The Time Freedom Podcast

Brian Herriot, Kirby Denison
  • 4.8 (20)
  • Entrepreneurship
  • 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. 3d ago

    Are You Ready for the Next Crash? There’s Always One

    ➡️ Get the free Fast Follow bonus chapter: https://timefreedom.life/fastfollow➡️ Buy TIME FREEDOM, the Book: https://timefreedom.life/book In March 2020, Brian watched his portfolio drop by about $50,000 a day. After 23 years of saving, he was just about ready to start using that money, so he panicked and sold everything to cash. That locked in a $200K loss, and then he missed a $300K rebound. It was a half-million-dollar mistake. Brian and Kirby dig into the problem most buy-and-hold investors don’t face until it’s too late: what happens when the market crashes right when you need your money. They cover why a 50% drop takes a 100% gain to recover, why losses hurt about twice as much as gains feel good, and why holding cash or shifting to bonds doesn’t fully solve the problem. Brian also shares what his current approach, fast follow investing, would have done during that same 2020 crash. Next week, they get into how it works. Top 5 Takeaways: A crash hits differently when you need the money. When you’re young and still saving, a drop just means buying shares at a discount. When you’re about to use your savings, the same drop can push your plans back by years.Losses take more to recover than you think. A 50% drop needs a 100% gain to get back to even, and a 90% drop needs 900%. Keep losses near 20% and you only need a 25% gain to recover.Losses feel worse than gains feel good. Research suggests a loss hurts about twice as much as an equal gain, which is why so many investors sell at the bottom, like Brian did.Getting out is only half the problem. Brian’s biggest cost wasn’t the $200,000 loss but the $300,000 rebound he missed by staying in cash. A good strategy has to get you back in, too.Cash and bonds help, but they have trade-offs. A cash reserve lets you wait out a downturn but doesn’t manage the loss. Bonds lower your returns and don’t always protect you; in 2022, stocks and bonds fell together. Fast follow aims to limit losses while still earning a strong return.Chapters00:00 The 2020 losses that prompted a new investing approach06:05 A surprising comparison introduces fast follow investing10:20 Why fast follow may complement buy-and-hold11:09 The risk of needing savings after a market crash15:00 Loss asymmetry: why recovery takes more than the drop17:16 Why investment losses can feel especially painful20:00 Brian’s 2020 sell-off and the cost of missing the rebound23:46 Investor education and when portfolio strategy should change25:14 Cash, bonds, and other approaches to limiting downside28:36 Why the hosts leave fast follow mechanics for part two This episode is for educational purposes only and is not individual investment advice. Backtested results are hypothetical and do not guarantee future performance. 🎧 Order your copy of Time Freedom today!

  2. Oct 20

    Investing Your Way to Time Freedom (Case Study)

    ➡️ Try the TIME FREEDOM CALCULATOR: https://timefreedomcalculator.com➡️ Buy TIME FREEDOM, the book: https://timefreedom.life/book➡️ Read the FAST FOLLOW INVESTING bonus chapter: https://timefreedom.life/fastfollow In this episode... Izzy and her husband are a no-kids couple from Atlanta who earn a combined $250,000 a year, live on $120,000, and save the rest. They’ve been saving and investing since college and already have $1.8 million. Their goal is time freedom by 50, without starting a business and without counting on flexible income later. Brian and Kirby run the numbers in the calculator, then crash the portfolio by 35% (hypothetically) the moment Izzy retires, to see whether the plan still holds. They connect Izzy's plan to one key spending principle from Chapter 7 of the book, “save more earlier to invest well later,” and show what happens when a better investment return lets Izzy save far less and enjoy her forties. For a detailed walkthrough of this case study, watch the video “Saver and Investor, Not Entrepreneur (Izzy)” at https://timefreedom.life/help. Top 5 Takeaways: You don’t have to become an entrepreneur. Flexible work opens up more options, but a good saver and investor can reach time freedom on savings alone. Izzy never starts a business and never needs income after 50.Your portfolio eventually out-earns your savings. Early on, how much you save matters most. Later, your return takes over. On Izzy’s $1.8 million, a good year earns almost twice what she saves.Stress-test the worst case. Markets drop more often than it feels like when things are going up, so plan for it. Even with a 35% crash the day Izzy retires, her money still lasts to 100.Your return is your biggest lever. A few extra percentage points can replace years of heavy saving. At a 10% return, Izzy would only need to save $15,000 a year instead of $100,000.Money you don’t have to save is money you can enjoy. You don’t have to sacrifice every year of your forties to retire early. The calculator shows which trade-offs still work: travel more now, work a little longer, or both.Chapters:  00:00 Introduction to the episode and guest02:00 Exploring the concept of Alameda and local insights05:02 Update on book writing and mailing strategies09:06 Case study introduction: Izzy the saver and investor13:10 Modeling market crashes and resilience16:57 Adjusting lifestyle and savings for early retirement22:00 The power of fast follow investing and higher returns23:58 Scenario analysis: Market drops and long-term wealth25:04 Upcoming deep dive into fast follow investing25:57 Closing remarks and call to action  🎧 Order your copy of Time Freedom today!

  3. Oct 13

    Corporate to Entrepreneur, the No-Hustle Way

    ➡️ Try the TIME FREEDOM CALCULATOR: https://timefreedomcalculator.com➡️ Buy TIME FREEDOM, the Book: https://timefreedom.life/book In this episode... Annika is a corporate sustainability director at 42, and she has bigger dreams. Her husband Nick has spent his whole career quietly saving and investing, and together they’ve built up $500,000. Their goal is time freedom by 45, with their daughter Maya’s college still to pay for.  On today’s podcast, Brian and Kirby walk through the case example from Chapter 12 of the book: a first year spent getting ready while the paychecks keep coming, a second year launching the business, and a third year earning the income that makes the plan work. They also cover the five numbers that matter most and how to stress-test your own plan so a bad year doesn’t catch you off guard. For a detailed walkthrough of this case study, watch the video "Employee to Entrepreneur (Book Example, Anika)" at https://timefreedom.life/help. Top 5 Takeaways: Director level is often a moment to decide. Once you’re leading and doing the work at the same time, you either commit to the climb toward VP or start planning your way out. It’s when “what am I doing?” turns into “why am I doing this?”Sell what you’ve already proven. Annika isn’t inventing anything new. She’s doing the work she did as a director, but as an independent consultant. When people already know they need what you offer, most of the hard parts of selling go away.Your network is your first client list. Spend a year reconnecting with 50 people, not to pitch them but to get back in touch. People who already know and trust you are halfway through the sales cycle before you ask.Two partners, two strengths. Annika brings the entrepreneurial drive, and Nick brings the saving and investing. Nick keeps his job and the health insurance while the business finds its footing, then joins her once it’s steady.Run the “what ifs” before they happen. The calculator lets you test what happens if the business only brings in $60K, if Maya skips college, or if you sell the house early. Seeing that the plan still holds gives you the confidence to start.Chapters:  00:00 Introduction to the case study and main concepts02:09 The scenario of Annika and Nick's transition04:03 Setting goals and planning for time freedom08:03 Using the time freedom calculator for scenario modeling12:04 Building proven services and activating your network16:00 The 3-year transition framework and key drivers19:52 Adjusting plans and confidence in your transition23:03 Resources and next steps for planning your transition25:59 Upcoming case studies and community resources  🎧 Order your copy of Time Freedom today!

  4. Oct 6

    Andy Hill Wrote the (Other) Book on Owning Your Time

    ➡️ Buy TIME FREEDOM, the Book: https://timefreedom.life/book➡️ Listen to Marriage, Kids and Money: https://pod.link/1175746628 In this episode... Andy explains FIRE and Coast FI by comparing two extremes: traditional retirement at 65 and saving half your income to retire at 40. He shares how the second extreme strained his marriage, and why he and his wife settled on a middle path. He walks through the numbers behind it: The couple went from $50,000 in debt to a $1 million net worth in ten years, paid off a home mortgage early, and then both moved to part-time work. Andy also shares his four levels for getting more time freedom without becoming an entrepreneur, and how he protects a three-day work week. The conversation covers karaoke, right and left socks, and why you don't need to become a YouTuber to find time freedom. Top 5 Takeaways: Coast FI and time freedom are similar. The FIRE community started with two extremes, working until 65 or saving half your income to quit at 40. Coast FI evolved toward the middle: work you like, on your terms, with time to live a fuller life now.Andy's story is the Time Freedom Formula in action. Time freedom happens when your investment income plus your flexible work covers your expenses, and Andy is using all three levers. He has no mortgage and no debt, his investments grew from $550K to $1M without new contributions, and he runs a business he works three days a week. You don't need all three at full strength, but the more levers you pull, the faster you get there.Lowering expenses is the fastest lever. Paying off a 3% mortgage looks wrong on paper, but it worked for Andy. With no mortgage, Andy's family could live on about $100,000 instead of $180,000, and both spouses could go part-time.Flexible work doesn't require becoming a YouTuber. Andy's four levels are a roadmap to the flexible work lever. Start by asking your employer for four days at 80% pay. Then look at a competitor who will offer that, or take your skills out as a consultant or freelancer. Starting something from scratch is the last step, not the first.Time freedom isn't about quitting work, it's about choosing it. Andy and Brian both keep working, because meaningful work gives you purpose and keeps your skills sharp as a safety valve if the stock market drops. The goal isn't sitting on your butt. It's having the space to decide what a great life looks like for you.Chapters Chapters 00:00 Introduction to Andy Hill and his journey to time freedom01:00 Andy shares a fun fact about his karaoke hobby03:00 Discussion of the concept of FIRE and Coast FIRE08:06 How Coast FIRE is a middle ground between traditional FIRE and aggressive saving11:51 Andy’s personal story of transitioning from corporate job to Coast FIRE16:03 Different levels of work reduction and lifestyle design19:57 Managing distractions and creating buffer in work and life22:59 The importance of financial and emotional buffers27:03 The role of purpose and ongoing work in a fulfilling life36:00 Final thoughts on balancing work, purpose, and time freedom  🎧 Order your copy of Time Freedom today!

  5. Sep 29

    So... How's the Book Doing?

    ➡️ Buy TIME FREEDOM, the Book: https://timefreedom.life/book➡️ Join the COMMUNITY: https://timefreedom.life/community/ In this episode... Recorded partly live from the launch reading in Alameda, Brian and Kirby break down the strategy behind the book's first week.One week after launch, Time Freedom had 107 Amazon reviews and 92 on Goodreads, and it didn't take a Good Morning America appearance to get there. On today's podcast, Brian and Kirby celebrate the launch and share the inside story of what it actually takes to get a book into readers' hands. It isn't glamorous, but it works. Brian also reads the review that captured exactly what he hoped the book would do, and explains why he thinks everyone should write a book, if only to feel how many people will show up for you. Top 5 Takeaways: Aim for 10,000 readers, not 10,000 sales. The standard advice is to sell 10,000 copies. What really matters is 10,000 ideal readers who finish the book, because they're the ones who tell others and keep it spreading on its own.A launch is won one message at a time. Bulk orders turn supporters into distributors. Supporters bought 25-book bundles and kept what they wanted. The rest went to indie bookstores in every state and to Small Business Development Centers, putting the book on shelves where the right reader might find it.Put your email in your book. Reader emails and reviews show you the real impact. Many readers are realizing they already have time freedom and don't need to feel bad about not earning more.Ask, and people will show up. Brian joined three writing communities over two and a half years, and more than 100 early readers gave feedback. His advice: write a book and tell people about it, because they'll come out of the woodwork to support you.Chapters:  00:20 Live from the bookstore in Alameda03:57 Celebrating launch week and the 10,000-reader goal07:06 Reader reviews and two and a half years of writing11:12 What a book is really worth15:31 Indie bookstores, bulk orders, and SBDCs19:14 Climbing the Amazon rankings22:23 What's next and wrap-up 🎧 Order your copy of Time Freedom today!

  6. Sep 22

    Where to Keep Cash So You Can Pounce

    Three days after a place on Lake Seventeen unexpectedly went up for sale, Brian and Claire had their offer accepted, because the cash to move on it was already sitting ready. On today's podcast, Brian and Kirby dig into a topic that sounds boring on paper: where to store your cash. Cash savings is a key component of the Time Freedom Portfolio, and in this episode we talk tactics: exactly where to put it so it's usable the moment an opportunity (or emergency) shows up. ➡️ Get the guide to Good Cash Savings Accounts: https://timefreedom.life/resources ➡️ Buy TIME FREEDOM, the Book: https://timefreedom.life/book In this episode... Brian revisits the case for holding more cash than most financial advice recommends, then walks through nine specific places to put it, grouped into four categories: bank accounts, brokerage cash and money market accounts, treasuries, and CDs. He and Kirby also discuss why convenience matters more than chasing the highest interest rate, and a brokerage sweep account trap to watch out for. Top 5 Takeaways: Cash reserves are optionality, not idle money. Brian and Claire bought their new cabin on Lake Seventeen within three days of it hitting the market, only possible because the cash was already sitting there, ready to move.Hold more cash than typical advice suggests. Brian recommends 10-30% of your portfolio, or six months to two years of expenses, and says you'll know it's right when you feel equally uncomfortable about having too much and too little.Convenience beats interest rate. A 0.2% difference in APY matters far less than how fast you can actually get the money when you need it.There are nine places to hold cash across four categories. High-yield savings accounts, credit unions, brokerage money market accounts, treasury ETFs like SGOV and BIL, and CDs all serve different tradeoffs between access and yield.Watch your brokerage's default cash sweep. Charles Schwab's default sweep account pays a fraction of what's available elsewhere in the same brokerage. You have to manually move it to a higher-yield option, and that gap is exactly how they profit.Chapters:  Chapters 00:00 Introduction to cash management and opportunities02:48 Recent cabin purchase on Lake Seventeen and financial freedom08:03 Episode overview and upcoming book launch discussion11:02 How much cash to hold for financial stability12:20 Interest rates and where to put your cash15:13 Categories of cash accounts and their benefits20:44 Inside brokerage accounts and cash storage options22:44 Treasuries and T-bills for short-term savings24:53 Using CDs and ladder strategies for longer-term savings27:56 Key takeaways: most convenient and safe cash options  Ready to see how close you are to time freedom? Take the free assessment at timefreedom.life/score, and if you want to build your plan alongside others doing the same thing, check out the Time Freedom Community at timefreedom.life/community. 🎧 Order your copy of Time Freedom today!

  7. Sep 15

    Book launch day! It's time to meet Claire

    Today on the podcast, Brian sits down with his wife, Claire, for a special episode on the day Time Freedom was officially released. They talk about how Claire shaped the book, from strategically timing her first read to the origin of the now-famous "Claire's Official Disclaimer," and the real story behind the emergency room scene that opens Chapter One. ➡️ Buy your copy of Time Freedom here. In this episode... Brian and Claire talk through how she got involved in the writing process, why she waited until three-quarters of the way through to read a word of it, and how a joke about disavowing his use of "we" became one of the book's most-quoted lines. Brian reads aloud an excerpt from the opening of Chapter One, the 1999 emergency room scene. The two talk candidly about what that day actually felt like from her side, and how it shaped her belief that life is "equal parts hard work and luck." They close out with the story behind one of the book's funniest asides. Chapters: 00:00 Introduction and special episode context 02:00 Strategic involvement in editing and feedback 04:58 Claire's official disclaimer and perspective 07:13 The life story that inspired the book 08:11 Recollections of the hospital experience 09:24 The significance of the lung transplant event 11:15 Living with the awareness of life's brevity 13:28 Reflections on creativity and life ambitions 14:06 Humor and storytelling in the book 16:07 Closing thoughts and gratitude 🎧 Order your copy of Time Freedom today!

  8. Sep 8

    But What About Health Insurance?

    Today on the podcast, Brian and Kirby open with a hard number: 23 million Americans are stuck in jobs they want to leave, not for the paycheck, but for the health insurance. From there, Brian walks through his own decade-long path to coverage: COBRA, a startup's small business plan, and eventually the Affordable Care Act. Then, he breaks down fourteen options you should consider to get the health coverage you need. Health insurance should not be the reason you're stuck in a job you hate. ➡️ Get the Healthcare Options Guide: http://timefreedom.life/resources  ➡️ Buy Time Freedom, the book: https://amzn.to/4qP14rE In this episode... Brian opens with a Gallup stat on how many Americans stay in jobs purely for the health coverage, then shares his own healthcare journey from before the Affordable Care Act through starting his business in 2017. He and Kirby break down the difference between "can I get coverage" and "can I afford it," then Brian runs through fourteen options grouped into five categories: plans most people can get, bridge and transition options, group and association routes, lower-cost alternative models, and special situations like Medicaid and international care. Top 5 Takeaways: Healthcare, not money, is what traps too many people. A recent Gallup poll found 23 million Americans stay in jobs they want to leave purely for the health coverage, not the paycheck.Coverage and cost are two separate problems. Solve whether you can get covered first. Affordability is a budgeting question once you know coverage exists.Brian went nearly a decade without a "normal" plan. COBRA, California's extended Cal-COBRA, a small business plan tied to his software startup, and eventually an ACA small business plan all covered him at different points after he left corporate in 2017.HSAs work like a second retirement account. Unlike an FSA, unused HSA funds roll over and grow tax-free. Kirby had two years of deductibles saved before having kids just by treating it that way.There are more options than most people realize. From Costco-style group plans to healthcare sharing ministries to state programs for genetic conditions, Brian counts fourteen different paths to getting health insurance.Chapters: Chapters 00:00 Healthcare Challenges for Self-Employed01:50 Statistics on Healthcare and Job Satisfaction03:52 Personal Stories of Healthcare Decisions08:04 Legislative Impact on Healthcare Options11:50 Different Healthcare Coverage Strategies20:00 Special Situations and Unique Healthcare Solutions34:08 Resources and Next Steps for Healthcare Planning If you've been meaning to grab a copy of Brian's book Time Freedom, now's the time! Order now and you're book will be delivered in just one week! 🎧 Order your copy of Time Freedom today!

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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
    50
  • Rating
    Clean
  • Copyright
    © 2025
  • Show Website
    The Time Freedom Podcast

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