Evolution of the Psychology of a Serial Entrepreneur

I caught up with a founder today who told me about his new start-up. He’s had two successful ventures already, so I was curious about his motivation for this third one. He shared that his perspective has evolved with each company:

  • Not have to work for anyone – His first company was meant to replace his job. He wanted to own all the equity and cash flow to fund his family’s lifestyle.
  • Financial independence – With his second company, he was focused on achieving financial independence. His goal was to create a scalable solution that had equity value for his investors and him. Even though he raised investor capital, he mitigated for the downside and made decisions that could be interpreted as conservative.  
  • Swing for the fences – Now, he wants to create a massive third company and is willing to take the risks necessary to make that happen. He’s got cash flow coming in from his first company that covers his family’s needs. He has a material nest egg from the sale of his second company that secures his family’s future. He’s now completely focused on the upside of this new venture, and he’s raising a significant amount of venture capital to execute his plan.

As we chatted, I shared my thoughts on psychology that I talked about in yesterday’s post. He agreed and said he was playing to not lose with his first two companies, but he’s playing to win with his latest one. As he’s gained more entrepreneurial experience and created a safety net for his family, his psychology has evolved. What terrified him in his first two ventures now excites him in his third one.

Today was a reminder that founder psychology isn’t static—it can change over time.