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What happens after you “make it”… and realize money was never the point?
In this episode, Jyoti Bansal, Founder & CEO of Harness and founder of AppDynamics (sold for $3.7B), sits down with Alisa Cohn for a conversation that cuts deeper than typical startup playbooks.
This is not just about building companies. It’s about what happens when the finish line disappears… and you have to decide who you are without it.
Jyoti shares the unexpected identity crisis that hit after his exit, why he chose to build again anyway, and what most founders misunderstand about success, sales, and staying relevant in a world that’s changing faster than your roadmap can keep up.
From the brutal reality of startup milestones to the urgency of the AI transformation, this episode is a masterclass in how to think, move, and lead when the stakes are real.
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What if the thing you’ve been told to build… isn’t the thing that actually creates results?
In this encore episode, Gina Bianchini joins Alisa Cohn to break down why community, not content, not audience size, not algorithms, is the real driver of transformation, retention, and long-term business growth.
This conversation goes far beyond theory. It’s a masterclass in how communities actually work, why most founders get it wrong, and what it really takes to build something people don’t just follow… but belong to.
Gina shares the exact frameworks behind thriving communities, the psychology of engagement, and the structure that turns passive consumers into active participants.
This is also a raw look at entrepreneurship behind the scenes, from navigating dark moments and doubt, to leading with mission instead of ego, to building something that feels inevitable before it’s proven.
If you’re building a brand, a business, or a movement, this episode will change how you think about growth.
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Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon
What does it actually take to lead when the stakes are real, the decisions are heavy, and people are counting on you?
In this episode of From Start-Up to Grown-Up, Alisa Cohn sits down with Tanay Kothari, Co-Founder and CEO of Wispr Flow, one of the most talked-about AI companies right now, to explore what it means to build, lead, and grow at a level most founders never reach.
Tanay may be a young founder, but the way he thinks about leadership, people, and decision-making is anything but early-stage. This conversation goes deep into the realities of building a company, not just the strategy, but the responsibility, the trade-offs, and the emotional weight that comes with it.
They unpack what founders often get wrong about vision versus execution, why the hardest decisions are usually the right ones, and how to lead teams through uncertainty without losing trust.
Tanay also shares his approach to managing people more experienced than him, why understanding how each individual wants to be led changes everything, and how aligning on beliefs, not just decisions, can transform how teams operate.
This is a conversation about leadership under pressure, building with intention, and becoming the kind of founder your company actually needs.
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Download her 5 scripts for delicate conversations (and 1 to make your life better)
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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.
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Download her 5 scripts for delicate conversations (and 1 to make your life better)
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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.
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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.
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Download 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.
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Download 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:
We talk about:
Follow Alisa Cohn on
Download her 5 scripts for delicate conversations (and 1 to make your life better): AlisaCohn.com/scripts
Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon
Connect with Alisa!
Follow Alisa Cohn on
Download 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:
Timestamps:
(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 Authenticity
Connect with Alisa!
Follow Alisa Cohn on
Download 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:
Timestamps:
(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 Entrepreneurship
Connect with Alisa!
Follow Alisa Cohn on
Download 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
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