The Conversation on a Plane that Changed Everything
- 12 minutes ago
- 3 min read
Some companies come to StartingBlock wide-eyed and just getting started. Earthling Interactive came in with 20 years of history behind them, and a very different kind of story to tell.
The Madison-based technology consultancy has been a fixture in the Madison community since 1999, when two founders launched what would eventually become one of the region's most adaptable tech firms. Through the rise of the internet, the shift to software-as-a-service, and now the AI revolution, Earthling has done something most companies don't: they've kept evolving.
"We've seen a lot in 25-plus years," says the company's CEO, John Samuelson. "But AI is certainly adapting faster than anything we've seen."
Earthling Interactive specializes in helping businesses in construction, agriculture, and higher education untangle the mess of manual processes, legacy systems, and disconnected tools that slow teams down. Their work includes custom software, systems integration, and now AI agent solutions.
The Right Space at the Right Time
When Earthling joined StartingBlock in 2021, it wasn't because they needed mentorship or a launch pad. Coming out of COVID, the team had transitioned to a hybrid work model and simply didn't need their full office space, but they still wanted something private and professional.
"It fit perfectly for us at that time," John explains. "And having some established, mature businesses in the mix was a nice difference.”
That mix turned out to be one of the most valuable parts of the experience. Running into other business leaders in the hallway, sharing a floor with companies across wildly different industries, attending Lunch with the Founder events, it was the kind of organic connection that only happens when you put curious people in the same room.
The practical side mattered too. Saving on rent during a pivotal transition period freed up capital to invest in people, including the roles needed to step into the next chapter of the business.
A $50 Million Conversation at 30,000 Feet
Twenty-five years of business means twenty-five years of stories. But one stands out.
Back around 2006 or 2007, before Earthling had made its full leap into web application development, the CEO at the time struck up a conversation with a stranger on a plane. That stranger mentioned a startup in Wausau building a healthcare industry application, a project they weren't interested in taking on. They passed along a name. Earthling followed up, went through the sales cycle, beat out competing firms, and landed the project.
It was their entry point into web development. That Wausau company eventually sold for $50 million. Earthling stayed on as a service partner through it all.
"It was just a conversation on an airplane," the CEO says. "One thing led to another. We never pass up an opportunity to have a conversation."
It's a story that doubles as a business philosophy, and one that takes on new meaning as AI reshapes how work gets done. "The charismatic, relationship-based person is going to increase in value," he says. "AI is going to infiltrate a lot of industries, but the person who can step in, connect, and fill any room, that's irreplaceable."
What's Next
Earthling is leaving StartingBlock on a high note. In April 2025, the company was acquired by Lift Consulting, a Madison firm with complementary strengths and shared ownership vision. The two companies are now moving under one roof (still in Madison), and one direction.
The team recently hired a Chief AI Officer, a former Earthling employee from 2011–2018 who spent years deep in enterprise AI work before returning to the fold. It's the kind of full-circle moment that a 25-year company earns.
As for the five-year vision? Simple: become the staple name people in Madison, Dane County, and across Wisconsin think of when they think process automation and custom AI.
"I want to be that trusted company that makes an impact across this industry," John says. "We've made strides. Now it's about making that brand even stronger."
StartingBlock gave Earthling Interactive the space, literally and figuratively, to keep building. And for a company that's been reinventing itself since before most of today's startups existed, that's saying something.
Earthling Interactive is based in Madison, Wisconsin. Learn more at earthlinginteractive.com.
