At a recent StartUp Health Fireside Chat, Logan Plaster sat down with Drew Schiller, Chief Development Officer at ChartSpan and Co-founder of Validic, for one of the most candid conversations about exits the community has heard in a while.

Schiller co-founded Validic in 2010 and as CEO spent 15 years building it into a platform that connected more than 700 healthcare devices and apps for health systems, payers, and digital health companies. Earlier this year, ChartSpan acquired Validic, and Schiller now serves as Chief Development Officer and sits on its board.  But the story founders came to hear was not just the closing. It was how they got there.

Schiller started by pulling apart two things founders often treat as one. "Step one: build a company worth being acquired. That is really hard to do," he said, "and step two is actually getting acquired. It's actually also very difficult." 

The second step, he explained, depends on several things going right for a long time: the right stakeholders at the buyer staying engaged, the deal staying a top priority, the macroeconomic environment holding, and no black swan event showing up. That last condition almost never holds. "There's always something that either kills the deal or almost kills the deal, like, almost universally," he said. 

He knows this from experience. Validic was under letter of intent in early 2020 when COVID hit. The acquirer had physical locations that were forced to close, and a reorganization soon removed the executive whose strategy the deal depended on. A second opportunity with a large strategic buyer came in Q1 2022 and got through diligence to investment committee, where, Schiller recalled, "Everybody on the investment committee, including the CEO, said, 'Yes, we're doing this,'" before the buyer's CFO pulled the plug over what Schiller described as a materially adverse event on their side. The ChartSpan deal that finally closed nearly died, too, when what Schiller called the "SaaSpocalypse" hit in Q1, a moment "where all of a sudden the bottom fell out of SaaS companies," making it harder for the growth equity-backed buyer to finance the transaction. The deal was actually called off at one point before Schiller got it back on track.

Schiller was direct about the macro picture. He saw 2023 and 2024 as a genuinely bad time to sell, with depressed market comps across digital health. That is why Validic did not go back to market then. He believes the market is recovering now, but selectively. 

Buyers, in his view, are rewarding two kinds of companies: those with strong business fundamentals, and those with a credible AI-native story about how they will reimagine healthcare. A standard digital health company that is losing money and has no clear AI thesis is, as he put it, in "a really tough place to be." 

Asked what a founder should do two years before a planned exit, Schiller pushed back on the timeline itself. Two years, he said, is probably not long enough. In his experience, what gets a company acquired is relationships, and those take years to build (and are a fundamental part of StartUp Health membership). 

He got involved with the Consumer Technology Association early in Validic's history. He eventually chaired its health division and was also active with the eHealth Initiative, which later became Executives for Health Innovation. Those relationships produced customers, partners, and eventually M&A conversations. Even when a contact never becomes the buyer, having them in the room can create the competitive tension that strengthens a sale process. 

He also reminded founders that they belong at those tables. "Your strongest resource is your mind and your entrepreneurial curiosity," he said. Leaders at large companies bring resources, but startup executives bring the willingness to ask why things work the way they do. Over time, that visibility turns cold outreach into warm introductions. "You can reach out to somebody who knows somebody and it's a warm intro instead of a cold intro," he said.

On tactics, Schiller named three priorities for founders preparing for a sale. The first is expense discipline. Acquirers are scrutinizing burn more closely than they did a few years ago, and a credible path to EBITDA-positive or cash-flow-neutral operations now counts for a lot. The second is clean, audited financials, because every number will be tested. The third is a strong operating team. At Validic, the COO and CFO ran most of the diligence. 

He described a sale process as a three-legged stool: storytelling, financial diligence, and operational diligence. The founder-CEO owns the first leg. "As the founder CEO, your job really is the storytelling," he said. That means telling not only the company's story but also what the combined business could become, which sometimes means painting a vision the buyer hasn't seen yet. The other two legs need people who can carry them while the CEO keeps running the company. 

On AI, Schiller agreed that the market is hungry for AI-enabled services and that human services will stay essential for some time.  But he warned founders about a new temptation: using cheap, fast AI development to build everything in-house.

"My recommendation would be probably don't build a CRM using Claude," he said. The real question, in his view, is what business you are in. Every tool you build yourself, even with AI, is one you have to maintain, extend, and support. He called that a "hidden tax." He sees the same logic with customers who think they can use AI to build their own device integrations. They could have assigned engineers to that years ago and chose not to, because it pulled focus from their actual value proposition. 

"Best you can do with AI is catch up to where I am, and that's gonna still take you a long time and a lot of tokens," he said. His advice is to point AI at your core value proposition and your proprietary data, not at commodity software. 

The live session continued with an extended Q&A for StartUp Health members. That portion is not in the public video and podcast, but a few themes deserve a wider audience.

One founder asked whether a banker or broker is worth it. Schiller said Validic used an investment bank in each attempt, but every eventual acquirer was a relationship he had sourced himself. Bankers are still valuable for running a structured, deadline-driven process that makes corporate development teams commit instead of stringing founders along, and Validic deliberately "did not put any carve-outs in" its banker agreement "because we wanted them to work hard."

Another community member asked what it takes for clinicians to trust patient-generated data. Schiller said physician trust in wearable and consumer health data is "a lot stronger today than it was 10 years ago," recalling that the question used to be, "Why would I want this data?" The bigger barrier is reimbursement: health systems have little financial mechanism to justify integrating and reviewing that data, even though Validic brings data "into, like, Epic and Oracle Cerner clinical workflows, directly." On trust, he pointed to practical design choices: letting patients flag bad readings, prompting a re-test after a concerning result, and giving clinicians concise summaries instead of raw data.

A question about the value of contextual, non-clinical health data, such as diet, air quality, and home environment, led to one of the most sobering exchanges of the hour. Schiller argued that few players in U.S. healthcare are structurally rewarded for paying for long-term prevention. Health plans tend to optimize within the plan year, and health systems are largely paid for procedures. He suggested life insurers, who benefit when people live longer, may be the most naturally aligned buyers of that kind of data. 

When asked how he recovered after the collapsed deals, Schiller was unusually open. He described the first failure as genuine trauma that took roughly 18 months to work through, with help from a CEO coach, a therapist, his family, and, in his words, walking "many, many, many miles in the woods" with his dog. The pain, he said, came less from any damage to the business, which kept growing, than from losing the story he had told himself about how his career would unfold. His advice was to keep deal knowledge on "a need-to-know basis" (during the first deal, only his immediate team of "roughly maybe six people" knew) and to tell the team to keep building as if the deal might not happen.

He also talked about life after the exit. He described feeling "5,000 pounds lighter" the day after closing and is adjusting to being an employee again. He noted that the operational fluency founders build (knowing bookings, churn, cash, and every at-risk client by heart) turns out to be a valuable, portable skill in the boardroom. He also shared how Validic moved from two-week sprints to “Shape Up,” a method that uses six-week build cycles and a two-week cooldown. He credited it with aligning product and sales and earning client trust in delivery timelines.

Schiller's story is not a victory lap. It is a practical map for founders who are building companies meant to last in a market that is getting more demanding. The most durable advantages he described are deeply human ones: relationships built over years, a team that can carry diligence, the discipline to stay focused on your core value, and the resilience to keep going when a deal falls apart. As AI changes what is cheap to build, those advantages matter more, not less.

This post covers a portion of a live StartUp Health Fireside Chat. The video and podcast are an excerpt of the full session, and the live Q&A was exclusive to StartUp Health members. Join StartUp Health to attend live Fireside Chats, get in the room with investors and industry leaders, ask your own questions in real time, and start building your own relationships.