The Sure Shot Entrepreneur

Maryanna Saenko, Co-founder and Partner at Future Ventures, talks about what attracts caring investors to venture capital. Maryanna shares examples of her successful investments in deep tech and gives useful tips to help technical founders convince the investor in the first meeting. In this episode, you’ll learn: 4:13 How can caring venture capitalists help in creating a more verdant future that i...

Ayush Jain, a Senior Associate at Revolution’s Rise of The Rest seed fund, shares his career journey from engineering to product management to investing in entrepreneurs that are outside the traditional tech hubs. Ayush highlights some important trends that are disrupting the healthcare industry. He also explains why the “failing fast” mantra that people ascribe to entrepreneurship can be misleadi...

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. In this episode, you’ll learn: 4:44 What investors are looking for when they ask “Why did you pick thi...

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. In this episode, you’ll learn: 7...

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. In this episode, you’ll learn: 3:25 Why supporting emerging managers is critical to the growth of the venture capital ecosys...

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.  In this episode, you’ll learn: 4:15 Risk-taking for venture capital investors m...

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. In this episode, you’ll learn: 3:15 Entrepreneurs who are customer centric and who have a high...

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. In this episode, you’ll learn: 4:27 A lot has changed in the startup...

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. In this episode, you’ll learn: 6:27 Entrepreneurs need different kinds of help...

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. In...

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. In this episode, you'll learn: [3:36] Great investors are...

Vikrant Shaurya, the CEO and founder of bestsellingbook.com , shares his unusual entrepreneurial journey. Vikrant narrates how he got early believers to support him in building his first company after dropping out of college. He talks of how he has used the lessons he learned from his initial entrepreneurial failure to build a world-renowned publishing company. In this episode, you’ll learn: [1:44...

Nuno Gonçalves Pedro, founder and managing partner at Chamaeleon, talks about founding his  new VC firm and how they’re using technology to manage investment processes. Nuno reiterates the importance of entrepreneurs spending more time to know investors before meeting them. He also shares useful dialogue tips for founders to continually improve how they communicate with investors. In this episode,...

Sam Toole, Principal at Primary Venture Partners, talks about opportunities for building healthcare solutions, and how building a healthcare business is different from other businesses. Sam also highlights common mistakes that founders make when engaging with pre-partner level investors. In this episode, you’ll learn: [6:02] Regulatory and infrastructure changes that are accelerating opportunities...

Chris Wake, Founder of Atypical Ventures, talks about investing in engineers with empathy. Chris shares his unconventional ways of finding technical founders, and gives examples of startups reimagining and transforming the world through scientific innovations. In this episode, you’ll learn: [6:55] Empathy unlocks technical entrepreneurs’ potential to build innovations that are truly transformative...

Zain Jaffer, Partner at Blue Field Capital, shares his journey through entrepreneurship and how he switched to investments. Zain talks about how being a former founder helps him to support the founders he backs as they scale their companies. He also highlights the need for founders and investors to focus beyond first-world problems and solve for real impact. In this episode, you’ll learn: [4:24] D...

Dan Rosen, Founder and General Partner at Commerce Ventures, talks about the evolution of fintech over the last two decades. Dan shares real-life examples of innovative fintech entrepreneurs building solutions that touch customers and businesses in a meaningful way, and his thoughts on whether or not now is still a good time to start a company in the fintech space. In this episode, you’ll learn: [...

Heather Hartnett, General Partner and CEO of Human Ventures, shares how she identifies ‘futurists’ to back them until the market sees their value. Heather talks about supporting early-stage entrepreneurs through ‘Humans in the Wild’ (the firm’s business incubator) and explains how valuation affects a startup’s future. In this episode, you’ll learn: [3:40] Why VCs like to invest in ‘futurists’ [9:2...

Charles Hudson, Managing Partner and Founder of Precursor Ventures, talks about how he founded Precursor Ventures and why he is unafraid to back unproven first-time entrepreneurs. Charles gives useful tips for founders embarking on finding product-market fit, and shares his thoughts on bridge funding. In this episode, you’ll learn: [3:57] Starting early in venture capital as an undergraduate; what...

Julieta Moradei, Partner at Hometeam Ventures, talks about their vision "to close the housing gap" through investing in ambitious founders developing revolutionary technology for the construction industry. Julieta shares an inspiring story of how they created Hometeam Ventures from a non-profit, about being a first-time fund manager, and authentic examples of startups making phenomenal innovations...

Lucas Timberlake, a Partner at Fintech Ventures Fund, talks about investing in game-changing fintech and insurtech startups. Lucas explains why he looks for founders who are coachable and knowledgeable about the regulatory requirements for their business and shares an unconventional pitch story about one of his recent investments. In this episode, you’ll learn: [2:53] Fintech Ventures Fund’s uniqu...

Patrick Eggen, Founding General Partner at Counterpart Ventures, talks about the different facets of corporate venture capital (CVC), where it has a real edge in the startup world, and why entrepreneurs should work with CVC investors. Patrick debunks some myths around CVC and shares his observations on how CVC and venture capital has evolved over the last decade. In this episode, you’ll learn: [2:...

Jacob Haar, Founder and Managing Partner at Community Investment Management, talks about debt capital and its social impact on financial inclusion. Jacob shares CIM’s inspiring mission of improving inequality through innovation lending, clarifies how equity and debt investors view startup investment opportunities differently, and gives founders useful tips for approaching venture debt investors. I...

Alexa von Tobel, founder and managing partner at Inspired Capital, shares how she built her first startup LearnVest at 23 and later co-founded Inspired Capital to improve access to startup capital. Alexa looks for tenacious and highly committed founders with an ‘always be learning’ attitude. In this episode, you’ll learn: [3:55] Did dropping out of Harvard Business School to start a company in the...