Today we’d like to introduce you to Ashley Kent.
Hi Ashley, thanks for joining us today. We’d love for you to start by introducing yourself.
I actually went to school for kinesiology and fully planned on becoming a physical therapist. I’ve always loved the human body and healthcare—it just made sense. But when I started doing my practicum in outpatient PT clinics, I realized pretty quickly that the work felt repetitive. It didn’t spark the energy or curiosity I naturally have, so during my second semester senior year, I pulled all my PT school applications and found myself having to figure out what was next.
I’ve always been a creative person—my mom was in marketing, so it had been in the back of my mind. I decided to explore it more seriously, applied to a bunch of jobs… and got no traction. So I started working at a barre studio while still helping out at a PT clinic, and I offered to do marketing for free just to learn. It was super small-scale—getting more people into the studio—but it was enough to get me hooked. I tend to throw myself into things fully, so I was learning fast, completely self-taught at that point.
When we moved from Knoxville to Nashville, I decided I wanted to find a real marketing role. I knew I didn’t have a degree or a traditional background, so I figured a startup might take a chance on me. I got on AngelList, found a company called HoneyCo Homes, and drove to Nashville the next day for an interview. The CEO hired me on the spot—he didn’t even look at my résumé. He just had a gut feeling that I was a go-getter. I became the very first hire.
Day one, he asked me to figure out the accounting software. I had zero experience in accounting—my entire background was in science—but I just said “sure” and figured it out. That ended up being the theme of my time there. I touched everything—product, marketing, sales, investor relations. I even ended up pitching to VCs at one point without knowing what I was doing. I just kept showing up and saying yes.
Eventually I carved out a focus in marketing, and it was clear how helpful it was to bring an owner’s mindset into that work—understanding product and sales deeply made me a better marketer. I also saw how startups really operate, especially venture-backed ones. I’ll never forget the moment an investor told us we weren’t burning cash fast enough. It was such a wake-up call about how different the world of fast-growth startups is. Everything is about speed and traction—and marketing plays a huge role in that, even though it’s often brought in too late.
I saw a gap in the market for someone who could come in early and help startups build real go-to-market strategy—not just a deck or a rebrand, but actual execution. So I decided to start Clearstart. I had already built relationships through all the sales and fundraising work I’d done, so I leaned into that network. I took on a few clients, worked ridiculous hours, and quickly realized that my personality is very all-in. The retainer model worked best—it gave me space to be a true partner rather than a drop-in consultant.
At first, I worked with all kinds of startups. But over time, I found myself more and more drawn to healthcare. It just hit differently. I’d be talking to founders in other industries and realize I wasn’t that excited about what they were building. But in healthcare, the founders I was working with were often building something because of a deeply personal experience. Something had gone wrong with their own health journey, or their child’s, or a parent’s—and they were out to fix it. That purpose was something I could really get behind.
So about two years ago, I decided to go all-in on healthcare. Today, Clearstart exclusively serves health tech and healthcare organizations. We’ve evolved from working just with early-stage startups to now partnering with Series A+ companies that are moving beyond founder-led sales and need to build scalable growth. On the other side, we also work with enterprise healthcare orgs—health plans, health systems, MSOs—helping them modernize their brands, build marketing infrastructure, and launch new clinic footprints.
It’s been amazing to now support both sides of the ecosystem. We help startups sell into enterprise, and we help enterprise companies become more agile and innovation-forward. We’re now a team of 15 serving over 20 clients. I’m proud to say I’m part of the 2% of women founders who have passed $1M in ARR—and it’s been an incredibly rewarding (and exhausting) journey.
I launched Clearstart while pregnant with my first child, and hired my first employee while pregnant with my second during the pandemic. I have two young kids now, and my husband is a partner at a large law firm. So, life is not exactly slow-paced. But I love what I do. I love building something that helps other people build. And I love that we’re playing a real role in shaping the future of healthcare.
We’re based in Nashville, and I care deeply about contributing to the healthcare and startup ecosystem here. Long-term, I have visions of bringing these companies together—maybe even starting a fund or taking equity in the ones we believe in most. But for now, I’m focused on building Clearstart into the go-to firm for healthcare marketing strategy—one that can show up for founders and operators the way I always wished someone had shown up for me.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
Definitely not a smooth road.
I started Clearstart while I was pregnant with my first child, and then found out I was pregnant with my second in March 2020—the same week COVID shut the world down. So I was navigating a newborn, a toddler, a global pandemic, and trying to keep a business afloat all at once. Meanwhile, my husband was in the thick of M&A law, working insane hours on his path to becoming partner at a major firm. It was chaos.
I’ve always felt like I’m being pulled in a thousand directions. I’m not the “Pinterest mom.” I’ll never be the class room parent. But I do hope my kids grow up knowing their mom built something meaningful. One of my favorite memories is when my daughter visited my office—she walked in, saw the team working, and set up a desk for herself calling it the “boss’ chair” because she knew the company was mine. She was so proud.
Beyond just the personal juggling act, the hardest part of scaling has been the people side. Building a company requires stepping out of the day-to-day, but that’s tough when people associate the quality of the work with you personally. I’ve had to learn how to delegate, how to build systems that don’t depend on me—and that’s been way harder than I expected. I think I had also just expected everyone to work like me, but I’ve quickly learned you have to teach people to work the way you want them to work. If they worked like you, then they’d have their own company.
There’s also been more team churn than I’d like. But we work in two of the most burnout-prone industries: early-stage startups and agencies. That combination creates a pressure-cooker environment, and I’ve had to learn the hard way how to hire better, support better, and course-correct faster when something’s off. It’s still something I’m working on. I care deeply about my team, and it’s been hard to reconcile that care with the reality that not everyone is going to be the right long-term fit.
Client challenges have been real, too. I used to think I had to make every client happy no matter what. Now I know that the wrong client can be more costly than no client at all. Misaligned expectations, toxic dynamics, or scope creep—it all takes a toll. I’ve learned to trust my gut and walk away sooner when it’s not the right fit.
And then there’s just…me. I’m the kind of person who’s always pushing for better. I struggle to pause and feel proud of what I’ve built because I’m already thinking about what could be improved. That drive is part of what’s made Clearstart successful—but it can also be exhausting. It means the goalpost is always moving. It means I sometimes miss the moment I’m in because I’m already chasing the next one.
So no, it hasn’t been smooth. It’s been scrappy, imperfect, incredibly challenging—and incredibly worth it.
As you know, we’re big fans of Clearstart. For our readers who might not be as familiar what can you tell them about the brand?
Clearstart is a marketing and strategy firm built specifically for the healthcare space. We partner with both sides of the ecosystem—early-stage digital health startups that are bringing new solutions to market, and larger healthcare organizations like health systems, MSOs, and health plans that are trying to modernize and scale what’s already working. We sit at that intersection, helping the innovators sell to the incumbents, and helping the incumbents operate with more clarity and creativity.
What sets us apart is that we’re not just a marketing agency. We’re a deeply embedded partner. We’ve designed our model to be high-touch, fast-moving, and rooted in strategic context. Most of our clients are navigating massive ambiguity—trying to validate a product, scale a service line, or communicate complex ideas to multiple stakeholders. Our job is to bring structure to that chaos and move quickly toward traction.
We’re known for being clear thinkers and doers. We bring a founder’s mindset to everything we do—whether we’re building out a GTM strategy, rebranding a health plan, or figuring out how to activate 50 clinics across five states. We specialize in stepping into complex problems and untangling them with a mix of smart strategy and beautiful execution.
Brand-wise, what I’m most proud of is the trust we’ve earned. Our clients don’t come to us just for a one-pager or a website—they come to us when they need to figure out how to grow, when the stakes are high and the path isn’t obvious. We’ve been able to stay small and nimble while operating at a really high level, and that’s something I never want to lose.
We offer everything from GTM planning and brand development to campaign execution and marketing infrastructure. On the startup side, we often serve as a fractional marketing team for founder-led companies that are just starting to build out their sales and growth engines. On the healthcare delivery side, we support leadership teams in designing corporate marketing strategies, launching new products or service lines, and building the systems needed to scale.
More than anything, I want people to know that we care deeply about the impact our clients are making. Healthcare is messy and slow to change—but there are founders and operators out there who are doing the hard work of fixing it. Our role is to help them break through the noise, get the traction they deserve, and ultimately help more people access better care. That’s what we wake up every day to do.
What was your favorite childhood memory?
It’s hard to pick one specific memory, but all my favorite ones from childhood involve being on the lake with my dad. He was an incredible water skier—he could even barefoot ski—and in my eyes, he was just larger than life. We were so much alike. He had his own company too, and now that I’m running my own business, I see just how much of him is in me.
He was diagnosed with MS a year after he and my mom got married, but his symptoms didn’t really start to show until I was in middle school. For most of my childhood, he was active, hardworking, fun. He worked a lot—often late—and I remember my mom would joke, “Your dad’s in the doghouse,” and my siblings and I would run outside to the actual dog pen to see if he was really in there.
Even when he was home, he was working. I didn’t understand it at the time, but now I get it. He carried so much responsibility. He cared deeply about his team and wanted to grow something meaningful. And then, when his health started to decline, all of that was slowly taken from him. He eventually had to go on disability and sell the company for next to nothing. After that, he talked a lot about how family was what mattered most.
That stuck with me. And now that I’m a founder and a mom, I think about it constantly. I have the same drive he had—I’m always building, improving, pushing forward—but I also try to remember the lesson he learned the hard way. I’ll never be the typical room mom, but I hope my kids grow up seeing that I built something meaningful—and knowing they matter more than all of it.
Contact Info:
- Website: https://www.theclearstart.com
- LinkedIn: https://www.linkedin.com/company/theclearstart/
