How Two College Teammates Navigated the Shift from Friends to Co-founders

Second Mile co-founders
Jess Vossler (EO Columbus) and Hannah Lee (EO Nashville).

From the day they met, Jess Vossler and Hannah Lee had no choice but to communicate constantly and trust completely. In 2010, the duo were members of Jacksonville University’s inaugural women’s lacrosse team — a collection of scrappy freshmen and a few transfers attempting to forge a Division I program from scratch. Jess, a transfer sophomore, quickly became a vocal leader on defense. Hannah, a laid-back freshman goalkeeper, served as the anchor behind her.

Mistakes were inevitable. Tempers sometimes flared. But their bond deepened through practices in the Florida heat, stinging losses, and shared ambitions. “I have literally seen her lose,” Hannah recalls. “I know what she’s like when our backs are against the wall and vice versa. The degree of trust between the two of us is so high.”

That trust would prove essential when, nearly a decade after they first shared a practice field, they became teammates yet again. Together, they founded Second Mile, a marketing, HubSpot, and web development agency built around their complementary skills — and enduring faith in one another. 

Hannah (left) and Jess bonded during Jacksonville University's
inaugural women's lacrosse season.

Forever Teammates

The duo’s lives diverged after college, though their friendship held strong. Jess earned an MBA and gravitated toward marketing roles in sports and higher education. Hannah, meanwhile, worked in the nonprofit sector, then bounced between boutique and massive marketing agencies. She soon realized she missed the intimacy and camaraderie smaller teams afforded. Plus, she noticed an emerging niche. “My parents were Chick-fil-A owner-operators,” she says. “I was starting to work with a couple of Chick-fil-A clients, and really saw a need to support them with this new social media thing that was starting to blow up.”

The two friends would reunite on regular group trips and, invariably, found themselves dreaming up business ideas over glasses of wine: A mentorship program here, a tech tool there, but Google searches the next day usually revealed that someone had beaten them to the punch. Until, in 2016, they realized they had already amassed enough clients they could pool together and start their own marketing firm. Hannah could leverage her Chick-fil-A accounts and Jess would be able to parlay her current employer into a client. With no outside investment required, they had revenue and momentum from day one.

It didn’t take long to find their rhythm. Jess, ever practical, handled operations and systems. Hannah brought vision and energy. “We always used to refer to ourselves as the ‘how’ and the ‘wow,’” Jess says. “Hannah would have these big ideas. I’d come back and say, ‘OK, great: How are we going to do that?’”

To protect their friendship, they drafted an operating agreement “on LegalZoom for something like US$40,” Jess chuckles. It included promises not to contact each other about work after 8pm and to go into a 50-50 partnership. Confidants warned that the arrangement could scuttle their friendship and that one should own the company and the other should be an employee, but the duo was committed to remaining true teammates.

“We felt really strongly that we didn't want to that,” Jess says. “We felt like we could be mature enough to figure out how to prioritize our friendship.”

As the company scaled, those boundaries started to blur. So, they adopted practices from the Entrepreneurial Operating System (EOS), implementing a more rigid structure and accountability charts. By 2020, with the company bringing on employees, they codified their roles: Hannah, the dreamer, would become CEO and Jess, the pragmatist, would serve as Chief Solutions Officer.

“I think that was a game-changer,” Hannah says. “It set some boundaries on who is deciding what and, ultimately, to hold that person accountable for what they are responsible for.”

Building the “Anti-Agency”

The pair knew early on that they didn’t want to become the kind of agency that glamorized burnout, where long hours were rewarded only with in-office dinners and a pat on the back. “We were passionate about creating the anti-agency,” Jess says.

So, they did. Long before it became a trend among employers, Second Mile adopted a four-day workweek. It was no gimmick; it was a cornerstone of the company’s culture. That shift didn’t merely boost employee satisfaction — it made them better. Tighter. Sharper.

Fridays became “release valve” days, which offered a buffer for life away from work or time to catch up if they had to step away during the week. Mondays through Thursdays? Focused and efficient. Employees work remotely: Jess lives in Columbus, Ohio, and Hannah in Knoxville, Tennessee.

“We wanted to create a workplace where people could do great work and still have lives,” Hannah says.

It worked. They eclipsed US$1 million in revenue. They pivoted to specializing in HubSpot integration, purchased a small web development agency, and brought on a third partner, Sam Crokett, who added new technical prowess. Eventually, Second Mile became a preferred web vendor for the University of Tennessee — a full-circle moment for Hannah, a proud alum. (She left Jacksonville after her freshman year.)

Still, the ride has not always been smooth. “The lines between best friend and business partners can get very blurred and really difficult,” Hannah says. “Sometimes that means some really hard conversations in a business setting, and some tough feedback.” They have learned, though, to take turns, to anticipate each other’s needs, and to grow together through life’s new seasons, including Jess’s trio of maternity leaves and Hannah’s sabbatical. “We think about the whole person,” Jess says.

The duo have emphasized work-life balance
and support one another away from their company. 

Worth the Risk

Hannah joined Entrepreneurs’ Organization (EO) in 2021 and is now a member through the Nashville chapter. Jess became a member through EO Columbus in 2024. There, the pair found peers in their respective chapters who have helped them through difficult times, such as when a vital employee abruptly left the company. Both relish their Forums, where they can vent, learn, and return to their partnership stronger.

“When you do have a co-founder, it is really helpful to be able to talk about some things that are maybe difficult in our dynamic in a safe space,” Hannah says. “It has been super healthy for our relationship.”  

Starting a company with a close friend can be a fraught decision if it’s devoid of intentionality, clear and direct communication, and trust. Life’s biggest moments happen in parallel with projects and pitches. Jess and Hannah, though, cannot fathom making it this far without one another. Together, they have come a long way from those scalding hot days defending a goal for a fledgling lacrosse program, remaining trusted teammates though wins and losses alike.

“It is going to be hard like a long-distance relationship is hard,” Jess says. “But if you are excited about it, if you can trust the person, and if you have aligned values? Go for it — 100 percent.”

Hannah has long felt the same: “This is the best ride of my whole life,” she says. “Getting to do it with one of your best friends? I am so lucky … It is the hardest thing you will ever do, but it is the best thing you will ever do.”