All Episodes

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

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

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

#114 - Kim Scott, Radical Respect and Radical Candor: How to Build Teams That Challenge Directly and Care Personally [ENCORE]

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

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

#111 – Dr. Becky Kennedy on Why Great Leaders Stop Managing Feelings and Start Building Trust

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

#109 Robbie Bent cofounder of Othership— From Rock Bottom to Community Buildering Community

#108 Semyon Dukach— MIT Blackjack Team Former Leader, Current VC, Invests Only in Immigrants

#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)

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

#105 Randy Komisar— Legendary Kleiner Perkins Investor Shares the 3 “Whys” Every Founder Must Answer (Encore)

#104 Issac Evans— How a Series D CEO Found Product-Market Fit, Stays Self-Aware, and Survived His Bank Melting Dow

#103 Patrick Lee— Rotten Tomatoes Founder: The Secrets to Building an Enduring Business

#102 Robert Glazer — Serial Entrepreneur on the Most Important Tool for Success

#101 Nick Huber — Building Wealth in “Boring” Businesses

#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

#99 Naveen Verma — From Princeton Professor to Venture-Backed CEO, Fundraising Without a Network, and Leading Firmly and Empathetically

#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

#97 Brad Feld, Founder of Techstars - Lessons from Techstars, why you should have “random” meetings, and the value of the “Give First” mentality.

#96: David Heinemeier Hansson, Co-Owner of 37signals— Creating with first principles, acting with courage, and working in a world with no managers (Repost)

#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.

#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.

#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.

#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

#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

#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

#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

#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

#87: How Daniel Yanisse Scaled Checkr to $700M+ and Overcame the Post-Hypergrowth Crisis

#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)

#85: Isabelle Freidheim, Founder of Athena Capital — The benefits of being an only child, creating opportunities for women in finance, and unlocking hidden talent

#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

#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)

#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)

#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

#80: David Heinemeier Hansson, Co-Owner of 37signals— Creating with first principles, acting with courage, and working in a world with no managers

#79, Shegun Otulana, Founder and CEO of Harmony Venture Labs—From Nigeria to unicorn founder; bootstrapping a profitable business; learning to embrace feedback

#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

#77: Jake Kloberdanz, One Hope Winery Co-founder — Building “Girl Scout Cookies” for adults, building community, and scaling philanthropy

#76: Susan McPherson, Founder and CEO of McPherson Strategies — Investing in dormant ties, networking superpowers, and converting nerves into strength

#75: Jeff Shiner, CEO of 1Password — Earning the right to lead, how to thrive while bootstrapping your company, and how to hire senior executives

#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)

#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

#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

#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

#70: Mike Michalowicz, Author and Entrepreneur — The right way to hire; practical exercises for team retention; and how to come back from rock bottom

#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

#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

#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

#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

#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

#64, Kristi Herold, Founder and CEO of JAM — Pivoting during a crisis, leading through playfulness, and creating joy in the workplace

#63, Matt Abrahams, Author and Lecturer at Stanford University — Embracing vulnerability in leadership, the art of feedback, and how to personalize your pitch

#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

#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

#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

#59, Jim McKelvey, Co-Founder of Block (formerly Square)— Building a team of missionaries, what true innovation takes, and the importance of timing

#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

#57, Jon Beckstrand, CEO of MasterControl — Developing a leadership code, how to look forward to hard conversations, and ways to repurpose stress

#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

#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

#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

#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

#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

#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

#50, Jerry Neumann and Elizabeth Zalman, Authors of Founder Vs. Investor — Learn to love fundraising, handle board dynamics, and how to speak VC

#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

#48, Vishal Sunak, Founder and CEO of LinkSquares — Decision-making frameworks, the most potent management technique, how to build a fierce network from scratch

#47, Randy Komisar, Entrepreneur and Investor — Lessons learned from a professional gambler, the role of luck your career, and the key decisions that drive the quality of your life

#46: Anouck Gotlib, Cofounder and CEO of Belgian Boys — Building a company when you’re a creative, dealing with your cofounder when he’s also your spouse, and the power of a walk out song

#45: Carolyn Rodz, Cofounder and CEO of Hello Alice — How to transform setbacks into learning, the best question to ask future employees, and how to build a strong cofounder relationship

#44: Lauren Bush Lauren, Founder and CEO of FEED — Building a business while making an impact, when not to take advice, learning to be direct, and how public service shaped her leadership

#43: Seth Godin, Author and Marketing Strategist — showing up for yourself, creating conditions for your best work, and how to deal with massive rejection

#42: Matt Biilmann, Co-Founder and CEO of Netlify — career pivoting, marketing for mass adoption, and growing company culture remotely

#41: Alex Zaccaria, Co-Founder and CEO of Linktree — finding a need in the market, when to take venture money, preparing for board meetings, and the value of conferences

#40: Peter Attia, MD, Founder of Early Medical — improving your lifespan and healthspan, the centenarian decathlon, and the process of making major life changes

#39: Alex Lieberman, Cofounder and Executive Chairman of Morning Brew — Mental health for founders, having a framework for decision-making, and deciding when it's time to leave your job to start a company

#38: Matthew Scullion, Cofounder and CEO of Matillion — Creating the right company culture, how to know your pivot is working, micro confidence vs. macro confidence, and the biggest obstacle in building a company

#37: Robert Glazer, Founder and CEO of Acceleration Partners — the importance of values and purpose, how to build your team's capacity, and why you should start your ideas even if they aren't ready

#36: Hubert Palan, Founder and CEO of Productboard — the challenges of scaling leadership, tactics for fundraising, and finding a work/life balance

#35: Padma Warrior, Founder and CEO of Fable — The reverse journey of grown-up to start-up, what to unlearn to become a founder, how to get your initial hires onboard, and rituals that build culture

#34: Nick Sonnenberg, Founder and CEO of Leverage — Bootstrapping your business; risk and how to build confidence; how to make your business more efficient, and how to come up for air

#33: 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

#32: Julia Boorstin, Senior Media and Tech Correspondent CNBC — The confidence dial, empathy as a strategic skill, and why playing sports makes for better leaders

#31: Mid-Day Squares - Creating fans and not customers, building a company as a family, and the power of social media

#30: Rob Kramer of PurposeLab — Building resilience, an unconventional career path, and working with the Kardashians

#29: Dan Zavorotny, Nutrisense

#28: Melissa Daimler, Udemy

#27: - Andy Karsner, X (a division of Alphabet)

#26: Maëlle Gavet, Techstars

#25: Larry Gadea, Envoy

#24: Carolyn Childers, Chief

#23: Scott Belsky, Behance

#22: Sarah Dorsett, Nanit

#21: Alexi Robichaux, BetterUp

#20: Oleg Rogynskyy, People.ai

#19: Jon Stein, Betterment

#18: Paul English, Boston Venture Studio

#17: Kara Goldin, Hint Inc.

#16: Julien Smith, Practice

#15: Ilan Twig, TripActions

#14: Sid Viswanathan, Truepill

#13: Ragy Thomas, Sprinklr

#12: Rahul Vohra, Superhuman

#11: Robin Matlock, VMware

#10: Greg Galant, Muck Rack

#9: David Sax, Author

#8: Rick Nucci, Guru

#7: Jennifer Dulski, Rising Team

#6: Jeff Wald, WorkMarket

#5: Sadie Lincoln, Barre3

#4: Chris Hsu, Azibo

#3: Jake Stein, Common Paper

#2: Zvi Band, Contactually

#1: Matt Blumberg, Bolster

#0: A Welcome Message from Alisa