It is known that to be a founder is to be resilient. The same can be said for those who are organizers of conferences centered around founders and startups.
On Wednesday morning, I stopped by the Mellwood Art Center to check out the scene on the third day of Startup Week Louisville.
After watching a presentation/panel that talked about the history and successes of Lexington-based Awesome Inc (more on that later), I was able to catch up with Mike DiCenso, who has been organizing and overseeing the event since its establishment in 2019.
“It’s all about creating coalition opportunities for people around thought-provoking content,” DiCenso told me. “The whole purpose of this event is obviously to connect, equip and inspire, but we want to bring in people with varying perspectives in various industries with various experiences.”
DiCenso — who also works as the director of investor relations at startups.com — estimated when all is said and done, the total number of participants would tally around 300 to 400. Given that the event had been drawing an average of approximately 600 attendees, he labeled this time around a rebuilding year. He also looked ahead to next season, so to speak.
“We’ve got big plans for the future. We’ve already built a couple of new partnerships the past few months to grow this into the South by Southwest we really need,” said DiCenso, referencing the well-known conference in early March in Austin, Texas, that pairs the startup and tech worlds with a giant music festival (among other collaborations). We first reported on this overall concept in August 2022.
To bring in the musical component, DiCenso and his team have started to form a partnership with Danny Hayes, CEO of Danny Wimmer Presents and the person who oversees Louder Than Life and Bourbon & Beyond music festivals.
On Tuesday, Hayes actually spoke on stage with John Ramsey, director of partnerships with the Louisville Metro Government.
“That was all about the economic impact the festivals have,” DiCenso said. “Danny spoke a lot about how he's got bigger plans and a lot more innovation to come — and a lot of it is centered around how do we build a South by Southwest.”
DiCenso added that Startup Week Louisville was purposely moved to be in between Louder Than Life and Bourbon & Beyond.
“Our goal is to bring people to Louisville for more than just bourbon and horse racing. … We want to be a glue that ties everything together, too, because artists and creatives, they are entrepreneurs, too.”
Also significant to note is that this is probably the last year that Startup Week Louisville will have “startup” in its title, given that the word has grown synonymous with tech. DiCenso said that the conference will continue to be for founders in all industries, not just those who have launched tech startups.
A possible new name of the event is “TBD at the moment,” he said.
“We want to play off of the fact that we don’t want to be a flyover state. We want to be a destination. … We want to be a waypoint on their travel. And if you think about it, and apply it to the journey of an entrepreneur, there are steps along the way, so we want to be one of those waypoints.”
Everything is awesome
During the session that I attended, I listened to Garrett Fahrbach, program manager of education, internships and outreach at Awesome Inc, explain the origin story of the company, which included the time that its founders flew to California to try to set up a meeting with Facebook founder Mark Zuckerberg, to pitch him the idea of Facebook acquiring their startup, BookExchange.com.
That did not happen, but what did is that BookExchange.com turned into Apax Software and eventually the multi-faceted startup/tech presence as an innovation hub in Lexington, Kentucky, known throughout the state perhaps the most for its in-person “5 Across” competitions.
Fahrbach was joined on stage by Louisville-based GoodMaps CEO Jose Gaztambide and Aram Street, co-founder of CleanSpace, a Software-as-a-Service (SaaS) based out of Lexington. Both men have been involved with several Awesome Inc events — mostly recently with Street winning the latest “5 Across” event in August.
“There’s not a lot of people in my life who have gone through the process of building a business. There weren’t a lot of people I felt comfortable being vulnerable with [in terms of] the problems that come along the way,” Gaztambide told the crowd at one point. “And it was amazing, from day one at Awesome Inc, I think there was the space to be vulnerable to talk about the things that were hard and that are going well.”
Street said, like most founders, that he’s a very competitive person, but that the “5 Across” created an atmosphere of equal parts competition and team-building.
“[It fosters] a healthy competitive spirit, but you’re not out to kill each other, either, right? … You want everybody to succeed, and so I really enjoyed it. I was impressed with just how much we all were very happy to be there and compete against each other.”
One panelist who was not able to attend was Jennifer Mason, co-founder and CEO of TitleWise, a Clarksville, Indiana-based startup that was named as one of our Startups to Watch for 2023. TitleWise was one of two recipients of a new venture fund from Awesome Inc that launched on Aug. 1. The other company was Thynk Health, a medical tech manufacturer headquartered out of Lexington.
The amount of the fund? You guessed it: $5 million.
Fahrbach told me afterwards that applications continue to be open for local startups.
