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Show Notes

[00:03:56] - [First question] - His start as an entrepreneur in online game

[00:05:09] - His parent's reaction to selling his first company at fifteen

[00:05:57] - Starting a second video game company

[00:07:40] - The video game industry, being ahead of the curve in performance marketing, distribution, and operations

[00:08:49] - Notable two year lag between gaming innovation and other consumer sectors

[00:10:50] - What is happening today in gaming that may be a glimpse into the future

[00:12:41] - Key elements for creating a great gaming experience

[00:15:29] - Building a meta-game on top of the game itself to maximize engagement

[00:17:23] - Monetizing free to play games through in-game purchases

[00:20:25] - The most portable idea from fifteen years in gaming that can be applied to business

[00:22:02] - A future shift towards usage-based pricing models

[00:23:03] - His overall investment philosophy and strategy

[00:26:45] - Example of small a market with a high growth rate

[00:27:38] - Key elements of system elements and design when evaluating a business

[00:31:07] - What a flywheel looks like and investing in one such as Next Health

[00:33:24] - Working core actions versus giving credit ones that aren’t yet working but may drive desirable outcomes

[00:34:13] - Why don’t more investing firms have a flywheel?

[00:39:04] - Product Hunt as a standalone business and part of a self-reinforcing ecosystem

[00:40:17] - Emerging systems and ecosystem edges in the digital landscape

[00:42:17] - Potential barriers for crypto becoming widely adopted in a variety of ways

[00:44:29] - New frontiers and platform shifts like crypto that may unlock new doors for companies

[00:45:13] - Which person has rewired his brain in his lifetime the most

[00:47:13] - Weirdness around Stripe and Plaid when he first encountered them

[00:48:37] - Meta-games people in the industry are playing or should be playing

[00:51:25] - Controversial ideas around the business world today at large

[00:54:01] - Implications of shifting primarily towards a digital world

[00:54:14] - The kindest thing anyone has ever done for him