Podcast
Critical Moments
Hosted by Mark Josephson · EN
Critical Moments is where we dive deep into the pivotal moments that define careers and lives. Hosted by Mark Josephson, a tech veteran with 30+ years of experience leading companies like Bitly and Castiron, this podcast isn’t just about business, it’s about the whole person. We explore how leaders navigate high-stakes decisions at work while balancing health, family, and personal life. With candid conversations, we’ll uncover the real stories behind the successes and struggles that shape the people who build the tech industry. Expect laughter, lessons, and a lot of honesty.
11episodes
Episodes
Newest firstAll episodes
What Liana Douillet Guzmán Couldn’t Unsee
Oct 500:36:20Tap to summarizeWhen Silicon Valley Bank collapsed, Folx Health had every dollar locked inside. CEO Liana Douillet Guzmán, 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
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Jacob Ross on Trusting Yourself and Building the Business You Can See
Sep 2900:37:42Tap to summarizeJacob 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 futures07:15 – PebblePost’s pitch and the “What kind of company is this?” question10:45 – Going to market: the failed-but-successful sales process14:25 – The realization: narrative isn’t enough, business reality matters18:00 – Strategy shift: from direct mail to full-funnel performance marketing23:45 – Launching CTV and realigning the team31:10 – What it means for employees to feel the vision36:20 – What CEOs can learn from this: trust yourself38:10 – The impact and memory of founder Lewis Gersh
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Never Get a “Real Job” Again: Sue Heilbronner on Losing a Role, Choosing Herself, and Selling Without Selling
Sep 900:42:02Tap to summarizeWhen a CEO tells you “I’ve lost confidence in you,” what do you do next? For Sue Heilbronner 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 (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
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When the World Stopped: Chris Grosso on Leading an IRL Business Through Covid
Aug 1700:32:22Tap to summarizeChris Grosso, CEO of Intersection, 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 homepage07:45 – Record-setting 2019 and early 2020 momentum14:20 – The first signs of trouble: Wuhan, Italy, and Seattle23:50 – Wartime leadership: employees, investors, transit authorities, advertisers36:10 – Mistakes, layoffs, and the pain of multiple cuts49:40 – Finding the light: vaccines, buses, and the road back
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David Siegel on Surviving the Impossible: The Day Meetup Went Online
Jul 2300:35:09Tap to summarizeWhen COVID hit in early 2020, Meetup’s entire model—bringing people together in person—was shattered. In this episode, Meetup CEO David Siegel 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.Timestamps00:41 — Why David almost didn’t tell this story03:15 — The dashboard that turned blood red06:42 — The mission vs. survival dilemma11:30 — Talking to 30 people in 24 hours14:50 — Launching a 2-day MVP against all odds19:15 — What organizers taught him about resilience23:45 — When engineers quit over mission conflict27:30 — Action bias, Churchill quotes, and how to know when it’s time
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Perfectly Enough: Jaclyn Fu’s Leap from Product Marketer to Purpose-Driven Founder
Jul 1600:31:53Tap to summarizeJaclyn Fu, cofounder of Pepper, shares the moment that changed everything: launching a bra company for small-chested women from her home office in Denver. In this episode, we walk through her accidental 13-day Kickstarter campaign, building with conviction, fundraising without VC, and scaling a global brand without ever compromising on her mission. It’s about joy, courage, and believing that you and your work are perfectly enough.Timestamps:00:00 — Intro: From Boulder dinner to bra startup04:10 — April 12, 2017: The launch that changed her life07:30 — A $10K goal, a wrong campaign setting, and urgency magic11:20 — How product marketing skills powered the Kickstarter14:50 — Deep vulnerability plus great storytelling equals community20:00 — Champagne and steak: Celebrating the first win24:45 — Why “you knew” matters more than market TAM28:40 — Lessons from bootstrapping: contractors, clarity, and cash33:10 — What she’s excited about now: going grassroots again36:20 — What she’s learned from the women she serves40:00 — “Perfectly enough”: the power of imperfection44:00 — Joy is the engine. Conviction is the fuel.
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You Need a Soulmate, Not Just a Cofounder: Paul Canetti on Building MAZ
Jul 800:36:24Tap to summarizeWhat does it take to find the right cofounder? In this episode of Critical Moments, Paul Canetti, founder of MAZ (acquired by PSG Equity), shares the improbable, global journey that led him to meet his technical cofounder through a cold LinkedIn message and why that connection changed everything.You’ll hear:(01:07) Why Paul’s most defining startup moments all come back to cofounders(03:06) Launching MagAppZine in the earliest days of the iOS App Store(05:57) The LinkedIn DM that rewrote the future of his company(10:25) Why being a futurist is essential for building real products(14:25) How to actually find a technical cofounder(25:26) What it feels like when your founding team just clicks(30:43) Why one great idea can wait a decade to be builtPaul breaks down what matters most when you’re starting from scratch and why skills are only part of the equation. If you’re trying to build something real, listen to this.🧠 Learn more at markjosephson.net📩 Feedback or guest ideas? Let me know.🎧 Subscribe and share if this resonated.
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Julie Samuels of Tech:NYC: The Power of Coming Back
Jul 100:26:32Tap to summarizeJulie Samuels, President and CEO of Tech:NYC of Tech:NYC, shares the moment she decided to return to the organization she built. After stepping away for a year, she came back pregnant with her third child and helped steer the tech community through the SVB collapse. She talks about burnout, clarity, growth, and what it takes to lead again with energy and purpose.Timestamps:06:25 – The origin and mission of Tech:NYC12:50 – The walk in Central Park that changed her mind20:10 – Burnout, pregnancy, and perspective27:30 – Leading through SVB and regaining trust36:40 – Empire AI, Decoded Futures, and where Tech:NYC is now
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Tapas for One: How Clara Ma Turned Burnout into a Booming Business
Jun 1600:32:08Tap to summarizeFounder and CEO of Ask a Chief of Staff, Clara Ma joins Mark to talk about the moment she walked away from a fast-paced startup career—and accidentally started a thriving business. This episode is about burnout, sabbaticals, second chances, and building with intention.We cover:(00:50) Clara’s burnout while working at OnDeck(08:30) The Cayman Islands trip that changed everything(14:15) How quitting without a plan became a superpower(21:10) Her “Tapas for One” moment in Spain—and what it taught her(30:45) Launching Ask a Chief of Staff without knowing it(37:00) What balance really looks like—and how she protects itWhether you’re a founder, a chief of staff, or just wondering what else might be possible, Clara’s story is a reminder: your life is now.👉 Learn more or suggest a guest at markjosephson.net
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99% Blocked—and Andrew Racine Had No Idea
May 18, 202500:41:18Tap to summarizeIn this episode of Critical Moments, Andrew Racine shares the terrifying story of how a slight chest tightness turned out to be a 99% blockage in his “widowmaker” artery. A high-performer, devoted dad, and Peloton regular, Andrew thought he was doing everything right—until his body refused to cooperate.This conversation isn’t just about heart health. It’s about listening to your instincts, understanding stress, and knowing when to stop pushing through. If you’re a high-achiever who thinks “it won’t happen to me,” this one’s for you.🩺 Heart disease | 🧠 Stress & performance | 🚴♂️ Fitness over 40 | 📉 Ignoring symptoms | 👨👩👧👦 Family, mortality & purposeTimestamps04:32 — Crushing work goals… but something feels off07:50 — The subtle signs: fatigue, breathlessness, tightness16:45 — The decision not to go to the ER (and why that almost cost him everything)33:18 — 99% blocked: The call that changed everything49:07 — Recovery, reflection, and the real takeaway: “Trust your Spidey sense”
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