In early 2015 — right after we closed the residential model — I was having one of those “everything is falling apart” lunches with a fellow entrepreneur. Beset by the usual startup anxiety, I bemoaned the tensions between operations, fundraising, and recruitment. I didn’t have enough time to do all three well, and recruitment was suffering most.
“Hire someone,” my friend urged.
“We can’t afford it,” I rightly retorted.
“Well” he paused, “you’d rather fail trying than limp along to the finish.”
He went on to help me see that of the many strained resources in a startup, the most crucial is cognitive — there isn’t time to focus on every important problem. While tough prioritization is needed, the greater need is hiring trusted folks to own a problem or two. So I took his advice, and posted a job with no way to pay the person we hired.
Too often, startup stories become a founder’s narrative, but I’d argue the most important characters are the first followers — those who catch the vision, join a company, and help build it into something real. James was the first employee at PelotonU, and his courage is worth a book of its own. Then Sarah, my friend and co-founder, joined and built everything good we get credit for.
Somehow, we’ve been joined by ten more risk-takers since that anxiety-ridden conversation in 2015. Here’s a glimpse of how each person helped us learn to better serve our students.
That first to answer the call was Samantha, who responded to that job posting in April 2015. Her task was finding students, and as so often happens, she not only did that well but brought more of what we never knew we needed. Sam taught us Salesforce, and then generosity. While managing short-term enrollment deadlines she still found a way to make every applicant feel known. We didn’t know then how big the choice to start college can be (up there with buying a car, turns out) and Sam knew how to make each student know their educational journey mattered.
Then Reagan signed on. Sarah’s caseload was full and we had this vague sense that how we coached students was unique. We needed someone we trusted to listen and encourage in private mentor meetings we could rarely observe. Reagan knew that purpose because he was there as a friend helping pick the logo when we started.
Once on the team, he coined the missing language — What a Thing — to honor the everyday sacrifices students show in their commitment to school. A year later, when Reagan began his own journey as an entrepreneur, we didn’t think we’d trust someone the same way again. But we did.
Holly applied on a friend’s suggestion and was one of many “no way this person would come work for us” hires. She lives in Denver now, but before leaving she helped us grow up. Y’all, you should see the Google Docs she wrote — research-backed processes about what it means to walk students through trauma, shame, hope, and purpose. We teach these frameworks to others now, and students Holly hasn’t met will earn a degree because she codified an approach to grace and accountability that creates a space for students to do the impossible.
After Holly, Erika joined our ranks. She had dedicated her career to serving others, and was the first to notice things undone and ask “what else can I do.” Alot, it turned out. Erika’s knack for excellence and project management taught us all how to see our roles as more than a job description and to think creatively about how else to support our students.
Ashley, our third coach, started next. A former university professor and current keeper of our culture, she writes a regular blog to remind students about the small victories that add up to big goals. Ashley has taught us to serve from our wounds as well as our wisdom. There’s nothing more courageous than vulnerability, and Ashley continues to remind both students and staff about our value on the days when we forget.
And then Sara, who brought a deep expertise in helping high school students make the jump to college. She has a passion for justice and love for tracking data that’s professionalized our work this year. As we expect to add two more coaches and a third site next year, its Sara’s adeptness at building systems that will enable PelotonU to grow without losing the living room culture.
While great coaching is the heartbeat of our work, our students also need a place to study — a safe and supportive community where they can focus on school without the pressures of work and home.
We didn’t know how important that was until we met Robert. He responded to a job posting on an obscure listserv and became an anchor of our work — running evenings at our south site in Montopolis after his eight hour day job. Robert is teaching us that the magic of a space isn’t the amenities or availability, but instead in feeling known and safe when you arrive.
It’s this sense of being a part of something bigger we’re only now learning to create, and it’s what Karen brings each evening to the central site. Y’all, only two years ago our team worked every evening and Saturday, and when we thought we were hiring folks to keep the lights on, instead they taught us learning happens when students feel like they belong.
It’s become so important that we hired Kat this month to provide the same support during the day at our central site; ensuring there’s not an hour when our students don’t have ready access to tutoring or advice. Only weeks in, Kat was the first person to welcome our November cohort, introducing herself to each one on their first day, reminding them she’s on the same journey as a student, and promising to be there to help.
As crucial as coaching and community are, they only happen if others in Austin know we’re here to help. We first realized this when Samantha moved to Scotland and we saw the trust she had built with partners and applicants.
So, we expanded recruiting to include advising and hired Navid to make it real. He started nine months ago and has quickly become the face of PelotonU in the Austin community — leveraging his curiosity and warmth to tell employers and nonprofits we’re here to guide anyone who feels stuck and wants to pursue a degree.
Our expanded focus on advising means we’ll now chat with anyone interested in continuing their education (even when not with us). We needed someone you could feel smile over the phone, and found her in Avianne. Fresh from helping launch career services for the ACC ACCelerators, she’s one call away for folks who need a personalized plan for how to get back in school.
They worked alongside Briana until recently, who holds two records: the first student to join our team, and only one to find PelotonU on Instagram. Hired to help recruit high school students, Bri grounded every staff discussion in our commitment to put students first and reminded us that beauty and details are important, even when we’re running fast.
These are the coworkers, friends, and risk-takers who have joined our peloton and lifted us to heights I didn’t imagine we’d reach six years ago.
Yes, there’s still hard days and moments I feel lost, but the work’s carried now by stronger and steadier hands than my own. To reach our vision for building a model to serve millions of students around the country, all without forgetting to value each individual student — that work takes a tribe, and I’m grateful for the one I work alongside.