How to Choose the Door That Opens More Doors

Choosing a different path can lead to more opportunities and make up for past shortcomings. By being willing to explore new areas and take risks, one can avoid being confined to a single niche. Making decisions that seem unexpected but are personally intriguing can lead to new and exciting possibilities.

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Simen Strøm Braaten

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Brought to you by Eight Sleep’s Pod Cover sleeping solution for dynamic cooling and heating, Secureframe automated security and privacy compliance platform, and AG1 all-in-one nutritional supplement.

Welcome to another episode of The Tim Ferriss Show, where it is usually my job to deconstruct world-class performers to tease out the routines, habits, et cetera that you can apply to your own lives.

This is a special episode and a turning of the tables. This time, legendary investor Bill Gurley interviews me, and the recording is from earlier this year at SXSW in Austin, TX. The conversation explores some of my lessons learned and favorite findings over the last two decades in areas like entrepreneurship, tech, and podcasting. I throw in some favorite books and other spice to keep things interesting.

Bill Gurley (@bgurley) has spent more than 20 years as a general partner at Benchmark. Before entering the venture-capital business, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at Credit Suisse First Boston. Over his venture career, he has worked with such companies as GrubHub, Nextdoor, OpenTable, Stitch Fix, Uber, and Zillow.

For more takeaways from his incredible investing career, you can find my interview with Bill at tim.blog/billgurley.

As a side note, my 2007 SXSW speech that I mention in the interview is what started it all, in many senses. It’s what put my first book, The 4-Hour Workweek, on the radar of influential bloggers and bigger media outlets, ultimately landing it on The New York Times Best Sellers list, where it stayed, more or less, for the next seven years. It’s been a wild ride.

You can hear that 2007 presentation at tim.blog/sxsw.

One last thing: Hugh Forrest, if you’re listening, thank you again for giving me a shot way back in the day!

Please enjoy!

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[06:32] From Princeton to podcasting.

[07:39] How a disenchanted entrepreneur became a reluctant author.

[14:22] Angel investing and The 4-Hour Body.

[16:40] Investing rulesets and takeaways.

[19:09] How a choice location maximizes serendipity.

[20:42] Why did I back away from angel investing?

[22:28] Entering the blogosphere.

[27:02] Why podcasting?

[28:33] Early and enduring lessons for improving the craft.

[31:37] What makes a successful podcaster?

[34:57] The power of direct communication with one's audience.

[38:48] Leveraging a lean infrastructure.