How I Failed My Startup & Tactical Advice So You Don’t Fail Yours (1 of 4)

Reason #1: I didn’t prioritize seeking a co-founder

Reason #1: I didn’t prioritize seeking a co-founder

I recently failed a startup that I worked on for over a year. It wasn’t an “I raised $5M, built a team, launched a product, and got bought for less than fair market value” failure either. I failed to raise $1, failed to build a team beyond myself, and failed to launch the product.

I failed because I didn’t prioritize seeking a co-founder. It wasn’t because I was afraid of giving up control or equity. Instead, I was building this business because I believed in the mission to help people, not to Scrooge McDuck in a sea of gold.

The five terrible reasons I didn’t prioritize seeking a co-founder were:

1. Advice is always to “partner with someone you know well,” but I didn’t have a personal relationship with a single software developer before starting a software business.
2. I had a marketing background and didn’t think that any developer would be willing to partner with a “marketing guy.”
3. I didn’t believe in myself enough to convince others. I kept telling myself, “if I just build this next portion of the app, I can bring that to a potential co-founder and show her, then she’ll realize I’m legit.”
4. Because I chose to work on it full-time, I wanted someone else who did too.
5. I thought that seeking a co-founder would slow the process down.

Why I should have prioritized seeking a co-founder:

1. Accelerators and investors are far more likely to take a risk on two cheap human laborers than one.

Investors don’t say it like that, and a study showed that solo founders are more likely to succeed than co-founders, but it’s the reality for first-time founders. Founders generally take much smaller (or nonexistent) salaries than they would get on the open market, and it makes economic sense to get more cheap, talented labor than less.

Also, there’s the “key-man” risk, which is that if something happens to a solo founder or she decides to quit, as an investor, you’re completely screwed. However, if you have two founders, it’s an insurance policy.

For example, I applied to the Barclays TechStars Accelerator for fintech companies. When I had the intro call, I asked, “what do you think the biggest advantage is for founders?” The response was that the accelerator helped co-founders find out if they were a good fit and learn how to work together. The accelerator denied me for my lousy business, not because I didn’t have a co-founder. Still, I believe that that window into the accelerator vetting process was another notch in the “get a co-founder” belt.

2. I was a reckless optimist in need of a grounding force.

Nine times a day, I’ll have a “brilliant idea.” These “brilliant ideas” are often economically infeasible, physical impossibilities, or, the pitfall of all pitfalls, possible but time-consuming to achieve. Having a co-founder clarify that my most recent “brilliant idea” was a flaming trash fire in disguise would have saved countless hours.

For example, I started weekly check-in calls with another business owner, Alec Danaher of New England Wood Carving, and on average, I would spit out five ideas in a two-hour call. Alec would remind me that although some of them would meander towards the finish line, none of them drag-raced, and I needed to drag race towards a launch. He helped me keep a realistic balance between my sky-high thoughts and getting shit done. We started to record these conversations. If you have hours to dedicate to watching Alec try to straighten out my bad ideas, you’re welcome to check out some of our chats here.

3. The work would go twice as fast.

If I spent six months doing nothing but seeking a co-founder, we would have gotten as much done as I did in twelve months solo.

For example, Eitan Goldberger spent a couple of weeks collaborating on his business, Primo. Together, we built and implemented a marketing plan for his startup. There were days where I couldn’t dedicate myself to pushing the project forward, and he immediately stepped in to fill the gaps. Together, it took us less than two weeks to launch a new value proposition, design and develop a marketing website, design and implement a measurable conversion funnel, and launch converting ads. Alone, carving out that time would have taken me twice as much time.

4. I could build on the skills I had rather than becoming a jack-of-all-trades.

Instead of finding a co-founder, I decided to teach myself to code. Although I am proud to call myself a “full-stack developer” (primarily Swift, Typescript, and React), I turned into a AAA minor-league marketer with a single A-level of software development skills instead of an All-star in the big leagues-level marketer.

For example, There was a two-week span where I dug deep into Docker. That’s time I’ll never get back for marginally good Docker knowledge that I rarely use. If I spent that same two weeks focused on marketing content, we could have shown up at an investor’s doorstep with far more pre-sign-ups than I got to alone.

5. Double the connections.

When you start a business, you need to pull on every lever you’ve got. Connections are not underrated in the startup world, and partnering with a co-founder is equivalent to pressing a button to double the pool of expertise you can tactically inject into your business for free.

For example, in the brief time that I worked with Eitan, there was a time where I admitted, “I wish we could have a design pro to take a look at our web design for the new site.” Within the day, he had called his brother-in-law, a design pro, for advice.

6. Emotional support.

I consider myself emotionally resilient, but when people said that starting a company has its ups and downs, the reckless optimist in me significantly underrated the ups and downs. For each day that I believe that the startup would dramatically improve lives and our society, there was a day where I thought that I was building a useless hunk of code.

For example, just the act of talking about the business out loud with anyone helped me realign and feel confident that what I was building was important.

Tactical advice for seeking a co-founder

1. Talk about your mission with prospective co-founder(s), not your idea or vision.

I bet that there are way more people out there who share your beliefs than there are who think that your idea is brilliant. By starting with your mission, you can find common ground with potential co-founders and work together on a solution rather than an idea/worker relationship.

I started conversations the wrong way, with my idea and vision. I explained, “I’m building an app that makes it easier to save for travel.” and the worse version, “I’m building an autonomous finance application that will optimize both your financial products and how the money flows between them.”

I should have started with my mission: “I believe that travel is really important for personal and societal growth. But, we don’t invest in it the same way we invest in other things like retirement. I believe that helping more people travel more will make happier individuals and improve society. I want to build something to accomplish that.”

2. If you’ve already started, set up a check-in with another solo founder.

Chances are there’s another individual out there working on a business alone, but together you would move faster, yet neither of you is ready to give up on your ideas. First, you ignored the first tactical suggestion: be mission-driven, not idea-driven. Second, I get it; this is exactly what I did.

Propose a check-in to another solo-founder every other week to bounce ideas off each other, give each other goals, and stay accountable. It could turn into a partnership or, as my accountability buddy, Alec, and I put it, a “rent-a-cofounder.”

I met Alec on a forum called IndieHackers when I requested a user interview for people who save for travel. At the end of our user interview Alec, who owns a successful laser-wood carving business, mentioned he was looking for an accountability buddy. My initial instinct was that if there was one thing I was good at, it was working super hard on my project and that I didn’t need an accountability partner. But, I liked Alec, and I wanted to keep chatting, so I offered to be that person. The experience transformed my development by keeping me on track with specific goals and made me feel much better about the progress I was making: even if it meant staying up extra late the night before to accomplish my goal.

I whiffed on an opportunity when I met David, the founder of Redo, at a Y Combinator StartupSchool session at Harvard. We hit it off, talking about our respective businesses and beliefs until the lights in the room literally turned off on us. We share a core belief in effective altruism, and we had complementary skills but never worked together. If I were to do it again, I would have suggested a chat every other week and seen where the check-in developed. I bet that had I joined his efforts, we would be well on our way towards creating a successful business. I even emailed this to Kyle Corbitt at Y Combinator when he asked about my co-founder search in October 2020 (see the screenshot of my email below).

3. Be comfortable saying you are good at skills you are actually good at.

In my work experience, the difference between good writers and bad ones is that one says they’re a good writer, and the other says they’re a bad writer: in other words, perception of some skillsets has a lot to with how you present it. Of course, there are legitimately bad writers, I’ve seen plenty, but I’ve also seen a host of fantastic writers that, for some reason, have bucketed themselves as “poor writers.” The point is that it’s ok to say that you’re good at something to your potential co-founder. You don’t need to be cocky about it; the people you want to work with will see through B.S., but it’s ok to be comfortable saying it.

I honestly believe that I am a good marketer, but I didn’t tell anyone that because I didn’t want to sound overconfident. Sound, data-driven marketers are challenging to find for a founding team, and that’s something I severely underrated. Having launched a small software business, I can tell you firsthand that marketing and sales are more than half the battle. If you’re reading this as a skilled marketer or salesperson: the world of engineers that need a marketing/salesperson for a startup is much more extensive than you may believe.