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 joined Colossus (founded by Patrick O’Shaughnessy) as Chief Marketing Officer. She also runs a consultancy called The Kool-Aid Factory (a truly brilliant name, I think), helping startups shape their company culture. Brie is empathetic, thoughtful, and relatable—traits that shine throughout this conversation. Let's get to it!

In this episode:

Get full show notes and links at https://GoodWorkShow.com.

Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

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 experience, a friend encouraged him to run for city council during a pivotal moment of governmental restructuring in Portland. Though we don’t always agree on the solutions, I admire Nat’s passion for public service and his unique entrepreneurial perspective. In this conversation, we explore what motivates someone to shift from business to public service and what it’s like to be on the cusp of a new political journey. Let’s get to it. 

In this episode:

Get full show notes and links at https://GoodWorkShow.com.

Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

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 solutions. Over her career, she’s shifted from a policy-centric approach to tackling climate change to a venture capital perspective, where she now helps build the companies that will shape the future. We dive into Clea’s personal journey, the global challenges we face due to climate change, and how innovative companies are developing solutions. I’ve had the pleasure of working with Clea before, and I know you’ll enjoy our conversation. Let’s get to it!

In this episode:

Get full show notes and links at https://GoodWorkShow.com.

Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

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 podcast, The Shit You Don’t Learn in School. I admire Steph for her ability to expose people to new ideas and possibilities in their careers and lives. In this episode, we discuss her journey, her philosophy on impact, and how she approaches building her unique and impactful career. I think you’ll find her story and insights as inspiring as I did. Let’s get to it!

In this episode:

Get full show notes and links at https://GoodWorkShow.com.

Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

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 company, and Shippo has grown into a powerhouse, serving more than 50,000 businesses. We dive into how she’s led this growth, the values that drive her and her team, and how they turned a boring problem into something extraordinary. Join me as we explore Laura’s journey, her leadership, and what it really takes to build and scale a company like Shippo. Let’s get to it!

In this episode:

Get full show notes and links at https://GoodWorkShow.com.

Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

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 Square & Co / Barnes & Noble, and Emily exited the business. She is also the co-author and illustrator of There Is No Good Card for This: What to Say and Do When Life Gets Scary, Awful, and Unfair to People You Love (HarperOne, 2017), and offers unsolicited advice and cautionary tales in her newsletter, Subject to Change, a Substack Featured Publication of 2023.

This week, Barrett talks with Emily about their mutual experiences of burnout, identity loss, and recovery after leaving significant professional roles. Emily shares her journey from a high-stress advertising career to creating a company focused on empathy cards, driven by her experience surviving cancer. Emily and Barrett discuss the rapid growth and subsequent burnout she experienced, the emotional and mental toll of such high stress, and the importance of reconnecting with one's authentic self amidst professional pressure. They cover a wide range of topics, including personal stories of financial insecurity, the search for purpose, self-acceptance, and the balance of ambition with self-care, emphasizing the significance of internal work and the healing power of genuine human connections and new beginnings.

In this episode:

Get full show notes and links at https://GoodWorkShow.com.

Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

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 facing our world. Known for her keen insights and high standards, Tamara is deeply passionate about storytelling, business development, and championing people with big ideas.

This week, Barrett talks with Tamara about her exceptional career journey, from building a presence on Twitter to curating influential works at Stripe Press. Drawing from her upbringing as an African immigrant and the influence of her parents, Tamara reflects on the importance of surrounding oneself with high achievers, the value of curiosity, and the pursuit of excellence. She emphasizes the transformative power of storytelling, her love for tacit knowledge, and her vision for blending tech with story to influence the world. Barrett and Tamara also discuss the nuances of impactful work, the lasting influence of intentional connections, and Tamara's aspiration to inspire others while shaping a meaningful legacy through publishing.

In this episode:

Get full show notes and links at https://GoodWorkShow.com.

Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

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 family and serves as founding advisor for Screendoor Partners.

This week, Barrett and Kanyi share a wide-ranging conversation about life, business, parenting, and more. They explore Kanyi’s journey from apartheid South Africa to the U.S. venture capital scene, and how his consciously crafted identity influences his approach to work and life. They talk about the impact of COVID-19 on venture capital, the evolution of technology in society, and the role of scientific discovery in innovation. They also discuss the importance of maintaining diverse cultural spaces amidst algorithm-driven content, the balance between mysteries and secrets in business, and the importance of supporting independent creators. They share their reflections on purposeful parenting and its unconscious impact, highlighting themes of identity, creativity, and the intersection of individual and collective progress.

In this episode:

Get full show notes and links at https://GoodWorkShow.com.

Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

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' Climate Change Commission, the Wisconsin Conservative Energy Forum, and BridgeUSA. A frequent contributor to national media outlets, Benji is one of the leading youth environmental voices in the country.

This week, Barrett talks with Benji about his early start in political activism inspired by John McCain, the intense bullying he faced in high school, and his efforts to bridge bipartisan divides in environmental advocacy. Benji shares his experiences with burnout and the difficult decision to step down from his leadership role at the ACC while continuing his mission toward nonpartisan environmental solutions. They discuss the dangers of perceived expertise without real experience, the necessity of adapting policies over time, and the importance of building bipartisan coalitions.

In this episode:

Get full show notes and links at https://GoodWorkShow.com.

Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

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 talks with Austin about his journey as a photographer, storyteller, and entrepreneur. They discuss the pivotal moments that shaped Austin’s career, from his early days of hustling for a job at National Geographic to his collaboration with Apple on the groundbreaking "Shot on iPhone" campaign. Austin talks about his relationship with his wife and fellow artist, Esther Havens, and how their shared passion for socially impactful storytelling and empathy-driven photography has guided their work. Austin also discusses the importance of curiosity, determination, and meaningful intent in his work, as well as the power of photography to challenge, inspire, and enable others to explore the beauty of the world around them.

In this episode:

Get full show notes and links at https://GoodWorkShow.com.

Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.