You Can't Time Early‑Stage Venture

This week on Swimming with Allocators, Earnest and Alexa chat with Anthony Giambrone, Partner at StepStone Group. Anthony shares his unconventional path from gas station manager and nightclub worker to leading a major global venture allocation platform. The conversation covers his break into investment banking, the scaling of GreenSpring into StepStone, and why relationships, EQ, and consistency across vintages matter more than market timing in venture. Key takeaways include the power-law nature of VC returns, how emerging managers and spinouts can stand out with a real edge and long-term relationship-building, why asset quality matters more than discounts in secondaries, and how AI, liquidity pressures, and longer private company lifecycles are reshaping the next decade of venture capital. Also, Rebecca Stuart, an employment-focused partner at Sidley, explains how she helps venture-backed companies navigate complex employment and co‑founder separations, equity and vesting pitfalls, evolving worker classification and pay transparency laws, and the fast-changing regulatory landscape around AI in hiring and employment decisions.

Highlights from this week’s conversation include:

• Anthony’s Background and Humble Beginnings (0:42)

• Importance of Empathy and Relationships in Venture (4:16)

• Applying Greenspring/StepStone Experience to Today’s Market (6:15)

• StepStone Venture Team, AUM, and Global Footprint (8:07)

• Why You Can’t Time Early Stage Venture (9:38)

• Vintage Volatility and Power Law in Venture Outcomes (11:23)

• How Founder Ambition Affects GP and Fund Diligence (14:28)

• Insider Segment: Co‑Founder Divorce (18:04)

• Using New Investments to Clean Up Equity and IP (21:43)

• Employees Demanding Human Review in AI‑Driven Processes (25:43)

• Fund Slot Constraints and LP Down‑Selection (28:33)

• Advice for New LPs on Capturing Upper Quartile Returns (31:36)

• Is Top Quartile Performance Still Good Enough? (33:08)

• Secondaries Strategy and Asset Quality Over Discounts (34:31)

• Liquidity Pressures, DPI, and GP‑Led Solutions (38:37)

• StepStone’s 10‑Year Lifecycle Partner Vision (40:35)

StepStone Group is a global private markets firm focused on providing customized investment solutions and advisory and data services to its clients worldwide. The firm’s venture capital and growth equity platform, built on the foundation of Greenspring Associates, manages $25B+ in AUM across primary fund investments, secondaries, and co-investments, as of June 30, 2025. Learn more at www.stepstonegroup.com.

Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com.

Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. 

The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only.

Learn more about your ad choices. Visit megaphone.fm/adchoices