From Start-Up to Grown-Up

Kim Scott, former Google and Apple exec and author of Radical Candor and Radical Respect, offers practical rules for feedback and respect at work. She explains caring personally while challenging directly. Short takes include why silence hurts, how to solicit feedback without triggering defensiveness, ways to disrupt bias in meetings, and tactics for being an effective upstander.

Matt Oppenheimer, co-founder and CEO of Remitly who led the company from startup to public markets. He recounts spotting the pain of international money transfers in Kenya. Short takes cover falling in love with the problem, evolving culture with strategy, hiring for stage-fit, navigating IPO readiness, and managing imposter syndrome and leadership transitions.

Sal Di Stefano, co-founder of Mind Pump Media and former gym owner turned fitness entrepreneur. He discusses building a multi-revenue media business from long-form content. He explains cofounder alignment, managing conflict by committing as a team, and why authenticity builds trust. He also links physical health and boundaries to stronger leadership.

Dr. Becky Kennedy, clinical psychologist and author of Good Inside, offers a mini bio as a parenting and leadership translator. She explores sturdy leadership: authority with empathy, holding boundaries without guilt, and repairing relationships after ruptures. Short, practical topics include handling defensiveness, using scripts and practice, navigating predictable workplace chaos, and leading despite imposter feelings.

Jim McKelvey, entrepreneur, glassblower, and Square cofounder, shares the wild origin of Square and the idea born from one lost sale. He explains the Innovation Stack and why true innovation often comes from necessity. He recounts battling competitors, building mission-driven teams, the personal toll of startup life, and lessons from glassblowing and unexpected leadership.

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, a former leader of the MIT Blackjack team and current founding partner at One Way Ventures, shares his fascinating journey from Soviet refugee to venture capitalist. He discusses his unique insights on backing immigrant founders, emphasizing their resilience and pattern recognition. Semyon also relates lessons from blackjack to entrepreneurship, highlights the importance of customer focus, and openly addresses imposter syndrome. With practical advice for founders, he makes a compelling case for the extraordinary potential of immigrant entrepreneurs.

Jonathan Wolf is the co-founder and CEO of ZOE, a visionary in personalized nutrition leveraging AI and microbiome research. In this engaging discussion, he delves into his journey from scaling Criteo to founding ZOE, revealing how a sabbatical led to a profound identity shift. He shares insights on the importance of naivety in innovation, raising €7 million in a matter of weeks, and the launch of ZOE's app for real-time food risk assessment. Jonathan emphasizes that the way we eat is not only broken but also fixable, sparking a revolutionary approach to nutrition.

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, a seasoned entrepreneur and investor at Kleiner Perkins, shares invaluable insights from his impressive career. He recounts transforming a challenging interview with Neil Young into a success by ditching the script. Randy also discusses the influence of his gambler father on his ability to read people, and highlights crucial signs to detect lies in entrepreneurs. He emphasizes the importance of self-awareness and shares the three ‘whys’ every founder must answer: why this, why you, and why now. A must-listen for aspiring founders!