Lead Your Life | Robert LoCascio, Founder of LivePerson

Lead Your Life | Robert LoCascio, Founder of LivePerson

Rob LoCascio (founder/former CEO of LivePerson) joins Jolie to riff on purpose, grit, and what it really takes to build for the long haul—mentally, emotionally, and spiritually. From sleeping on an Ikea couch during LivePerson’s earliest days (and still keeping the couch as a reminder) to building two new AI startups, Rob shares why “certainty + control” can quietly destroy founders—and how reconnecting with God helps him cut through the noise, lead with humility, and build technology that brings families closer (instead of pulling them apart). Key Takeaways • “What makes you, you?”: • The couch years: two years living in an office • Helping at a homeless shelter reframed “feeling sorry for yourself.” • Grit is in everyone if you’re willing to be somewhere uncertain enough to grow. • Spiritual practice can elevate the conversation beyond your own head. • Building products that strengthen community/connection—not just utility. • Kids + screens: the “scroll” is engineered addiction; creation is the antidote. • KID’s startup philosophy: kids use AI to create stories, art, and music with parents. • If AI is getting “smarter,” it’s often because we keep feeding it our knowledge. • Certainty, control, and ego, and why letting go doesn’t kill ambition. • Rob’s deck-of-cards reality check: gratitude beats comparison. • The closing reminder: don’t follow your life—lead it. Timestamps 00:00 Intro / full-circle LivePerson moment 01:24 “What makes you, you?” 02:50 The “never quit” trait—and how it shows up in business 03:14 Sleeping on the couch: the early LivePerson story 05:45 Therapy + volunteering: perspective, humility, and resilience 07:13 Can grit be taught? 09:05 “Put people in uncertainty and they’ll adapt” 09:37 New chapter: two startups + young kids + building again 10:30 Cutting through the noise: getting closer to God 11:26 Jolie’s 12-step lens: higher power as connection 14:03 Purpose, community, and the question Rob couldn’t answer before 15:12 Why these two companies feel more “purpose-aligned” 17:47 LivePerson vs. now: utility vs. human connection 18:00 KID and “Bring Back the Bond” 19:53 The iPad-at-3AM story: screens as a drug for kids 20:04 How KID aims to change screen time 22:38 “Own your intelligence”: personal AI and reclaiming your data 24:50 AI safety and why kid-first design matters 25:48 COPPA + building for children the right way 27:25 Obsessive founders and addictive personalities 29:22 The deadliest founder traits: certainty + control + ego 30:56 Learning it the hard way 33:59 “There’s a CEO above you”: surrendering control without losing ambition 38:46 The deck-of-cards analogy: gratitude over comparison 41:30 Social media illusions + dot-com déjà vu 43:31 Lead it. Don’t follow it.” 45:05 Where to find Rob Links Learn more about Robert LoCascio [https://www.linkedin.com/in/rlocascio/] Learn more about Jolie Shapiro [https://www.linkedin.com/in/jolieshapiro/] Learn more about Revenue Mind [https://www.linkedin.com/company/revenuemind/]

Be Unapologetically You | Meghann Misiak (The Sales Witch)

In this episode, Jolie Shapiro sits down with Meghann (“That Sales Witch”) to unpack what happens when high performance turns into survival mode—and what it looks like to rebuild from burnout without abandoning ambition. They talk about intuition, tarot, somatics + chakras, and why the most “professional” thing you can do in sales (and on LinkedIn) is stop pretending you’re a robot. Meghann also shares a practical framework for “healthy hustle”: intention first, tactics second—so your sales process aligns with who you actually want to be. Key takeaways • Meghann embraces her “Sales Witch” identity as her real edge. • Burnout can hit as a moment (not just months): shutdown, numbness, heaviness. • Body signals are data: stress can show up physically in different ways. • Somatic + energetic frameworks can help as mirrors for what’s under the surface. • Tarot as archetypes: the “death” card as endings → new beginnings. • Burnout recovery can take years: rewiring how you work isn’t a quick fix. • SaaS culture rewards the mask: “push through” becomes a slippery slope. • Industry problem: “okay” gets called “excellent” without real feedback. • Healthy hustle is intention-led: values/archetype → mindsets → tactics. Timestamps 00:00 Intro + meeting after connecting online 01:15 “What makes you, you?” → the Sales Witch identity shift 03:18 Sales origins + how “Sales Witch” came to life 04:40 From quota to training (Sandler, MEDDIC, enablement) 08:51 Burnout: why we don’t see it until we hit it 10:30 Meghann’s burnout moment + leave of absence 13:00 Jolie’s burnout signals + recalibrating expectations 15:28 Somatics + chakras: where stress lives in the body 19:15 Tarot + the “death card” year: endings as doorways 21:48 Healing tools, dissociation, and why recovery isn’t fast 27:25 SaaS truth: feedback, pipeline honesty, and “okay” culture 33:06 Hustle culture as a slippery slope 38:35 Healthy hustle example: intention → tactics 49:53 LinkedIn framework: value vs growth vs brand 56:21 Where to find Meghann Links Learn more about Meghann Misiak [https://www.linkedin.com/in/megmisiak/] Learn more about Jolie Shapiro [https://www.linkedin.com/in/jolieshapiro/] Learn more about Revenue Mind [https://www.linkedin.com/company/revenuemind]

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]