Critical Moments

When 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

Jaclyn 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.

What 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.

Julie 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

Founder 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

In 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”

How to Keep Calm When the Money’s Running Out — with John McCarthyFractional CFO John McCarthy shares how he helps CEOs face their most critical moments.When a CEO calls John McCarthy, it’s usually because something’s gone wrong—very wrong. As a fractional CFO, John specializes in showing up during financial emergencies, calming down panicked CEOs, and figuring out what’s really happening with the cash. In this episode of Critical Moments, we talk about those moments when payroll’s at risk, the Excel model’s broken, and trust in the numbers has disappeared. John shares how he works through these situations step-by-step, what typically goes wrong, and why most financial crises aren’t as bad as CEOs think—if you know how to approach them.Timestamps:00:00 – Intro: Born to talk about this03:45 – “The job is not to run out of cash.”07:20 – The first thing John does when the CEO panics12:50 – Common breakdowns between finance and the CEO17:10 – The forensic approach to fixing a broken model24:30 – Why trust between the CEO and CFO matters most

What happens when your values clash with your business model—and the market starts to move without you? Nick Francis, CEO and co-founder of Help Scout, faced that exact moment. In this episode, Nick shares how he made the bold decision to kill a pricing model that had driven over a decade of growth, and how he rebuilt the company from the inside out. From AI disruption and shifting customer behavior to boardroom tension and strategic reinvention, this is a raw, honest look at what it takes to bet the company and come out stronger.If you’re a founder, CEO, or operator facing hard truths—this one’s for you.Timestamps: • 02:10 – The moment everything changed: COVID, capital, and chaos in SaaS • 06:40 – “This is over”: When Nick saw the model breaking • 12:55 – Values vs. pricing: Why per-seat didn’t align anymore • 21:45 – The 3-month rule and building a usage-based model • 30:10 – Selling the change: customer pitches, board pushback, and conviction • 42:35 – Strategy ≠ execution: Rediscovering differentiation

Chris Gannett has had the kind of career that looks like a highlight reel—CMO of a major entertainment company, advisor to global brands like Oreo and Dr Pepper, strategic roles with icons like Muhammad Ali and Elvis Presley, and large-scale activations for brands like Pokémon GO. He’s worked in music, media, marketing, and tech, building, growing, and reinventing companies along the way.But beneath the surface was a growing misalignment between his ambition and his identity.In this episode of Critical Moments, Chris shares the wake-up calls that made him rethink everything—from missing his twins’ first birthday for a Hollywood dinner to losing his father at the start of the pandemic. He talks openly about the toll of white-knuckling an executive identity, the slow road to self-awareness, and what it really takes to rewrite your story.This conversation is about resilience, letting go of control, and the power of deciding that your job doesn’t define you.Timestamps:00:00 – Friendly chaos, intros, and Hollywood CMO life07:30 – The moment he missed: his kids’ first birthday16:45 – Living out of sync: when identity and ambition drift apart25:10 – COVID, loss, and learning to let go of control39:30 – Reinvention, resilience, and the work of listening51:15 – Coaching, clarity, and rewriting your story🎧 Listen now and subscribe to Critical Moments for honest conversations with leaders navigating real change.

When the company you built is no longer yours—and the next chapter isn’t obvious—what happens next?In this episode of Critical Moments, I talk to Nick Gould, a founder turned executive turned coach, about what it really feels like to leave behind the work that defined you for decades. Nick shares how he built Catalyst Group, sold it twice, and then found himself unexpectedly adrift. What followed wasn’t a clean next step—it was five months of uncertainty, reflection, and doing the deep personal work to figure out who he was without the job title.This one’s for anyone navigating a transition—or supporting someone who is.🔑 Key moments and takeaways: • (00:02:00) Reconnecting after 15+ years: life, kids, Brooklyn, and Basquiat • (00:09:30) Building Catalyst Group and the early days of UX • (00:17:45) Two exits, one after the other—and then: the question of “what now?” • (00:21:50) When your identity is your work: the shock of losing the tether • (00:28:30) Finding a new direction by going back to first principles • (00:34:00) Product leadership, presence, and translating founder skills into new roles • (00:41:15) From career transition to coaching: why the door stayed open • (00:54:00) Three lessons for leaders facing uncertaintyWhether you’re a CEO, founder, or just in between chapters, this conversation is a reminder that reinvention takes time—and it’s worth it.