How to Choose the Right Investors

The average marriage in the United States lasts about eight years. What most founders don’t stop to consider is that your relationship with an investor — especially one who joins your board — can last a decade or more. That’s longer than most marriages.

So here’s a question we should all consider: If we wouldn’t marry someone we barely know, why are so many of us quick to partner with investors we haven’t fully vetted?

I’ve seen too many founders raise money before they’ve fully figured out what they’re building or what kind of investor actually makes sense for the journey ahead. And when that happens, it’s not just a rough board meeting or a few tense conversations you’re up against — it’s the possibility of losing control of your company entirely.

Because the investors you bring on board don’t just fund your company. They shape your decisions, your board dynamics, and your day-to-day realities as a founder. And the quality of your relationship will either create friction or accelerate your success.

So let’s talk about what it means to be deliberate in who you bring on as an investor because not all investors are created equal. Some will help you build a thriving, enduring business. Others will make you wish you’d never taken the money.

This Isn’t Just a Deal — It’s a Relationship

At Ninety, we use the term Ideal Stakeholders with intention. These are people we believe we can build high-trust relationships with over time — the ones who align with how we think, what we value, and where we’re going. And in every healthy founder-investor relationship I’ve seen, it starts with the same foundation: character, competency, and connection.

• Character: Do they do what they say they’ll do? Do you trust what they say and believe they are being genuine and authentic? Are they transparent, consistent, and grounded in integrity, or do you suspect there are hidden agendas?
• Competency: Are they offering experience, insight, or network access that sharpens your thinking and helps you grow as a leader? Great investors bring more than money. They bring capabilities you don’t have yet.
• Connection: Do they believe in your Forever Agreements? Are you aligned on Core Values, goals, strategy, and what’s most important? Do you enjoy the conversation, or do you leave every meeting feeling like you’re in a power struggle?

When all three are in place, you’ve got a shot at building something great together. But if even one is missing, no amount of capital justifies the tradeoff. Remember that desperation leads to bad deals, and bad deals are hard to undo.

Are You Really Ready for Investors?

Let’s pause and ask a question that too many founders neglect to ask: Are you even ready for investors right now?

This isn’t about whether you’re a strong leader. It’s about clarity. If you’re still chasing product-market fit, still working out your Forever Agreements, or still unsure of your North Star, then it’s not time to raise capital.

Before you bring on outside partners, take a hard look at where you stand. Ask yourself:

• Do we have a clear vision in place?
• Do we know who our Ideal Customer is, what industry and niche we serve, and what makes our value proposition compelling?
• Is the team aligned around a consistent set of Focus Filters?
• Do we have a real strategy — not just a list of goals but a clear understanding of the kind of company we’re building?

Because when you take on investors, you’re signing up for a long-term relationship, one that could last a decade or more. And if you’re not clear from the start on who you are or where you’re going, it won’t end well.

Let’s be honest: You’re not going to attract a great investor if you’re still figuring out the basics. You need to know where you're going and how you plan to get there (and you need to be honest about what you don’t know yet).

Rushing into a relationship with investors won’t get you there faster — it just increases the chances you’ll end up with the wrong partner. Take your time. You’ll be glad you did.

What You Want (And Don’t Want) In an Investor

So how do you know when you’ve found the right investor? And, more importantly, how do you know when you haven’t?

Not every investor will be a match. That’s the point. The clearer you are about who you are, what you believe, and how you lead, the easier it becomes to attract the right people — and filter out the wrong ones fast.

When it’s right, you’ll feel it. You’ll see:

• Mutual respect for one another
• Open, honest, and efficient communication
• Alignment on your Forever Agreements, your strategy, and how you run the company

But what matters just as much (maybe more) is knowing when to walk away from a potential deal. The biggest mistakes I’ve seen founders make weren’t about the terms of the deal. They were about ignoring the warning signs. Here are a few red flags to look for when vetting potential investors:

• They don’t believe in your strategy: If they’re second-guessing your direction now, imagine what happens after they’ve got a seat on your board.
• They try to run your business: This is a power play, plain and simple. And it’s a preview of what’s coming.
• You just don’t like working with them: Maybe they’re competent. Maybe they check all the boxes on paper. But if you can’t have an open, unguarded conversation without stress or second-guessing, that’s a bad sign. Respect is table stakes.

I’ve watched founders lose their companies because they picked the wrong partner. In one case, a board member manipulated the strategy just enough to cause the founder to stumble — then used the moment to swoop in and take over. By the time the founder realized what was happening, it was too late.

Don’t say yes to just anyone. The wrong investor can cost you everything.

What Real Partnership Looks Like

Let’s say you’ve found the right investor. You’ve had the conversations. You’ve built trust. You’re officially in business together. Now comes the part that matters most — building the relationship for real.

That means communicating when things are good and when they’re not. It means owning the hard moments. When something breaks, don’t wait to reach out. Say, “Here’s what happened. We’re working through it. I’ll keep you posted.”

Those early conversations set the tone of the relationship. They either build trust or chip away at it. And if your investor hears about an issue from someone else before they hear it from you? That trust is gone.

Now keep this mind: You will inevitably hit a wall at some point. Something won’t go as planned. And in that moment, your investor will be watching — not just to see what went wrong but to see how you show up. Are you honest? Calm? Accountable? Are you asking for support or hiding the truth?

It’s in those moments that the real nature of the relationship is tested. Great investors know this. They want to see how you lead under pressure. They know that how you show up in failure is just as important as how you lead in success.

So be the kind of founder who leads with transparency. Who earns trust in every interaction. Who treats the investor relationship like what it really is: a high-trust, long-game partnership.

Because if you’ve chosen well, they’ll help you build the kind of company that can stand the test of time, and they’ll be right alongside you for the ride.

The Cost of Getting It Wrong

At the end of the day, this isn’t about money. You’re building something that matters — not just for your customers, but for your people, your community, and all your Ideal Stakeholders. The right investor helps you do that. The wrong one puts it all at risk.

So be deliberate. Lay the foundation first. Get crystal clear on your Forever Agreements before you even think about raising capital. And don’t bring anyone in who you can’t see yourself having a relationship with for the next decade.

Because if you get this wrong, it’s not just a rough quarter or a tense board meeting. It’s like a divorce, only worse. In a divorce, maybe you lose half. In this game? You could lose everything you’ve built.

Want more on this topic? Check out the episode of the Founder's Framework podcast.