In this episode, Luke Wallace, founder-turned-fractional growth leader and former Chief Growth Officer at Zipline Education, opens up about the moment high-visibility mistakes hit customers and forced him to rebuild his operating system. He shares the CEO feedback that drew a line between being nice and being kind, why he chose to hire an executive coach instead of switching jobs, and how he moved from heroic execution to scalable systems that don’t break under pressure.Luke talks about over-communicating up and across with data, rebuilding trust after public misses, and setting binary outcomes that make expectations unambiguous. He also gets tactical on giving direct feedback without becoming a jerk, navigating team changes when a beloved generalist no longer fits the stage, running customer interviews to unlock stalled growth, and managing imposter syndrome as the stakes rise.In this conversation, you’ll learn:How to turn painful, public mistakes into long-term fuel for resilience, credibility, and trust.How to use systems, documentation, and managing-up rituals to scale beyond “hero mode.”How to build a support loop (clear feedback, mentors, and customer interviews) to stay grounded and effective.Things to listen for:(00:00) Intro(02:00) Luke’s early dream of becoming a pilot(03:22) Into tech via school IT program(05:00) Startup wins, scrappy realities(09:15) Thank you to our sponsor, Navattic(12:23) Direct feedback versus being nice(23:54) Building a data-backed recommendation(24:27) Handling high-stakes leadership talks(25:01) Working through imposter syndrome(27:19) Systems for scale over heroics(30:19) Why Luke hired an executive coach(34:42) The hardest conversations as a manager(36:45) When the team and role evolve(40:00) Giving clear, actionable feedback(40:32) One-to-one coaching offer from Andrew(43:20) Lessons learned from real failures(44:26) Customer interviews as the unlock(46:34) Key takeaways and ways to connectA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Luke: https://www.linkedin.com/in/lukewallace805/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coachingJoin Growth OS: https://deliveringvalue.co/growth-operating-system
In this episode, Diego von Söhsten, immigrant operator, product leader, and Director of Product Growth at Jobber, opens up about the “after you’ve already proven yourself” flavor of imposter syndrome. He recounts a moment when a senior executive publicly tore down his work (and blamed his accent), and how he rebuilt confidence, created alignment without air cover, and ultimately earned a promotion while shipping a freemium foundation that mattered when COVID hit.Diego talks about learning to over-communicate up and across, turning anti-role-models into fuel for the leader he wanted to become, and building a growth org that prized clarity, storytelling, and psychological safety. He also shares practical ways underrepresented builders can find mentors, ask for help without shame, and protect their inner game when the ground keeps moving.In this conversation, you’ll learn:How to turn painful feedback and bias into long-term fuel for resilience and credibility as a leader.How to use storytelling and structured communication to create alignment and influence without authority.How to build a support network of mentors, peers, and self-awareness to stay grounded under pressure.Things to listen for:(00:00) Intro(01:53) Diego's career beginnings(06:01) Diego’s experience being criticized for his accent(10:43) Thank you to our sponsor, Navattic(15:05) Overcoming and growing from adversity(24:04) Understanding user drop-off and alignment(24:46) The power of storytelling in product management(26:38) Building and leading effective teams(29:31) Diego’s advice to those struggling to find their place(33:13) Working with a good team member who just couldn’t fit(44:58) Balancing passion for work and professional boundariesA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Diego: www.linkedin.com/in/diego-vs Diego’s official website: https://www.vonsohsten.com Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coachingJoin Growth OS: https://deliveringvalue.co/growth-operating-system
In this episode, Kelly Gillease, two-time CMO, daily meditator, and former search marketer turned executive leader, talks candidly about the inner game behind durable leadership. She traces her path from debating podiums to performance marketing at Hotwire, through scale-up chaos at NerdWallet and post-acquisition life at TripAdvisor/Viator—sharing how mindfulness, therapy, and a “true, kind, necessary” feedback filter helped her steady teams when everything felt on fire.Kelly opens up about a tough DEI misstep, how she took the feedback without getting defensive, and why she chose to “run toward” hard conversations instead of retreat. She gets tactical about cross-functional influence (and why debate training still matters), building reputations through appreciation rituals, and choosing environments that actually fit you, even when the shinier title says otherwise.In this conversation, you’ll learn:- How to use “true, kind, necessary” to deliver (and receive) feedback that lands, and what to do when it doesn’t- Practical rituals for team resilience: appreciations, mindful pacing, and calmly problem-solving without losing speed- How to pick the right work environment for your wiring. and navigate the politics, pacing, and trade-offs of big-co vs. startup lifeThings to listen for:(00:00) Intro(01:47) Kelly’s roots, early influences, and formative values(03:51) Where creativity meets ROI: loving both art and math(09:05) Thank you to our sponsor, Navattic(13:50) Scripts and mindsets for hard feedback and conflict(24:23) Owning a DEI misstep, pausing, and moving forward(29:22) Gratitude rituals at work and at home that build morale(39:58) Why big-company bureaucracy wasn’t the right fit(44:20) Radical honesty, necessary conversations, real growthA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Kelly: https://www.linkedin.com/in/kellythepea/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coachingJoin Growth OS: https://deliveringvalue.co/growth-operating-system
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 conversation, you’ll learn:- How to identify your fit Venn diagram (subject matter × work style × company size) and use it to choose roles that compound- A 3-part coaching framework to channel “bulldozer” energy into clear, respectful collaboration- Why building a peer community can be the highest-leverage “career hack” you controlThings to listen for:(00:00) Intro(03:31) First tech job (06:11) Hypergrowth lessons at Pinterest(10:12) Thank you to our sponsor, Navattic(14:37) Realizing no one is an A-player everywhere(17:49) ADHD in the workplace(28:23) Coaching and neurodiversity at work(31:39) Leaving Metafy and its aftermath(43:08) Mallory’s advice to her younger self(47:18) Trusting instincts and following momentumA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Mallory:LinkedIn: https://www.linkedin.com/in/mallorycontois/ Mallory’s official website: https://www.mallorycontois.com/The Old Girls Club: https://www.jointheogc.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coachingJoin Growth OS: https://deliveringvalue.co/growth-operating-system
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 conversation, you’ll learn:How vulnerability, done thoughtfully, can unlock opportunity, community, and your next rolePractical ways to productize your “receipts” with AI or automation so your wins market themselvesHow to deliver and absorb tough editorial feedback while protecting quality and your own voiceThings to listen for:(00:00) Intro(01:34) Ryan’s early career and content creation journey(04:19) Navigating career challenges and feedback(09:37) Thank you to our sponsor, Navattic(11:04) Giving and receiving feedback(14:58) On being a team player(17:41) The importance of adaptability(31:18) The power of vulnerability in job hunting(35:39) Creating a strong online presence(41:57) Difficult conversations in leadership(51:16) Building professional relationshipsA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Ryan:LinkedIn: https://www.linkedin.com/in/ryan-mccready Demostack: https://www.demostack.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coachingJoin Growth OS: https://deliveringvalue.co/growth-operating-system
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 conversation, you’ll learn:Why trusting your team with the truth builds deeper loyalty and respectHow to process the emotional toll of selling, losing, or reinventing a businessWhy intention and self-awareness can turn difficult feedback into lasting growthThings to listen for:(00:00) Intro(01:51) Kirk’s first steps into entrepreneurship(06:26) Building and scaling Discover Outdoors(08:31) Joining Abercrombie & Kent after exit(11:02) Tough feedback and personal growth(20:48) Balancing leadership with family life(25:26) Lessons from difficult conversations(26:04) Deciding to sell Discover Outdoors(28:14) Telling the team about the sale(30:31) Reflecting on honesty in leadership(34:27) The emotional weight of selling(37:48) Finding gratitude in new beginnings(40:03) Preparing mind and body for conversations(45:32) Setting bold, ambitious goalsResources:Connect with Kirk:LinkedIn: https://www.linkedin.com/in/kirk-reynolds/Wilder Retreats: https://discoverwilder.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coJoin Growth OS: https://deliveringvalue.co/growth-operating-systemHire Andrew as your coach: https://deliveringvalue.co/coaching
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 conversation, you’ll learn:Why tailoring your communication for executives can change your career trajectoryHow to confront imposter syndrome with practical reframing techniquesWhy early intervention is the key to resolving team conflicts before they escalateThings to listen for:(00:00) Intro(01:18) Heidi’s early life and education(02:03) Starting career and moving into tech(02:49) Building Kmart e-commerce and ISP(04:37) Joining GoDaddy and career growth(05:20) Developing executive presentation skills(07:28) Thank you to our sponsor, Navattic(13:38) Imposter syndrome in growth teams(22:52) Starting a growth team at GoDaddy(24:30) Applying growth fundamentals successfully(27:54) Strategies for overcoming imposter syndrome(31:46) Navigating difficult workplace conversations(50:01) Seeking guidance and finding mentorshipA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Heidi:LinkedIn: https://www.linkedin.com/in/heidigibsonSubstack: https://heiditheproductgirl.substack.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coachingJoin Growth OS: https://deliveringvalue.co/growth-operating-system
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 conversation, you’ll learn:- Why it’s essential to question feedback and define your own worth- How to recognize poor leadership and build a healthier leadership style- What it takes to reset old wiring around ambition and successThings to listen for:(00:00) Intro(01:59) Devin's upbringing and early career(02:47) Transition to marketing and entrepreneurship(03:01) Facing challenges and finding success(06:33) Pivotal career moments(08:08) Thank you to our sponsor, Navattic(11:33) Navigating tough feedback(17:17) The impact of therapy and self-worth(21:28) Dealing with imposter syndrome(26:46) Realizing the importance of empathy in leadership(28:40) Learning from coaches and mentors(34:48) Balancing work and personal life(38:50) Implementing new habits and boundaries(46:20) Setting goals for fulfillment and happiness(49:25) Caution in advice and embracing relatabilityA huge thanks to this episode’s sponsor:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Devin:LinkedIn: https://www.linkedin.com/in/devinreed/The Reeder (official website): https://www.thereeder.coReed Between The Lines (podcast): https://www.thereeder.co/content-hub/podcastConnect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coachingJoin Growth OS: https://deliveringvalue.co/growth-operating-system
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 conversation, you’ll learn:Why preparation and self-reflection are Justin’s keys to confident leadershipHow to navigate the emotional toll of layoffs, leveling, and managing upWhy clarity of expectations keeps your career evolvingThings to listen for:(00:00) Intro(01:44) Justin's early life in Iowa(04:33) First jobs and early ambitions(07:39) Thanks to our sponsor, Navattic & ThriveStack(10:47) A high-stakes decision to join Amplitude(14:00) The reality of startup life(16:00) Advice for aspiring startup employees(18:55) Feedback and career growth(26:41) Overcoming imposter syndrome(27:11) Navigating leadership challenges(29:16) Seeking clarity in a growing company(30:52) Managing up and building relationships(37:50) Handling layoffs and difficult conversations(43:06) The importance of preparation and role-playing(56:05) The value of deep thinking timeThis episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/Resources:Connect with Justin:LinkedIn: https://www.linkedin.com/in/jjbauer/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching
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 conversation, you’ll learn:Why empathy matters more than titles when leadingHow to build healthy boundaries with work identityWhat it takes to speak up without burning outThings to listen for:(00:00) Intro(01:27) Growing up and schooling in India(03:37) First impressions of the United States(06:37) Starting a career from scratch(08:35) Thanks to our sponsor, ThriveStack(13:52) Becoming a software engineer(17:08) Honest thoughts on giving feedback(18:22) Executive interactions and leadership lessons(26:32) Dealing with imposter syndrome(29:38) Navigating career challenges and transitions(38:17) Facing hard conversations at work(47:38) Balancing career with identityA huge thanks to this episode’s sponsor:ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/Resources:Connect with Rana:LinkedIn: https://www.linkedin.com/in/ranamumtaz/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching
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 conversation, you’ll learn:Why your high performance won’t carry you past your people skillsHow “qualified” and “capable” are two entirely different betsWhat changes when you stop being the hero and start being the glueThings to listen for:(00:00) Intro(01:29) Early life in Vermont and career beginnings(02:24) Joanna’s journalism aspirations(06:56) Receiving devastating career feedback(10:30) Thank you to our sponsor, Navattic(22:50) The AMA that led to a panic attack(29:34) Being capable vs. being qualified(33:14) Imbuing swagger on your team(37:25) A major mistake and avoiding accountability(43:51) Resilience and moving forward(45:48) Unstitching identity from job titles(50:23) Creating a healthy work environmentThis episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value Resources:Connect with Joanna:LinkedIn: https://www.linkedin.com/in/joannalord/ Official newsletter: https://www.linkedin.com/newsletters/7003840481180749824/ Official website: https://www.joannalord.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching
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 conversation, you’ll learn:-Why being a “do-it-all” founder doesn’t scale-How to manage resentment when you get leveled-What it really takes to make hard calls when no one agrees with youThings to listen for:(00:00) Intro(01:04) Meet Raj and his startup resume(02:02) Growing up in the Bay(04:05) First hustle: installing Ethernet cards(07:54) Early failures and impostor syndrome(09:11) Picking product vs. engineering(10:06) Thanks to our sponsors, Navattic & Appcues(12:49) HR call over a side project(16:23) Fear, risk, and side hustles(24:35) Leaving a startup after a new hire(29:01) Facing public failure as CEO(30:06) Rise of IC tracks and redefining success(34:08) Hardest call of his career(44:41) Power of incentives(47:33) His video game theory of growth(52:06) The real risk: not improving(56:00) There’s never a perfect timeThis episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/value Resources:Connect with Raj:LinkedIn: https://www.linkedin.com/in/rajansingh/Linktree: https://linktr.ee/mobilerajX: https://x.com/mobilerajMozilla: https://www.mozilla.org/en-US/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching
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.In this conversation, you’ll learn:Why being a “product purist” almost killed the company and what saved itThe mental spiral founders face when bets aren’t paying offHow to keep a team motivated when the vision keeps changingThings to listen for:(00:00) Intro(01:13) Meet Guru: a story of resilience(02:30) Growing up in Mumbai and early inspiration(04:45) Hustling during a solar eclipse(08:16) Engineer to reluctant founder(10:10) 14 years at Microsoft and why he left(10:47) Thanks to our sponsor, ThriveStack(15:20) Taking VC money (and the fear that comes with it)(23:03) Pivoting to consulting to survive(28:05) Spending nearly $1M on the wrong product(30:25) A pivotal meeting with Microsoft(34:45) Battling imposter syndrome(39:37) The pivots behind ThriveStack(44:19) Redefining the product for real customer needs(47:08) Losing team members as the vision shifts(51:18) Why founders should share failures(54:04) Guru’s biggest mindset shift(55:41) A real take on VC fundingA huge thanks to this episode’s sponsor:ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/Resources:Connect with Gururaj:LinkedIn: https://www.linkedin.com/in/gururajp/ThriveStack: https://www.thrivestack.ai/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching
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.In this conversation, you’ll learn:Why “you’re too nice” was the critique that stuck—and how Michael worked through itThe surprising lesson a failed VP stint taught him about agency and self-worthA simple question that brings clarity to tough calls as a managerThings to listen for:(00:00) Intro(01:24) Growing up in an artistic blue-collar SoCal home(02:30) First jobs and career aspirations(04:29) Journey into music and touring(05:44) Transitioning to tech and SaaS(07:24) How being in a band helped in learning business(11:02) Thank you to our sponsor, ThriveStack(12:20) Being too nice as a leader and finding a balance(21:27) Paying impactful feedback forward(23:38) Navigating imposter syndrome(26:46) Leadership challenges and job insecurity(29:27) Reflecting on career transitions(31:45) A costly mistake and learning experience(36:17) Managing team dynamics as a leader(44:42) A useful shift in perspective(46:46) Driving clarity and embracing intuitionA huge thanks to this episode’s sponsor:ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/Resources:Connect with Michael:LinkedIn: https://www.linkedin.com/in/michaelleibovich/ Adobe: https://www.adobe.com Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching
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.In this conversation, you'll learn:How Steph went from bartending to running high-impact eventsWhat it feels like when your work and values are out of syncHow to navigate inappropriate or personal feedbackWhat manifestation and human design taught her about leadershipThings to listen for:(00:00) Intro(02:29) Foundation-setting experiences(06:19) Finding the right career path(07:31) Thank you to our sponsors, Navattic and Appcues(11:33) Losing love for events and getting it back(14:21) Coaching, core values, and finding alignment(22:16) ADHD, rest cycles, and human design(23:14) Giving feedback without repeating past mistakes(26:36) Balancing professional and personal boundaries(42:21) Manifestation and human design insights(46:43) What’s holding you back?This episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/value Resources:Connect with Steph:LinkedIn: https://www.linkedin.com/in/theeventcritic/The Event Critic: https://www.linkedin.com/company/eventcriticofficial/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching
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.In this conversation, you'll learn:Why Shannon left higher ed and nonprofit work for techThe real story behind inheriting a leadership team without trainingHow to navigate feedback that questions your identityWhat she learned from a rocky client relationship early in her consulting careerThings to listen for:(00:00) Intro(01:25) Business education for the risk-averse(05:04) Career beginnings in tech(09:12) Thank you to our sponsors, Navattic and Appcues(11:50) Facing speed bumps and feedback(20:48) Managing and letting go(26:49) Sensing trouble and taking action(27:45) Navigating tough conversations(30:10) Handling team changes and communication(31:48) Learning from mistakes and setting expectations(45:33) The myth of the all-knowing leader(52:59) What’s next: parental leave, peace, and building enoughThis episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/value Resources:Connect with Shannon:LinkedIn: https://www.linkedin.com/in/shannon-sweeny-curran/SSC Consulting: https://shannonscurran.com/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching
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.In this conversation, you’ll learn:- Why Else left a high-growth role after a massive burnout—and how she rebuilt her career- How early startup culture trained her to overwork and ignore red flags- What she looks for now in leaders, teams, and work environments—and how you can tooThings to listen for:(00:00) Intro(07:06) From law to tech: Elsa's career transition (08:59) Thank you to our sponsor, ThriveStack(20:22) Challenges in the job market (25:44) Burnout and recovery (29:11) The persona of hard work (30:55) Sexual harassment in tech (33:15) Support systems and reporting issues (38:51) Burnout and recovery (41:03) Choosing the right work environment (49:06) Leadership and self-reflection (55:12) AI and the future of work A huge thanks to this episode’s sponsor:ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/Resources:Connect with Else:LinkedIn: https://www.linkedin.com/in/dr-else-van-der-berg-42b8b6a2/ Substack: https://elsevanderberg.substack.com/ Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching
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.Devin opens up about:- Getting fired from two leadership roles and what she did next- Why "servant leadership" backfired as a CEO- The difference between plans and actual strategy (and how she learned it the hard way)- Escaping financial fraud… and nearly getting questioned by the FBI- The power (and downside) of trying to make work feel “safe” for everyoneThings to listen for:(00:00) Intro (01:37) Devin's early life and entrepreneurial spirit (09:02) Transition to professional life (09:17) Thank you to our sponsor, ThriveStack (10:35) Entering the tech world (19:07) Discovering marketing and content creation (23:56) Major career mistakes and lessons learned (30:36) The strategy presentation disaster (31:25) Learning from painful experiences (32:59) Balancing leadership and empathy (34:44) The importance of boundaries (36:08) Handling plagiarism and setting expectations (37:58) Navigating leadership challenges (39:50) Transitioning to CEO (45:03) Dealing with job loss and resilience (48:35) The power of choice and perspective (54:24) Promoting bravery and curiosity (55:51) Everything is made up and that’s where your power isA huge thanks to this episode’s sponsor:ThriveStack: Measure Growth. Find Drivers. Fix Leaks. https://www.thrivestack.ai/Resources:Connect with Devin:LinkedIn: https://www.linkedin.com/in/devinbramhall/Devin’s official website: https://www.devinbramhall.com/Pre-purchase Devin’s book, B2B Content Marketing Strategy: https://www.amazon.com/B2B-Content-Marketing-Strategy-Media-First/dp/1398622516Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching
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.We talk about what it really takes to succeed in product marketing today—and why your biggest edge might come from making uncomfortable moves.If you're a product marketer, startup operator, or aspiring solopreneur, this one's for you.In this conversation, you'll learn:Why Jason left a senior product marketing role before a $2B exitHow he used LinkedIn to overcome imposter syndrome and grow his personal brandThe most common blind spots for PMMs moving into leadershipHow he turned his expertise into a scalable businessThings to listen for:(00:00) Intro(08:54) Jason's early life and entrepreneurial spirit(09:55) Thank you to our sponsors, Navattic & Appcues(12:40) Making hard career decisions as a product marketer(22:10) Real talk for young professionals in tech(28:24) Becoming a product marketing thought leader(30:23) Overcoming imposter syndrome on LinkedIn(32:39) Launching digital products as a PMM(38:29) Why practice beats perfection(43:39) Lessons from managing a team(55:13) Work-life balance and founder mindsetThis episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/value Resources:Connect with Jason:LinkedIn: https://www.linkedin.com/in/oakleyjason/ Productive PMM official website: https://www.productivepmm.com PMM Files Newsletter: https://productivepmm.com/newsletter Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching
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.In this conversation, Erin shares the unique challenges she faced transitioning from a public school teacher to a content strategist, the value of following her heart, and the lessons learned along the way. From managing high-stress jobs in social work to navigating the ups and downs of solopreneur life, Erin opens up about the importance of resilience, adapting to change, and staying true to yourself.Erin opens up about:The surprising path from teaching to techHow freelancing on the side led to a full-time businessThe challenges and rewards of working for yourselfWhy following your heart is the key to successNavigating life as a mom, entrepreneur, and content expertThings to listen for: (00:00) Dramatic rescue (01:05) Erin's unconventional career path (06:04) High school adventures and moving to Massachusetts (08:11) College decisions and career beginnings (09:46) Teaching and working with troubled teens (11:11) Thank you to our sponsors, Navattic & Appcues (13:49) From public school teacher to marketing maven (26:26) The solopreneur journey (28:55) Navigating career transitions (29:17) Freelancing success and challenges (30:16) Balancing family and work (34:16) The importance of mindset (43:59) Health challenges and business impact (48:36) AI concernsThis episode is presented by: Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/valueResources: Connect with Erin:LinkedIn: https://www.linkedin.com/in/erinbalsa/Website: https://hausofbold.com/Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching