Raising venture capital is often treated as a milestone. A round closes, money hits the bank, and the company moves on.
What that framing misses is the real decision founders are making.
You are not just choosing capital. You are choosing long-term partners. And once they are on your cap table, they are there for the duration. In practice, it is often easier to get out of a marriage than out of a venture relationship.
That permanence deserves more attention than it usually gets.
You can’t fire your investors
There is a simple truth in venture that rarely gets stated clearly. You can’t fire your investors.
You can replace an executive. You can pivot the product. You can even change the entire strategy. But once an investor is in, they stay. Their ownership, voting rights, and influence do not expire when things get hard.
Part of the reason founders underestimate this is the environment in which they meet investors. Fundraising rewards optimism. Founders present clean narratives and confident plans. Investors present themselves as supportive, aligned, and easy to work with.
Before the money moves, everyone is selling.
That does not mean anyone is being dishonest. It means early conversations are optimized for agreement, not for revealing how people behave once pressure replaces optimism.
To balance the investor view, it helps to hear from someone who has lived through these dynamics from the founder seat. Pekka Koskinen, serial entrepreneur and co-founder of Leadfeeder and Cluby, has worked with multiple early-stage investors over the years.
As Pekka puts it:
“When everything is going well, relationships don’t matter that much. It’s only when things go badly that you see what kind of relationship you actually have.”
That is the point where fundraising ends and the real relationship begins.
Compatibility is not chemistry
When founders talk about investor fit, they often mean chemistry. Did the conversation flow? Did the investor seem sharp? Did it feel like someone they could imagine working with?
Chemistry matters, but it is a weak filter on its own.
Real compatibility is about predictability under stress. It shows up in how decisions get made once the deck no longer matches reality, timelines slip, and tradeoffs become uncomfortable.
From the founder's side, this might become clear very quickly. At one point, an external platform dependency Leadfeeder relied on stopped working overnight, putting a core part of the product at risk. There was no clean answer and no time to prepare a story.
Pekka called his investors to explain what had happened. The response was not panic or blame, and there was no attempt to take control. The focus was simply on fixing the problem and supporting the team in any way they can.
That reaction built trust immediately. Not because the investors had a solution, but because they stayed calm and constructive when it mattered.
In Pekka’s opinion, what really matters is whether you want to call that person when things go badly, or whether you hesitate.
Compatibility is not about agreeing on everything. It is about whether you can work through disagreement without losing trust, clarity, or momentum.
When things are going well, investor relationships fade into the background. When they are not, they become central. And you learn very quickly who you can be honest with and who you cannot.
What compatibility really consists of
Like mentioned earlier, compatibility is often mistaken for personality fit. In reality, it tends to come down to three deeper layers that only really show themselves over time.
The first is incentives. Your timeline and goals need to align reasonably well with the fund behind the money. A founder building patiently will feel friction if their investors are quietly optimizing for speed, even if that difference is never stated explicitly.
The second is behavior. How does the investor respond when reality underperforms the plan? Do they default to pressure and control, or to problem solving and support when things get uncomfortable?
The third is values. When tradeoffs are unavoidable, what actually gets prioritized? Company health or short-term narrative. Founder trust or external signaling?
From the founder's side, these layers rarely show up as open disagreement. Pekka’s experience is that misalignment more often feels like a slow drift in expectations. You may not need a detailed exit plan early on, but you do need alignment on what kind of company you are building and how patient the journey is expected to be. When those expectations differ, founders feel it later as pressure rather than conversation.
You’re not partnering with one person
When founders choose an investor, they naturally focus on the person in the room. That makes sense. This is who you talk to, who joins your board, and who feels accountable day to day.
But that person is only part of the picture.
Behind every partner sits a fund, and behind every fund sits a firm. Each layer shapes your company in different ways.
The fund shapes pressure and expectations. Funds have timelines, and those timelines affect behavior. Earlier in a fund, there is usually more patience for iteration. Later on, priorities shift. Liquidity matters more. Founders feel this not through explicit demands, but through what gets supported and how much patience exists when growth slows.
The firm shapes behavior when things get uncomfortable. Firm culture determines how decisions are made when targets are missed or extra capital is needed. Some firms rely on individual conviction. Others default to consensus and portfolio-level risk management.
This is why partner diligence alone is not enough. You are not just choosing who you like working with. You are choosing a system of incentives and decision-making that will stay with you long after the round closes.
How to read the signals before you sign
During fundraising, most investors will say the right things. That is not a red flag. It is the nature of the process.
The only way to assess compatibility is to look past intent and focus on behavior.
One of the clearest signals is how investors actually think out loud once the deck is done.
As Pekka puts it:
“You learn a lot from the questions VCs ask. What they focus on, what they ignore, and how deep they can actually go. That already tells you a lot about how they think about the business.”
Another common mistake is optimizing for valuation alone. Terms matter. Valuation matters. But focusing only on price while ignoring relationship dynamics is short-term thinking in a long-term partnership.
Pekka adds an important founder counterpoint here. In his experience, the best terms usually came from the investors who were the most genuinely excited and felt like the best fit. Strong alignment often makes negotiation easier, not harder. When both sides want the partnership to work, terms tend to follow.
Founders also tend to rely too heavily on gut feel from early conversations. Good meetings are easy when everything is hypothetical. That comfort is rarely tested until later.
This is why backchanneling matters. Talk to founders the investor backed who struggled, not just the ones who succeeded. Do not rely only on references offered by the investor.
It also helps to ask uncomfortable questions directly. What happens if targets are missed for two quarters? What happens if a bridge is needed? These are not trick questions. They surface expectations early.
Pay attention during negotiation as well. How an investor behaves when there is tension over terms is often how they will behave in the boardroom later.
Most mistakes here do not come from bad intent. They come from reading the wrong signals too early, and missing the ones that matter later.
A reality check for first-time founders
Not every founder has the luxury of multiple term sheets, though.
Sometimes the choice is imperfect capital or no capital at all. That is a real situation, and it should not be ignored.
Even then, diligence still matters. Knowing what you are trading off is better than pretending it does not matter.
Founder–VC compatibility is not about finding a perfect match. It is about avoiding avoidable disasters.
What this really comes down to
Choosing investors is not about finding people you like or avoiding disagreement. It is about understanding the relationship you are stepping into, and the system of incentives that comes with it.
If you strip everything back, founder–VC compatibility comes down to a few fundamentals:
- You can’t undo the decision, because while products, markets, and teams change over time, investors remain on the cap table for the full journey.
- Fundraising hides reality, since early conversations are optimized for optimism and alignment rather than for showing how people behave once pressure sets in.
- Misaligned incentives usually show up as pressure rather than conflict, with expectations surfacing later as push instead of explicit disagreement.
- You are choosing a system, not just a person, because the fund’s timeline and the firm’s default behavior matter as much as the individual partner.
- Trust reveals itself when things go wrong, and good investors tend to ask questions, offer perspective, and let founders do the job instead of trying to run the company.
When founder–VC relationships work, they tend to fade into the background. When they don’t, they quietly drain time, energy, and focus away from building.
The most important decision is not whether you can close the round. It is whether you can live with the partnership that follows.
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