#114 - Kim Scott, Radical Respect and Radical Candor: How to Build Teams That Challenge Directly and Care Personally [ENCORE]

What does it actually mean to care about someone at work?In this encore episode, Alisa Cohn sits down with Kim Scott, former Apple and Google executive and bestselling author of Radical Candor and Radical Respect, to explore the real cost of silence, bias, and avoidance inside teams.This episode is not theoretical. It is deeply practical. From how to solicit feedback effectively, to how to “disrupt bias without disrupting the meeting,” to how to move through shame and defensiveness, Kim offers a roadmap for leaders who want high standards without losing humanity.If you care about building strong teams, giving better feedback, or creating a culture where people can actually do their best work, this conversation will challenge you in the best way.You’ll learn:Why Radical Candor works and how leaders often misapply itThe hidden damage caused by ruinous empathyWhy silence at work is more costly than discomfortHow to solicit feedback without triggering defensivenessThe difference between bias, prejudice, and bullyingHow to “disrupt bias without disrupting the meeting”How leaders can build psychological safety through vulnerabilityWhy upstanders matter and how to be oneWe talk about:00:00 The painful story behind Radical Candor and why silence cost more than honesty03:00 The Radical Candor framework explained: care personally + challenge directly08:00 Ruinous empathy and the real consequences of avoiding feedback12:00 Why soliciting feedback is the first leadership move18:00 How to ask for feedback without getting fake reassurance24:00 From Radical Candor to Radical Respect: what prompted the new book28:00 The two definitions of respect and why they matter31:00 Bias, prejudice, and bullying, simple definitions leaders can use35:00 How to disrupt bias without disrupting the meeting44:00 Managing shame and defensiveness when your bias is flagged51:00 The cost of silence and the power of being an upstander57:00 Why discomfort is the price of real collaborationFollow Kim onInstagram: https://www.instagram.com/radicalcandorofficialLinkedIn: https://www.linkedin.com/in/kimm4/Medium: https://kimmalonescott.medium.com/ Website: https://kimmalonescott.com/ Connect with Alisa!Follow Alisa Cohn on Instagram: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

What does it really take to evolve from first-time founder to public company CEO without losing conviction, culture, or clarity?In this episode of From Start-Up to Grown-Up, Alisa Cohn sits down with Matt Oppenheimer, Co-Founder and CEO of Remitly, the global financial services company serving customers in more than 170 countries.Matt shares the leadership evolution behind building Remitly from an early-stage startup into a publicly traded company. From spotting the broken experience of international money transfers while living in Kenya, to navigating executive transitions, IPO readiness, board dynamics, and imposter syndrome, Matt reflects on the real work of founder to CEO leadership growth.This conversation explores how conviction differs from stubbornness, why great founders fall in love with the problem rather than the solution, and how culture must evolve alongside strategy. If you are building, scaling, or leading a growth-stage company, this episode offers a practical and deeply human roadmap.You’ll learn:Why founders must apply grit to the problem, not the solutionHow to balance curiosity with decisiveness as a leaderThe difference between startup execution and public company leadershipHow to design culture intentionally and evolve it over timeWhy executive transitions are about stage-fit, not loyaltyWhat IPO readiness really requires behind the scenesHow to manage imposter syndrome and board pressureWhy psychological safety with investors mattersHow “towering strengths” create leadership shadowsWhat it means to grow into the CEO your company needsWe talk about:00:00 The origin of Remitly and identifying a global problem03:00 Grit, flexibility, and falling in love with the problem06:00 Growth mindset, curiosity, and listening to feedback10:00 Global perspective and customer centricity14:00 Designing culture from day one18:00 Evolving values as strategy evolves23:00 Hiring executives for stage, not sentiment28:00 Managing leadership transitions thoughtfully33:00 Founder development plans and 360 reviews36:00 Moving from “doing” to leading at scale42:00 IPO preparation and avoiding IPO as the sole goal46:00 Becoming a public company CEO49:00 Imposter syndrome and board dynamics53:00 Advice for founders scaling their leadershipFollow Matt onLinkedIn: https://www.linkedin.com/in/mattoppenheimer/Website: https://www.remitly.com/Connect with Alisa!Follow Alisa Cohn on Instagram: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

What actually drives long-term growth, in business, leadership, and life?In this replay episode, Alisa Cohn sits down with Sal Di Stefano, co-founder of Mind Pump Media, to explore what it really takes to build something that lasts. From turning a podcast into a multi-revenue media company to navigating cofounder relationships, conflict, and personal growth, Sal shares hard-earned lessons from nearly a decade of building Mind Pump without venture capital or shortcuts.This conversation goes beyond tactics. Sal breaks down why authenticity creates trust at scale, how to know you’ve chosen the right cofounders, and why being “right” is far less important than staying aligned. He also shares how prioritizing physical health and personal boundaries made him a stronger leader, not a weaker one.If you’re a founder, creator, or leader who wants sustainable growth without burnout, this episode offers a grounded, honest look at what actually works.You’ll learn:Why authenticity is a growth strategy, not a branding tacticHow to recognize cofounder alignment before problems surfaceWhy being right can hurt teams and trustHow physical health supports better leadership decisionsWhat Mind Pump did differently to build loyalty and longevityWe talk about:00:00 Leadership responsibility, health, and personal accountability01:00 Introducing Sal Di Stefano and Mind Pump Media03:00 Why long-form podcasting enabled real connection and trust05:10 Turning Mind Pump into a multi-revenue media business09:10 Building trust before monetizing and letting the audience lead13:45 Early revenue growth and turning down misaligned sponsors18:30 Finding the right cofounders and values alignment22:15 Conflict, disagreement, and committing as a team30:45 Navigating growth, the pandemic, and unexpected momentum36:10 Authenticity, vulnerability, and being recognized in public40:20 Boundaries, family, and redefining success as a leader45:00 Focus, leverage, and choosing what actually moves growth49:20 Serving existing customers before chasing new ones53:40 Why great leaders and coaches must be great communicators57:40 Final reflections on leadership, health, and the long gameFollow Sal onX: https://x.com/mindpumpsalPodcast: https://mindpumppodcast.com/ Website: www.mindpumpmedia.comConnect with Alisa!Follow Alisa Cohn on Instagram: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

What does it actually mean to lead with authority and empathy, without burning out, people-pleasing, or losing yourself in the process?In this episode, Alisa Cohn sits down with clinical psychologist, parenting expert, and bestselling author Dr. Becky Kennedy to explore why the skills that make great parents also create the strongest leaders.Dr. Becky introduces the concept of sturdy leadership, a grounded approach that rejects both authoritarian control and emotional over-accommodation. Instead, it teaches leaders how to hold boundaries, stay regulated during conflict, and repair relationships when things go sideways.This conversation unpacks why leadership is not about managing everyone’s feelings, how guilt often disguises emotional over-responsibility, and why repair after rupture is more powerful than perfection. You’ll learn how to handle defensiveness, set boundaries without shame, navigate imposter syndrome, and build trust through consistency and self-leadership.You’ll learn:What “sturdy leadership” really means and why authority without aggression builds trustWhy setting boundaries often triggers guilt and how to tell guilt apart from emotional over-responsibilityHow repair strengthens relationships more than getting it right the first timeHow to handle defensiveness, emotional reactions, and resistance at workWhy scripts and practice reps are essential leadership skills, not crutchesHow predictable conflict shows up at work and how to lead through it calmlyWhy imposter syndrome never fully disappears and how to lead anywayWe talk about:00:00 Why parenting is leadership training and why leadership is human work03:45 What sturdy leadership is and why extremes fail06:20 The “sturdy pilot” metaphor and how leaders create safety in turbulence10:30 Authority vs empathy, and why feelings should not dictate decisions14:40 Boundaries, guilt, and emotional over-responsibility at work18:50 Why empathy doesn’t mean absorbing other people’s emotions22:30 Handling defensiveness and emotional reactions in professional settings31:45 Predictable conflict, patterns, and solving the real issue36:10 Repair after rupture and why it builds trust faster than perfection42:30 How unrepaired moments erode connection and performance45:20 Imposter syndrome, self-leadership, and staying in the driver’s seat49:00 What Dr. Becky wishes she had known earlier about growth and leadershipFollow Dr. Becky onInstagramYouTubeTikTokFacebookWebsiteConnect with Alisa!Follow Alisa Cohn on Instagram: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

What does it actually take to build something that has never existed before?In this episode, Jim McKelvey, co-founder of Square (now Block), breaks down the real story behind building Square from scratch, not with a perfect plan, but through necessity, invention, and relentless problem-solving. Jim introduces the concept of the Innovation Stack, why innovation is rarely chosen willingly, and why copying “what worked before” fails when you’re solving a problem no one else has solved. He shares the moment Square felt real, the panic of Amazon launching a competing product, and the counterintuitive strategy that helped Square survive.You’ll learn:What the Innovation Stack is and why it protects companies from copycatsHow Square started from a single lost sale and grew into a global companyWhat happens emotionally when you’re building something no one understands yetWhy copying best practices can fail when you’re solving a brand-new problemWhy mission-driven teams outperform money-driven ones over timeWe talk about:00:00 Why timing is everything, and why being “too early” still hurts05:30 The moment Square was born, one lost sale that changed everything10:00 Why the payments industry was designed to exclude small businesses16:30 Mission vs money, and why people joined even when they could leave20:00 Amazon launches a competing product, and Square’s unexpected response26:00 The Innovation Stack explained, and why it’s almost impossible to copy31:00 Panic attacks, pressure, and the nervous system cost of building35:30 Copying vs innovating, and where founders get trapped47:00 Imposter syndrome, even after successFollow Alisa Cohn onInstagram: https://www.instagram.com/alisacohn/ Twitter: https://x.com/AlisaCohn Facebook: https://www.facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better): AlisaCohn.com/scriptsGrab a copy of From Start-Up to Grown-Up by Alisa Cohn from AmazonConnect with Alisa!Follow Alisa Cohn on Instagram: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

In this episode, Robbie Bent,CEO and Co-founder of Othership shares his remarkable journey from addiction recovery to leading one of today’s most innovative wellness brands. Othership combines sauna, ice bath, and guided breathwork to help people regulate their emotions and connect in community. Robbie opens up about the evolution of his leadership, the challenges of scaling a purpose-driven business, and the importance of authenticity as a founder.From a small Toronto garage gathering during the pandemic to thriving studio locations in Toronto and New York (with more on the way), Robbie’s story is one of resilience, self-awareness, and growth. He and Alisa discuss creating spaces for emotional connection, navigating co-founder dynamics, and learning to lead through imperfection. Robbie’s approach to leadership is a powerful reminder that emotional wellness isn’t just personal, it’s foundational to how we build, lead, and grow.Where to find Robbie:Othership websiteXRobbie on InstagramOthership on InstagramLinkedInTimestamps:(00:00) Introduction to the Conversation(02:55) The Importance of Emotional Space(05:59) The Mechanics of OtherShip(08:56) The Backstory of OtherShip(12:01) Choosing New York as a Market(15:02) Building Community and Connection(18:01) Co-Founder Dynamics and Relationships(26:08) Navigating Difficult Conversations(31:40) Challenges of Expansion and Financial Strain(37:33) The Weight of Responsibility and Fear(39:42) Self-Awareness and Personal Growth(48:42) Balancing Excellence with Empathy(52:12) Creating Accessible Wellness Experiences(54:44) Building a Brand with Emotional Connection(57:19) The Evolution of Brand and Personal Experience(59:35) Learning from Mistakes and Trusting Your Gut(01:03:12) The Role of a CEO and Leadership Growth(01:10:07) Overcoming Imposter Syndrome and Embracing AuthenticityConnect with Alisa!Follow Alisa Cohn on Instagram: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

Semyon Dukach, the Founding Partner at One Way Ventures, serial entrepreneur, and former leader of the famed MIT Blackjack team, joins me to share his extraordinary journey from arriving in the U.S. as a Soviet refugee to becoming one of New England’s top venture capitalists. We discuss his path from leading the MIT Blackjack team to startup founder to prolific investor. One Way Ventures invests only in immigrant founders and we discussed how he developed that thesis. We also talk about personal growth, overcoming imposter syndrome, and what it really takes to become an exceptional founder and leader.Where to find Semyon:XLinkedInOne Way VenturesTimestamps:(00:00) From Pacman to Blackjack: A Unique Journey(02:58) Lessons from the MIT Blackjack Team(05:54) Transitioning from Operator to Investor(08:52) The Immigrant Experience and Entrepreneurship(11:46) Building Trust in High-Stakes Environments(14:36) The Power of Immigrant Founders(17:44) Branding and Recognition in Venture Capital(28:18) Building a Strong Network for Deal Flow(31:39) Recognizing Undervalued Immigrant Founders(34:19) Traits of Extraordinary Founders(37:07) The Importance of Customer Focus(38:53) Growth Through Partnership and Experience(42:23) Navigating the Challenges of Venture Capital(44:56) Turning Disappointments into Opportunities(46:19) Dealing with Imposter Syndrome(47:32) Lessons Learned on the Entrepreneurial Journey(51:03) The Inner Drive of EntrepreneurshipConnect with Alisa!Follow Alisa Cohn on Instagram: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

Jonathan Wolf is the co-founder and CEO of ZOE, the science-based nutrition company using data to transform how people eat. In this candid conversation, he joins me to explore what it takes to build a mission-driven company, how to lead with more clarity and transparency, and why the way we eat is more broken and more fixable than most people think.ZOE’s origin story is as unconventional as it is inspiring. After scaling Critéo into a billion-dollar business, Jonathan stepped away with no plan and plenty of questions. That wandering period led him to microbiome researcher Tim Spector, and from there, to the bold idea of using AI and big data to personalize nutrition at scale. Eight years and 250,000 microbiome samples later, ZOE is running the world’s largest nutrition science study and has launched a free app to help people assess their food in real time.Where to find Jonathan:ZOEXLinkedInTimestamps:(00:01:30) Jonathan’s Path from Tech Operator to Founder(04:24) Why Success at a $2B IPO Still Felt Empty(05:39) Sabbatical, Loss of Structure, and Founder Identity Crisis(06:58) The Serendipitous Meeting That Sparked ZOE(09:27) Letting Go of Outcome Obsession and Learning to Value the Process(11:48) Chasing Achievement vs. Living in Alignment with Values(14:19) Becoming a Founder Later in Life—and Why That Helped(17:05) Why Being Naïve About an Industry Can Be a Competitive Advantage(19:45) Raising €7 Million in Just a Few Weeks(20:53) Convincing World-Class Scientists to Bet on an Unproven Idea(24:20) Building a Flywheel: Science, Data, and Community(29:51) Using Technology and AI for Human Good(38:47) From Pure Science to a Scalable Business Model(43:05) Creating the ZOE Membership Flywheel(48:07) Community Science as a Core Business Strategy(50:44) Transparency, Trust, and Leading Through Hard Decisions(54:28) Mission-Driven Culture and Retaining Great Talent(57:56) Growing from Founder to Leader as the Company ScalesConnect with Alisa!Follow Alisa Cohn on Instagram: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

Kass and Mike Lazerow who are serial entrepreneurs, seasoned investors, and co-authors of Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success joined me for one of the most honest conversations I’ve had about what it really takes to build companies and build a life. They share the unvarnished truth about their journey: surviving the dot-com crash, buying Golf.com back from bankruptcy, founding and scaling Buddy Media (eventually acquired by Salesforce for $745 million), and raising three kids while raising capital. They talk about the choices that shaped them, including why they walked away from a bigger offer from Google and how radical transparency kept their team committed during a three-month period when they couldn’t make payroll.We also dive into the patterns they see in the 100+ startups they’ve backed like how ego, secrecy, and shiny-object syndrome derail founders along with the essential habits that help leaders stay grounded. And because they work together and live together, they open up about how they divide responsibilities, handle stress, and stay connected through exits, pivots, health scares, and everything in between. Their upcoming book distills 50 hard-earned lessons about leadership, resilience, and building a life that actually works. This episode gives you a powerful preview and a reminder that the entrepreneurial path is messy, human, and absolutely worth it.Where to find Kass and Mike:InstagramFacebookMike's LinkedIn Kass’ LinkedInTimestamps:(00:00) The beauty in the struggle: why entrepreneurship is a love story(01:10) Resilience as identity and getting punched 10 times for one win(19:19) Creating a workplace people stay in through loyalty and learning(20:16) Radical transparency: telling the team you might not make payroll(21:06) Bad news vs. surprises: the leadership rule that protects trust(22:21) Benevolent dictatorship vs. democracy: choosing decisive leadership(23:53) Honesty as the most valuable currency in a downturn(37:30) The pivot mindset: knowing when to throw things away(52:23) Life after a big exit and leaving ego at the door(53:45) Why working under others made Mike a stronger leader(58:26) Founders and the guilt tax: the emotional cost of ambition(01:08:45) The long-term power of paying it forward(01:10:01) When cofounding goes wrong: misalignment, fallout, and repair(01:12:50) Picking the right partner—in life and in business(01:13:29) Cofounder “prenup” talks: values, work ethic, commitment(01:14:05) No shortcuts: filtering for grit and willingness to shovel(01:15:16) Why overlapping founder roles create conflict(01:21:12) A simple lens for evaluating opportunities without the jargon(01:22:14) Imposter syndrome and grounding yourself under pressure(01:24:22) What they wish they’d known: focus, phConnect with Alisa!Follow Alisa Cohn on Instagram: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

Randy Komisar is an entrepreneur and investor at Kleiner Perkins.Previously, he was a co-founder of Claris Corp., served as CEO for LucasArts Entertainment and Crystal Dynamics, and acted as “virtual CEO” for such companies as WebTV and GlobalGiving. Randy also served as CFO of GO Corp. and as senior counsel for Apple Computer, following a private practice in technology law.Randy is a founding director of TiVo and serves on the Roadtrip Nation Advisory Board and Orrick’s Women’s Leadership Board. He is the author of the best-selling book,The Monk and the Riddle, as well as several articles on leadership and entrepreneurship. He is also the co-author of Straight Talk for Startups, the insider best practices for entrepreneurial success, Getting to Plan B, on managing innovation, and I F**king Love that Company, on building consumer brands.This conversation with Randy Komisar is just spectacular! We dive right into how he turned his interview with Neil Young from disaster to success, why growing up with a professional gambler sharpened his communication skills, the way that luck factors into your career, and the way to maximize your chances of serendipity coming your way.You’ll learn pearl after pearl of wisdom from Randy in our conversation, including a crucial question he asks as an investor to any entrepreneur to assess what they’re made of.Randy’s such a great storyteller, and this discussion is not to be missed!Where to find Randy:Kleiner and PerkinsTimestamps:(00:00) The Neil Young interview disaster—and how Randy saved it(02:00) Throwing away the script and learning to “follow the spark”(03:15) Reading people: Randy’s people-sense and street upbringing(04:00) Growing up with a salesman and professional gambler father(05:20) Lessons from watching gamblers: losing stories, tells, and ego(07:00) How his father’s instincts shaped Randy’s BS-detector in VC(12:35) Self-awareness, delusion, and Buddhism’s core teaching(13:40) Coaching as holding up a mirror(14:20) Randy’s winding path: from upstate NY to Brown University(15:55) Finding paradise at Brown: curiosity and lifelong learning(21:30) How meaningful small acts of encouragement can be(23:00) Enter Bill Campbell: how they met at Apple(34:00) The inner conflict: purpose vs. title(37:00) Managing through influence, not authority(39:30) Bringing the virtual-CEO model into venture capital(40:50) Success, skepticism, and earning trust at Kleiner(43:10) Why this? Why you? Why now?(44:30) “Is this worth failing at?”—the most important founder question(46:00) The gambler’s wisdom: inviting luck(48:30) How to make yourself luckier (excellence, flexibility, humility)(50:10) Most great companies succeed with Plan B, not Plan A(51:30) A painful miss: the Juicero story(53:00) PR mismatch, press backlash, and the fatal Bloomberg articleConnect with Alisa!Follow Alisa Cohn on Instagram: @alisacohnTwitter: @alisacohnFacebook: facebook.com/alisa.cohnLinkedIn: https://www.linkedin.com/in/alisacohn/Website: http://www.alisacohn.comDownload her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon