Make a Game You Can Win, Chris Savage, Co-Founder & CEO of Wistia

It Doesn’t Have to Be This Hard | Claude Silver, Chief Heart Officer at VaynerX

From a 93‑day Outward Bound in the Colorado Rockies to hiding her sexuality at work and now holding impossible DEI conversations as Chief Heart Officer at VaynerX, Claude Silver shares why being yourself at work is both risky and necessary: change the song in your head, remove shame, add tenderness, and stop asking humans to act like machines. Key Takeaways • Back‑nine season: joyful service, big heart, total goofball. • Wilderness wake‑up: 93‑day Outward Bound → “get another song in your head.” • Dyslexia turned from school pain into one of her superpowers. • Hiding that she was gay at work led to shame and a fragmented life. • Emotional optimism: feelings as data for hard DEI + culture conversations. • The weight of “impossible” topics (racism, Oct 7) as a white Jewish leader. • Macro: remove shame, add tenderness; let people be “normally messy” at work. • Goal isn’t “I love myself” overnight—just helping people get to “I like myself.” Timestamps 00:00 Intro  01:20 “Who are you in this season?” — back nine, joyful service, goofball 02:10 Taurus energy, love of human behavior, and being Chief Heart Officer 03:30 Telling Gary V she’d write a book & why Be Yourself at Work exists 05:30 93‑day Outward Bound story & “you better get another song in your head” 09:05 Colorado / Leadville / Denver and mountain metaphors 10:40 Learning differences: dyslexia, dyscalculia, school pain → superpower 12:20 Abandoning herself by hiding she was gay at work; shame and a double life 18:01 Brutal DEI day: emotional optimism, accountability, and a hard convo. 24:50 The weight of “impossible” topics as a white Jewish leader 32:52 Macro vision: Helping people get to “I like myself.” 37:48 Where to find Claude Links Learn more about Claude Silver [https://www.linkedin.com/in/casilver/] Learn more about Jolie Shapiro [https://www.linkedin.com/in/jolieshapiro/] Learn more about Revenue Mind [https://www.linkedin.com/company/revenue-mind-podcast]

Don’t Be an Asshole | Ryan Barry, CEO of Appcues

From “fourth child” dad and self-described Peter Pan to tech executive navigating LinkedIn doom scrolls and shifting markets, Ryan Barry shares how playfulness and discipline can coexist: keep your values simple (be kind, work hard, don’t be an asshole), protect your energy, and stay present enough to lead at work and at home without burning out. Key Takeaways • Simple family rulebook: find what makes you happy, work hard, don’t be an asshole. • Lower-middle-class roots = inclusivity, big table, relentless work ethic. • Hustle got him far—but unchecked hustle leads straight to burnout. • Boundaries are fluid: “WiFi’s broken” days, phone-free time, walks and hikes. • Limit the doom scroll: LinkedIn morning + night; learn more from real conversations. • Presence over pretending: if you can’t be fully there, step away. • Name the “flood”: walks, breathing, and simple meditation to reset (and teach his kids). Timestamps 00:00 Intro / “What makes you you?” 02:00 Peter Pan adulthood, fatherhood, and shifting priorities 06:00 Family values: happy, hardworking, and not being an asshole 09:30 Lower-middle-class upbringing, immigrant mom, construction-worker dad, inclusivity 14:00 Tech, LinkedIn doom scroll, and the comparison trap 18:30 Boundaries: WiFi-free Saturdays, nature, fewer meetings, more white space 23:00 Presence, energy, and how his mood impacts the whole company 27:30 Flood moments, ADHD, anxiety tools, and meditating with his son 31:30 Executive coaching, burnout, and not wanting to be “60 and lonely” 34:00 Where to find Ryan Links Learn more about Ryan Barry [https://www.linkedin.com/in/ryan-barry-8354036/] Learn more about Jolie Shapiro [https://www.linkedin.com/in/jolieshapiro/] Learn more about Revenue Mind [https://www.linkedin.com/company/revenue-mind-podcast]

Own the Seat You Choose | Warren Zenna, Founder of The CRO Collective

From CRO burnout and impostor syndrome to AI “bionics” and bot‑to‑bot buying, CRO Collective founder Warren Zenna argues that work is a choice, not a sentence: own the role you’re in, get honest about fit, build real competence, and lean on people so you don’t do it alone. Key Takeaways • Burnout = fit + ownership: you chose the role; change how you work or leave. • Success is a weak teacher; a misfit CRO stint clarified he’s a better coach. • Impostor syndrome drives overwork, weak hires, and reluctance to delegate. • Teams mirror leaders: blame and politics usually signal dodged responsibility. • Competence + communication: be excellent at your craft and at explaining it. • AI as bionics, not a mask: tools amplify you, but you still “pay the piper.” • Grounding > grinding: relationships, sleep, food, and movement keep you sane. Timestamps 00:00 Intro /“What makes you you?” 01:10 Parents, genetics, culture & identity 03:20 CRO burnout, fit, and “no victims” 08:10 Why the CRO role wasn’t for Warren 10:30 Coaching CROs: impostor syndrome & self‑sabotage 14:40 Leadership, responsibility, and political cultures 16:40 What great CROs and companies do differently 19:20 AI as bionics vs. fake competence 26:00 AI agents in sales & bot‑to‑bot buying 30:00 Staying grounded: people, self‑care, responsibility for others 32:20 Why he built The CRO Collective / where to find Warren Links Learn more about Warren Zenna [https://www.linkedin.com/in/warrenz/] Learn more about Jolie Shapiro [https://www.linkedin.com/in/jolieshapiro/] Learn more about Revenue Mind [https://www.linkedin.com/company/revenue-mind-podcast]

Make a Game You Can Win, Chris Savage, Co-Founder & CEO of Wistia

From live-recording on Wistia’s new (beta) platform to reframing “failure,” funding, and mental fitness, Wistia cofounder/CEO Chris Savage shares how creative optimism and long horizons build durable companies: pick problems worth working on for years, listen hard, ship again, and design recovery so you don’t burn out. Key Takeaways • Failure vs feedback: crickets → quit; caring feedback → iterate. • Choose a winnable game: align funding with your tempo (not “triple-triple-double”). • Small + patient can be an edge; timing is often slower than you think. • Recovery is a strategy: daily workouts ↑ stress capacity; delegate to protect energy. • Lead (and parent) by modeling—behavior ripples through teams. • Honesty compounds trust: own mistakes publicly and flip them into loyalty. • Use customers’ language; expect spike-drop-rebuild post-launch. Timestamps 00:00 Intro / “What makes you you?” 02:00 UX tips: Stage view, pop-out, device-switch quirks 05:20 “What makes you you?”—optimistic, excitable, pathfinding 08:30 Failure vs. feedback; when to persist vs. walk away 10:45 Webinars pivot: acquire → rebuild → months of low trials/no retention 15:10 Funding fit & expectations: bootstrapped + debt buyback; different game 18:30 Near-sale (2017) → “pretend we sold”: vacations, delegation, balance 22:40 Stress & recovery: daily workouts, capacity, team leverage (oxygen-mask rule) 26:00 Modeling at home & work; radical honesty (“we messed up” email) 29:30 Wistia's success: right macro shift, patience, culture; be your own best customer 33:00 Launch reality: spike → drop → compounding touchpoints 34:30 Where to find Chris  Links Learn more about Chris Savage [https://www.linkedin.com/in/cjsavage/] Learn more about Jolie Shapiro [https://www.linkedin.com/in/jolieshapiro/] Learn more about Revenue Mind [https://www.linkedin.com/company/revenue-mind-podcast]

Drop the Performance | Ben Wise, Founder of Storyd

From the highs of vibe-coding to the reality of bugs, burnout, and hype, writer/AI consultant Ben shares how to use AI as leverage without losing yourself. His mantra: slow is fast—own the work, calibrate risk, and double down on the only durable moat in an automated future: real human connection. Key Takeaways • Use AI for leverage, not identity—watch the “God complex.” • Learn it before you delegate it; verify and own the code. • Abstraction creates cognitive debt—stay close to high-stakes work. • Entrepreneurship ≠ morality; luck and timing matter—set your risk bar. • Protect non-performative spaces; social + AI can distort self-worth. • Relationships outlast tools—connection drives health and resilience. Timestamps 00:00 Intro / “What makes you you?” 02:47 Vibe-coding highs → bugs, burnout, humility 07:05 Learning to program; owning security and outcomes 15:16 AI’s limits: the “eager amnesiac intern” & “slow is fast” 24:28 Pulling back from the praise-glaze / God complex 30:38 Social media parallels; incentives & guardrails 36:29 Mental health: delusions, boundaries, real-world checks 49:43 Human connection as the future-proof moat 53:28 Where to find Ben Links Learn more about Ben Wise [https://www.linkedin.com/in/benawise/] Learn more about Jolie Shapiro [https://www.linkedin.com/in/jolieshapiro/] Learn more about Revenue Mind [https://www.linkedin.com/company/revenue-mind-podcast]