The Sure Shot Entrepreneur

Gale Wilkinson, founder and managing partner at Vitalize Venture Capital, shares her wisdom on building startups with entrepreneurs. Gale talks about investing in the future of work and future of learning technologies, and highlights the questions she asks founders to understand their north star.

Joan Schmit, professor of risk and insurance at the Wisconsin School of Business, talks about risk management in business. As the program lead of Creative Destruction Lab-Wisconsin Risk Stream (CDL Risk), Professor Schmit discusses the objectives of the program, and gives examples of how connecting mentors and entrepreneurs through it is helping to improve society.

Schwark Satyavolu, a General Partner at Trinity Ventures, shares lessons from his many years of experience as a founder, operator, technology executive, and now an investor. Schwark talks about unwillingly getting into FinTech when he was building Yodlee, and how he got into investing in crypto startups. He also gives an interesting explanation as to why he likes investing in naive fast learners.

Winter Mead, the founder and CEO of Coolwater Capital, tells us about Coolwater, a new organization that’s changing the way venture capital investors build new firms. Winter takes us behind the scenes to show us how venture capital works and how LPs think about the industry.

Andy Kangpan, a Principal at Two Sigma Ventures, shares his experience supporting founders building enterprise software, cybersecurity, and crypto startups. Andy talks about the growth of decentralized finance (DeFi) and gives real-life risk management tips for entrepreneurs and investors wishing to venture into DeFi.

Paige Doherty, a founding partner at Behind Genius Ventures, shares her lessons from setting up her VC firm and writing her book ‘Seed to Venture’ about the venture process. Paige elaborates on her investment discipline and why she likes investing early in the future of work and future of play startups.

Jonathan Heiliger, General Partner at Vertex Ventures, talks about how the startup ecosystem has changed, and explains why founders DO/DON’T need to be in Silicon Valley. Jonathan also sheds light on the problem of matchmaking. He proposes solutions for ensuring that founders meet and partner with investors who are fit for them.

Mark Suster, General Partner at Upfront Ventures, talks about how he transitioned from being an entrepreneur to investing in startups. Mark elaborates his Lines and Dots technique for evaluating founders. He also points out some fundraising mistakes to avoid, especially when the capital market is undergoing correction.

Michael Cardamone, CEO and managing partner at Forum Ventures (formerly Acceleprise), demystifies the effects of public market volatility on startups. Michael gives his perspectives on the recent market downturn, and his advice for founders building B2B SaaS companies on how to manage market volatility. He also gives more details about how he looks at opportunities when he invests in startups.

Matt Harris, Partner at Bain Capital Ventures, talks of how he wanted to become a big fish in a small pond when he started investing in fintech. How has that turned out for him two decades later? Matt elaborates his practical approach when evaluating new investments, and gives tips for managing a startup’s expenses to ensure sustainability.