Prologue to the Journey

Join me on my trip through the Midwest to find the next great startups being built outside of Silicon Valley.

Hello, and welcome to MidBest!

Today, we’re embarking on a five-day, six-city road trip through the Midwest. Along the way, we will be meeting with startup founders, investors, and leaders who are cultivating innovative companies in the Heartland that will shape the future of the world. Technological progress is no longer limited to a few elite coastal enclaves and has already begun to disperse. This trip aims to identify significant figures in the region’s entrepreneurial ecosystem and tell the stories of the paradigm-shifting startups they’re building.

There will be little downtime for writing during the expedition, so we’ll share a brief synopsis of the experience next Tuesday, June 29th. MidBest will then take on a weekly cadence with each post devoted to a city on the itinerary.  

On this trip, I’ll be accompanied by my good friend, Gaelen Hendrickson. He is a fellow Ohio State graduate and an incoming Columbia MBA candidate. Currently, he is interning for a venture capital firm in Vancouver, BC––but as a Cleveland native, he shares my passion for driving innovative, entrepreneurial growth in the Midwest. He’ll author and co-author some of the forthcoming posts. 

We hope you’ll follow along.

Why we’re doing this:

Four and a half years ago, I moved to Washington, DC, to pick up a member of Congress from his house every morning and deposit him home at the end of each day. I took a thirty-five percent pay cut for the privilege of becoming a glorified driver. Honestly, I was thrilled to do it. 

Eventually, I rose through the ranks and became the Congressman’s senior economic and healthcare policy advisor. I crafted legislation to improve people’s lives and did my small part to help our nation wade through the rough waters of the pandemic-recession. 

But I left DC. 

Not because I was disillusioned—I still think government can be a powerful force for good. And it wasn’t because I was unhappy—I loved my job, the city, and my friends. Instead, I left because I see opportunity: I see a technology sector that has improved by leaps and bounds over the preceding decades, with each advancement pushing the limits of human imagination and making many fabulously wealthy. But I also see a winners-take-all success structure with concentrated benefits in a few coastal enclaves, compounding the uneven recovery from the last recession.

But tech-driven success doesn’t need to be so siloed and stratified. Digital connectivity means that we can work from almost anywhere, and deals can be sealed via DocuSign rather than a handshake. The ways of the past do not foretell the ways of the future.

Already, great technology companies are growing in America’s Heartland. Duolingo, which expands access to language learning to anyone with a smartphone, is thriving in Pittsburgh, a city no longer defined by its solid steel roots. StockX, a booming streetwear and popular culture marketplace, bases its operations in Detroit, a city better known for driving on four wheels than walking in an authentic pair of Air Jordan 11s. And Olive, a company aiming to eliminate billions of dollars of waste in our healthcare system, is catalyzing change in Columbus, a city building its brand from scratch.

Venture capital is the fuel for the jet engines of these rocketship startup “unicorns.” It is the high-risk, early-stage investment that empowers entrepreneurs to scale their endeavors to global proportions. Venture funding is what helped launch companies like Google, Lyft, and Twitter to ubiquity.

Despite the midwestern success stories of Duolingo, StockX, and Olive, access to venture capital is still out of reach for most startups in the region. In 2019, VC firms invested over $60 billion—nearly two-thirds of all early-stage funding—in the Bay Area, Boston, and New York City. Comparatively, startups in the Midwest received $5.7 billion—less than 5 percent of the U.S. total.

I’d like to change that.

I believe great companies are building under the radar in “flyover country” and are being ignored merely because of where they operate. Perhaps investors are unaware of the opportunities in the Midwest, or maybe they think it’s unlikely that world-changing startups could emerge from a place so many love to deride and disregard. But the secret sauce that built Silicon Valley is not a recipe kept under lock-and-key. In fact, we have it right here in the Midwest: one part research institutions making groundbreaking discoveries, one part world-class engineering schools churning out talented workers, and a big dollop of ambitious, entrepreneurial spirit.

So, without any further ado, here is our itinerary:

The Route

Our journey begins today in Dayton. Tomorrow morning, we’ll drive up to Detroit, then over to Chicago the following day. On Thursday, we’ll swing through Indianapolis on our way to Cincinnati, and then our travels conclude in Columbus on Friday. 

These aren’t the only centers of startup activity in the region, but we’ve got limited time and a grad-student budget (don’t worry, we’ll be back!).

Thanks to the power of mRNA vaccines, we have more than thirty-five interviews packed into five days (plus fourteen hours of driving). These meetings, with folks like Ry Walker, founder of Astronomer in Cincinnati, and Jared Stasik, partner at Detroit Venture Partners, will help us paint a picture of the Midwest’s entrepreneurial ecosystem. These innovators, doers, and energizers are the foundation of their startup communities. 

If you know someone that you think would be good for us to meet, please drop a note in the comments, and we’ll be in touch!

In a nod to the region’s no-flare, blue-collar roots, we’ll be making the nearly 900-mile expedition in my 2007 Toyota Corolla. Its trusty manual transmission has more than 298,000 miles on it, and the car’s A/C conked out earlier this year, so we’ll be adding new meaning to the idea of “sweat equity.”

L to R: Gaelen, Ol’ Reliable, Will

Ultimately, this series seeks to capture the story of where the Midwest’s startup ecosystem is and where it’s going. Whether you’re a coastal citizen curious about what’s happening in the Heartland or a Midwesterner looking to learn more about what’s loading around you, I hope you find it compelling. And, please, don’t hesitate to forward this to any friends you think might be interested. We’ll write the next chapter together. 

Welcome to MidBest.