I see a lot of fundraising advice focused on one thing: getting investors to say yes. I decided to look at it from a different angle: how do startups decide which investor they want?
This decision matters more than it seems at the start. A VC relationship lasts 5-10 years. Your investor will influence your next round, access to your financials, and a seat at the table when things get difficult. Picking wrong costs more than not raising.
I interviewed 14 early-stage founders across Lithuania, Latvia, and Estonia who together raised 13.6 million euros in 2025. I asked them what they did: how they found, evaluated, and chose their investors, the process, not the polished retrospective.
This is what I learned: 👇
Step 1: Build your list through people, not research
Your instinct might be to open Crunchbase, filter by stage and geography, and build a spreadsheet. That is fine as a starting point. But the investors who mattered most almost always came through personal connections.
The pattern was consistent: a founder mentioned a fund, an introduction followed, and the right person pointed you in the right direction. That warm lead, not the cold inbound from a fund’s website, is what actually converts.
“Mostly through warm contacts and the ecosystem… people who know what I’m building tell me ‘you should talk to this fund.'” (pre-seed, €500K raised)
“The main thing is to have at least a few investors who are interested so they start recommending you… without introductions it’s very hard to even get a call.” (pre-seed, €175K raised)
LinkedIn is useful too, but use it to evaluate the partner, not the fund. You are going to work with a specific person. Their background, what they post, how they think: that is what you are assessing.
Conferences are worth attending, but not for the main stage. The dinners, the side conversations, the introductions that happen in the hallway: that is where the useful connections start. Go with a short list of people you want to meet and fill your calendar before you arrive.
If your ecosystem relationships are thin before you start raising, the process will be harder than it looks. The best use of the six months before your round is not refining your deck. It is being in rooms where other founders and investors can get to know you.
Step 2: Do due diligence on every fund
Once a fund is on your shortlist, treat it the way a good investor would treat your startup: check whether what they claim matches what they have actually done.
Start with the portfolio. Look at who they have backed, at what stage, in what sectors. Check whether the deals match the thesis they describe to founders.
“…I look at the portfolio… drop the portfolio page into ChatGPT to see which companies are actually strong.” (pre-seed, €350K raised)
Then go further: reach out to three to five portfolio founders directly and ask them what the relationship is actually like.
“I open their portfolio and ping 3-5 portfolio companies.” (pre-seed, €200K raised)
If you had to take one single thing from this article, it would be this. A private conversation with a founder eighteen months into their relationship with an investor will tell you more than anything on the fund’s website.
“When portfolio companies tell you the fund was actually helpful… that is the strongest trust signal.” (pre-seed, €500K raised)
Don’t rely on media coverage. Founders almost unanimously ignored it. Don’t rely on testimonials on the website. They are arranged, and everyone knows it.
“I barely ever look at media coverage because I know how those announcements are made.” (seed, €1M raised)
What you want is unfiltered, direct feedback from people who have already made the same decision you are about to make.
One more thing: ask about terms and process early. Ticket size, stage criteria, timeline from first call to decision. A fund that cannot answer these clearly is wasting your time. A fund that answers them upfront, without being asked, is already signaling something about how they operate.
Step 3: Take the chemistry question seriously
When you have a shortlist and you are deciding between options, the factor that will matter most is not the one that shows up in term sheets.
The founders I spoke to who made decisions they were happy with, across the board, described choosing the investor they most wanted to work with, not the highest valuation or the best-known brand. The founders who had regrets described the opposite.
“You want to make sure they don’t annoy you… I don’t want to work with someone I can’t stand being around.” (seed, €4M raised)
A VC relationship is long, the dynamics are asymmetric, and trust is the currency that holds it together when things get hard. Choosing who you want in the room during a crisis is the most practical decision you can make.
“…the personality of the investment manager, I onboarded only those I felt I could work with daily.” (pre-seed, €900K raised)
Test this in the process itself. How do they engage with your thinking? Do they push back intelligently or just validate? Do they ask questions that reveal genuine understanding of your market?
Several founders described a short set of questions that helped them quickly understand whether an investor was genuinely useful or just claiming to be. These are questions to ask the VC, and each one tells you something specific:
- Can you walk me through the last time you helped a portfolio company find a key hire or customer? What did you actually do?
- What happens when a company in your portfolio misses its targets two quarters in a row? Walk me through how that conversation goes.
- How often do you typically speak with founders between board meetings, and who usually initiates it?
And probe smart money claims specifically. Ask: what have you done for a company in my sector at my stage? Not in general, give me an example. The answer will tell you whether the value-add is real or a talking point.
“We have seen many VCs say they help with hiring or fundraising but in practice they do not.” (seed, €1.8M raised)
Step 4: The questions to ask before you sign
Most founders spend the negotiation focused on valuation and dilution. The questions that will shape your day-to-day relationship are ones that rarely get asked, not because founders forget, but because nobody told them these were the right questions. They come from what the founders I interviewed found most valuable, in hindsight, having lived through it. From a VC’s perspective, a founder who asks them signals maturity and clear thinking.
Ask what communication looks like post-investment.
- How often do they expect to hear from you?
- In what format?
- What does a typical check-in look like?
An investor with clear, reasonable expectations here is a good sign. Vagueness here usually means vagueness later. The gap between what is promised in the pitch and what happens after closing is one of the most consistent sources of frustration the founders I interviewed described.
Ask how they behave when things go wrong. A bad quarter, a missed target, a pivot. The best relationships founders described had one thing in common: the investor was the same person before and after the deal closed. The ones with regrets described the opposite.
“I also filter out funds that are known to be non neutral or difficult.” (seed, €1M raised)
If you only ask one question, make it this one. Check for consistency, not by asking the investor directly, but through references. Talk to founders the investor backed eighteen months ago, during a difficult quarter. Ask whether the investor showed up the same way they did before the deal closed. More than any other signal, this one tells you who you are actually getting.
Raising is hard enough. The round itself will consume most of your attention: the pitch, the diligence, the term sheets. But the quality of your cap table compounds. The investor you bring in now will be part of the most consequential decisions you face for years, across highs and down rounds alike.
The founders who described their investors as genuinely valuable all had something in common:
- They had treated selection with the same rigour they applied to everything else;
- They had checked references, had real conversations;
- They had paid attention to what they felt, not just what they read.
The time to ask these questions is before you sign. After that, you are working with whoever is on your cap table.
👉 FIRSTPICK invests in pre-seed and seed-stage startups across Lithuania, Latvia, and Estonia. If you’re currently fundraising or about to start, check out our website or apply here.