Good Work with Barrett Brooks

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: (00:00) - Intro (03:52) - Writing to one person: techniques and inspirations (06:57) - The role of writing in personal identity (09:59) - Navigating the AI landscape (12:21) - Turning down the noise: digital detox (17:03) - Paul Graham’s ‘Founder Mode’ essay (26:48) - The importance of taste and curation (35:06) - Brie’s creative explosion in 2022 (37:12) - The writing process & self-editing (40:19) - Is the nature of writing online changing? (44:34) - Career docs and personal achievements (54:26) - Brie’s essay on depression (56:51) - Navigating depression and loneliness (01:01:19) - The power of self-soothing (01:07:59) - The importance of setting boundaries (01:09:13) - On trusting others (01:12:03) - The impact of athletics (01:18:51) - Identity loss after sports (01:22:17) - On leaving Stripe (01:24:33) - Optimizing for good vibes (01:26:55) - Communicating your value (01:30:46) - What’s next for Brie? (01:34:51) - Brie’s beautiful future (01:39:38) - Who Brie is becoming 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: (00:00) - Intro (06:02) - The art and science of cider-making (11:51) - Growing the business vs enjoying the craft (14:20) - On the importance of marketing (20:34) - Challenges and changes during the pandemic (32:25) - The moment Nat realized it was time to move on (36:40) - Nat’s approach to building culture in his team (49:17) - Moving on from a business (54:47) - Seeing the city as a bus driver (01:08:02) - Running for city council (01:15:21) - Defining the role of a city councilor (01:19:02) - Nat’s collaborative approach to politics (01:22:49) - Challenges and opportunities for small businesses (01:25:36) - A vision for Portland’s future (01:39:56) - Nat’s beautiful future (01:43:14) - Who Nat is becoming 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: (00:00) - Intro (04:21) - Biking from London to Paris (09:17) - Physical challenges and personal growth (16:37) - Cultural identity and its Impact (25:05) - Clea's mission-driven career in climate tech (32:13) - From policy to capital (38:25) - Lowercarbon and Clea's approach to solving climate change (44:24) - The impact of the IRA bill (47:47) - Hydrogen and its challenges (51:53) - Evaluating investment opportunities (54:48) - The excitement of deep tech (58:33) - Leadership and building a strong team (01:03:54) - The future of fusion energy (01:11:31) - Unique carbon capture solutions (01:20:00) - Clea's beautiful future (01:22:01) - Who Clea is becoming 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: (00:00) - Intro (03:53) - Building community through shared experiences (07:16) - Documentary screenings (11:28) - How exposure to new things shapes your experiences (15:27) - Balancing specialization and exploration (18:50) - The nomadic lifestyle and remote work (22:55) - Personal growth through travel and learning (29:46) - How Steph’s nomadic lifestyle has changed (33:48) - How marriage impacts life and work (42:23) - Settling down and building roots (45:41) - Pandemic reflections (49:20) - Multicultural upbringing and identity (56:06) - What led to Steph’s creative explosion in 2019 (01:03:30) - How to break through the noise (01:14:52) - How Steph has approached podcasting as a full-time job (01:27:57) - What makes a great podcast host (01:37:25) - Untranslatable words: Capturing unique experiences (01:48:54) - Steph’s beautiful future (01:51:50) - Who Steph is becoming​ 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: (00:00) - Intro (03:40) - How Laura became the “stick figure girl” (07:45) - How optimism serves Laura and her team (11:14) - Handling customer feedback and roadmaps (21:14) - The complexities of shipping logistics (33:49) - Laura’s vision for Shippo and empowering SMBs (39:21) - Improving customer experience (44:13) - Adding personality to a brand (46:52) - Building a strong co-founder relationship (57:42) - Company culture and values (01:06:19) - Leading with authenticity (01:12:09) - Lessons learned from managing remote teams (01:18:03) - How Laura’s global upbringing has shaped her (01:21:57) - The role of community and personal growth (01:25:55) - Reflections on immigration and personal identity (01:29:52) - Laura’s beautiful future (01:32:07) - Who Laura is becoming​ 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: (00:00) - Intro (05:19) - Emily’s advertising background and first viral card (11:30) - Navigating business growth and challenges (18:42) - Merging with Knock Knock and burnout (27:04) - Barrett’s story of burnout (32:06) - The aftermath of leaving a successful role (39:14) - Embracing quitting and self-discovery (55:53) - Facing setbacks and choosing a new path (01:01:55) - Redefining success and ambition (01:13:53) - A shift in self-perception (01:16:21) - Embracing vulnerability (01:18:25) - Letting go of burdens (01:22:14) - Rediscovering self-worth (01:24:58) - Navigating new ambitions (01:40:55) - Emily’s beautiful future (01:41:48) - Who Emily is becoming (01:45:41) - Barrett’s poem 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: (00:00) - Intro (03:39) - Tamara’s journey to Stripe Press (06:47) - Turpentine and provocations (09:24) - Challenges and innovations in publishing (13:03) - The role of Stripe Press in Stripe’s ecosystem (19:02) - The first book that captured Tamara’s imagination (26:21) - Tamara’s early days at Stripe (35:22) - Interviewing Jordan Mechner (37:48) - The duality of Teddy Roosevelt (40:13) - Remembering Charlie Munger (48:58) - The influence of mentors and unconventional career paths (01:04:55) - The value of high-quality authors and books (01:13:26) - The desire for excellence (01:16:08) - Family expectations and developing taste (01:23:54) - Principles for early career success (01:38:14) - Tamara’s beautiful future (01:44:11) - Who Tamara is becoming 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: (00:00) - Welcome to Good Work (02:47) - Hip hop culture and the Kendrick-Drake beef (09:01) - The importance of identity and teaching (13:14) - How family history shaped Kanyi’s identity (18:24) - The role of identity in personal and professional life (30:59) - Advice for founders (38:48) - How COVID reshaped the venture capital landscape (47:03) - On being “American-African” (01:00:52) - The intersection of neuroscience and technology (01:08:27) - The value of pseudoscience in innovation (01:19:16) - Mysteries vs. secrets in business (01:28:37) - Parenting and personal growth (01:34:17) - Kanyi’s beautiful future (01:37:20) - Who Kanyi is becoming 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: (00:00) - Intro (04:17) - Burnout and stepping down as CEO (12:35) - Reflecting on leadership and personal growth (29:22) - The importance of bipartisan climate solutions (33:17) - Benji's brand of conservatism (40:24) - Bullying and opposition in school (56:55) - Bridging the political divide and finding solace in nature (01:04:38) - Building coalitions in politics (01:16:48) - Political sensationalism (01:21:35) - Understanding different perspectives (01:30:07) - Republicans and environmentalism (01:33:40) - Start local (01:40:28) - How to create change (01:46:51) - Making the environment nonpartisan (01:47:57) - Who Benji is becoming 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: (00:00) Intro (05:11) - Austin's move to National Geographic (15:29) - Early influences (19:29) - The role of technology in photography (23:50) - The future of photography in the age of AI (32:47) - Austin’s college years and faith journey (36:00) - A life-changing moment (38:45) - Finding purpose through faith and photography (43:04) - Austin reflects on his lightning photo  (49:20) - Early career and social impact work (56:27) - First iPhone review and growing recognition (01:07:34) - The Shot on iPhone campaign (01:11:58) - The surreal experience of seeing your work on billboards (01:14:39) - How Austin met his wife (01:21:05) - Austin's unique proposal (01:30:51) - Austin's mission and the life plan exercise (01:36:43) - Who Austin is becoming Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.