Four Takeaways from Tim Ferriss on KindredCast
Tim Ferriss is no stranger to podcasting. Aside from being an early-stage investor and advisor in companies like Uber, Facebook, Duolingo, Alibaba, and more, he is also the host of The Tim Ferriss Show podcast, which is the first business podcast to exceed 100 million downloads. He gained worldwide recognition for his book The 4-Hour Workweek, and has since authored five #1 New York Times and Wall Street Journal bestsellers. Most recently, we had the pleasure of hosting him on KindredCast, where he shared his insights on the advantages of a shorter work week, his investments, and the promise of psychotropic treatments for mental health.
Here are the four biggest takeaways from his conversation with LionTree’s Alex Michael:
- Not Everyone Should Work From Home
The pandemic has spurred a remote-work revolution. While many would argue that working from home provides advantages like greater flexibility and work-life balance, the realities of remote work pose incredible challenges for a number of people:
Tim Ferriss: Not everyone is built to work from home. There are psychological challenges, and there can be depression and other issues that if you don’t have systems and coping strategies in advance, which I also talked about quite a bit in The 4-Hour Work Week, although people glossed over it, you can get yourself into trouble psychologically, psycho-emotionally. And for a lot of people, certainly, it’s if you have kids and your kids are at home, how well can you coexist running a business or doing your job with your kids at home? Do you have boundaries? Do you have rules?
2. When Investing, He’s Much More Focused on What Could Go Wrong Than What Could Go Right
With such an impressive portfolio, you might think that Tim Ferriss has a crystal ball when picking the companies he wants to invest in. No magic here, just a shrewd eye for potential conflict:
Tim Ferriss: If I ask them [CEOs], for instance, as I typically do, I’m like, “Okay, let’s say this company has failed. Three years from now, it’s failed. What are the top three or four reasons or contributing factors that would lead to it failing?” If they can’t answer that-
Alex Michael: There’s that trust factor again, you’re going negative. That’s so interesting how you think because you’re not thinking about the success of it, you’re thinking of things that go wrong, which is how you seem to be programmed. You’re in the minority of the populace.
Tim Ferriss: I think it’s how I’m programmed, and in part, because I’ve seen many companies, I don’t want to name names, but many companies that had the tiger by the tail, they’re experiencing explosive growth, and then they just become a supernova of capital instruction, because they start to believe they’re invulnerable or they start to believe that… They end up being surrounded by people who laugh at all their jokes and tell them how smart they are, and they don’t have anyone to try to pick apart their arguments, and more importantly, they don’t have people around them who cultivate the ability in them and support the ability for them to pick apart their own arguments. Not to beat a dead horse here, but I think Toby of Shopify is one of the best in the world at this.
Alex Michael: He’s done pretty well.
Tim Ferriss: He’s incredibly, incredibly disciplined.
Alex Michael: So you want to see these people be prepared for adversity, basically, and sense that in them, but also have that thought out enough such that…
Tim Ferriss: Not just be prepared for adversity, but … I’m going to pull out a Desmond Tutu quote, I’m going to butcher it, but he says that “We can pull people out of the river and pull people out of the river. At some point, we should go upstream and figure out why people are falling in the river.” So I think that… I had an employee at one point, and I said to another employee…Actually, to someone who’s advising me, and I said, “She’s really, really good at putting out fires,” and the answer was, “Well, maybe she should be better at preventing fires.” I think that good CEOs, to be able to navigate preemptively around these potentially fatal mistakes or crippling mistakes, need to be able to hypothesize what these worst-case scenarios could look like, and the best CEOs I’ve met are really able to do that.
3. He is Not a People Pleaser
With millions of followers across the globe, Tim Ferriss can’t possibly please everyone. So why even try? In fact, he credits much of his success to his ability to make content for only a small fraction of his audience:
Tim Ferriss: I don’t try to make podcasts that appeal to my whole audience. Each episode, my goal, actually, I should say, is that 10% of my audience will love the episode and that, through a rotation like once a month or once every two months, every listener of the podcast will find one episode they share with like 20 people.
4. He Can Never Be Cancelled
Cancel culture is pervasive in all aspects of online life — but how can we have hard conversations when there is a looming feeling of judgment? Take it from Tim Ferriss, who is unapologetically, authentically himself in every episode:
Tim Ferriss: As I’ve become older and have felt more and more secure in myself, in my financial position in the world and so on, I care less about any type of acting. And I think that is a superpower. I think I’ve become much more authentic, and not that I was pretending before, but I was always guarded on some level before and there was more fear factor, another reason that I preserved my open RSS, I can’t be canceled. Nobody can cancel me and that gives me tremendous freedom. So I think I have become better at being very, very, very authentic with my audience about very hard, very uncomfortable things. And I do think that your success in life can be measured in the number of uncomfortable conversations you’re willing to have.
To see the full conversation, you can watch here on YouTube or listen wherever podcasts are found.
