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 Grown-up.
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128: Ken Davenport Produces Broadway Hits. Here's the Startup Playbook Behind Them
Monday, October 12, 2026 • Duration 44:58
Most people don’t know that producing a Broadway show is like building a startup. That’s what Tony Award-winning Broadway producer Ken Davenport has learned over his decades producing hits. He has to find the product, raise the capital, build the team, and get 1,000 to 2,000 people through the door eight times a week, for years. And when founders tell him their business is different, he tells them every business runs on the same principles.
Ken is a Tony and Olivier Award-winning producer whose credits include Once On This Island, Godspell, Oh, Mary!, and A Beautiful Noise: The Neil Diamond Musical. He was the first to use dial testing on a Broadway-bound musical, landing him on the front page of The New York Times, and he crowdfunded Godspell with $5 million from 737 investors before Kickstarter existed.
In this episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Ken to explore how he sees the potential in an idea before anyone else does, what he did when investors refused to write checks for a show he believed in, and why he raised money to build a marketing army, not just a budget.
This is a candid conversation about product development, fundraising, market research, taste, and leadership, with a rare look behind the curtain of Broadway.
You’ll learn:
Why Broadway producer Ken Davenport believes every business runs on the same principles
Why audiences choose the devil they know, and what that means for launching something new
How Ken develops his taste and keeps challenging it as audiences change
What Ken did when investors couldn't see the vision for Once On This Island
How dial testing and audience research shape a Broadway show before it reaches New York Why Ken crowdfunded Godspell to build a marketing army, not just raise money
How Ken uses AI to find patterns in reviews and audience data without replacing the artist
Why founders should seek out rooms where they are not the smartest person, and how Ken handles imposter syndrome
We talk about:
00:00 Meet Tony Award-winning Broadway producer Ken Davenport 01:52 How seeing Les Mis at 16 changed everything 06:03 Why a Broadway producer is really a startup founder 07:07 How do you find a hit the market can't explain yet 11:13 Developing taste in the age of AI 16:41 What do you do when investors won't write the check 19:49 Market testing and the first dial test on Broadway 24:00 Crowdfunding Godspell to build a marketing army 27:08 Marketing stunts that match the artistic message 30:00 How Ken Davenport uses AI without replacing the artist 36:23 Growing into a leader as an introverted extrovert 40:43 Imposter syndrome, showing face, and advice for founders
127: Jayson Gaignard Was $250K in Debt. Relationships Helped Him Rebuild
Monday, September 21, 2026 • Duration 59:13
What if the most valuable asset you can build as an entrepreneur is not your company, but your relationships?
Jayson Gaignard built one of Canada’s largest ticket-wholesaling businesses, only to realize he had created a company he hated. When circumstances left him approximately $250,000 in debt, with a six-month-old daughter and a new marriage, he began investing in the one thing no one could take from him: his relationships.
That decision eventually led Jayson to create MMT, an invite-only entrepreneurial community built around intentional connection, carefully curated experiences, and the belief that success should never be pursued alone.
In this episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Jayson to explore how entrepreneurs can build meaningful professional relationships, make the most of conferences, overcome social anxiety, and develop the courage to enter rooms where they do not yet feel they belong.
Jayson also shares the story behind buying 4,000 copies of Tim Ferriss’s book, his “eight seconds of courage” strategy for doing intimidating things, and the leadership decision that put nearly $2 million at risk during the pandemic.
This is a candid conversation about entrepreneurial community, relationship building, leadership, discomfort, comparison, and why proximity to the right people can change the trajectory of your life.
You’ll learn:
How Jayson turned a financial and personal crisis into a new entrepreneurial path
Why meaningful relationships are among the safest investments a founder can make
How to build an aspirational network before you have status or connections
Why attending the right events can accelerate years of relationship building
How to prepare for conferences and follow up before the excitement fades
How “eight seconds of courage” can help you move through social anxiety
Why MMT prioritizes character and connection over financial success
How Jayson made an integrity-driven decision involving nearly $2 million
Why comparison can quietly damage otherwise meaningful relationships
126: Joe Thomas Took Loom From 14 Days of Runway to a $1B Acquisition [ENCORE]
Monday, September 7, 2026 • Duration 01:07:44
How did Joe Thomas and his co-founders keep building Loom when they had maxed-out credit cards and only 14 days of runway left?
Before Loom became one of the most recognizable asynchronous video platforms, Joe Thomas, Vinay Hiremath, and Shahed Khan spent nine months testing ideas, making major pivots, and listening closely to early users. Their persistence eventually transformed a struggling user-feedback product into a new way for people to communicate at work.
In this encore episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Joe to explore Loom’s earliest days, the approximately 100 fundraising rejections that strengthened his pitch, and the leadership lessons he learned while scaling the company.
Joe also reveals why Loom defined its values when the team had only seven people, how meditation helped him make better decisions, and why founders must become comfortable doing the work they would naturally rather avoid.
This is a candid conversation about resilience, fundraising, company culture, asynchronous leadership, and what it takes to grow from founder to CEO.
You’ll learn:
How Joe Thomas and his co-founders discovered the idea for Loom
How Joe improved his fundraising skills after approximately 100 rejections
Why founders often avoid the responsibilities that make them uncomfortable
How Loom defined its company values with only seven employees
Why values become most important during difficult decisions
How meditation helped Joe become less reactive as a leader
Why giving difficult feedback can be an act of belief
How leaders can protect their energy while building a company
When to communicate asynchronously and when to hold a meeting
Why discomfort is an unavoidable part of growing into a leader
We talk about:
00:00 Meet Joe Thomas, co-founder of Loom
01:27 The original idea behind video communication at work
04:20 Nine months of experimentation, customer conversations, and pivots
125: Seth Levine on Rebuilding Your Company for the AI Era From Scratch
Monday, August 24, 2026 • Duration 01:04:52
What if the biggest mistake CEOs are making with AI is trying to improve the company they already have?
Seth Levine believes leaders need to ask a more radical question: If you were building your company from scratch today, how would you design it?
Seth is a founder, investor, author, and co-founder of Foundry, the venture capital firm he built alongside Brad Feld and their partners. After decades of working with founders, boards, and leadership teams, he has seen what separates businesses that adapt from those that remain anchored to the way things have always been done.
In this episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Seth to explore how CEOs should approach AI transformation, why incremental efficiency is not enough, and what it takes to rethink an organization from the ground up.
Seth also shares the rarely told story behind Foundry’s creation, including the fifth founding partner who ultimately left the firm, the difficult conversation that ended a close friendship, and the months of rejection Seth and his partners endured while attempting to raise their first fund. At one point, Seth believed he had lost his family’s entire life savings. One pivotal yes changed everything, helping Foundry close a $225 million fund.
This is a candid conversation about building boldly, leading intentionally, and creating enough space to breathe along the way.
You’ll learn:
The most important AI question every CEO and board should be asking
Why using AI to improve productivity is not the same as becoming AI-native
How legacy workflows prevent established companies from transforming
Why CEOs need firsthand experience with emerging AI tools
How Foundry used coaching to build a healthier partnership from the beginning
How to prepare for a difficult leadership conversation
Why Foundry’s first fund nearly failed before closing at $225 million
How one significant yes can change the momentum of a fundraising process
The three qualities Seth sees in the most successful founders
How intentionality helps leaders remain bold without burning themselves out
124: Alex Lieberman Built Morning Brew to $75M. But That Was Just the Start [ENCORE]
Monday, August 10, 2026 • Duration 01:03:40
What comes after you build and sell the company that has defined your entire adult life?
Alex Lieberman co-founded Morning Brew as a college student after noticing that traditional business news felt dense, dry, and disconnected from the way young professionals wanted to consume information. What began as a Microsoft Word document emailed to a small group of students grew into one of the world’s most recognizable business media brands and ultimately led to a reported $75 million deal.
But the exit was not the end of Alex’s entrepreneurial journey. It became the beginning of a deeper conversation about identity, leadership, purpose, and what success is actually supposed to feel like.
Alex is now on his new entrepreneurial journey building Tenex, an AI transformation consulting firm.
In this episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Alex to unpack the decisions behind Morning Brew’s growth. Alex shares why he walked away from his dream job at Morgan Stanley, how he found a co-founder whose strengths complemented his own, and what he learned when the business needed him to evolve from a builder into an operational CEO.
This is an honest, thoughtful conversation about building something remarkable while remembering that your company is something you do, not the entirety of who you are.
You’ll learn:
How Alex Lieberman transformed a college newsletter into Morning Brew
Why early reader behavior revealed that the idea had real potential
Why regret minimization helped him make a life-changing decision
What happened behind the scenes during Morning Brew’s acquisition
Why the $75 million exit felt different from what Alex expected
How OCD and panic attacks affected Alex’s experience as a founder
Why founders can struggle with identity after an exit or leadership transition
How to build a “purpose portfolio” beyond your professional title
How to choose an executive coach for your current challenges
123: GiaNina Paolantonio Has Millions of Followers. Here’s the Business Behind Them
Monday, July 27, 2026 • Duration 01:02:05
GiaNina Paolantonio has spent most of her life in the spotlight. She made her Broadway debut in Matilda the Musical at nine, appeared in The Greatest Showman and Dance Moms, and built an online audience of millions. But behind the performances, viral videos, and global following is something much bigger: a multi-channel business built around dance, creativity, and authenticity.
Today, GiaNina’s business includes social content, brand partnerships, dance education, collaborations with artists and record labels, and a global teaching tour developed and managed alongside her family.
In this episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with GiaNina to explore the business behind being a creator. GiaNina shares how one sold-out dance class became an international opportunity, why she refuses to let one niche define her career, and how she monetizes her audience without promoting products or partnerships she does not believe in.
This is an honest look at what it takes to turn creative talent and online influence into an enduring business without losing yourself along the way.
You’ll learn:
How GiaNina transformed dance and social media into a multi-channel business
Why one sold-out class became the foundation of a global teaching tour
How she evaluates brand partnerships and confidently turns down lucrative deals
Why refusing to stay in one niche may create greater career longevity
What creators must understand about contracts, exclusivity, and content rights
How she manages public criticism, overwhelm, and competing demands
Why authenticity is the foundation of her brand and long-term strategy
We talk about:
00:00 Meet GiaNina Paolantonio
01:40 Going from the couch to Broadway at nine years old
06:00 Turning social media momentum into a career
08:20 Why GiaNina refuses to be confined to one niche
11:45 Building multiple revenue streams around dance and content
122: The Kettle & Fire Founder Is Fixing How America Pays for Health | Justin Mares, Co-Founder and CEO of Truemed
Monday, July 13, 2026 • Duration 47:47
Justin Mares built Kettle & Fire into one of the best known bone broth brands in the country. Then he walked away from it to go after something a lot less exciting on paper: the red tape standing between Americans and the preventive health products that actually keep them well.
His new company, Truemed, gives people a simple way to use money they already have set aside for health on things like workouts, better food, and sleep, instead of letting it sit unused or only get spent once they're already sick.
Alisa Cohn, executive coach and author of From Start-up to Grown-up, sits down with Justin to talk about why he left a thriving consumer brand to go build something in one of the most regulated, paperwork heavy industries there is. You'll hear how he tests ideas before he feels ready, how he hires for real mission alignment, why he chose venture capital this time around after largely bootstrapping Kettle & Fire, and how he still wrestles with imposter syndrome four companies in.
You’ll learn:
Justin Mares walked away from Kettle & Fire, one of the best known bone broth brands in the country, to go build Truemed instead.
Launching an imperfect product, like Justin's ghost landing page for Kettle and Fire built on $500 of ads, beats waiting for a perfect one.
Justin chose venture capital over bootstrapping Truemed after growing Kettle and Fire to hundreds of millions in revenue on less than $10 million raised.
Hiring your first five to ten people purely for mission alignment shapes every hire that follows, including Truemed's best employee, who found the company through Justin's newsletter.
Andreessen Horowitz brought Truemed access to founders and operators that a bootstrapped CEO could never reach cold, well beyond the capital itself.
Justin still deals with imposter syndrome after twelve years and four companies, and uses a specific reframe to move from doubt into action.
Justin believes startups are fundamentally momentum games, and wishes he had learned to trust his own judgment earlier in his career.
We talk about:
00:00 Justin Mares introduces Truemed and its preventive health mission
121: Founder Mode on Bitcoin: Double the Volatility, Double the Stakes | Will Reeves, Co-Founder and CEO of Fold
Monday, June 29, 2026 • Duration 50:33
Building a startup on Bitcoin means you're not riding one rollercoaster, you're riding two at once. The volatility of launching a company is hard enough. Layer on top of that a protocol still finding its own product-market fit, and you get a compounding effect that will break founders who aren't prepared for it.
Will Reeves knows this firsthand. He co-founded Fold, lived through deep bear markets with no investor interest in sight, made a critical pivot after realizing he was building the wrong solution, and took Fold public on Nasdaq in February 2025 as the first Bitcoin financial services company on the exchange.
In this episode of From Start-Up to Grown-Up, host Alisa Cohn sits down with Will Reeves, Co-Founder and CEO of Fold, to explore the real cost of building on Bitcoin, why "growth at all costs will destroy you," how a Starbucks line changed everything for Fold, what shifts the moment you go public, and the one truth about imposter syndrome most founders will never admit.
You’ll learn:
Why building a company on top of Bitcoin creates a compounding risk that most founders and investors seriously underestimate
The exact moment Will realized Fold was solving the wrong problem, and how the pivot unlocked real product-market fit and landed Visa as their first major partner.
Why "growth at all costs" is uniquely dangerous for Bitcoin companies, and what it actually looks like to build a business for long-term survival
What changed when Fold went public
How to spot when an executive has stopped scaling with the company
What imposter syndrome actually feels like from inside a public company CEO role
We talk about:
00:00 Why building on Bitcoin means you're riding two rollercoasters at once 04:03 Is resilience something you're born with or something you build over time? 06:37 The advice Will gives founders on withstanding the startup journey day to day 09:32 How Fold realized it was solving the wrong problem, and what they did about it 13:22 How do you get your team on board when you've found a new direction? 15:04 What Bitcoin is really for: decentralization, inflation, and financial freedom 22:23 Why growth at all costs will destroy you when you're building on Bitcoin 24:41 Why Fold went public via SPAC and what that decision looked like from the inside 33:03 The painful lesson of replacing yourself as a founder CEO 39:18 The lowest lows and highest highs of building Fold 43:13 Have you ever experienced imposter syndrome? Will's honest answer 46:43 Advice for founders on building a company and a life at the same time
120: Miro's Founder on Reinventing a 100-Million-User Company | Andrey Khusid, Founder of Miro
Monday, June 15, 2026 • Duration 46:40
What happens when you've already built a company used by more than 100 million people, and suddenly the world changes again?
In this episode, Alisa Cohn sits down with Andrey Khusid, Founder and CEO of Miro, to explore one of the biggest leadership challenges founders face: reinventing a successful company while it's still growing.
As AI transforms the way teams work, Andrey shares how Miro evolved from a digital whiteboard into a collaborative platform where humans and AI agents create together. He explains why founders must embrace "day one thinking," how to build startup energy inside a 1,600-person organization, and why many leaders struggle when shifting between founder mode and CEO mode.
The conversation dives deep into innovation, company culture, organizational transformation, leadership chemistry, experimentation, and what it really takes to stay relevant when technology changes faster than ever.
If you're a founder, CEO, executive, or entrepreneur navigating growth, change, or AI disruption, this episode offers a masterclass in adapting without losing your mission.
You’ll learn:
Why Andrey believes every company is now searching for product-market fit again
How AI is changing the future of collaboration and teamwork
What "day one thinking" means and why founders need it
The difference between experimentation in scaling versus reinvention
Why conviction matters more than consensus in zero-to-one innovation
How founders can communicate vision when they can't fully articulate it yet
The biggest mistake leaders make when trying to innovate inside large organizations
Why founder mode and CEO mode are both essential leadership skills
How AI is reshaping management, teams, and organizational design
The surprising reason culture becomes weaker as companies scale
Why entrepreneurial talent is becoming more valuable than specialized expertise
How to create startup energy inside an established business
The role of trust, feedback, and productive conflict in high-performing teams
Why leadership chemistry matters more than most executives realize
119: Eric Ries, Author of The Lean Startup, The Corporate Governance Crisis No One Wants to Admit
Monday, June 1, 2026 • Duration 48:51
What if the biggest threat to your company is not competition, but the systems everyone told you to trust?
In this episode, Alisa Cohn sits down with Eric Ries, creator of the Lean Startup methodology and bestselling author of The Lean Startup, The Startup Way, and Incorruptible, for a conversation about leadership, corporate governance, innovation, and why so many modern companies lose their way as they grow.
Eric unpacks the dangerous side of “best practices,” why shareholder primacy often destroys long-term value, and how financial pressure quietly reshapes company culture from the inside out. He also shares the untold story behind Costco’s governance model, why Anthropic’s structure matters in the AI race, and what founders misunderstand about speed, alignment, and leadership integrity.
You’ll learn:
Why many “best practices” are actually value destroying
What Eric Ries means by “financial gravity”
How companies lose their mission after founders lose control
Why Costco became one of the strongest governance models in business
The hidden danger of shareholder primacy
Why trustworthiness may be the most underrated asset in business
How Lean Startup was misunderstood by most founders
The real purpose behind MVPs and rapid experimentation
Why principles create faster companies, not slower ones
How aligned teams move faster with less management overhead
What Anthropic is doing differently with AI governance
Why constraints often create breakthrough innovation
The leadership lesson Eric learned from nearly compromising his own principles
How founders can build companies their grandchildren will be proud of
We talk about:
00:00 Why Eric Ries says builders are “under siege” 02:00 The hidden problem with modern business “best practices” 05:00 Why shareholder primacy destroys long-term companies 08:00 The untold Costco and Sol Price story 12:00 How Costco built a governance fortress 16:00 Understanding “financial gravity” inside organizations19:00 Why Costco shareholders defended leadership decisions22:00 The problem with management entrenchment24:00 Why corporations should function more like balanced systems26:00 Anthropic’s governance structure and AI leadership30:00 Why checks and balances do not kill innovation32:00 The real philosophy behind Lean Startup35:00 Why principles create speed inside organizations38:00 The overlooked role of trust and alignment40:00 Why great leaders intentionally make things harder42:00 The danger of compromising on core values44:00 Eric’s hardest leadership decision46:00 What founders misunderstand about success and power47:00 How to build companies designed to last generations
How founders can balance ambition with their health and long-term well-being
We talk about:
00:00 Meet Jayson Gaignard, founder of MMT and author of Community Made
03:12 Building a successful business he ultimately hated
05:00 Facing $250,000 in debt and searching for what came next
06:00 Why Jayson began investing in relationships
07:00 Buying 4,000 copies of Tim Ferriss’s book
09:16 Using regret minimization to make difficult decisions
12:00 How the right room can change your life
16:06 Building an aspirational network from scratch
22:22 How to make the most of conferences and large events
28:15 Managing social anxiety through preparation
29:45 Using eight seconds of courage to do hard things
34:07 Why personal growth requires discomfort
37:47 Building MMT as an invite-only entrepreneurial community
42:48 Leading a community like a company
45:15 Making a nearly $2 million decision during the pandemic
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