Gillin grew up with a father who ran a mini golf course, and he and several of his eight siblings worked there as teenagers. They saw firsthand what it took to run a company, and to this day, Gillin said, most members of the family own their own businesses in different industries.
At first, Gillin struck out in real estate. He spent three years in his very early career on the job, even though it wasn’t the right fit — “on the first day I knew it wasn’t for me,” he told Technical.ly. But it was at that job where he got his first idea for a venture: Gillin remembers watching a lot of coverage of the 1992 presidential election during that time, and a key issue of the race was education.
“I started to think about an idea where you could get money back for your kids education on every purchase you made,” Gillin said. He researched it, and talked to people who were excited about the idea. “That’s what really got me going” on entrepreneurship, he said.
The birth of Relay
That idea didn’t make it to an actual business, but it set Gillin up for future ideas in the payment space. He launched his first company, Ecount, in the late 1990s, with Paul Raden. The pair are known for selling the Conshohocken electronic payment firm to Citigroup in 2007.
It was in the wake of selling Ecount that Gillin recalls getting the idea for Relay.
“I was sitting in my car, and I didn’t know what we were doing next,” Gillin said. “But I got a text from AT&T saying that they were going to turn my phone off. Of course they were — the company had paid for it all this time.”
The text contained a link to AT&T’s customer service, and within minutes he had solved the problem. With that simple text and a smart link, Gillin thought, so many businesses would have the ability to deliver incredible customer service.
In the decade and a half since, Gillin’s launched Relay, which created a software to help businesses get through to customers outside of traditional email marketing. The mobile engagement program essentially enables businesses to deliver communications through individual feeds that guide customers to take specific actions, like scheduling a service.
Lessons for round two
Gillin’s taken a few lessons from being a second-time founder. He said his goal as CEO of Relay is to build a company that’s “the best place you’ve ever worked.” The company recently doubled from its early 2020 numbers of about 50 staffers to 110, and is up from 30 million daily users to about 80 million. His tech team makes up about 60% of the workforce, and while some employees are fully remote, many are in the Philly area and occasionally report to the company’s Radnor office.
Another learning curve came with age. This time around, Gillin said he’s older than many of his colleagues, whereas at Ecount, he was peers with most of the employees. It’s taught him to motivate a different generation of workers, he said, and to create workplace culture intentionally.
He’s learned, too, about venture capital and timing. The company’s last major raise was a $30 million round in late 2019 — yes, just before the pandemic — with nearly $60 million in total pumped into the tenure.
“For startups, you can never run out of bullets,” Gillin said. “Be well funded, raise when you don’t need it. Raise from a position of power. It’s the biggest mistake people make, they get out in front of themselves and run out of cash.”
He also cautions against waiting too long to put a product on the market. Send it out there and see what sells, the founder said, before you’re too invested in what you built. And on the technology side, build your platform with as much optionality and flexibility as you can from the start. You never know where the product might take you, but you’ll be happy when it’s easier to take it in a new direction.
And with two-and-a-half decades and many opportunities to fail under his belt, Gillin’s biggest startup advice is to avoid quitting at all costs.
“It sounds ridiculous, but don’t quit. There’s always a solution, even if it’s your third, fourth, fifth try,” Gillin said. “Ecount had a successful exit, but that business was dead on arrival a few times, and we always found a way.”
You could say it’s a lesson he’s been honing his whole life.
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