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?

  1. 11 MAI

    Danielle Malik: UX Leader's unexpected and gratifying path into housing solutions.

    After 20 years in tech consulting and leadership, Danielle was laid off. She knew it was time for a change. But what? Tech didn't seem like a path forward anymore. She made the unexpected but extremely gratifying shift into housing, becoming a housing provider for people challenged by the Bay Area rental market. Her company, Rising Tide Residences offers room rentals for men, women and families from diverse backgrounds, looking for stability and a chance to level up. These are people who have just come out of prison, have aged out of foster care, or have another  difficult situation that makes it hard to find housing. She's found success in making buildings into stable homes.  Hear her story and what she plans to do next.  To connect, learn more about their offerings, or to apply for housing, visit www.risingtideresidences.org Link: www.risingtideresidences.org Send us Fan Mail EVOLUTION OR REVOLUTION is produced by Courtney Kaplan. Website: Iconic Leadership Coaching. Follow me on IG @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    47 min

  2. 4 MAI

    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 @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    49 min

  3. 22 AVR.

    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 @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    49 min

  4. 11 MARS ·  BONUS

    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 @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    14 min

  5. 4 MARS ·  BONUS

    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 @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    18 min

  6. 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 @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    25 min

  7. 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 @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    1 h 1 min

  8. 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 @iconic_owl Connect on Linked in @courtney-kaplan  Music by Midwest Got It (IG: midwestgotit)

    55 min
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À propos

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?

Informations

  • Création
    Courtney Kaplan
  • Années d’activité
    2025 - 2026
  • Épisodes
    13
  • Classification
    Tous publics
  • Copyright
    © 2026 Evolution or Revolution
  • Site web de l’émission
    Evolution or Revolution