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A conversation with David and Ben from the Acquired podcast


David Rosenthal and Ben Gilbert — of the Acquired podcast — invited me to San Francisco for a discussion on our mutual obsession: spending every waking hour studying the history of entrepreneurship and sharing those lessons on our podcasts.


Come see a live show with me and Patrick O'Shaughnessy from Invest Like The Best on October 19th in New York City.

Get your tickets here!


Follow Acquired in your podcast player here or at Acquired.fm

This episode is brought to you by: Tiny: Tiny is the easiest way to sell your business. Tiny provides quick and straightforward exits for Founders. Get in touch with Tiny by emailing hi@tiny.com.

[3:00] David’s time with Charlie Munger

[5:30] Henry Flagler after Standard Oil

[8:30] What makes a great biography, and how to capture all sides of complex characters?

[11:00] Studying history is a form of leverage to achieve success

[13:00] How do we figure out what the true story is for an episode we're doing?

[20:30] Silicon Valley should focus more on durability than growth

[21:30] How David got into reading biographies and podcasting

[25:40] What were each of their influences before starting Acquired and Founders?

[35:30] How to suck less over time

[37:30] What motivates, Ben, David, and David to get better?

[45:00] Dead ends: business model changes, paid podcasts, changing the name to “Adapting”, and Senra's “Autotelic”

[51:30] “You’re not advertising to a standing army, you’re advertising to a moving parade”

[56:00] Comparison of podcasting business models

[1:00:10] Senra’s insane Readwise "healthy twitter" habit

[1:04:30] Is it possible for the ultra-wealthy not to mess up their kids?

[1:14:30] The fleeting moments you get to spend with your kids

[1:17:00] The value of building relationships with best-in-class peers

[1:19:30] How the book publishing industry works

[1:28:45] How to differentiate yourself as an investor in 2023?

[1:38:30] The greatest historical examples as content marketing

[2:02:00] The best businesses are cults (and Senra starts one on the episode)

[2:07:00] Senra gives feedback to Ben and David on Acquired episode format

[2:15:30] Steve Jobs’ 1997 product matrix

[2:17:00] The moral imperative to market products that help people

[2:23:00] Ray Kroc and Steve Jobs: deeply flawed founders

[2:23:30] The founders we idolize are world-builders

[2:28:00] When yachts and jets are underpriced assets

[2:32:00] How to compete when money is cheap vs. when there are real interest rates

[2:39:30] When Ben and David have fixed broken episodes in post-production

[2:44:30] Why masters of craft are so interesting to study

[2:45:30] Should you listen to advice?

[2:51:00] David’s first job detailing cars

[2:52:30] The Cuban experience immigrating to Miami

[3:01:00] College entrepreneurship programs

[3:04:00] Ben’s experience learning UNIX as a kid

[3:08:30] David remembers Tim Ferriss guest lecturing in college

If you have scrolled this far and still haven't followed Acquired in your podcast player please do so here!

Ikke spilt