What I Wish I Knew Before Starting a Business with a Friend

In January of 2021, a good friend sat across from me and pitched an idea. He had been thinking about it for a while. I had been thinking about something similar. The timing felt right. The opportunity was real. And we trusted each other — which felt like the most important thing.

Five years later, Threefold Solutions is still here, and so is the friendship. I am glad for both. But if I could go back and hand myself a one-page document before we shook hands, it would look very different from anything I was given. Most of the advice I got before starting was either too vague to be useful or came from people who had never actually done it.

So here is what I actually wish I had known.

The friendship is a feature, not a guarantee

Everyone around you will warn you that going into business with a friend is dangerous. That you will ruin the relationship. That money changes people. They are not wrong, exactly, but they are also not helping you. The friendship is not the problem. The absence of hard conversations before the friendship gets tested is the problem.

The best thing my co-founder and I had going for us was that we had already disagreed about things that mattered and survived. We knew how to tell each other the truth. That is the ingredient most people don't check for before they sign an LLC operating agreement.

The question isn't "do I trust this person?" You obviously do — that's why you're considering starting a company with them. The question is: have you ever had a real disagreement with this person, and did you both come out of it intact? If you haven't, you're about to find out.

Talk about money before you start — in uncomfortable detail

Not "we'll split it evenly." That's not a conversation. The conversation is:

• What does each of us think we're worth, and why?
• What happens if one of us needs to step back for a season?
• What happens if one of us wants out?
• What does "success" look like, and at what point would either of us consider selling?
• Are we building to run this thing forever, or building toward an exit?

None of these are comfortable questions to ask someone you like. They feel transactional when the mood is optimistic. Ask them anyway. If you can't have these conversations before you start, you won't be able to have them when the stakes are higher.

function evaluateCoFounderFit(person1, person2) {
  const sharedValues = person1.values.filter((v) =>
    person2.values.includes(v)
  )

  const complementarySkills =
    person1.strengths.filter((s) => !person2.strengths.includes(s)).length > 0

  const canHaveHardConversations =
    person1.conflictHistory.with(person2).outcome === 'intact'

  const alignedOnExit =
    person1.exitStrategy.type === person2.exitStrategy.type

  return {
    compatible: sharedValues.length >= 3 && complementarySkills,
    readyToStart:
      canHaveHardConversations && alignedOnExit,
    warningFlags: {
      noHardConversationsYet: !canHaveHardConversations,
      differentExitExpectations: !alignedOnExit,
    },
  }
}

Define roles early, even when it feels unnecessary

When you start, everything is shared because everything is small. You both answer every email, attend every call, figure out every problem together. That phase doesn't last, and when it ends, the ambiguity that felt fine becomes friction.

The question to answer early is not "what do we each do?" It's "when we disagree on direction, whose call is it?" You need a decision-making structure before you need to make a hard decision. By the time the hard decision shows up, it's too late to design the structure without it feeling personal.

We had to work some of this out the hard way. Not dramatically — we didn't have a blowup or a breakup. But there were conversations we had at month eighteen that would have been a lot easier at month one.

The business will reveal things

Starting a company with someone is an accelerated version of knowing them. Stress, money pressure, difficult clients, slow months — all of it surfaces things about both of you that normal life keeps politely hidden. You'll find out how your co-founder responds when a deal falls apart. They'll find out how you respond when a client is wrong and wants a refund anyway.

This is not a reason not to do it. It's a reason to be honest with yourself about what you're getting into. If you've never seen your business partner under real pressure, you don't fully know them yet. The business will take care of that.

What actually makes it work

Five years in, here's my honest answer: shared values, different skills, and the willingness to have the uncomfortable conversation before it becomes the unavoidable one.

My co-founder and I are genuinely different people. We think differently, we lead differently, we approach problems from different angles. For a while I thought that was a liability. I've come to understand it's the thing that makes us useful to each other and to our clients.

The friendship didn't survive because we were careful. It survived because we were honest — with each other and about the business. Some of the best conversations we've had started with one of us saying something that was hard to say.

That's not a technique. It's just what it looks like when it works.

If you're sitting across from your version of that conversation right now, I'm not going to tell you not to do it. I'm going to tell you to have every awkward conversation you've been avoiding first, and then decide. The business will be fine. The question is whether you've built something underneath it that can hold weight.

Start there.