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. 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

  2. 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

  3. APR 7

    Ruby Ryba on Packing a Full Life Into One Life

    Top 5 Takeaways: Give each day a single focus. Instead of cramming work, family, self-care, and social time into every day, Ruby picks one theme per day. It stopped her from feeling like she was failing at everything. Accept the seasons of "time broke." With young kids, certain hours of the day are just spoken for. Accepting that (instead of resenting it) frees up the hours you do control. You don't have to be with someone all the time to love them. Ruby and her husband travel without their kids regularly, and she's normalizing it for her family. The guilt fades when you see how good it is for everyone. Fill the vacuum. Removing scrolling from your life forces a question most people avoid: what do you actually want to do with your time? That's what makes the change stick. Design over willpower. You can meet a friend at the bakery and resist the croissant, or you can meet them at the smoothie place and skip the battle entirely. The same principle applies to your phone. Chatpers: 0:00 – Welcome and Early Personal Insights 1:16 – From High School Math Teacher to Author 5:36 – Generational Perspectives on Time Freedom 10:26 – Freedom, Autonomy, and Designing Your Life 13:40 – Entrepreneurship and Intentional Life Choices 17:19 – Time Freedom Across Different Life Stages 25:30 – The Story Behind Writing How to Stop Scrolling 30:00 – Understanding the Reader and the Problem of Phone Use 31:14 – Reclaiming Time and Attention in a Digital World 34:27 – Building Meaningful Connections and Adult Friendships RUBY RYBA Ruby Ryba is a former high school math teacher turned screen time strategist and the author of How to Stop Scrolling, out March 30th. After teaching algebra and AP statistics for years, Ruby pivoted during COVID to pursue writing and coaching, blending her analytical background with a passion for helping people be more intentional with their time and attention. She hosts a weekly writing circle through the Write Useful Books community and publishes The Scroll Shift, a weekly newsletter with actionable advice on redesigning your relationship with your phone. You can connect with Ruby at howtostopscrolling.com and rubyrybawrites.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!

    42 min

  4. MAR 31

    Paul Merriman on Managing $1.6 Billion But Never His Own Money

    Top 5 Takeaways: Aim for more than enough. John Bogle preached "enough." Paul respectfully disagrees. Most people never reach their goal, and bad things happen. A cushion of more than enough is what actually lets you relax. The “two funds for life” strategy is powerful in its simplicity: a target date fund plus a small cap value index fund. That's it. It came from John Bogle shaking his finger at Paul and saying, "You cannot ask investors to manage 10 different funds." Staying the course is the whole game. Paul managed billions in other people's money but won't manage his own because he knows the emotional pull is too strong. If he can't trust himself to stay rational, the rest of us should take that seriously. The best first step is invisible. Auto-enroll in a 401k, put it in a target date fund, and never look at it. Boring is the strategy. It's also the one that actually works over 40 years. Find work you'd do forever and you'll never need to fully retire. Paul started his firm from a set of affirmations at age 40. At 82, he's up before 4 AM reading and creating content. His whole life now "feels like weekends." Chapters: 0:00 – Meet Paul Merriman 3:04 – Early Influences and Background in Investing 8:21 – Paul’s Journey from Investor to Educator 13:38 – Why He Shifted from Managing Money to Teaching 17:07 – Selling the Firm and Redefining Purpose 24:00 – The “2 Funds for Life” Strategy Explained 29:59 – Why Staying the Course Matters 34:06 – Emotional Challenges in Modern Investing 36:54 – The Power of Compound Interest and Long-Term Thinking 41:05 – Defining “More Than Enough” and Building a Legacy PAUL MERRIMAN Paul Merriman is a financial educator, author, and the founder of the Merriman Financial Education Foundation, where he’s devoted himself full-time to free financial education for do-it-yourself investors. Paul is the author of We're Talking Millions: 12 Simple Ways to Supercharge Your Retirement, which he gives away for free. You can connect with Paul at paulmerriman.com and download his free books at paulmerriman.com/free-books.   🎧 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!

    53 min

  5. MAR 24

    Vickie Lanthier Turned Down Six Figures to Work Half the Year

    Top 5 Takeaways: Your buffers aren't just financial. Vickie identifies four: financial, health, paperwork and plans, and skills. When life goes sideways, it's the combination that determines how fast you recover. Selling the house and the stuff bought her something more valuable than equity. It bought her time and space to pivot without the weight of debt and maintenance pulling her under. You can turn down more money if the cost is your time and energy. Vickie walked away from six-figure contract offers because the real price wasn't worth it. Switching off autopilot requires six neurological components: buy-in, stimulation, intervention, reflection, sleep, and repetition. You can't just want to change; you have to create the conditions for it. Living big doesn't require a specific income level. Vickie works about half the year, makes a fraction of her old salary, and is currently living in Albania for two months because she designed her life to allow it. Chapters: 0:00 – How Major Life Events Shape Personal Growth 3:38 – Career Challenges and the Path Toward Financial Freedom 6:11 – Minimalism and the Pursuit of Time Freedom 14:53 – Navigating Life’s Difficult Moments with Support 17:53 – Discovering New Opportunities Through Time Freedom 21:02 – The Power of Life Buffers: Money, Health, Skills, and Systems 24:37 – What It Means to Be a High Agency Human 27:11 – Breaking Out of Autopilot and Living Intentionally 34:59 – Writing a Book to Create Impact 36:37 – Building Community and Sharing the Message VICKIE LANTHIER Vickie Lanthier is a decorated Canadian military veteran, registered nurse, author, and the founder of High Agency Human. Now a registered nurse, she started a hiking resource business that has donated over $27,000 to mental health and conservation charities since 2020, and is currently racing a friend to visit 50 countries. Her new book, High Agency Human: Navigate Adversity and Live Big, comes out March 24, 2025. Connect with Vickie at highagencyhuman.com, or find her on Instagram and LinkedIn at Vickie Lanthier.   🎧 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!

    39 min

  6. MAR 17

    Rebecca Herbst on How Freedom Made Her a More Generous Person

    Top 5 Takeaways: Financial independence (FI) doesn't mean your life is figured out. Rebecca reached FI at 32 and says it’s taken years to design a life she loves. Moving from a low cost of living city back to a high cost one was the right call for Rebecca's family, even though it technically moved her further from “full FI.” Life design matters more than the number. Time freedom with toddlers is real, but it looks different. It's not about open calendars. It's about having the option to be present and sharing the load with your partner. You don't have to be a billionaire to make a meaningful charitable impact. Rebecca's philanthropy pledge starts at just 1% of income, and the math works out to about $100 a month for many people. Proactive giving feels better and has more impact than reactive giving. Rebecca recommends a three-bucket framework: family, emotional connection, and measurable impact. Chapters:  0:00 – Welcome and Personal Connections 1:12 – Meet Rebecca Herbst and Her Financial Independence Journey 4:25 – Early Career and the Path to FI 6:17 – Achieving Financial Independence at 32 8:35 – Parenthood and the Realities of Financial Independence 13:54 – How Time Freedom Changes with Life Stages 21:10 – Balancing Family Life and Time Freedom 23:09 – The 1% Pledge and the Power of Charitable Giving 32:53 – How to Give More Effectively and Measure Impact 40:53 – Using Finance as a Force for Good REBECCA HERBST  Rebecca Herbst is the founder of Yield and Spread, a nonprofit on a mission to promote finance as a force for good. A former competitive rower turned early retiree, Rebecca left her career in commercial real estate in her early 30s after reaching financial independence alongside her husband Joe. She lives in Salt Lake City with her husband, their two-year-old son, and a baby girl arriving very soon! You can connect with Rebecca at yieldandspread.org.   🎧 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

  7. MAR 10

    Veena Harbaugh and Trevor Blondeel Put Time Freedom to the Test

    Top 5 Takeaways: Running the numbers creates relief. Both Veena and Trevor describe the same feeling: once you see it on paper, fear turns into confidence. You don't have to prove your value. Veena's biggest mindset shift was letting go of the belief that she had to constantly earn her worth. Money personalities can improve relationships. Trevor and his wife had better conversations once they understood their different styles. Working longer can be more freeing than retiring early. If you love your work, extending it beats sacrificing now for some future number. Some of the best people you meet come later in life. Trevor reminds us that new friendships can be just as meaningful as old ones. Chapters: 0:00 – Why the Time Freedom Calculator Brings Relief 1:07 – Meet Trevor + Veena (Background + What They Do) 2:43 – Welcome + How They Know Brian (AJ Harper Writing Community) 3:13 – Beliefs That Changed (Time, Identity, and Proving Yourself) 9:20 – Life Stage Snapshot: Work, Marriage, Kids, Entrepreneurship 10:39 – What Time Freedom Means (Choices, Impact, and Agency) 11:55 – The Calculator Effect: Seeing a 6-Month Dip as a “Small Blip” 12:18 – Real-Life Optionality: Being Present for Family When It Matters 18:23 – Money Styles + Better Money Conversations With Partners 24:42 – The Books They’re Writing + Designing Life 10 Years Out VEENA HARBAUGH  Veena Harbaugh is a sustainability strategist based in the Bay Area. She spent over a decade helping Fortune 500 companies build environmental and social programs that actually work. Veena is currently writing her first book, Meet the Moment, a guide for change-makers who want to stay effective without burning out. You can connect with Veena at veenaharbaugh.com. TREVOR BLONDEEL  Trevor Blondeel spent 25 years leading manufacturing operations before launching his own consulting and coaching business. He helps leaders in manufacturing, logistics, and construction get better results by building trust and accountability through real conversations. Trevor hosts the Manufacturing Greatness podcast and is writing a book by the same name. You can connect with Trevor at trevorblondeel.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!

    40 min

  8. MAR 3

    AJ Harper Built Her Dream Life Around Authorship

    Top 5 Takeaways: You can design your work around your ideal life. AJ built a studio that funds her dream lake home. Thinking in "seasons" beats rigid daily time blocks. Intense work periods are sustainable when you know they'll end. Writing is a learnable craft, not just a natural talent. Commitment to learning matters more than innate ability. The mindset "my art will sustain me" becomes a self-fulfilling prophecy. Limiting beliefs about creative work hold people back. If you want to become an author, start by reading, and get honest about what level of success you actually want. Chapters:  0:00 – Introduction + Why Sustainable Authorship Matters 3:05 – AJ Harper’s Time Freedom Journey 8:11 – Inside the Publishing World: From Insider to Strategist 12:58 – Taking Risks & Choosing the Entrepreneurial Path 15:06 – Seasonal Living: New York & Madeleine Island 20:27 – Designing a Flexible, Intentional Life 24:59 – Transitioning Fully Into Authorship 29:52 – Craft, Mindset & the Making of a Sustainable Writer 43:14 – Building a Body of Work (Not Just One Book) 47:34 – Creative Freedom + Where to Find AJ AJ HARPER AJ Harper is an author, book coach, and collaborative writer behind multiple bestselling books, including her work with Mike Michalowicz on Profit First and the upcoming The Money Habit. She's the author of Write a Must-Read and creator of the Top Three Book Workshop, where she helps authors write books that actually deliver on their promise. AJ is also co-host of the Don't Write That Book podcast. You can connect with AJ at ajharper.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!

    48 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
    35
  • Rating
    Clean
  • Copyright
    © 2025
  • Show Website
    The Time Freedom Podcast

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