
A $3.6B founder's honest take on the software market right now
Jul 7, 2026
Show Notes:
(0:00) Story of Box
(06:30) Enterprise Over Consumer
(10:00) Turning Down Huge Acquisition Offers
(17:05) Angel Investing, Missed Bets, and Investing in Your P&L
(23:00) Aaron’s Contrarian AI Takes: More Jobs, More Work
(30:00) Founder Anxiety, Therapy, and Surviving the CEO Grind
(38:45) The Business Strategy Books Aaron Swears By
(48:00) AI Tools, Software Stocks, and Why SaaS Isn’t Dead
