Michelle Davey built Wheel from a bootstrapped clinician-matching service into the infrastructure behind virtual-first care for some of the largest healthcare enterprises in the country like Amazon Clinic.

In this conversation, she gets honest about what that evolution actually looked like. She talks about walking into a board meeting with the investor hockey stick chart and telling them they needed to change course despite it. About pivoting from SMBs to enterprise when every instinct said keep the revenue coming. About acquiring GoodRx's care platform and integrating it in only nine months. About over-hiring in 2021 and the dark days that followed when she had to unwind it. She also talks about her actual pajama time: blocking mornings for reading, then picking back up after the kids go to bed to catch up on what's happening in the market.

As Michelle puts it: "A lot of people get into being a founder because it seems glamorous. It is not."

In this episode:

• From Enzyme to Wheel: the three horizons of building virtual-first care infrastructure
• The board meeting where she stopped chasing SMB growth
• Acquiring GoodRx's care platform and building an EMR she said she'd never build
• Horizon 3: An AI-native platform powering programs like weight management, menopause, and longevity
• Her biggest mistake: over-hiring in 2021 and the layoffs that followed
• Hot take: "GLP-1s are going to be more disruptive to healthcare than AI"
• The signal she's watching: stagnation in large payer market values

About Michelle Davey

Michelle Davey is the CEO and founder of Wheel, the infrastructure platform powering virtual-first care for enterprise healthcare companies. She started the company in 2018 after spending 15 years undiagnosed with an autoimmune condition in rural Texas. That experience drove her into healthcare, but the perverse incentives drove her out and into tech, where she built her career across startups and gig economy marketplaces before finding her way back to telehealth in 2016. Today, Wheel’s AI-native Horizon platform is on track to power 3 to 4 million patient visits this year for enterprises including retailers, pharmaceutical companies, and digital health brands.

Presented by Aytza

Taylor Justice spent 13 years building Unite Us from a veteran services startup into the infrastructure connecting healthcare, government, and community organizations across the country. In this conversation, he gets honest about what that actually looked like.

He talks about the first thing they built being wrong. The investor who told him healthcare was a mistake, then wrote back a year later to say he was wrong.

He also talks about the reality of scaling fast. Tripling headcount. Two acquisitions in 60 days. And what it took to stay the course when everything is moving at once.

As Justice puts it: “This sh*t is hard. And you definitely cry sometimes."

In this episode:

• Building for veterans, then pivoting into healthcare before knowing the landscape
• The first product they built (and why it was wrong)
• Realities of scaling fast: 300 to 900 people, two acquisitions, and trying to stay focused
• 12 years with a co-founder, and what it's like now that he's gone
• Myth bust: "Stealth mode is the biggest waste of time"

Taylor Justice

Taylor Justice is the CEO and co-founder of Unite Us, a software company connecting healthcare, government, and community organizations to coordinate care around health-related non-medical needs like food, housing, and transportation. A former U.S. Army infantry officer, Taylor was medically discharged and built Unite Us out of his own experience navigating the VA system and the gaps he saw for veterans without a network. Thirteen years later, Unite Us operates throughout the United States and has raised over $250 million to transform how human services are delivered.

Jen Goldsack has spent six and a half years building the Digital Medicine Society (DiMe) into a trusted voice for healthcare's digital transformation. In this conversation, she shares the inflection points that shaped the organization. And the real story behind them. Like the time a family office offered $4 million if DiMe would pivot to focus only on cancer. She said no. Then sat on the floor crying with her dog, knowing she'd just made everything harder. Or the org structure she championed for two years that wasn't working. And the courage it took to acknowledge it and rebuild. This year, she's been navigating all of it while fighting late-stage colon cancer. She talks about the brutal self-talk that preceded her diagnosis, what being a patient has taught her about the system she's trying to fix, and why the work feels more urgent than ever.

In this episode:

• Turning down $4M to protect DiMe's positioning as "expert generalists"
• The org structure shortcomings she wishes she'd caught sooner
• What it's like to navigate the healthcare system as a patient after 20 years working in it
• Hot take: Why longevity tech investment is "incredibly gratuitous"
• The signal she's watching: direct-to-patient pharma pathways

About Jen:

Jen Goldsack founded and leads DiMe, a nonprofit working to ensure digital technologies actually improve health, healthcare, and research. Her path to healthcare leadership started unexpectedly. She landed in the field during the 2008 financial crisis after competing in the Beijing Olympics as an elite athlete. Before DiMe, she built experience across two digital health startups (one successful exit), led digital initiatives at a Duke-FDA partnership, and conducted research at Penn. Today she sits on the boards of the Coalition for Health AI and Sage Bionetworks, and contributes to the National Academies' Roundtable on Genomics and Precision Health. She holds three graduate degrees: chemistry from Oxford, history and sociology of medicine from Penn, and an MBA from George Washington. Beyond her professional credentials, Jen is a Pan American Games champion, former world record holder, and World Championship silver medalist.

Resources & Links:

Digital Medicine Society (DiMe) - https://dimesociety.org/

Follow Jen Goldstack - https://www.linkedin.com/in/jgoldsack

Presented by Aytza

https://www.aytza.com/