The Decision to Start a Company

Photo by Jeffrey Grospe on Unsplash

For my next chapter, I’m incredibly excited to announce that I’m co-founding a company. I wanted to share my thought process in the hope that it may be helpful some day to anyone who finds themselves in a similar position to where I was.

In late Summer, I began to consider starting a company. The thought of it actually was equal parts exciting and terrifying. However, as the weeks progressed since that initial thought, I eventually became more sure than ever that the founder route was perfect for me. Here are the main actions and frameworks that drove me to a decision.

1. Socialize your thinking

I spoke to as many people as possible in the startup ecosystem, including a ton of founders and VCs. This process helped me pick up various perspectives around the pros/cons of choosing this type of career path and helped me refine my thinking. After every conversation, I found myself leaning just a little bit more toward entrepreneurship.

2. Be self-aware

Be brutally honest about your own psychology and whether you are prepared to handle the mental challenges of entrepreneurship. From a pure expected returns standpoint, founding a company is never a rational decision (especially if your opportunity cost is high). You must be comfortable with a high amount of risk and have the mental strength to navigate the inevitable roller coaster that comes with company building. If dealing with extreme ambiguity is not your forte and the thought of potentially failing makes your bones rattle, entrepreneurship might not be for you (and that’s ok!).

3. Use the regret-minimization framework

I imagined myself in my 70s or 80s and asked my hypothetical older self one question: “Do you regret never starting your own company?” I knew without a doubt that the answer would be a resounding yes. If you believe you’d find yourself with the same answer, know that no amount of money could bring you back in time to redo your career choices. With this realization, I was one step closer toward becoming a founder.

4. Be clear about what the worst-case scenario would be

When taking a big risk it’s always good to think about what the worst case scenario is and if you could live with that. For me, it would be my company failing (which is of course, terrible), but then I’d just find a job and resume my career. Not necessarily a life or death scenario, right? This thought process slowly but surely helped me minimize the feeling of terror I initially felt when I started to seriously consider becoming a founder.

5. Set a deadline to make a decision

I decided that while I wanted to carefully think through this decision, that I would set a deadline by which I would arrive at a final decision. At the latest, I would decide by Thanksgiving (but was aiming for sooner). I think it’s important to have a deadline as a forcing function for you to continue making progress and driving toward a decision.

After about a month and a half of running this process, I knew what direction I had to take. In my heart I knew that I had to start a company and no other career path made sense for me given where I’m at with my life and what I truly want to get out of life. I had previously felt the urge to start a company a couple years back, but this time I could no longer ignore what my heart was telling me.

While that process has concluded, I am beyond excited to start what will likely be the most exciting chapter in my life. I am more motivated than ever and relish the massive challenges that building a company will bring. More details to come soon!

On a final note, I realize now more than ever what a privileged position it is to be able to take a big swing like this and bet on oneself. I’m fortunate that my life circumstances allow me to pursue self-actualization, and that so many people just cannot afford to do so because of financial constraints, family circumstances, etc. I hope to pay it forward and help founders and founders-to-be in whichever way I can. Feel free to drop me a line at chrismathewcollins [at] if I can be of help.

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