Evolution or Revolution

Courtney Kaplan
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A podcast about people making small (or very large) professional changes. I explore how they did it and how you can, too. If it's time to make a change, when do we trim the sails, and when do we burn the boats?

Episodios

  1. HACE 1 DÍA

    Erin Wade: Mac and Cheese Millionaire. From lawyer to restaurant innovator and author

    "I think the journey that most of us are on with work really has to do with a process of self discovery that has followed us our whole lives.” When Erin Wade was fired from her job as a lawyer, she decided it was time to take on a big project - creating a restaurant space that prioritized purpose, culture, and  hospitality. Erin is the founder of Homeroom, a restaurant with a cult following in Oakland, California, focused on delivering the absolute best mac and cheese.  She bootstrapped her restaurant, starting by investing her own money (no investors) and worked tirelessly in every corner—from building furniture to training staff. She was committed to launch a restaurant that was counter to typical dining culture. She designed systems rooted in transparency, employee engagement, and values that resonate beyond just serving mac and cheese. Our conversation unpacks some of the lessons learned as well as her advice to others hoping to build something meaningful. Erin Wade: https://www.erinwade.co/ Erin's Book: The Mac and Cheese Millionaire Homeroom: https://www.homeroom510.com/ 2018 WaPo Editorial Link  Chapters 00:00 - From Lawyer to Mac and Cheese Entrepreneur 03:38 - Childhood Influences and Entrepreneurial Spirit 06:13 - The Journey to Homeroom: A New Vision for Restaurants 09:12 - Building a Unique Restaurant Culture 12:24 - The Financial Risks and DIY Approach 15:15 - The First Weeks of Homeroom: Success and Challenges 18:04 - Hiring and Team Building: Lessons Learned 21:04 - Creating a Transparent and Engaging Workplace 23:52 - Values-Based Decision Making in Business 27:02 - Support Systems for Entrepreneurs Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconicleadershipcoaching Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    49 min

  2. 22 ABR

    Tina Santiago-Keenan: Leaving tech, creating immersive experiences for people IRL

    In this conversation, Courtney Kaplan interviews Tina Santiago-Keenan, co-founder of Secret City, a creative design and production studio that creates immersive experiences. Tina shares her journey from working in tech at Facebook and Uber Eats to launching Secret City, which combines elements of escape rooms and immersive theater. The discussion covers the challenges of entrepreneurship, the impact of the pandemic, and the importance of community and in-person experiences. Tina also offers insights on career transitions, balancing work and family, and the future of Secret City. Links: Website: https://secretcity.studio/ Social Links: https://www.instagram.com/secretcityadventures/ Learn More: https://www.secretcityadventures.com/ Chapters 00:00 Introduction to Tina Santiago-Keenan and Secret City 05:35 Tina's Career Journey and Transition to Secret City 10:53 Challenges in the Early Days of Secret City 21:48 Navigating Challenges During COVID-19 27:08 The Importance of In-Person Connections 32:04 Advice for Career Transitions 36:29 Balancing Parenthood and Entrepreneurship 40:21 Introduction to Tina's Journey 42:53 The Importance of Patience and Testing Ideas 44:18 Leveraging Existing Skills and Collaboration Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconicleadershipcoaching Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    49 min

  3. 11 MAR ·  CONTENIDO EXTRA

    Bonus: Four dead end traps when we want to change

    Over the years, I’ve seen how we can lead ourselves into dead ends when it comes to change. There are some ways we think about change that are actually pretty unproductive and not really useful.. and are also common patterns. So, in this episode, I want to share a few of the ways we get blocked. Anything sound familiar? Getting to know how you sabotage or position yourself in dead ends is helpful to figure out how you're going to get out. I’ve also seen - and experienced firsthand - how change is navigated more successfully. How we can frame changes in our lives to be less terrifying or stressful and more fun, creative and adventurous. (Really!) But that's in the next mini-episode. I know I was squirming in my chair in recognition while recording this one. Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconicleadershipcoaching Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    14 min

  4. 4 MAR ·  CONTENIDO EXTRA

    Bonus: Change is here, but I don't wanna. Six phrases to move on.

    Today’s episode is different - it’s called: Change is here. But I don’t wanna. I wanted to share thoughts about dealing with professional change when you’d rather freak out. On the pod, I interview people who are choosing new paths. But many folks that didn’t make a decision, but have faced a layoff, downsizing, health crisis or other change that perhaps they didn’t plan for or expect. Today, I share 6 things to help you reconnect, and start moving forward when parts of you really want to fall apart. Books about change: Transitions, William Bridges - This is a classic. Whenever I refer this book online, I get comments that folks love it.The Search, Bruce Feiler - inspiring case studies of people making changes.The Good Enough Job, Simone Stolzoff - he has another one called How Not To Know which sounds like another helpful book that I look forward to reading.Mindset. The new Psychology of Success, Carol S. Dweck - counters our false ideas about how we tend to think people are “naturally” good at things.Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconicleadershipcoaching Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    18 min

  5. 15/10/2025

    Anna Bloom: Launching her product with love

    Have you thought about launching your own product? I know I have.   My guest today, Anna Bloom, has worked as a design leader at AirBnB, Facebook, and Cash App. In 2021, she took a leap to launch her own thing while still working full-time. Anna shares what it takes to get a physical product on the shelves and what keeps her going during difficult times.  PS Quick note, this isn’t a sponsored podcast. (But I am a huge fan of Anna and Lococo)  PPSS She offered listeners a one-time 10% off discount when you shop lococomagic.com  Code: ICONIC10 Website: LOCOCO Magic IG: @lococo_magic Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconicleadershipcoaching Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    25 min

  6. 23/09/2025

    Jason Kriese: VP at Salesforce goes back to school

    Jason Kriese shares a his massive evolution from corporate life as an executive to going back to school in order to better align his time and efforts with his values of service.  Jason was an operations leader and user experience advocate who can effectively manage the integration of complex design efforts into engineering organizations.  As VP of Design Operations at Salesforce, he founded and led the DesignOps team in support of 500+ designers in the Product UX organization, collectively shipping solutions across the enterprise CRM ecosystem. Working at Microsoft and Amazon, he shipped products and features across a variety of platforms, including: web, embedded, PC, browser, mobile handset, and tablets. After a series of personal life experiences, he started to wonder what was beyond working in tech. He asked questions that opened big choices, big changes and big actions that required him to apply his own motto: "Think big, be brave and jump". Looking ahead, Jason is pursuing a new focus on social work and communities in need. He's currently in the second year of his MSW program at DU. Jason and I were in similar roles at different companies at the same time. Earlier this year, when I saw a post he made about going back to school. I knew I had to know more. You're going to love this conversation, and his generous transparency about every step of the way.  Jason's LinkedIn post that started it all. Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconicleadershipcoaching Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    1 h 1 min

  7. 23/09/2025

    Serene Lewis: Retired at 50. Ready to help you do it, too.

    As a retirement coach, Serene Lewis helps people identify and set reachable goals in the areas of money, mindset and community.  Often we think about retiring "someday" but having a plan makes it real and can make it happen sooner. Especially in uncertain times, you may be facing retirement or a big change sooner than you expected. Serene says, "I’ve observed that about 80% of people say they’re going to retire in 2 years. Deeper conversation reveals that only 20% are PLANNING to retire."  So what's the difference? Find out in our episode as Serene Lewis shares how she left traditional work in her mid-50s and now lives in Portugal.  Learn more about Serene Lewis:  Read her LinkedIn Post about retirement Connect with Serene Lewis via LinkedIn   Her website is: www.serenelewis.coach Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconicleadershipcoaching Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    55 min

  8. 02/06/2025

    Brandy Cerne: Embracing the winding path to a beach town in Brazil

    Brandy Cerne spent her twenties in New York. As Brandy says:  "I get asked a lot, 'Do you have experience in this field?' The short answer is no, I don't have direct hotel experience. The long answer is that all of my career has led me here." She working in brand she experienced a masterclass in hospitality at Shake Shack from Danny Meyer and Randy Garutti.  She took a career break volunteering in hostels in Eastern Europe, where this seed of her dream began. Her hands-on event organizing and magic making at Sofar Sounds required major expectation setting for guests stepping into an unfamiliar environment. Then back into the startup world with Groove, on online working space tackling connection-building for those working solo from home.  But how do these things combine to land her on a beach in Brazil running a guesthouse? Her pousada is called O Portalzinho, which is "a hotel for people who like people." And her story getting there is one that will inspire you. Book: Feel the Fear and Do It Anyway Podcast: How I Built This with Guy Raz Book time at O Portalzinho Follow on O Portalzinho on IG Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconicleadershipcoaching Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    35 min

  9. 06/05/2025

    Jennifer Kanyamibwa-Biggs: Re-invention and bold moves

    Jennifer Kanyamibwa-Biggs has worked with the best of them at Twitter, Slack, Strava, but also in government roles with Mayor Michael Bloomberg as well as non-profits. She is also a co-founder of Plant Lady Juice a VC backed wellness company based in Atlanta. We talk about how Jennifer adapts and evolves her skills into new industries and ventures. She shares how she makes big decisions and the things she believes are most important to being able to change. I hope you enjoy this one! You can find Jennifer here: LinkedIn: https://www.linkedin.com/in/kanyamibwa/ IG @ Plantladyjuiceco Or her website: https://plantladyjuice.co/ Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconicleadershipcoaching Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    57 min

  10. 06/05/2025

    Kat Vellos: Making connections to help your journey

    Kat Vellos has written books, taught workshops, and given talks about about how people can break out of feeling lonely by creating opportunities to connect with others.  In this episode, Kat talks about how we can use the same techniques in our professional lives. When we are considering professional transitions, we often need to reach out for support. Maybe there's someone in a role you're interested in or a connection that could help answer a question you have. Reaching out might feel awkward if we're out of practice. Kat shares an easy framework that makes it easier for people to respond to our requests. Our conversation also explores how Kat recommends formulating experiments to bring more of what matters into your life if the timing isn't right for bigger changes. We can explore and learn in multiple ways before making big decisions. You can find Kat at: https://www.katvellos.com/ https://weshouldgettogether.com/ Or buy her book her: We Should Get Together And her link to the post about 13-year olds requesting information.  Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconicleadershipcoaching Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    39 min

  11. 15/04/2025

    Mark Brenwall: Stories on sobriety, moving across the world and starting again at 40

    At 40 years old, Mark Brenwall had it all. He lived in a loft in San Francisco's Mission District. Working in tech, he had money, he had friends and big nights on the town.  But it took him 20 years to realize it just wasn't for him.  Sobriety helped give him to space to see that he wasn't happy -- but also wasn't sure what was next. Mark  shares each step of those transitional years from exploratory trips to setting up a company on his own, and finally setting down new roots in Thailand.  Looking back, he says, "It couldn't have worked out better."  Tune in and hear Mark's story of transformation and reinvention at 40.  Hear about how: Taking small steps before making a big move can reduce risk and increase confidence.Building a community is crucial for adapting to a new environment.Sobriety can provide clarity and mental space for life-changing decisions.Keywords: life transformation, expatriation, remote work, entrepreneurship, personal growth, Thailand, digital nomad, career change, sobriety, international living Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconicleadershipcoaching Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    36 min

  12. 15/04/2025

    Erin Ryan: From homebirth midwife to global maternal health advocate

    Join me in my first ever episode to talk with Erin Ryan. She'll share her revolutionary journey from San Francisco, to becoming a homebirth midwife in Vermont, moving her three children to Bali (twice) and re-inventing her life again when her marriage ended. Today you'll find her in Tonga, Fiji, Sri Lanka, Lao, and Bangladesh connecting with community,  and advocating for and training with midwives globally.  Erin looks back on her journey and the key moments when everything changed.  Our discussion emphasizes meaningful change, the power of small experiments, and the trade-offs and risks of big moves. Erin shares personal challenges, such as a difficult divorce and relying on community support, which illustrate resilience and the interweaving of her personal and professional lives.  If you're thinking of making a big switch professionally, join us and get inspired by Erin's story. Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconicleadershipcoaching Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    30 min
  • 12 episodios

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A podcast about people making small (or very large) professional changes. I explore how they did it and how you can, too. If it's time to make a change, when do we trim the sails, and when do we burn the boats?

Información

  • Creador
    Courtney Kaplan
  • Años de actividad
    2025 - 2026
  • Episodios
    12
  • Clasificación
    Apto
  • Copyright
    © 2026 Evolution or Revolution
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