{"id":3730,"date":"2025-10-15T06:24:09","date_gmt":"2025-10-14T22:24:09","guid":{"rendered":"https:\/\/moresourcing.com\/tim-ferriss-at-a-career-crossroads-how-should-he-shape-his-next-chapter\/"},"modified":"2025-10-15T06:24:09","modified_gmt":"2025-10-14T22:24:09","slug":"tim-ferriss-at-a-career-crossroads-how-should-he-shape-his-next-chapter","status":"publish","type":"post","link":"https:\/\/moresourcing.com\/ja\/tim-ferriss-at-a-career-crossroads-how-should-he-shape-his-next-chapter\/","title":{"rendered":"How Should He Shape His Next Chapter?"},"content":{"rendered":"<p><\/p>\n<div id=\"transcript-section\">\n        <!-- let's remove the TRANSCRIPT header --><\/p>\n<p>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\u2019s next?<\/p>\n<p>Especially when personal priorities, like starting a family, collide with professional ambitions. Today, on Cold Call, I\u2019m joined by Professor Reza Satchu and case protagonist Tim Ferriss to discuss the case, \u201c<a href=\"https:\/\/store.hbr.org\/product\/tim-ferriss-what-might-this-look-like-if-it-were-easy\/825091?sku=825091-PDF-ENG\" target=\"_blank\" rel=\"noopener\">Tim Ferriss, What Might This Look Like If It Were Easy<\/a>?\u201d I\u2019m your host Brian Kenny, and you\u2019re 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.<\/p>\n<p>REZA SATCHU: Thank you very much. Thanks for having us.<\/p>\n<p>BRIAN KENNY: Tim Ferriss, the subject of today\u2019s case is a bestselling author, entrepreneur, speaker, and early stage investor. You may have heard that he hosts a podcast. Tim, welcome.<\/p>\n<p>TIM FERRISS: Thanks. Thanks for having me. Hi, everybody.<\/p>\n<p>BRIAN KENNY: It\u2019s great to have you here. I\u2019m a little nervous actually because your podcast gets a lot of listens, so I want to make sure that we do this right.<\/p>\n<p>TIM FERRISS: I\u2019m sure you\u2019ll 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.<\/p>\n<p>BRIAN KENNY: Why don\u2019t we just dive right in? Reza, I\u2019m going to start with you. Can you tell us what drew you to Tim\u2019s story? Why did you think it was a good subject for a case study, particularly for the Founder\u2019s Mindset class, and what makes it particularly relevant for aspiring founders today?<\/p>\n<p>REZA SATCHU: Yeah, so look, I think I was thrilled. Actually, my research associate who\u2019s here, Denise Koller, came up with the idea of interviewing Tim. Initially, I thought, \u201cDoes this make sense?\u201d The more I got to know Tim and study his work, his mindset is exactly in sync with some of the things that we\u2019re trying to get our founders to think about, starting with, he imagines a world that doesn\u2019t 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.<\/p>\n<p>So many people stop at that first point, which is, how could I possibly do something different? It started really there, where I thought, \u201cHere\u2019s someone who has done many different things well, trusted his judgment.\u201d Really, that\u2019s a key part of being a founder.<\/p>\n<p>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\u2019re going to do. You\u2019re probably staring out a window looking at something. I\u2019m wondering, actually, if you can take us back to where the case opens up, where you\u2019re mulling through what your options are. You\u2019ve got a lot of options right now and you\u2019re thinking about what the best thing is. What was going on, what was your mindset at that time?<\/p>\n<p>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\u2019m like, \u201cWell, this seems redundant.\u201d I would prefer to do something that is more of a category of one, to borrow from the <em>22 Immutable Laws of Marketing.<\/em> There wasn\u2019t 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.<\/p>\n<p>But it was more a question of, is this the game I want to play? We\u2019re all playing games past a certain point, past the lowest rungs on Maslow\u2019s hierarchy of needs. Then, beyond that, it\u2019s being aware of what game you\u2019ve 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\u2019s a lot of what I was thinking about. The entire landscape had become too saturated.<\/p>\n<p>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\u2019s approach to pattern recognition and assumption testing compare to other founders?<\/p>\n<p>REZA SATCHU: I think there\u2019s a critically important point on Tim\u2019s 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\u2019t tell you how flawed that is. I\u2019m a serial founder. I will tell you I think about risk all the time. I calculate risk and I\u2019m 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.<\/p>\n<p>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, \u201cHow could I possibly have this idea when others have so many more resources?\u201d I call it \u201csmall c commitments.\u201d He calls it these \u201ctwo-week experiments,\u201d but it\u2019s this idea that he\u2019s willing to suspend disbelief that others haven\u2019t thought of this idea, and that he\u2019s willing to actually test his ideas and dip his toe in before he jumps in.<\/p>\n<p>BRIAN KENNY: Yeah. Tim, for you, a lot of this began back when you wrote <em>The 4-Hour Work Week<\/em>, was that 15 years ago, give or take?<\/p>\n<p>TIM FERRISS: Almost 20, 2007, back when I had hair.<\/p>\n<p>BRIAN KENNY: Yeah, that book challenged a lot of assumptions at that time. I\u2019m 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?<\/p>\n<p>TIM FERRISS: The first part I would say is simply asking questions that address some of the assumptions underlying traditional, let\u2019s 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\u2019t 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.<\/p>\n<p>That\u2019s the first part. It was testing assumptions, but not just in a theoretical capacity. It was saying, \u201cAll right, I tried this thing, it didn\u2019t work. I did this, it did work. I did this, it kind of worked, and here\u2019s how I got it to really work. Here\u2019s how you might think about dipping your toe in the water.\u201d 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\u2019s just doing things that are very uncomfortable socially. There\u2019s really no risk involved.<\/p>\n<p>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\u2019s amazing. You see these people are like multiple-time founders or HBS grads, they\u2019re pacing. They\u2019re like, \u201cOh, it\u2019s easy.\u201d They\u2019re pacing around the coffee shop for 30 minutes trying to build up the courage to do it. It\u2019s like, \u201cYeah, that stuff helps.\u201d 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.<\/p>\n<p>It\u2019s 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, \u201cSure, kid. We\u2019ll pay you pennies on the dollar to try this.\u201d Their downside risk was very low. I had, as a younger person, I was published when I was 29, but at that time it\u2019s like, what are your advantages? You can take stock of your advantage.<\/p>\n<p>At that time, it\u2019s time, it\u2019s speed, experimentation. You don\u2019t 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.<\/p>\n<p>BRIAN KENNY: Yeah, it worked out in the end, didn\u2019t it?<\/p>\n<p>TIM FERRISS: It did work out. It\u2019s not the end yet, so we\u2019ll see.<\/p>\n<p>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\u2019s the Founder\u2019s Mindset where it comes to being able to get rejected 29 times and still go back and ask for another publishing deal?<\/p>\n<p>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\u2019s 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\u2019re doing is looking left and right and wondering, \u201cOh, my God, these people are going to think I\u2019m a failure.\u201d When in reality they\u2019re barely going to think about you at all, but people are really stressed about that.<\/p>\n<p>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\u2019t happen. One is you don\u2019t learn. You don\u2019t learn what happens through that failure. But the second thing is, I don\u2019t 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\u2019s not just you learn what you\u2019re capable of. Other people show up precisely because they see the commitment. What people often misprice is that piece of the right tail upside.<\/p>\n<p>I think failure is a wonderful thing. I think a life without failure is a terrible life. It\u2019s just a life where you don\u2019t learn what you\u2019re capable of. I think there needs to be a fundamental reframing of failure. Tim, I\u2019d 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?<\/p>\n<p>TIM FERRISS: Yeah, I can speak to that. I also want to add something I left out of the question around <em>The 4-Hour Work Week<\/em>. There we go. I\u2019ll let you take it. Just because people are rejecting your idea does not mean it\u2019s a good idea. Just to state the obvious.<\/p>\n<p>REZA SATCHU: That\u2019s true.<\/p>\n<p>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\u2019re actually just conforming to an anti-consensus. You\u2019re 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\u2019t 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.<\/p>\n<p>REZA SATCHU: Right, so you had an informational advantage.<\/p>\n<p>TIM FERRISS: I asked for feedback forms after every class. I had all these annoying pointed questions that students didn\u2019t want to fill out. I knew that for a particular demographic it worked, and that\u2019s why I persisted. If I had not had that data, I don\u2019t think I would\u2019ve persisted. I wouldn\u2019t have had any grounds for plowing head in that way. Then, in terms of risk, I think there\u2019s a lot to be said. I\u2019m echoing Scott Galloway here, but choosing where you\u2019re going to live and operate actually is a really important, sometimes more so than what you\u2019re going to do. Moving to Silicon Valley was incredibly liberating because people fail all the time and they\u2019re never counted out. I\u2019ve invested in so many founders who failed the first time and then, boom.<\/p>\n<p>REZA SATCHU: Back at it.<\/p>\n<p>TIM FERRISS: Right? StumbleUpon, I was an advisor, didn\u2019t work out. That was a zero for me as an advisor. But then, Garrett Camp a few months later was like, \u201cHey, I have this idea.\u201d Turned it into Uber. People are never counted out. Being in an environment where that is the case matters a lot. It doesn\u2019t have to be Silicon Valley, although that\u2019s the most obvious. Risk for me, put simply, would be the probability of an irreversible negative outcome. There are some cases where that\u2019s part of the calculus, but typically, I thought about making a journal. I seriously contemplated doing this because everyone\u2019s making a journal now, but I went to the bookstore, I was like, \u201cThere are too many journals, I\u2019m not going to do it.\u201d<\/p>\n<p>But the journal was going to be called \u201cworries that mostly didn\u2019t happen.\u201d It\u2019s just like you just write down what you\u2019re worried about and then you look back three months later, and again, none of that actually mattered. The cost of \u201cfailure\u201d is very low for most things. You can also get a signal, positive or negative, go or no-go, pretty quickly if you\u2019re methodical about it. I try to view, reframe failure, as scientific feedback. You have a hypothesis, you test it, it didn\u2019t pan out, still valuable. If you\u2019re optimizing for learning and relationships that transcend any given project, experiment, company, job, et cetera, those things snowball over time.<\/p>\n<p>If you\u2019re keen on doing short-term experiments but long-term greedy, it\u2019s very hard to lose, in my opinion. From what I\u2019ve seen, and this is based on Silicon Valley, so it\u2019s maybe anomalous, but it\u2019s really hard to fail over the long term.<\/p>\n<p>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\u2019s pick on consultants because, why not? There\u2019s no real risk of failure. You\u2019re going to get 95 things out of a hundred right on that path. On the Founder path, you are getting most things wrong. You\u2019re asking people for money, they\u2019re saying no. You\u2019re asking customers to transact with you, they\u2019re saying no. You\u2019re trying to hire people, they\u2019re saying no. You\u2019ve got no resources. You\u2019re constantly surrounded by a life of failure.<\/p>\n<p>You\u2019ve just got to decide which life sounds better. What you suddenly realize is, wow, well, a life without failure, it\u2019s 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\u2019s no return. Risk is a good thing. It is not what you immediately think of, which is, \u201cOh, I want to stay away from it.\u201d You need risk. Okay? What that doesn\u2019t mean is that you\u2019re jumping off a cliff. What it means is you understand how to operate in terms of risk.<\/p>\n<p>You need to incorporate some of the frameworks that you\u2019ve talked about in class today to measure and calibrate it. But Tim\u2019s not writing these books if he\u2019s not willing to encounter risk.<\/p>\n<p>TIM FERRISS: Yeah, the <em>4-Hour Body<\/em>, still recovering from some injuries from that one, 2010. Just had a surgery on this elbow as a result of that book.<\/p>\n<p>REZA SATCHU: Everyone must have thought that was a crazy idea.<\/p>\n<p>TIM FERRISS: It was crazy. But to use the <em>4-Hour Body<\/em> as an example, the 4-Hour Work Week bought me permission to experiment outside of that lane, and so I did the <em>4-Hour Body<\/em> 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\u2019t 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\u2019re very good at thinking about all the possible downsides of doing the new thing or doing the \u201crisky thing\u201d.<\/p>\n<p>But they don\u2019t 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\u2019s like, \u201cAll right, I might as well do the weird thing first.\u201d<\/p>\n<p>BRIAN KENNY: Did you ever worry about your brand though, the Tim Ferriss brand? If I do something that\u2019s too contrarian, I may lose some of my brand cachet.<\/p>\n<p>TIM FERRISS: I don\u2019t think about brand really at all, which isn\u2019t 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\u2019t 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\u2019ve seen that happen to people, and you can\u2019t hit control Z on that very easily, so I don\u2019t 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\u2019re generally within the context of a six to 12-month project. When I\u2019m 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\u2019s 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\u2019s like, if you were to go to a boxing class and you\u2019ve never done boxing before and you get hit in the liver with a punch, it\u2019s not even a hard punch. It\u2019s going to be really shocking and unpleasant. If you do it for six months, you\u2019ll be like, \u201cOkay, yeah, I\u2019m going to get 50 of these today. It\u2019s fine.\u201d 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.<\/p>\n<p>REZA SATCHU: Brian, this is what\u2019s so valuable to Founders, is exactly this, which is what they\u2019re getting is hit all the time, but they\u2019re learning that they can recover much faster through those hits.<\/p>\n<p>TIM FERRISS: Yeah. Could I add one more thing?<\/p>\n<p>REZA SATCHU: Yeah, of course.<\/p>\n<p>TIM FERRISS: I\u2019ll 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\u2019s laughably ridiculous. I was so stressed out, I couldn\u2019t 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\u2019m dealing with all this and it\u2019s tearing me up inside. Then, I was having a conversation with this friend of mine who\u2019s been on multiple public boards. He\u2019s in private equity for a super long time, very, very good investor. He\u2019s like, \u201cWhat?\u201d He\u2019s like, \u201cThis is the first time you\u2019ve been sued.\u201d He\u2019s like, \u201cI should sue you.\u201d He\u2019s like, \u201cWelcome to the club.\u201d He\u2019s like, \u201cWhat are you so upset about?\u201d I was like, \u201cWhat are you talking about?\u201d I tried to justify it, and he\u2019s like, \u201cAh. It\u2019s fine.\u201d I was like, \u201cOh, okay.\u201d 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.<\/p>\n<p>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?<\/p>\n<p>TIM FERRISS: I think it depends a lot on who you\u2019re talking to, right? It\u2019s like, if we\u2019re talking to a bunch of refugees who had made hard choices. Then, I would say they probably accurately estimate their adaptiveness.<\/p>\n<p>REZA SATCHU: Ability. Yeah.<\/p>\n<p>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\u2019s more or less complete information, like higher education. It\u2019s like, \u201cOkay, great, you\u2019re on the dean\u2019s list, you\u2019re summa cum laude, or whatever.\u201d That those people underestimate their resilience, but I don\u2019t actually think they\u2019re 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\u2019s like, \u201cNo, okay, you want to change the world and build a billion-dollar company doing X?\u201d It\u2019s like, \u201cAll right, go talk to 10, go pitch 10 customers next week and ask them for money.<\/p>\n<p>As a dry run to get prepayment that will fund X, Y, or Z.\u201d But don\u2019t hide, and then I\u2019m quoting Seth Godin, \u201cBut don\u2019t hide behind the big.\u201d Get out there and it\u2019s going to be messy.<\/p>\n<p>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\u2019m wondering, once you\u2019ve 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\u2019s worth pursuing, what you shouldn\u2019t pursue? What\u2019s the thought process there?<\/p>\n<p>REZA SATCHU: Yeah, so it\u2019s interesting. In my life, as someone who\u2019s founded a few businesses, in some ways, the most recent businesses are harder, surprisingly. One would say, \u201cWell, it\u2019s easier because you\u2019ve got more resources, more expertise, you have less hunger, and you have much more options. It\u2019s not as critical that it has to succeed.\u201d I teach and I found a business at the same time. That\u2019s crazy. Most people would say that is not an optimal way to found a business. Whereas, my first couple of businesses, there\u2019s no way I\u2019d be teaching and founding a business. I\u2019d be fully focused on founding.<\/p>\n<p>I think this idea that it gets easier, it might get easier from an expertise perspective, but suddenly you\u2019ve got what I call the curse of optionality, which is you\u2019ve got a number, and Tim, you\u2019re facing some of this right now, frankly, this paradox of choice, which is precisely because of the success you\u2019ve had you\u2019ve got a whole bunch of choices. He mentioned Seth Godin, who\u2019s 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.<\/p>\n<p>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\u2019re capable of when you commit. I\u2019ve not had money and I\u2019ve 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, \u201cWell, maybe I can preserve those options for a very long time.\u201d I\u2019m curious, Tim, I would ask you this question, which is you\u2019ve got a whole bunch of options ahead of you. Here\u2019s what I know to be true, is if you committed to one, I\u2019m sure it will be far more impactful than if you preserve all of them.<\/p>\n<p>TIM FERRISS: Yeah, that\u2019s 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\u2019m saying, \u201cAll right, you know what\u2019s going to really get attention, is if you\u2019re an HBS grad who offers to shadow a show runner or a producer in pre-production on a movie, and you\u2019re like, \u201cNothing is beneath me. Cleaning toilets, getting your coffee, I don\u2019t care.&#8217;\u201d<\/p>\n<p>It\u2019s like, \u201cAll I want to do is observe some deal making and see what goes into making a film.\u201d It\u2019s like, \u201cYou 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.\u201d That\u2019s number one.<\/p>\n<p>REZA SATCHU: But are you also suggesting that because that\u2019s a differentiator, meaning, there\u2019s something that it says about you, that you\u2019re willing to do that?<\/p>\n<p>TIM FERRISS: Here\u2019s my experience. Even though you might feel there\u2019s very little time and a big rush, there\u2019s not a big rush. You can take time to have these little detours and try things. The second is that even though I\u2019m doing some different things, let\u2019s just say angel investing newsletter foundation focused on mental health therapeutics, nonprofit, blah, blah, blah, blah, blah. There\u2019s actually a way in which they reinforce one another. I will use, say, the podcast to interview scientists based on science I\u2019m interested in to determine if I think they\u2019re a good candidate for the foundation, or potentially, it doesn\u2019t 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\u2026 Preserving all of your options also is just an illusion. You can\u2019t really do that. The nature of making a decision, it\u2019s 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\u2019ve 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\u2019t have to be commit forever. It shouldn\u2019t probably be commit forever, unless you\u2019re the person who knows at age five that you want to do X. If you\u2019re that, I don\u2019t know, maybe you wouldn\u2019t be here.<\/p>\n<p>REZA SATCHU: Positive constraints means cutting off options, in some sense?<\/p>\n<p>TIM FERRISS: It means cutting off options, or it could be anything. If you\u2019re writing, it could be a space or page constraint. It could be, I have to write this all in third person or first person.<\/p>\n<p>REZA SATCHU: Well, it\u2019s also your comment around, if I\u2019ve got a problem, I will only solve it by taking something away.<\/p>\n<p>TIM FERRISS: Right, so in the case of the podcast, I found myself starting to drag my feet because it\u2019s 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, \u201cGive me 10 questions in the style of Tim Ferriss or Lex Friedman or Joe Rogan interviewing this person.\u201d Boom, you\u2019ll 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\u2019m generally not looking for the cutting edge. I\u2019m looking for dull edge.<\/p>\n<p>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\u2019s 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\u2026 I know this is, again, it\u2019s 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\u2019t want to sell San Francisco. It\u2019s 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.<\/p>\n<p>BRIAN KENNY: We haven\u2019t talked about impact, but I know that\u2019s an important part of the thing that you cover in Founder\u2019s 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?<\/p>\n<p>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\u2019ve learned a lot, when I\u2019ve had the benefit of resources, all these sorts of things. The problem is there\u2019s two problems. One is you may or may not be around for that last piece.<\/p>\n<p>BRIAN KENNY: Never know.<\/p>\n<p>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\u2019re\u2026 We all have these, especially here, have these visions of grandeur around having massive impact. Well, I\u2019d 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\u2019d be curious how you define learning.<\/p>\n<p>Okay, so I\u2019m going to propose what my definition of learning is, and you tell me whether this, because I think it\u2019s an important concept because learning is\u2026 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\u2019re making\u2026 it\u2019s all about decision making. Meaning, the trait we are most trying to learn is judgment. Judgment occurs when you\u2019re making consequential decisions that you\u2019re accountable for.<\/p>\n<p>You must live a life where you\u2019re 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\u2019m curious to know your thoughts about that.<\/p>\n<p>TIM FERRISS: Learning, there\u2019s how to learn, and then there\u2019s what to learn. If you\u2019re 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\u2019s like, okay, if you\u2019re in the waste management business and you\u2019re understanding the ins and outs of waste management, I\u2019m 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.<\/p>\n<p>REZA SATCHU: Yeah, Wayne Huizenga. They don\u2019t know who Wayne Huizenga is.<\/p>\n<p>TIM FERRISS: I know.<\/p>\n<p>REZA SATCHU: You and I know who Wayne Huizenga is.<\/p>\n<p>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\u2019re able to watch someone acquiring dozens and dozens of companies, and how that entire dance is woven, that transfers. If you\u2019re learning how to communicate, let\u2019s just say, I\u2019m 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\u2019re involved with all of those PR stunts, which fundamentally are thinking about positioning and differentiation, that will apply to everything. It\u2019s just asking yourself, where could this transfer? Where could this apply? Then, that\u2019s the stuff that you focus on. For me, it\u2019s in a sense meta skills, that if you were to copy and paste, you take somebody, look, it doesn\u2019t matter.<\/p>\n<p>Well, I\u2019ll give you actually maybe a more contemporary example, like Jeff Bezos. All right. What is Jeff Bezos\u2019 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.<\/p>\n<p>REZA SATCHU: From day one, yeah.<\/p>\n<p>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\u2019s 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\u2019re like, \u201cOkay, I got it.\u201d But it\u2019s 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.<\/p>\n<p>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\u2019s like, \u201cNo, you can do my job.\u201d Then, he\u2019s like, \u201cAll right, give me a situation.\u201d They gave him a situation. He\u2019s like, \u201cAll right, does that help us to be the low cost airline or not?\u201d They\u2019re like, \u201cNo.\u201d He\u2019s like, \u201cYeah, that\u2019s a no.\u201d He\u2019s like, \u201cOkay, next one.\u201d He\u2019s like, \u201cYeah.\u201d 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\u2019m thinking about adopting another dog.<\/p>\n<p>But there\u2019s an expression in dog training, which is basically if the dog hasn\u2019t done it, say a behavior, shaping a behavior in 20 different locations, 20 different durations, they don\u2019t have that behavior. It\u2019s not durable. Humans are the same. It\u2019s 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\u2019s an incredible shortcut. But you and I have different perspectives on this. I think working for a startup\u2019s a fantastic way to learn on someone else\u2019s dime with the understanding that-<\/p>\n<p>BRIAN KENNY: That\u2019s our youngest audience member, by the way.<\/p>\n<p>TIM FERRISS: Yeah. Start them young. Start them young.<\/p>\n<p>REZA SATCHU: It\u2019s true. What I\u2019d 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.<\/p>\n<p>I have a phrase which is, if in doubt, act, which immediately people say, \u201cWell, wait, Reza, you don\u2019t know what you\u2019re doing, you\u2019re going to act?\u201d No, the reason I say that is because so many people are paralyzed by imperfect or uncertain information, and so they\u2019re like deer in headlights. What I suggest is, even if you\u2019re going to stay the course, train yourself to make a decision that you\u2019re actually staying the course, which is a bias for action. I\u2019m curious how you think about, bias for action is, it feels risky. I\u2019m curious how you view that.<\/p>\n<p>TIM FERRISS: What I would say is I have a tendency\u2026 My mom literally got me a shirt that says, \u201dWait a second, let me overthink this.\u201d My tendency is to, I don\u2019t want to say perseverate, but over consider the ramifications of a lot of decisions. It\u2019s 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\u2019s literally a guideline that he uses with his chief of staff.<\/p>\n<p>He says 10% footfall, which is a little confusing because it\u2019s a tennis reference. Anyway, but I think applying that to your own life where you\u2019re 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\u2019s with diet, exercise. You don\u2019t want to get up in the morning and decide which of 20 toothpaste tubes you\u2019re 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.<\/p>\n<p>I literally met with, I was having a blood draw this morning because I\u2019m in Boston for proteomics assay. Anyway, it\u2019s a long story. But they have a dedicated discord within the company for celebrating bleep-ups basically. That are not egregious. It\u2019s 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\u2019m not sure how I feel about that.<\/p>\n<p>But in any case, I don\u2019t know about also\u2026 I got stuck on the AI stuff again, because I don\u2019t know, I wish I could give everybody and myself a strategy for making yourself AI proof. I don\u2019t know what that looks like.<\/p>\n<p>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\u2019re going to have multi-billion dollar companies or billion-dollar companies with one to three employees, I\u2019m very confident in that. They\u2019ll just use agents to fill a lot of roles, like CFO and so on. People are already doing this. I wouldn\u2019t get too hung up on that.<\/p>\n<p>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.<\/p>\n<p>REZA SATCHU: Human thing.<\/p>\n<p>TIM FERRISS: It\u2019s very rare that you\u2019re just going to be able to send pitch emails with the deal structure and you\u2019re like, \u201cYes or no, thumbs up?\u201d With this emoticon based on my AI chatbot, like, \u201cGreat. Let\u2019s do a deal.\u201d Typically, not how it works, especially as the stakes get bigger, which don\u2019t mean they\u2019re huge, that they\u2019re just consequential for whoever you\u2019re dealing with. That stuff I don\u2019t see going away anytime soon.<\/p>\n<p>BRIAN KENNY: I want to give time. We\u2019re coming close to the end of our time. I\u2019ve 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.<\/p>\n<p>TIM FERRISS: Yeah, if people want, so this is a very off menu thing.<\/p>\n<p>BRIAN KENNY: It\u2019s just like the Oprah Show. You\u2019re going to get something to take with you.<\/p>\n<p>TIM FERRISS: Yeah, exactly. It\u2019s not a car, but it\u2019s something else. I ended up collaborating with this guy, Elan Lee, who\u2019s one of the world\u2019s best game designers for the last two years to create a card game for off-screen social interaction. That\u2019s 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, \u201cI would pay to just hang out with this guy.\u201d<\/p>\n<p>He\u2019s such a soulful, deep thinker, who\u2019s ethical and also happens to be a polymath, top 1% in multiple fields. I was like, \u201cI just want to steep myself in whatever magic juju this guy has.\u201d That\u2019s how fundamentally I made the decision. Yeah, there are games up there, it\u2019s called COYOTE. Then, beyond that, I do have an 800-page draft of a book. That\u2019s not an overstatement. I\u2019ll be whittling that down over the next six months probably. That\u2019s been like eight years in the making. It\u2019s been sitting back there for a long time. There\u2019s other stuff going on.<\/p>\n<p>BRIAN KENNY: That\u2019s 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\u2019ll ask the same question of each of you, and I\u2019ll start with you, Tim, and I always give the professor the last word because it\u2019s Harvard Business School, but it\u2019s a pretty simple question.<\/p>\n<p>TIM FERRISS: Reza is pretty good at getting the last word anyway.<\/p>\n<p>BRIAN KENNY: I think that\u2019s true.<\/p>\n<p>REZA SATCHU: That\u2019s true. That is definitely<\/p>\n<p>BRIAN KENNY: If you just think about the case, you\u2019ve lived it, what lessons do you think emerging founders should take from the case about navigating similar inflection points in their own journey?<\/p>\n<p>TIM FERRISS: Let\u2019s see. I\u2019m 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\u2019m aware of, \u201cHigh-tech Entrepreneurship,\u201d 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\u2019re like, \u201cCan anybody else teach this class? He was like, \u201cOh, I\u2019ll figure it out.\u201d Back in the day. In his last class, I think I\u2019m getting the name of this song right, but he actually gets up and he sings this song. I\u2019m going to do it my way. The whole point is everybody\u2019s 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\u2019t have been prouder and happier with how everybody put it together, Denise and Reza and so on, is that you don\u2019t have to follow the prescription, whatever the prescription is. You don\u2019t have to meet the expectations, whatever the expectations are. You just don\u2019t have to do it. There are a lot of ways to improvise and zig and zag. As long as you\u2019re 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\u2019s 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\u2019ve done these 800 plus interviews on the podcast, and they\u2019re like, \u201cWhat are the commonalities?\u201d I\u2019m like, \u201cThe greatest commonality is there are no commonalities.\u201d<\/p>\n<p>It\u2019s like for every incredible writer who gives me one set of advice, I sit in front of the screen, even if it\u2019s 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, \u201cYeah, I really need to get into the mood.\u201d It\u2019s like, \u201cI\u2019ll have my cappuccino, I\u2019ll read the paper, I\u2019ll do this thing. I really need to be in the right state to write.\u201d They\u2019re 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.<\/p>\n<p>REZA SATCHU: Look, I think that\u2019s extremely well said. Tim, when we wrote this case study, in some ways it\u2019s probably the longest case study because he\u2019s got so many things going on. My students are probably like, \u201cThis is a 20-plus page story.\u201d It\u2019s everything from dancing, to an author, to podcasts, to all sorts of things. If I had to summarize it, I\u2019d want two takeaways. One is, live a life full of curiosity and allow yourself to explore the things that you\u2019re curious with. Whether that\u2019s these experiments, small C commitments, just suspend disbelief and trust your judgment to actually explore things that you\u2019re curious in. The upside is far greater than the downside. That\u2019s the first point.<\/p>\n<p>The second point is, I really think Tim\u2019s risk framework is very interesting. In some ways you hear a story and you immediately think, \u201cWell, this guy is embracing risk at every turn.\u201d It\u2019s actually the opposite. He understands that he has to live a life with risk, but he\u2019s 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\u2019s defining his fears, which allows him to hopefully do something extraordinary because he\u2019s shifting what the outcome could be.<\/p>\n<p>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.<\/p>\n<p>TIM FERRISS: I\u2019d 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\u2019s a two-part blog post series called How, I think it\u2019s just \u201cHow I Created a Real World MBA.\u201d Related to how I tiptoed my way into angel investing.<\/p>\n<p>REZA SATCHU: Well, this is your angel investing.<\/p>\n<p>TIM FERRISS: I think that\u2019s 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\u2019s one called <em>The Art of Possibility<\/em>, I think the author\u2019s last name, it\u2019s by a husband and wife duo, Zander, Z-A-N-D-E-R. It\u2019s very fast read, amazing book. There are a lot of book recommendations I could give, but that\u2019s a fast one that I would encourage people to check out.<\/p>\n<p>Really study the outliers, like Yvon Chouinard, the early chapters, the early chapters, or if you think of someone who\u2019s a risk-taker, like Richard Branson, read <em>Losing My Virginity<\/em>. It\u2019s like at every turn that guy is hedging risk and minimizing and mitigating risk. It\u2019s 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.<\/p>\n<p>BRIAN KENNY: I think that\u2019s a good note to end on. Tim, Reza, all of you, thank you for joining me on Cold Call.<\/p>\n<p>REZA SATCHU: Thanks, Brian.<\/p>\n<p>TIM FERRISS: Thanks.<\/p>\n<p>BRIAN KENNY: If you enjoy <em>Cold Call<\/em>, you might like our other podcasts: <a href=\"https:\/\/www.hbs.edu\/environment\/podcast\/Pages\/default.aspx\"><em>Climate Rising<\/em><\/a>, <a href=\"https:\/\/hbr.org\/podcasts\/coaching-real-leaders\"><em>Coaching Real Leaders<\/em><\/a>, <a href=\"https:\/\/hbr.org\/podcasts\/ideacast\"><em>\u30a2\u30a4\u30c7\u30a2\u30ad\u30e3\u30b9\u30c8<\/em><\/a>, <a href=\"https:\/\/www.hbs.edu\/managing-the-future-of-work\/podcast\/Pages\/default.aspx\"><em>Managing the Future of Work<\/em><\/a>, <a href=\"https:\/\/www.alumni.hbs.edu\/events\/Pages\/skydeck.aspx\"><em>Skydeck<\/em><\/a>\u305d\u3057\u3066 <a href=\"https:\/\/www.hbs.edu\/news\/podcasts\/think-big-buy-small\/podcast-details?episode=3618853027\"><em>Think Big, Buy Small<\/em>.<\/a> Find them wherever you get your podcasts.<\/p>\n<p>If you have any suggestions or just want to say hello, we want to hear from you. Email us at <a href=\"https:\/\/hbr.org\/podcast\/2025\/10\/mailto:coldcall@hbs.edu\">coldcall@hbs.edu<\/a>. Thanks again for joining us. I\u2019m your host Brian Kenny, and you\u2019ve been listening to <em>Cold Call<\/em>, an official podcast of Harvard Business School and part of the HBR Podcast Network.<\/p>\n<\/p><\/div>\n<p>#Shape #Chapter<\/p>","protected":false},"excerpt":{"rendered":"<p>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\u2019s next? 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