Rewriting the Rules: Rando Rannus on Secondary Markets and the New Era of Startup Liquidity

The European startup ecosystem is maturing rapidly, but with longer paths to exit comes a critical challenge: liquidity. While founders, early employees, and angel investors wait years for traditional exits, a new breed of investor is stepping in to bridge the gap. Rando Rannus, General Partner at Siena Secondary Fund, has built his career around solving this exact problem.

From his early days as a founding member of the Estonian Founders Society to leading one of Europe’s most active secondary funds, Rando brings a unique perspective on how liquidity markets are reshaping the startup landscape. With €50M Fund II and investments in regional champions like Bolt, Oura, and Veriff, he’s not just observing the evolution of European tech—he’s actively building the infrastructure that will power its next phase of growth.

Let’s start with something personal 🙂: You’re known for valuing balance and spending time with family while running a VC fund. Can you give us a glimpse into what a typical day looks like for you?

I wake up around 6:30 am, usually a bit earlier than other family members. This allows me to take about 20 minutes to do my morning routine exercise with bodyweight. This helps wake my body and mind like espresso, after which it’s easy to go and make breakfast for the kids. Once the kids are off to school, I take time to read industry news and settle in for the day. As for work, no day is similar—some might have more desk work, some more online video meetings, and some need to be spent actively networking at conferences and other events. It doesn’t matter whether I’m at home or abroad; I always find time for a longer walk with the dog or a run. Once the kids are back home, we find time to do some basketball shootouts and watch TV. The days end with bedtime reading or a good Netflix show.

You’ve described Siena as creating an “index fund of the best startups” from CEE and the Nordics. Can you walk us through how secondary investments work for founders and early employees who need liquidity, and why this approach is particularly relevant for the CEE/Nordic regions?

It’s already a known fact that startup lifetime from zero to exit is getting longer and longer, which inevitably leads to liquidity pressure from all fronts—early investors seeking some cash to reinvest back into other great startups, founders trying to balance their wealth and not have 99.9% in one asset, and employees who want to see some cash after many hardworking years. If we can even slightly take away the pressure and help those people, it creates value not only for the ecosystem but also for our fund investors, who can benefit from getting into category-leading scaleups from the region with lower risk than early-stage investing has.

With your €50M Fund II targeting post-Series A companies with solid business models in the high-growth phase, what specific signals tell you a company has moved beyond early-stage risk into that “de-risked” category where secondary investments make sense?

Besides strong traction and growth, there needs to be a strong investor base on board who are similarly interested in the final exit. Ideally, we’d like to see that there are already some discussions going on about exit routes. We’re in the exit business, so we need to see that there are underlying factors that support the process moving forward.

You have investments in companies like Bolt, Oura, and Veriff. When you’re evaluating new secondary opportunities, how do you balance acquiring shares in proven winners against finding the next generation of regional champions?

We’re always on the lookout for the next breakout companies. However, we need to admit that once we’re part of the cap table and we can see the company’s performance closely, it creates comfort to double down on some of the winners in the portfolio. On the other hand, this shows that we’re in it for the long run and want to be a partner for the company to provide liquidity. That’s why we made several add-on investments to some of the best companies in our portfolio (e.g., Bolt, Printify, Booksy). But from a helicopter view, this is maybe 20-30% of the total portfolio, so we need to have a wide range of great companies in order to invest again in the best ones.

The secondary market has been reaching record volumes globally, yet Europe remains underserviced compared to other regions. As someone building secondary infrastructure specifically in CEE/Nordics, what unique advantages do you see in these regional ecosystems that larger global funds might be overlooking?

When we launched our fund almost five years ago, there was quite a low understanding of the meaning of “secondary transaction” as such. Over the years, we’ve managed to educate the market, raise awareness about the options available, etc. This has built trust, and this is something that’s essential in making secondary transactions happen. Being local, with a good reputation and a flexible approach, helps us create those leads for ourselves that don’t come to large international funds’ tables. In many cases where we’ve done our deals, these have been the first-ever transactions in the company.

Secondary market pricing can be complex and opaque. How do you navigate valuation discussions with sellers, especially when dealing with high-growth but still-private CEE/Nordic companies where comparable transactions may be limited?

That’s a topic where we could spend hours 🙂 A typical question I have is “what is the discount in the secondary market,” and it makes me laugh, as the problem is that it’s such a complex topic that you cannot just summarize it with one average number. We’ve done deals from 0% to -52% discount to the last round—pick your number. In reality, you need to look at the specific context of the company: when was the last round raised, how has the company performed since then, what is the share class structure, which shares are we buying, what are the buy/sell dynamics in the company, etc. We try to be fair in our pricing and explain transparently why we offer a certain price to the seller. I think having such an open dialogue creates possibilities for reaching common ground and closing the deal.

Finally, for founders and investors who will be at How to Web, what’s the most important piece of advice you’d give them? We’d love to have you connect with our community. So, how can people reach out to continue the conversation with you after the conference?

Come and talk to us at the conference. It takes time to build trust and relationships. So, having early conversations even before there’s an actual potential business case on the table will help facilitate a potential deal in the future. Whether you’re the founder of a scaleup who wants to educate yourself or a private investor seeking the opportunities that secondaries might bring along, I’m happy to engage with both sides.

Don’t miss the chance to connect with Rando Rannus at How to Web Conference 2025. 

The secondary market represents one of the most significant opportunities in European tech today, creating essential liquidity infrastructure while providing investors access to proven winners at attractive valuations. As Rando demonstrates through Siena’s approach, success in this space requires deep regional expertise, strong relationships, and a patient, risk-conscious investment philosophy. The combination of longer startup lifecycles, increasing exit complexity, and maturing regional ecosystems creates unprecedented opportunities for those who understand how to navigate this evolving landscape.

See you at How to Web Conference 2025

Whether you’re a founder thinking strategically about liquidity options, an investor exploring secondary opportunities, or simply curious about the future of European startup infrastructure, Rando’s insights could reshape how you think about building and scaling in today’s market. As he says, “It takes time to build trust and relationships”—start that conversation in person, at How to Web Conference 2025, and discover how secondary markets might play a role in your startup journey.