What do you do when you haven’t yet reached scale, but market conditions have changed and runway is running out?

Tori Lecomte founded Sesh in 2019 to bring the power of therapist-led group therapy to consumers. Not coming from a healthcare or CEO background, but convinced the modality was dramatically underutilized, she focused on making sure she had market validation, launching a revenue generating in person direct to consumer marketplace, before adding virtual services, expanding to b2b sales, and then ultimately selling the company in 2023.

In this conversation, Tori talks about the strategic choices and challenges of building Sesh, the marketplace conundrum at the start, the strategic pivot from consumer to employer sales, navigating a crowded mental health market, and being painted as a point solution. Tori shares the challenges she faced raising her next round of funding, how partnership conversations shifted to become acquisitions discussions, and what it felt like to exit before Sesh had hit the scale and impact she had hoped for. She shares what she'd do differently with hindsight and practical tips for founders who find themselves considering their options.

Tori also gets candid about myth-busting one of the most pervasive startup tropes, the idea that your business is your baby, and how she navigated having her first child at a pivotal time for the company.

About Tori

Vittoria (Tori) Lecomte is the founder of Domestic Futures, a project exploring how technology, markets, and institutions are changing the way we form families. Previously, she founded Sesh, a mental health company acquired by Caraway. She began her career as a technology investment banker at Barclays and later joined Blockchain.com as an early employee. She was named to Forbes 30 Under 30 for Social Impact.

Presented by Aytza

What do you do when lawyers tell you the thing you're building probably isn't possible?

Demetri Karagas co-founded Thirty Madison in 2017 with no healthcare background, a consumer business playbook, and a conviction that a one-stop shop for telemedicine and prescriptions was obviously better for patients, even if the lawyers weren't sure it was possible. He and his cofounder had a vision for a platform of multiple deeply specialized brands of which “Project Samson” (the early working name for their flagship brand Keeps) was the first.

In this conversation, Demetri talks about early structural decisions, like which pieces of the value chain to own vs partner, why controlling that first patient touchpoint was worth a slower launch, and how Thirty Madison pioneered asynchronous telemedicine. Demetri opens up about the hubris trap after Keeps hit big, adding 20-30 people a week in early scaling days, and how they lost (and then regained) some of the rigor that made the first brand work.

Finally, he dives into being on both sides of M&A - acquiring two companies and then exiting via acquisition to get to scale. M&A can leapfrog years of organic growth, but integration is hard. Demetri shares how the team kept multiple paths open until the very end, including seriously considering another acquisition before deciding that selling was the right move.

About Demetri

Demetri Karagas is a New York City–based entrepreneur. He co-founded and led Thirty Madison, a digital health company that grew into one of the leading specialty care platforms in the United States. Founded in 2017, Thirty Madison served millions of patients through brands including Keeps, Nurx, and Cove before being acquired by Remedy Meds in 2025. Prior to Thirty Madison, Demetri founded Get Maid, an on-demand home services marketplace that was acquired by Homejoy. After Google acquired Homejoy, he spent a brief stint working on Search Ads before returning to startup life. Today, he's experimenting with new ideas across healthcare and consumer technology while trying to keep up with his 10-month-old son.

Presented by Aytza

Most founders get one shot at building something that matters. Glen Tullman has taken several, and he keeps going back for more.

In this conversation, Glen traces the through-line of a career spent trying to fix a healthcare system that, in his words, still runs 50 years behind every other industry. From the early days of building Livongo into a category-defining chronic care company, to reentering the startup space, the arc of his journey is less about any one company and more about making the healthcare system more affordable and accessible for all Americans.

Glen talks about what it looks like to lead at every stage, from building office furniture, rapid scaling, to IPO and beyond. He also shares the frameworks that have held across every chapter: make lists, measure what matters, attack ideas not people, and why not to invest in someone who has an exit strategy.

He talks about why he doesn't believe in work-life balance, instead focusing on working on things that matter and prioritizing family. And because Glen is Glen, he also built a 40,000-square-foot magic experience in Chicago to fulfill a childhood dream and bring people together.

About Glen Tullman

Glen Tullman is the Chief Executive Officer of Transcarent, the first comprehensive, consumer-directed health and care platform that makes it easy for people to access high-quality, affordable health and care. He is the former Executive Chairman, Chief Executive Officer, and Founder of Livongo Health. Glen led Livongo through the largest consumer digital health Initial Public Offering in history and the industry’s largest merger to date between Livongo and Teladoc Health.

A visionary leader and entrepreneur, Tullman previously ran two other public companies that changed the way health care is delivered: Allscripts, the leading provider of electronic prescribing, practice management, and electronic health records for physician practices and Enterprise Systems, the leading resource management systems for hospitals, which he also took public and then sold to McKesson/HBOC. Glen is also one of two Founding Partners at 7wireVentures, a leading healthtech venture fund. He is the author of On Our Terms: Empowering the New Health Consumer, in which he proposes new solutions to address the chronic condition epidemic facing our country. 

Presented by Aytza