Why High-Income Professionals Are Investing in Dirt, Not Buildings

How a Podcast Built a 95-Unit Real Estate Empire

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. IN THIS EPISODE YOU WILL LEARN * 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 CHAPTERS * [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 ABOUT RYAN BEVILACQUA AND CORY JACOBSON 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. RESOURCES MENTIONED 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 [https://www.amazon.com/Rich-Dad-Poor-Teach-Middle/dp/1612680194?tag=tpi2026-20] * Set for Life by Scott Trench [https://www.amazon.com/Set-Life-All-Out-Approach-Financial/dp/1947200801?tag=tpi2026-20] * Wealth Juice Podcast: Apple Podcasts, Spotify, YouTube CONNECT WITH CORY JACOBSON * Instagram: @wealthjuiceofficial [https://www.instagram.com/wealthjuiceofficial] * YouTube: youtube.com/@wealthjuiceofficial [https://www.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 [https://trulypassiveincome.com/toolkit/] Follow the show: YouTube @trulypassiveincomepod, Instagram @truly_passive_income, Facebook Truly Passive, Twitter @trulypassive #PassiveIncome #RealEstateInvesting #RealEstateSyndication

Your CPA Is Trained to Work for the IRS, Not You

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. TIMESTAMPS * [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 RESOURCES & LINKS MENTIONED * One Atlanta Tax Solutions (Chris Miller's firm) - https://oneatlantataxsolutions.com [https://oneatlantataxsolutions.com] * Truly Passive Income Passive Investor Toolkit - https://trulypassiveincome.com/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

Don't Buy SpaceX Stock Before You Understand This

Pre-IPO investing lets you buy into proven companies before the public stock market ever gets a chance - and the returns can dwarf traditional assets. Neil Kayal, founder of Grain Ventures and senior M&A executive at a Fortune 10 healthcare company, breaks down how late-stage private market investing works and why it belongs in a diversified portfolio alongside real estate and public equities. You will learn how special purpose vehicles let you invest deal by deal without blind pool commitments, how institutional due diligence filters separate real opportunities from hype, and why the biggest mistake private market investors make is simply waiting too long. Neil brings 15-plus years of evaluating acquisition targets at the highest level, and he has built Grain Ventures to democratize that same institutional rigor for accredited investors. If you have been looking for a growth allocation beyond syndications and index funds, hit play and discover a new asset class you may have been missing. oi35qc1jIG8OrnK7f24o WHAT YOU'LL LEARN * How late-stage private market investing differs from early venture capital and why it carries a fundamentally different risk profile * Why 90% of the world's companies are privately held and what that means for investors who only access public exchanges * The exact due diligence framework Neil uses to evaluate competitive moats, revenue flywheels, and exit probability for pre-IPO companies * How special purpose vehicles (SPVs) let you invest deal by deal without blind pool fund commitments or multi-million-dollar minimums * Why the biggest mistake new private market investors make is simply waiting for the next opportunity instead of acting when windows are open * How to think about sizing a pre-IPO allocation using a barbell investing strategy alongside real estate and public equities * The real fee structure and alignment model behind deal-by-deal pre-IPO investing, including carry, minimums, and SPV costs * Why real estate investors already think in the frameworks that make private market investing intuitive - location timing equals market timing TIME STAMPS [00:00] - Introduction [01:12] - How late stage private investing works [04:48] - Barbell investing and wealth creation [07:22] - Accredited investor misconceptions [10:15] - The institutional due diligence process [13:30] - Evaluating competitive moats in defense tech [18:05] - Reading fundraising signals and exit thesis [21:40] - Public vs. private market analogy for real estate investors [25:10] - How SPVs work and why deal-by-deal matters [30:45] - Fee structure, minimums, and alignment [34:20] - Biggest mistakes new private market investors make [37:50] - Sizing a pre-IPO allocation in your portfolio [40:30] - Book recommendations and how to connect ABOUT THE GUEST Neil Kayal is the founder of Grain Ventures, a curated investor network providing accredited investors with access to late-stage pre-IPO companies in sectors including AI infrastructure, energy, aerospace, and defense technology. By day, he serves as a senior mergers and acquisitions executive at a Fortune 10 healthcare company, where he has spent more than 15 years evaluating hundreds of acquisition targets with institutional-grade diligence. He built Grain Ventures to democratize the same deal access and underwriting rigor that was previously available only to billion-dollar pension funds and endowments. Website: https://grain-ventures.com [https://grain-ventures.com] LinkedIn: https://www.linkedin.com/in/neilkayal [https://www.linkedin.com/in/neil-kayal/] BOOKS & RESOURCES MENTIONED Disclosure: Some links below may be affiliate links. We may earn a commission at no cost to you. As an Amazon Associate I earn from qualifying purchases. * Sidecar [https://www.sydecar.io] (SPV administration platform) * Canopy [https://www.heycanopy.com] (SPV administration platform) * EQ Applied: The Real-World Guide to Emotional Intelligence [https://www.amazon.com/EQ-Applied-Real-World-Emotional-Intelligence/dp/0692066594?tag=tpi2026-20] by Justin Bariso * Blue Ocean Strategy [https://www.amazon.com/Blue-Ocean-Strategy-Expanded-Uncontested/dp/1625274491?tag=tpi2026-20] by W. Chan Kim and Renee Mauborgne * Anti-Fragile [https://www.amazon.com/Antifragile-Things-That-Disorder-Incerto/dp/0812979680?tag=tpi2026-20] by Nassim Nicholas Taleb (referenced by Neil Henderson) FOLLOW US ON SOCIAL MEDIA YouTube: Truly Passive Income [https://www.youtube.com/channel/UCe0F1abrRXQX2KpSl5qEnoA] TikTok: @trulypassiveincome [https://www.tiktok.com/@trulypassiveincome] Instagram: @truly_passive_income [https://www.instagram.com/truly_passive_income/] Facebook: Truly Passive [https://www.facebook.com/TrulyPassiveInc/] Twitter: @trulypassive [https://twitter.com/trulypassive] DOWNLOAD OUR FREE PASSIVE INVESTOR TOOLKIT Everything you need to get started in passive investing - Download Here [https://trulypassiveincome.com/toolkit/]

Why Being the Bank Beats Owning Rentals Right Now

Eddie Speed has purchased over 50,000 mortgage notes in a 45-year career, and he believes today's market is uniquely primed for seller-financed note investing. In this episode, Eddie breaks down how landlords can convert rental portfolios into performing notes, dramatically boosting cash flow while shedding maintenance headaches. He explains his mortgage-bank-style underwriting system, how he creates liquidity for note sellers, and why 40% of qualified buyers are locked out of conventional lending. Whether you are an accredited investor exploring a new asset class or a burned-out landlord hunting for better NOI, this conversation reframes what truly passive income can look like in 2025. TIME STAMPS [00:00:00] - Introduction [00:01:07] - How Eddie Got His Start Buying Notes in 1980 [00:03:30] - Why Rental Expenses Are Crushing Landlord Cash Flow [00:05:45] - Notes as the Middle Ground Between Syndications and Rentals [00:08:15] - What Is a Note? A Simple Explanation for Beginners [00:10:00] - How Seller Financing Differs from Subject-To and Wraps [00:13:30] - Eddie's Mortgage Bank Approach to Underwriting Notes [00:17:00] - The Math: Rent vs. Note Income on the Same Property [00:20:30] - Who Qualifies as a Seller-Finance Buyer Today [00:24:00] - How Mortgage Banking's Tightening Index Creates Opportunity [00:27:30] - Return Profiles and What a Grade-A Note Looks Like [00:30:00] - How Eddie Scales: Secondary Markets, Hedge Funds, and Investors [00:33:45] - The Rental Conversion Program for Landlords with 25-500 Units [00:37:00] - Why Land Contracts Destroy Note Value [00:39:30] - What Sophisticated Investors Still Underestimate About Notes [00:42:00] - Book Recommendation and Final Advice REFERENCES AND SOURCES Disclosure: Some links below may be affiliate links. We may earn a commission at no cost to you. As an Amazon Associate I earn from qualifying purchases. Book: "Never Split the Difference" [https://www.amazon.com/dp/0062407805?tag=tpi2026-20] by Chris Voss Resource: Note School [https://noteschool.com/] Resource: Note School Rental Conversion Program Company: HomeVestors (founded by Ken D'Angelo) Mastermind Groups Mentioned: Collective Genius, Boardroom, Investor Fuel Index Referenced: Mortgage Bankers Association Credit Availability Index GUEST LINKS Website: noteschool.com/trulypassive [https://noteschool.com/trulypassive] Facebook: https://www.facebook.com/thenoteschool [https://www.facebook.com/thenoteschool] LinkedIn: https://www.linkedin.com/in/eddiespeed/ [https://www.linkedin.com/in/eddiespeed/] YouTube: https://www.youtube.com/@NoteSchool [https://www.youtube.com/@NoteSchool] If you liked this, listen to our most popular episode on mortgage note investing here: https://trulypassiveincome.com/captivate-podcast/earn-passive-income-without-hassle-through-mortgage-note-investing-with-nathan-turner/ [https://trulypassiveincome.com/captivate-podcast/earn-passive-income-without-hassle-through-mortgage-note-investing-with-nathan-turner/] FOLLOW US ON SOCIAL MEDIA YouTube: Truly Passive Income [https://www.youtube.com/channel/UCe0F1abrRXQX2KpSl5qEnoA] TikTok: @trulypassiveincome [https://www.tiktok.com/@trulypassiveincome] Instagram: @truly_passive_income [https://www.instagram.com/truly_passive_income/] Facebook: Truly Passive [https://www.facebook.com/TrulyPassiveInc/] Twitter: @trulypassive [https://twitter.com/trulypassive] DOWNLOAD OUR FREE PASSIVE INVESTOR TOOLKIT Everything you need to get started in passive investing - Download Here [https://trulypassiveincome.com/toolkit/]

Why High-Income Professionals Are Investing in Dirt, Not Buildings

EPISODE DESCRIPTION Brandon Cobb, CEO of HBG Capital, reveals how he turns raw land into approved housing communities and sells finished lots to national builders like Lennar and D.R. Horton. In this episode, he breaks down the three phases of land development, explains how entitlements force appreciation before construction begins, and shares the seven-figure lessons that reshaped his approach to deal structure, interest reserves, and investor communication. Whether you are an accredited investor seeking passive income through real estate syndication or a builder looking to scale, this conversation delivers actionable insight into one of the most overlooked cash flow strategies in the market. TIME STAMPS [00:00:00] - Introduction  [00:00:30] - From Medical Device Sales to Real Estate Developer  [00:03:18] - The Failed Businesses Before the Breakthrough  [00:05:08] - Why Most Entrepreneurs Start the Wrong Way  [00:06:15] - Three Phases of Land Development Explained  [00:09:00] - How Entitlements Create Massive Value on Raw Land  [00:10:30] - The Hack for Working with City Officials and Planning Directors  [00:12:15] - De-Risking Deals Before Spending Real Money  [00:13:05] - When You Need a Land Use Attorney  [00:14:30] - Why AI Is a Game Changer for New Developers  [00:15:30] - Entry Level Housing and the Supply Demand Imbalance  [00:17:00] - Why Chasing Maximum Density Backfires  [00:18:45] - Designing Lots with the End Buyer and Builder in Mind  [00:20:30] - Seven Figure Losses in 2022 and the Lessons Learned  [00:24:00] - Interest Reserves, Loan Terms, and Negotiating with Lenders  [00:26:00] - Investor Communication When Things Go Wrong  [00:27:30] - Multiple Exit Strategies and the Skinny Dipping Test  [00:29:00] - Book Recommendation: The Untethered Soul  [00:31:30] - How to Connect with Brandon Cobb and HBG Capital RESOURCES & SOCIAL MEDIA: Book: The Untethered Soul by Michael Singer [https://www.amazon.com/dp/1572245379?tag=tpi2026-20] Book: The Surrender Experiment by Michael Singer [https://www.amazon.com/dp/080414110X?tag=tpi2026-20]  Book: Tools of Titans by Tim Ferriss [https://www.amazon.com/dp/1328683788?tag=tpi2026-20]   Resource: Learn Land Development Free Course [https://learnlanddevelopment.com/] Resource: HBG Capital Investor Waitlist [https://www.hbgcapital.net/waitlist/]  Resource: HBG Capital Free Ebook [https://www.hbgcapital.net/educational-recourses/#ebooks] CONNECT WITH BRANDON COBB Guest: Brandon Cobb, CEO of HBG Capital and Founder of the Land Development Accelerator Website: hbgcapital.net [hbgcapital.net]  Facebook: https://www.facebook.com/hbgcapital [https://www.facebook.com/hbgcapital]  Instagram: https://www.instagram.com/hbgcapital [https://www.instagram.com/hbgcapital]  LinkedIn: https://www.linkedin.com/in/hbgcapital/ [https://www.linkedin.com/in/hbgcapital/]  YouTube: https://www.youtube.com/@hbgcapital662 [https://www.youtube.com/@hbgcapital662] FOLLOW US ON SOCIAL MEDIA Truly Passive Income website: www.trulypassiveincome.com [http://www.trulypassiveincome.com] Truly Passive Income Twitter: @trulypassive