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INTERVIEW SNAPSHOT · COVERED IN THE REPORT'S SECTION 9 · SECONDARIES

Exploring Venture Secondaries Fund

In venture capital, everyone talks about chasing the next rocket ship, but few talk about getting liquidity before the IPO. That's where secondaries come in.

MAY 202529 MINGUEST · RANDO RANNUS

NAV DISCOUNT PREMIUM SNAPSHOT
If you do your homework, there's alpha hiding in the discounts.
Rando Rannus · on where the alpha sits in secondaries
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€100BStartup market cap in Central Eastern Europe, with an annual liquidity need of at least €2–3B
$120BGlobal secondaries market last year, growing roughly 15–20% a year
1% vs 25%Secondary funds that fail to return 1x, against a quarter of early-stage funds
€1–5MSiena's ticket size, the mid-market gap between angels and the large international funds
ABOUT THE EPISODE

Rohit Yadav sits down with Rando Rannus, Partner at Siena, the first dedicated VC secondary platform in Central and Eastern Europe (CEE). Rando is helping build a secondaries playbook in a region known for unicorns like Bolt and Vinted, but where liquidity has lagged behind.

We explore:

  • Why secondaries are not just a distressed exit path, but a strategic allocation.
  • The different flavors of secondaries: company-level, GP-led, LP stake, and what's maturing fastest in Europe.
  • Siena's focus: mid-market deals ($1M–$5M), growth-stage scaleups, and deep local networks.
  • Why secondary returns rival early-stage VC, with lower risk and shorter duration.
  • Why CEE's €100B startup market is ripe for secondary liquidity, but underserved.

We also unpack:

  • Why the 'premium-only' hype around top names like Stripe and OpenAI skews the market.
  • How secondaries help founders de-risk without checking out.
  • Why most deals go wrong when investors skip access, info rights, or proper structuring.
  • What LPs are asking about secondaries (and why half of Siena's LPs were new to VC).
  • The growing interest from GPs and LPs, despite most of Europe still being early in the game.
IN HIS WORDS
MENTIONED

FUNDS & BUYERS

FUND

Siena Secondary Fund

Launched in 2021; company-level secondaries in scale-ups originating in Central Eastern Europe and the Nordics. No LP stakes or continuation funds yet.

LARGE BUYERS

Industry Ventures, G-Squared, StepStone, Lexington, Goldman Sachs

The firms operating above Siena's ticket range, on deals of $10M and up.

US FIRMS

Sequoia, Accel

Legally restructured in order to invest more into secondaries.

LP

EIF and local government fund-of-funds

The single LPs behind the first generation of CEE funds from the early 2010s, which is why LP liquidity pressure has been limited so far.

COMPANIES

PORTFOLIO

Bolt

One of the first secondaries the team did; Siena has invested every year for the past four years, and their analysis puts it above its last round even as it trades at a discount.

TENDERS

Vinted, ElevenLabs

Large oversubscribed tenders at a premium to the last round, Vinted's ran to a few hundred million.

PREMIUM NAMES

Stripe, SpaceX, OpenAI

The top-name side of the split market, where tenders happen at a premium.

PEOPLE & NUMBERS

GUEST

Rando Rannus

Partner at Siena; came from consulting in the early 2000s, exited his own startup in the 2010s, then joined two GPs with investment banking and early VC backgrounds in CEE.

HOST

Rohit Yadav

Investments thought leader, Big Book of VC.

SCREEN

The target company profile

At least €10M annual revenue, growing 50% or faster, valued north of €100M.

FUND SHAPE

Seven-year fund life, 20–25% IRR

Against 10 to 12 years in early stage; Fund I holds 10 companies, Fund II is planned for 15.

SNAPSHOT

Exploring Venture Secondaries Fund →

The full written snapshot of this interview on the Rethink site.

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