In this episode, Mallory Contois, VP of Growth at Maven and founder of The Old Girls Club, traces her path from hypergrowth operator to community builder. She reflects on the “up, down, up” rhythm of her career, from Pinterest’s rocket ship years to rediscovering fit after leaving Metafy, and shares what she’s learned about ego, feedback, and identity along the way. Mallory opens up about being diagnosed with ADHD as an adult and how that reframed her communication, leadership, and approach to feedback. She explains why no one is an “A-player everywhere,” how environment shapes performance, and what it takes to design work that truly fits your strengths. Now leading growth at Maven while scaling a 2,000-member community, Mallory gets practical about following momentum, hiring for energy, and coaching the edges. She also reframes mentorship, arguing that small, intentional peer communities can be more powerful than chasing a single mentor, and offers practical advice for giving and receiving feedback without losing your voice.

In this episode, Ryan McCready, content leader turned Principal Content Engineer at Demostack, opens up about the moments that shaped his path: hacking distribution in the early “monoculture SEO” days, sharpening his voice through roles at Foundation, Reforge, and Whimsical, and facing his first layoff. He shares candid stories about creator burnout after viral teardowns, being the last marketer standing after cuts, and the gut punch of being told he hadn’t delivered on a role that had completely changed. When the market went quiet, Ryan turned the setback into a story on LinkedIn, igniting a thousand DMs, weeks of interviews, and a fresh sense of momentum. Now, as a builder and editor who treats vulnerability like a career asset, Ryan talks about measuring success in relationships, not just metrics, documenting your receipts, keeping your voice, and sending that DM. He breaks down the unglamorous parts of leadership: giving and receiving hard feedback, guarding against plagiarism, and aligning work with products that actually have staying power, while showing how practical AI and automation can clear the busywork so you can create with intention.

In this episode, Kirk Reynolds, seasoned founder and now the creator of Wilder Retreats, opens up about the hardest conversations of his career. From telling his 55-person team that he was selling the company without sharing the real reason, to navigating the identity crisis that came when the acquirer shut it down, Kirk reflects on what it means to lead with honesty, even when fear and burnout make it tempting to hide. He also shares how blunt feedback about being a “people pleaser” reshaped the way he manages, and why processing failure and loss is just as important as chasing growth. This is a conversation about leadership, identity, and the courage it takes to be fully yourself when the stakes are high.

In this episode, Heidi Gibson, product and growth leader with stints at companies like GoDaddy, Typeform, and Bill.com, reflects on the pivotal lessons from her unconventional career path. From welding nuclear submarines to becoming VP of Product, Heidi shares how resilience, feedback, and self-awareness shaped her leadership journey. Heidi opens up about the realities of imposter syndrome, learning to present to executives, and navigating tough interpersonal conflicts as a manager, all while building a reputation as a trusted, people-first leader.

In this episode, Devin Reed, one of the leading voices in content and marketing, opens up about the defining moments that shaped his career—from growing up between two very different cultures in Sacramento to building a name for himself at Eventbrite, Gong, and Clari before stepping out on his own. He shares candid stories of career pivots, from giving up on his dream of teaching to unexpectedly landing in tech sales, and later realizing his sweet spot in content marketing. Devin reflects on the sting of being graded a “seven” at a company that recruited him aggressively, the intimidation of being told he wasn’t qualified for his role at just 25, and the burnout he faced after tying too much of his worth to productivity. Now as a founder, creator, and dad, he talks about learning to measure success not in metrics but in moments—balancing ambition with presence, and re-wiring what it means to “win” in both business and life.

In this episode, Justin Bauer, former Chief Product Officer at Amplitude and now one of the most sought-after product advisors in AI, talks about the pivotal career moments that shaped his leadership style. From betting everything on a tiny startup with 13 people to navigating layoffs and leveling conversations, Justin shares how he learned to lead with clarity, humility, and courage. He also reflects on what it takes to thrive in a high-growth environment — and how to reinvent yourself every 18 months to stay relevant. This is a conversation about ambition, emotional resilience, and how to earn trust when the stakes are high.

In this episode, Rana Mumtaz, Product Growth Leader, reflects on the defining moments that shaped her personal and professional identity—from quietly adapting to American culture as a soft-spoken engineering student to building products at the New York Stock Exchange and navigating executive rooms as a banking outsider. She opens up about career pivots that required unshakable self-belief, including her leap from civil engineering to software, and the moment she realized her leadership potential didn’t need to follow anyone else’s blueprint. Rana shares how difficult conversations, strategic missteps, and cultural friction all played a role in helping her find her voice and shape her path.

In this episode, Joanna Lord, global CMO, board advisor, and multi-time tech executive, reflects on the moments that forced her to grow the most. She shares how being passed over for a promotion after a colleague threatened to quit cracked open her entire leadership style, as well as the AMA that sent her into a full-blown panic attack just days into a new global CMO role. These moments became turning points, pushing her to shift from a self-focused high performer to a more collaborative and self-aware leader. Joanna also talks about impostor syndrome, recovering from public missteps, and learning to separate her identity from her job title. This isn’t just a conversation about leadership — it’s about resilience, reinvention, and what it really means to grow up in your career.

In this episode, Raj Singh, multi-time founder and current VP of Product at Mozilla, opens up about the moments that nearly unraveled his career. From getting called into HR over a side hustle to walking away from a startup after being unexpectedly leveled, Raj shares what it’s like to navigate the highs and lows of building without losing your identity. He walks us through multiple pivots, including the time he turned down a seven-figure exit and the brutal leadership decision that nearly cost him a co-founder. Raj doesn’t just talk strategy, he gets into the emotional rollercoaster of founding: the resentment, the rejections, and the real mental toll of being the one expected to have all the answers.

In this episode, Gururaj Pandurangi, three-time founder and CEO of ThriveStack, opens up about the near-death moments, pivots, and internal reckonings that shaped his entrepreneurial journey. From growing up in Mumbai with dreams of becoming a scientist to leading multi-million dollar product bets at startups backed by Microsoft and Deloitte, Guru shares what it really takes to build when the vision keeps shifting and the runway keeps shrinking. He walks us through two moments when his companies nearly ran out of money and the uncomfortable decisions that pulled them back from the edge. From flipping into consulting just to survive to gambling everything on a risky conference booth, Guru doesn’t just talk strategy. He talks about fear, team trust, and the mental load of being the one who has to believe before anyone else can.

Can you be too nice to lead? In this episode, Michael Leibovich, GM and Head of Growth at Adobe, shares the career pivots, personal awakenings, and leadership lessons that shaped his unconventional journey from touring musician to executive. Michael opens up about getting fired, receiving feedback that questioned his approach to leadership, and learning how to balance empathy with outcomes. From scaling growth teams at Vimeo, Mindbody, AppFolio, and Abstract to navigating the emotional weight of letting someone go, Michael brings clarity to the messy, human side of leadership. We explore how feedback becomes identity-shaping, what it means to truly “drive clarity” in a role, and why building a career is more about learning from missteps than chasing perfection.

What happens when your dream job starts crushing your values instead of honoring them? In this episode, Steph Pennell—founder of The Event Critic and former marketing leader—opens up about the moments that pushed her to reevaluate everything. From getting a shocking piece of feedback about wearing red lipstick to quitting a high-profile job with no backup plan, Steph shares what it takes to walk away from misalignment and rebuild your career around who you actually are. We talk about the events industry, the power of self-awareness, and how manifestation, ADHD diagnosis, and human design helped her take back control. Whether you’ve ever felt like you’re “too much” or you’re navigating burnout behind the scenes, this one’s for you.

What happens when you finally land the leadership role you’ve been working toward—only to realize it’s not what you imagined? In this episode, Shannon Curran—former VP of Marketing at MadKudu and now founder of SSC Consulting—opens up about the real moments that shaped her career. From growing up as a risk-averse high achiever to becoming a solopreneur trusted by founders, Shannon shares the feedback that shook her, the environments that helped her grow, and the human-first leadership lessons she learned the hard way. We unpack why cultural fit isn’t fluff, how to build trust in hard conversations, and why you don’t need to have all the answers to be a great leader. Whether you're in-house, managing a team, or building something of your own, this conversation offers something real.

What makes someone walk away from a PhD, a career in law, and the startup that made them? In this episode, I sit down with Else van der Berg—a former head of product turned solopreneur—to unpack the hard-earned lessons from the burnout that nearly broke her. Else shares how working 80-hour weeks and tying her identity to performance pushed her to the brink—and what changed afterward. We talk about how startup culture, pressure to “always be on,” and even toxic leadership can distort your sense of success. Else doesn’t just reflect on the crash—she offers a clear, honest roadmap for building back stronger, with boundaries and intention.

Devin Bramhall has been a VP of marketing, a CEO, a fractional CMO, and now an author, but none of that came without falling on her face multiple times. In this episode, Devin opens up about the mistakes that got her fired (twice), the time she unknowingly helped commit financial fraud, and the zero-tolerance plagiarism incident that backfired in the worst way. Through all of it, she’s held onto her belief that everything from leadership to content strategy is made up, and that’s exactly why you can rewrite the rules. Devin shares what it means to lead with bravery and curiosity, how ambition nearly derailed her career, and why making space for nuance, not just kindness, is the real growth path for leaders.

What makes someone leave a high-paying product marketing role just before a massive acquisition? In this episode, I sit down with Jason Oakley—founder of Productive PMM and co-founder of Demo Dash—to unpack the bold career decisions that shaped his journey in tech. From leading product marketing at a hypergrowth startup to becoming a full-time creator and consultant, Jason shares the systems, mindset shifts, and lessons that helped him bet on himself.

Erin Balsa’s journey from teaching troubled teens to becoming a solopreneur in content marketing is anything but conventional. After a rewarding but challenging career in education, Erin found herself pivoting to tech marketing, working her way up to director roles at companies like Predictive Index. But the leap from the corporate world to running her own business wasn’t without its hurdles.

Ty Magnin, former marketing leader at Appcues and UiPath, now CEO at Animalz, made a mistake that could’ve ended his career. While leading a team at UiPath, he accidentally uploaded a private doc that outlined a power shift — and the wrong person saw it. What followed was a firestorm of Slack messages, a panic spiral, and a career-defining moment of humility and growth.

Elena Luneva, VP of Product at GoFundMe, opens up about the hard-earned lessons that shaped her leadership journey—from navigating layoffs early in her career to building a business unit from scratch at Nextdoor.

April Dunford, author and globally recognized expert on product positioning, reflects on her unconventional journey from aspiring doctor to tech executive to in-demand consultant. In this episode, she shares what made her finally walk away from VP marketing roles, how she reinvented her career in her late 40s, and why teaching, not advising, is at the heart of her business today.