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Episode | Date |
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#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
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Apr 21, 2025 |
#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
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Apr 08, 2025 |
#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
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Mar 25, 2025 |
#87: How Daniel Yanisse Scaled Checkr to $700M+ and Overcame the Post-Hypergrowth Crisis
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Mar 11, 2025 |
#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)
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Feb 25, 2025 |
#85: Isabelle Freidheim, Founder of Athena Capital — The benefits of being an only child, creating opportunities for women in finance, and unlocking hidden talent
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Feb 11, 2025 |
#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
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Jan 28, 2025 |
#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)
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Dec 31, 2024 |
#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)
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Dec 17, 2024 |
#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
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Dec 03, 2024 |
#80: David Heinemeier Hansson, Co-Owner of 37signals— Creating with first principles, acting with courage, and working in a world with no managers
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Nov 19, 2024 |
#79, Shegun Otulana, Founder and CEO of Harmony Venture Labs—From Nigeria to unicorn founder; bootstrapping a profitable business; learning to embrace feedback
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Nov 05, 2024 |
#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
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Oct 22, 2024 |
#77: Jake Kloberdanz, One Hope Winery Co-founder — Building “Girl Scout Cookies” for adults, building community, and scaling philanthropy
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Oct 08, 2024 |
#76: Susan McPherson, Founder and CEO of McPherson Strategies — Investing in dormant ties, networking superpowers, and converting nerves into strength
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Sep 24, 2024 |
#75: Jeff Shiner, CEO of 1Password — Earning the right to lead, how to thrive while bootstrapping your company, and how to hire senior executives
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Sep 10, 2024 |
#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)
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Aug 27, 2024 |
#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
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Aug 13, 2024 |
#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
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Jul 30, 2024 |
#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
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Jul 16, 2024 |
#70: Mike Michalowicz, Author and Entrepreneur — The right way to hire; practical exercises for team retention; and how to come back from rock bottom
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Jul 02, 2024 |
#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
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Jun 18, 2024 |
#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
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Jun 04, 2024 |
#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
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May 21, 2024 |
#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
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May 07, 2024 |
#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
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Apr 23, 2024 |
#64, Kristi Herold, Founder and CEO of JAM — Pivoting during a crisis, leading through playfulness, and creating joy in the workplace
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Apr 09, 2024 |
#63, Matt Abrahams, Author and Lecturer at Stanford University — Embracing vulnerability in leadership, the art of feedback, and how to personalize your pitch
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Mar 26, 2024 |
#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
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Mar 12, 2024 |
#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
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Feb 24, 2024 |
#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
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Feb 13, 2024 |
#59, Jim McKelvey, Co-Founder of Block (formerly Square)— Building a team of missionaries, what true innovation takes, and the importance of timing
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Jan 30, 2024 |
#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
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Jan 02, 2024 |
#57, Jon Beckstrand, CEO of MasterControl — Developing a leadership code, how to look forward to hard conversations, and ways to repurpose stress
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Dec 19, 2023 |
#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 05, 2023 |
#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
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Nov 21, 2023 |
#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 07, 2023 |
#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
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Oct 24, 2023 |
#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
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Oct 10, 2023 |
#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
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Sep 25, 2023 |
#50, Jerry Neumann and Elizabeth Zalman, Authors of Founder Vs. Investor — Learn to love fundraising, handle board dynamics, and how to speak VC
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Sep 11, 2023 |
#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
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Aug 28, 2023 |
#48, Vishal Sunak, Founder and CEO of LinkSquares — Decision-making frameworks, the most potent management technique, how to build a fierce network from scratch
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Aug 14, 2023 |
#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
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Jul 31, 2023 |
#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
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Jul 17, 2023 |
#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
|
Jul 03, 2023 |
#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
|
Jun 12, 2023 |
#43: Seth Godin, Author and Marketing Strategist — showing up for yourself, creating conditions for your best work, and how to deal with massive rejection
|
May 30, 2023 |
#42: Matt Biilmann, Co-Founder and CEO of Netlify — career pivoting, marketing for mass adoption, and growing company culture remotely
|
May 15, 2023 |
#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
|
May 01, 2023 |
#40: Peter Attia, MD, Founder of Early Medical — improving your lifespan and healthspan, the centenarian decathlon, and the process of making major life changes
|
Apr 17, 2023 |
#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
|
Apr 03, 2023 |
#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
|
Mar 20, 2023 |
#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
|
Mar 06, 2023 |
#36: Hubert Palan, Founder and CEO of Productboard — the challenges of scaling leadership, tactics for fundraising, and finding a work/life balance
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Feb 22, 2023 |
#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
|
Feb 04, 2023 |
#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
|
Jan 24, 2023 |
#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
|
Jan 05, 2023 |
#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
|
Dec 14, 2022 |
#31: Mid-Day Squares - Creating fans and not customers, building a company as a family, and the power of social media
|
Dec 05, 2022 |
#30: Rob Kramer of PurposeLab — Building resilience, an unconventional career path, and working with the Kardashians
|
Nov 28, 2022 |
#29: Dan Zavorotny, Nutrisense
|
Nov 08, 2022 |
#28: Melissa Daimler, Udemy
|
Oct 19, 2022 |
#27: - Andy Karsner, X (a division of Alphabet)
|
Sep 29, 2022 |
#26: Maëlle Gavet, Techstars
|
Sep 14, 2022 |
#25: Larry Gadea, Envoy
|
Aug 29, 2022 |
#24: Carolyn Childers, Chief
|
Jul 25, 2022 |
#23: Scott Belsky, Behance
|
Jul 11, 2022 |
#22: Sarah Dorsett, Nanit
|
Jul 05, 2022 |
#21: Alexi Robichaux, BetterUp
|
Jun 14, 2022 |
#20: Oleg Rogynskyy, People.ai
|
May 23, 2022 |
#19: Jon Stein, Betterment
|
May 09, 2022 |
#18: Paul English, Boston Venture Studio
|
Apr 25, 2022 |
#17: Kara Goldin, Hint Inc.
|
Apr 12, 2022 |
#16: Julien Smith, Practice
|
Mar 28, 2022 |
#15: Ilan Twig, TripActions
|
Mar 17, 2022 |
#14: Sid Viswanathan, Truepill
|
Feb 16, 2022 |
#13: Ragy Thomas, Sprinklr
|
Jan 25, 2022 |
#12: Rahul Vohra, Superhuman
|
Jan 10, 2022 |
#11: Robin Matlock, VMware
|
Jan 03, 2022 |
#10: Greg Galant, Muck Rack
|
Dec 20, 2021 |
#9: David Sax, Author
|
Dec 08, 2021 |
#8: Rick Nucci, Guru
|
Nov 30, 2021 |
#7: Jennifer Dulski, Rising Team
|
Nov 22, 2021 |
#6: Jeff Wald, WorkMarket
|
Nov 15, 2021 |
#5: Sadie Lincoln, Barre3
|
Nov 08, 2021 |
#4: Chris Hsu, Azibo
|
Nov 01, 2021 |
#3: Jake Stein, Common Paper
|
Oct 19, 2021 |
#2: Zvi Band, Contactually
|
Oct 15, 2021 |
#1: Matt Blumberg, Bolster
|
Oct 11, 2021 |
#0: A Welcome Message from Alisa
|
Jul 15, 2021 |