From Start-Up to Grown-Up

Jyoti Bansal, two-time founder who built AppDynamics and Harness, reflects on rebuilding after a billion-dollar exit. He discusses the founder identity reset and treating entrepreneurship as a craft. Hear his urgency around the AI transformation, how to operate in founder mode for rapid alignment, and why go-to-market and revenue discipline win against product-only strategies.

Gina Bianchini, founder and CEO of Mighty Networks and serial entrepreneur who builds digital communities. She explains why community—not audience size or content—drives transformation and retention. Short frameworks on purpose, structure, and weekly rituals. Practical tactics like daily prompts, give/ask rituals, and managing energy over time for lasting engagement.

Tanay Kothari, co-founder and CEO of Wispr Flow and three-time founder known for product-led AI work, shares his journey. He discusses pivoting from hardware to AI dictation. He talks about hard trade-offs like layoffs, separating vision from execution, leading people older than you, building fast feedback loops, and using AI to scale teams and support.

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.