Why I Do Startups
An underdog story, a national championship, and the reason I chose this work
This past Saturday, college football fans got to witness perhaps the greatest Cinderella story in the history of the sport.
One of the losingest programs in major college football won the national title. To put the turnaround in perspective, Indiana Football still has the most losses of any program in major college football history and had zero double-digit-win seasons in 135 years of existence!
Unlike most title contenders who take time to build up, the Hoosiers went from nothing to something in just two seasons, after the hiring of a curmudgeon coach from lower-level James Madison University, Curt Cignetti. Not only did Cignetti bring his coaching staff with him (most of whom have been together for decades), but he also brought a ton of players from James Madison.
Experts mocked him and his players with insults ranging from “Why Indiana?” to “Those kids will not be able to compete at the higher levels.”
Now, two short years later, that same team sits atop the college football universe. So much for not being able to compete.
Watching Indiana steamroll Alabama and Oregon, and then dispatching the mighty Hurricanes, I found myself wondering why I was rooting so hard for the Hoosiers—especially since they beat my beloved Buckeyes in the Big Ten championship game.
Then, it hit me.
Why I Was Rooting for Indiana
Not only did this story unfold in the world I knew before Venture Capital—college football—but the Hoosiers’ journey encapsulates one of my life’s driving forces: being a publicly doubted underdog and emphatically proving every single doubter wrong.
The classic startup version of this challenge is the company that, after endless pitching with few investors, suddenly has a fundraising round that everyone wants to join.
For those of you who don’t know, before embracing my venture capital nerd side, I used to coach non-scholarship college football, and I loved it. I enjoyed the camaraderie, the pageantry, the thrill of victory, and the motivating drive of defeat.
I also loved being the underdog.
There’s a special feeling in knowing the other team thinks they will roll over you. Only you know you are going to give them the game of their lives—something I will never forget.
Right now, college football fans across America (Miami fans excluded) get to enjoy the same feeling as the Indiana Hoosiers.
Indiana managed to actually accomplish the overused moniker “From worst to first.”
As if that isn’t enough of an underdog tale, they are led by coach Curt Cignetti, who came from lower level James Madison. My hometown Cincinnati Bearcats allegedly refused to interview him for their head coaching job. They felt he lacked big-program experience (shakes fist at the sky).
The Question I Get Asked
Indiana’s championship run crystallized why the underdog journey resonates with me and shapes my professional path. With this in mind, I can now clearly answer a question I’m often asked:
Of course, working with startups comes with its own set of challenges (to my clients: you can laugh while reading these—there is no need to apologize):
Many problems are urgent and require immediate attention.
Clients need enough money to stay in operation while also paying for your services.
Overly eager clients may agree to something without consulting you first.
Members of the same company will fight with no formalized way to solve that argument (leaving me to play therapist).
Why I Keep Coming Back
Yet, despite all these challenges, something keeps pulling me back into startup land.
I love supporting the underdog. Backing those who other doubt gets me excited to open my laptop every day. However, I embrace the underdog role even more by representing startups and fund managers in the Midwest, an underdog region in the startup and venture capital scene.
My love of the underdog does not stem from watching too many movies with fairy-tale endings. Instead, my disability has given me the opportunity to play the underestimated underdog throughout my life.
“You’re never going to be able to walk.”
“You should stop working out so much and enjoy the wheelchair.”
“You should just be happy to get a job—perhaps a cashier is a good career for you.”
“Are you sure law school is for people like you? Don’t they have special schools?”
“How are you going to get clients if you’re in a wheelchair?”
These are just some of the common refrains I have heard throughout my days.
When I was younger, such statements got me down. Now, I meet them with an external smile and an internal smirk. It’s another chance to prove someone wrong who underestimated me.
Wear Out or Rust Out
A personal mantra guides me: “Wear Out or Rust Out.”
It reminds me to use skeptics’ doubts as motivation. You either let them lull you into non-action and rust out, or you use their doubt as fuel and keep working so that you only stop from wearing out.
I hope anyone reading this will find their own mantra. Use doubt as a stepping stone, not a stumbling block.
The Final Chapter
This opportunity to help others prove doubters wrong by supporting underestimated founders is exactly what drew me into working with startups and venture capital.
Indiana’s title journey serves as an example of what I shout from the mountaintops:
The doubters don’t get to write the final chapter.
The odds do not determine the outcome.
If you’re building something you’re passionate about, or if you’ve been told your idea won’t work, or you keep hearing that your background isn’t right, welcome to the club. You’re the underdog everyone is betting against!
Let’s Go!
That club is exactly where I want to be. Because the best stories in startup land, just like in college football, aren’t written by the powerhouses. They’re written by the people everyone underestimated who refused to believe them.