Critical Moments

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."

In this episode of Critical Moments, Mark Josephson interviews Emmanuelle Skala, a seasoned executive who shares a pivotal leadership moment that changed her career trajectory. Facing feedback from her CEO that she was “not well-liked,” Emmanuelle reflects on the challenges of balancing results with relationship-building in high-stakes leadership roles. Key themes include: • The power of radical candor in executive feedback. • Transitioning from a results-driven mindset to a relationship-focused leadership style. • Practical lessons for CEOs on fostering authentic connections while driving growth. This conversation is packed with actionable insights for CEOs, startup founders, and senior leaders looking to enhance their self-awareness, improve team dynamics, and drive long-term success. Key Moments: • [00:01:53] Emmanuelle’s background and global leadership role. • [05:22:44] The career-altering feedback from her CEO. • [10:07:75] Reflecting on leadership style and its impact. • [18:33:59] Insights on radical candor and its role in growth. • [22:27:48] Building authentic relationships as a leader. • [28:43:97] Emmanuelle’s three takeaways for CEOs and leaders.

In this episode of Critical Moments, host Mark Josephson talks with Cristina Miller, former COO of Goldbelly, about a critical moment in her career that tested her resilience, leadership, and problem-solving skills. Goldbelly, a rapidly growing food marketplace, faced a logistical nightmare during the peak of the holiday season: 70,000 packages at risk of not being delivered due to shipping delays caused by COVID-19 vaccine distribution. Cristina shares the high-stakes decisions, the scramble to escalate the issue with UPS, and the leadership lessons she took away from navigating this career-defining challenge. Key timestamps and insights include: • [01:06] Cristina introduces Goldbelly and her role in scaling the company during the pandemic. • [02:17] The meteoric rise: 5–6x sales growth as Goldbelly became a lifeline for food makers. • [07:04] The crisis unfolds: A phone call from UPS with devastating news about holiday shipments. • [10:53] High-stakes logistics: The challenge of delivering perishable goods at massive scale. • [16:00] Critical moment: Strategizing solutions while battling time constraints. • [22:40] Escalating the issue: Reaching UPS CEO Carol Tomé to resolve the crisis. • [31:55] The outcome: How leadership, collaboration, and swift action mitigated the disaster. • [35:43] Leadership takeaways: Staying calm, escalating effectively, and delivering bad news with a plan. • [38:00] The value of relationships: Building goodwill with partners for when you need them most. This episode offers a rare behind-the-scenes look at how leaders tackle unexpected challenges, make tough calls, and ensure success in the face of adversity. Cristina’s insights are invaluable for anyone building businesses, managing teams, or navigating high-pressure moments. Listen now on Apple Podcasts or Spotify and join us for real stories from leaders making critical decisions that shape careers and companies.

In this inaugural episode of Critical Moments, Mark Josephson sits down with Matt Blumberg, the former CEO of Return Path and current Executive Chairman at Bolster, to discuss one of the most defining moments of his career: the near-sale of his company that fell apart at the eleventh hour.Matt takes us behind the scenes of a nine-figure deal that was so close to closing, the champagne and cupcakes were already delivered to offices worldwide. But a single phone call changed everything, forcing him to navigate the fallout, rebuild his team, and learn invaluable lessons about leadership, resilience, and the art of the deal.Key highlights include: • [03:12] The critical moment: Almost selling a 17-year-old SaaS company, only to have the deal fall through at the last minute. • [07:01] “I can’t believe I’m making this call”: The phone call that stopped the deal in its tracks. • [10:12] The immediate aftermath: Matt’s physical reaction and the challenge of informing his team, board, and family. • [13:44] Salvaging what’s possible: Pivoting to secure a strategic investment at the valuation agreed upon in the failed deal. • [25:48] Rebuilding and recovery: Lessons learned, team departures, and selling the company two years later for a lower valuation. • [32:18] Retrospectives and pre-mortems: How structured reflections and anticipating risks can help leaders avoid repeating mistakes. • [33:50] Key takeaways: The importance of meeting decision-makers, identifying potential deal-killers, and fostering a bias for action.This candid and insightful conversation captures the highs and lows of leadership in a way that’s relatable, human, and rich with actionable lessons for anyone building a company or leading through uncertainty.Listen now on Apple Podcasts or Spotify, and join us for a deep dive into the critical moments that shape careers and companies.

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.