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My cofounder is someone I had work with for six years prior to starting our company together. During that time, he was my boss for all but one year of that time

My cofounder is someone I had work with for six years prior to starting our company together. During that time, he was my boss for all but one year of that time. We both happened to leave our prior place of employment one month apart, then two months later met up again and started working on our current company. I wouldn’t do anything different in hindsight. There are so many challenges in starting a company, who you start it with should be as de-risked as possible. Even with a long working relationship, we constantly have to work on our way of working to make sure we’re balancing one another properly. Had we not come into this company with significant prebuilt trust, things could have gone off the rails at multiple points along the way. Hope that’s helpful!

lichtenberger 7y ago
That's a great insight, thank you :-)
jaredwiener 7y ago
This is great! Do you ever think about what it would be like starting solo? Or is the other person part of the de-risking?
- wjossey 7y ago
  I do think about this from time to time, and while I don’t think today I’d make a good solo founder for a “hyper growth” company, I could probably solo found a small business decently well. So, as an example, people become consultants, which is in essence a “small business”, and they don’t necessarily need a co founder to be successful. They may have trusted people they turn to for assistance, but generally speaking it’s a solo endeavor. A few months ago I spun up a “side project” that is a free mentoring service for managers (link is in my profile if that’s helpful for you!). It takes up about five hours a week, I do light promotion for it on social media and HN, but my total time commitment is fairly capped. I’m not constantly iterating on potential product angles, or spinning up different business units. It’s just me, being a good neighbor to fellow managers. Conversely, my “day job” is really complicated. It’s services and software, in a field I’m not professionally trained in (organizational development). We do B2B deals, sign multi year agreements, have to do cold outreach, spend months trying to win deals, and we’re constantly experimenting with ways to unlock revenue. If I had to own all of that, plus own the product, I’d be overwhelmed and ineffective. So, I take the product. He (my business partner) takes everything else. It allows us to carve out day to day responsibility and move forward effectively. If I had to hire for his role, I’d be searching for a unicorn. If he had to hire for my role, he’d have gotten really half assed results. For even more complex startups, I can understand why there are three or more founders. Everyone should bring something special to the table, and own a huge component of work that is critical to long term success. So, that could be a marketing wizard, an engineer, and a business developer for some cool consumer product. Hope that helps!

lichtenberger 7y ago

That's a great insight, thank you :-)

jaredwiener 7y ago

This is great! Do you ever think about what it would be like starting solo? Or is the other person part of the de-risking?

wjossey 7y ago
I do think about this from time to time, and while I don’t think today I’d make a good solo founder for a “hyper growth” company, I could probably solo found a small business decently well. So, as an example, people become consultants, which is in essence a “small business”, and they don’t necessarily need a co founder to be successful. They may have trusted people they turn to for assistance, but generally speaking it’s a solo endeavor. A few months ago I spun up a “side project” that is a free mentoring service for managers (link is in my profile if that’s helpful for you!). It takes up about five hours a week, I do light promotion for it on social media and HN, but my total time commitment is fairly capped. I’m not constantly iterating on potential product angles, or spinning up different business units. It’s just me, being a good neighbor to fellow managers. Conversely, my “day job” is really complicated. It’s services and software, in a field I’m not professionally trained in (organizational development). We do B2B deals, sign multi year agreements, have to do cold outreach, spend months trying to win deals, and we’re constantly experimenting with ways to unlock revenue. If I had to own all of that, plus own the product, I’d be overwhelmed and ineffective. So, I take the product. He (my business partner) takes everything else. It allows us to carve out day to day responsibility and move forward effectively. If I had to hire for his role, I’d be searching for a unicorn. If he had to hire for my role, he’d have gotten really half assed results. For even more complex startups, I can understand why there are three or more founders. Everyone should bring something special to the table, and own a huge component of work that is critical to long term success. So, that could be a marketing wizard, an engineer, and a business developer for some cool consumer product. Hope that helps!