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.

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[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

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A conversation with David and Ben from the Acquired podcast