E133: Lessons from Investing in 2200 Startups (in 23 Minutes)

In this episode of How I Invest, I connect with Lorenzo Thione, Managing Director at Gaingels, one of the most active and inclusive venture syndicates in the world. Lorenzo discusses his philosophy on diversity, equity, and inclusion (DEI), the democratization of venture capital, and his thoughts on the AI revolution. From his experience building a portfolio of over 100 investments to lessons learned from co-founding PowerSet, Lorenzo provides invaluable insights for investors and entrepreneurs alike. Highlights: Philosophy on DEI: How the distribution of talent and opportunity shapes Gaingels' mission to bring inclusivity to venture capital. Gaingels’ Approach: Investing in companies that prioritize diversity in talent, governance, and capital while enabling LPs to invest with as little as $1,000. Venture Allocation: Advice for high-net-worth investors on diversifying their portfolios across stages, sectors, and liquidity horizons. Lessons from Uber: Why Lorenzo passed on the Uber seed round and how it shaped his investment philosophy. AI Investing: Insights into the evolution of AI, the importance of category-defining opportunities, and the impact of recent major investments in AI infrastructure. Angel Investing: The importance of backing founders you know and trust, and how personal relationships can lead to better investment outcomes. -- Guest Bio: Lorenzo Thione is a serial entrepreneur, investor, and expert in Artificial Intelligence. Currently, as Managing Director of Gaingels, he leads investments in AI, deep-tech, and consumer tech, promoting diversity in venture capital. He co-founded Powerset, an AI-driven search engine acquired by Microsoft and integrated into Bing. Beyond technology, Lorenzo is a celebrated Broadway producer, with productions like "Hadestown" and "The Inheritance," earning multiple Tony Awards. He also co-founded StartOut, supporting LGBTQ+ entrepreneurs. Born in Milan, he holds an M.S. in Computer Engineering from the University of Texas at Austin. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Lorenzo Thione: https://www.linkedin.com/in/lorenzothione/ Links: Gaingels: https://www.gaingels.com/ Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com . (0:00) Episode preview (2:52) Gaingels syndicate and low minimum LP investment strategy (5:15) Venture capital allocation advice for high net worth individuals (6:19) Diversification strategies within venture capital (8:37) Analyzing long-term venture capital returns (9:52) Gaingels investing access and strategic insights (13:03) Key lessons from early-stage angel investing experiences (16:56) Investing in AI and portfolio strategy considerations (19:37) SoftBank and Sam Altman's AI investment impact (23:29) Closing remarks