This episode is brought to you by:

Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 driveable global models handbuilt by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick.

Show Notes

(00:03:14) - (First question) - He talks about the nature of being interviewed about himself and his business

(00:06:14) - The development of taste and quality

(00:10:20) - CS Lewis tweet; The Inner Ring

(00:11:53) - Founders being heroes and motivating quietly from the background

(00:14:33) - The competitive advantages of enduring pain as a founder and investor

(00:16:14) - Overview the founding story of Oscar Health

(00:19:05) - Under which conditions the ‘why now’ matters more or less to him in investing

(00:21:30) - Whether or not the pleasures and pains of running Oscar are similar to an early-stage business

(00:23:18) - Learning to identify good problems and creating a business to solve it
(00:25:43) - He tells us about the birth story of Thrive Capital
(00:30:14) - Lessons learned from creating the first three Thrive funds moving into fund four

(00:33:35) - Industry wide competition today and models for building a firm in general

(00:37:44) - Talent, recruiting and seeing potential in younger generations of people

(00:39:38) - His felt experience and views on the immigrant mentality

(00:39:08) - How he harnesses his story and attitude within the business and his personal life

(00:43:07) - Determining individuals who want opportunities more than others for his team

(00:45:40) - Investments he made during the early foundation of Thrive that had significant impact

(00:46:53) - Whether or not he planned on Thrive being so concentrated
(00:49:12) - His analogy for investing in early versus late stage and styles of real estate investing
(00:52:08) - When a company is ready for 5th Avenue and mistaking a 3rd Avenue company for a 5th Avenue one

(00:54:22) - The current macro environment and how they affect his investment decisions

(00:57:52) - Giving AI companies computing power instead of money and the brilliance behind that innovation

(00:58:57) - Why he sold small stakes of Thrive
(01:00:13) - Setting and controlling his own ambition and maintaining purity that Thrive

(01:01:42) - How he manages the tension between Thrive and being a pure play investor
(01:03:10) - His philosophy on what makes a good product

(01:05:20) - What he thinks about the models like Mobile and Cloud

(01:08:10) - His absence from crypto and why he refrained during the boom in 2021

(01:10:33) - Thoughts about the opportunity set in FinTech today writ large

(01:12:04) - Other potential opportunity sets beyond what’s already been discussed

(01:13:39) - Lessons learned from his time spent with Marc Andreessen
(01:15:00) - Someone he believes is one of the greatest communicators
(01:15:43) - Lessons learned from Stan Druckenmiller, Henry Kravis, and David Geffen

(01:18:43) - Children fill a void you didn’t know you had and changes from becoming a father

(01:20:09) - Firm values he thinks are very important
(01:21:59) - Balancing magnitudes of capital between investment funds

(01:23:32) - Why he thinks founders choose Thrive

(01:26:39) - His most unusual interest he feels pulled back into time and again

(01:27:22) - What he finds intriguing about installation art

(01:29:15) - Vision as a key ingredient for founders

(01:30:13) - What he’s learned about negotiating with late stage investments

(01:32:19) - His view of the investment industry in the world today writ large

(01:35:56) - Aspects about Thrive’s story that he would like us to understand

(01:39:07) - Kareem Zaki’s successful healthcare investing track record

(01:40:19) - Other investment firms he would invest in
(01:42:48) - The kindest thing anyone has ever done for him