From Start-Up to Grown-Up

From Start-Up to Grown-Up

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From Start-Up to Grown-Up episodes

  • 117: Jyoti Bansal, Two-Time Founder, How to Win the AI Race Before Your Competitors Catch Up

    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.

    You’ll learn:

    • Why a worse product can still beat you (and how to prevent it)
    • The hidden identity crisis founders face after a big exit
    • How to think of entrepreneurship as a craft, not a one-time event
    • Why startup growth is about milestones, not perfection
    • The real reason most companies fall behind during major tech shifts
    • How to operate in “founder mode” when speed is everything
    • The difference between product differentiation and go-to-market dominance
    • How to build a scalable sales machine (not just hire “charismatic closers”)
    • The hiring framework Jyoti uses to spot elite sales talent
    • How to align a company fast during high-pressure transformation
    • The “startup within a startup” model that creates ownership at scale
    • Why transparency in numbers builds accountability across the entire org

    We talk about:

    • 00:00 The uncomfortable truth after a billion-dollar exit
    • 02:00 Why Jyoti came back to build again
    • 05:00 The founder identity crisis no one prepares you for
    • 08:00 Entrepreneurship as a craft, not a single shot
    • 11:00 The milestone framework for building successful companies
    • 15:00 The AI transformation and why most companies will lose
    • 18:00 Founder mode, speed, and making decisions in real time
    • 22:00 Aligning teams when everything is changing fast
    • 26:00 Why revenue is the only truth in business
    • 29:00 Sales as a competitive advantage 
    • 32:00 The myth of “relationship-based” selling
    • 35:00 Building a scalable, structured go-to-market machine
    • 38:00 How to hire great sales leaders (and avoid getting sold in the interview)
    • 41:00 The onboarding mistake most founders make
    • 44:00 Transparency, numbers, and company-wide accountability
    • 47:00 The “startup within a startup” model explained
    • 52:00 Ownership, incentives, and building multiple winning products


    Follow Jyoti on

    • LinkedIn: https://www.linkedin.com/in/jyotibansal
    • Website:  ​https://www.harness.io/

    Connect with Alisa!

    Follow Alisa Cohn on 

    • Instagram: @alisacohn
    • Twitter: @alisacohn
    • Facebook: 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) 

    Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

    1 hr 3 min
  • 116: Gina Bianchini, Founder of Mighty Networks, Stop Building an Audience. Build Community Instead [ENCORE]

    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.

    You’ll learn:

    • Why community is the most powerful driver of transformation and results
    • The difference between an audience and a true community (and why it matters)
    • The simple framework behind high-engagement communities that actually last
    • How to structure your community for consistency, growth, and retention
    • Why giving advice kills engagement and what to do instead
    • The role of purpose in attracting and sustaining members
    • How founders can navigate doubt, feedback, and uncertainty
    • Why entrepreneurship is irrational, and how to stay grounded anyway
    • The real skill CEOs need to master, and it’s not what you think
    • How to manage energy, not just time, to lead effectively

    We talk about:

    • 00:00 Why community is the foundation of transformation
    • 02:30 The founding vision behind Mighty Networks
    • 05:00 Growing up in community and why it shaped everything
    • 12:30 Founder mental health and why it’s not for everyone
    • 14:00 Using mission to move through doubt and dark moments
    • 16:00 When investors don’t believe in your vision
    • 18:30 How to process feedback without losing your direction
    • 22:30 The core elements of building a powerful community
    • 29:30 The biggest mistake that kills community engagement
    • 31:00 Simple rituals that create deeper connection
    • 33:00 Why energy management matters more than time management
    • 36:00 The hidden cost of poor leadership energy
    • 38:00 Morning routines and protecting creative thinking time
    • 44:00 Agreements vs policies inside a company
    • 47:00 Building a human system, not a mechanical one
    • 50:00 What great leadership actually looks like in practice
    • 58:00 Advice for founders building something meaningful

    Follow Gina on

    • https://www.instagram.com/gbianchini/
    • https://www.linkedin.com/in/ginabianchini/
    • https://www.mightynetworks.com/

    Connect with Alisa!

    Follow Alisa Cohn on 

    • Instagram: @alisacohn
    • Twitter: @alisacohn
    • Facebook: 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) 

    Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

    1 hr 2 min
  • #115 – Tanay Kothari, Co-Founder & CEO of Wispr Flow: How a 27-Year-Old Founder Is Redefining Leadership, Product, and the AI Revolution

    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.

    You’ll learn:

    • What founders get wrong about vision vs. execution, and how to separate the two
    • How to navigate difficult decisions, including layoffs, without losing your integrity
    • How to lead and influence people who are more experienced than you
    • The power of aligning on beliefs instead of debating decisions
    • How to build faster, more effective teams through shared frameworks
    • What it really means to take responsibility as a founder
    • The trade-offs required to build a company, and how to choose them consciously
    • How emotional maturity becomes a leadership advantage
    • Why great leaders focus on how they show up, not just what they build

    We talk about:

    • 00:00 Building from a young age and what drives Tanay
    • 03:00 Early product thinking and what makes great products work
    • 06:00 The difference between vision and execution in startups
    • 09:00 Making hard decisions and leading through uncertainty
    • 12:00 The emotional reality of layoffs and responsibility as a founder
    • 16:00 The weight of leadership and the trade-offs of building a company
    • 23:00 Managing and leading people more experienced than you
    • 26:00 Why personalization matters in leadership (“love languages” for teams)
    • 29:00 Aligning on beliefs vs relying on authority
    • 35:00 Building decision-making frameworks that scale with your team
    • 41:00 How small systems unlock massive team productivity
    • 46:00 Why entry-level roles are disappearing and what replaces them
    • 49:00 Advice for young professionals in an AI-first world
    • 55:00 Creating fast feedback loops to build better products
    • 58:00 Why most companies build too many products too soon
    • 01:01:00 Imposter syndrome and the hidden pressure of leadership
    • 01:04:30 Final lessons on leadership, people, and building something that lasts

    Follow Tanay on

    • LinkedIn: https://www.linkedin.com/in/tankots/
    • Website: https://wisprflow.ai/

    Connect with Alisa!

    Follow Alisa Cohn on 

    • Instagram: @alisacohn
    • Twitter: @alisacohn
    • Facebook: 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) 

    Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

    1 hr 6 min
  • #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 it
    • The hidden damage caused by ruinous empathy
    • Why silence at work is more costly than discomfort
    • How to solicit feedback without triggering defensiveness
    • The difference between bias, prejudice, and bullying
    • How to “disrupt bias without disrupting the meeting”
    • How leaders can build psychological safety through vulnerability
    • Why upstanders matter and how to be one

    We talk about:

    • 00:00 The painful story behind Radical Candor and why silence cost more than honesty
    • 03:00 The Radical Candor framework explained: care personally + challenge directly
    • 08:00 Ruinous empathy and the real consequences of avoiding feedback
    • 12:00 Why soliciting feedback is the first leadership move
    • 18:00 How to ask for feedback without getting fake reassurance
    • 24:00 From Radical Candor to Radical Respect: what prompted the new book
    • 28:00 The two definitions of respect and why they matter
    • 31:00 Bias, prejudice, and bullying, simple definitions leaders can use
    • 35:00 How to disrupt bias without disrupting the meeting
    • 44:00 Managing shame and defensiveness when your bias is flagged
    • 51:00 The cost of silence and the power of being an upstander
    • 57:00 Why discomfort is the price of real collaboration


    Follow Kim on

    • Instagram: https://www.instagram.com/radicalcandorofficial
    • LinkedIn: https://www.linkedin.com/in/kimm4/
    • Medium: https://kimmalonescott.medium.com/ 
    • Website: https://kimmalonescott.com/ 

    Connect with Alisa!

    Follow Alisa Cohn on 

    • Instagram: @alisacohn
    • Twitter: @alisacohn
    • Facebook: 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) 

    Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

    1 hr 19 min
  • #113 – Matt Oppenheimer, from Founder to Public Company CEO of Remitly: Why Falling in Love with the Problem Builds Enduring Companies

    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 solution
    • How to balance curiosity with decisiveness as a leader
    • The difference between startup execution and public company leadership
    • How to design culture intentionally and evolve it over time
    • Why executive transitions are about stage-fit, not loyalty
    • What IPO readiness really requires behind the scenes
    • How to manage imposter syndrome and board pressure
    • Why psychological safety with investors matters
    • How “towering strengths” create leadership shadows
    • What it means to grow into the CEO your company needs

    We talk about:

    • 00:00 The origin of Remitly and identifying a global problem
    • 03:00 Grit, flexibility, and falling in love with the problem
    • 06:00 Growth mindset, curiosity, and listening to feedback
    • 10:00 Global perspective and customer centricity
    • 14:00 Designing culture from day one
    • 18:00 Evolving values as strategy evolves
    • 23:00 Hiring executives for stage, not sentiment
    • 28:00 Managing leadership transitions thoughtfully
    • 33:00 Founder development plans and 360 reviews
    • 36:00 Moving from “doing” to leading at scale
    • 42:00 IPO preparation and avoiding IPO as the sole goal
    • 46:00 Becoming a public company CEO
    • 49:00 Imposter syndrome and board dynamics
    • 53:00 Advice for founders scaling their leadership

    Follow Matt on

    • LinkedIn: https://www.linkedin.com/in/mattoppenheimer/
    • Website: https://www.remitly.com/

    Connect with Alisa!

    Follow Alisa Cohn on 

    • Instagram: @alisacohn
    • Twitter: @alisacohn
    • Facebook: 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) 

    Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

    55 min
  • #112 - Sal Di Stefano, Co-Founder of Mind Pump Media, How Authenticity, Cofounder Alignment, and Physical Strength Shape Great Leadership [ENCORE]

    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 tactic
    • How to recognize cofounder alignment before problems surface
    • Why being right can hurt teams and trust
    • How physical health supports better leadership decisions
    • What Mind Pump did differently to build loyalty and longevity

    We talk about:

    • 00:00 Leadership responsibility, health, and personal accountability
    • 01:00 Introducing Sal Di Stefano and Mind Pump Media
    • 03:00 Why long-form podcasting enabled real connection and trust
    • 05:10 Turning Mind Pump into a multi-revenue media business
    • 09:10 Building trust before monetizing and letting the audience lead
    • 13:45 Early revenue growth and turning down misaligned sponsors
    • 18:30 Finding the right cofounders and values alignment
    • 22:15 Conflict, disagreement, and committing as a team
    • 30:45 Navigating growth, the pandemic, and unexpected momentum
    • 36:10 Authenticity, vulnerability, and being recognized in public
    • 40:20 Boundaries, family, and redefining success as a leader
    • 45:00 Focus, leverage, and choosing what actually moves growth
    • 49:20 Serving existing customers before chasing new ones
    • 53:40 Why great leaders and coaches must be great communicators
    • 57:40 Final reflections on leadership, health, and the long game


    Follow Sal on

    • X: https://x.com/mindpumpsal
    • Podcast: https://mindpumppodcast.com/ 
    • Website: www.mindpumpmedia.com

    Connect with Alisa!

    Follow Alisa Cohn on 

    • Instagram: @alisacohn
    • Twitter: @alisacohn
    • Facebook: 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) 

    Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

    1 hr 23 min
  • #111 – Dr. Becky Kennedy on Why Great Leaders Stop Managing Feelings and Start Building Trust

    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 trust
    • Why setting boundaries often triggers guilt and how to tell guilt apart from emotional over-responsibility
    • How repair strengthens relationships more than getting it right the first time
    • How to handle defensiveness, emotional reactions, and resistance at work
    • Why scripts and practice reps are essential leadership skills, not crutches
    • How predictable conflict shows up at work and how to lead through it calmly
    • Why imposter syndrome never fully disappears and how to lead anyway

    We talk about:

    • 00:00 Why parenting is leadership training and why leadership is human work
    • 03:45 What sturdy leadership is and why extremes fail
    • 06:20 The “sturdy pilot” metaphor and how leaders create safety in turbulence
    • 10:30 Authority vs empathy, and why feelings should not dictate decisions
    • 14:40 Boundaries, guilt, and emotional over-responsibility at work
    • 18:50 Why empathy doesn’t mean absorbing other people’s emotions
    • 22:30 Handling defensiveness and emotional reactions in professional settings
    • 31:45 Predictable conflict, patterns, and solving the real issue
    • 36:10 Repair after rupture and why it builds trust faster than perfection
    • 42:30 How unrepaired moments erode connection and performance
    • 45:20 Imposter syndrome, self-leadership, and staying in the driver’s seat
    • 49:00 What Dr. Becky wishes she had known earlier about growth and leadership

    Follow Dr. Becky on

    • Instagram
    • YouTube
    • TikTok
    • Facebook
    • Website

    Connect with Alisa!

    Follow Alisa Cohn on 

    • Instagram: @alisacohn
    • Twitter: @alisacohn
    • Facebook: 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) 

    Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

    52 min
  • #110 Jim McKelvey, Cofounder of Square - Innovation When it's Your Only Choice, Overcoming Regulation, and Managing His Intern, Jack Dorsey [ENCORE]

    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 copycats
    • How Square started from a single lost sale and grew into a global company
    • What happens emotionally when you’re building something no one understands yet
    • Why copying best practices can fail when you’re solving a brand-new problem
    • Why mission-driven teams outperform money-driven ones over time

    We talk about:

    • 00:00 Why timing is everything, and why being “too early” still hurts
    • 05:30 The moment Square was born, one lost sale that changed everything
    • 10:00 Why the payments industry was designed to exclude small businesses
    • 16:30 Mission vs money, and why people joined even when they could leave
    • 20:00 Amazon launches a competing product, and Square’s unexpected response
    • 26:00 The Innovation Stack explained, and why it’s almost impossible to copy
    • 31:00 Panic attacks, pressure, and the nervous system cost of building
    • 35:30 Copying vs innovating, and where founders get trapped
    • 47:00 Imposter syndrome, even after success

    Follow Alisa Cohn on

    • Instagram: 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/scripts

    Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

    Connect with Alisa!

    Follow Alisa Cohn on 

    • Instagram: @alisacohn
    • Twitter: @alisacohn
    • Facebook: 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) 

    Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

    1 hr 5 min
  • #109 Robbie Bent cofounder of Othership— From Rock Bottom to Community Buildering Community

    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 website
    • X
    • Robbie on Instagram
    • Othership on Instagram
    • LinkedIn


    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 

    • Instagram: @alisacohn
    • Twitter: @alisacohn
    • Facebook: 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) 

    Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

    1 hr 19 min
  • #108 Semyon Dukach— MIT Blackjack Team Former Leader, Current VC, Invests Only in Immigrants

    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:

    • X
    • LinkedIn
    • One Way Ventures


    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 

    • Instagram: @alisacohn
    • Twitter: @alisacohn
    • Facebook: 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) 

    Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

    48 min

About From Start-Up to Grown-Up

From the publisher's feed

One of the top startup coaches in the world, Alisa Cohn, talks to founders, creators, advisors, investors and builders of all kinds about their insights and experiences in growing from Start-up to…

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