April 15th | Three-Year Review

I was driving from Milwaukee to Green Bay and it dawned on me that 4/15/22 marked my three-year anniversary with TitletownTech and my entrance into the venture capital space. I was appreciating the rolling landscape Wisconsin provides and found myself reflecting on how much the VC space and our firm had changed. But, more importantly, I realized how much my role in venture capital had changed me. Here are eight key takeaways from my drive north:

1. FOUNDERS ARE COURAGEOUS: My admiration for “the doers” has grown. I often find myself with goosebumps listening to founders explain problems and detail their solutions. There’s a certain level of courage required to obsess over an issue day and night, only to be told no. But founders wake up every day and put their energy, time and resources into solving the world’s problems. Two years ago, one of my fellow TitletownTech founders left our partner group to start a company called Demiplane with his childhood friend. That alone was impressive. The most amazing part was he decided to take the leap a week after the world shut down due to COVID-19. Now, that’s courage.

2. FAILURE ISN’T FAILURE: We are often crippled by a fear of failure, but not in the world of VC. This space is about adaptability and exploration. When you explore novel ideas, you are going to make mistakes, AND you may even fall flat on your face. But even in those moments, the grit it takes to get back on your feet leads to a growth opportunity, and, one could argue, learning from a mistake doesn’t mean you failed. The failure would be never taking the risk in the first place. We need more failures.

3. REPRESENTATION MATTERS: The statistics continue to show that companies and funds with diverse teams out-perform those that don’t. One of the responsibilities as a steward in the VC space is to be a conduit. I will never feel like I have done enough.

4. WISCONSIN IS IN GREAT HANDS: I look at some of the partners in our state and get excited. Whether it is the work Dana Guthrie is doing, or the connections Dave Sasches build to help connect the ecosystem, and all the founders who are tackling Horizon 3 and 4 level issues in our great state; I am fortunate to be able to share the landscape with them.

5. COMPETITION: This space is hyper competitive. When we started in July of 2019, deals would take 2-3 months to get inked. Now, most early-stage deals are turning around in six weeks or less. There is more capital to be deployed and as such, founders have options.

6. GENIUS IS EVERYWHERE: If you don’t open your eyes, you are probably missing out.

7. FUEL: The most competitive people I’ve met never needed any additional fuel to pursue greatness; the primary source of their energy comes from within! It was the daily grind of being the best version of themselves in their roles that pushed them forward. Don’t get it wrong though, doubters or haters usually helped them have stretches of flawlessness. Trust me, I still haven’t forgotten the people who said TitletownTech wouldn’t be successful or that my inexperience in VC would be a hinderance.

8. KEEP THE MAIN THING, THE MAIN THING: One of my favorite quotes is attributed to LeBron James. He told Lonzo Ball, a rookie, that he needed to “keep the main thing, the main thing.” Venture capital can pull you in various directions and the additional attention surrounding the space can create undue distractions. There is strength in not allowing other’s intentions deter you from the path of the goals you have set for yourself. The hype is usually temporary. One of my favorite mentors asks people if they want to do something or be something. Jokingly I answer, yes. But, if you focus on doing something meaningful, you will create value, which will bring the glory you deserve. What is your main thing?