Truly Passive Income

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161

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Oct 2026

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Are you ready to build true wealth and financial independence for your family and live life exactly as you've always wanted? Each week, tune in to Truly Passive Income, as Neil Henderson and Clint Harris interview guests who are experts in using passive investing to achieve financial and location independence, design more meaningful and intentional lives, and make a positive impact on the world. If you're seeking freedom from the grind of trading your time for money and want to prioritize what truly matters in life, this podcast is for you.

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October 26, 202642 min

Why Cash Flow Alone Won't Save Your Real Estate Portfolio

Chris Naugle had a 36-unit rental portfolio bought at about $16,000 a door, and he still had to sell all of it in 2014. In his words: "I had cash flow, but I had no liquidity." Chris is a former professional snowboarder who became a Wall Street financial advisor, a real estate investor, and the founder of The Money School and the Private Money Club. He came close to bankruptcy twice. In 2008 a hard money loan on a strip mall development went bad when the Great Recession hit mid-construction, and a single tenant who called out of the blue got the building to the occupancy his bank required for takeout financing. In 2014 he learned that financing rentals in his personal name for a lower rate had pushed his debt-to-income ratio past the bank's limit. The bank declined his next deal, froze the line of credit he used for renovations, and he was forced into a fire sale of the entire portfolio. Those lessons shaped what he teaches now. Chris explains why he says that in real estate you never lose if you can get to the end, but most people run out of time first. He describes how a private lender introduced him to privatized banking and the infinite banking concept, how he built Private Money Club as a free dating site for money with more than 10,000 members, and why he believes cost is only an issue in the absence of value. He also makes the case for using AI to handle the busy work so you can spend more time on human relationships, and leaves listeners with a 30-day challenge built around Earl Nightingale's The Strangest Secret. Chapters [0:00] I had cash flow, but I had no liquidity [1:20] A clothing company at 16, a board shop at 17 [3:42] The dot-com recession sends him to Wall Street [9:46] His first flip and a strip mall bet [11:10] Hard money lenders and the Great Recession [12:38] One tenant saves him from bankruptcy [14:49] Buying rentals at $16,000 a door [16:42] Hitting the debt-to-income wall [17:39] A frozen credit line and a fire sale in 2014 [22:30] Why cash flow without liquidity is a trap [26:36] Flipping houses and an HGTV pilot [28:27] A lender with his own private banking system [29:50] Private Money Club, a dating site for money [31:46] Solve somebody else's problem [36:48] Earl Nightingale's 30-day challenge [37:46] Use AI to free up time for human relationships [40:11] What you think you know that just ain't so Resources Disclosure: Some links below are affiliate links. We may earn a commission at no cost to you. As an Amazon Associate we earn from qualifying purchases. Think and Grow Rich by Napoleon Hill The New Gold Standard by Joseph Michelli The Strangest Secret in the World by Earl Nightingale Private Money Club Be Your Own Banker Chris Naugle's website Chris Naugle on YouTube Chris Naugle on Instagram Chris Naugle on LinkedIn Get our free Passive Investor Starter Kit Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

October 19, 202654 min

The IRR Is a Load of Crap Says 50-Year Developer

After nearly five decades and more than 100 developments, John McNellis has a contrarian view of the metric the industry runs on: the IRR, he says, is "an utter load of crap." John McNellis is the co-founder of McNellis Partners, the Northern California firm he started 43 years ago with two colleagues, Beth Walter and Mike Powers. Together they have developed more than 100 properties, principally supermarket-anchored shopping centers. In this conversation John traces the path from journalism major to reluctant lawyer to developer, working nights and weekends on duplexes until the side business became the real one. He explains why he walked away from financial partners after seven-year deals that returned his firm nothing, why he would rather own 100 percent of a small deal than a fraction of a large one, and how he uses ground leases and leasehold interests other buyers avoid. He also covers the barbell shopping center model, knowing when to sell the disco while people are still dancing, keeping overhead low enough to survive a bad cycle, never relying on a single bank, and the four words he offers for financial security: one house, one spouse. Chapters [0:00] Why adaptive reuse beats ground up [1:57] Journalism major, then law school, then real estate [4:15] The barbell shopping center model [5:59] Why he would rather own 100 percent of a small deal [10:57] How ground leases actually work [15:20] Sell the disco while they are still dancing [17:09] Merchant builder versus investment builder [20:56] Why he walked away from financial partners [23:23] The IRR is an utter load of crap [25:18] Where we are in this cycle [29:55] Keep your overhead down [36:42] One house, one spouse [40:46] Risks to retail over the next 10 to 20 years [48:45] Making It in Real Estate, now in its third edition Free audiobook for the first 100 listeners. John is giving away Making It in Real Estate, 3rd edition, audiobook to the first 100 Truly Passive Income listeners who claim it. Resources Disclosure: Some links below are affiliate links. We may earn a commission at no cost to you. As an Amazon Associate we earn from qualifying purchases. Making It in Real Estate by John McNellis ULI, publisher of the first edition John McNellis on LinkedIn John McNellis on YouTube Get our free Passive Investor Starter Kit Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

October 12, 202638 min

He Sits Down With Presidents Before He Invests

Mikkel Thorup left school at twelve, dropped out at fifteen, and started traveling as a teenager. Twenty six years later he has lived in nine countries, visited more than a hundred and twenty, met his wife in Germany, married her in Africa, and had four children born in four different countries. He has never owned a single piece of real estate in the United States. Mikkel is the founder of Expat Money, a thirty-person firm with in-house lawyers and tax professionals that helps high net worth families relocate, secure second residencies, and build portfolios of foreign property. In this conversation he draws the distinction most people miss, that an expat is not an immigrant, and explains what that difference makes possible. He describes the homework he does before a dollar goes anywhere: understanding the culture, the economic drivers, the migration patterns, the national debt. He keeps a PhD political scientist on staff producing geopolitical reports, and he visits the countries himself, meeting local law firms, politicians, and on several occasions sitting presidents, including Santiago Pena of Paraguay. That last habit is the heart of his edge, and he makes the point sharply. In public markets, acting on private information is insider trading. In private markets it is simply the work: "private information is completely legal and it's completely what you should be doing." It is the difference between reading about a country and standing in it. Along the way he explains how his community buys entire pre-construction buildings for cash at a discount, why he favors Panama, what he genuinely thinks about safety in Colombia, how foreign tax credits keep US investors from paying twice, and why he would talk you out of that one euro house in Italy. Chapters [0:00] The homework behind investing overseas [0:51] Welcome and introduction [1:49] Left school at 12, and a life across nine countries [4:07] An expat is not an immigrant [5:46] Turning a life abroad into a business [7:12] He has never owned US real estate [9:43] Why your feed is suddenly full of foreign property [10:38] Who buys overseas, and what for [11:40] Is pre-construction riskier abroad? [12:47] Taking the entire building, and why developers agree [18:34] Warranties, title deeds, and what actually goes wrong [20:24] Where foreigners can and cannot own [21:36] Local law, geopolitics, and foreign tax credits [24:31] His favorite countries, and the case for Panama [26:36] Panama and Colombia: the safety question [27:26] Colombia's opportunity and its real risks [33:05] Why he believes the time in Latin America is now [35:19] Talk me out of a one euro house in Italy [37:25] Where to find Mikkel Resources Expat Money The Plan B Report, Mikkel's free special report The Expat Money Show podcast Mikkel Thorup on LinkedIn Mikkel Thorup on YouTube Mikkel Thorup on Facebook Get our free Passive Investor Starter Kit Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

October 5, 202652 min

He'll Reinvest With Operators Who Lost Him Money

After more than 100 syndications, a string of capital calls, two operators who turned out to be running Ponzi schemes, and the worst stretch the LP world has seen in a decade, Jim Pfeifer has a very different set of questions than he did in 2018. Jim Pfeifer is a former teacher and financial advisor turned full-time limited partner, and the founder of Passive Pockets, the community he started as Left Field Investors before BiggerPockets acquired it. In this conversation he is unusually candid about what the last few years cost him and what they taught him. He explains why his first question for any operator is now whether they are going to steal his money, why he walks away from solo sponsors and from deals with too many layers between him and the asset, and why he would happily reinvest with operators who lost him money while refusing to touch some who made him money. Jim also breaks down what a well-handled capital call actually looks like, why the old Left Field red line of "have you ever had a capital call" no longer makes sense, and where he is quietly putting capital now. He closes on an argument worth sitting with: that the next two to three years may be a better entry point for passive investors than 2017 and 2018 ever were, precisely because the cycle taught everyone what they did not know. Chapters [0:00] Why he's committing capital to real estate [2:09] Survive to 25, heaven in 27: the promise that keeps moving [8:16] The new first question: are you going to steal my money? [10:24] Red flags: solo operators and hidden layers [12:54] Should an LP ever sit out the market? [15:49] Why community shortens an expensive learning curve [21:39] The operators he lost money with and would back again [22:08] What a good capital call actually looks like [28:28] The question that used to be an automatic no [31:22] Where Jim is putting capital right now [36:48] His two biggest lessons: patience and liquidity [39:25] We all signed the PPM: where LP responsibility starts [43:02] Where is the value actually coming from? [47:47] The outlook for the next two to three years [50:32] Two books every passive investor should read Resources Disclosure: Some links below are affiliate links. We may earn a commission at no cost to you. As an Amazon Associate we earn from qualifying purchases. Passive Pockets, the community Jim founded as Left Field Investors Jim Pfeifer on LinkedIn Both Sides of the Table by Paul Shannon and Jim Pfeifer The Hands-Off Investor by Brian Burke Praxis Capital, Brian Burke's firm, whose assisted living fund Jim invested in InvestWise Collective, Paul Shannon's fund platform and the home of the Spectra fund Triple A Storage, the self storage development operator Jim tracked for two years before investing Get our free Passive Investor Starter Kit Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

September 28, 202635 min

The Mistake Most LPs Make Before They Ever Write the Check

With 24 years and more than 200 deals behind him, full-time passive investor Jeremy Roll explains the single metric that tells him whether to deploy capital or stay on the sidelines, and why most LPs get the timing exactly wrong. Jeremy Roll has been a full-time passive cash flow investor since 2007 and currently holds positions in more than 60 deals across over a billion dollars in assets. In this conversation he breaks down his framework for reading the real estate cycle: positive leverage spread. If he cannot get 125 to 150 basis points between the cap rate and the interest rate, he considers the market too expensive and waits. He explains why the riskiest value-add business plans get marketed at the worst point in the cycle, tells the story of a fully occupied student housing deal where four unexpected dominoes led to foreclosure, and describes the daily macro reading habit that lets him strip emotion out of his decisions. He also shares his unconventional read on Bitcoin's four-year cycle and why Warren Buffett's patience will be vindicated. Chapters [0:00] Cold open: the mistake most LPs make [0:19] Welcome and introduction [1:26] The 2019 call that aged well [1:58] Why he went to the sidelines in 2017 [3:09] Sidelines doesn't mean not investing [3:56] Paying too much, in stocks and in real estate [5:20] Positive leverage spread explained [5:49] How 2016 flipped deals to negative leverage [7:26] Why low rates don't guarantee a good deal [7:48] The best time to buy is when people are fearful [8:27] Concentration risk and the S&P 493 [9:56] Staying objective: Buffett's last laugh [10:18] Two to three hours a day on macro data [11:07] The top mistake he sees LPs make [11:45] Why he skipped floating rate bridge loans [13:25] The one metric that gets him off the sidelines [14:22] What actually causes market crashes [15:54] Red light, green light, and the line in the sand [16:53] You can't be surprised in retrospect [18:38] Why he's looking forward to bad times [19:07] Removing emotion, and the Bitcoin example [20:39] What a new real estate cycle really means [21:31] Why the business plan you receive is backwards [22:47] The runway analogy for value add timing [24:29] Dominoes: how a stabilized deal goes bad [25:26] The 303 unit student housing story [27:46] How the sponsor made investors whole [28:24] Mark Cuban and the Bitcoin question [29:37] The four year cycle on the chart [31:28] Closing the short and holding four years [33:35] Two books he recommends [34:10] Where to follow his research Resources Disclosure: Some links below are affiliate links. We may earn a commission at no cost to you. As an Amazon Associate we earn from qualifying purchases. Rich Dad Poor Dad by Robert Kiyosaki Rich Dad's Cashflow Quadrant by Robert Kiyosaki J Scott's newsletter , two to four economic analysis articles a week FIBI (For Investors By Investors), California's largest network of public real estate investor meetings, co-founded by Jeremy Jeremy Roll on LinkedIn Get our free Passive Investor Starter Kit Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

September 21, 202645 min

He Lost Everything in 2009, Now He Funds Billion-Dollar Lawsuits

Patrick Grimes lost everything in a speculative deal before the 2009 crash, rebuilt as an engineer, and now manages a diversified portfolio spanning apartments, litigation finance, and medical receivables that perform regardless of stock market cycles. Patrick Grimes is the founder and CEO of Passive Investing Mastery and a former robotics engineer who learned the hard way that concentrating in one asset class can be devastating. After losing his first investment ahead of the 2009 crash, he rebuilt by studying how the wealthy allocate capital across non-correlated industries. Today, Patrick finances contingency-fee law firms and medical practices, earning secured returns that behave nothing like real estate or equities. His thesis centers on three filters: recession resilience, non-correlation, and insulation from AI disruption. He explains how lending against a law firm's settled case portfolio or a medical practice's insurance receivables can deliver mid-teens to mid-twenties returns from a senior secured position. For high-income professionals already invested in real estate, Patrick Grimes offers a compelling framework for true portfolio diversification beyond familiar asset classes. Chapters [0:00] Cold open [2:06] Engineer to investor [5:53] Leaving engineering behind [8:05] Scaling to 3,000 units [11:14] Non-correlation explained [15:22] Litigation finance basics [18:06] Camp Lejeune case study [20:58] Mass torts explained [25:16] Medical receivables [28:30] Returns for investors [35:25] The AI disruption test [40:51] One passive step a day [43:35] The book offer Resources Passive Investing Mastery Get Patrick's free signed book (mention Truly Passive Income) Patrick's Favorite Alternatives download Lessons From Thought Leaders by Kyle Wilson, featuring Patrick's chapter Get our free Passive Investor Starter Kit Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

June 29, 202654 min

3 Questions That Make Your Kids Tell You Everything

Only 12% of couples who walk down the aisle end up in a truly fulfilling marriage, the same success rate as making it through Navy SEAL training. Larry Hagner has spent 11 years and 1,500 interviews figuring out why, and what fathers can do about it. Larry Hagner is the founder of The Dad Edge, host of one of the longest-running fatherhood podcasts in the world, and author of The Pursuit of Legendary Fatherhood. In this conversation, Larry shares the three questions he asks his kids every day to build trust and connection, why 80% of the time your spouse and children want validation instead of solutions, and how emotional intelligence is a learnable skill that most men were never taught. He explains why the couples who thrive share one trait: a purposeful commitment to keep growing together. For high-income professionals building passive income and financial freedom, Larry offers a critical reminder that the "why" behind the wealth is what matters most, and that being a great father and husband requires the same intentional skill-building we bring to our careers and investments. Chapters [0:00] Meet Larry Hagner [2:50] Why Larry started The Dad Edge [6:52] Marriage stats that will shock you [10:30] The dark moment that changed everything [30:40] Three daily questions for your kids [36:31] Validation over problem solving [48:22] What Larry still struggles with Resources Disclosure: Some links below are affiliate links. We may earn a commission at no cost to you. As an Amazon Associate we earn from qualifying purchases. The Pursuit of Legendary Fatherhood by Larry Hagner The Dad Edge: Book + Free Courses Bundle 25 Intimate Conversation Starters for Your Wife (free) Questions for the Car: Kid Questions by Age (free) "It's Not About the Nail" by Jason Headley The Dad Edge on Facebook The Dad Edge on X Get our free Passive Investor Starter Kit Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

June 22, 202641 min

This ER Doctor Doesn't Want Cash Flow (Here's Why)

What if chasing cash flow is actually costing high-income earners more in taxes than it's worth? Dr. Benjamin Aaker, an ER physician and multifamily syndicator, built a contrarian strategy around equity growth and tax-deferred wealth that made work optional a full decade ahead of schedule. Dr. Benjamin Aaker is an emergency medicine physician, multifamily syndicator, and author of Your Authority Problem. Operating out of South Dakota, he scaled from a single rental property to a 226-unit multifamily syndication by prioritizing equity over cash flow. His reasoning is simple: as a high-income earner, every additional dollar of passive income gets taxed at the top marginal rate. By structuring deals to be cash flow neutral and building equity instead, he plans to take income later when his tax bracket drops in retirement. Aaker also shares hard lessons from a syndication where occupancy plummeted to 25% after a nonprofit pulled tenant subsidies, and how setting investor expectations upfront saved those relationships. His approach offers a valuable alternative framework for high-income professionals who already have enough income and want to build long-term, tax-efficient wealth. Chapters [0:00] Meet Dr. Benjamin Aaker [2:45] The 50-year plan to optionality [8:12] First rental property story [10:55] Equity over cash flow explained [16:30] Scaling to 226-unit syndication [22:18] Occupancy crash and hard lessons [30:40] Setting investor expectations Resources Disclosure: Some links below are affiliate links. We may earn a commission at no cost to you. As an Amazon Associate we earn from qualifying purchases. The Millionaire Real Estate Investor by Gary Keller and Jay Papasan DoctorEquity.com, Dr. Benjamin Aaker's blog Get our free Passive Investor Starter Kit Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

June 15, 202636 min

The Hidden Bottleneck Blocking New Housing in America

A single infrastructure bottleneck, municipal sewer capacity, is quietly killing housing deals across the country. Tom Bartlett has spent 27 years solving it with compact wastewater treatment plants that cut developer costs by 40 to 50%. Tom Bartlett is the founder of Aquatech Systems, a company building decentralized wastewater treatment plants that allow developers to bypass overburdened municipal sewer systems. Joined by development partner Charles Poindexter of CG Design and Build, Tom explains how these compact, stainless steel plants treat wastewater to the highest standards while costing a fraction of traditional hookups. For real estate developers and land investors, the implications are significant: cheaper land outside municipal sewer lines, higher unit density per acre, faster permitting through North Carolina's engineered optional permit process, and phased infrastructure that reduces carry costs. In a country where aging sewer systems are failing and housing remains unaffordable, Bartlett's technology represents a real solution to a problem most investors never think about until it kills their deal. Chapters [0:00] Why sewer is a real estate bottleneck [2:48] Tom Bartlett's background [5:22] How decentralized sewer works [10:15] Cost savings per lot [14:52] Infrastructure and phased building [19:30] Unit density and land value [25:10] Failing systems across North Carolina Resources Aquatech Systems (Community Sewer) CG Design and Build Get our free Passive Investor Starter Kit Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

June 8, 202638 min

Why the Boring Investor Strategy Beats Home Runs

Paul Moore reviewed over 1,100 deals last year and invested in only six, a filter rate that reveals just how seriously the founder of Wellings Capital approaches risk in today's market. Paul Moore runs Wellings Capital, a real estate private equity firm managing roughly $180 million across self-storage, mobile home parks, industrial, and multifamily assets. A self-described former "certified shiny object chaser," Paul now applies Warren Buffett's principles directly to commercial real estate, focusing on what he calls the boring investor approach. In this conversation he breaks down the critical difference between investing and speculating, explains how his team uses preferred equity and JV hybrid equity positions to protect downside while preserving upside, and shares the 31-point due diligence checklist Wellings Capital uses to vet operators. Paul also discusses why fraud remains the number one risk in passive investing and how capital stack positioning has become central to his strategy after the painful lessons of the last three years. Chapters [0:00] Investing vs. Speculating [3:52] Lessons from the Market Shift [10:22] Capital Stack Positioning [18:15] Due Diligence on Operators [25:42] Asset Classes Right Now [33:40] How Wellings Capital Works Resources Disclosure: Some links below are affiliate links. We may earn a commission at no cost to you. As an Amazon Associate we earn from qualifying purchases. The One Thing by Jay Papasan and Gary Keller The Hands-Off Investor by Brian Burke Wellings Capital free resources and 31-point due diligence checklist Get our free Passive Investor Starter Kit Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

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