Signed from
the NICU floor.

OptionsMD sold to Resilience Lab in September 2024 in the $10–20 million range — an all-equity deal with a one-year earnout its founder carried alone, run without a bank, and signed the morning his son was born.

The day his company sold, Kyle Pierce signed the closing documents from the floor of a hospital NICU, laptop open. His first child, a son, had been born that morning, and almost no one on the other side of the deal knew it. He’d kept the birth quiet, worried it would give his buyer a reason to walk.

“The craziest back and forth I will never forget,” he says.

Kyle and his co-founder, Morgan Hewett, founded OptionsMD, an AI-powered telepsychiatry company for treatment-resistant mental illness, in April 2020. They sold four and a half years later, in September 2024. Kyle ran the acquisition himself, forced to go to market earlier than expected when the fundraising market turned. The deal closed in the $10–20 million range. Investors got their money back several times over; Kyle got an earnout he would have to carry alone.

The average patient who found OptionsMD had already tried seven medications. They arrived, as Kyle puts it, with “incredible distrust in the system,” but also open to trying anything, because everything before had failed.

Kyle and Morgan had each come to know the problem personally. Morgan’s brother lived with treatment-resistant depression and eventually found the right treatment, but only at a high-end clinic most people couldn’t access. Kyle had lost a close friend to suicide after a long battle with depression. Kyle was a health tech attorney, with the litigation and negotiation instincts that came with the work; Morgan came out of Meta during what she calls the peak of digital health marketing.

The community came before the product. It started as a support group for treatment-resistant patients, which gave them early testers and what Kyle calls a “gold mine of data.”Their first marketing attempt missed badly — founder-forward branding full of smiling faces, aimed at people in the worst stretch of their lives.

Eventually, they moved to a more serious and clinical approach, because that was what these patients would trust.

OptionsMD raised just over $4 million across two rounds during health tech’s flush years. They went through the Techstars/UnitedHealthcare accelerator, which gave them what Kyle calls “huge green-flag signage” with payers. It also showed them how large and bureaucratic those insurance relationships were, and how long they would take to convert. Underneath all of it was a harder question: whether a treatment-resistant population, the patients who need the most help, could be commercialized in a venture-backed way at all.

The funding environment flipped almost overnight. After a couple of years of record investment, investor appetite for digital health, and mental health in particular, fell off a cliff. They were still having about the same number of conversations, but far fewer converted. Even investors who had backed them before had “indexed enough in mental health” and moved on. For two founders with a track record of raising, it was a frightening moment.

With roughly four months of runway left, an investor called and suggested they sell instead. Kyle had already settled on how he wanted to handle it. Rather than run the company into the ground for ego, he made his peace with it early.

In Kyle’s view, most founders wait too long for a buyer to knock. “Unless you’re a billion-dollar company, you have to make yourself visible.”

He ran the acquisition like a sales process and sorted potential buyers into three groups: technology companies, mostly chatbot platforms, that wanted AI capability; service providers that needed expertise and infrastructure for a difficult patient population; and companies wanting into mental health that would use OptionsMD to get there.

The deal was below the size where a bank makes economic sense, so instead of hiring one, he kept a banker close as a sounding board, minimized the role whenever it created friction with the buyer, and later paid him in equity though he wasn’t obligated to. His pitch was never that they needed to sell. It was a collaboration: “We’re having this conversation because we think there could be something here. You have an opportunity that could benefit from what we’ve built.”

He also knew something useful about the buyer. Their eventual acquirer, Resilience Lab, had recently failed to close another acquisition, which meant its board badly wanted this one to land. Kyle used that to his advantage; it meant he wasn’t the only one at the table under pressure to close. Outreach began in early summer 2024, serious conversations were underway within about two months, and the deal closed in September.

OptionsMD sold in the $10–20 million range, in an all-equity deal with an earnout, and the structure treated the two sides of the cap table very differently. Every investor was made whole at close and then some, on a 5x multiple of revenue. Kyle’s own upside was the earnout, and he carried that risk alone.

“I fell on the sword,” he says. The investors came out clean while he took on the exposure.

The earnout itself was punishing. It ran one year, short for an acquirer earnout, which usually stretches three to five, and it was milestone-based, so it was effectively all-or-nothing.

Kyle’s first move was to soften that. He negotiated a prorated floor that started paying at 50%, so hitting half the milestones meant collecting half the earnout. It wasn’t a standard term, and he didn’t win it with a spreadsheet. He won it by asking the acquirer a question they couldn’t easily wave off: “Is there no value in the work if I make it partway there?” The message underneath was that he was going to work hard for them and wanted them to want him to win.

Most of his leverage he had to create. “There’s no playbook for leverage unless you really have it,” he says, so you pay attention to everything, “down to what people are saying, the language being shifted.”

You have to turn every change or ambiguity into something you can press on. The clearest case became what he calls a “golden ticket”— the buyer misunderstood how the earnout would be structured, and instead of smoothing it over, Kyle let the gap open into a formal disagreement and reframed the terms around it.

His legal training helped and hurt in roughly equal measure. It gave him a feel for what was standard and what was worth fighting over. But a clause asking the buyer to cover OptionsMD’s legal fees “as is customary in deals of this size” was boilerplate to him and an insult to them, and it “rocked the boat”enough that he had to walk it back carefully. He’d written it the way a lawyer writes; they read it the way an acquirer does.

The final stretch was fragile. “Every day there was a new issue. Every day something could go wrong,” he says.

It closed on the day his son was born. He signed from the NICU floor, still saying nothing to the other side about the birth, in case it handed someone a reason to pause. Morgan left right after closing. Kyle stayed for the earnout.

Staying turned out to be its own job. Kyle ran the integration, restructuring the company to fit the acquirer’s model, cutting costs, and changing employee compensation almost immediately. There was no growth moment; he had to be austere before anyone could talk about expansion. He did all of it while learning to be an employee after years as a founder, becoming a new father, and adjusting to the shift in his partnership with Morgan.

He describes mourning the loss of being a founder, going from “spectacular or talented” to “redundant and superfluous” inside a bigger company where his skills were already covered. No one quite acknowledged that he was the one required to stay. A six-figure salary was not what had motivated him as a founder working for equity.

Then a final twist. With a few months left on the earnout, the acquirer let him go in a restructuring, no cause. He’d hit enough of his milestones that the full earnout was written into his separation agreement, so he took the money and left. The offboarding was clumsy. This was Resilience Lab’s first acquisition, and the inexperience showed. “They kind of let me go in an employee way,” he says. “I was just looking for the respect of: this is my company.”

His advisor, Billiana Fray, helped him see the upside: a shorter earnout than most founders sign, a chance to decompress, and time to be present for the first months of his child’s life. He also takes some quiet satisfaction in the returns. Every investor got a multiple. “You can’t fawn on me,” he says, “but you also can’t say anything bad about what happened.”

He’s clear about why he didn’t push for more. At 31 or 32, in his first company, he decided not to optimize for the last dollar at the cost of everything else, which he calls “a short-sighted view.”A $10–50 million outcome, in his telling, can be worth more than a bigger one loaded with preferences and loss of control.

“This is not going to be my last crack at the apple. I can’t feel anything but incredibly proud that we survived a fickle market. We got out, we’re okay, everyone’s happy. Success.”

Kyle Pierce, OptionsMD

Kyle’s next company, Half Past Eight, sells what it calls “wellness that moves with you”: 12-hour time-release transdermal patches for sleep, energy, mood, and stress, made from adaptogens, aminos, and vitamins absorbed through the skin rather than the gut. Dissolving under-the-tongue strips are next. It already has retail traction, with placements at Coachella, Revolve, and Laurel Supply in New York, collaborations with Crown Affair and Beauty Blender, and an Ulta deal in the works.

Very little carried over from the last company. Consumer packaged goods build value in discrete steps rather than the gradual climb of software, and none of his health tech investor relationships followed him into the category. What did follow him was the experience of getting OptionsMD out the door: how to find a market before the product exists, how to run a negotiation, and when to stop pushing.