Derek Sivers once believed success meant scaling bigger and moving faster. Then he built CD Baby, sold it, and gave the proceeds away – not because he had to, but because he realised enough was already enough.

As a writer, entrepreneur and modern business philosopher, Derek has spent years stripping life and business down to their essentials. What remains when you remove ego, growth for growth’s sake, and societal expectation? Clarity. Freedom. The space to choose.

In this conversation, Derek joins Kevin St. Clergy to explore why redefining success starts with questioning the stories we've been told. They uncover the cost of distraction, the power of radical focus, and how letting go (not adding more) can lead to bigger breakthroughs.

In this episode, Kevin and Derek will discuss:

(03:17) Accidental entrepreneurial journey

(07:27) Odometer metaphor and purpose

(11:31) Turning blame into empowerment

(13:36) Control what you can

(17:24) Making musicians happy as success

(20:38) Card table vs glamorous booths

(26:03) Prioritise focus over distraction

(27:15) Start with why for happiness

(31:20) Stop over-quoting and say it simply

(34:26) What truly makes you happy

(38:36) Think long-term for longevity

(40:01) Broaden identity and embrace growth

Derek Sivers is an entrepreneur, writer, and former musician best known for founding CD Baby and donating its multimillion-dollar proceeds to charity. A modern business thinker, he challenges conventional wisdom and advocates for simplicity, intentional living, and purpose-driven work through his bestselling books and global talks.

Connect with Derek:

Derek’s Website: https://sive.rs/ 

Resources Mentioned:

Can Negotiate Anything by Herb Cohen: https://www.amazon.com/dp/0553281097 

Grit by Angela Duckworth:  https://www.amazon.com/dp/1501111116/ 

How To Change by Angela Duckworth: https://www.amazon.com/dp/B08LQZDDDS/ 

New Happy by Stephanie Harrison: https://www.amazon.com/dp/139872212X

Stumbling on Happiness by Daniel Gilbert: https://www.amazon.com/dp/1400077427/

Daily Stoic by Ryan Holiday: https://www.amazon.com/dp/0735211736/

Outlive by Peter Attia: https://www.amazon.com/dp/0593236599 

Anything You Want by Derek Sivers: https://www.amazon.com/dp/1991153317/ 

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We don’t get stuck because we lack skill; we get stuck because we silence ourselves. Elaine Lin Hering once believed staying quiet kept the peace. But silence has a cost: it shapes who gets heard and who gets overlooked.

While studying power and influence at Harvard Law School and Triad Consulting Group, Elaine realised silence isn’t passive, it’s learned and reinforced. Understanding that gives us the choice to speak with intention.

In this conversation, Elaine joins Kevin to explore how silence derails tough conversations and why reframing “imposter syndrome” as “imposter treatment” changes how we show up.

In this episode, Kevin and Elain will discuss:

(04:27) Leadership, teams and impact

(08:17) It’s okay not to be okay

(10:36) Breaking the silence to communicate clearly

(14:34) How to break out of blame loops

(17:36) Unlearning silence in organisations

(22:41) What do I think and need?

(24:05) Rethinking imposter syndrome

(27:06) Why miscommunication really happens

(33:29) Feedback that fuels growth

(36:26) Communicating across differences

(39:31) Assessments that set you up for success

(41:55) How to structure healthy conversations

(45:33) Best books for self-directed learning

(47:27) How silence affects relationships

Elaine Lin Hering is a facilitator, speaker, and author who helps people communicate clearly, navigate conflict, and speak up with confidence. She has worked across six continents with organisations such as Google, Nike, American Express, Pixar, and the Red Cross. Previously, she served as Managing Partner at Triad Consulting Group and taught negotiation.

Connect with Elain:

Elain’s Website: https://elainelinhering.com/

Elain’s LinkedIn: https://www.linkedin.com/in/elainelinhering/ 

Resources Mentioned:

Unlearning Silence by Elaine Lin Hering: https://www.amazon.com/Unlearning-Silence-Speak-Unleash-Talent/dp/0593653602

Verbal Judo by George Thompson:  https://www.amazon.co.uk/Verbal-Judo-Second-Gentle-Persuasion/dp/0062107704 

HBR – Stop Telling Women They Have Imposter Syndrome: https://hbr.org/2021/02/stop-telling-women-they-have-imposter-syndrome 

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Most creatives don’t struggle because they lack talent – they struggle because they’re held back by limiting beliefs. Chris Do used to rely on creativity alone, assuming the right clients would just find him. Everything changed when he learned how to engage clients, uncover their real problems, and articulate value. The result? Opportunities that tripled his income.

In this conversation, Chris joins Kevin to break down the mindset shifts that drive a successful creative business – how to market without feeling salesy, price with confidence, and build genuine trust with clients.

In this episode, Kevin and Chris will discuss:

(03:59) Teaching over selling on YouTube

(08:26) Building success through skills and mindset

(11:06) Lesson on understanding clients

(13:53) Breaking free from limiting beliefs

(18:37) Value depends on perspective

(20:59) Ethical sales and problem solving

(23:08) Defining the right fit

(27:17) Make an effing decision

(29:54) Respectful decision making and building alliances

(32:16) Building trust through authenticity

(37:53) The value of honesty

(39:56) Masterclass in therapy and parenting

(42:09) Language and connecting minds through time

Chris Do is an Emmy Award-winning designer, educator, and entrepreneur with over two decades of experience in brand strategy and creative business. As the founder and CEO of The Futur, he has built a global education platform that empowers creatives to monetize their skills and build sustainable businesses. Chris has worked with top brands like Microsoft, Sony, Nike, and Starbucks, and generated over $1 million in digital product sales. Through his work, he’s helped thousands of professionals thrive in today’s creative economy.

Connect with Chris:

Chris’s Website: thefutur.com

Chris’s LinkedIn: linkedin.com/in/thechrisdo 

Chris’s Instagram: instagram.com/thechrisdo 

Resources Mentioned:

Selling with Noble Purpose: How to Drive Revenue and Do Work That Makes You Proud

by Lisa Earle McLeod: https://www.amazon.com/dp/1118408098 

Action Selling: How to Sell Like a Professional, Even If You Think You Are One by Duane Sparks: https://www.amazon.com/dp/0975356909 

The Mountain Is You: Transforming Self-Sabotage Into Self-Mastery by Brianna Wiest: https://www.amazon.com/dp/1949759229 

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Ever wondered why you're overlooked for leadership roles despite all your hard work? While working with corporate organizations in the 1980s, Sally Helgesen noticed a troubling pattern: talented individuals, particularly women, were often dismissed, and their ideas ignored. Determined to change this, she has spent the past 30 years breaking down barriers to career growth and creating spaces where talent can thrive, regardless of gender. In this episode, Sally joins Kevin to discuss the common habits that hold people back in their careers and how to overcome these barriers to get positioned for leadership opportunities and recognition.

Sally Helgesen is an international speaker, coach, bestselling author, and leading expert on women's leadership. With over 35 years of experience, she has worked with global organizations in 37 countries to foster inclusive work cultures.

In this episode, Kevin and Sally will discuss:

(00:00) Introduction 

(02:55) Her Path to Leadership: Breaking Barriers in the 80s

(05:14) Why Women Struggle to Own Their Achievements

(08:33) How to Claim Your Wins Without Bragging

(12:47) Why Expertise Alone Won't Get You Ahead

(15:13) Building vs. Leveraging Relationships

(20:08) The Disease to Please: The Power of Saying “No”

(25:47) The Cost of Chasing Perfection

(32:35) Leadership Challenges in Today's Workplace

(37:18) How Sally Invests in Her Growth

Sally Helgesen is an international speaker, coach, bestselling author, and leading expert on women's leadership. With over 35 years of experience, she has worked with global organizations in 37 countries to foster inclusive work cultures. Cited by Forbes as the world’s premier expert on women’s leadership, Sally has been inducted into the Thinkers 50 Hall of Fame for her impact on shaping leadership worldwide. Her book, How Women Rise, identifies key habits holding women back in their careers and offers strategies to overcome them.

Connect with Sally:

Sally’s Website: sallyhelgesen.com 

Sally’s LinkedIn: linkedin.com/in/sallyhelgesen 

Sally’s Substack: substack.com/@allrise 

Resources Mentioned:

Sally’s Book, How Women Rise: Break the 12 Habits Holding You Back from Your Next Raise, Promotion, or Job: https://www.amazon.com/How-Women-Rise-Holding-Promotion/dp/0316440124 

Sally’s Book, The Female Advantage: Women's Ways of Leadership: https://www.amazon.com/Female-Advantage-Womens-Ways-Leadership/dp/0385419112 

The Mountain Is You: Transforming Self-Sabotage Into Self-Mastery by Brianna Wiest: https://www.amazon.com/Mountain-You-Transforming-Self-Sabotage-Self-Mastery/dp/1949759229 

Buy Back Your Time: Get Unstuck, Reclaim Your Freedom, and Build Your Empire by Dan Martell: https://www.amazon.com/Buy-Back-Your-Time-Unstuck/dp/059342297X 

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Many brands struggle to connect authentically with Gen Z, often misunderstanding their needs and missing the mark. At just 18 years old, Jake Bjorseth recognized this gap and founded Trndsttrs to help businesses truly understand younger consumers. His relentless focus on Gen Z’s unique mindset and communication style helped him land major clients like McDonald’s and rapidly grow his team. In this episode, Jake joins Kevin to discuss common misconceptions about Gen Z, the importance of understanding consumer behavior, and how brands can rethink marketing strategies to genuinely engage younger audiences.

Jake Bjorseth is the founder of Trndsttrs Media, a 100% Gen Z-owned and operated marketing agency focused on connecting brands with younger consumers through culture-driven storytelling and influencer marketing.

In this episode, Kevin and Jake will discuss:

(00:00) Introduction

(03:11) Building Trndsttrs as a Gen Z Marketing Agency

(05:47) Early Challenges Launching Trndsttrs

(09:59) Unique Mental Health Challenges Facing Gen Z

(13:12) What Employers Get Wrong About Gen Z

(16:50) Why Brands Struggle to Connect with Gen Z

(19:04) Lessons from a Major Brand’s Failed Product Launch

(24:08) Transforming Marketing with Creator Collaborations

(27:41) Rethinking Job Titles to Attract Young Talent

(30:58) How TikTok Shop Is Reshaping Marketing

(32:42) Investing in Yourself to Grow Your Business

Jake Bjorseth is the founder of Trndsttrs Media, a 100% Gen Z-owned and operated marketing agency focused on connecting brands with younger consumers through culture-driven storytelling and influencer marketing. He has collaborated with clients like McDonald’s, L’Oréal, The North Face, and Johnson & Johnson to deliver impactful marketing strategies. Jake is also the co-founder of Sugar AI, a platform bridging gaps in the brand-creator ecosystem.

Connect with Jake:

Jake’s Website: trndsttrs.com 

Jake’s LinkedIn: linkedin.com/in/trndsttr 

Resources Mentioned:

Principles for Dealing with the Changing World Order: Why Nations Succeed and Fail by Ray Dalio: https://www.amazon.com/Changing-World-Order-Nations-Succeed/dp/1982160276 

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Fear, uncertainty, and self-doubt are common obstacles that prevent many from making career changes. Having experienced multiple career transitions herself, Tammy Gooler Loeb found her true calling as a certified career coach, helping others find fulfillment in their work. With over two decades of experience, Tammy empowers individuals to break free from professional ruts and build careers that align with their true passions. In this episode, Tammy joins Kevin to share how to overcome fear, embrace change, and design a career that truly satisfies you.

Tammy Gooler Loeb is a career and executive coach with over 25 years of experience, helping professionals align their careers with their values for greater fulfillment. Her work has been featured in Forbes, Fast Company, and Harvard Business Review.

In this episode, Kevin and Tammy will discuss:

(00:00) Introduction

(02:25) Her Path to Career Coaching

(05:03) The Inspiration Behind Work from the Inside Out

(06:58) Fear: Friend or Foe in Career Change?

(10:06) Finding Meaning in Everyday Work

(14:45) Networking Strategies That Actually Work

(20:50) Understanding the Root of Career Dissatisfaction

(28:59) What Holds People Back From Career Change?

(35:58) Handling Rejections in Career Transitions

(38:33) Discovering What Truly Fulfills You at Work

(42:59) How Coaching Changed Tammy’s Life

Tammy Gooler Loeb is a career and executive coach with over 25 years of experience, helping professionals align their careers with their values for greater fulfillment. She is the author of Work From the Inside Out, which offers strategies for overcoming fear and self-doubt to transform your career. Tammy also hosts the Work from the Inside Out podcast, featuring inspiring career stories. Her work has been featured in Forbes, Fast Company, and Harvard Business Review.

Connect with Tammy:

Tammy’s Website: tammygoolerloeb.com 

Tammy’s LinkedIn: linkedin.com/in/tammygoolerloeb 

Resources Mentioned:

Tammy’s Book, Work from the Inside Out: Break Through Nine Common Obstacles and Design a Career That Fulfills You: https://www.amazon.com/Work-Inside-Out-Obstacles-Fulfills/dp/B09PMLD7WF 

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Many people face chronic health issues, yet don’t realize how much their lifestyle impacts their well-being. Dr. Josh Axe’s journey into functional medicine began with watching his mother struggle through cancer treatments and chronic illness, which sparked his passion for natural healing. Combining modern science with ancient wisdom, he founded the Health Institute, helping millions reverse chronic diseases by focusing on lifestyle, nutrition, and holistic care. In this episode, Josh joins Kevin to share why most diseases start in the gut, how our connections to nature, community, and purpose shape health, and why personalized nutrition and herbal medicine are keys to lasting wellness.

Dr. Josh Axe is a chiropractor, certified doctor of natural medicine, clinical nutritionist, and leadership expert passionate about helping individuals use food and natural remedies to achieve optimal health and wellness.

In this episode, Kevin and Josh will discuss:

(00:00) Introduction 

(02:08) How Natural Medicine Saved His Mom’s Life

(06:50) The Link Between Nature and Longevity

(09:08) Why Purpose Is Essential for Health

(12:19) How to Heal Your Gut for Total Wellness

(15:41) Simple Diet and Lifestyle Shifts for Better Health

(19:53) Is Keto and Intermittent Fasting for Everyone?

(29:50) The Impact of Technology on Human Connection

(31:54) Effective Strategies for Managing Stress

(34:56) How to Navigate Toxic Relationships

(37:34) The Power of Ancient Remedies and Herbal Medicine

Dr. Josh Axe is a certified doctor of natural medicine, clinical nutritionist, and leadership expert passionate about helping individuals use food and natural remedies to achieve optimal health and wellness. He is the founder of The Health Institute and the co-founder of Ancient Nutrition. His businesses have ranked among Inc. 500’s fastest-growing companies. Josh is the host of The Dr. Josh Axe Show and the bestselling author of Eat Dirt, The Keto Diet, and Ancient Remedies.

Connect with Josh:

Josh’s Website: draxe.com 

Josh’s Instagram: instagram.com/drjoshaxe 

Resources Mentioned:

Josh’s Book, Eat Dirt: Why Leaky Gut May Be the Root Cause of Your Health Problems and 5 Surprising Steps to Cure It: https://www.amazon.com/Eat-Dirt-Health-Problems-Surprising/dp/0062433644 

Josh’s Book, Think This, Not That: 12 Mindshifts to Breakthrough Limiting Beliefs and Become Who You Were Born to Be: https://www.amazon.com/Think-This-Not-That-Breakthrough/dp/1400337844 

Josh’s Podcast, The Dr. Josh Axe Show: https://podcasts.apple.com/us/podcast/the-dr-josh-axe-show/id1700689487 

The Health Institute: thehealthinstitute.com 

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Furniture shopping can be overwhelming, with countless choices, hidden fees, and confusing quality differences. Recognizing this gap in the market, Alex Back used his e-commerce experience to build couch.com, simplifying the process for both consumers and retailers. His platform not only helps consumers navigate the complex world of furniture but also delivers qualified, ready-to-buy leads to retailers. In this episode, Alex joins Kevin to discuss how couch.com is disrupting the furniture industry, the biggest blind spots facing both buyers and retailers, and how to turn indecision into a streamlined, confident shopping experience.

Alex Back is the founder and CEO of Couch.com, a platform offering expert reviews and personalized recommendations to simplify furniture shopping. With over 15 years of experience in retail and e-commerce, Alex has worked with partners like Costco and Amazon and has been featured in Forbes and CNN.

In this episode, Kevin and Alex will discuss:

(00:00) Introduction 

(02:10) How couch.com Simplifies Furniture Shopping

(08:11) The Truth About ‘Free’ Furniture Returns

(10:14) The Importance of Consumer Education

(14:19) Breaking the Blame Cycle in Furniture Sales

(19:24) Building a Community-Based Approach to Sales

(21:15) Pivoting and Adapting in Business

(24:36) Overcoming Indecision in Furniture Shopping

(29:06) Investing in Personal Growth

(33:17) The Value of Networking and Masterminds

Alex Back is the founder and CEO of Couch.com, a platform offering expert reviews and personalized recommendations to simplify furniture shopping. He previously co-founded Apt2B, an online furniture retailer that grew from a Hollywood studio apartment to over $40 million in annual revenue before its successful acquisition. With over 15 years of experience in retail and e-commerce, Alex has worked with partners like Costco and Amazon and has been featured in Forbes and CNN.

Connect with Alex:

Alex’s Website: alexback.com 

Alex’s LinkedIn: linkedin.com/in/alex-back-49784435 

Alex’s Email:  [email protected] 

Resources Mentioned:

Couch.com’s Website: https://couch.co

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How do you overcome the curveballs life throws at you? At 23 years old, Amy Morin's mother suddenly passed away, and just three years later, she lost her husband to a heart attack. Overwhelmed by grief, Amy tried various conventional methods to cope, but nothing seemed to help. It wasn’t until she began studying mental strength that she realized the key to healing wasn’t just moving on from loss; it was about building resilience in the face of adversity. In this episode, Amy joins Kevin to discuss how mental strength can be a game-changer in navigating life’s toughest challenges without feeling broken.

Amy Morin is a psychotherapist, bestselling author, and expert in mental strength. She has delivered keynote speeches for top organizations like Google and Microsoft, and her articles on mental strength reach more than 2 million readers monthly.

In this episode, Kevin and Amy will discuss:

(00:00) Introduction 

(02:17) Discovering Mental Strength Amid Tragic Losses

(06:16) What Is Mental Strength?

(08:07) Shifting Mindsets to Solve the Right Problems

(17:34) The Five Stages of Change

(23:27) Using External Motivation to Drive Action

(24:55) Rewiring Your Thoughts Through Writing 

(30:19) Internal vs. External Locus of Control

(33:38) How to Keep Moving When You Feel Stuck

(35:35) Overcoming Anxiety to Become a Global Speaker

(40:42) The Key to Conquering Anxiety and Depression

Amy Morin is a psychotherapist, bestselling author, and expert in mental strength. She is the author of six books, including 13 Things Mentally Strong People Don’t Do, all of which have sold over a million copies and been translated into more than 40 languages. Amy's TEDx talk, "The Secret of Becoming Mentally Strong," has gained over 24 million views. She has delivered keynote speeches for top organizations like Google and Microsoft, and her articles on mental strength reach more than 2 million readers monthly.

Connect with Amy:

Amy’s Website: amymorinlcsw.com 

Amy’s LinkedIn: linkedin.com/in/amymorinlcsw 

Resources Mentioned:

Amy’s Book, 13 Things Mentally Strong People Don't Do: https://www.amazon.com/Things-Mentally-Strong-People-Dont/dp/0062358308 

Amy’s TED Talk: youtube.com/watch?v=TFbv757kup4 

Buy Back Your Time: Get Unstuck, Reclaim Your Freedom, and Build Your Empire by Dan Martell: https://www.amazon.com/Buy-Back-Your-Time-Unstuck/dp/059342297X 

Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones by James Clear: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299 

From Stuck to Breakthrough:

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This FREE, five-day live experience will help you uncover hidden solutions to your toughest challenges—whether it’s in your business, health, wealth, or relationships.

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Many leaders unknowingly struggle with blind spots that prevent them from seeing their team’s true potential. With over 25 years of experience in HR coaching and leadership development, R. Karl Hebenstreit has witnessed how bias and a closed mindset in leadership can negatively impact team dynamics. By using tools like the Enneagram, he helps leaders identify their challenges, understand their teams, and unlock higher performance and better employee retention. In this episode, Karl joins Kevin to discuss how the Enneagram can uncover blind spots, enhance leadership effectiveness, and build stronger, more cohesive teams.

R. Karl Hebenstreit is an author, international speaker, executive coach, and human resources and organizational development leader with over 25 years of experience. He has worked with top organizations such as Merck and AT&T.

In this episode, Kevin and Karl will discuss:

(00:00) Introduction 

(02:40) His Journey into Leadership Development

(03:59) Why Relying on One Solution Limits Success

(06:03) How the Johari Window Broadens Perspectives

(10:15) The Key to Boosting Employee Engagement

(12:59) Understanding Enneagram Types for Better Leadership

(17:13) The Oz Principle and Personal Accountability

(19:33) How to Apply the Enneagram Checklist

(22:40) Uncovering Leadership Blind Spots with the Enneagram

(31:31) Leveraging AI in Leadership Coaching

R. Karl Hebenstreit is an author, international speaker, executive coach, and human resources and organizational development leader with over 25 years of experience. He is the founder of Perform & Function, LLC, where he helps enhance individual, team, and organizational performance. Karl holds a Ph.D. in Organizational Psychology and is a certified Professional Certified Coach (PCC). He has worked with top organizations such as Merck and AT&T.

Connect with Karl:

Karl’s Website: performandfunction.com

Karl’s LinkedIn: linkedin.com/in/rkarlhebenstreit 

Karl’s Email: [email protected]

Resources Mentioned:

Karl’s Book, The How and Why: Taking Care of Business with the Enneagram: https://www.amazon.com/How-Why-Taking-Business-Enneagram-ebook/dp/B0CJLQGS3K 

Karl’s Book, Explicit Expectations: The Essential Guide & Toolkit of Management Fundamentals: https://www.amazon.com/Explicit-Expectations-Essential-Management-Fundamentals-ebook/dp/B0D4KXSH4F 

From Stuck to Breakthrough:

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