Modest Proposal – Better, Cheaper, Faster: Why Companies that Reduce Friction Win – [Invest Like the Best, EP.193]


Before getting to this week’s guest, an announcement: starting Thursday we will be introducing a new series of interviews. Be sure to check this same podcast feed in two days to learn more.

My guest this week goes by the pseudonym Modest Proposal. He’s both a close friend, and one of the most respected thinkers on financial twitter. I field more inbound questions about him than just about anyone, and you’ll see why in this episode. We discuss many of the biggest themes in today’s stock market, from consumer to technology to marketplace and local home services. As always, Modest brings specific insight and general frameworks to the discussion. I talk to him as often as I can because I learn something new every time, and this discussion was no exception. Please enjoy my conversation with Modest Proposal.

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Show Notes

(2:37) – (First question) – How investing is about underwriting the future

(5:42) – Essential tools to underwrite the future

(9:02) – Increasing returns to scale as the most important tool

(11:36) – Example of silly investments

(14:00) – Ideas of consumer signal and non-linear beahvior

(16:30) – Why he was blown away by

(19:08) – How businesses are targeting facilitating transactions

(23:11) – Ecommerce and digital penetration in business

(27:56) – His thoughts on the extinction of so many businesses as a result of the pandemic

(32:26) – Chart tracking Product to service against homogeneous to heterogenous

(43:51) – Other features of business that fascinate him

(46:29) – Ideas that pique his interest right now

(51:20) – Case study: IAC/InterActiveCorp

(59:36) – Barry Diller’s superpowers

(1:01:17) – Why he’s spent so much time exploring IAC/InterActiveCorp

(1:02:56) – Related companies to explore

Learn More

For more episodes go to

Sign up for the book club and new email newsletter called “Inside the Episode” at