The Freedom Founders Podcast

Dr. David Phelps
  • 4.2 (5)
  • Entrepreneurship

Build Wealth You Control. Design A Life You Choose. For Founders aiming higher and wanting to maximize time for enjoyment and impact. Burnt out? Needing direction? If you’ve climbed “the mountain” and still feeling like you’re missing something… This podcast shows how other owners are winning back their time, increasing influence and creating cash flow for maximum impact.

  1. 3d ago

    The Passive Investing Trap: What You Can't Afford To Outsource - Ep39 Jeff Cichocki

    The Passive Investing Trap: What You Can’t Afford to Outsource – Ep39 Jeff Cichocki Nobody pitches an investment by telling you how you could lose your money. That part usually comes in a thick stack of documents you’re tempted to sign without reading. Jeff Cichocki wants you to read them. Then bring him 10 questions. Until you do, this fund manager won’t take your money. Dr. David Phelps invited Jeff onto the podcast after reading a post that stopped him. Here was someone in the business willing to talk openly about its problems, including whether he wanted to keep doing it. They get into the trouble with selling “passive” income, deals built on cheap debt, and the costly mistake of assuming a likable person knows how to manage your money. Jeff also talks about an acquisition that didn’t perform the way he expected. The agreement allowed him to keep collecting his share. He cut his compensation anyway. He couldn’t stomach doing well while his investors went without. Toward the end, Jeff talks about losing his wife. Two years before she died, he had started changing the business so he could leave his desk when she wanted to go to lunch. No rearranging the day. Just go. That’s a good thing to remember when another deal comes along and you catch yourself thinking, “A little more, and then I’ll have enough.” EPISODE LINKS: • Connect with Jeff Cichocki: JeffCichocki.me • Get your free copy of The Exit Optional Playbook: ExitOptional.com • Explore the Freedom Founders Podcast: FreedomFounders.com/podcast EPISODE HIGHLIGHTS: 00:00 – Passive Investor Responsibility 02:02 – Getting Started in Real Estate 07:49 – Transitioning to Private Lending 13:15 – Market Realities and Syndication Risks 16:58 – Defining Passive vs. “Done For You” Investing 20:23 – Fund Manager Accountability and Transparency 28:46 – The Importance of Slowing Down and Vetting Sponsors 37:12 – Designing a Business That Serves Your Life

    The Passive Investing Trap: What You Can't Afford To Outsource - Ep39 Jeff Cichocki

  2. Oct 26

    You Built the Wealth. Where’s the Income? – Ep38 Dr. Mart McClellan

    Your net worth has grown. Your retirement accounts look healthy. But what happens when your paycheck stops? In this episode, Dr. David Phelps reconnects with Dr. Mart McClellan, a former practicing orthodontist and co-founder of Macro Wealth, to explore the gap between accumulating wealth and creating income you can live on. Mart explains why accumulation, distribution, and preservation belong in the same conversation from the beginning. They discuss the tradeoffs behind tax-deferred retirement accounts, the importance of keeping capital accessible, and why feeling behind can lead successful professionals to make financial decisions they later regret. They also explore how couples can find common ground when their definitions of financial security differ—and why financial decisions deserve the same evidence-based thinking we expect in clinical practice. For owners considering their next chapter, the question goes beyond how much you’ve saved: How will that money support your life when you choose to work less? In This Episode • The gap between growing your net worth and replacing your active income. • How inflation can distort your sense of financial progress. • Why accumulation, distribution, and preservation need to work together. • The tradeoffs between tax deferral, access, and control. • Why the urge to “catch up” can lead to costly decisions. • How spouses can align around risk and financial security. • Mart’s approach to testing financial decisions before making them. Episode Links Connect with Dr. Mart McClellan: mart@mcwealth.com Request a copy of Your Retirement Smile by emailing Mart. Get Dr. David Phelps’s free Exit Optional Playbook: https://exitoptional.com Episode Highlights 00:00 – Turning Wealth Into Income—and Keeping Your Options Open 00:36 – Seven Years Later: What’s Changed Since Our Last Conversation 02:04 – Inflation, Interest Rates, and the Growing National Debt 04:48 – The Stealth Tax: What Your Account Balance Doesn’t Tell You 07:16 – Accumulation, Distribution, and Preservation: Planning for All Three 09:30 – “I Thought I’d Be Further Along”: Financial Decisions Across Career Stages 11:47 – Accumulation vs. Acceleration: Putting Your Capital to Work 15:18 – Building Flexibility Outside Your Retirement Accounts 20:13 – Tax Deferral, Access, and Control: Understanding the Tradeoffs 23:36 – When Spouses Define Financial Security Differently 28:02 – Why Mart Moved From Clinical Orthodontics Into Financial Planning 31:14 – Connect With Dr. Mart McClellan and Request Your Retirement Smile 33:09 – Before You Sell: Are You Ready for What Comes Next?

    You Built the Wealth. Where’s the Income? – Ep38 Dr. Mart McClellan

  3. Oct 19

    Stop Waiting for Someday: Build the Life You Want Now – Ep37 Trevor Mauch

    What if the life you've been working so hard to create is already within reach—but you're too busy running your business to start living it? Many entrepreneurs reach a point where they're making more money than ever, yet feel more overwhelmed, frustrated, and disconnected from the life they originally wanted. In this episode, Dr. David Phelps sits down with Trevor Mauch, entrepreneur and founder of Carrot, to explore why successful business owners get stuck—and how to break free without abandoning everything they've built. Trevor shares his Four Paths framework, explaining how success can quietly turn into complacency, frustration, and eventually burnout. He also walks through the personal systems he uses to stay intentional about his business, health, family, and future. This conversation challenges a common assumption: that the answer to feeling stuck is simply working harder. Conversation Highlights: 02:05 – What Did You Hire Your Business to Do for You? 04:17 – The Four Paths: Navigating Business and Life 05:40 – The Six Fs: Measuring What Really Matters 07:33 – Staying Above the Line: Success and Transformation 08:10 – The Danger of Default Mode and Drifting 11:53 – Getting Unstuck: Reconnecting with Your Vision 14:47 – Why Indecision Keeps Entrepreneurs Trapped 17:59 – When Success Leads to Burnout 20:24 – Buying Back Your Time and Energy 22:15 – The Entrepreneur Freedom Formula 24:51 – Plan Your Life First: The Pre-Stacked Year 28:46 – Making Decisions Before It's Too Late 30:12 – The Real Measure of Success: How You Spend Your Time The Bigger Question Are you still building the life you set out to create—or have you simply gotten better at maintaining the business? Trevor's message is that you don't have to wait for a financial milestone, an exit, or a crisis to begin making changes. Sometimes the most important step is deciding what matters now—and giving it a place on your calendar before everything else fills it.

    Stop Waiting for Someday: Build the Life You Want Now – Ep37 Trevor Mauch

  4. Oct 12

    From Outrage to Agency: Using Your Freedom to Change the World – Ep36 Rick Green

    What good is the freedom we've spent a lifetime building if we don't use it to make a difference? In this episode, Dr. David Phelps sits down with Rick Green, founder of Patriot Academy and former Texas state legislator, to explore what it means to use our freedom, experience, and influence to make a lasting difference. Rick shares how his father's encouragement shaped his life, why he shifted his focus from politics to educating the next generation, and what he's learned from more than 25 years of developing young leaders. They also discuss what older generations misunderstand about young people, why we've lost the ability to disagree without hostility, and how to move beyond frustration and outrage toward meaningful action. For business owners considering their next chapter, Rick offers a practical challenge: You don't need to run for office, start an organization, or write a large check to make a difference. There are meaningful ways to invest your time, resources, and experience right where you are. In This Episode How Rick's father helped shape his confidence, character, and sense of purpose.Why Rick believes developing the next generation is more important than winning elections.What young people really want from leaders, parents, and mentors.How to disagree without hostility—and why curiosity matters more than winning an argument.Why moving from outrage to agency starts with taking responsibility for what we can influence.Rick's practical 2-2-2 framework for getting involved and making a difference.Episode Links Patriot Academy: https://patriotacademy.com The Exit Optional Playbook: https://exitoptional.com Episode Highlights 02:21 – Finding His Calling Beyond Politics: The conversation with his father that changed Rick's direction03:30 – The Power of Family Influence: How his parents shaped his confidence, entrepreneurial spirit, and teaching style04:28 – A Wake-Up Call About Freedom: Why Rick became passionate about constitutional education05:28 – Building Patriot Academy: Developing the next generation of civic leaders06:42 – What We're Getting Wrong About Young People: Their desire for authenticity, purpose, and meaningful contribution08:33 – From Outrage to Civil Discourse: Why listening and humility matter more than winning arguments11:28 – Putting Freedom Into Action: Rick's practical 2-2-2 framework for making a difference

    From Outrage to Agency: Using Your Freedom to Change the World – Ep36 Rick Green

  5. Oct 5

    The Letter His Father Left: A Legacy That Outlived a Tragedy – Ep35 Blake Brewer

    His father’s voice was still there. In a letter. At 19, Blake Brewer lost his father in a snorkeling accident during a family vacation in Hawaii. Hours later, his mother found a letter in his father’s briefcase—one he had intended to give Blake on that trip. His father was gone, but his words remained. More than two decades later, Blake still returns to that letter. In this episode, I sit down with Blake, founder of Legacy Letter, to hear how that experience became a mission to help one million people write a letter to their families. We spend years building businesses, providing for our children, and planning what we’ll leave behind. But how much thought do we give to what we’re leaving in them? Do they know how deeply we love them, what we admire about them, and why we believe in their future? Blake shares a practical framework for putting those things into words, including a section many parents would rather skip: the apology. We talk about why good intentions don’t always translate into close relationships, how pride can keep us from saying what needs to be said, and why “I’m doing it for my family” deserves an honest look. We also discuss when to give the letter, why your child’s initial reaction may tell you very little about its lasting value, and how this personal exercise has helped business teams connect. For anyone who has been meaning to say more to the people they love, this conversation offers a place to start—and a reason to follow through. EPISODE LINKS: Learn more about Blake Brewer and Legacy Letter: LegacyLetter.com Learn more about Freedom Founders: FreedomFounders.com Request your free copy of The Exit-Optional Playbook: ExitOptional.com HIGHLIGHTS: 02:59 – The family vacation that changed Blake’s life 06:46 – The letter his father left behind 11:56 – Why “my kids know I love them” can leave room for doubt 14:20 – What to include in a legacy letter—and why apology matters 17:05 – Give the letter now: Why you don’t need to wait 23:03 – A father’s letter that brought his daughter home 24:20 – When “I’m doing it for my family” deserves a closer look 27:16 – How legacy letters helped business teams connect 28:34 – Defining success by the family relationships you’re building 30:23 – Words your children can hear from you today

    The Letter His Father Left: A Legacy That Outlived a Tragedy – Ep35 Blake Brewer

  6. Sep 28

    The Retirement Tax Trap: When Tax Deferral Starts Working Against You – Ep34 Nate Hare

    You’ve probably spent years being told that putting money into a 401(k), IRA, or other retirement account is the responsible thing to do. Make the contribution. Take the deduction. Let it grow. But there is a part most busy doctors rarely think about: Eventually, the IRS wants its money back. If you build a large pre-tax retirement account without a plan for how that money will come out, what looked like a tax strategy may turn out to be a tax delay. That matters because once required minimum distributions begin, you lose some control. The government determines that money must come out, and those distributions can increase your taxable income whether you need the money or not. In this episode, I sit down with Nate Hare to unpack what that means in practical terms. We discuss: Why tax deferral and tax elimination are very differentWhat required minimum distributions could mean for your future incomeHow Roth conversions can create more flexibility laterWhy the years after you reduce active income may be a critical planning windowHow self-directed retirement accounts can expand your investment optionsWhy certain investments may belong inside retirement accounts while others may notHow large pre-tax accounts can create an unexpected tax burden for your heirsYou do not need to become a retirement-account expert. But you do need to understand the basic tradeoff. The decisions you make while you are earning at your peak can either preserve flexibility later—or quietly reduce it. That is what this episode is really about. Not tax tricks. Optionality. The ability to decide when income appears, when taxes are paid, and how much control you retain over the wealth you spent decades building. EPISODE LINKS: Directed IRA: https://directedira.com Learn more about Nate Hare and self-directed retirement accounts. Directed IRA Appointments: https://directedira.com/appointment/ Connect with Nate and the Directed IRA team. Freedom Founders: https://www.freedomfounders.com Learn more about becoming financially independent and exit-optional. HIGHLIGHTS: 00:00 – Why retirement accounts deserve more attention than most business owners give them 01:34 – What you may be allowed to own beyond stocks and mutual funds 06:58 – Why self-directed accounts appeal to entrepreneurial investors 08:52 – The difference between tax-deferred and tax-free retirement income 11:00 – Why Roth conversions may matter more than the deduction you received years ago 24:00 – The danger of a large pre-tax retirement account with no exit strategy 26:00 – What required minimum distributions actually mean for your future income 28:00 – How your retirement account can create a tax problem for your children 29:16 – The planning window between reducing active income and required distributions 33:47 – Why you should diversify your tax exposure, not just your investments 40:43 – How high-income earners may still be able to get money into Roth accounts

    The Retirement Tax Trap: When Tax Deferral Starts Working Against You – Ep34 Nate Hare

  7. Sep 21

    Investing When Risk Is Rising: Rates, Leverage, and Protecting Your Capital - Ep33 Anna Kelley

    The investments that performed well during the era of cheap money may carry far more risk today—even when the projected returns still look familiar. In this episode, I sit down with longtime real estate investor and former private banker Anna Kelley to examine what higher interest rates, a weakening labor market, and the growing wall of maturing debt could mean for everyday investors. Anna explains why the Federal Reserve is caught between persistent inflation and recessionary pressure—and why waiting for rates to simply “go back down” may not be a sound investment strategy. We also look closely at multifamily real estate, where rising rates have erased 40% or more of the value of some properties. Even experienced operators are struggling to refinance debt, preserve investor capital, and hold assets together. The problem is not always poor execution. Sometimes the economic assumptions that made a deal work have fundamentally changed. Most importantly, Anna translates the economic headlines into decisions investors can actually make. We discuss how to determine whether a prospective return adequately compensates you for the risk, why liquidity and diversification deserve renewed attention, and when protecting capital matters more than pursuing another double-digit return. This conversation ultimately goes beyond markets. Anna shares how financial margin gave her the ability to step away from work when her health and family needed her. Because the real purpose of liquidity is not to win an argument about portfolio allocation. It is to preserve your ability to respond when life refuses to follow the plan. EPISODE LINKS: Learn more about Anna Kelley: https://annakelleyinvesting.com/ Learn more about Freedom Founders: http://FreedomFounders.com HIGHLIGHTS: 00:00 – Introduction 01:58 – The Fed’s conflict between inflation and a weakening economy 04:39 – What the employment headlines may be missing 05:53 – Why Anna sees a stagflationary environment 10:36 – Growth, income, or preservation: What is your priority? 14:37 – How to tell whether a return justifies the risk 19:26 – Why multifamily worked so well during the low-rate era 27:00 – How higher rates erased 40–50% of some property values 28:44 – The refinancing wall facing real estate operators 31:09 – The liquidity signal Anna is watching now 34:39 – Why maturing debt through 2029 could create a larger crisis 39:35 – What individual investors can do with this information 42:16 – How debt and the Great Financial Crisis cost Anna a decade 44:06 – Learning to sit patiently on cash 45:02 – Building multiple income streams and an all-weather portfolio 45:45 – When building wealth leaves no room for life 48:02 – Why bigger is not always better

    Investing When Risk Is Rising: Rates, Leverage, and Protecting Your Capital - Ep33 Anna Kelley

  8. Sep 14

    How to Build Personal Sovereignty in a Changing World - Ep32 Lee Milteer

    Personal sovereignty starts with taking responsibility for your own life. David Phelps reconnects with entrepreneur, author, speaker, and business and mindset strategist Lee Milteer to discuss resilience, independent thinking, intentional habits, preparedness, entrepreneurship, and why protecting your attention and surrounding yourself with the right people matter in a rapidly changing world. EPISODE LINKS: Learn more about Lee Milteer: https://milteer.com/ Free Five Types of Energy video series: https://fivetypesofenergy.com/ Learn more about Freedom Founders: http://FreedomFounders.com HIGHLIGHTS: 00:00 – Intro 14:08 – Building a Fearless Mindset 18:11 – Lessons From Dan Kennedy 27:38 – Stop Following the Crowd 33:05 – Your Habits Create Your Life 45:31 – Protect Your Attention 50:23 – Staying Relevant in the Age of AI 52:57 – Why Masterminds Matter

    How to Build Personal Sovereignty in a Changing World - Ep32 Lee Milteer
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4.2
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Build Wealth You Control. Design A Life You Choose. For Founders aiming higher and wanting to maximize time for enjoyment and impact. Burnt out? Needing direction? If you’ve climbed “the mountain” and still feeling like you’re missing something… This podcast shows how other owners are winning back their time, increasing influence and creating cash flow for maximum impact.

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