Tim Ferriss: If Only I Knew

If Only I Knew is an email series where we talk to the world’s greatest entrepreneurs, artists, entertainers, and leaders and ask them about the things they wish they knew when they were younger.

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This week’s interview is with Tim Ferriss, an early-stage technology investor and the author of four #1 New York Times bestsellers, including The 4-Hour Workweek, and host of The Tim Ferriss Show podcast,


The Hustle: Tell me a story about a time when you thought to yourself, “I’m completely fucked!”

Tim Ferriss: I would say the first thing to recognize is that, in every case, I wasn’t totally fucked, because I’m still here. I’m gonna get into examples — but the overarching lesson that I would want to impart is that, to quote Seneca, “a man who suffers before it is necessary, suffers more than is necessary.” So, spend less of your energy worrying about all the worst-case scenarios and contend with them if they happen…

The story that comes to mind is more of a lifestyle correction really. I recall one Thanksgiving being in my office at the startup I worked for at the time, my first job out of college. Nobody else was in the office (understandably), and I was sending off ‘Happy Thanksgiving’ emails to prospective clients for data storage systems. At that point in my life, I had been sleeping under my desk and really using overwork ethic as a badge of honor — something to be prideful about.

That led to overconsumption of caffeine and other stimulants, and eventually, not shortly thereafter, it led to all sorts of health issues. So, I would say that required me to take time off of work, because I got sick and so on. But I think that really I had the inkling at that point, and the realization that what I was doing was completely unsustainable. And I think that was one of the dominoes that sort of toppled the rest of these dominoes that led to me, a year later, starting my own company to essentially correct that problem.

I realized that whether you’re in a company or starting your own company, your behaviors travel with you. So that didn’t solve the problem by itself. I actually ended up working more hours and being more aggressively driven. And then, in 2004, taking 18 months around the world ultimately to try to discover a better way of doing things, which led to The 4-Hour Workweek.

So, a lot of those fuck ups early on, even though they’re painful and seem like the end of the world, with relationships ending and girlfriends leaving and so on, were the experiences that ended up being the necessary ingredients for the Four-Hour Workweek coming together.

The Hustle: What’s one routine that you wish you started when you were 25?

Tim Ferriss: Morning meditation, probably. Twenty minutes of meditating in the morning. That could be transcendental meditation, it could be guided meditation. Some type of consistent meditative practice so that I would have more self awareness of my emotional and physical state, which I think would’ve led me to consume less caffeine, less alcohol, and, in general, to be less emotionally reactive. That’s the cornerstone habit I think I would choose.

The Hustle: Are there any professional opportunities that you passed that you wish you could go back in time and address?

Tim Ferriss: I was a pre-IPO investor in Facebook and sold at a particularly low moment, and I think I made that decision emotionally because I did not have an unemotional plan beforehand for how much I would sell or not sell at different points, with triggering events. I hadn’t decided beforehand how to delegate that responsibility so that I wouldn’t make an emotional decision that was irrational and probably self-defeating.  And they are certainly start-ups that I’ve missed in terms of huge opportunities that would’ve returned 100x or more in several cases.

But ultimately I feel like I’m pretty good, or better than most, at not losing money. So, my rules have served me well — even if I’ve missed opportunities that, in hindsight, would’ve been very attractive.

The Hustle: What are some things that you wish you would’ve done to your body earlier?

Tim Ferriss: I would say focusing on shoulder mobility. Specifically, shoulder extension and thoracic spine mobility.

The Hustle: What are your criteria for pursuing one project versus the other? And are they the same as when you were much younger?

Tim Ferriss: My criteria when I was younger were different, but I think my criteria now are better, and perhaps I would’ve made faster progress had I used my current criteria then.

I really subscribe to the Scott Adams approach, which he called “systems thinking.” My simplified and slightly adapted version consists of two criteria. Number one: I’m choosing projects based on the relationships and skills they will help me to develop, so that even if that project fails, I am succeeding in developing relationships and skills that can transcend that project and apply to other things. Second: I have to feel a very visceral excitement about the project.

So, if I check those boxes — Develop skills even if the project fails, develop relationships even if the project fails, and make sure I’m very excited about it and it’s something that I want to talk about or something that keeps me up at night with ideas flowing — it’s very difficult to fail.

The Hustle: You’ve accomplished a lot that I imagine the younger version of Tim wouldn’t think was possible. Is there a certain framework that you’ve used to break down some of these seemingly overwhelming obstacles?

Tim Ferriss: Not really. I would say that most of the huge successes I’ve had have been unintended and were not the direct result of any kind of five- or ten-year plan, or a sophisticated framework, aside from the systems thinking that I described with the developing of relationships and skills. Very frequently, the biggest successes have been side effects of something else. Which is why — at least for me — it’s been very important not to have a calcified ten-year plan that causes me to put blinders on.

For instance, I was an advisor to StumbleUpon way back in the day, Garrett Camp (StumbleUpon’s founder) was involved, and I became friends with him. Financially, StumbleUpon did not have any ROI for me, but I was able to learn a lot about content discovery and develop a relationship and friendship with Garrett, which later resulted in me becoming a pre-seed advisor to Uber. That has, at this point in time, become a hugely high percentage of my net worth, on paper at least. And that wouldn’t have happened had I tried to look at StumbleUpon as a fast transactional project. I wouldn’t have stuck with it, and it would’ve cost me more money than I have made in my life in total otherwise (at least looking at my portfolio currently).

Hopefully, people find it reassuring that I don’t have a master plan. I’ve never had a master plan; I’ve just followed my three checkbox criteria for selecting projects, with faith that as those accumulate I will have opportunities and be able to see opportunities that will be a perfect fit, which has been the case.


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