The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified Investor Stories 439. From Angel Bets to Scalable Platforms, The Power of Listening, and Doing the Work Yourself (York, Dash, Madera)
Nov 10, 2025
Kyle York, founder of York IE, shares his shift from angel investments to larger checks for scalable companies. Somesh Dash from IVP discusses the vital art of listening, emphasizing how it enhances understanding of founder contexts. Paul Madera, co-founder at Meritech Capital, highlights the importance of conducting thorough diligence and understanding sector dynamics personally, rather than relying on others. Together, they offer invaluable insights for anyone looking to navigate the venture capital landscape.
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Invest Where You Can Add Scale-Up Value
- Kyle York shifted from angel bets to scaling-ready investments with larger checks and operator support.
- He finds the highest value in helping companies build operational plans, product scalability, and capital strategy.
Lead With Listening In Founder Conversations
- Listen more and talk less when meeting founders to uncover the real issues and context.
- Ask one or two focused questions, learn where the founder is mentally, and save broader advice for later interactions.
Do Your Own Diligence
- Do your own diligence and avoid outsourcing the core assessment of an opportunity to others.
- Deeply understand sector dynamics and company specifics to avoid making bad investment decisions.