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Local founders discuss how to gracefully move on from a startup


Dan Ross-Li  Charley Miller
Dan Ross-Li, the founder and CEO of Affinna, and Charley Miller, the co-founder and chief product officer, of OrgVitals pose for a photo after taking part in a panel at Venture Connectors on July 10, 2024, in Downtown Louisville.
Stephen P. Schmidt

In the startup world, baseball terminology can be abundant. Founders make a pitch. They take a swing — and more times than not — they strike out.

On Wednesday, Louisville entrepreneur and OrgVitals Founder Charley Miller offered a different take by referencing a quote from Joey Votto, the former standout of the Cincinnati Reds.

“Resilience is the sixth tool of baseball,” Miller said, quoting Votto (along with hitting, hitting with power, running, throwing and fielding).

Although, you can look at those five other tools, Miller said, resilience is unpredictable in a baseball prospect — as well as a founder.

“The same thing is true for investors looking at startups,” he said. “Resilience is the number one factor that’s going to prove if a startup is going to make it or not.”

Miller was speaking on a panel at the July edition of Venture Connectors — on the top floor of the Kentucky Science Center in Downtown Louisville — entitled: “Graceful Exits: Creative Solutions for Startup Challenges.”

He was joined on stage by Dan Ross-Li, the founder and CEO of Affinna, and Garrett French of Citation Labs, one of Affina’s and OrgVitals’ Louisville-based investors. The panel was moderated by Lisa Bajorinas, the executive director of the six Kentucky innovation hubs for the Kentucky Science and Technology Corporation (KSTC).

Since January 2023, the team at OrgVitals has been doing what Miller calls “reverse bootstrapping,” by going from “zero to one” with customer acquisition before getting other day jobs to use as leverage for the next phase.

“The goal here is to sustain ourselves so we can sustain the startup, which is still growing and being developed,” Miller said. “We still have people working on the code. Let’s get to a point where we think we give ourselves the optionality of what’s next — whether it’s ‘Do we sell it? Do we grow it, and take our investment and go to another level?’”

“If I had known he had that intention from the beginning, I would have invested more money probably, right? Not now,” said French told the crowd, resulting in a room full of laughter.

Miller has been serving as the principal product manager at ClearCompany, a talent management software company, since March 2023, among other pursuits.

The idea around the company — being able to leverage health data models to show how much companies can save on healthcare costs — is probably still a decade away from being accepted by a mainstream audience, Miller said.

OrgVitals was named one of our 2022 KY Inno Startups to Watch. It has raised approximately $300,000 in total. Miller said since its founding in 2021 as a spinoff of Unitonomy, the company has had seven “knocks on the door” about being acquired — with two offers — but the timing was not right.

“We still know we’re too early. We still have stuff to prove, and I don’t think our investors want us to jump off quite yet, because they also see those signals. That’s how we knew we still got something.”

Takeaways for founders

I first spoke to Ross-Li back in October 2022 to write a profile story on his company, which was out to revolutionize the ticket industry by combining live event tickets and customer relationship management. At the time, I was less than a month into the job.

In addition to being named as one of our 2024 Startups to Watch, Affinna had earned the distinction of being chosen as a winner of the 2023 Render Competition and the 2023 Vogt Awards.

At the time of being chosen as 2024 nominee Affinna had raised approximately $325,000 — with other investors being Keyhorse Capital, Gill Holland and Vik Chadha.

Ross-Li has been working for two months as an engineering lead at Captain, a company founded by Louisville native Demetrius Gray, who earned the 2022 KY Inno Fire Award under the category of “CEO.”

He said in April he saw the writing on the wall to shut things down. Although he was doubling top-line ticket sales each month since November 2023, his company was only taking 5% of that amount for revenue.

Affinna’s initial plan was to grow its client base — those who it was creating tickets for — by a rapid amount, but the company only had around 20 clients.

“You’re never going to be like, zero to a million, right? … But the fundamental problem was doubling [revenue] wasn't enough. we needed a triple, quadruple — something more seismic,” he said.

Ross-Li had two ideas to impart to founders:

“The No. 1 takeaway is that every startup is default debt. You’re already dead. You just don’t know it, so the goal is to figure out how do you survive … “The second thing is that companies need to move faster. If your company was not founded within a [year] of two twos — 2020 is the latest — and you’re still doing preseed [rounds], you’re dead. You’re moving too slow.”

Still, he said his company may have — sports term, incoming — one more “shot on goal.”

Over the last three years, French has invested in 25 to 30 startups, most of which are based in Louisville. He was Affinna’s first investor.

“As an angel investor, you have to invest through the hope of return beyond financial return. You're investing in the startup ecosystem and community, so I stay very focused on Louisville — and to some extent, Kentucky.” French told me. “And so you hope to find [founders] who are going to stay in the game, so to speak, right? Because they’re not going to make it their first. You’re going to lose all your effing money, right? Not always, but most of the time, so you're hoping that your people who you’re investing in will go on to work for other startups.

“What are your commitments to Louisville? Are you going to stay here? Those are the first questions I ask.”


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