What Founders Get Wrong Early (and It’s Not the Product)
I’ve worked in Big Law, at a public company, and now as outside GC to startups.
The biggest mistakes I see founders make aren’t about product—they’re about everything around it.
Launching too soon.
In many cases, years—if not months—have gone into your MVP, your prototype, your service offering. You’re close. Really close.
You know you should launch quietly. Test. Iterate.
But you don’t.
You go big. You leverage your network, spend on marketing, and push it out into the world.
Too early.
This isn’t a product issue—it’s a judgment call.
Do customers come back to something that’s “almost there”? No. There’s too much competition.
When you think you’re ready—wait. Iterate again. Then launch.
Picking the wrong co-founder.
A co-founder relationship rarely works when it’s transactional.
You have to be able to actually work together—and that usually means:
you respect how the other person operates,
you can get through hard conversations without things breaking down, and
you’re aligned on why you’re building this (not just a half-baked idea over cocktails).
If something feels off about 1, 2, or 3, it’s not going to work. Save your energy.
Founder bottleneck.
At the beginning, you do everything. You have ChatGPT. You think you’re unstoppable. That works until it doesn’t.
When everything has to run through you—legal, finance, hiring, product—things start to slip. Decisions don’t get made. Candidates lose interest. Contracts sit. You stop focusing on what actually matters.
There are only so many hours in the day.
Build support before you hit that wall. Start with contractors—you don’t need full-time hires yet. Keep it flexible so you can scale up or down.
You’ll move faster and make better decisions.
Having the wrong equity split with the right co-founder.
The founder equity split calculators online are complete bullsh*t.
You cannot reduce something this personal to a formula.
The right split depends entirely on the people involved and what feels fair to them. In my experience, the best splits are the ones where neither side feels entirely comfortable.
If you feel really good about the split, you probably gave away too little or took too much. That imbalance shows up later—through resentment, reduced effort, or constant friction.
It doesn’t stay hidden.
Skimping on legal documentation.
No founder loves legal documentation or legal bills.
And if you have a good lawyer, both should be kept to a minimum. But this is not where you cut corners.
You need to make sure you’ve actually issued yourself stock (if you’re a corporation). You need clean founder documentation, IP agreements, NDAs, and basic commercial agreements in place.
You’re building something. You have to protect it—even when it’s early.
One example–
A company brought on an early consultant to write code. Nothing was signed. A year later, he’s terminated and claims the code belongs to him—and tries to force the company to buy or license it.
We got it resolved, but not without using leverage we would’ve preferred to keep.
Another example–
A company incorporated early—but never actually issued stock to the founders.
A year later, the business has real traction and is worth significantly more than when they started. They go to clean things up and finally issue equity.
Now the valuation is higher, the tax implications are different, and the 83(b) election doesn’t have the same effect it would have had on day one.
What should have been a 30-minute task at formation turned into a much more complicated (and expensive) fix later.
Again—entirely avoidable.
None of this is complicated.
But it does require being intentional early—before things get messy.
And if you’re not sure you’ve gotten these pieces right, it’s a lot easier (and cheaper) to fix them now than later.
I spend a lot of my time helping founders clean this up after the fact. It’s a much better conversation when we catch it early.