From Start-Up to Grown-Up

128: Ken Davenport Produces Broadway Hits. Here's the Startup Playbook Behind Them Oct 12, 2026 2698 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 the

127: Jayson Gaignard Was $250K in Debt. Relationships Helped Him Rebuild Sep 21, 2026 3553 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

126: Joe Thomas Took Loom From 14 Days of Runway to a $1B Acquisition [ENCORE] Sep 7, 2026 4064 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-

125: Seth Levine on Rebuilding Your Company for the AI Era From Scratch Aug 24, 2026 3892 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 o

124: Alex Lieberman Built Morning Brew to $75M. But That Was Just the Start [ENCORE] Aug 10, 2026 3820 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 mo

123: GiaNina Paolantonio Has Millions of Followers. Here’s the Business Behind Them Jul 27, 2026 3725 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 bus

122: The Kettle & Fire Founder Is Fixing How America Pays for Health | Justin Mares, Co-Founder and CEO of Truemed Jul 13, 2026 2867 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 lik

121: Founder Mode on Bitcoin: Double the Volatility, Double the Stakes | Will Reeves, Co-Founder and CEO of Fold Jun 29, 2026 3033 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 dee

120: Miro's Founder on Reinventing a 100-Million-User Company | Andrey Khusid, Founder of Miro Jun 15, 2026 2800 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 Mir

119: Eric Ries, Author of The Lean Startup, The Corporate Governance Crisis No One Wants to Admit Jun 1, 2026 2931 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 a

118: Josh Reeves, Co-Founder and CEO of Gusto, The 3-Part Alignment Framework Every Founder Needs Before Their Next Hire [ENCORE] May 18, 2026 3966 What if you have been hiring wrong this entire time?In this episode, Josh Reeves, Co-Founder and CEO of Gusto, a $10B people platform serving over 300,000 businesses, joins Alisa Cohn for one of the most practical and deeply human conversations about building teams that actually work.This is not a generic leadership talk. This is a masterclass in how to hire people who genuinely care, how to scale

117: Jyoti Bansal, Two-Time Founder, How to Win the AI Race Before Your Competitors Catch Up May 4, 2026 3751 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

116: Gina Bianchini, Founder of Mighty Networks, Stop Building an Audience. Build Community Instead [ENCORE] Apr 20, 2026 3674 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, wh

#115 – Tanay Kothari, Co-Founder & CEO of Wispr Flow: How a 27-Year-Old Founder Is Redefining Leadership, Product, and the AI Revolution Apr 6, 2026 3926 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 f

#114 - Kim Scott, Radical Respect and Radical Candor: How to Build Teams That Challenge Directly and Care Personally [ENCORE] Mar 23, 2026 4716 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 “disrup

#113 – Matt Oppenheimer, from Founder to Public Company CEO of Remitly: Why Falling in Love with the Problem Builds Enduring Companies Mar 9, 2026 3280 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

#112 - Sal Di Stefano, Co-Founder of Mind Pump Media, How Authenticity, Cofounder Alignment, and Physical Strength Shape Great Leadership [ENCORE] Feb 23, 2026 4971 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 nea

#111 – Dr. Becky Kennedy on Why Great Leaders Stop Managing Feelings and Start Building Trust Feb 9, 2026 3099 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

#110 Jim McKelvey, Cofounder of Square - Innovation When it's Your Only Choice, Overcoming Regulation, and Managing His Intern, Jack Dorsey [ENCORE] Jan 27, 2026 3851 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 c

#109 Robbie Bent cofounder of Othership— From Rock Bottom to Community Buildering Community Jan 12, 2026 4736 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 busin

#108 Semyon Dukach— MIT Blackjack Team Former Leader, Current VC, Invests Only in Immigrants Dec 30, 2025 2866 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 o

#107 Jonathan Wolf— Co-Founder and CEO of ZOE: The Growth of a Founder, the Most Important Leadership Skills, and How to Raise 7 Million Euros in 3 Weeks (Encore) Dec 15, 2025 2646 Jonathan Wolf is the co-founder and CEO of ZOE, the science-based nutrition company using data to transform how people eat. In this candid conversation, he joins me to explore what it takes to build a mission-driven company, how to lead with more clarity and transparency, and why the way we eat is more broken and more fixable than most people think.ZOE’s origin story is as unconventional as it is

#106 Kass and Mike Lazerow— Serial Married Founders Sold their Company to Salesforce for $750M on Loving the Journey (Encore) Dec 1, 2025 5335 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 b

#105 Randy Komisar— Legendary Kleiner Perkins Investor Shares the 3 “Whys” Every Founder Must Answer (Encore) Nov 18, 2025 4186 Randy Komisar is an entrepreneur and investor at Kleiner Perkins.Previously, he was a co-founder of Claris Corp., served as CEO for LucasArts Entertainment and Crystal Dynamics, and acted as “virtual CEO” for such companies as WebTV and GlobalGiving. Randy also served as CFO of GO Corp. and as senior counsel for Apple Computer, following a private practice in technology law.Randy is a founding dir

#104 Issac Evans— How a Series D CEO Found Product-Market Fit, Stays Self-Aware, and Survived His Bank Melting Dow Nov 4, 2025 4126 In this episode, Alisa Cohn interviews Isaac Evans, co-founder and CEO of Semgrep, a startup giving security tools directly to developers. Isaac shares his journey from conducting research at the U.S. Defense Department and MIT Lincoln Laboratory, where he explored binary exploitation bypasses, control-flow integrity, and novel hardware defenses on architectures like RISC-V, to founding and leadin

#103 Patrick Lee— Rotten Tomatoes Founder: The Secrets to Building an Enduring Business Oct 20, 2025 4618 Patrick Lee is best known as the co-founder and founding CEO of Rotten Tomatoes, the groundbreaking review platform that reshaped how audiences connect with movies and television. What started as a side project born out of his love for film became a global authority that continues to influence critics, fans, and the entertainment industry.In this conversation, Patrick shares his journey from runni

#102 Robert Glazer — Serial Entrepreneur on the Most Important Tool for Success Oct 7, 2025 4041 Robert Glazer is the founder of Acceleration Partners, a serial entrepreneur, bestselling author, and a leading voice on how values shape leadership. In this episode, Bob shares why stepping down from the company he built triggered a surprising crisis of meaning, how that experience led him to write The Compass Within, and how helping people clarify their core values has become his new personal mi

#101 Nick Huber — Building Wealth in “Boring” Businesses Sep 22, 2025 4230 Nick Huber is an entrepreneur and real estate investor who resides in Athens, Georgia, with his wife and three children. He owns Somewhere.com, Bolt Storage, RE Cost Seg, and several other businesses. His real estate portfolio currently includes sixty-eight self-storage properties, covering two million square feet. His portfolio of companies employs over 325 people and makes over $35 million annua

#100 Arvind Jain, Founder of Glean — From Technical Leader to First-Time CEO, the Business Case for Culture and Selling as a Founder’s Superpower Sep 8, 2025 3208 Arvind Jain is the founder and CEO of Glean, the Work AI platform that connects to all your company’s data so you can find, create, and automate anything. In this episode, Arvind shares his journey as a second-time founder and first-time CEO, reflecting on the challenges of moving from a deeply technical role into leading an organization.He talks about why selling is one of the most important skil

#99 Naveen Verma — From Princeton Professor to Venture-Backed CEO, Fundraising Without a Network, and Leading Firmly and Empathetically Aug 25, 2025 4071 Naveen Verma is a professor of electrical and computer engineering at Princeton and the co-founder and CEO of EnCharge AI, a startup building radically energy-efficient computers for artificial intelligence. In this episode, Naveen shares how his academic research into in-memory computing evolved over six years into a venture-backed company that’s rethinking the physical limits of AI computers.Nav

#98 3-time founder Craig Walker — From Selling Door-to-Door to 3-time founder; Building Google Voice; and the Real Trade-offs of Entrepreneurship Aug 11, 2025 3729 Craig Walker is the founder and CEO of Dialpad, a business communications platform powered by AI. A former M&A lawyer turned serial entrepreneur, Craig previously co-founded GrandCentral (acquired by Google and relaunched as Google Voice) and sold his prior company to Yahoo. In this episode, Craig shares how his career unfolded from door-to-door dictation sales to running a 1,500-person compan

#97 Brad Feld, Founder of Techstars - Lessons from Techstars, why you should have “random” meetings, and the value of the “Give First” mentality. Jul 29, 2025 4081 Brad Feld has spent over 40 years building companies, mentoring founders, and investing in the startup ecosystem. He’s the co-founder of Techstars, a prolific venture capitalist, and the author of nine books. In this episode, Brad opens up about the mental reset that came with turning 60, why he stopped chasing “more,” and what led him to dust off a book draft about mentorship that had been sittin

#96: David Heinemeier Hansson, Co-Owner of 37signals— Creating with first principles, acting with courage, and working in a world with no managers (Repost) Jul 17, 2025 4828 David is the creator of Ruby on Rails, Co-Owner of 37signals, best-selling author, Le Mans class-winning racing driver, antitrust advocate, investor in Danish startups, frequent podcast guest, and family man.He writes regularly on HEY World and speaks on The REWORK Podcast. Hundreds of thousands of programmers around the world have built amazing applications using Ruby on Rails, an open-source web

#95: From Startup to Grown-Up: Bob Young, co-founder of Red Hat - The origin of Open Source; the key to life and startup success, and how failure can fuel you. Jul 1, 2025 4547 Bob Young co-founded Red Hat, the first company to build a successful business around open source software, and helped shape the modern internet in the process. In this episode, Bob shares the story of how Red Hat went from a CD in a Ziploc bag to a billion-dollar business that inspired GitHub, Coinbase, and much of the cloud infrastructure we use today.But this conversation is about more than jus

#94: From Startup to Grown-Up: Jonathan Wolf, co-founder and CEO of ZOE - The growth of a founder, the most important leadership skills, and how to raise 7 million euros in 3 weeks. Jun 17, 2025 4537 Jonathan Wolf is the co-founder and CEO of ZOE, the science-based nutrition company using data to transform how people eat. In this candid conversation, he joins Alisa to explore what it takes to build a mission-driven company, how to lead with more clarity and transparency, and why the way we eat is more broken and more fixable than most people think.ZOE’s origin story is as unconventional as it

#93: From Startup to Grown-Up: Kass and Mike Lazerow, Serial founders; co-founders of Buddy Media (sold to Salesforce for $750M) - How to survive a failed acquisition, stay married to your co-founder, and enjoy the journey of entrepreneurship. Jun 2, 2025 5335 Kass and Mike Lazerow are serial entrepreneurs, seasoned investors, and co-authors of the upcoming book Shoveling Sh!t: A Love Story About the Entrepreneur’s Messy Path to Success. They join Alisa to share an unfiltered look at what it really takes to build companies, navigate chaos, and stay married through it all.Known for founding Golf.com and Buddy Media, which they sold to Salesforce for $745

#92: From Startup to Grown-up: David Ko, CEO of Calm — from gaming to mental health, tools to combat burnout, and the rituals you can use in your own meetings May 19, 2025 3126 David Ko is the CEO and board member of Calm, the #1 app for sleep, meditation, and mindfulness. A former healthcare executive and tech operator, David previously served as COO of Zynga, held senior roles at Yahoo!, and founded a healthtech company acquired by Calm. He is the bestselling author of Recharge, and has been recognized by TIME, LinkedIn, RockHealth, and NYU Stern for his leadership in

#91: From Startup to Grown-up: Mike Seckler, CEO of Justworks — how to run a great board process, how to avoid self-inflicted wounds, and the value of taking big risks early in your career May 6, 2025 4918 Mike Seckler is a two-time entrepreneur and tech startup founder who led a company through the dot-com boom and bust, and now leads the charge as CEO of Justworks, the HR tech company focused on uplifting small businesses. In this conversation, he shares hard-earned lessons from building one of the earliest SaaS HR startups, navigating turbulent markets, and guiding Justworks through major transit

#90: From Startup to Grown-Up: Jeff Byers, Co-founder and CEO of Momentous — Transitioning from NFL player to CEO, managing cultural clashes during a merger, and navigating the high-pressure world of growth-stage leadership Apr 21, 2025 4300 Jeff Byers is the co-founder and CEO of Momentous, a high-performance wellness company delivering science-backed products used by elite athletes, military operators, and high-performers worldwide. A former NFL player and two-time USC football captain, Jeff brings both personal and professional insight to optimizing performance and building values-driven companies.What you’ll learn:Why Jeff says ef

#89: From Startup to Grown-Up: Kevin Evers, author of There’s Nothing Like This: The Strategic Genius of Taylor Swift — unpacking Taylor Swift’s rise to the top; when to take big risks; and how to build a rabid fan base Apr 8, 2025 3286 Kevin Evers is a Senior Editor at Harvard Business Review, where he shapes groundbreaking research and develops award-winning and bestselling books on high performance, creativity, innovation, marketing, and digital disruption. He’s also written popular essays on brain science, persuasion, unpredictability, and the power of storytelling.Kevin holds degrees in English and Film Studies, and his fort

#88: From Startup to Grown-Up: Eddie Kim, Co-founder and CTO of Gusto - Wearing different “hats” as a leader; learning to get his hands off the keyboard and enable others instead; and how to build a growth mindset Mar 25, 2025 2588 Eddie Kim is the CTO and cofounder of Gusto, which serves 400,000+ small and medium-sized businesses nationwide by helping them onboard, pay, insure, engage, and provide benefits for their teams, in one integrated, friendly, and easy-to-use platform. Eddie’s career has been shaped by chance encounters, a passion for software, and a deep commitment to growth. Before Gusto, he launched his first com

#87: How Daniel Yanisse Scaled Checkr to $700M+ and Overcame the Post-Hypergrowth Crisis Mar 11, 2025 2531 In this episode of From Start-Up to Grown-Up, host Alisa Cohn sits down with Daniel Yanisse, co-founder and CEO of Checkr, to discuss the exhilarating rise and the challenges of sustaining a high-growth company. Checkr revolutionized the background check industry, scaling from a $1M revenue run rate in just three months to processing millions of background checks annually. But with hypergrowth cam

#86: Peter Attia, MD, Founder of Early Medical — improving your lifespan and healthspan, the centenarian decathlon, and the process of making major life changes (Repost) Feb 25, 2025 2669 Peter Attia, MD, is the founder of Early Medical, a medical practice that applies the principles of Medicine 3.0 to patients with the goal of lengthening their lifespan and simultaneously improving their healthspan. He is the host of The Drive, one of the most popular podcasts covering the topics of health and medicine. Dr. Attia received his medical degree from the Stanford University School of M

#85: Isabelle Freidheim, Founder of Athena Capital — The benefits of being an only child, creating opportunities for women in finance, and unlocking hidden talent Feb 11, 2025 4173 Isabelle Freidheim is the founder and managing partner of Athena Capital. She is the youngest chairman of a publicly traded company in the U.S. In her role as managing partner of Athena Capital, Freidheim oversees the company's strategic direction and leads its efforts in identifying and investing in technology companies.Freidheim is an entrepreneur and investor with more than 15 years of exp

#84: Ethan Evans, Executive Mentor and Former Amazon VP — Managerial myths debunked, how to create a safety net for your career, and why everyone should write online Jan 28, 2025 3066 During his 15+ years at Amazon, Ethan Evans helped invent Prime Video, Amazon Video, Amazon Appstore, Merch by Amazon, Prime Gaming (formerly Twitch Prime), and Twitch Commerce. He led global teams of over 800 and holds more than 70 patents. Ethan has reviewed 10,000+ resumes, conducted 2,500+ interviews, made 1,000+ hires, and was an Amazon Bar Raiser and Bar Raiser Core Leader, responsible for t

#83: Chip Conley, Founder at Modern Elder Academy — Using regret as fuel; how and why founders need to shift their identities; how to manage people older than you; and his favorite interview question (Repost) Dec 31, 2024 4472 Chip is the founder of the Modern Elder Academy (MEA), where a new roadmap for midlife is offered at a beautiful oceanfront campus in Baja California Sur, Mexico, and forthcoming campuses in Santa Fe, NM. His five books have made him a leading authority at the intersection of psychology and business. Chip had tons of wisdom to share in this talk, including how to use regret as fuel for the future,

#82, Gary Vaynerchuk, Serial Entrepreneur and Chairman of VaynerX — The importance of kind candor, how to get over your insecurity, and why you need to embrace social media (Repost) Dec 17, 2024 1827 Gary Vaynerchuk, also known as "GaryVee," is a serial entrepreneur, the Chairman of VaynerX, and 5x New York Times Best Selling Author. He is a leading global mind on what's next in culture, relevance, and the internet. Gary possesses an uncanny ability to recognize trends and patterns early to help others understand how these shifts impact consumer behavior. He is one of the most f

#81: Colin Bryar, Co-Author of "Working Backwards;" former Chief of Staff to Jeff Bezos — How Amazon built its processes, the birth of the 6-page memo, and how to instill psychological safety in a competitive culture Dec 3, 2024 4944 Colin Bryar is a business advisor and technology leader whose career has focused on optimizing business strategy, technology, and operations. He is a former top-level executive at Amazon, where he spent more than 12 years – much of it in the early aughts during the company’s period of unmatched innovation – serving as a tech VP, leading the operations for IMDb.com, as well as shadowing and working

#80: David Heinemeier Hansson, Co-Owner of 37signals— Creating with first principles, acting with courage, and working in a world with no managers Nov 19, 2024 4828 David is the creator of Ruby on Rails, Co-Owner of 37signals, best-selling author, Le Mans class-winning racing driver, antitrust advocate, investor in Danish startups, frequent podcast guest, and family man.He writes regularly on HEY World and speaks on The REWORK Podcast. Hundreds of thousands of programmers around the world have built amazing applications using Ruby on Rails, an open-source web

#79, Shegun Otulana, Founder and CEO of Harmony Venture Labs—From Nigeria to unicorn founder; bootstrapping a profitable business; learning to embrace feedback Nov 5, 2024 4274 Shegun Otulana is a seasoned entrepreneur, advisor, mentor and investor. Drawing from his experience as a bootstrapped startup founder who found incredible success, his mission is to empower the next generation of builders by sharing his lessons learned to guide their entrepreneurial journeys. In addition to mentoring founders in his community – many of whom have gone on to launch successful compa

#78: Jake Schwartz, Co-Founder and former CEO of General Assembly—Navigating startup chaos, what a startup and the Beatles have in common, and the wisdom of looking back on the journey Oct 22, 2024 4393 Jake Schwartz is a serial entrepreneur, investor and advisor. Until 2020, Jake Schwartz served at CEO of General Assembly (GA), the global leader in education and career transformation, which he co-founded in 2011. He grew GA to over 1,000 employees on five continents. In 2018, GA was acquired by The Adecco Group. Jake Schwartz co-founded and serves as Chair of Brave Health, a mission-driven compa

#77: Jake Kloberdanz, One Hope Winery Co-founder — Building “Girl Scout Cookies” for adults, building community, and scaling philanthropy Oct 8, 2024 4920 Jake Kloberdanz is the founder of ONEHOPE, a pioneering wine brand with a mission to create a positive social impact. Under his leadership, ONEHOPE has donated tens of millions of dollars to over 40,000 non-profits and grown from zero to producing over one million bottles per year. The company boasts a world-class vineyard in Napa Valley and has garnered more than 30 wines with 90+ point ratings.

#76: Susan McPherson, Founder and CEO of McPherson Strategies — Investing in dormant ties, networking superpowers, and converting nerves into strength Sep 24, 2024 2479 Susan McPherson is a serial connector, angel investor, and corporate responsibility expert. As the founder and CEO of McPherson Strategies, a communications consultancy focused on brands and social impact, she brings over 30 years of experience in marketing, PR, and sustainability communications. Susan is the author of The Lost Art of Connecting and a sought-after speaker at major events like the

#75: Jeff Shiner, CEO of 1Password — Earning the right to lead, how to thrive while bootstrapping your company, and how to hire senior executives Sep 10, 2024 4188 Jeff Shiner is the CEO of 1Password, a leader in human centric security and privacy. Since joining in 2012, Jeff has grown the company from 20 people to a 900-employee global organization with a $6.8 billion valuation. Today, 1Password enables over 100,000 businesses and millions of individuals to navigate the digital world without fear or friction when logging in – and in less time. The company h

#74: Seth Godin, Author and Marketing Strategist — showing up for yourself, creating conditions for your best work, and how to deal with massive rejection (Repost) Aug 27, 2024 2937 Seth is an entrepreneur, best-selling author, and speaker. In addition to launching one of the most popular blogs in the world, he has written 20 best-selling books, including The Dip, Linchpin, Purple Cow, Tribes, and What To Do When It's Your Turn (And It's Always Your Turn). His book, This is Marketing, was an instant bestseller in countries around the world. Though renowned for his w

#73: David Savage, Group Technology Evangelist at Nash Squared and host of TechTalks podcast — How to become an "intrapreneur," the importance of consistent behavior over vanity metrics, and how to learn to trust yourself Aug 13, 2024 3680 David is Nash Squared's Group Technology Evangelist. He crafts podcasts, hosts video debates, speaks, moderates conferences, and chairs keynote stages. He's a passionate advocate for technology, dissecting its challenges and opportunities. David has worked at Nash Squared since 2007, where he has developed a deep understanding of the technology and talent markets. Recognised as Computing

#72: Kim Scott, Author of Radical Respect and Radical Candor — Building your team’s muscles to address discomfort, cutting through workplace politics, and why you need a purple flag Jul 30, 2024 4967 Kim Scott is the author of Radical Respect and Radical Candor. Kim was a CEO coach at Dropbox, Qualtrics, Twitter, and other tech companies. She was a member of the faculty at Apple University and before that led AdSense, YouTube, and DoubleClick teams at Google.Being able to hold a candid and caring conversation with someone is an essential part of leadership. My next guest on From Start-Up to G

#71: Matt Reustle, CEO of Colossus — Lessons from a first-time CEO, how to analyze a career pivot, and the art of a great question Jul 16, 2024 4598 Matt Reustle is currently the CEO of Colossus, a business that creates, curates, and distributes top-quality content for investors and entrepreneurs. He is the primary host of the Business Breakdowns podcast. Prior to Colossus, Matt worked in institutional investing. Most recently on the investment team at Raven Capital Management. Matt spent the first decade of his career at Goldman Sachs splitti

#70: Mike Michalowicz, Author and Entrepreneur — The right way to hire; practical exercises for team retention; and how to come back from rock bottom Jul 2, 2024 4264 Mike Michalowicz is the entrepreneur behind three multimillion-dollar companies and is the author of several business books, including Profit First, Clockwork, The Pumpkin Plan and his newest book, All In.Mike is a former small business columnist for The Wall Street Journal and business makeover expert for MSNBC. He regularly travels the globe as an entrepreneurial advocate.We are going all in on

#69, Rahul Vohra, Co-Founder and CEO of Superhuman — How to craft core values, tactics for implementing culture to help you achieve company goals, and the importance of moving quickly Jun 18, 2024 3101 Rahul Vohra is the Co-Founder and CEO of Superhuman. He is also a Technical Advisor at Boldstart Ventures, an investor and advisor at Partender, and an investor of sendwithus and Easy Post. He received his bachelor of arts in Computer Science at the University of Cambridge. Rahul shares the lessons he learned from being a serial entrepreneur, how and why he learned to meditate, what he does to bui

#68, Gina Bianchini, Co-Founder and CEO of Mighty Networks — The secret to building communities, managing self-worth as a CEO, and why humor is a leadership superpower Jun 4, 2024 3990 Gina Bianchini is the CEO & founder of Mighty Networks, a digital business platform that powers what it calls people magic. People magic is advanced technology and AI that connects the most relevant and interesting people to each other in the context of community, courses, events, and paid memberships.She’s also the author of the 2022 Wall Street Journal best selling book, Purpose: Design a Co

#67, Gary Vaynerchuk, Serial Entrepreneur and Chairman of VaynerX — The importance of kind candor, how to get over your insecurity, and why you need to embrace social media May 21, 2024 1776 Gary Vaynerchuk, also known as "GaryVee," is a serial entrepreneur, the Chairman of VaynerX, and 5x New York Times Best Selling Author. He is a leading global mind on what's next in culture, relevance, and the internet. Gary possesses an uncanny ability to recognize trends and patterns early to help others understand how these shifts impact consumer behavior. He is one of the most f

#66, Mary-Catherine Lader, COO of Uniswap Labs — How you know you're ready to take on more risk, why you should create anti-values, and the importance of community May 7, 2024 3914 Mary-Catherine Lader is the Chief Operating Officer of Uniswap Labs. She previously was a Managing Director at BlackRock, and Chief Operating Officer of the firm’s Digital Wealth business and head of its climate tech business, Aladdin Sustainability. She began her career as an investment analyst with Goldman Sachs’ Special Situations Group and served on the staff of the World Economic Forum’s Da

#65, Gregory Galant, Co-Founder and CEO of Muck Rack — Pros and cons of bootstrapping, building a scrappy culture, the importance of building a network Apr 23, 2024 4823 Gregory Galant is the co-founder and CEO of Muck Rack, a platform enabling PR teams to work together to find the right journalists for their stories, send customized pitches, build meaningful relationships with the media, monitor news and quantify their impact. It’s used by thousands of organizations, including Taco Bell, Pfizer, Golin, International Committee of the Red Cross, Knight Foundation,

#64, Kristi Herold, Founder and CEO of JAM — Pivoting during a crisis, leading through playfulness, and creating joy in the workplace Apr 9, 2024 3414 Kristi Herold is the CEO of JAM, a global business connecting people through play, and one of the largest recreational sports leagues in the world. Since 2020, JAM has produced 3,500+ corporate team-building events in over 30 countries. Kristi consults and speaks on how to move a culture from surviving to thriving. Her bestselling book, "It Pays to PLAY," is a rich resource to help organ

#63, Matt Abrahams, Author and Lecturer at Stanford University — Embracing vulnerability in leadership, the art of feedback, and how to personalize your pitch Mar 26, 2024 3946 If you've ever found yourself stumbling over words in a high-stakes presentation or wondering how to turn a dinner party into a deeper connection, this is the conversation you need to hear. Plus, for all the leaders out there, we have expert insights on managing emotional reactions to feedback and fostering a culture of open dialogue for transformative organizational growth.Prepare to enrich

#62, Sal Di Stefano, Co-Founder of Mind Pump Media — How authenticity drives growth, how you know you have the right cofounders, why being right is not the goal, and how physical strength drives your leadership Mar 12, 2024 5189 Get pumped for this episode of From Start-Up to Grown-Up!I sat down with Sal Di Stefano, the co-founder of Mind Pump Media. You’ll learn how he and his co-founders propelled a fitness podcast into a multifaceted business empire.I loved his perspective on embracing the journey, how authenticity drives growth, and the importance of NOT being right.This is a health-conscious conversation for your bo

#61, Rob Ryan, Co-Founder of Ascend Communications — Embracing a bootstrap mentality, picking the right spouse, and handling the mental and physical toll of entrepreneurship Feb 24, 2024 4295 My guest for the latest episode of From Start-Up to Grown-Up is Rob Ryan, Co-Founder of Ascend Communication. Ascend was acquired by Lucent Technologies in 1999 by Lucent Technologies.Rob is a fount of knowledge about entrepreneurship and courageous leadership. He’s also a great story teller and a hoot! Check out this clip for a sneak peek into our talk where Rob talks about something important fo

#60, David Meltzer, Co-Founder of Sports 1 Marketing, and Peter Goldstein, Entrepreneur and author of The Entrepreneur's IPO — The surprising way money impacts your life, the three forms of ignorant arrogance, and how to prepare to take your company publi Feb 13, 2024 1978 This new episode of From Start-Up to Grown-Up features a dynamic tag team of David Meltzer, the Co-Founder of Sports 1 Marketing, and Peter Goldstein, entrepreneur and the author of “The Entrepreneur’s IPO”!You’ll hear about David’s complete rebirth in his life and career journey as he shares the surprising ways that money impacts your life, and Peter shares solid gold advice about how you can pre

#59, Jim McKelvey, Co-Founder of Block (formerly Square)— Building a team of missionaries, what true innovation takes, and the importance of timing Jan 30, 2024 4131 How do you find your new idea?What does it take to attract a team of true believers?And what does glass-blowing have to do with entrepreneurship? Hint: the key is timing.All of these questions are answered in my newest episode of From Start-Up to Grown-Up with Jim McKelvey, the Co-Founder of Block (previously known as Square)!Jim McKelvey is best known for co-founding Square, now called Block. He

#58, Josh Reeves, CEO and Co-Founder of Gusto — Upholding the platinum rule, taking control of your attention, and a framework for hiring people who are in love with your problem Jan 2, 2024 4277 If you’re looking for inspiration to upgrade your leadership for 2024, you’ll want to listen to my conversation with Josh Reeves, CEO and Co-Founder of Gusto on the newest episode of From Start-Up to Grown-Up.These are just three topics from our talk that are fantastic guides to follow into the new year:➡️ The key to hire the right people for your company ➡️ The one rule that will help you manage

#57, Jon Beckstrand, CEO of MasterControl — Developing a leadership code, how to look forward to hard conversations, and ways to repurpose stress Dec 19, 2023 4527 Does your company have an employee bill of rights?Jon Beckstrand put one together for his team as CEO of MasterControl.That’s just one of the strategies that Jon has used at MasterControl to grow the company and successfully execute a pivot. We talked about his leadership philosophy, his tools for learning, and how he’s come to embrace having difficult conversations. Listen to the rest of it for h

#56, Bob Muglia, Former CEO of Snowflake — Having a values-based vs. performance-based company, rooting out dysfunction, and getting fired by Steve Balmer twice Dec 5, 2023 4115 What is the real impact of one bad apple on your team?What’s it like to work directly with Bill Gates? What’s your playbook for coming in as CEO of a promising company - like Snowflake - and taking them from 0 revenue to $100M in 5 years? On this episode of From Start-Up to Grown-Up, Bob Muglia, the former CEO of Snowflake and author of The Datapreneurs: The Promise of AI and the Creators Building

#55, Jerry Colonna, Author and Executive Coach — the distinction between vulnerability and honesty, the power of radical self-inquiry, and why you need to heal core wounds to be a great leader Nov 21, 2023 4035 Not all feedback is created equal. Giving positive feedback offers far more benefits than simply showing gratitude for someone’s work. It also helps as a vital step to personal self-discovery and self-inquiry. This is a central theme of Jerry Colonna’s brand new book, Reunion: Leadership and the Longing to Belong.Jerry joins me on the newest episode of From Start-Up to Grown-Up to discuss the proc

#54, Jim Kwik, Brain Coach and Author — How to find your dominant question, what we can learn from trauma, and the framework to move your vision forward Nov 7, 2023 3132 We often ask each other “What’s your why?”Go a step deeper and ask: “What’s your dominant question?”Jim Kwik is a brain coach and the author of the #1 WSJ bestseller, “Limitless: Upgrade Your Brain, Learn Anything Faster, and Unlock Your Exceptional Life.” One of the many fascinating things we discuss is the idea of the dominant question - why it’s so important and useful if you want to do big thi

#53, Gareb Shamus, Founder of ACE Comic Con— Going from passion to product, how to keep yourself in the game, and why inclusion fosters new businesses Oct 24, 2023 4716 Gareb Shamus is a visionary in the Superhero and character-based franchise worlds. Throughout the last 30 years, he’s made a tremendous impact on geek and nerd culture and formed relationships with an unrivaled collection of artists, writers, toy developers, game designers, and celebrities. Gareb founded Comic Con as we know it today, producing 180 events with millions of tickets sold, reaching bi

#52, Joe Landolina, Co-Founder and CEO of Cresilon— Starting a company in his dorm room, finding the right investors; and the importance of transparent communication Oct 10, 2023 4396 At 17 years old, inventor and entrepreneur Joe Landolina invented a medical breakthrough that is transforming at-home and in-patient wound care. Landolina conceived an adhesive hemostatic gel composed of plant-based polymers that could adhere to a wound site and simultaneously support the natural clotting process. To refine and manufacture the gel technology he invented, Landolina with his partner

#51, Joel Jackson, Co-Founder and President of Lifeforce — Working with celebrity founders, taking in feedback without getting defensive, and frameworks for learning from experience Sep 25, 2023 4451 Joel Jackson is co-founder and President of Lifeforce, the first clinically integrated health optimization platform. He is a Canadian entrepreneur and executive who has led technology organizations across healthcare, consumer goods, and wellness. Most recently, Joel was CTO of Upgrade Labs, a personal optimization and recovery company based in Santa Monica, California. Prior to Upgrade Labs, Joel

#50, Jerry Neumann and Elizabeth Zalman, Authors of Founder Vs. Investor — Learn to love fundraising, handle board dynamics, and how to speak VC Sep 11, 2023 4507 Liz is an infrastructure and information security expert. She is a two-time founder / CEO of venture-backed companies, building the first to a successful exit and the second to a multi-hundred-million-dollar business. Elizabeth has raised more than $100 million in venture capital from the most renowned investors in the world, and is a frequent speaker and guest at industry events and tech podcasts

#49, Joe Thomas, Co-Founder and CEO of Loom — Why it’s essential to track your time; how to get better at fundraising; getting your head right to make good decisions; and how to decide to keep building your company, even if it means sleeping on a mattress Aug 28, 2023 4388 Joe Thomas is the CEO and co-founder of Loom, the video communication platform for async work. Joe leads Loom in its mission to empower effective communication, wherever work happens. Prior to Loom, Joe served as Director of Product at MyLife.com and Director of Operations at MediaPass. He also co-founded Redesign Agency while in college at Indiana University.While leading Loom, Thomas has been re

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