Tim Ferriss: Tech has too much ‘dumb capital’

August 22, 2013, 2:06 PM UTC

FORTUNE — If anyone gets the entrepreneur’s plight, it’s Tim Ferriss. The East Hampton, N.Y.-raised, Princeton-educated author once worked in sales at a data storage company before starting a sports nutrition supplement company and penning The 4-Hour Workweek in 2007. The controversial New York Times bestseller inculcated readers to Ferriss’s “lifestyle design” principle, serving up ways to optimize the work day and increase quality of life. Its success established him as a self-help guru and paved the way for a follow-up in 2010. Last fall, he created a stir as the first major author to sign with Amazon (AMZN) Publishing to distribute The 4-Hour Chef. At the same time, Ferriss also kept his eye on the tech scene. To date, he has invested in and advises over 30 tech companies, from Facebook (FB) and Twitter to Uber and TaskRabbit.

Fortune caught up with Ferris at the launch of the digital lifestyle brand InsideHook in San Francisco, where the former national Chinese kickboxing champion (yes, really) reflected upon his Amazon flirtation, why he’s on hiatus from investing, and why another book isn’t coming any time soon.

Fortune: You told me earlier that 250 pages were cut from the 4-Hour Chef. Feel free to disagree, but I’d heard you weren’t happy with Amazon. Is that true?

Ferriss: There were many things I was more than happy with, but I think everyone underestimated the irrational backlash from big box retailers that would come of Amazon Publishing. That wasn’t the fault of Amazon, and I don’t blame Amazon for that. We understood the risks going in. So as the opportunity presented itself, I made the decision to pull the trigger. I take responsibility for that. On the digital side, Amazon executed fantastically. We anticipated that Barnes & Noble (BKS) would boycott. We did
anticipate that Target (TGT), Costco (COST), Wal-Mart (WMT), and so on would boycott.

The landscape is changing so quickly, but the experiment itself taught me a lot. It was like [getting an] MBA in the next wave of publishing. With the next book, would I do Amazon? Would I do traditional? Would I do a mixture? Would I do self-publishing? I don’t know.

Part of the reason I’m not doing a new book in the immediate, foreseeable future is that I think there’s going to be a bloodbath or arms race over say, the next 24 months, and I want to wait until the dust settles. I wouldn’t underestimate Amazon! [chuckles] And as a traditional publisher, I would also say, I wouldn’t get myopically focused on Amazon when there are at least a dozen startups you should also be concerned with. If you’re not going to innovate, I would do so while they’re less expensive —

— and not Amazon. 


In other words, don’t expect another Tim Ferriss book within the next one to two years.

I don’t think so. I mean, never say never, but I would be exceptionally surprised if I were to have a book come out in the next year or two.

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So if you’re not writing another book, what are you working on?

I can’t give you a lot of detail, but I’m going to be executive producing and hosting my own TV show on primetime.

When can we expect that?

It’s coming very, very soon. There will be news probably within the next two months.

Books aside, you’ve also been a startup investor and advisor. What do you look for in a startup, and what’s on the radar these days?

So I look for consumer-facing products addressing a problem I have that are already demonstrating traction of some type — like user adoption — that I can help dramatically. They need to be simple enough to understand, yet unique enough to pitch a trend piece to say,
or the 
New York Times
. Which means by default, I could pitch it not just to New York and San Francisco but the rest of the country. And ideally, but not a prerequisite, a product-focused studio and at least one person who’s been with the startup from early inception to exit on the exec team.

So it’s largely driven by the talent more so than the product?

And a product I can use in its current state and derive value from. Evernote solved all my researching and paperless goals for creating books. TaskRabbit allows me to get rid of all the errands and busywork. Uber solves major problems in San Francisco that are parking-related, taxi-related, and so on. That’s pretty much it.

I’ve been criticized by some VCs who’ve said it’s naive to only invest in companies whose services and products you would use yourself, but so far it’s been a good rule for me not losing money!

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Is there a startup you’d call the “the one that got away,” one you wished you’d backed?

Square is definitely one of them. There are many, but that’s the first one that comes to mind. Operationally and from a product standpoint, I just have so much respect for what they’ve done and what they continue to do, and think they’re just getting started.

I love the ones that look obvious in hindsight. People now look at Uber and go, “Oh, my god. Of course. So straightforward. How could it not do well?” The fact of the matter is, it didn’t look obvious at all to people in the very beginning. (And I was a pre-seed advisor to Uber.) It wasn’t obvious except for people looking into a crystal ball, trying to look 10 years down the field like [cofounders] Garrett Camp and Travis Kalanick.

Is there an area of tech you’re currently eyeing?

I hate to say it, but no. I’m actually considering dialing back my startup involvement.

Why is that?

I think there’s way too much “dumb capital” floating around. You have people signing deals offering unbelievably insane terms to early stage companies that haven’t validated their product at all. That’s great for the entrepreneurs because even if 99 stupid ideas are funded, there should be one out of 100 that could change the world. For someone capital-constrained, it makes investing intelligently very difficult.

When I invested in Uber or TaskRabbit, they were sort of ahead of the curve before these labels or themes were even available. I feel like by the time there’s a theme that’s easily understood, you’re already behind the wave and you’re investing in funds, so I really don’t know. I just look for things where I go, “Holy shit! How do I live without this?”

You mention “dumb money.” I’ve been hearing that sentiment from some other investors as well. 

The “dumb money” tends to represent fair-weather investors, so if the macroeconomic takes a huge downturn, that’s going to be the first money to flee.

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Much of what people know you for is this philosophy around optimizing parts of one’s life, whether it’s the body or the workweek. How do you reconcile that with the startup life and a lot of entrepreneurs who may work really long hours?

Well, I think there are very different tracks you can choose as an entrepreneur. There’s a broad spectrum, meaning the term “entrepreneur,” let’s just for the sake of simplicity say someone who creates a company, fully-employed at any company and have a side business that generates income. Which could persist indefinitely. They do not have to become a full-time entrepreneur. All the way to the venture-backed, high-pressure world of Silicon Valley.

I don’t think that all of the standards in Silicon Valley are congruent with 4-Hour Workweek. However, the general principles — maximizing per-hour output, 80-20 analysis as applied to customer services, batching tasks — all apply to startups better than in any other environment. Because the cost of being inefficient at a startup is so enormous. The only advantage you have is being lean, faster, and efficient. If you squander that by having fucked-up processes, you’re dead. You’re absolutely toast.