We all know the old saying, “third time’s the charm,” but have you ever asked yourself why the third time is the charm? I just asked Google (which gave me completely worthless answers), but I have a hunch that in the case of Helme co-founder Brent Baumgartner, it has nothing to do with luck and everything to do with the hard-won wisdom that is failure’s sweetest gift.
Last Friday, I had an enlightening conversation with the energetic Baumgartner—who at the age of 22 is now on his third, very promising startup—about what he’s learned so far on the entrepreneurial journey, and his story was too good not to share.
“I knew I wanted to do some kind of entrepreneurship,” said Baumgartner, whose father was a small business lawyer. He had it in the back of his mind when he arrived at college, and in the course of his first year, he founded not one but two tech startups—the first a live music discovery app, and the second a social messaging app for large events—with funding won at competitions.
While both these early ventures ultimately failed, he says he learned a lot that first year, and benefitted from having a team that worked well together. But he remembers most vividly the moment he and his partner were told by a more seasoned entrepreneur, “If you don’t love an idea enough to want to be working on it 7 years in the future, you shouldn’t start it.” They looked at each other, he says, and understood they needed to keep thinking.
In the wake that experience, he also had a second, more business-minded realization that “boring applications win.” Having had two seemingly more exciting applications fail, he realized that consumers were drowning in these types of apps—so much so that it made them difficult if not impossible to get on board. “It may be sexy, but not viable as a business,” he said of the type of apps he was initially working on.
After his second venture failure, he came up with a theory as to three things he was looking for in his next go: a “boring” app for a niche market, a source of recurring revenue (i.e., institutions or other businesses to sell to), and finally the ability to partner personal technical expertise with expertise in the field. And in the spring of 2014, he and Koleman Nix created Helme with all three of these elements.
The seed of the idea came from their field expert, Nix’s father, a former consultant turned head-of-school who’d created a spreadsheet to manage all his school’s budgeting. When the younger Nix and Baumgartner realized they could improve on the basic spreadsheet idea by creating an application for budgeting and strategic planning—something K-12 schools really needed—Helme was born.
They rolled out their first MVP late that spring, but as both Nix and Baumgartner were college students, they had to find ways to build the company while also attending classes and working internships.
“Have you ever heard of polyphasic sleep?” Baumgartner asked me, laughing. He then explained how he trained himself to sleep only a few hours at night and take a few short naps during the day, in order to work on Helme while also holding a 9-5 internship that first summer. But by the end of it, they had something they could sell.
The following October, he and Nix attended a conference of the small schools that would be their first customers, which he now describes as “one of the most defining moments in the company.” After offering an optional, sit-down information session, they walked away with a handful of committed sales, and twice as many schools who were interested in hearing more.
Now, a year after that conference, Helme is still growing, and though they still do much of their sales at conferences, they’re working on new growth strategies that don’t involve these large events.
“It’s so much fun,” said Baumgartner of the total experience, shaking his head. “Overwhelming, but the most fun I’ve had.” I told him it sounded like living in a board game, and he shared that it did in some ways feel like that—including the stressful parts.
There were times, he said, “I was probably one or two conversations away from giving up on Helme.” But after sitting down with Kevin Eisenfrats, a fellow entrepreneur and i.Lab alumnus, he became convinced he needed to stay. And now, halfway through the accelerator, he hasn’t looked back.
“Part of being a founder is fighting off the existential questions,” he said, adding that if you weren’t questioning, something was probably wrong. (Which, if that’s any indication, hopefully means a number of us are onto something, myself included.) You do, however, learn to face the questions and put them in their places. That’s what wisdom is about—entrepreneurial or otherwise.
