Driving Alpha: The Art of Low-Velocity, High-Conviction Investing With Rebecca Kaden

Driving Alpha

Rebecca Kaden is a Managing Partner at Union Square Ventures, a New York-based venture capital firm. She began her career as a journalist, and prior to USV, was a General Partner at Maveron, a consumer-focused early-stage fund. Rebecca was born in New York City. She studied English and American Literature at Harvard and received her MBA from Stanford.

Episode Chapters

(00:00) Introduction

(2:46) Rebecca Kaden highlights the role of early mentorship in a successful VC career

(6:27) How Rebecca’s liberal arts background influences her VC perspectives

(8:29) Union Square Ventures' thesis-driven approach to investing

(15:00) USV's investment strategy in the healthcare sector

(17:04) How USV collaborates with other VCs and values syndicate participation

(22:04) Why should investors prioritize businesses with unconventional models?

(26:42) The philosophy behind the concept of "high conviction, low velocity" investing

(33:42) USV’s unwavering commitment to decentralization and the future of blockchain investments

(39:42) Rebecca’s advice for junior VCs

In this episode…

Can high-conviction investments yield the results venture capitalists strive for? What does it take to pursue an unusual and non-competitive market? With a deep understanding of the industry, a journalist turned VC specialist brings a unique perspective to the untapped potential in sectors like healthcare and the revolutionary applications of AI and blockchain technology.

In this episode of Driving Alpha, Steve Brotman chats with Rebecca Kaden, Managing Partner at Union Square Ventures, about the strategies that drive USV's investment philosophy. Rebecca dives into the value of thesis-driven investments, USV’s unwavering commitment to decentralization, and the future of blockchain investments. She also explores the importance of mentorship, collaborating with other VCs, and a deep understanding of markets.

Mentored by Bill Campbell, Rebecca Kaden leverages her journalism background and business acumen to drive investment in companies reshaping entire industries. Her insights into Union Square Ventures’ thesis-driven investment approach reveal how low investment velocity along with high conviction can make all the difference. From innovative healthcare companies like Thirty Madison to unconventional investments in platforms like Team Shares, USV’s philosophy centers on finding and nurturing non-traditional opportunities. With a significant portion of the firm’s portfolio dedicated to decentralization and cryptocurrency, Rebecca highlights how investors can cultivate a portfolio characterized by strong conviction and innovative solutions by staying informed on emerging technologies.