Almost finding a co-founder and why I ultimately decided to go solo

The back story

A couple months ago, I was indie hacking away on my own project when I got an opportunity for some contract work from another bootstrapped entrepreneur here in Toronto. I didn't end up taking the contract for timing reasons, but we got along quite well on our initial call and so we kept in touch.

We went for social-distanced beers in a park one night and got into a great conversation sharing a bunch of business ideas we had been sitting on. It was amazing. I get to chat with founders on twitter and in online communities but sometimes nothing beats sitting beside someone else face-to-face in a passionate conversation over a couple beers. I don't personally know a lot of entrepreneurs, and specifically the kind that are up to speed with the "company of one" / bootstrapping mindset. All this to say, it was very energizing to meet someone who had similar values around building a business.

Probably a week went by, and I couldn't get one of the ideas we had been talking about out of my head. At first, I pitched him on hacking on it for a weekend side-project, but then pretty quickly realized that I was interested in pursuing the idea further as an actual business.

We ended up deciding that we should be intentional about deciding whether or not to partner up together and not end up in a vague situation where we don't understand the equity split, roles, etc. So we went through an exercise of answering a set of co-founder fit questions.

Co-founder fit exercise

I highly recommend this exercise. The one we found was just the first result on google. It asks 34 questions to determine if you have shared values, goals for the company size, personal priorities, roles and responsibilities, equity split, etc. We both wrote down our own answers in point form on our own time, and then jumped on a call to review and discuss. This call took 5 hours. We were exhausted by the end, but this exercise was so important. It solidified many reasons we would work well together, and it also shined light on some of the reasons why we may not want to partner up.

Why we were a good fit:

  • similar beliefs around keeping costs low, keeping a small company
  • complimentary skillset (I am a developer, he is in product/design, we both enjoy marketing)
  • similar beliefs around importance of diversity, inclusion, accessibility, and other cultural values

And there were many more. To be honest there were not many red flags, but there were a few reasons why we may decide not to partner:

Why we may not be a good fit:

  • I was leaning even smaller in company size long-term (2-5 people vs 20+ people)
  • Initial disagreement on equity split
  • Individual time/effort commitment (he runs another business as well)

We managed to get over the equity split disagreement, and initially agreed that the reasons we should work together outweighed the reasons we shouldn't. It felt like 1+1 would equal 3 here. We decided that 50/50 was the way to go.

Signing the co-founder agreement ... almost

We drafted an agreement to split the shares of our not-yet-real company, and then it kind of sat there for a couple weeks with the intention of signing. At this point we had actually started working on the product a bit together, getting some designs together, making a prototype, and we kind of continued that for a couple weeks.

I actually invited him on to my podcast as a guest to talk about our decision to partner together, and this would kind of be our announcement about the decision. We recorded the episode, and then as usual, I edited it shortly after and set it to publish the next morning.

But then I had this wave of anxiety hit me pretty quickly after scheduling it. I had all these thoughts running through my head now that we were going to announce this. It was getting real. Some of the anxiety definitely came from my previous experience with co-founders. It is worth getting into that quickly.

Co-founder baggage

I had previously started a company with two other people. It was my first company and I had no idea how to go about splitting up equity. The part that was most challenging was that one person had another business on the go already. Still, I gave them a significant chunk of equity to be part of the team because they were subject matter experts. It was working well at first, but after a couple months, their other company was ramping up and ours was taking a back seat. I remember showing up to several weekly calls and being the only person there. It really sucked.

Ultimately, this unequal commitment of effort to the business led to me shutting it down. I could have probably found ways to keep it alive and go back to being solo, but by this point, I was not excited to continue based on how this experience had gone. I shut down operations, and searched for new beginnings.

The decision to go alone

I bring up that story because this time/effort-commitment situation felt like the biggest potential risk in the new company as well. My new co-founder also has another business, and it was clear that his focus would be split between two businesses. I didn't want to repeat the exact same mistakes I had made in my last business. The same mistakes that led to me shutting it down.

I unscheduled the podcast episode, and we scheduled a call to discuss some of these feelings of anxiety get his thoughts around everything. I brought up my concerns directly and we talked them out in an open and honest conversation. I actually felt quite good after this call. We really communicated well, and sometimes all you need is to feel heard. Maybe I just had a case of the metaphorical "pre-wedding jitters", I thought.

We gave it a bit of time though, and ultimately we both agreed that the time-commitment risk was real. I wanted to work towards building a company that would become my main business activity. He wanted to build this company into a portfolio of products and it was never destined to become the primary business activity. We could have seen this coming from the beginning but everything looks different through rose-colored glasses.

We toyed with the idea of a different equity split for a lower commitment of effort, but ultimately, because of our differences in long-term goals, we decided it would be best to go our own ways.

Wrapping up

This whole process took quite some time - probably a month and a half. I am very glad we didn't rush into it though. I believe these decisions should not be treated lightly. This is your life. As soon as you partner with someone else in business, this can ultimately change your entire life for years to come. In any relationship, it can be easy to get excited early on, only to have a change of heart once the initial honeymoon phase is over. We did our best to look ahead and be real with ourselves.

I want to be clear that I am not against starting a company with co-founders. I think if this particular situation had been different, had we both been able to commit similar efforts to the business long-term, this would be a different piece of writing. But this time around, the stars didn't align. In honesty, I know I am missing a lot by working on my own. It would have been great to have someone to work with on the business. These are the tradeoffs you make with these big decisions. Eventually, maybe I will be able to hire someone to help. For now, I will move alone, knowing that I have more flexibility and freedom to build a company how I would like to, at the expense of moving slower.

I hope my experience here is helpful for someone. I found it difficult to find resources on this subject. If you have any questions, don't hesitate to ask in the comments or reach out on twitter. I would love to hear about your own experience on the subject.

  1. 4

    A really great read - some of the situations mentioned really resonated for me. Anxiety is tough - hard to explain the reasons why it ebbs and flows, but damn it can keep you awake at night.

    Happy to hear you were able to work through it and have found a situation that works for you.

    Thanks for sharing! 🙌

    1. 3

      Absolutely - sometimes anxiety really does get in the way of my productivity (when I am trying to sleep for example and my mind is spinning on something). Usually I can manage it pretty well though. I think in this case it was kind of a signal that there was something that needed to change.

      Thanks for taking the time to read it!

  2. 3

    This is such a nice and insightful post. Thanks for sharing!

    Once, I tried to start a project with an older lady who had an offline educational product which she wanted to turn into a digital one. We didn’t talk much about goals and didn’t think about whether we’d be a great fit. Instead, I got right into building the app. After around two weeks of work, it became painfully obvious that we didn’t share the same vision. Yes, we quit early, but we could still have saved those two weeks of time if we had talked more from the beginning.

    1. 2

      Yes this feels a bit like my first partnership. It was with a non-technical founder who was a subject matter expert with prior founder experience. It all sounded great on paper, but in reality it just didn't work out. Two weeks is not so bad though. Good on you for knowing to pull the rip cord early.

      1. 1

        Thanks for getting back to me! Your writing is so relatable. :)

  3. 3

    Nice reading! In the past, I also started looking for a co-founder. Finally I didn't find anybody who fits me, so I am still a solo indie :-) What I want to say is that finding a missing 50% of you is very, very tough! It is about the same attidute, the same energy, the same vision, the same style of work, the same goals etc. So many points to fit together.

    Ah, I forgot - I almost found a co-founder. They guy was asking every day "How is it going?" :D Of course no value, or even a little work done. It lasted for a few month because I was just naive with waiting and thinking that the guy has to get on a correct track - never happend. At the end he asked me for money/shares because, in his opinion, he created a product which actually was mine, invented by me, and finally created by me.

    What I said was - "Tell me the actual input you have put into the product". That's was a nockout, and at the same time he understood that taking no action is equal to have nothing :-)

    If I were more clever at that point, I could say it earlier. Less stress and empty words.


    1. 3

      Ha! That was very enterprising of him but if you had no agreement and he didn't actually help, well. You did the right thing.

      In the spirit of trying to be helpful:

      • I want to click on underlined stuff on your site (like "Reporting Panel" and "24 access and live data")

      • IMO commas would make the numbers in Tests Executed, Notifications Sent, and Events Received (misspelled) stand out

      • I clicked the hamburger icon, expecting a hamburger styled menu but it wasn't

      • Hovering over the pricing link turns it dark purple which then you can't see because of the purple in the hero section

      • Personally, I think it would be more impactful to just not list the items in Basic instead of use strikethrough text but that's my personal take on it. If you're wanting all of the rows to line up, you can just re-arrange the items

      1. 1

        Wow! :-) Thanks for the feedback, really good one. 90% of the list is true, and already fixed :-). I've to find a solution for the hamburger menu, that's the thing which left to do. Once again, thank you very much.

        1. 1

          I really like the changes! Great work.

          You're very welcome.

          p.s. - I just noticed your hero section says $4 for a single URL but your pricing page says $8.

          1. 1

            Thank you! Fixed :-)
            Feel free to create an account, you take it for free.

            Once again, thanks!

            1. 1

              Why that's very kind of you and not expected. I will take you up on it!

              I'm trying to create an account for:

              [email protected]

              But it's not advancing to the next stage. Is it that I'm not allowed to use an email that's not associated with that domain?

              1. 1

                Not sure what has happend (checking now), nevertheless I created the account on behalf of you so you can enjoy the reports after a few days :-)

    2. 2

      Oh man that sounds like a tough situation. It’s amazing the entitlement that some people carry. Thanks for sharing your story as well. I’m glad you were able to move along from that.

      I agree. So many things need to align for it to be the right decision (in my opinion). I hope more people consider this before they go down the road of finding out the hard way.

  4. 2

    Great read Cam, kudos to you putting in the time and effort to make sure it was the right direction, and double kudos to you making the tough decision that it wasn't (as often its easier to just keep going!)

    1. 1

      Thank you, Chris. I really appreciate your comment. A lot of credit goes to my almost partner for taking a long hard look at the situation with me and helping come to the decision.

      And, you're right. It can be a lot easier to just keep going (in many facets of life) then you wake up one day and wonder how you got somewhere. I think intentionality is key for building a business and a lifestyle that you love.

  5. 2

    It seems worth the risk with the right person. Both of the accelerator programs I went through last year presented statistics of how many single Founder startups fail vs 2+ Founder startups and although I don't have the numbers at hand, it was telling.

    1. 1

      I agree with that for sure. I think in this case I maybe even found the right person, but we just had the wrong timing.

  6. 2

    Thanks for sharing. Probably, if I know at first I would not have lost a partners, and then did not work solo for so long.

    1. 2

      Hopefully others can take something away from it before they get to that same point that you and I have reached. Thanks for reading!

  7. 2

    Very interesting.

    'I gave them a significant chunk of equity': did you have a vesting schedule on this, out of interest? That sounds like it was a really rough experience, wonder whether vesting would have helped or not so much.

    1. 2

      So we did set up vesting for that first startup. I had the option to fire my co-founders and go at it alone, but to be honest, I just felt a lot of resentment around what had happened. I was not as excited to pursue the idea. I think I could have done that and continue to move forward with the business, but I was very deflated emotionally by that point. The business was growing but not extremely successful. Maybe I would have gone about it differently if we were in a better financial position.

  8. 2

    I've been wondering if there is some way to help founders mitigate risks involved in forming a partnership like this. Something that would enable founders to try partnerships on for size without over committing or under fulfilling. Just a seed of an idea but wonder if you have any thoughts.

    1. 1

      It's a difficult area to navigate. So much of the co-founder dance reminds me of dating / relationships, except you basically need to jump right into marriage immediately.

      I think one of the better ways to find out if you are a good fit would be to work on a side-project together first that neither of you plan to turn into a business.

      Alternatively, partner with a former co-worker where you both got along quite well.

      Even then, with both of those options, you still need to answer all these questions about your long-term goals and values, and that should narrow the options even further unless you are willing to compromise on some of your requirements.

      1. 1

        I'm thinking of some kind of incubator where founders agree to work on projects earning equity until acquired enough to take full control and spin off a separate company.

        Would avoid the need for marriage at first sight. Incubator would retain equity. Ideally would be shaped to encourage incubator to actively work with founders to get their fledgling startups established instead of the current shotgun approach shooting for unicorns.

  9. 2

    Wonderful post mortem! Thanks for sharing.

    1. 1

      Thank you for reading!

  10. 1

    Does the OP or anyone one else have further ideas of how to “evaluate” cofounders? To help future founders?

  11. 1

    Cam, this was a great piece of writing and the experience is very understandable. Kudos to this would-have-been co-founder as well for going through this in a mature and thoughtful way and for not having made it difficult for you. All the best for the business!

    1. 1

      I agree - they deserve a lot of kudos for really being thoughtful about the decision. We both took a step back and made the decision together. Thank you for reading, and for taking the time to reply :)

  12. 1

    Really liked the post. I've been kicking around the idea of bringing on someone to help build but have ran into the same concerns you had. Best of luck to you and your business!

    1. 1

      Thanks for reading, James. And wishing good luck to you as well!

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