The Time Freedom Podcast

By Brian Herriot, Kirby DenisonBusiness Entrepreneurship Investing

The Time Freedom Podcast episodes

October 06Andy 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 freedom
01:00 Andy shares a fun fact about his karaoke hobby
03:00 Discussion of the concept of FIRE and Coast FIRE
08:06 How Coast FIRE is a middle ground between traditional FIRE and aggressive saving
11:51 Andy’s personal story of transitioning from corporate job to Coast FIRE
16:03 Different levels of work reduction and lifestyle design
19:57 Managing distractions and creating buffer in work and life
22:59 The importance of financial and emotional buffers
27:03 The role of purpose and ongoing work in a fulfilling life
36:00 Final thoughts on balancing work, purpose, and time freedom
🎧 Order your copy of Time Freedom today!
42 min
September 29So... 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 Alameda
03:57 Celebrating launch week and the 10,000-reader goal
07:06 Reader reviews and two and a half years of writing
11:12 What a book is really worth
15:31 Indie bookstores, bulk orders, and SBDCs
19:14 Climbing the Amazon rankings
22:23 What's next and wrap-up
🎧 Order your copy of Time Freedom today!
26 min
September 22Where 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 opportunities
02:48 Recent cabin purchase on Lake Seventeen and financial freedom
08:03 Episode overview and upcoming book launch discussion
11:02 How much cash to hold for financial stability
12:20 Interest rates and where to put your cash
15:13 Categories of cash accounts and their benefits
20:44 Inside brokerage accounts and cash storage options
22:44 Treasuries and T-bills for short-term savings
24:53 Using CDs and ladder strategies for longer-term savings
27:56 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!
30 min
September 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!
18 min
September 08But 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-Employed
01:50 Statistics on Healthcare and Job Satisfaction
03:52 Personal Stories of Healthcare Decisions
08:04 Legislative Impact on Healthcare Options
11:50 Different Healthcare Coverage Strategies
20:00 Special Situations and Unique Healthcare Solutions
34:08 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!
37 min
September 01Your Money's Not Locked Up
Today on the podcast, Brian and Kirby kick off Season 3 by tackling money that's technically yours but functionally out of reach, because it's locked in a 401k, a business, or your home equity. First, the story of a client who had six figures saved but still felt stuck and needing permission as much as a plan to access it. And then, some tactics for how to handle this "good" problem to have. This episode is for those of you who have built some wealth but feel like you can't spend a dollar of it.
➡️ Get the Early Withdrawal Strategies Guide: http://timefreedom.life/resources
➡️ Buy the Time Freedom Book: https://amzn.to/4qP14rE
In this episode... Brian and Kirby dig into how to access money that's trapped in the places you've built wealth (your business, your home, and especially your retirement accounts) before you're 59½. Brian walks through the mindset behind early withdrawals, then breaks down four ways to actually pull money out of an IRA or 401k, from tax-free Roth withdrawals to just paying the 10% penalty and moving on. They close out with how much you can safely withdraw once you do, from Bill Bengen's original 4% rule to more flexible modern approaches.
Top 5 Takeaways:
Sometimes the penalty is worth paying. Brian's client Shelby paid the 10% to leave her career and buy land in rural Colorado. Two years later, she's running the business she couldn't have started otherwise.

Net worth isn't cash on hand. You can have real wealth and almost nothing you can actually spend — money trapped in a retirement account, a business, or your home equity doesn't help you take the leap until you get it flowing.

There are four ways to access retirement money before 59½. Roth contribution withdrawals, a Roth conversion plus the five-year rule, SEPP/72(t) payments, and a straight withdrawal with the penalty — each trades speed for cost differently.

The 4% rule is a starting point, not gospel. Bill Bengen's original 1994 research holds up, but modern versions run closer to 3.5–4.5%, and methods like Vanguard's floor-and-ceiling approach flex your withdrawal with the market instead of locking it in.

Flexible income is the real safety net. The more you can dial your work up or down, the less you have to lean on a fixed withdrawal rate in a down market year.
Chapters
00:00 Introduction to the episode and main themes
02:14 Kirby shares about completing 75 Hard and its lessons
03:16 Overview of season three plans and focus on living with time freedom
08:24 Introduction to early withdrawal strategies and mindset
16:10 Accessing retirement funds early: mindset and options
20:07 Different methods to withdraw from retirement accounts
30:31 The 4% rule and safe withdrawal rates
35:07 Flexibility and strategies for sustainable withdrawals
36:17 Upcoming topics and closing remarks

🎧 Order your copy of Time Freedom today!
38 min
June 02Building 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.

🎧 Order your copy of Time Freedom today!
42 min
May 26Tim 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.
🎧 Order your copy of Time Freedom today!
56 min
May 19Dr. 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.
🎧 Order your copy of Time Freedom today!
38 min
May 12Lee 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.
🎧 Order your copy of Time Freedom today!
45 min

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