Good Work with Barrett Brooks

Good Work with Barrett Brooks

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Good Work with Barrett Brooks episodes

  • The Hardest Decision of My Career: Inside Kieran Snyder’s CEO Journey

    This week, I talk with Kieran Snyder, the co-founder and former CEO of Textio, a groundbreaking company at the forefront of the AI revolution. Kieran’s journey is one of resilience, leadership, and innovation. We discuss how she transitioned from academia to leading a tech startup, raising more than $40 million in funding, and building equitable, high-performing teams along the way. Kieran opens up about the tough decision to step down as CEO after experiencing burnout and shares her path to recovery and rediscovery. We dive into her passion for building up young female leaders, from coaching girls’ basketball to supporting women in tech, and her talent for transforming surprising data into compelling stories through her newsletter, Nerd Processor. Whether you’re a leader, entrepreneur, or just curious about AI’s impact on the workplace, I hope this conversation will inspire and offer some practical insights as well. Let’s get to it!

    In this episode:

    • (00:00) - Intro
    • (02:55) - Kieran's 8th grade science project
    • (05:07) - How parental influence shaped Kieran's career path
    • (08:29) - Academic journey in linguistics
    • (17:19) - Kieran's transition to tech
    • (23:47) - Founding Textio
    • (30:11) - Building a company with your spouse
    • (36:18) - Navigating product market fit
    • (46:46) - Burnout and stepping down as CEO
    • (56:35) - Leadership and knowing when to walk away 
    • (01:01:23) - Detaching identity from career outcomes
    • (01:05:33) - How Kieran evaluates her performance as a CEO
    • (01:08:39) - The value of a board of advisors
    • (01:11:45) - Kieran's advice for someone recruiting a mentor, advisor or board member
    • (01:15:25) - Starting Nerd Processor and embracing creativity
    • (01:19:14) - How Kieran chooses what to write about
    • (01:23:20) - How to create substantial and insightful content
    • (01:30:11) - What Kieran has learned about hiring execs
    • (01:35:13) - Coaching youth basketball and personal fulfillment
    • (01:41:03) - Kieran's beautiful future
    • (01:42:59) - Who Kieran is becoming

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

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

      1 hr 48 min
    • Inside Pat Flynn’s World: Family, Fishing, Pokémon, and Smart Passive Income

      This week, I talk with Pat Flynn, a legend in the creator economy and founder of Smart Passive Income. Pat’s journey began in 2008 when he was laid off as an architect during the recession. Since then, he’s built an online empire by experimenting with niche projects and side hustles, teaching modern, effective principles to entrepreneurs worldwide. We dive deep into his journey—from building Smart Passive Income to leading with empathy and authenticity. Pat shares how he turned his love of Pokémon cards into a million-subscriber YouTube channel, Deep Pocket Monster, and how hobbies and family keep him grounded and inspired. This conversation is personal, insightful, and packed with actionable lessons for entrepreneurs, creators, and anyone wanting to build a meaningful career while staying true to your values. Let’s get to it!

      In this episode:

      • (00:00) - Intro
      • (02:58) - Kayak bass fishing tournaments?
      • (10:50) - The importance of getting outside regularly
      • (14:38) - The hardest part of Pat's lifestyle change
      • (21:38) - Parenting and dealing with negativity online
      • (38:08) - How Pat built his career around family
      • (41:26) - Being present with family
      • (43:54) - Involving family in business
      • (46:18) - How Pat created open communication with his children
      • (49:24) - Standing out and embracing uniqueness
      • (55:33) - Pat on losing his first architecture job
      • (59:13) - The journey to online business
      • (01:02:56) - Launching the first online product
      • (01:08:29) - Learning from mistakes and moving forward
      • (01:10:00) - Embracing just-in-time learning
      • (01:12:39) - Overcoming the inner conflict of perfectionism
      • (01:16:18) - The importance of mentorship
      • (01:17:23) - Hiring a Fortnite coach
      • (01:18:13) - Triathlon Training with Jeff McMahon
      • (01:18:58) - The art of asking for help
      • (01:21:47) - Embracing consistency and iteration
      • (01:22:29) - Mastering storytelling and content creation
      • (01:30:33) - Building relationships with an audience
      • (01:37:49) - Finding success by making content community-driven
      • (01:41:08) - Teaching by example vs telling people what they should do
      • (01:45:23) - Pat's beautiful future
      • (01:46:46) - Who Pat is becoming

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

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

        1 hr 52 min
      • How Ankur Nagpal Turned Adversity into a $250M Empire

        This week, I talk with Ankur Nagpal, founder of Teachable, Carry, and Vibe Capital. Ankur’s journey is nothing short of inspiring. From immigrating to the U.S. for college to founding a company that grew exponentially and sold for a life-changing $250 million, Ankur has built a remarkable career. We explore how he went from creating Facebook apps in college to funding his own education at Berkeley, starting and scaling Teachable in New York, and what he learned about himself after the sale. Ankur shares how success has allowed him to focus on what truly matters—family, meaningful relationships, and purpose-driven work. Now with Carry, he’s on a mission to bring elite investment and tax strategies to everyday business owners. This is a story of resilience, authenticity, and leadership. Let’s get to it!

        In this episode:

        • (00:00) - Intro
        • (02:51) - What makes cricket a beautiful sport?
        • (06:40) - Growing up in Oman and moving to the US
        • (16:32) - Navigating the US visa system
        • (22:09) - What Ankur learned from his initial success building Facebook apps
        • (32:01) - Making a million dollars and forgetting to pay taxes
        • (33:51) - Finding home in New York
        • (38:07) - How New York has shaped Ankur professionally and personally
        • (43:10) - Teachable and the evolution of the creator economy
        • (49:08) - Challenges of scaling a startup
        • (57:45) - What will change for content creators over the next 10 years?
        • (01:04:35) - Deciding to sell Teachable
        • (01:09:22) - Life-changing realizations
        • (01:12:31) - Ankur's first big purchase after selling the company
        • (01:14:13) - Walking away from CEO
        • (01:16:42) - Investing and family priorities
        • (01:19:36) - What Ankur learned as an investor that he didn't know as a founder
        • (01:24:01) - Traveling self-discovery
        • (01:27:19) - Building a new company
        • (01:38:29) - Ankur's beautiful future
        • (01:40:19) - Who Ankur is becoming

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

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

          1 hr 43 min
        • What I’ve Learned About Excellence, Purpose, and Showing Up: AMA with Barrett Brooks

          Since the very first episode, Good Work has been about exploring why our work matters and how it helps us become the people and leaders we’re meant to be. Normally, I interview world-class guests, diving deep into their unique stories and insights. But today, I’m sharing my own experiences, lessons, and reflections. I’ve gathered questions from you, my listeners, as well as past guests, covering a wide range of topics: business advice, lessons learned from podcasting, life philosophy, and how I approach my own work. This episode is a chance to connect on a different level as I reflect on the year and answer your questions. I hope it brings value and inspiration as we wrap up the year together. Let’s get to it!


          In this episode:

          • (00:00) - Intro
          • (02:44) - What's the number one process business owners need to have to stay happy and engaged? 
          • (05:14) - What are the biggest tactical challenges that $1m+ creator/founders struggle with?
          • (14:05) - What are the common threads in the life ambitions or mentality of the people you've had on the podcast?
          • (27:25) - How have you changed, matured, or grown as a result of something you've learned from a guest on Good Work?
          • (31:22) - What have you learned about podcasting that you didn't know or didn't expect when you started?
          • (39:14) - Has podcasting changed anything about your views on the impact and importance of various forms of media in society at large?
          • (44:16) - Of all the people you talked to, for whom did your respect increase the most after all the research and conversation, and why?
          • (47:44) - What's up with the podcast artwork? And is there any meaning behind the studio design?
          • (56:50) - What is your definition of "enough"?
          • (01:04:04) - What are some challenges you're proud of solving, and how did you solve them? 
          • (01:13:21) - Over the last 10 years, what's become more important to you, and what's become less important? Does his weekly calendar match the answer?
          • (01:16:14) - What are you avoiding just because it will take longer than you'd like?
          • (01:17:09) - What was most surprising about 2024, and how are you feeling about 2025?
          • (01:19:07) - is there anything you've learned in your life that you wish you didn't know?
          • (01:22:23) - What six-month period of your life was the most energizing and fun, and what can you learn from the answer?
          • (01:32:26) - How do you manage your day and your week?
          • (01:38:27) - What would young Barrett think of the work you're doing today?
          • (01:44:43) - If you were the teacher for your kids and a few other local kids, what's one class or curriculum you'd love to teach them and why?
          • (01:48:08) - Why are garbage trucks stinky? And what makes buses awesome?
          • (01:49:56) - Final thoughts

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

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

            1 hr 53 min
          • The Power of Owning Your Story with Ruthie Ackerman

            This week, I talk with Ruthie Ackerman—a talented author, journalist, and writing teacher who has turned her own journey into a blueprint for helping others find their voice. Ruthie’s work has appeared in The New York Times, Modern Love, and many other renowned outlets, but her true passion lies in empowering others to discover and write their own stories. Through her workshops, one-on-one coaching, and book incubators, Ruthie helps writers connect with their experiences, heal from the past, and find deeper meaning in their lives. We explore Ruthie’s journey—from traveling the world in her 20s, to pivoting into journalism, to teaching creative nonfiction and memoir to students around the globe. We also dive into the deeply personal moments that shaped her path, including her journey to motherhood. Ruthie’s insights on storytelling, healing, and personal growth are inspiring, and I hope our conversation encourages you to reflect on your own story and its potential to create meaning and connection. Let’s get to it!

            In this episode:

            • (00:00) - Intro
            • (02:48) - How Ruthie ended up in Malawi
            • (10:31) - The path to journalism
            • (13:19) - Brooklyn dreams
            • (18:38) - Reporting from Liberia and Lebanon
            • (28:18) - The Forbes experience
            • (32:05) - Starting Write Your Life
            • (36:12) - How Ruthie teaches writing
            • (47:51) - The importance of memoir
            • (53:25) - Balancing personal and professional life
            • (01:03:55) - The journey to motherhood
            • (01:09:28) - Dealing with changing desires 
            • (01:16:14) - Understanding self-silencing and emotional repression
            • (01:24:02) - The reality of fertility treatments
            • (01:28:24) - Dating after divorce
            • (01:33:17) - Finding love and facing heartbreak
            • (01:44:19) - Meeting Rob
            • (01:48:37) - Reflections on the journey and personal growth
            • (01:52:06) - Ruthie's most beautiful future
            • (01:55:09) - Who Ruthie is becoming

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

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

              1 hr 59 min
            • Andy Crissinger: The Art of Asking Better Questions

              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 curriculum built around five transformative books, offering practical insights for personal and professional development. These resources can help you grow into the leader, partner, and parent you aspire to be. I loved this conversation with Andy about finding purpose, building trust, and achieving meaningful growth, and I think you will too. Let’s get to it!

              In this episode:

              • (00:00) - Intro
              • (00:05) - Who is Leonard?
              • (03:25) - What music represents for Andy
              • (07:28) - Family, integrity, and sense-making
              • (14:15) - Andy's transition to ministry
              • (17:09) - What Andy learned about community through ministry
              • (23:13) - Coaching vs teaching
              • (30:20) - The journey through infertility
              • (39:16) - How impact and joy of fatherhood
              • (43:15) - Transitioning to coaching
              • (48:00) - Founding Worksong
              • (01:00:23) - Humble Inquiry by Edgar Schein
              • (01:13:11) - Inherited Family Trauma
              • (01:19:42) - Andy's beautiful future
              • (01:22:18) - Who And is becoming
              • (01:24:19) - Trees by Howard Nemerov

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

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

                1 hr 31 min
              • How 3.7 Million Words Built a Career: Lessons from Patrick McKenzie

                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 work-life balance, his evolving thoughts on autonomy, and how writing has opened doors to unexpected opportunities. Known for his deep dives into topics you didn’t realize you cared about, Patrick brings fresh perspectives on tech, culture, and finding meaning in work. Let’s get to it!

                In this episode:

                • (00:00) - Intro
                • (03:10) - Why gaming is underrated for learning real-world skills
                • (06:21) - Why do thieves steal soap?
                • (08:54) - Following intellectual curiosity
                • (13:18) - Call centers and organizational systems
                • (22:39) - Lessons from 20 years in Japan
                • (28:30) - The salaryman
                • (37:08) - Patrick's transition to entrepreneurial ventures
                • (39:09) - How to know what to keep and what to change
                • (42:14) - Dealing with career uncertainty
                • (52:08) - Professionals vs amateurs
                • (57:14) - Lessons from Stockfighter
                • (01:01:07) - Stripe and stepping into the void
                • (01:21:50) - The impact of writing and sharing knowledge
                • (01:26:30) - The relationship between community and impact

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

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

                  1 hr 33 min
                • Why Tim Grahl Had To Kill His Old Business to Find Real Success

                  This week, I talk with Tim Grahl, CEO of Story Grid and author of The Shithead, 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 reality. We cover a range of topics, from Tim’s journey as a book marketer to his insights on the power of structure in storytelling. We also dive into his personal experiences, including the impact of therapy on his growth as both a person and a professional. Tim’s work ethic and passion for meaningful storytelling are infectious, and I think you’ll find our conversation both inspiring and thought-provoking. Let’s get to it!

                  In this episode:

                  • (00:00) - Intro
                  • (05:06) - Tim's perfect vacation
                  • (11:54) - Doing work that people don't understand
                  • (15:19) - The "secret" to Tim's success
                  • (20:34) - The moment Tim knew his business was broken
                  • (31:06) - What is an object of desire?
                  • (34:10) - The problem with online courses (and how to fix it)
                  • (01:03:47) - Behind the scenes of writing a meaningful book
                  • (01:13:37) - Success and the half warm beer theory
                  • (01:18:03) - Reflecting on regret
                  • (01:24:28) - How therapy changed everything
                  • (01:32:58) - Chasing insight vs integration
                  • (01:38:19) - Tim's beautiful future
                  • (01:42:47) - Who Tim is becoming

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

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

                    1 hr 47 min
                  • Why Real Relationships Are the Secret to Growing Your Business with Mo Bunnell

                    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 development framework, applying it to my business in ways that make it practical and actionable. Mo’s insights reveal how success, when rooted in genuine connection, transforms careers and lives. I hope you enjoy this conversation with one of the kindest, most relationship-driven people I know. Let’s get to it!

                    In this episode:

                    • (00:00) - Intro
                    • (03:32) - How Mo ended up tied to a donkey in the Colorado mountains
                    • (09:22) - Reflecting on 32 years of marriage
                    • (12:41) - The power of writing down goals
                    • (16:13) - Case study: Pursuing a dream home
                    • (24:45) - Parenting and the importance of family rituals
                    • (34:59) - Celebrating achievements and friendships
                    • (37:21) - The role of community and friendship
                    • (39:26) - Building a sense of belonging
                    • (40:00) - The Breckenridge and Mashup experience
                    • (41:01) - Creating and hosting events
                    • (49:28) - Writing, publishing, and becoming an author
                    • (01:03:35) - Applying the Give to Grow framework
                    • (01:11:52) - The five lies we tell ourselves
                    • (01:14:31) - Overcoming the lies and setting goals
                    • (01:19:35) - Designing a buy-in process
                    • (01:22:14) - Identifying and engaging with clients
                    • (01:24:49) - The power of specialization
                    • (01:30:37) - Creating scalable systems
                    • (01:38:37) - Mo's beautiful future
                    • (01:40:23) - Who Mo is becoming

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

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

                      1 hr 43 min
                    • The Hidden Gem of a Naturopath Who Wrote the Manual to Health and Longevity - Dr. Erika Siegel

                      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 wellness as an entrepreneur. We explore how to sustain your health, just like a professional athlete, to keep performing at your best. If you’re looking for practical tips on managing stress, taking care of your body, and making an impact without sacrificing your well-being, this episode is for you. Let’s get to it!

                      In this episode:

                      • (00:00) - Intro
                      • (04:45) - Erika's 40-mile hike 
                      • (08:46) - Why mental preparation is key
                      • (11:02) - The Importance of Honest Communication
                      • (15:56) - Erika's Journey into Medicine
                      • (22:02) - Choosing a Path in Naturopathic Medicine
                      • (27:05) - The Evolution of Functional Medicine
                      • (33:40) - Life in Portland and Embracing Nature
                      • (44:02) - Nature's Healing Power
                      • (52:03) - Parenting with Intention 
                      • (01:03:47) - Healthy expressions of emotion
                      • (01:15:19) - Holistic Health Strategies
                      • (01:24:35) - How psychology impacts biology 
                      • (01:29:41) - Starting points for managing stress
                      • (01:35:52) - How to kick bad habits
                      • (01:40:55) - Detoxifying in a Modern World 
                      • (01:55:58) - Erika's beautiful future
                      • (01:56:52) - Who Erika is becoming

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

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

                        2 hr

                      About Good Work with Barrett Brooks

                      From the publisher's feed

                      Good Work is a curated exploration of the inner journey of outward success. Through deeply researched, long-form conversations with founders, authors, artists, and adventurers, host Barrett Brooks…

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