This week, I talk with Andy Crissinger, a world-class coach and master facilitator who has guided leaders at some of the world’s most renowned startups and companies. Andy’s journey to coaching is remarkable, weaving through ministry, startup leadership, and eventually finding his calling as a coach. In the first half of our conversation, we explore his personal story, which is deeply relatable and filled with lessons about growth and resilience. In the second half, we dive into a coaching...

This week, I talk with Patrick McKenzie, better known online as “patio11.” Patrick has built an impressive career by sharing his insights publicly, with more than three million words published to date. From his years at Stripe to his current sabbatical, Patrick’s journey proves that the “traditional path” is not always the best one. We explore how his love for systems thinking and complex problem-solving has shaped his career. He shares candidly about his 20 years in Japan, navigating...

This week, I talk with Tim Grahl, CEO of Story Grid and author of The S******d, a novel that’s both thrilling and deeply personal. Tim made a name for himself as a book marketer who landed multiple titles on the New York Times  Bestseller list at the same time. Tim’s work with Story Grid, alongside his partner Shawn Coyne, has guided hundreds of aspiring authors in mastering the essential elements of storytelling, helping them transform “I hope I can write a book someday” into a published...

This week, I talk with my friend Mo Bunnell, founder of GrowBIG and the Bunnell Idea Group, which offers one of the most in-depth, relationship-driven trainings on sales and business development. Mo is the author of Give to Grow, a book I recommend to anyone interested in learning business development with a values-centered approach. We start by diving into Mo’s personal life, his deep commitment to family, and the strength of his marriage. In the second half, Mo shares his unique business...

This week, I talk with Dr. Erika Siegel, a naturopathic doctor with nearly 20 years of experience. I discovered her work through a recommendation from my doctor and was immediately drawn to her two-volume book set, The Nourish Me Kitchen, which combines essential health wisdom with practical recipes. As a coach, I see many entrepreneurs burning out due to the immense physical and mental demands of their work. In our conversation, Erika shares her journey and insights on how to maintain...

This week, I talk with my friend Kevin Lavelle, founder of Mizzen+Main, a company that revolutionized the dress shirt industry. We talk about how Kevin built Mizzen+Main into a successful brand, and why he ultimately decided to step back and bring in a CEO. We dive into Kevin’s early career in management consulting and the journey to his prior role at Stand Together, a nonprofit backed by Charles Koch, including how he navigated the challenges and opportunities that came with that. We also...

This week, I talk with Brie Wolfson, someone whose reputation precedes her. She’s the kind of person people rave about getting to work with. Brie was instrumental in bringing Stripe Press to life, partnering with John Collison and the Stripe team to build something truly special. After her time at Stripe, she moved to Figma before eventually facing burnout and needing a break. Brie has been open about her journey through depression, which we dive into during our conversation. Brie recently...

This week, I sit down with Nat West, founder and former CEO of Reverend Nat’s Hard Cider, a pioneering craft cider company in Portland, Oregon. Over 12 years, Nat helped shape the city’s thriving cider scene before making the bold decision to close his business, despite its post-pandemic stability. Seeking a change, Nat spent six months driving a public city bus—a dream he’d always had—and rediscovered his love for Portland, a city (my city) often misunderstood in national media. Inspired by...

This week, I talk with Clea Kolster, Head of Science and Partner at Lowercarbon Capital, a venture capital fund dedicated to solving climate change, or, as they put it, un-f***ing the planet. Lowercarbon is one of my favorite funds because they’re not just focused on making an impact—they’re also unafraid to make serious money along the way. Clea has a fascinating background, growing up between Persian and Danish cultures, and ultimately finding her passion in science, technology, and climate...

This week, I talk with Steph Smith, someone I consider a true curator of the internet. Steph is a writer, podcaster, and currently the host of the A16Z Podcast for the venture capital firm Andreessen Horowitz. She’s built an incredible online presence with her viral articles on remote work, productivity, and more, which have stood the test of time. Steph’s work has led her to opportunities like running the Trends Newsletter for The Hustle and creating projects like Internet Pipes and her...

This week, I talk with Laura Behrens Wu, co-founder and CEO of Shippo, a company that’s transforming the way e-commerce businesses handle shipping logistics. If you’re not in the e-commerce world, you may not have heard of Shippo, but for those who are, it’s a big deal. They help businesses seamlessly get products from A to B with some of the simplest, most elegant shipping solutions out there. Laura’s story is especially remarkable—she’s one of the few female CEOs of a billion-dollar...

Emily McDowell is an advisor, thought partner, and coach to creative entrepreneurs in the product space, helping to save their time, money, and sanity. As founder of the stationery and gift company Em & Friends, she inspired a sea change in the greeting card industry with Empathy Cards, a more honest and supportive alternative to traditional sympathy cards, and for nearly a decade, some element of her work was in a constant state of “viral.” In 2022, Em & Friends was acquired by Union...

Tamara Winter is the Commissioning Editor at Stripe Press, the publishing imprint of Stripe, and a board member of the Institute for Progress and the Foundation for American Innovation. Previously, she worked as the head of strategy at the Charter Cities Institute, and at the Mercatus Center. She has written for the Chicago Tribune, Works in Progress, and a16z. She also wrote and hosted Beneath the Surface, a limited-run podcast about infrastructure and some of the most complex challenges...

Kanyi Maqubela is Managing Partner at Kindred Ventures, where he focuses his investment and formation work in theme areas including frontier technology, digital health, e-commerce, financial technology, and supply-chain/logistics. As an entrepreneur and operator, Kanyi is a co-founder at Heartbeat Health, the largest virtual heart health platform in the United States. He has also served as an Adjunct Professor at New York University Tisch School of the Arts. He lives in San Francisco with his...

Benji Backer is the Executive Chairman and Founder of the American Conservation Coalition (ACC), the largest right-of-center environmental organization in the country, and the author of The Conservative Environmentalist: Common Sense Solutions for a Sustainable Future. A proud graduate of the University of Washington, Benji has been awarded the Fortune 40 Under 40, Forbes 30 Under 30, GreenBiz 30 Under 30, and Grist 50. He serves as a board member of the American Academy of Arts and Sciences'...

Austin Mann is a talented photographer, adventurer, and technology influencer known for his captivating images and storytelling. With a passion for exploring the beauty of creation, Austin has traveled the world, capturing stunning photographs and sharing his experiences through his work. He has gained recognition for his expertise in using Apple products, particularly the iPhone, as powerful tools for photography and has been featured in Apple's "Shot on iPhone" campaign. This week, Barrett...

Joshua Scott is the creator and president of JHS Pedals. His YouTube series, The JHS Show, has garnered millions of views from audiences spanning the globe. Josh is passionate about the history and stories surrounding guitar technology and teaches in collaboration with museums, companies, and universities. Often considered the historical authority on guitar's sonic evolution from the sixties to the present day, Josh contributes his knowledge to historical archive preservations, auction...

Josh Kaufman is the bestselling author of books on business, applied psychology, and practical wisdom. His first book, The Personal MBA, is a top-selling business book worldwide, with more than 1 million copies sold. His second book, The First 20 Hours, introduced a universal research-based method of learning fun and useful skills. His third book, How to Fight a Hydra, a "fairy tale for the entrepreneur's journey," debuted at #1 in Modern Philosophy on Amazon. This week, Barrett and Josh...

Michelle Tam is the co-creator of the Saveur Award-winning food blog, Nom Nom Paleo. Together with her husband, Henry Fong, they’ve also produced a two-time Webby Award-winning cooking app, authored three New York Times bestselling cookbooks, have been nominated for a James Beard Award, and created a best-selling line of paleo spice blends. This week, Barrett talks with Michelle about her journey from pharmacist to pioneer in the Paleo community, and her transition to food and wellness. She...

Andrew Farah is co-founder and CEO of Density Inc., where he has spent the last 10 years building real-time radar technologies for measuring how people use buildings. The company works with many in the Fortune 500, manufactures its anonymous radar systems in the United States, and has raised $227m in venture capital. Andrew lives near Golden Gate Park in San Francisco with his spouse, three daughters, and English Shepherd. This week, Barrett talks with Andrew about startup culture, building...

Nathan Barry is the Founder and CEO of ConvertKit. In previous careers, Nathan has been a designer, author, and blogger. After learning the power of email marketing, he gave up a successful blogging career to go all-in on ConvertKit. Outside of work, Nathan spends his time playing soccer, woodworking, and chasing after his three boys. This week, Barrett and Nathan sit down for a candid conversation about the ups and downs of building a $40M company, and what they wish they had done...

Fil Aronshtein’s journey is one of boundless curiosity, from his childhood dreams of becoming an inventor, architect, and astronaut, to his present-day mission of shaping the future of manufacturing. As the founder of Dirac, a company revolutionizing the manufacturing industry, he faced persistent rejection before finding his breakthrough. This week, Barrett talks with Fil about his vision for transforming manufacturing processes, and how that fits into a wider vision for a more expansive...

Polina Marinova Pompliano is the author of “Hiden Genius” and the founder of The Profile, a media organization that studies successful people and companies. Previously, she spent five years at FORTUNE where she covered technology and venture capital. As the author and editor of Term Sheet, FORTUNE’s industry-leading dealmaking newsletter, Polina interviewed the industry’s most influential dealmakers, including Melinda Gates, Steve Schwarzman, Richard Branson, and more. This week, Barrett...

Matt Mullenweg is co-founder of the open-source publishing platform WordPress, which now powers over 40% of all sites on the web. He is the founder and CEO of Automattic, the company behind WordPress.com, WooCommerce, Tumblr, WPVIP, Day One, Texts, and Pocket Casts. Additionally, Matt runs Audrey Capital, an investment and research company. He has been recognized for his leadership by Forbes, Bloomberg Businessweek, Inc. Magazine, TechCrunch, Fortune, Fast Company, Wired, University...