David Siegel on Surviving the Impossible: The Day Meetup Went Online

What Liana Douillet Guzmán Couldn’t Unsee

When Silicon Valley Bank collapsed, Folx Health [https://www.folxhealth.com/] had every dollar locked inside. CEO Liana Douillet Guzmán [https://www.linkedin.com/in/lianaguzman/], just a year into her first CEO role, spent the weekend running scenarios on how to make payroll, protect patient care, and keep the business alive. By Sunday, the government announced all deposits were safe. But that wasn’t the relief she expected. It was the moment she saw her business clearly for the first time, and she couldn’t unsee it. In this episode of Critical Moments, Mark Josephson and Liana Douillet Guzmán talk about: * (00:03:00) The call that changed everything * (00:08:40) How Folx Health prepared for the worst * (00:15:10) The moment the crisis ended but clarity began * (00:23:00) Making the hard call to cut 20 percent of the team * (00:34:30) The difference between transparency and authenticity * (00:44:00) Standing in your decisions even when it hurts

Jacob Ross on Trusting Yourself and Building the Business You Can See

Jacob Ross is the CEO of PebblePost, a performance marketing company that pioneered programmatic direct mail. In this episode, Jacob shares the critical moment in 2021 when PebblePost tested the market for a sale and what he learned about investor signals, category perception, and the gap between a good business and a great opportunity. The decision not to sell turned into a major strategic pivot that would define the company’s next chapter: launching a CTV product and redefining their identity beyond direct mail. 🎯 Keywords: PebblePost, programmatic direct mail, CTV, performance marketing, investor relations, strategic pivots, founder transition, CEO coaching ⏱️ Timestamps: 00:00 – Jacob joins from the Upper West Side (and Orwashers) 03:10 – Life update: twins, camp, and nomadic futures 07:15 – PebblePost’s pitch and the “What kind of company is this?” question 10:45 – Going to market: the failed-but-successful sales process 14:25 – The realization: narrative isn’t enough, business reality matters 18:00 – Strategy shift: from direct mail to full-funnel performance marketing 23:45 – Launching CTV and realigning the team 31:10 – What it means for employees to feel the vision 36:20 – What CEOs can learn from this: trust yourself 38:10 – The impact and memory of founder Lewis Gersh

Never Get a “Real Job” Again: Sue Heilbronner on Losing a Role, Choosing Herself, and Selling Without Selling

When a CEO tells you “I’ve lost confidence in you,” what do you do next? For Sue Heilbronner [https://www.heysue.com/] that email triggered a choice: walk out with the box and never take a “real job” again. In this conversation we get into conscious leadership, radical candor that lands with love, and the practical way Sue turned “pick your brain” coffees into a coaching business and a decade of momentum. We also highlight Sue’s new book Never Ask for the Sale [https://www.heysue.com/never-ask-for-the-sale] (out now). It’s a playbook for founders, solopreneurs, and anyone who wants to grow a business without cringey selling. The core concept: passionate ambivalence -- show up fully committed, but without attachment to who joins you. That honesty is magnetic. Timestamps: • 00:00 — Why “friends and family” is the wrong opener (and yes, I butchered tenterhooks—easter egg!) • 05:10 — The Sunday night email: “I’ve lost confidence in you” • 13:40 — The real turn: deciding to never take a “real job” again • 22:15 — Conscious leadership from autopilot to choice • 32:30 — From $95 coffees to a real practice and pricing truth • 41:55 — Book spotlight: Never Ask for the Sale and “passionate ambivalence” • 49:20 — Why alignment with what lights you up is the only path forward

When the World Stopped: Chris Grosso on Leading an IRL Business Through Covid

Chris Grosso [https://www.linkedin.com/in/cjgrosso/], CEO of Intersection [https://www.intersection.com/], shares what it was like to run an out-of-home advertising company when the world suddenly went indoors. In February 2020, his team was riding record growth. By March, revenues had fallen 75% overnight. Chris opens up about wartime leadership, negotiating with cities and transit authorities, keeping essential workers safe, and the lessons he’ll carry forever about communication, contingency planning, and decisive action. Timestamps: * 00:00 – Introduction: AOL days and the power of the homepage * 07:45 – Record-setting 2019 and early 2020 momentum * 14:20 – The first signs of trouble: Wuhan, Italy, and Seattle * 23:50 – Wartime leadership: employees, investors, transit authorities, advertisers * 36:10 – Mistakes, layoffs, and the pain of multiple cuts * 49:40 – Finding the light: vaccines, buses, and the road back

David Siegel on Surviving the Impossible: The Day Meetup Went Online

When COVID hit in early 2020, Meetup’s entire model—bringing people together in person—was shattered. In this episode, Meetup [https://www.meetup.com] CEO David Siegel [https://www.linkedin.com/in/davidmsiegel/] shares the critical moment when he had to decide: stick to the mission or adapt to survive. Hear how he made the call to bring Meetup online in just two days, what he learned about leadership and urgency, and why 80% of his organizers stayed, even when everything changed. Timestamps 00:41 — Why David almost didn’t tell this story 03:15 — The dashboard that turned blood red 06:42 — The mission vs. survival dilemma 11:30 — Talking to 30 people in 24 hours 14:50 — Launching a 2-day MVP against all odds 19:15 — What organizers taught him about resilience 23:45 — When engineers quit over mission conflict 27:30 — Action bias, Churchill quotes, and how to know when it’s time