Top 10 Takeaways from Tim Ferriss

“A cross between Jack Welch and a Buddhist monk.”

That’s how The New York Times sums up author, entrepreneur, and investor Tim Ferriss.

Perhaps best known for his books The 4-Hour WorkweekThe 4-Hour Body, and The 4-Hour Chef — all of which hit No. 1 on the NYT bestseller list — Ferriss is also a force to be reckoned with on the startup scene. Ranked by CB Insights as No. 6 on its 2014 list of “Top 20 Angel Investors,” he’s an investor or advisor in dozens of companies including Uber, Facebook, Twitter, and Evernote.

On Sept. 26, Ferriss sat down for a fireside chat with Jason Calacanis for a This Week in Startups LIVE event in San Francisco. What followed was a captivating conversation, with Ferriss dropping knowledge on entrepreneurship, pitching investors, writing, meditation, and more.

Here are some of the key points Ferriss shared with the audience, or what I like to call “The Top 10 Takeaways from Tim.”

1. Meaning of The 4-Hour Workweek

While “The 4-Hour Workweek” certainly made for a catchy book title, Ferriss clarified that the concept is not necessarily about working just four hours per week but about being 10x more productive. It’s also about setting priorities. As he explained, “It’s about thinking about what your life looks like in as focused a way as you think about your IPO.”

2. Taking Smart Risks

By most standards, Ferriss is pretty extreme when it comes to experiments, serving as a guinea pig to test nutritional theories, cutting-edge medical procedures, and more. To be sure, these experiments don’t always go as planned (such as the time he got a staph infection from having stem cells injected into his arm in an effort to alleviate tennis elbow.)

But Ferriss made one thing clear: he doesn’t take risks blindly. Instead, he emphasized that he does a lot of research and carefully evaluates the potential benefits and consequences before undertaking any experiment, prompting Calacanis to dub Ferriss “Steve-O with research.”

3. Valuing Your Reputation

As a result of his books, as well as his popular blog and podcast (frequently rated No. 1. across all of iTunes), Ferriss has amassed a serious fan base. And, as much as he values the startups he’s invested in, he revealed that he actually places an even higher premium on these fans.

Why? Companies, especially startups, will come and go, but as long as you’ve built trust, your fans will stick with you through thick and thin. If that trust were broken, it would be extremely challenging to rebuild, which is why he’ll only promote products he truly believes in.

4. Syndicating via AngelList

For Ferriss, the decision to begin angel investing was largely motivated by a desire to diversify, both in terms of his financial assets and his identity. (No one wants to be the “4-Hour” guy forever!)

An advisor to AngelList, Ferriss has become a power player on the platform and believes the introduction of syndicates has only improved the landscape for angels. He said, “A-list VC firms are now playing nice with angel syndicates because syndicates have the power to drive up the price.”

5. Pitching Tim

Beyond AngelList, the most effective way to pitch Ferriss is through a founder of a company in which he’s already invested. But it’s not enough to track down a founder and persuade him or her to send Tim an email; you also have to convince the founder to become an advisor, join the board, or, even better, invest in your company. As Ferriss explained, if the founder isn’t going to have some skin in the game, the intro doesn’t mean much.

6. Pitching Tim 2.0 (#Fail)

When Calacanis asked for the worst ways to pitch him, Ferriss had an immediate response: when he’s in the midst of using the bathroom or is out to dinner with his girlfriend.

It should be obvious that bathroom visits and dinner dates are not the right occasions to launch into your elevator pitch. But both scenarios have happened to him multiple times, so it seems like some folks need a reminder. Everyone got it now?

7. Making Your Writing Effective

Ferriss admitted that he doesn’t have the most beautiful prose in the world but thinks he’s found success as an author in part because he is an effective teacher. By explaining concepts in clear terms and providing sufficient detail without unnecessary fluff, he makes it easy for the reader to replicate his experiments and implement his advice.

8. Making Your Writing Interesting

Of course, having an effective writing style would be pretty useless if the content itself were dull. Thankfully, Ferriss has a long list of experiments and adventures under his belt, all of which provide him with rich material. He advised, “If you want to have interesting writing, do crazy, interesting stuff.”

9. Becoming Focused

Ferriss explained that one of his motivations for writing is to clarify his thinking. This applies to his books and blog but also to his daily practice of “morning pages.” Each day upon waking, he sits down and writes three pages. The topic doesn’t matter; the purpose is simply to clear his mind so he can be more focused throughout the day.

10. Meditating

Speaking of clearing one’s mind, Ferriss discussed the benefits of meditation. He explained that, although it can feel challenging to squeeze it into your schedule, if you don’t set aside adequate time each day for quiet and reflection, you’ll just wind up having to make even more time for it down the road. Paraphrasing a Zen proverb, he said, “If you can’t make time for 30 mins, you’ll need three hours.”

For more advice from Ferriss, watch the full interview on This Week in Startups.

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