We started in 2021, working in crypto. Looking back to the time we got started, I made some serious foundational errors: - Selling 40% of the company at preseed for 1.2mln and signing a predatory shareholder agreement - Trusting a co-founder relationship which never really worked, hoping to fix it along time
But 1.2mln$ in the bank made me forget about these issues. Started to work on the business heads down.
After 18 months of iterating, things were finally moving. Our vision became clearer, and we got into a well-known accelerator. But that’s when everything started to unravel.
My relationship with my co-founder began to deteriorate rapidly. I felt like I was doing everything—closing clients, managing product, handling content, brand, fundraising—you name it.
My co-founder, on the other hand, wasn’t pulling his weight. His network and skills weren’t contributing to the startup’s success. I raised these issues multiple times, and each time he made promises that he would step up and deliver. But in reality, anything he touched would underperform.
Eventually, the investor and I decided to revoke his powers. That's when the nightmare began: a drawn-out legal battle that lasted 12 months (one third of the startup life).
My biggest mistake was not thinking long-term. I didn’t fully grasp the fact that I was locked into a relationship with this co-founder for the next 5 / 10 years, with him owning 30% of the company and having no intention of selling. His ego was bruised, and I was overly confident that I could fix everything by just working harder on the business.
That led me into a nearly unbearable situation: - I was working myself to the bone, with a very low salary - I owned less than 30% of the company. The rest of the team had little to no equity. - 70% of the company was split between an investor with no clear value-add and a co-founder ready to go to war.
On top of that, the investor still owed us money and refused to invest further. They helped me fire the co-founder, but after that, it was radio silence. I couldn’t even raise new money with this cap table. The only way out was to negotiate a deal: - The investor would give up some of their shares. - The investor would provide the promised funding. - My co-founder would sell at a reasonable price based on what we had in the bank.
But months of negotiations went nowhere. The co-founder demanded 10x what we could afford and threatened to sue the investor. The investor, on their part, refused to inject more capital into the company.
Despite all this chaos, we actually reached break-even, but the co-founder’s constant weekly threats and harassment drove me to a dark place. My stress levels became unbearable, and I lost all enthusiasm.
Eventually, I made my final offer to the co-founder: "Take $150k now, or we shut down the business." In a formal shareholder meeting, he not only rejected the offer, but called it ridiculous. That’s when I snapped. I hired a lawyer and resigned. The company shut down. 10 employees fired.
Huge. Fucking. Failure.
Now, my co-founder is suing the investor and walking away with around $100k from the settlement. Meanwhile, I walk away with nothing, except lawyer fees.
Lessons Get the foundation right. Product market fit is achievable with time and the right team. The foundation is much harder to change later.
(and product market fit is a necessary condition, but unfair advantage is where it is at)
When this happens, you have to invert the offer and say that he can pay you that amount for you to leave instead.
I proposed to give him my shares for FREE. He refused, knowing it was not capable of running the business.
On one hand, he told me the business value was in the millions. On the other, he would not buy the entire business for free.
Also, he always knew he could get some money suing the investor
It's also why I am incredibly hesitant to have a co-founder and it's why I went the bootstrapped approach instead of VC funding from the start.
My approach for the future: - Don't raise unless you really need to scale. Bootstrap as long as you can - Co-founders are ok, but with very clear pacts and shareholders agreement to manage conflicts
I was not the only one though, the investor gave us a lot of money with a very bad shareholder agreement
cofounder arguments are common, esp in crypto. for your next venture, it's better to have a cofounder agreement with vesting schedule in place. once someone becomes irrational and unreasonable, it's a sign to get lawyers involved.
dont be too hard on yourself, happens to the best of us.
Agree on the vesting. Rookie mistake. Also on the investor part - surprisingly they never asked it.
Will make sure to involve a good lawyer as soon as possible in the next venture
Granted I've only got started on this journey a few months ago, but I tried to find a co-founder and failed 3 times to find someone who I can trust and is capable. I think I'm just going to do it myself because counting on someone else at this stage while giving up significant equity to a bozo is a recipe for disaster.
It is very easy to fuck it up
I’m a swe and I’ve done everything from cleaning pantries to delivering on 100 million plus projects. So I can do anything. But I also don’t know a lot and love learning and figuring stuff out. I wish I could find someone who could compliment me well.
it's hard and brutal especially for first-time cofounders, but it's part of the process
It sucks for the time that it takes away from building a company. And it is one of the reasons I'll probably go for a standard job before starting a new one
And do you have thoughts on how next time you'd go about picking one differently?
Great question. I'll try to have a trial period on the job. Set a high bar for integrity and execution. And then legal vesting...
For what it's worth, the people I've had the most success working with are people I've already spent some time working with. But yes to those other things too.
Good investors understand the benefits of founders mental health and should not push you to work for free.
Disclaimer: I am not in a startup / tech hub. I realized that there are many more investors outside my geography. Professional investors.
Indeed I am leaving my country and starting new in another place