What do you learn after building companies across five generations, and investing in thousands more?
David S. Rose has been early to nearly every wave: PCs, the internet, mobile, and now AI. As the founder of Gust, he didn’t just invest in startups, he built the infrastructure that powers how startups raise money globally.
He’s a serial entrepreneur, one of the most active angel investors in the world, founder of New York Angels, and the architect behind Gust, which now supports over 2 million founders and most major angel networks worldwide.
In Today’s Episode We Discuss
- 00:01– Intro & David S. Rose background
- 00:24– Early entrepreneurial beginnings
- 02:30– College ventures & first hustles
- 03:30– First job with Senator Moynihan
- 04:40– Real estate career & early tech adoption
- 05:20– Inventing proptech
- 06:50– First startup experiences
- 08:00– WristMac and early wearable tech
- 10:30– Mobile messaging startup
- 13:30– Accidental Series A raise
- 16:00– Wireless software & early telecom
- 17:30– Internet disruption
- 18:00– AirMedia & wireless internet vision
- 22:00– Dot-com boom & expansion
- 23:40– Dot-com crash & shutdown
- 24:40– Transition to angel investing
- 25:30– Founding New York Angels
- 26:30– Building Gust platform
- 29:00– Gust Launch & company formation
- 30:00– Writing books & Quora
- 33:00– AI impact on startups
- 35:00– USREM & real estate marketplace
- 37:00– Current ventures & roles
- 39:00– Singularity University origins
- 42:00– Exponential technology & Ray Kurzweil
- 49:00– AI, AGI, and future predictions
- 52:00– Impact of AI on venture capital
- 54:00– Future of work & unemployment thesis
- 58:00– UBI and economic restructuring
- 01:00:00– Abundance & societal shifts
- 01:01:30– Entrepreneurship in AI era
- 01:03:30– Healthcare, robotics, and tech progress
- 01:05:00– Founder mindset & entrepreneurship
- 01:07:30– Startup success traits
- 01:09:30– Investment decision framework
- 01:11:30– Closing thoughts & where to find David
Along the way, he shares lessons from decades of building through booms, crashes, and paradigm shifts—and why today’s founders are playing a completely different game.
“If a machine can do your job better, faster, and cheaper… by definition, that job disappears.”
“Entrepreneurs are like cockroaches. You can’t kill us.”
From selling firewood on his first day of college to powering global startup ecosystems, David’s story is a reminder: the tools change, the stakes get higher, but the mindset that builds companies stays constant.
Follow David S. Rose on LinkedIn: LinkedIn David S. Rose on X: X