If I hadn't brought on a co-founder, we would have launched beta six months ago. Here's why I want(ed) a co-founder, what happened, and lessons learned.
This is a long one. TLDR; at the end.
I'd just user-tested a clickable prototype that I threw together in a few weeks using Webflow.
The demand was there, and the momentum was building. The next step was to build a functional product—auth, user dashboard, state management.
I'm a technical marketer, and I've been building websites for going on two decades, but I'd never built anything beyond very basic web apps.
I was sure I could figure it out, I just didn't know if it would take 3 months or 6 months to get there. In my mind, a more experienced dev partner would make this go faster and free me up to focus on other parts of the business.
As I was wrapping up user testing, I got introduced to the MD of a Techstar's program focused on workforce development (our category).
He liked where things were going and encouraged me to apply with the caveat that I was unlikely to get in without a co-founder. This started coming up more and more, "To be successful, you need a co-founder."
The thing is, StepLadder isn't my first startup. Everything else I've done, I've done with co-founders. And having the right co-founder is way more fun than going it alone.
In the end, it came down to:
I started having as many conversations as I could with my network. When my network was tapped out, I went digital. I posted on /r/cofounder, Slack groups, and sent InMail.
I lined up ~25 calls and spent the next few weeks in Zoom hell. I narrowed things down to three candidates, but there was one that checked more boxes than the rest.
We talked for three more weeks, and then he flew here to hang out for the weekend. Unprompted, he also set up a repo and starting building a POC.
The whole process took about a month and a half—which was a month and a half I didn't spend building or talking to potential customers.
There weren't fireworks, but we got along OK (for strangers) and decided to move forward together.
I'd ported the front-end over from Webflow to NextJS, migrated the content to Contentful, and had a good base for him to build on.
We agreed on a product roadmap to launch the beta within two months. We also agreed that speed was our strategy, and we needed to build and ship quickly.
As co-founder and CTO, he would get 40% with standard terms (one-year cliff, four-year vest). He would also continue to hold down his day job until we hit ramen profitability or received funding.
We had set a beta launch date of October 30th. Given the front-end was already built, he was confident that this was a conservative timeline that we would have no problem meeting.
To make the launch date less arbitrary, I scheduled us to pitch at a local startup event two days before launch. Even with the pressure of the hard deadline, we ended up missing the date.
In response, we scheduled three working sessions per week and pushed the timeline back to November 30th, which then turned into December 30th, then January 30th, and then…
1. This was my co-founder's first startup and he underestimated the commitment. When we initially discussed how much time he could dedicate each week, he replied, "25 hours." My response, "That's unrealistic; how about 15?"
Even at 15 hours per week, he quickly started experiencing the challenge of coding all day at his day job and then finding the motivation to keep coding nights and weekends.
2. Early tech decisions and unwillingness to pivot ground us to a halt. The initial back-end tech stack decisions quickly led to things becoming overcomplicated and overbuilt.
Rather than pivot and simplify, he kept doubling down until it became an unmanageable mess. This was really where the train went off the tracks.
3. Too much trust too early; too little verification too late. Steve Jobs is often quoted as saying, "It makes no sense to hire smart people and then tell them what to do." That's how I operate. Usually, it serves me well.
However, our relationship was too new and there weren't enough guardrails from the beginning. I wanted my co-founder to own the tech stack and feel empowered to make decisions without me getting in the middle.
Unfortunately, I let things continue to slip for too long before digging into his code and verifying things for myself.
Our first hard conversation happened at the beginning of December—three months in. Up until then, we had course correction conversations but no come-to-Jesus talks.
We agreed that things weren't going as smoothly as they should and we needed to ship faster. So we re-affirmed our commitment to launching at the end of the month, a deadline that we again missed.
Finally, after hearing for two months that we were just a week away from implementing front-end features that relied on state management, I decided to dig into the code. It was a mess.
So, I spent a weekend refactoring our entire codebase and replacing Apollo with Redux. The result was a parity build with working state management.
It was February, three months after we were supposed to launch beta—and with the previous repo, a launch date wasn't anywhere in sight.
We discussed the current state of the project and how it had become overcomplicated. I walked him through the new repo with working state management that I deployed on a different host (Vercel).
He looked at the new repo and agreed to wrap up the missing features in a week. When that day came, he hadn't made any progress.
The stress and pressure had caught up with him. He needed a break. We agreed to meet back up when he was ready.
A few weeks later, we met over beers, mutually agreed to separate, and parted on good terms.
Immediately after ending things, I felt like I got punched in the heart with a shot of adrenaline. I was now the only thing holding back the launch of our beta.
So I got to work, and for the first few weeks, I made quick work of the backlog.
I got things 95% of the way there and then ran into some bugs. In the frustration, I lost momentum. I was burnt out and decided to take a break of my own.
In that time, I had several networking calls—and received feedback like:
"StepLadder may be the coolest solution to this problem I've seen… if you can actually pull it off." and "As a hiring manager, I'm so excited for this."
Just like that, the spark was back.
It's been seven months since I fully validated the demand for StepLadder and just over a month since my co-founder and I split.
This weekend, I'm wrapping up QA and getting things ready to launch on Monday.
I absolutely believe that you don't need a co-founder to be successful, but I still want to find the right partner in the future, even after this incredibly trying experience.
There are smaller projects—like Hired Hemp—that I fully intend to bootstrap solo. But this problem is too big to take on alone.
Startups are hard, and finding a co-founder who is the right fit for your startup is even harder.
Between the search, the initial calls, the ongoing meetings, and the ramp-up period, and the split, I probably lost three months of productive time.
Had I kept my head down and not gotten distracted by the stigma of being a solo founder, I would have been able to launch our beta on my own back in October.
I still want a partner, but next time I'll take it slow and have a better process in place.
Do it for the right reasons.
The fact that 40% of my decision was influenced by peer pressure likely clouded my judgment. Don't rush and don't bring on a co-founder just because solo founders are heavily stigmatized.
You can't force chemistry.
My co-founder and I got along but there wasn't an overwhelming sense of chemistry. To be fair, we're both introverts and I take a while to warm up to people. But when things didn't start to click after a few months, I should have taken it as a sign. To make it long-term, the chemistry needs to be there.
If you're even remotely technical, learn to code.
At my first startup, we built the servers our code ran on and used early MVC frameworks. Things are way easier now—more ways to learn, more communities to support you. It only took me a month to upskill my knowledge gaps enough to finish the development solo.
Take your time and figure out smaller things to build together first.
If I had a do-over, I would have started things off with a small feature or project. This would have been enough to understand working and communication styles better, how we approach challenges and what we could actually do together.
Give people a chance, but end things quickly if you know it's not going to work.
I was ready to part ways at least a month before we finally did. Calling it quits earlier would have been better for both of us.
Hire hackers and keep it simple.
Startup dev mentality is way different than enterprise dev mentality. Make sure that whoever you bring on has a hacker mentality and is comfortable moving fast. To move fast, keep things simple.
Even if you're not technical, trust your gut. If things seem more complicated than they need to be, they probably are. Hit pause, ask questions, and regroup if necessary.
There are two sides to every story. This one is mine. Thanks for reading! I hope someone can learn from this giant wall of text (or the TLDR;).