The Time Freedom Podcast

Brian Herriot, Kirby Denison
  • 5.0 (2)
  • Entrepreneurship
  • Updated Weekly

Work hard, save more, retire someday—right? What if you could live fully now? The Time Freedom Podcast with Brian Herriot and Kirby Denison shows you how to blend flexible work and smart investing to cover your lifestyle, build security, and create more time for what matters—often in just three years. Learn the Time Freedom Formula, design your ideal life, and join the growing freetimer community. It’s not about work-life balance. It’s about a whole new way to live. Subscribe to The Time Freedom Podcast and start your journey to more freedom, more control, and more life—today.

  1. Jun 2

    Building Time Freedom in Public: The Season 2 Finale

    Top 5 Takeaways:  Time freedom doesn't have to come at the end. Listener stories: Audrey dancing ballet in Mexico, Matthew working 15 hours a week from Canada, show people designing the life now rather than waiting for some finish line.  Your voice is part of the message. When a book weaves personal stories in with the frameworks, narrating the audiobook yourself builds trust and rapport faster than a hired reader or an AI voice ever could. New skills take reps before they take off.  Brian's first keynote went blank mid-speech, and he walked away more committed, not less. Mastery lives on the other side of looking bad in public.  Get specific about your path. Season 3 trades general advice for six listener avatars—from the DIY money person to the near-retiree—each getting a three-episode series that maps out exactly how they'd reach time freedom.  You don't have to do it alone. Big life changes are where support matters most. The Time Freedom Community (launching October) turns the book into group coaching, shared accountability, and relationships with others on the same path. Chapters: 00:00 Season Two Reflections and Lessons Learned 02:49 Growing the Time Freedom Community 05:13 Behind the Scenes of the Book and Audiobook Launch 10:05 Listener Feedback and the Impact of Shared Stories 17:01 Looking Ahead to Season Three 20:03 Understanding the Different Paths to Time Freedom 26:28 Building Connection, Community, and Support 32:36 Brian's Speaking Journey and Future Vision 37:07 Special Offers, Giving Back, and What's Next Summer Offer: Get More, Give More For 60 days only (June 15–August 15) get six months in the Time Freedom Community 25 copies of the book (one signed, the rest to share or to have Brian and Kirby place with ideal readers) A one-hour webinar Brian will deliver for your clients  Most of the cost goes to the books, and Brian's proceeds (about $100) are donated in your name to Donate Life America, supporting registerme.org and donor families. Claim it at timefreedom.life/summeroffer.     🎧 Pre-order Time Freedom and get the audiobook FREE today. Normally it takes three copies to unlock the audiobook, but for podcast listeners, just one. 👉timefreedombook.com | code: PODCAST Enter code PODCAST and you'll get instant access (your paper copy arrives in September). Pre-orders help the book land on more shelves on launch day, so thank you!

    41 min

  2. May 26

    Tim Jenkins and Darran Littlefield Built Time Freedom Before It Had a Name

    Top 5 Takeaways: Time freedom doesn't have to come at the end. Tim and Darran built it into Point B from the very beginning, designing work around their lives rather than the other way around. Company culture is like a bank. If everyone makes deposits, it scales infinitely. If people only make withdrawals, it quietly collapses. The CEO isn't the keeper of culture, because everyone is. Partnerships survive when you commit to them like a marriage. Tim, Darran, and their third co-founder Jim Hodge made a five-year no-exit pact and stayed unified through it all. You have time capital and financial capital, and the ratio shifts throughout your life. Managing both intentionally is the real game. Retirement is a myth. Work isn't the opposite of freedom. When you get the work right, it's what sustains you. The goal isn't to stop, but to find work worth doing until you can't anymore. Chapters:  00:00 Introduction and Everyday Leadership 07:35 The Origins and Vision Behind Point B 12:15 Building an Intentional Company Culture 16:23 Rethinking Consulting and Flexible Work 22:31 Time Freedom vs. Financial Freedom 30:07 The Power of Partnerships and Collaboration 38:13 Culture, Leadership, and Employee Well-Being 40:38 Redefining Retirement and Work-Life Balance 45:17 Career Transitions, Contribution, and Community 54:22 Introduction to Time Freedom Book Promotion TIM JENKINS is the co-founder and former co-CEO of Point B, Inc., a national management consulting firm he built from three partners in 1995 to a 100% employee-owned firm with over a thousand professionals. In 2010 he was named Ernst and Young's Entrepreneur of the Year in Services for the Pacific Northwest. Today he is President of Colchuck, a purposeful private investment company based in Leavenworth, Washington, where he focuses on backing founders who are doing well and doing good at the same time. You can connect with Tim on LinkedIn. DARRAN LITTLEFIELD is the co-founder and former co-CEO of Point B, Inc., where he helped build one of the most admired people-first cultures in the consulting industry. He served alongside Tim for nearly two decades before the founders transitioned full ownership to their employees through an ESOP. Darran now lives in Dallas, Texas, where he relocated to be closer to family, and continues to collaborate with Tim on new work. You can connect with Darran on LinkedIn.   🎧 Pre-order Time Freedom and get the audiobook FREE today. Normally it takes three copies to unlock the audiobook, but for podcast listeners, just one. 👉timefreedombook.com | code: PODCAST Enter code PODCAST and you'll get instant access (your paper copy arrives in September). Pre-orders help the book land on more shelves on launch day, so thank you!

    55 min

  3. May 19

    Dr. Sam Chenkin: There's No Finish Line for Health or Money

    Top 5 Takeaways: The basics never die. In fitness, it's squat, hinge, push, pull, carry, and power. In finance, it's consistent saving and investing over time. Mastering the fundamentals, and doing them well, beats chasing trends in both. Choose your hard. You can do the hard work of investing in your health now, proactively, or you can face the harder consequences of neglect later. There's no avoiding hard–only choosing which kind. Health and wealth both require progression. Just as fitness requires increasing difficulty over time to keep producing results, your financial plan needs to evolve. Doing the same thing forever eventually stops working. Identity drives sustainability. Doing something to get ready for a deadline is not a habit. Real, lasting change requires becoming the kind of person who does the thing and not just someone who's temporarily trying. There is no finish line. Health, fitness, and financial wellbeing aren't problems you solve and move on from. They require ongoing commitment which only feels sustainable if they become part of who you are. Chapters:  00:00 Introduction to Health, Freedom, and Reinvention 03:58 Sam’s Journey from Exercise Physiology to Entrepreneurship 09:18 Why Coaching and Accountability Matter 14:55 Navigating Pain, Injury, and Recovery 17:32 Building a Flexible Health and Wellness Business 22:46 Life Pivots, Setbacks, and Growth 25:53 The Parallels Between Fitness and Finance 27:49 Consistency Over Complexity 33:28 Creating Personalized Health Freedom 36:39 Time Freedom Book Promotion DR. SAM CHENKIN Dr. Sam Chenkin is a chiropractor, exercise physiologist, and personal trainer based in Alameda, California. She holds a Bachelor's in Exercise Physiology from the University of Miami, a Master's in Exercise Physiology and Nutrition from LIU Brooklyn, and a Doctorate of Chiropractic from Palmer College of Chiropractic Florida. Dr. Chenkin recently launched her own training and rehab business, Pivot 2 Health, offering virtual and in-person services built around personalized, long-term health. Her motto: Move, Heal, Thrive. You can connect with Sam at pivot2health.net.   🎧 Pre-order Time Freedom and get the audiobook FREE today. Normally it takes three copies to unlock the audiobook, but for podcast listeners, just one. 👉timefreedombook.com | code: PODCAST Enter code PODCAST and you'll get instant access (your paper copy arrives in September). Pre-orders help the book land on more shelves on launch day, so thank you!

    37 min

  4. May 12

    Lee LeFever on Building a Business Around Your Life (Not the Other Way Around)

    Top 5 Takeaways: Find the one idea you can make synonymous with yourself. Lee built his entire career around explanation, and that single thread connected Common Craft, two books, a Google partnership, and a new Substack. You get to define what shareholder value means. If you're the only stakeholder, you can choose to maximize time instead of money. Just because you design your business around your lifestyle doesn't mean you can't still have ambition. Stepping back gives you the brain space to make creative connections. A monetorium is a temporary, purposeful season of reduced spending that builds anticipation and reveals what you actually need. Happiness lives in anticipation. Design your life around quality, not quantity. You don't need a mansion to show off. The better option is having a home worth spending time in, right down to the perfect plants in your office. Chapters: 0:00 – Introduction to Lee LeFever & Common Craft 1:40 – Personal Background & Designing an Intentional Life 7:05 – Moving to Orcas Island & Lifestyle Design 12:39 – The Birth of Common Craft & Explainer Videos 17:55 – The Science of Explanation 23:09 – The Internet, Niche Markets & Opportunity 25:49 – Authenticity in Communication 27:08 – The “Monitorium” & Values-Based Spending 31:29 – Craftsmanship, Creativity & Personal Projects 36:17 – AI, Human Connection & the Future of Communication LEE LEFEVER Lee LeFever is the co-founder of Common Craft, the company behind some of the internet's earliest and most recognizable explainer videos. His "in Plain English" video series helped millions of people understand emerging technologies like RSS, Twitter, and wikis, and landed Common Craft a partnership with Google. Lee is the author of The Art of Explanation and Big Enough, a book about designing a business around your life. You can connect with Lee at leelefever.com, commoncraft.com, and scienceofexplanation.com.   🎧 Pre-order Time Freedom and get the audiobook FREE today. Normally it takes three copies to unlock the audiobook, but for podcast listeners, just one. 👉timefreedombook.com | code: PODCAST Enter code PODCAST and you'll get instant access (your paper copy arrives in September). Pre-orders help the book land on more shelves on launch day, so thank you!

    45 min

  5. May 5

    Katrina McGhee Is a Digital Nomad but Maybe Not for Long

    Top 5 Takeaways: Variation creates appreciation. Doing different things in life, like working then resting or traveling then staying put, makes you appreciate what you did before and what might come next. The contrast is the point. Consider a career break in the first part of Year 2. If you're following the No-Hustle Transition to entrepreneur, don't just flip from employee to business owner. Take a real break first. Even just three months to decompress. You'll be more productive in the nine months that follow than if you white-knuckled through all twelve. A career break "cracks people open" to living differently. Many of Katrina's clients are corporate 9-to-5ers who return from their breaks realizing they can design life on their own terms, not just go back to the way things were. Plans are cute. It's good to have goals, but always take advantage of the random opportunities that come your way.  Digital nomad life has pros and cons, just like traditional living. After eight years of location independence, Katrina is considering settling down for easier dating, fitness routines, and mental space to grow her business. Every lifestyle has its trade-offs. Chapters: 0:00 – Introduction to Katrina McGhee 1:21 – The Digital Nomad Lifestyle Explained 4:09 – The Power of Career Breaks 6:51 – Transitioning into Remote Work & Coaching 9:39 – From Nomadic Living to a Home Base 12:27 – Building a Flexible Coaching Business 15:10 – The “No Hustle” Transition Approach 17:44 – Planning for the Future with Flexibility 32:24 – Navigating Career Transitions & Uncertainty 36:37 – Building a Brand Around Career Breaks KATRINA MCGHEE Katrina McGhee is a career break and sabbatical coach, digital nomad, and author of Taking a Career Break for Dummies. During her first career break, she traveled the world for 20 months. In her next, she left her corporate job a second time to build her coaching business. Katrina is the co-founder of BreakSpace, the membership community for career breakers and sabbatical takers. You can connect with Katrina at kmcgheecoaching.com or listen to her podcast, Taking a Career Break with Katrina McGhee.   🎧 Pre-order Time Freedom and get the audiobook FREE today. Normally it takes three copies to unlock the audiobook, but for podcast listeners, just one. 👉timefreedombook.com | code: PODCAST Enter code PODCAST and you'll get instant access (your paper copy arrives in September). Pre-orders help the book land on more shelves on launch day, so thank you!

    44 min

  6. Apr 28

    Want More Serendipity? Laura Vanderkam Says to Say Yes More Often

    Top 5 Takeaways: "I don't have time" really means "it's not a priority." Changing that language reminds you that time is a choice. Saying yes to things that intrigue you, even small or unfamiliar ones, is how new opportunities find you. Active patience means doing your part so time can do its part. "Not yet" doesn't mean never. Complexity is not the same as chaos. A well-run life can have a lot going on and still feel orchestrated. You have 8,760 hours in a year. When you track them, you start to see space where you thought there was none. Chapters:  0:00 – Introduction to Laura Vanderkam & Time Management 10:34 – What Time Abundance Really Means 15:25 – Active Patience & Long-Term Thinking 23:37 – The Role of Feedback in Growth 26:24 – Life as a “Circus” (and Why That’s Okay) 28:10 – The One-Year View on Time 31:02 – Prioritizing What Truly Matters 32:41 – Time, Kids, and Accountability 34:33 – Key Reflections & Final Insights 37:07 – Time Freedom Book Promotion LAURA VANDERKAM Laura Vanderkam is a bestselling author, speaker, and one of the leading voices on time management and productivity. She's the author of seven books on time, including 168 Hours, Tranquility by Tuesday, Off the Clock, and her newest, Big Time: A Simple Path to Time Abundance. Laura’s work has appeared in The New York Times, The Wall Street Journal, Fast Company, and Fortune. She's a Princeton grad and lives outside Philadelphia with her husband and five children. You can connect with Laura at lauravanderkam.com.   🎧 Pre-order Time Freedom and get the audiobook FREE today. Normally it takes three copies to unlock the audiobook, but for podcast listeners, just one. 👉timefreedombook.com | code: PODCAST Enter code PODCAST and you'll get instant access (your paper copy arrives in September). Pre-orders help the book land on more shelves on launch day, so thank you!

    38 min

  7. Apr 21

    Les Sherry Built Time Freedom Inside a Corporate Career

    Top 5 Takeaways: A job is just a job, not a career. When you're good at what you do, leaving a role is far less risky than most people think. You don't have to be an entrepreneur to live with time freedom. Les achieved it through a traditional career by making intentional choices over time. Post-adventure depression is real. Finishing a big, consuming goal can leave a hole that catches you off guard. Retire into something, not away from something. The four phases of transition (vacation, loss of purpose, exploration, new purpose) explain why so many retirees go back to work. There are things you can only do at certain times in life. Waiting for the “right time” can mean the window closes entirely. Chapters: 0:00 – Introduction and Les Sherry’s Background 2:19 – The Desire for Time Freedom 5:02 – Planning a Year-Long Family Adventure 7:36 – What It’s Really Like Traveling as a Family 10:07 – Coming Home and Reintegrating 12:30 – Transitioning Away from Traditional Work 14:57 – Finding Purpose After the Journey 17:15 – Key Lessons from a Year Abroad 37:30 – The Four Phases of Transition Explained 49:36 – Coaching, Independence, and What’s Next LES SHERRY  Les Sherry is an ICF certified executive coach with over 30 years of leadership experience across consulting, healthcare, and technology. He spent 11 years at Accenture before joining Kaiser Permanente, where he worked for nearly two decades. In 2012, smack in the middle of his Kaiser career, Les and his family packed their backpacks (100 pounds total) and spent a year traveling to 23 countries across six continents. Since retiring, he's picked up fly fishing, fly tying, piano, Muay Thai kickboxing, and is training to teach yoga. You can connect with Les on LinkedIn.   🎧 Pre-order Time Freedom and get the audiobook FREE today. Normally it takes three copies to unlock the audiobook, but for podcast listeners, just one. 👉timefreedombook.com | code: PODCAST Enter code PODCAST and you'll get instant access (your paper copy arrives in September). Pre-orders help the book land on more shelves on launch day, so thank you!

    55 min

  8. Apr 14

    Dr. Seema Desai Finds Joy as a Keynote Speaker and Freetimer

    Top 5 Takeaways: Happiness is fleeting and external. Joy is self-sourced. Only 10% of our experience comes from external circumstances. The other 90% is up to us. More time doesn't equal more success. You can get there faster by working fewer hours with a refreshed attitude than by grinding it out. Follow the breadcrumbs. Seema left dentistry with no plan and let opportunities show up as she aligned with her values. Perspective changes everything. Seema's husband comes home from losing patients and sees their own chaos as a gift, not a problem. Privilege is a gift when used responsibly. The question isn't whether you have it, but whether you're using it to serve others or just yourself. Chapters: 0:00 – Welcome and Introduction to the Episode 2:25 – What Time Freedom Really Means 4:59 – Personal Transformations and Influences 7:35 – Life Choices and Career Direction 10:13 – Cultural Background and Early Challenges 12:35 – The Path to Coaching and Self-Discovery 15:08 – Midlife Reflections and Redefining Happiness 17:39 – Priorities, Alignment, and Intentional Living 23:48 – Happiness vs. Joy: What’s the Difference? 32:22 – Privilege, Responsibility, and Living with Purpose DR. SEEMA DESAI  Dr. Seema Desai is a leadership coach, speaker, and author who helps high-achieving professionals stop chasing happiness and start building joy. A former dentist, Seema walked away from her practice to pursue a more aligned life, guided by the belief that joy is the strategy for creating your next competitive edge. She holds a Doctor of Dental Surgery degree and is a graduate of Heroic Public Speaking. Seema lives in Austin, Texas with her husband and two children.  You can connect with Seema at drseemadesai.com   🎧 Pre-order Time Freedom and get the audiobook FREE today. Normally it takes three copies to unlock the audiobook, but for podcast listeners, just one. 👉timefreedombook.com | code: PODCAST Enter code PODCAST and you'll get instant access (your paper copy arrives in September). Pre-orders help the book land on more shelves on launch day, so thank you!

    41 min
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About

Work hard, save more, retire someday—right? What if you could live fully now? The Time Freedom Podcast with Brian Herriot and Kirby Denison shows you how to blend flexible work and smart investing to cover your lifestyle, build security, and create more time for what matters—often in just three years. Learn the Time Freedom Formula, design your ideal life, and join the growing freetimer community. It’s not about work-life balance. It’s about a whole new way to live. Subscribe to The Time Freedom Podcast and start your journey to more freedom, more control, and more life—today.

Information

  • Creator
    Brian Herriot, Kirby Denison
  • Years Active
    2023 - 2026
  • Episodes
    41
  • Rating
    Clean
  • Copyright
    © 2025
  • Show Website
    The Time Freedom Podcast

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