E129: The Number #1 Predictor of Startup Success w/Ken Smythe

In this episode of How I Invest, I connect with Ken Smythe, founder of Next Round Capital, to discuss his journey in private markets, lessons from hedge fund management, and the future of thematic investing. Ken shares insightful stories about spotting talent, using key executive moves as signals for investment opportunities, and the rise of AI and defense technology. We also explore the challenges facing venture capital and private equity in today’s market, including liquidity bottlenecks and the hunt for alpha in a rapidly evolving landscape. Ken's personal story of resilience and his passion for innovation shine through in this inspiring conversation. Highlights: Key Signals in Early-Stage Investing: Why tracking executive moves from established companies like Apple or Stripe to startups can offer a major edge in spotting emerging opportunities. AI's Evolution: The current state of AI innovation compared to the early days of the internet and the need for sustainable business models to monetize AI advancements. Defense Tech: How startups are disrupting traditional players like Lockheed Martin and General Dynamics with cutting-edge technologies tailored to modern battlefields. Hedge Fund Insights: The importance of diversification, risk management, and identifying specialized talent in building successful multi-strategy hedge funds. Secondary Markets: The growing role of VCs, family offices, and retail investors in accessing shares of companies like SpaceX and how liquidity challenges are reshaping private equity strategies. Thematic Investing: From AI chatbot agents to defense technology, Ken outlines the trends and themes that he believes will dominate in 2025 and beyond. Personal Resilience: Ken’s inspiring journey of launching his own firm amid personal challenges, underscoring the importance of seizing opportunities and living with purpose. -- Guest Bio: Ken is the founder of Next Round Capital, a firm specializing in secondary investments, co-investments, and niche opportunities in technology and AI. With a background in hedge fund management and a focus on thematic investing, Ken leverages his deep network and expertise to identify groundbreaking opportunities in private markets. He is passionate about innovation and building meaningful relationships in the venture ecosystem. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com . #VentureCapital #VC #Startups #OpenLP -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Ken Smythe: https://www.linkedin.com/in/ken-smythe/ Links: Next Round Capital: https://www.nextroundcapital.com Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com (0:00) Episode preview (1:37) Key Executive Movements in Tech (3:38) Adverse Selection in Venture Capital (4:35) Investment Trends for 2025 (6:27) Focus on Defense Technology Investments (8:06) Managing Liquidity in Venture Portfolios (10:36) Analyzing SpaceX's Investment Potential (11:45) Hedge Fund Insights from a $5 Billion Experience (14:37) Strategies for Recruiting and Evaluating Portfolio Managers (24:50) The Art of Referencing and Backchanneling (26:01) Spotlight on Next Round Capital (27:39) AI Investment Landscape Analysis (28:34) Business Model Significance in Tech Sector (29:52) Closing remarks