How to Buy the Right Insurance for Your Startup

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Vouch is the insurer recommended by Carta, Brex, Vanta and more. In this season, we're doing something new with Vouch. We are going to dive deep specifically into how buying the right insurance for your company works so you can be a smarter customer no matter who you choose to work with. It's typically only a few hundred bucks for a year of coverage.

ACQ Sessions returns with David Senra of the Founders Podcast. David is one of our very favorite people in the world — it’s impossible to spend an hour (or 3!) with him and not come away inspired to go take over the world. This conversation is an “extended, IRL version” of monthly calls that we do together where we share stories, swap life and podcast advice, and just genuinely enjoy sharing time with someone who shares our outlook and enthusiasm for the history of entrepreneurship. Pull up a chair, grab a beverage (or energy drink in David’s case) and join us!

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Topics:

(00:01) - Intro
(03:30) - David’s time with Charlie Munger
(06:00) - Henry Flagler after Standard Oil
(09:00) - What makes a great biography, and how to capture all sides of complex characters?
(11:30) - Studying history is a form of leverage to achieve success
(13:30) - How do we figure out what the true story is for an episode we're doing?
(21:00) - Silicon Valley should focus more on durability than growth
(22:00) - How David Senra got into reading biographies and podcasting
(26:10) - What were each of their influences before starting Acquired and Founders?
(36:00) - How to suck less over time
(38:00) - What motivates, Ben, David, and David to get better?
(45:30) - Dead ends: business model changes, paid podcasts, changing the name to “Adapting”, and Senra's “Autotelic”
(52:00) - “You’re not advertising to a standing army, you’re advertising to a moving parade”
(56:30) - Comparison of podcasting business models
(01:00:40) - Senra’s insane Readwise "healthy twitter" habit
(01:05:00) - Is it possible for the ultra-wealthy not to mess up their kids?
(01:15:30) - The fleeting moments you get to spend with your kids
(01:17:30) - The value of building relationships with best-in-class peers
(01:20:00) - How the book publishing industry works
(01:29:15) - How to differentiate yourself as an investor in 2023?
(01:39:00) - The greatest historical examples as content marketing
(02:02:30) - The best businesses are cults (and Senra starts one on the episode)
(02:07:30) - Senra gives feedback to Ben and David on Acquired episode format
(02:16:00) - Steve Jobs’ 1997 product matrix
(02:17:30) - The moral imperative to market products that help people
(02:23:30) - Ray Kroc and Steve Jobs: deeply flawed founders
(02:24:00) - The founders we idolize are world-builders
(02:28:30) - When yachts and jets are underpriced assets
(02:32:30) - How to compete when money is cheap vs. when there are real interest rates
(02:40:00) - When Ben and David have fixed broken episodes in post-productio
(02:45:00) - Why masters of craft are so interesting to study
(02:46:00) - Should you listen to advice?
(02:53:00) - The Cuban experience immigrating to Miami
(02:53:30) - Senra’s first job detailing cars
(03:01:30) - College entrepreneurship programs
(03:04:30) - Ben’s experience learning UNIX as a kid
(03:09:00) - David remembers Tim Ferriss guest lecturing in college

Note: Acquired hosts and guests may hold assets discussed in this episode. This podcast is not investment advice, and is intended for informational and entertainment purposes only. You should do your own research and make your own independent decisions when considering any financial transactions.