I Asked A $1.5 Billion Investor For Advice

The Dealroom with Shamus Madan

Sean O'Sullivan shares his entrepreneurial journey, from not being able to afford food to selling his company for $15 Million at 28 years old. He discusses the traits of a great founder and offers advice for young entrepreneurs navigating today's market. Sean reflects on his early programming days and the founding of MapInfo at age 21, detailing the motivations behind the company and the challenges faced in scaling and going public. He explores the role of venture capital and his transition to active investing with SOSV, focusing on deep tech. The conversation delves into risks, the value of investing in first-time founders, and megatrends in manufacturing and climate tech.

🐦 Follow the host: https://x.com/shamusmadan

📩 Join The Dealroom: https://dealroompodcast.com/subscribe

Learn More About SOSV: https://SOSV.com

(0:00) Introduction to Sean O'Sullivan and his journey (0:30) Sean O'Sullivan on making his first million and early life struggles (1:00) Traits of a great founder and advice for young entrepreneurs (1:54) The path to making the first million in the current market (3:30) Sean O'Sullivan on financial prudence and early career experiences (5:16) Sean O'Sullivan's early programming days and founding MapInfo at 21 (9:02) Motivation behind MapInfo and scaling the business (15:07) Overcoming challenges and the decision to go public with MapInfo (18:12) The role of venture capital and life after going public (22:49) Founding SOSV, deep tech focus, and the transition to active investing (24:34) Risks, learning curves, and the value of investing in first-time founders (32:36) Megatrends in manufacturing, climate tech, and key advice received