The Pursuit of Scrappiness 71% of Exit Funding in 2024 Came from Secondaries: Learn How It Works, When Your Startup Is Ready, and How to Negotiate the Best Terms w/ Rando Rannus (Siena Secondary Fund). Ep 199
Apr 8, 2025
48:56
Rando Rannus is a general partner at Siena Secondary Fund, the first and only dedicated secondary VC fund in the Baltics. With a unique background as both a company founder and operator—having built and sold an advertising business to MTG Group, and held leadership roles at Bolt and Viveo Health—Rando brings an operator’s mindset to venture investing. His fund specializes in providing liquidity to founders, employees, and early investors in high-growth scaleups, with a focus on the CEE and Nordic markets. Through Siena, Rando is pioneering a more flexible, founder-friendly approach to secondaries in a region where the concept is only now beginning to gain momentum.
On this episode we talk about:
- Why over 70% of tech exits in 2024 involved secondary deals and what’s driving this shift in the startup funding lifecycle.
- How Sienna’s model works, what types of companies qualify, and the benefits for founders and employees.
- Insight into how deals are valued, including discounting vs. premium pricing, share classes, and rights analysis.
- Why getting into companies like Bolt and Aura requires trust, timing, and strategic positioning.
- Rando’s personal story of transitioning from building startups to launching a fund and the lessons learned along the way.
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