Critical Moments

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.

Some life and career-defining moments hit like a knockout punch.Kara Weber stepped into her first President role at a high-flying, VC-backed startup, ready to build something huge. Then came March 2020—and everything changed.In this episode of Critical Moments, Kara shares:✅ How a college soccer rejection taught her resilience and shaped her leadership✅ The gut-wrenching pandemic pivot that forced her to rethink everything✅ How she led a team through uncertainty and layoffs while staying open to new ideas✅ The radical shift that led to a successful exit instead of a collapseSometimes opportunity knocks lightly. Other times, it knocks you down. Kara’s story is about getting back up and creating something even better.[00:02] – Kara’s background and early internet days[01:24] – The career-defining moment she almost didn’t choose[06:27] – How a soccer setback led to her biggest college achievement[07:15] – Stepping into her first President role at a high-growth startup[14:22] – The pandemic hits—and suddenly, the entire strategy is gone[20:46] – Leading through uncertainty, layoffs, and radical change[33:37] – The unexpected pivot: Rethinking IP, fandom, and blockchain[42:07] – The company sells to Dapper Labs—an exit shaped by innovation[50:25] – Kara’s biggest leadership lessons from crisis to opportunity

Imagine walking into your first day as CEO, ready to lead—only to find out an hour later that your entire workforce is unionizing. That’s exactly what happened to Aziz Hasan at Kickstarter. In this episode of Critical Moments, Aziz shares the whirlwind of stepping into the CEO role with no transition, navigating one of the first tech company unionizations, and leading with listening, empathy, and presence instead of panic. • [00:54] Aziz’s background in product & design before becoming CEO • [01:49] How Kickstarter’s CEO transition unfolded in real-time • [06:13] Day one: The email goes out, and everything changes • [08:46] A second email—Kickstarter’s employees announce their plans to unionize • [11:25] The executive team’s reaction (and why panic isn’t a strategy) • [14:49] Why Aziz didn’t react quickly—and why that was the right move • [25:35] The challenge of a union framework in a mission-driven, PBC startup • [29:42] His official stance: Not anti-union, but skeptical of the impact • [39:43] The final vote—and what came next Aziz’s story is a masterclass in first-time CEO leadership, navigating crises, and making tough calls under pressure.

In this engaging discussion, Dave Morgan, a three-time entrepreneur and CEO of SimulMedia, shares his journey from a Pennsylvania coal town to the forefront of ad tech. He reveals the moment he decided to quit his job without a plan, emphasizing the risk of 'burning the boats.' Dave discusses how he envisioned the internet's potential before it took off and the art of effective storytelling. He stresses the importance of open-mindedness, relationship-building, and trusting your instincts in entrepreneurship, offering insights for anyone looking to take big bets.

Some career moves are planned. Others show up unannounced. Michelle Benfer wasn’t looking for a job when a recruiter called about an operating partner role in private equity. She had the job—leading revenue for a billion-dollar public company with 500+ people on her team. But something about the opportunity made her pause. In this episode of Critical Moments, Michelle shares: ✅ How she overcame imposter syndrome to take bigger roles than she ever imagined ✅ Why mentorship and outside perspective helped her weigh a major career decision ✅ How intellectual curiosity—not just compensation—guided her next move ✅ The exact moment she knew she was going to say yes Key Moments: [00:01] - Michelle’s background and career trajectory [01:09] - The unexpected recruiter call [03:00] - Facing imposter syndrome—even after landing a dream job [08:00] - How mentorship and outside advice shaped her decision [16:35] - The moment she knew she was taking the job

In this episode of Critical Moments, Mark Josephson sits down with Claudia Reuter, managing director at Yale Ventures’ Roberts Innovation Fund, to discuss a pivotal moment in her journey as a startup founder. Claudia shares candid insights into building a business while raising a family, navigating funding challenges, and the invaluable lessons she learned along the way. Key Topics: • Transitioning from a stay-at-home mom to a startup founder. • The emotional rollercoaster of securing a term sheet (07:30). • Handling a “very vexing issue” and managing expectations (10:10). • Balancing entrepreneurship with family life (14:10). • The value of perspective and pragmatism in leadership (20:46). • Lessons learned: Why funding isn’t always the answer (16:20). • Advice for entrepreneurs on resilience and focus (24:10).

In this episode of Critical Moments, Mark sits down with Josh March and Kasia Gora, co-founders of Sci-Fi Foods, a groundbreaking cultivated meat startup. They discuss their journey, from raising $45 million to create a better future for meat production to the critical moments leading to the company’s shutdown. Mark dives into their candid post-mortem on shutting down a startup with integrity and the lessons they’ve documented in Graceful Exit. Listen as Josh and Kasia reflect on market collapse, the tension between optimism and realism, and how honest communication and leadership paved the way for an impactful ending. Key Moments: • [00:47] Sci-Fi Foods’ origin story and mission. • [07:00] Raising $45M and the evolution of cultivated meat. • [11:20] Realizing market challenges and pivoting strategies. • [17:33] Receiving the critical email and the decision to shut down. • [22:50] Managing employees, investors, and creditors with grace. • [31:57] How Sci-Fi Foods’ IP is shaping the future of cultivated meat startups. • [38:02] Lessons in leadership: vulnerability, communication, and normalizing failure. Join us for a raw and inspiring conversation about leadership, resilience, and the art of ending well. Read their guide "How to Fail Well."