In this masterclass on venture capital secondaries, Rando Rannus, GP at Siena Secondary Fund, outlines why the traditional 10-year VC model no longer reflects market reality. As companies stay private longer and IPO timelines stretch to 15–20 years, liquidity solutions must evolve.
Siena focuses on secondary investments in high-growth scale-ups across Central and Eastern Europe and the Nordics, targeting category leaders such as Bolt, Oura, Booksy,
and Preply. The strategy centers on providing partial liquidity to early investors, founders, and employees—often enabling them to reinvest into the ecosystem and strengthen Europe’s innovation flywheel.
Rando challenges common misconceptions about VC secondaries, particularly the overemphasis on “average discounts.” Instead, he argues that disciplined underwriting, access to data, cap table analysis, and understanding liquidation preferences are far more critical.
The conversation also explores:
Why secondary markets are structurally expanding
The downside risk asymmetry compared to early-stage VC
Europe’s liquidity inefficiencies vs. the U.S.
Estonia’s startup ecosystem and the “Skype moment”
The role of pension funds and institutional capital in strengthening venture markets
Governance considerations for startups preparing for future liquidity events
Ultimately, this episode positions VC secondaries not as opportunistic arbitrage—but as an essential liquidity infrastructure for a maturing private market.
