TLDR: Being a solo founder is tough. Find a community.
It’s tough being a solo founder. Ironically, for my introverted self, the most obvious drawback: working long hours alone, isn’t really a problem at all. The ‘slow’ days, those where I’m sitting coding the next feature, fixing a bug, or just making something marginally better, where (on good whether days) I’m getting to each lunch outside with a book and take a walk around 3pm to clear my head and get some energy, may be my favorite days of all. Don’t get me wrong, I love being with and working with my customers; I can’t count the number of times I’ve walked away from an interaction with a list of ideas that excite me about the possibilities of making things that much better; my dream list far exceeds my current capacity.
The hardest part for me at least, is that without someone working with you, it’s harder to weather the inevitable headwinds you face.
In my previous startup, my cofounder Matt was my release valve. We’d regularly sit down for a beer after work and go over our progress (or lack thereof). Having someone to say out loud “F*** that guy!”. While we may not have (completely) meant it, having someone else on the rollercoaster of emotional ups and downs was a great way to lessen their impact.
Even then though, our meetings were maybe once every 2-3 weeks. That week where no one is using the site and you start panicking to figure out why? When you’re alone, that’s when your deep dark voice inside starts finding you, telling you you’re on the wrong track, that all those hours you’ve spent are wasted, that you’re going nowhere.
In college I was a music composition major, but everyone had to have ‘an instrument’. Since I sucked at piano, mine was voice; I was a decent Irish tenor. I also had a significant amount of stage fright and can still get very nervous to this day on stage, I just handle it a lot better! I loved doing duets though. Something about sharing that spotlight on stage, reacting to their energy, and being able to think about their state, instead of just the audience’s, made the performance easier and as a result made my performance better.
Of course the few weeks working with someone on a duet pales in comparison to the multi-year commitment of a cofounder. Sherry Walling of Zenfounder does a much better job talking about this and just sent out a newsletter on the subject as well, so go subscribe to her for details.
After careful consideration, I started with a cofounder for GovPossible. However, his full-time job meant he was doing largely nights and weekend work, which was a strain on his family, so he eventually backed out. Since we had a founders agreement and it was a mutual decision, it was a painless process and we’re still friends, but that still left a void for me. I’ve tried to fill that void in a couple of ways:
Life Partner: Frankly with my first startup I tried to largely shield my wife from all the stress I was feeling around the business. I instead displaced what should have been more open communication to my cofounder and kept the rest to myself. I was always afraid that laying that stress on her may negatively impact her emotionally and also make her a detractor of the business. This time around I’ve worked to be more open without how I’m feeling and how things are going. I talked through the whole decision making process about whether to try something again with her. In turn, I now have a spouse that is more supportive. I still don’t share all the ups and downs; she’s my spouse, not my emotional dumping ground, and I need to leave her space for her own emotions to share with me. Still, being more open about the process means I don’t have to feel like I need to mark my emotional state at home, which is healthier for me and more authentic for the family.
Mastermind: I’ve now been a member of two masterminds with this startup, one through Mastermind Jam and one through Microconf. I’m pretty self-driven so the accountability aspect is nice, but what I’ve found more valuable is the community. The ability to have a sounding board when needed is great, but I’ve found it to be equally cathartic in understanding that I’m not alone in problems like vendor and development management, customer acquisition, and direction. The people are also various and amazing; shoutouts to Kenton, Kane, Tammi, Joel, Rick, and the Alexes! 🙂
Local Community: If you’re lucky, you may be able to find the founder community in your area. I was fairly heavily involved in the startup community during my first startup. After several years, the community started to break up and I stopped participating. In the spring of 2021 started to work together to resuscitate the community and in October I attended the first ‘startup coffee’ meetup. After attending a few times and getting bored, I of course couldn’t resist thinking about how it could be improved, so when volunteers were requested to keep it running, I, along with Jeff Spencer and Bobby Cone raised our hands. It’s still running, now as techbeans as part of GrowCo, and we’re continuing to host and MC it with the help of the community and the new GrowCo Executive Director, Caroline Crowder. (Forgive my name-dropping in the last two bullets, but I’m truly grateful for all of them and they deserve recognition)
Maybe this is my Keynesian (Karlsian?) emotional economic theory of solo founding: Company + Family + Peers. Understanding that just one aspect isn’t all of you allows you to leverage the joy and appreciation of other aspects of your life to keep an even keel.
