back to where the case opens up, where you’re mulling through what your options are. You’ve got a lot of options right now and you’re thinking about what the best thing is. What was going on, what was your mindset at that time?

TIM FERRISS: Yeah, I was actually literally looking out, in Austin where I recorded my podcast. I would say fundamentally it was, number one, has this become a crowded red ocean where other people can do this, what I started off doing in 2014. If there are one or more people who can do what I can do, I’m like, “Well, this seems redundant.” I would prefer to do something that is more of a category of one, to borrow from the 22 Immutable Laws of Marketing. There wasn’t a financial pressure to stop. Certainly, there was a little bit of pressure to continue because it funds the foundation, it funds the angel investing, it pays for the bills and employees and so on.

But it was more a question of, is this the game I want to play? We’re all playing games past a certain point, past the lowest rungs on Maslow’s hierarchy of needs. Then, beyond that, it’s being aware of what game you’ve currently opted into, what are the rules, what are the wind conditions, the failure modes. Then, authoring something that hopefully stacks the deck in your favor. That’s a lot of what I was thinking about. The entire landscape had become too saturated.

BRIAN KENNY: Yeah, and so you described this in the case as blue oceans versus red oceans. Reza, if you can talk about, in the Founder Mindset framework, how does Tim’s approach to pattern recognition and assumption testing compare to other founders?

REZA SATCHU: I think there’s a critically important point on Tim’s mindset, and how I think it resonates with the Founder Mindset, is people think of committing to an idea as jumping off a cliff into shark-infested waters, and that somehow being a founder is full of risk, full of uncertainty. You close your eyes and you just hope and pray for the best. Okay, I can’t tell you how flawed that is. I’m a serial founder. I will tell you I think about risk all the time. I calculate risk and I’m not paralyzed by it. The key is actually making decisions in the face of risk. What Tim does with what he calls these assumptions or these experiments, he effectively is trusting his judgment to do some things.

Nothing terribly consequential, but enough to get data to figure out whether or not he should continue pursuing his curiosity. He gives himself permission to go down a pathway of his curiosity, whereas, most people never give themselves that permission because they just think, “How could I possibly have this idea when others have so many more resources?” I call it “small c commitments.” He calls it these “two-week experiments,” but it’s this idea that he’s willing to suspend disbelief that others haven’t thought of this idea, and that he’s willing to actually test his ideas and dip his toe in before he jumps in.

BRIAN KENNY: Yeah. Tim, for you, a lot of this began back when you wrote The 4-Hour Work Week, was that 15 years ago, give or take?

TIM FERRISS: Almost 20, 2007, back when I had hair.

BRIAN KENNY: Yeah, that book challenged a lot of assumptions at that time. I’m wondering what assumptions you were testing as you wrote that book, and how do you weigh the risks and opportunities of coming out with something that seems a little audacious?

TIM FERRISS: The first part I would say is simply asking questions that address some of the assumptions underlying traditional, let’s just call it, or conventional career planning. The deferred life plan. What would you do if you could not do that? If you could not rely on that. Which by the way is more and more relevant with some of the technologies that are coming. But if you couldn’t rely on that, exactly, as a social contract, what would you do? Then, it just led into lots of my own experiments. That was largely autobiographical. Then, teasing out the principles that allowed me to automate, and at the time use virtual assistants, that would be replaced by a lot of AI right now.

That’s the first part. It was testing assumptions, but not just in a theoretical capacity. It was saying, “All right, I tried this thing, it didn’t work. I did this, it did work. I did this, it kind of worked, and here’s how I got it to really work. Here’s how you might think about dipping your toe in the water.” One critical part of that book that I think sometimes gets missed is cultivating a bias towards action. There are these exercises at the end of almost every chapter called Comfort Challenges. It’s just doing things that are very uncomfortable socially. There’s really no risk involved.

This is not from the book, but my friend Noah Kagan talks about the Coffee Challenge, where people have to go in, order a coffee, and then ask for 10% off without giving any explanation, and just like, deal with that. It’s amazing. You see these people are like multiple-time founders or HBS grads, they’re pacing. They’re like, “Oh, it’s easy.” They’re pacing around the coffee shop for 30 minutes trying to build up the courage to do it. It’s like, “Yeah, that stuff helps.” From realizing that most stumbles or non-issues to begin with. In terms of presenting something that was contrarian, I first of all pitched the book.

It’s a long story as to how I even got to the book, because I never wanted to write a book, but it was turned down by something like 29 publishers, violently. Some of the rejection letters were worthy of framing. Then, Steve Ross and Heather Jackson, at Crown, which was an imprint of Random House at the time, my pitch had been polished after getting rejected 29 times, literally, this is not an exaggeration. They were like, “Sure, kid. We’ll pay you pennies on the dollar to try this.” Their downside risk was very low. I had, as a younger person, I was published when I was 29, but at that time it’s like, what are your advantages? You can take stock of your advantage.

At that time, it’s time, it’s speed, experimentation. You don’t have some permanent record of strikes that follows you around everywhere. I think you can afford to experiment. For me, it was ultimately an exercise in writing a book, and the only time it started to click was when I basically wrote it as I would write an email to two very particular friends after two glasses of wine. I threw out two drafts of that book, and then it unfolded, and that bought me permission to do a lot of other things.

BRIAN KENNY: Yeah, it worked out in the end, didn’t it?

TIM FERRISS: It did work out. It’s not the end yet, so we’ll see.

BRIAN KENNY: Reza, I had a chance to sit in on your class today, which was really interesting, and thank you for letting me do that. You talked a lot about failure, particularly in the beginning part of the class. What’s the Founder’s Mindset where it comes to being able to get rejected 29 times and still go back and ask for another publishing deal?

REZA SATCHU: Okay, so first of all, just on failure, I think human psychology, is you often overestimate your downside, and I think to Tim’s point, you also massively underestimate your ability to recover. People imagine failure as this terrible thing that, oh my God, if this happens, it will be awful. Certainly, sitting here with the HBS students, what you’re doing is looking left and right and wondering, “Oh, my God, these people are going to think I’m a failure.” When in reality they’re barely going to think about you at all, but people are really stressed about that.

I think the broader component around failure is not only do you overestimate what failure is, but by not putting yourself in positions of failure, two things don’t happen. One is you don’t learn. You don’t learn what happens through that failure. But the second thing is, I don’t know if this is what happened here, but people actually, when they look at someone who has stayed committed 29 times, I have this phrase which is like, magic happens when you commit, which is it’s not just you learn what you’re capable of. Other people show up precisely because they see the commitment. What people often misprice is that piece of the right tail upside.

I think failure is a wonderful thing. I think a life without failure is a terrible life. It’s just a life where you don’t learn what you’re capable of. I think there needs to be a fundamental reframing of failure. Tim, I’d love you to talk about your concept of these one-way doors, irreversible law, like how you price risk, what does risk actually mean to you?

TIM FERRISS: Yeah, I can speak to that. I also want to add something I left out of the question around The 4-Hour Work Week. There we go. I’ll let you take it. Just because people are rejecting your idea does not mean it’s a good idea. Just to state the obvious.

REZA SATCHU: That’s true.

TIM FERRISS: I agree with Paul Graham, Co-Founder of Y Combinator, who wrote an essay roughly around, the more labels you apply to yourself, the dumber you are. If you pride yourself on being contrarian, you’re actually just conforming to an anti-consensus. You’re actually still suffering from a really heavy form of bias. In my case, the reason I persisted through those 29 rejections was that the material that was going to be in the book, I had workshopped with, I don’t know, a thousand students at Princeton doing guest lectures at the invitation of my former professor. I had refined it, refined it like a stand-up comedian working on his 60-minute set, and I knew it worked.

REZA SATCHU: Right, so you had an informational advantage.

TIM FERRISS: I asked for feedback forms after every class. I had all these annoying pointed questions that students didn’t want to fill out. I knew that for a particular demographic it worked, and that’s why I persisted. If I had not had that data, I don’t think I would’ve persisted. I wouldn’t have had any grounds for plowing head in that way. Then, in terms of risk, I think there’s a lot to be said. I’m echoing Scott Galloway here, but choosing where you’re going to live and operate actually is a really important, sometimes more so than what you’re going to do. Moving to Silicon Valley was incredibly liberating because people fail all the time and they’re never counted out. I’ve invested in so many founders who failed the first time and then, boom.

REZA SATCHU: Back at it.

TIM FERRISS: Right? StumbleUpon, I was an advisor, didn’t work out. That was a zero for me as an advisor. But then, Garrett Camp a few months later was like, “Hey, I have this idea.” Turned it into Uber. People are never counted out. Being in an environment where that is the case matters a lot. It doesn’t have to be Silicon Valley, although that’s the most obvious. Risk for me, put simply, would be the probability of an irreversible negative outcome. There are some cases where that’s part of the calculus, but typically, I thought about making a journal. I seriously contemplated doing this because everyone’s making a journal now, but I went to the bookstore, I was like, “There are too many journals, I’m not going to do it.”

But the journal was going to be called “worries that mostly didn’t happen.” It’s just like you just write down what you’re worried about and then you look back three months later, and again, none of that actually mattered. The cost of “failure” is very low for most things. You can also get a signal, positive or negative, go or no-go, pretty quickly if you’re methodical about it. I try to view, reframe failure, as scientific feedback. You have a hypothesis, you test it, it didn’t pan out, still valuable. If you’re optimizing for learning and relationships that transcend any given project, experiment, company, job, et cetera, those things snowball over time.

If you’re keen on doing short-term experiments but long-term greedy, it’s very hard to lose, in my opinion. From what I’ve seen, and this is based on Silicon Valley, so it’s maybe anomalous, but it’s really hard to fail over the long term.

REZA SATCHU: The amazing thing about this failure point is if you just think about two different career trajectories, one is a more traditional career trajectory. Let’s pick on consultants because, why not? There’s no real risk of failure. You’re going to get 95 things out of a hundred right on that path. On the Founder path, you are getting most things wrong. You’re asking people for money, they’re saying no. You’re asking customers to transact with you, they’re saying no. You’re trying to hire people, they’re saying no. You’ve got no resources. You’re constantly surrounded by a life of failure.

You’ve just got to decide which life sounds better. What you suddenly realize is, wow, well, a life without failure, it’s hard to imagine having the impact that you all want to have, or having the return that you all want to have. I really think this point around risk really ties into failure, which is first of all, you need to reframe risk as a really great thing. Without risk, there’s no return. Risk is a good thing. It is not what you immediately think of, which is, “Oh, I want to stay away from it.” You need risk. Okay? What that doesn’t mean is that you’re jumping off a cliff. What it means is you understand how to operate in terms of risk.

You need to incorporate some of the frameworks that you’ve talked about in class today to measure and calibrate it. But Tim’s not writing these books if he’s not willing to encounter risk.

TIM FERRISS: Yeah, the 4-Hour Body, still recovering from some injuries from that one, 2010. Just had a surgery on this elbow as a result of that book.

REZA SATCHU: Everyone must have thought that was a crazy idea.

TIM FERRISS: It was crazy. But to use the 4-Hour Body as an example, the 4-Hour Work Week bought me permission to experiment outside of that lane, and so I did the 4-Hour Body in totally different category. Because the upside of that was so high if it opened the door to me writing books on any subject. The downside was that book doesn’t do well, and I go back to milking this 4-Hour, whatever the hell work week. The downside risk was very, very limited. I would also say that I think my experience with great schools, my experience with analytical people in general, is that they’re very good at thinking about all the possible downsides of doing the new thing or doing the “risky thing”.

But they don’t spend as much time thinking about the cost of inaction or the status quo or taking the safe route. If you telescope out six months, a year, three years, five years, what are the emotional costs, financial, maybe relational, et cetera. It turns out when you start to look at these two options with equal weight, that the potentially safer route is just as fraught with all sort of problems as the supposedly risky route. Then, it’s like, “All right, I might as well do the weird thing first.”

BRIAN KENNY: Did you ever worry about your brand though, the Tim Ferriss brand? If I do something that’s too contrarian, I may lose some of my brand cachet.

TIM FERRISS: I don’t think about brand really at all, which isn’t to fault anyone who does, but I think brand is one of those words that can be a siren song for lots of decisions that compromise. I don’t want to say necessarily integrity and values, although it can be that, but you can be captured by, in my case, like an audience who rewards you for your most outlandish comments. If you follow that incentive structure on something like YouTube, you can wear a mask for so long that you become that mask. I’ve seen that happen to people, and you can’t hit control Z on that very easily, so I don’t think about brand. I pay a lot of attention to truly following my curiosity. When I do say a six, I do these two week experiments, but they’re generally within the context of a six to 12-month project. When I’m in that six to 12-month project, I am all in. I am completely saturated in it. I just find that there are a lot of ways to approach this. There’s no one way for everybody, but most of the hiccups along the way are just little toe stubs. But you have to get used to taking the hits. In other words, it’s like, if you were to go to a boxing class and you’ve never done boxing before and you get hit in the liver with a punch, it’s not even a hard punch. It’s going to be really shocking and unpleasant. If you do it for six months, you’ll be like, “Okay, yeah, I’m going to get 50 of these today. It’s fine.” You get over it, but you have to train your immune response, your stress response to this stuff. The only way to do that is by getting out there and trying stuff.

REZA SATCHU: Brian, this is what’s so valuable to Founders, is exactly this, which is what they’re getting is hit all the time, but they’re learning that they can recover much faster through those hits.

TIM FERRISS: Yeah. Could I add one more thing?

REZA SATCHU: Yeah, of course.

TIM FERRISS: I’ll give you an example. I remember the first time that I got, sadly, this is just a tax in the US, my first frivolous lawsuit, I got sued by somebody who was completely, it’s laughably ridiculous. I was so stressed out, I couldn’t sleep, and my publisher was involved, all this craziness. It was filed by the law firm that sued Subway for having 11 and a half inch foot long subs. So I’m dealing with all this and it’s tearing me up inside. Then, I was having a conversation with this friend of mine who’s been on multiple public boards. He’s in private equity for a super long time, very, very good investor. He’s like, “What?” He’s like, “This is the first time you’ve been sued.” He’s like, “I should sue you.” He’s like, “Welcome to the club.” He’s like, “What are you so upset about?” I was like, “What are you talking about?” I tried to justify it, and he’s like, “Ah. It’s fine.” I was like, “Oh, okay.” You just realize that a lot of the things you might contemplate now that you think are very big, huge problems, you can fix. A lot of it is just par for the course.

REZA SATCHU: What do you think of this right to recover or what do you think human psychology is around recovery? Do people underestimate or overestimate their ability to recover?

TIM FERRISS: I think it depends a lot on who you’re talking to, right? It’s like, if we’re talking to a bunch of refugees who had made hard choices. Then, I would say they probably accurately estimate their adaptiveness.

REZA SATCHU: Ability. Yeah.

TIM FERRISS: Their ability to adapt. I would say people who have, and this was me for a long time, executed to plan in a system where the rules are known, it’s more or less complete information, like higher education. It’s like, “Okay, great, you’re on the dean’s list, you’re summa cum laude, or whatever.” That those people underestimate their resilience, but I don’t actually think they’re wrong, because to develop the resilience you have to build some scar tissue. The only way you do that is by getting on the field. This sounds all abstract. It’s like, “No, okay, you want to change the world and build a billion-dollar company doing X?” It’s like, “All right, go talk to 10, go pitch 10 customers next week and ask them for money.

As a dry run to get prepayment that will fund X, Y, or Z.” But don’t hide, and then I’m quoting Seth Godin, “But don’t hide behind the big.” Get out there and it’s going to be messy.

BRIAN KENNY: Reza, I want to talk, so much of the case centers around optionality and all the options that Tim had in front of him, we talked about that a little bit upfront. I’m wondering, once you’ve achieved a certain level of success, a lot of opportunities open up. As a Founder, how do you sort through that? How do you think about what’s worth pursuing, what you shouldn’t pursue? What’s the thought process there?

REZA SATCHU: Yeah, so it’s interesting. In my life, as someone who’s founded a few businesses, in some ways, the most recent businesses are harder, surprisingly. One would say, “Well, it’s easier because you’ve got more resources, more expertise, you have less hunger, and you have much more options. It’s not as critical that it has to succeed.” I teach and I found a business at the same time. That’s crazy. Most people would say that is not an optimal way to found a business. Whereas, my first couple of businesses, there’s no way I’d be teaching and founding a business. I’d be fully focused on founding.

I think this idea that it gets easier, it might get easier from an expertise perspective, but suddenly you’ve got what I call the curse of optionality, which is you’ve got a number, and Tim, you’re facing some of this right now, frankly, this paradox of choice, which is precisely because of the success you’ve had you’ve got a whole bunch of choices. He mentioned Seth Godin, who’s a wonderful writer, who we interviewed for the case, and he said to Denise and me that we need to lock Tim in a room or in a cabin, and he needs to pick an option. Of course, what he was saying was that the world will be a much better place if Tim commits to something. As opposed to maximizing all of his options.

I do think this curse, and for the students, people listening, I think that many of you will fall into this trap of preserving options for far too long and not knowing what you’re capable of when you commit. I’ve not had money and I’ve had money. Not having money is somewhat liberating because you just know what you need to do. When you have options, and those options could be a Harvard Business School degree, you suddenly start thinking, “Well, maybe I can preserve those options for a very long time.” I’m curious, Tim, I would ask you this question, which is you’ve got a whole bunch of options ahead of you. Here’s what I know to be true, is if you committed to one, I’m sure it will be far more impactful than if you preserve all of them.

TIM FERRISS: Yeah, that’s true. I agree with that, but I would also say a few things. Number one is that you can validate or invalidate something really quickly. We were talking about this a bit earlier, but I was chatting with a student who was talking about maybe the safer route to finance and then less safe perhaps in entertainment, film potentially. I was saying, I’m saying, “All right, you know what’s going to really get attention, is if you’re an HBS grad who offers to shadow a show runner or a producer in pre-production on a movie, and you’re like, “Nothing is beneath me. Cleaning toilets, getting your coffee, I don’t care.'”

It’s like, “All I want to do is observe some deal making and see what goes into making a film.” It’s like, “You can figure out if that is actually your dream or not very, very quickly. You might be completely allergic to it, but you can figure that out after a week of being in the pre-production office.” That’s number one.

REZA SATCHU: But are you also suggesting that because that’s a differentiator, meaning, there’s something that it says about you, that you’re willing to do that?

TIM FERRISS: Here’s my experience. Even though you might feel there’s very little time and a big rush, there’s not a big rush. You can take time to have these little detours and try things. The second is that even though I’m doing some different things, let’s just say angel investing newsletter foundation focused on mental health therapeutics, nonprofit, blah, blah, blah, blah, blah. There’s actually a way in which they reinforce one another. I will use, say, the podcast to interview scientists based on science I’m interested in to determine if I think they’re a good candidate for the foundation, or potentially, it doesn’t have to be a scientist. If I find that their personality is compatible enough and their idea is compelling enough that I want to make an investment in their company. I can use that as a discovery mechanism then for sourcing. I would say, also it depends on how much… Preserving all of your options also is just an illusion. You can’t really do that. The nature of making a decision, it’s like incision, decision to cut away. You are by definition cutting off a lot of paths, which I do for six to 12 months at a time. But you can have a few things, in my case, running at the same time in parallel. I would say optionality might not be all you think it is. If I look at hundreds of people I’ve interviewed on the podcast who are by any measure top performers in their fields, one of the most common comments or concepts that comes up is the power of positive constraints. Positive constraints, commit. It doesn’t have to be commit forever. It shouldn’t probably be commit forever, unless you’re the person who knows at age five that you want to do X. If you’re that, I don’t know, maybe you wouldn’t be here.

REZA SATCHU: Positive constraints means cutting off options, in some sense?

TIM FERRISS: It means cutting off options, or it could be anything. If you’re writing, it could be a space or page constraint. It could be, I have to write this all in third person or first person.

REZA SATCHU: Well, it’s also your comment around, if I’ve got a problem, I will only solve it by taking something away.

TIM FERRISS: Right, so in the case of the podcast, I found myself starting to drag my feet because it’s a very saturated marketplace. One of my key advantages that I had early on, besides just starting pretty early in 2014, was my research and the ability that I had to dig and find things that were interesting. Now, you can go in ChatGPT and say, “Give me 10 questions in the style of Tim Ferriss or Lex Friedman or Joe Rogan interviewing this person.” Boom, you’ll get good answers. That advantage has effectively disappeared, and there are a lot of ways to potentially respond to that. But for me, number one, I’m generally not looking for the cutting edge. I’m looking for dull edge.

I want to see some proof of concept before I do angel investing or before I do some hare-brained thing, like make a card game, which some of you may have or not. That’s sitting up at the top for anybody who wants a copy. I think that fundamentally a lot of it comes down to asking yourself, how do you maximize for… I know this is, again, it’s so simple, but if you maximize for learning and relationships that transcend whatever that single project or job is, this is particularly effective if you are in a place like San Francisco. I don’t want to sell San Francisco. It’s pretty dirty and filthy. But I think if you were going to choose projects and you decided as a thought exercise to rank order the parameters as who, like who am I directly observing and working with? Then, where, and then what/sector, that actually comes last, I think you could end up with some pretty interesting options on the menu.

BRIAN KENNY: We haven’t talked about impact, but I know that’s an important part of the thing that you cover in Founder’s Mindset. Can you talk a little bit about the idea of thinking about impact at the outset and not at the end of the journey?

REZA SATCHU: I think so many people fall into this trap. I think I fell into this trap early in my career, which is my life is going to be in these stages. The impact stage will be that last piece of my life when I’ve learned a lot, when I’ve had the benefit of resources, all these sorts of things. The problem is there’s two problems. One is you may or may not be around for that last piece.

BRIAN KENNY: Never know.

REZA SATCHU: But the second point is it turns out that actually having impact along the way, and I love the way you describe it, which is start with the small things. Start with the people in your life that you’re… We all have these, especially here, have these visions of grandeur around having massive impact. Well, I’d say the most important way to do that is to actually start living a life of impact right away and on the small things. I think that, Tim, when you talk about, so what I view learning, what I view learning as, because a lot of people talk about you want to maximize learning, which I completely agree, and I’d be curious how you define learning.

Okay, so I’m going to propose what my definition of learning is, and you tell me whether this, because I think it’s an important concept because learning is… If you had to say, what is the thing that is going to most correlate with impact, it would be learning. He who learns, he or she who learns the most is going to attract the most credibility, resources such that they can have the impact that they most desperately want. I define learning in the age of AI as the spot where you’re making… it’s all about decision making. Meaning, the trait we are most trying to learn is judgment. Judgment occurs when you’re making consequential decisions that you’re accountable for.

You must live a life where you’re pushing yourself to make decisions, some of which will be wrong, some of which will be right, in order to build the thing we most want, which is judgment. Okay, so I’m curious to know your thoughts about that.

TIM FERRISS: Learning, there’s how to learn, and then there’s what to learn. If you’re looking at say, who to work with, and then the where, and then the what, right? There are certain skills that are not going to transfer. It’s like, okay, if you’re in the waste management business and you’re understanding the ins and outs of waste management, I’m just making that up because I like unsexy stuff, that may not transfer to your hot shot AI startup for whatever, customer service. But if you are observing, this is an old school example, like a Wayne Huizenga.

REZA SATCHU: Yeah, Wayne Huizenga. They don’t know who Wayne Huizenga is.

TIM FERRISS: I know.

REZA SATCHU: You and I know who Wayne Huizenga is.

TIM FERRISS: I know, waste management, then Blockbuster, which went extinct back in the Pleistocene era, but that guy was a master deal maker. If you’re able to watch someone acquiring dozens and dozens of companies, and how that entire dance is woven, that transfers. If you’re learning how to communicate, let’s just say, I’m making this up, you work for Cards Against Humanity. This is a very popular game as some of you may know, they were really, really good at PR stunts. If you work at that company when it is small and you’re involved with all of those PR stunts, which fundamentally are thinking about positioning and differentiation, that will apply to everything. It’s just asking yourself, where could this transfer? Where could this apply? Then, that’s the stuff that you focus on. For me, it’s in a sense meta skills, that if you were to copy and paste, you take somebody, look, it doesn’t matter.

Well, I’ll give you actually maybe a more contemporary example, like Jeff Bezos. All right. What is Jeff Bezos’ superpower? I would say that it is having longer time horizons than almost everybody else, and defending and justifying and reiterating that in every shareholder letter. He trained Wall Street like a domesticated puppy, like a puppy.

REZA SATCHU: From day one, yeah.

TIM FERRISS: Talk about just incredible persuasion and the pro sleight of hand and also just business mastery. But the point is, if you have a longer time horizon than other people, that’s a huge competitive advantage also in and of itself. If you can be around someone who exemplifies that, because I can say that, and you’re like, “Okay, I got it.” But it’s like, do you really? You need to see how that is emphasized over and over again. Or, like a Herb Kelleher at Southwest. Would I have loved to have worked for that guy? Would I have quit my tech job to work for him? Absolutely, because such a maniacal focus on being the low cost airline.

I remember he was interviewed at one point and he said to the journalists, because they were saying how hard it was, what he did, and he’s like, “No, you can do my job.” Then, he’s like, “All right, give me a situation.” They gave him a situation. He’s like, “All right, does that help us to be the low cost airline or not?” They’re like, “No.” He’s like, “Yeah, that’s a no.” He’s like, “Okay, next one.” He’s like, “Yeah.” If you have the focus, but you need to be around people who are doing that and living it so you can see it in different contexts. This is going to sound bizarre because I’m thinking about adopting another dog.

But there’s an expression in dog training, which is basically if the dog hasn’t done it, say a behavior, shaping a behavior in 20 different locations, 20 different durations, they don’t have that behavior. It’s not durable. Humans are the same. It’s conditioning. Having the opportunity to work with someone where you see certain characteristics exemplified; certain behaviors, certain principles enacted that can be applied to different businesses, man, I think that’s an incredible shortcut. But you and I have different perspectives on this. I think working for a startup’s a fantastic way to learn on someone else’s dime with the understanding that-

BRIAN KENNY: That’s our youngest audience member, by the way.

TIM FERRISS: Yeah. Start them young. Start them young.

REZA SATCHU: It’s true. What I’d say, I think just, look, I think the question is, in the age of AI, what are the traits that we can teach people? I think that the challenge is that things like memorization and observation are far less valuable. What is valuable is this elusive thing called judgment. The real question is, how do we get it? I think, yeah, you can get it by watching someone else, but how you really get it is by doing it yourself. Actually being in the arena, making those decisions. One of the things you said, Tim, which is very interesting to me, because I have a similar phrase, when you said you have a bias for action.

I have a phrase which is, if in doubt, act, which immediately people say, “Well, wait, Reza, you don’t know what you’re doing, you’re going to act?” No, the reason I say that is because so many people are paralyzed by imperfect or uncertain information, and so they’re like deer in headlights. What I suggest is, even if you’re going to stay the course, train yourself to make a decision that you’re actually staying the course, which is a bias for action. I’m curious how you think about, bias for action is, it feels risky. I’m curious how you view that.

TIM FERRISS: What I would say is I have a tendency… My mom literally got me a shirt that says, ”Wait a second, let me overthink this.” My tendency is to, I don’t want to say perseverate, but over consider the ramifications of a lot of decisions. It’s been a practice of conditioning myself to be like, all right, what if I tried what Reid Hoffman of LinkedIn and so on has done, where he wants to enable his chief of staff to act quickly enough that they roughly get things wrong 10% of the time. That’s literally a guideline that he uses with his chief of staff.

He says 10% footfall, which is a little confusing because it’s a tennis reference. Anyway, but I think applying that to your own life where you’re like, all right, what can I put on automatic, just no decision autopilot default, number one, where can I just completely remove decisions? Sometimes that’s with diet, exercise. You don’t want to get up in the morning and decide which of 20 toothpaste tubes you’re going to use. You have your toothpaste and you just deal with your toothpaste. Similarly, you could extrapolate that and apply it to giving employees autonomous decision-making power and creating a culture where you actually reward screw-ups.

I literally met with, I was having a blood draw this morning because I’m in Boston for proteomics assay. Anyway, it’s a long story. But they have a dedicated discord within the company for celebrating bleep-ups basically. That are not egregious. It’s also like, all right, how do we not do this again? But people get rewarded for ambition, mistakes of ambition, not mistakes of sloth, which is straight from Machiavelli, so I’m not sure how I feel about that.

But in any case, I don’t know about also… I got stuck on the AI stuff again, because I don’t know, I wish I could give everybody and myself a strategy for making yourself AI proof. I don’t know what that looks like.

I think though you can make a decision about, am I going to use these tools or am I going to stick my head in the sand and try to find a way around them? I think probably the way to go for it is spend your evenings for two weeks vibe coding and messing around with AI, so that you have some idea of how you might utilize it. Because within two or three years, we’re going to have multi-billion dollar companies or billion-dollar companies with one to three employees, I’m very confident in that. They’ll just use agents to fill a lot of roles, like CFO and so on. People are already doing this. I wouldn’t get too hung up on that.

Although I would say, if I were to play the counterpoint, that the soft skills that I was mentioning earlier, negotiating, deal-making, this is a very intrinsically human interaction.

REZA SATCHU: Human thing.

TIM FERRISS: It’s very rare that you’re just going to be able to send pitch emails with the deal structure and you’re like, “Yes or no, thumbs up?” With this emoticon based on my AI chatbot, like, “Great. Let’s do a deal.” Typically, not how it works, especially as the stakes get bigger, which don’t mean they’re huge, that they’re just consequential for whoever you’re dealing with. That stuff I don’t see going away anytime soon.

BRIAN KENNY: I want to give time. We’re coming close to the end of our time. I’ve got one more question for each of you, but before we do that, Tim, maybe you want to tell people about your latest venture? Because I think there are some takeaways, some giveaway items.

TIM FERRISS: Yeah, if people want, so this is a very off menu thing.

BRIAN KENNY: It’s just like the Oprah Show. You’re going to get something to take with you.

TIM FERRISS: Yeah, exactly. It’s not a car, but it’s something else. I ended up collaborating with this guy, Elan Lee, who’s one of the world’s best game designers for the last two years to create a card game for off-screen social interaction. That’s my current project, is a card game of all things. I could explain why I chose that, but the biggest one was the who. This Elan Lee, where I was like, “I would pay to just hang out with this guy.”

He’s such a soulful, deep thinker, who’s ethical and also happens to be a polymath, top 1% in multiple fields. I was like, “I just want to steep myself in whatever magic juju this guy has.” That’s how fundamentally I made the decision. Yeah, there are games up there, it’s called COYOTE. Then, beyond that, I do have an 800-page draft of a book. That’s not an overstatement. I’ll be whittling that down over the next six months probably. That’s been like eight years in the making. It’s been sitting back there for a long time. There’s other stuff going on.

BRIAN KENNY: That’s awesome. Now, this has been a great conversation. I knew it would be. I was so excited to do this today. Before I let you go, I’ll ask the same question of each of you, and I’ll start with you, Tim, and I always give the professor the last word because it’s Harvard Business School, but it’s a pretty simple question.

TIM FERRISS: Reza is pretty good at getting the last word anyway.

BRIAN KENNY: I think that’s true.

REZA SATCHU: That’s true. That is definitely

BRIAN KENNY: If you just think about the case, you’ve lived it, what lessons do you think emerging founders should take from the case about navigating similar inflection points in their own journey?

TIM FERRISS: Let’s see. I’m going to give credit to a mentor of mine named Ed Zschau. He was a professor of mine at Princeton, taught really the first entrepreneurship class that I’m aware of, “High-tech Entrepreneurship,” ELE 491. Still have all my notes from the class. He used to teach at HBS and then jump-started this entrepreneurship program at Princeton. He was congressman from Silicon Valley, former competitive figure skater, took a couple of companies public. Was one of the first, if not the first computer science teacher at Stanford, even though he had no computer science background. It was like somebody else dropped out and they’re like, “Can anybody else teach this class? He was like, “Oh, I’ll figure it out.” Back in the day. In his last class, I think I’m getting the name of this song right, but he actually gets up and he sings this song. I’m going to do it my way. The whole point is everybody’s making up everything by and large. There is no one right way to do it. I think that what I would hope people to take from my very bizarre case study, and I say that, I couldn’t have been prouder and happier with how everybody put it together, Denise and Reza and so on, is that you don’t have to follow the prescription, whatever the prescription is. You don’t have to meet the expectations, whatever the expectations are. You just don’t have to do it. There are a lot of ways to improvise and zig and zag. As long as you’re not too calcified around what you consider your identity. You just have to be really careful with painting yourself into a corner with that. That’s what I would hope people to take from it, is just there is a lot of room to improvise and maneuver. People ask me a lot, for instance, I’ve done these 800 plus interviews on the podcast, and they’re like, “What are the commonalities?” I’m like, “The greatest commonality is there are no commonalities.”

It’s like for every incredible writer who gives me one set of advice, I sit in front of the screen, even if it’s blank for 10 hours a day, chained myself to the desk. To, B.J. Novak of The Office and movies and all sorts of stuff, he was like, “Yeah, I really need to get into the mood.” It’s like, “I’ll have my cappuccino, I’ll read the paper, I’ll do this thing. I really need to be in the right state to write.” They’re both doing amazing jobs, and they have diametrically opposing advice, which means you can figure out what rules and what stories work for you. I would just say mess around. You have your whole life to be safe and conservative and not politically. You get the idea. Like color within the lines. I guess you could have the rest of your life to be conservative too politically. But the point is, there will never, in my opinion, be a better time for you guys coming out of HBS to just embrace your weird self and try some of the stuff that is going to get harder to do later.

REZA SATCHU: Look, I think that’s extremely well said. Tim, when we wrote this case study, in some ways it’s probably the longest case study because he’s got so many things going on. My students are probably like, “This is a 20-plus page story.” It’s everything from dancing, to an author, to podcasts, to all sorts of things. If I had to summarize it, I’d want two takeaways. One is, live a life full of curiosity and allow yourself to explore the things that you’re curious with. Whether that’s these experiments, small C commitments, just suspend disbelief and trust your judgment to actually explore things that you’re curious in. The upside is far greater than the downside. That’s the first point.

The second point is, I really think Tim’s risk framework is very interesting. In some ways you hear a story and you immediately think, “Well, this guy is embracing risk at every turn.” It’s actually the opposite. He understands that he has to live a life with risk, but he’s actually thinking really hard about how to calibrate it. The way he does that is by actually understanding that his downside is nowhere near as bad as we all think it is. It’s defining his fears, which allows him to hopefully do something extraordinary because he’s shifting what the outcome could be.

I think that is really, I would say those are, trust your curiosity and embrace risk, but calibrate it appropriately and understand that, especially coming out of a school like Harvard, your downside is nowhere near as bad as you think it is.

TIM FERRISS: I’d love to add just a few things real quick. The risk mitigation stuff and thinking about that, if people are interested, I wrote these a long time ago, but it’s a two-part blog post series called How, I think it’s just “How I Created a Real World MBA.” Related to how I tiptoed my way into angel investing.

REZA SATCHU: Well, this is your angel investing.

TIM FERRISS: I think that’s worth, I think people in this room might find that an interesting read. The second is really study the outliers. Because if anyone has done it, there is the possibility that you could also do it or chart your own path. A book that you might not expect, it’s one called The Art of Possibility, I think the author’s last name, it’s by a husband and wife duo, Zander, Z-A-N-D-E-R. It’s very fast read, amazing book. There are a lot of book recommendations I could give, but that’s a fast one that I would encourage people to check out.

Really study the outliers, like Yvon Chouinard, the early chapters, the early chapters, or if you think of someone who’s a risk-taker, like Richard Branson, read Losing My Virginity. It’s like at every turn that guy is hedging risk and minimizing and mitigating risk. It’s remarkable how good he is at capping downside. I would just say, study the outliers. There are a lot of ways to tiptoe into things to figure out a signal very, very quickly at low cost.

BRIAN KENNY: I think that’s a good note to end on. Tim, Reza, all of you, thank you for joining me on Cold Call.

REZA SATCHU: Thanks, Brian.

TIM FERRISS: Thanks.

BRIAN KENNY: If you enjoy Cold Call, you might like our other podcasts: Climate Rising, Coaching Real Leaders, IdeaCast, Managing the Future of Work, Skydeck, and Think Big, Buy Small. Find them wherever you get your podcasts.

If you have any suggestions or just want to say hello, we want to hear from you. Email us at [email protected]. Thanks again for joining us. I’m your host Brian Kenny, and you’ve been listening to Cold Call, an official podcast of Harvard Business School and part of the HBR Podcast Network.