Truly Passive Income

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.

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.

Get our free Passive Investor Starter Kit

Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

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.

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.

Get our free Passive Investor Starter Kit

Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

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.

Get our free Passive Investor Starter Kit

Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

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.

• [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

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

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.

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.

Get our free Passive Investor Starter Kit

Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

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.

Get our free Passive Investor Starter Kit

Follow us: YouTube @trulypassiveincomepod | Instagram @truly_passive_income

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.

• [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

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

AI for small business owners is no longer optional - but most people are decorating the penthouse before the foundation is laid. Former NYC managing broker Gus Waite spent 20 years leading over 100 agents in corporate relocation before retiring and going all-in on artificial intelligence for independent real estate professionals. Now he helps business owners close gaps, simplify operations, and spend more time on the work they actually love. In this conversation, Gus joins Neil and Clint for a candid discussion about where AI adoption really stands, why small business collectives are the antidote to corporate workforce slashing, and how to use AI as a personalized coach to identify your blind spots and build systems around your strengths. You will also hear why the first step is never a complex workflow, what the "source code" method is, and how the intersection of human connection and AI might reshape your business and your life. Hit play if you are a business owner trying to figure out where to start with AI without losing yourself in the process.

• How to identify your "source code" - your values, voice, and ideal client profile - so every AI output sounds like you instead of generic slop
• Why decorating the penthouse before the foundation is laid is the most common AI adoption mistake and how to avoid it
• The reason most business owners stall with AI tools after one technical glitch and the simple fix that keeps momentum going
• How to use personality assessments with AI to get daily personalized coaching on your blind spots and decision-making patterns
• Why small business collectives and masterminds are the antidote to the PE-driven workforce replacement playbook
• The exact approach Gus uses in his Independent Brokers Collective: one workflow, one agent, implemented together over two sessions
• Why both early-twenties graduates and early-sixties professionals are entering the same uncertain job market and what that means for you
• How to reframe the AI conversation from "cut costs" to "increase revenue 20%" using your existing team as a force multiplier

• [00:00] - Introduction and guest background
• [02:14] - The AI adoption cycle: remember, forget, try, fail
• [04:47] - Decorating the penthouse before the foundation
• [06:30] - Using personality scores as AI coaching tools
• [09:52] - The source code: values, voice, and vision
• [12:18] - What happens if all work disappears in 5-10 years?
• [14:03] - The $11 trillion wage market PE firms are targeting
• [17:25] - Small business collectives as the antidote
• [20:47] - Reframing AI: revenue growth vs. cost cutting
• [24:30] - The documentary revelation: early 20s and early 60s face the same crisis
• [27:15] - Eternal truths and why human connection wins
• [29:40] - Recommended resources and where to start
• [31:10] - How to connect with Gus Waite

Gus Waite is a former actor, standup comedian, and 20-year veteran managing broker who led more than 100 agents in corporate relocation across New York City. After retiring from traditional real estate, he spent four years studying artificial intelligence before launching Real Estate Rewired AI With a Heart, a podcast and consultancy helping independent brokers access the same tools and technology available to the top 1%. He now runs the Independent Brokers Collective, a mastermind where small business owners implement AI workflows together. Gus is the founder of Growth Pilot Partners.

Website: https://www.growthpilotpartners.com

Email: [email protected]

Phone: (914) 420-8358

LinkedIn: Gus Waite

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing - Download Here

Cory Jacobson grew a 95-unit real estate portfolio by turning a podcast into a deal-sourcing and capital-raising engine, without cold-calling a single investor.

Cory Jacobson and his partner Ryan launched the Wealth Juice Podcast during COVID to share their early investing mistakes publicly. By year six, that real estate podcast had become their primary capital-raising tool: limited partners found them through the show, general partnership deals formed through podcast relationships, and the show opened rooms they had no business being in. Their current focus is value add multifamily in the Upper Valley, a micropolitan market on the Vermont and New Hampshire border near Dartmouth Health. With a 0.4% vacancy rate and a projected shortage of 10,000 housing units through 2030, the market sits below institutional radar and above retail competition. They target mismanaged A-minus and B-plus properties, bring rents to market, and in some cases furnish units for traveling nurses, capturing midterm rental premiums of 25 to 40% above long-term rents. The GP-LP structure is laid out plainly: preferred return goes to limited partners first, GP windfalls come at refinance or sale, and cash-on-cash distributions during the hold period are secondary.

The episode also covers the 1033 casualty exchange, a tax deferral mechanism triggered by total property loss from a fire, hurricane, or natural disaster. It functions like a 1031 but is almost unknown, even among CPAs. Cory explains the two-year replacement window, the IRS extension process, and why adequate insurance is non-negotiable for any real estate investor. The conversation rounds out with seller financing, a 10-year compounding ground-up development fund in the Phoenix-Scottsdale market, the distressed debt wall coming due before 2027, and the case for staying focused in one micropolitan market rather than chasing equity multiple across too many geographies.

• How the Wealth Juice Podcast replaced cold calls as Cory and Ryan's primary deal-sourcing and LP capital-raising tool
• Why general partners get paid last in a syndication and what that means for limited partner preferred returns and timing
• How to target value add multifamily in micropolitan markets that sit below institutional and above retail competition
• How furnishing units for traveling nurses and medical professionals produces midterm rental premiums of 25 to 40% above market
• What a 1033 casualty exchange is, how it differs from a 1031, and why almost no CPAs have ever processed one
• How Cory structures GP-LP acquisitions: LP capital covers the down payment and renovation costs, commercial financing covers the rest
• Why staying focused in one market protects against over-leverage as you scale toward 500 units

• [0:00] Intro
• [3:56] How It Started
• [9:19] STR Mistakes
• [13:09] Raising Capital
• [16:59] LP Structure
• [20:17] Micro Market Advantage
• [25:11] Passive Real Estate
• [31:33] The 1033 Exchange
• [36:37] Value Add Execution
• [41:16] Growth and Goals
• [43:18] Arizona Development Fund
• [45:23] Book Recommendations

Ryan Bevilacqua and Cory Jacobson are real estate investors, entrepreneurs, and co-hosts of the Wealth Juice Podcast, ranked in the top 1% of podcasts globally. With over 12 years of experience in business, sales, and hospitality, they have built a portfolio spanning long-term rentals, short-term rentals, multifamily apartments, and a 43-unit multipurpose resort, and actively raise LP capital for value-add multifamily acquisitions in Vermont and New Hampshire.

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
• Set for Life by Scott Trench
• Wealth Juice Podcast: Apple Podcasts, Spotify, YouTube

• Instagram: @wealthjuiceofficial
• YouTube: youtube.com/@wealthjuiceofficial
• Podcast: Wealth Juice on Apple Podcasts, Spotify, and YouTube

Truly Passive Income is hosted by Neil Henderson and Clint Harris. New episodes drop weekly.

Download our free Passive Investor Toolkit

Follow the show: YouTube @trulypassiveincomepod, Instagram @truly_passive_income, Facebook Truly Passive, Twitter @trulypassive

#PassiveIncome #RealEstateInvesting #RealEstateSyndication

Your CPA may be costing you $50,000 or more every year without even knowing it. Tax strategist Chris Miller reveals why.

Chris Miller, founder of One Atlanta Tax Solutions with over 15 years bridging the financial and tax worlds, explains why most CPAs are trained to be reactive rather than proactive and how that gap costs high earners tens of thousands annually. You will learn about leveraged charitable deductions with 5X multiples, aviation leasing strategies that wipe out W-2 income, tiny house depreciation plays that turn $17,000 into $170,000 in deductions, and why qualified retirement accounts may actually be "money jail" for your wealth. Chris also breaks down how the tax code is designed as an economic incentive, not a punishment, and how high-income professionals can build what he calls an "untaxable lifestyle" through proper entity structuring and trust planning.

• [00:00] - Introduction to Chris Miller
• [01:12] - Bridging the financial and tax worlds
• [04:45] - Why CPAs leave money on the table
• [08:20] - When to engage a tax strategist
• [10:33] - Leveraged charitable deductions explained
• [11:45] - Aviation leasing for W-2 earners
• [15:02] - Tiny house bonus depreciation strategy
• [19:30] - Building an untaxable lifestyle
• [24:15] - Self-made millionaire wealth patterns
• [28:40] - Avoiding the tail wagging the dog
• [32:10] - Recession-proof business investing
• [34:50] - AI tax analysis tool coming soon
• [36:30] - Special offer for TPI listeners

• One Atlanta Tax Solutions (Chris Miller's firm) - https://oneatlantataxsolutions.com
• Truly Passive Income Passive Investor Toolkit - https://trulypassiveincome.com/toolkit/
• TPI Episode 098 with Dr. Tyson Cobb on tax strategy for physicians
• TPI Episode 049 with Shannon Robnett on CPAs vs. tax strategists
• TPI Episode 088 with Eric Gordon on renewable energy tax credits
• The One Big Beautiful Bill (2025 federal tax legislation restoring 100% bonus depreciation)
• 1031 Exchange (tax-deferred real estate exchange strategy)
• Qualified Opportunity Zones
• Cost Segregation Studies
• Roth Conversion Strategies