Revenue Mind

Jolie Shapiro

Welcome to Revenue Mind! This is where we dive into the side of revenue leadership that rarely gets talked about: mental health. Every episode is packed with real, raw stories straight from the business world’s pulse. We’ve got insights from top execs and rising stars on the mental challenges and victories they face. Our mission? To put mental health in the spotlight, proving it’s just as critical as hitting your revenue goal.

  1. 12/17/2025

    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 Learn more about Jolie Shapiro Learn more about Revenue Mind

    31 min
  2. 12/10/2025

    Don’t Be an A*****e | 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 Learn more about Jolie Shapiro Learn more about Revenue Mind

    23 min
  3. 12/03/2025

    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 Learn more about Jolie Shapiro Learn more about Revenue Mind

    31 min
  4. 11/19/2025

    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 Learn more about Jolie Shapiro Learn more about Revenue Mind

    37 min
  5. 11/05/2025

    Life Isn’t an 800 | Natalie Marcotullio, Head of Growth and Product Marketing at Navattic

    Former D‑1 sprinter turned growth leader, Natalie Marcotullio, knows that winning starts with knowing when to rest. She joins Jolie to riff on boundaries, bad first drafts, and why your Minimum Viable Product should come with a Maximum Viable Pause. If your Slack pings feel louder than your heartbeat, hit play.  Key Takeaways • Athletic mindset = built‑in grit—but recovery is the power move • Saying no is a growth strategy; focus > FOMO • Fail fast, learn faster: your worst MVP is better than a perfect idea on ice • Data drives decisions, but self‑care drives you • Introversion can be a sales superpower • Autonomy > luxury lifestyle • Turn work into play Timestamps 00:00 Identity check: family roots & the runner’s edge 02:57 Using an athletic mindset to outpace revenue fires 05:57 Why the biggest lessons hide inside the losses 09:03 The radical art of saying “no” 12:01 Drawing lines so burnout can’t cross them 15:12 Therapy, walks, and other legit leadership tools 25:12 Level‑up season: taking on new challenges 30:52 MVPs that keep the team (and budget) intact 36:44 Decode team motivations, unlock collaboration 38:37 Spotting burnout before it banners your calendar 42:46 Creativity pops when you step away 44:51 Building a culture where mental health is KPI #1 Links Learn more about Natalie Marcotullio Learn more about Jolie Shapiro Learn more about Revenue Mind

    36 min
5
out of 5
16 Ratings

About

Welcome to Revenue Mind! This is where we dive into the side of revenue leadership that rarely gets talked about: mental health. Every episode is packed with real, raw stories straight from the business world’s pulse. We’ve got insights from top execs and rising stars on the mental challenges and victories they face. Our mission? To put mental health in the spotlight, proving it’s just as critical as hitting your revenue goal.