Revisiting "The Ideal Bootstrapped Business" with Jason Cohen

Jason Cohen’s talk “Designing the Ideal Bootstrapped Business” from 2013 is a classic in the bootstrapper canon. In this episode, Jason joins Adam and Ben to see how the talk holds up a decade after its creation.


00:00 Intro
00:27 Designing the ideal bootstrapped business
06:53 Recurring revenue vs one-off sales
13:30 Getting all the LTV up front
18:31 Product validation
24:56 Creating a cash machine
26:05 Where does growth come from?
41:25 Annual prepays
46:41 Increasing your prices
51:56 What new advice is there since this talk?
59:00 What about freemium?
01:03:39 What happens next?
01:08:58 Picking an idea that's compatible with the life you want to live
01:12:16 Ideas for Tailwind


Creators and Guests

Ben Orenstein
Ben Orenstein
Co-founder and CEO of Tuple.
Jason Cohen
Jason Cohen
Keyword, buzzword, half-truth, adjective, hey look at me!(founder of two unicorns:,
Revisiting "The Ideal Bootstrapped Business" with Jason Cohen
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