Advertise on podcast: The Wealth Elevator Podcast: Real Estate, Taxes, Investing

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club A host interviews Gabe Hogan, a tax attorney and former IRS revenue agent, about how IRS audits work, why high-profile taxpayers are treated as examples to drive compliance, and why taxpayers—not preparers—are usually on the hook for penalties and interest. Hogan describes IRS bureaucracy, outdated systems, staffing declines, and increased hiring of non-tax personnel, plus the growing use of AI models that flag more returns amid a shrinking workforce. He explains how returns are graded with DIF scores, how agents and managers triage audit “stacks,” and why clear categorization and attaching substantiation (e.g., cost segregation reports) can reduce audit risk. They discuss common self-prep and CPA errors (TurboTax, misclassification, NIIT on business exits), documentation needs, audit escalation paths (agent, manager, Appeals, tax court), and strategies like the Augusta Rule when properly documented. 00:00 Celebrity Audit Fear 00:50 Wild Deduction Stories 02:10 Meet Former IRS Insider 03:36 From Bulls to Tax Law 06:14 Credentials Alphabet Soup 13:09 Taxpayer Liability Reality 14:58 Why Not TurboTax 18:24 Augusta Rule Done Right 22:53 Breaking Up With Your CPA 25:20 How Audits Get Picked 27:13 DIF Scores Explained 29:42 Stacks Managers and Backlogs 33:59 Statutes and Audit Chess 35:28 Audit Negotiation Tactics 37:12 Audit Types And Escalation 40:19 IRS Fear And Compliance 42:14 Gray Area Tax Strategy 44:45 Substantiation And Materiality 51:23 Regional IRS Culture 54:25 Politics And IRS Slowdown 56:29 Guest Wrap And Contact 57:14 Deal Desk Pitch 01:00:11 Due Diligence Framework 01:02:46 Final Call To Action Connect with me: LinkedIn: https://www.linkedin.com/in/lanekawaoka/ Facebook: https://www.facebook.com/TheWealthElevator Instagram: https://www.instagram.com/TheWealthElevator Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club The host interviews Robin Mills, founder/CEO of Qamar Energy and author of The Myth of the Oil Crisis, about oil and gas investing amid the Iran conflict and disruptions in the Strait of Hormuz. Mills argues the world has ample oil resources and explains how the US shale boom (enabled by horizontal drilling, fracking, and crude-by-rail) reversed decades of US production decline, while early environmental backlash was often exaggerated despite real methane and leakage issues. He outlines Venezuela’s collapse under Chávez/Maduro, subsequent US actions and sanctions changes, and how the Iran war has sharply reduced Hormuz flows from about 20 million bpd to far lower levels, partly offset by pipelines and China’s large strategic stockpiles. The discussion clarifies how OPEC/OPEC+ influences prices via production and spare capacity, why that leverage is constrained during the blockade, and reviews long-term demand threats from renewables and EVs, offset by petrochemicals and aviation, plus rising electricity needs for AI and renewed nuclear interest. 00:00 Oil Investing and Iran 01:03 Myth of Oil Scarcity 02:44 Shale Boom Origins 04:31 Fracking Breakthrough Timeline 06:26 Majors vs Independents 08:14 Fracking Environmental Backlash 09:32 Venezuela Collapse and Comeback 13:06 US Oil Policy Tightrope 15:09 Iran War and Hormuz Blockade 18:57 Global Price Shock and Winners 20:12 Pipelines and What Comes Next 22:07 Why Prices Stayed Contained 23:27 Stalemate and Future Scenarios 23:47 OPEC Price Myth 24:16 OPEC Plus Explained 26:43 Spare Capacity Basics 28:25 US vs Saudi Flexibility 30:37 China Oil Wildcard 32:51 Investor Risks Volatility 34:15 Renewables And EV Shift 37:16 Future Oil Demand Drivers 39:09 Nuclear Comeback SMRs 43:00 Oil Outlook And Wrap Connect with me: LinkedIn: https://www.linkedin.com/in/lanekawaoka/ Facebook: https://www.facebook.com/TheWealthElevator Instagram: https://www.instagram.com/TheWealthElevator Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club Lane interviews economist Richard Duncan (author of The Dollar Crisis and The Money Revolution and publisher of Macro Watch) about how ending the gold standard in 1971 shifted capitalism into “creditism,” enabling massive US trade deficits, disinflation, falling rates, and explosive growth in debt and Fed balance sheet expansion that prevented depressions in 2008 and during COVID. Duncan contrasts post-2008 low inflation with post-COVID inflation driven by supply-chain blockages, and argues credit-driven liquidity has inflated asset valuations while accelerating AI breakthroughs and fueling China’s rise via persistent US deficits. They discuss the US–China AI and defense race, energy and nuclear power needs, and risks from higher inflation and rates amid stretched valuations. Duncan introduces “cognitism,” a coming system driven by exponentially expanding AI intelligence, and highlights sectors tied to AI, semiconductors, energy, data centers, robotics, and defense, plus key macro indicators to watch. 00:00 Meet Richard Duncan 00:44 Macro Watch Discount 01:03 From Gold to Creditism 05:09 Why Old Theories Fail 06:28 Credit Growth and 2008 08:31 COVID QE and Inflation 10:54 Debt Wealth and AI Boom 14:00 China AI Arms Race 17:12 Energy Nuclear and Chips 22:07 Stretched Valuations Risks 31:58 Cognitism Explained 37:36 AI Skills and Sectors 41:13 What to Watch Next 47:40 Wrap Up and Subscribe Connect with me: LinkedIn: https://www.linkedin.com/in/lanekawaoka/ Facebook: https://www.facebook.com/TheWealthElevator Instagram: https://www.instagram.com/TheWealthElevator Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club The speaker reviews real-life (anonymized) multifamily deal examples to help investors spot misleading underwriting and marketing tactics. Key topics include “manufactured” IRR boosts from aggressive refinance assumptions, unrealistic exit/reversion cap rates (and the difficulty LPs have validating prevailing market cap rates), and mismatches between large CapEx plans and modest rent-bump projections that may signal weak market fundamentals or hidden reserves. They discuss how cap rate compression can inflate paper returns despite being uncontrollable, why comparing discounts to 2021 pricing can be irrelevant, and how debt structure (fixed vs floating, term length, IO, extensions, prepayment penalties) affects refinance and exit risk. Additional red flags include preferred equity ahead of common equity, side-letter complications in the capital stack, and early distributions funded from reserves rather than operations, which can mask weak DSCR. 00:00 Cap Rate Question Setup 00:42 Market Shift Overview 01:21 Manufactured IRR Tricks 03:32 Reversion Cap Rate Games 04:22 Finding Real Cap Rates 07:34 Rent Bumps Vs CapEx 09:35 Discount Hype Reality 10:48 Cap Rate Cycle Bets 11:58 Debt Structure Risks 13:24 Stacking Red Flags 14:54 Preferred Equity Ahead 17:23 Return Of Capital Trap 19:11 DSCR And Fake Cashflow 20:28 Cap Compression Review 21:53 AI Deal Checklist 24:52 Capital Stack Exceptions 26:25 Final Q And Wrap Connect with me: LinkedIn: https://www.linkedin.com/in/lanekawaoka/ Facebook: https://www.facebook.com/TheWealthElevator Instagram: https://www.instagram.com/TheWealthElevator Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club The episode features Jack Raines, author of “Young Money,” discussing how growing up with money provides insider knowledge about elite career paths, target schools, networks, and promotion moves that can lead to high incomes, while students from poorer backgrounds often must choose safer banking or consulting roles to repay large loans and can’t take startup risks. Raines shares his own path from South Georgia and Mercer University football to Columbia Business School and venture capital, emphasizing education, early “prestige stamps,” and intentional living that matches life stages. The conversation explores status pressure on wealthy kids, anxiety and expectations in elite environments, and how socioeconomic differences can complicate relationships and marriage. It closes with Raines promoting his book and the host warning investors to avoid inexperienced operators by relying on trusted networks and semi-institutional sponsors. 00:00 Money Game Secrets 01:22 Meet Jack Raines 03:01 Small Town to VC 03:51 Entrepreneur Family Roots 06:58 Prestige and Network 09:49 Leaving the Southeast 11:31 Target Schools Reality 13:11 MBA as Golden Ticket 15:04 Pedigree for Family Firms 17:21 Spectrum of Wealth 18:32 Rich vs Poor Options 21:24 Capital and Quarters 22:36 Merit and Social Circles 25:39 Status Pressure on Rich 27:19 High Achiever Burnout 27:59 Pressure of Privilege 29:03 Expectations and Happiness Gap 30:18 New York Norms Shift 31:39 Parents and Independence 32:59 Stage Specific Living 35:30 Funding Kids Choices 37:59 Socioeconomic Marriage Friction 43:01 Money Mindsets in Couples 45:08 Young Money Plug 47:25 FOOM Investing Lessons 51:16 Community and Relationships Connect with me: LinkedIn: https://www.linkedin.com/in/lanekawaoka/ Facebook: https://www.facebook.com/TheWealthElevator Instagram: https://www.instagram.com/TheWealthElevator Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.

Do a cost seg go to theWealthElevator.com/costseg Lane hosts a monthly investor “lunch and learn” webinar replay on cost segregation with guest AJ Lyons of DIY Cost Seg, explaining how cost seg reclassifies non-structural property components into shorter 5- and 15-year lives to accelerate depreciation versus standard 27.5-year (residential) or 39-year (commercial) schedules, often pulling a significant portion of deductions into year one, especially when 100% bonus depreciation applies. They discuss who benefits (rental owners, short-term rentals, commercial, value-add renovations), timing (including doing studies after purchase via amended returns or Form 3115), CPA coordination, potential use cases like short-term rental material participation or real estate professional status, depreciation recapture considerations, pricing and fast report delivery, and audit defensibility and optional audit support. Lane also announces an accredited investor retreat Jan 15–17, 2027 and directs viewers to thewealthelevator.com/costseg and related resources. 00:00 Depreciation Big Picture 00:56 Retreat And Webinar Intro 02:15 Lunch And Learn Setup 03:37 Cost Seg Basics Explained 06:27 Bonus Depreciation And CPA Fit 09:39 Not A Loophole History 17:35 Who Benefits And Pricing 21:11 Fast DIY Process Walkthrough 23:26 Audit Risk And Support 28:01 Timing And Catch Up Rules 30:24 Q And A Recapture Value 38:39 Wrap Up And Next Steps Hosted on Acast. See acast.com/privacy for more information.

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club In this webinar, asset protection attorney Douglass Lodmell explains how investors and high-liability professionals should structure entities to reduce exposure, contrasting inside vs. outside liability and why LLCs are commonly used to hold rental properties. He discusses when to silo “dirty” assets like rentals and operating businesses, noting janitorial or similar high-risk businesses are typically kept separate and often run as an LLC taxed as an S-corp, while safer assets (brokerage accounts, stocks/bonds, many LP interests) can sit under a holding company such as an asset management limited partnership (AMLP). Lomel gives a rule-of-thumb of roughly $250k–$500k equity per rental-property LLC and emphasizes insurance as the primary defense. He explains why passive LP investors generally have no personal liability beyond their investment, outlines jurisdiction choices for LLCs vs. holding companies, and details adding an asset protection trust—favoring a hybrid “bridge trust” that can convert offshore if needed—along with considerations for homes, life insurance, crypto, and avoiding fraudulent transfers and tax-scheme promoters. 00:00 LP Liability Shield 00:35 Webinar Setup 01:18 LLCs and Liability Types 02:57 Why Passive LPs Win 04:21 Building a Holding Structure 07:28 Best States for Entities 09:20 How Many Properties per LLC 13:45 Siloing LP Interests 18:02 Dirty Assets and Side Silos 20:25 Doctor Lawsuit Scenario 21:40 Single Member LLC Tax Simplicity 23:55 Trust Layer and Collection Defense 27:03 Discovery Costs Reality 27:48 Settlement Leverage Assets 30:21 Negotiation Trump Card 34:15 Trust Options Offshore 38:04 Bridge Trust Sweet Spot 40:57 Layering LLCs Over Time 42:10 Insurance And Homestead 47:24 Crypto Placement Protection 49:17 Finding Hidden Crypto 51:30 Avoid Tax Trust Scams 55:12 Wrap Up And Contact Connect with me: LinkedIn: https://www.linkedin.com/in/lanekawaoka/ Facebook: https://www.facebook.com/TheWealthElevator Instagram: https://www.instagram.com/TheWealthElevator Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club This webinar introduces infinite banking/accredited investor banking using properly designed whole life insurance as a liquid, asset-protected “cash value” tool that can be borrowed against to invest while the full cash value continues to grow. The presenter explains why configuration matters—minimizing the insurance/base premium (often ~10%) and maximizing paid-up additions (PUAs ~90%) to reduce fees and commissions, improve early liquidity, and reach a faster break-even point. It contrasts a 90/10 design versus a 50/50 design, discusses dividends, tax-free loans/withdrawals, MEC limits, underwriting, policy loan rates (~4–6%), and use cases such as funding deals, emergency reserves, education funding, retirement income, mortgage payoff decisions, and legacy planning. A licensed, non-captive agent joins to explain illustrations, funding flexibility, and scenarios like “flash funding” after liquidity events. 00:00 Infinite Banking Overview 01:21 Why Replace the Bank 03:00 Whole Life vs Term 04:41 Core Policy Benefits 07:00 Loans and HELOC Analogy 10:43 Emergency Fund and Protection 11:28 Whole Life Scam Debate 12:08 Premium Split Secret Sauce 18:27 PUAs and MEC Limits 22:32 How to Use the Policy 30:49 Policy Illustration Break Even 33:02 Flash Funding New Setup 33:55 Choosing Carriers and Agents 36:10 Riders Underwriting and Timing 38:01 Advanced Triple Dip Ideas 38:38 Leverage With Safe Assets 39:13 Growth Years Deal Funding 40:42 Liquidity Uses And Expenses 41:13 Endgame Retirement And Protection 41:48 Funding Options For New Investors 42:34 Policy Loans Versus HELOC 47:41 Accredited Investor Banking 48:22 Courses Community And Trifecta 51:13 Advanced Home Purchase Strategy 53:12 Teaching Kids Controlled Debt 54:22 Break Even And Policy Review 55:43 Policy Design 10 90 Explained 01:00:57 MEC Limits And Flexibility 01:04:14 Costs Liquidity And Break Even 01:06:44 Carrier Choice And 50 50 Compare 01:09:23 Infinite Banking Fees 01:11:01 Policy Design Levers 01:11:52 Liquidity Versus Growth 01:13:15 Best Use Cases 01:20:21 Stacking Policies Strategy 01:24:12 Buy Borrow Die Explained 01:25:41 Loans Rates And Flexibility 01:28:01 Break Even Benchmarks 01:29:21 Windfall Funding Options 01:31:13 Qualifying And Insurability 01:32:52 Paid In Advance Premiums 01:35:58 Final Thoughts And Next Steps Connect with me: LinkedIn: https://www.linkedin.com/in/lanekawaoka/ Facebook: https://www.facebook.com/TheWealthElevator Instagram: https://www.instagram.com/TheWealthElevator Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club https://www.beckonaire.com/ [email protected] The host shifts from investing to spending on experiences through travel, referencing Bill Perkins’ idea of trading money for memories, especially after 40. He interviews David from Beckonaire, who designs bespoke luxury trips—hotels, villas, yacht charters, private tours, and complex logistics—explaining that travel advisors are typically paid commissions by hotels and can add perks like credits and upgrades without costing clients more. David argues advisors reduce risk and friction across transitions (transfers, visas, timing) and become essential as trip spend rises. They discuss typical five-star costs for a family of four, where luxury isn’t worth it (overpriced hotels and buzzworthy destinations), the value of boutique hotels, and examples of upgrades like meet-and-greet services, private boats, and special experiences. David emphasizes upfront conversations, rapport, and long-term “leisure time” planning across life stages. 00:00 Why Travel Matters 01:05 Meet the Luxury Planner 03:11 How Advisors Get Paid 04:56 DIY vs Pro Planning 06:24 What Luxury Costs 09:49 Easy Luxury Upgrades 14:50 When Luxury Is Not Worth It 16:44 Boutique vs Big Brands 18:49 How Pros Vet Hotels 21:00 Choosing the Right Advisor 24:42 Avoiding Instagram Traps 28:20 Designing Meaningful Trips 31:09 Thrill vs Comfort Balance 37:32 Hands On Family Memories 40:23 Exit Trips and Quick Getaways 44:22 Travel Before You Cannot 47:24 Travel as Time Investing 49:29 Where to Find David 50:10 Final Thanks and Goodbye Connect with me: LinkedIn: https://www.linkedin.com/in/lanekawaoka/ Facebook: https://www.facebook.com/TheWealthElevator Instagram: https://www.instagram.com/TheWealthElevator Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club The speaker discusses SpaceX going public and says he participated in a pre-IPO round, explaining how IPOs often surge initially before earlier employees and investors gradually sell, which can cause a pullback. He contrasts investing through the secondary market (public stocks, mutual funds, REITs, 401k products with fees and middlemen) versus the primary market (direct ownership, syndications, and earlier-stage access), arguing fundamentals favor investing in “rails” or infrastructure businesses. He outlines three ways to access pre-IPO shares: direct VC-level entry (often requiring very large checks), getting an allocation through a larger investor’s tranche (with carried interest), or buying tender-offer/secondary pre-IPO shares, which he cautions can be speculative. He shares his background in rental properties and syndications and emphasizes education, due diligence, and long-term risk in tech-style investing. 00:00 SpaceX IPO Hype 01:22 Primary vs Secondary Markets 02:47 Pre IPO Round Explained 03:43 IPO Pops and Pullbacks 04:58 Why SpaceX Wins Long Term 05:51 Elon as Capital Raiser 07:17 Building the Rails Analogy 08:48 My Investing Origin Story 09:58 How to Access Pre IPO Shares 13:05 Risks and Final Thoughts 13:51 Q&A and Book Plug Connect with me: LinkedIn:   / lanekawaoka   Facebook:   / thewealthelevator   Instagram:   / thewealthelevator   Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club The host interviews Matt, a former arena football quarterback and investor, about turning a nest egg from an earlier retail venture (selling the “wacky whistle,” which expanded from Hawaii to Dubai’s Global Village) into a football-themed short-term rental business, PigskinJourneyman.com. Matt explains how he built and self-manages themed properties near sports destinations—starting near Lambeau Field in Green Bay, expanding to South Bend near Notre Dame (including a two-house “Rockne compound”), and adding a pool property near the Pro Football Hall of Fame area in Massillon/Canton, Ohio. They discuss amenities and design, tools like Turno and PriceLabs, seasonality, platform reliance vs. direct bookings, operational workload, and regulatory risk. Matt shares 2025 plans to open a Jim Thorpe–themed property in Jim Thorpe, Pennsylvania, and considers future restructuring and possible expansion into boutique hotels or other ventures. 00:00 Podcast Twist Intro 01:18 Wacky Whistle Origins 02:00 Dubai Retail Chaos 03:59 Product Longevity Mindset 06:15 Real Estate Pivot Begins 06:54 Football Brand Story 09:20 Family Football Inspiration 10:29 No Guru Policy 14:21 Canton Market Strategy 17:26 Purchase Rehab Numbers 20:21 Revenue Ops Systems 22:26 Rockne Compound Expansion 24:18 Two Houses One Compound 25:14 Compound Pricing Strategy 27:13 Minimum Nights Party Risk 27:43 Dynamic Pricing With PriceLabs 29:29 Direct Booking Challenges 31:16 Next Market Jim Thorpe PA 33:17 Who Books These Stays 36:39 Scaling Risks And Diversification 37:35 Future Markets Hawaii Texas 39:13 Graduating Beyond STRs 42:13 Life Logistics And Time Zones 45:18 Wrap Up Links And Advice Connect with me: LinkedIn: https://www.linkedin.com/in/lanekawaoka/ Facebook: https://www.facebook.com/TheWealthElevator Instagram: https://www.instagram.com/TheWealthElevator Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club Lane hosts CPA Steve Nicokiris (connected via the Vistage Network) to explain leveraged ESOPs as a tax-advantaged way for small business owners—often with $5–$10M exits—to monetize and diversify wealth that is frequently 80% tied to the business. They compare ESOPs with traditional M&A sales and leveraged dividends, emphasizing ESOP flexibility to sell minority stakes, keep control, preserve legacy, and avoid finding an outside buyer. Steve outlines how ESOPs work (ERISA plan, trust structure, independent annual valuation, payroll-based share allocations and vesting), typical candidacy requirements (meaningful EBITDA, payroll, employees, ability to handle leverage and ongoing costs), and key pros/cons. They discuss special advantages for minority/women-owned businesses, retention benefits, and major tax and estate-planning tools including C-corp conversion and the Section 1042 rollover to defer or eliminate taxes. 00:00 Why Exits Trigger Taxes 01:09 Meet Steve From Vistage 01:39 Where Owners Hold Wealth 03:21 Three Exit Options 06:34 Legacy And Your Why 07:22 ESOP Buyer Is Internal 08:47 Who Qualifies For ESOP 09:53 Minority Owned Advantage 12:41 What An ESOP Is 14:06 Valuation And Annual Costs 15:46 Funding And Share Allocation 20:21 Benefits Monetize And Retain 25:36 Downsides Complexity And Debt 27:23 Seller Notes Reality Check 27:46 Best ESOP Candidates 28:30 Ongoing Costs and Leverage 29:44 Dress Business ESOP Win 31:23 Estate Planning Value Drop 32:31 Professional Services Fit 34:06 Fair Market Value Explained 35:43 Owner Commitment Required 37:11 Engineering Firm Numbers 39:42 ESOP as Bridge Strategy 41:36 Tax Benefits and 1042 44:32 Gifting Exemptions Strategy 45:49 Trusts and Team Approach 46:58 1042 Rollover Mechanics 48:56 Wrap Up and Contact Connect with me: LinkedIn: https://www.linkedin.com/in/lanekawaoka/ Facebook: https://www.facebook.com/TheWealthElevator Instagram: https://www.instagram.com/TheWealthElevator Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club The challenges of the “sandwich generation,” especially people 50+ balancing the financial and emotional demands of raising children while also managing aging parents’ care and sometimes their finances. It describes how caregiving responsibility often falls by default to the nearby, “responsible” sibling (“Cheryl”), and how unclear family roles and poor estate planning—like avoiding trusts or leaving illiquid assets—can create resentment and conflict. The pressure often forces people into a defensive, wealth-preservation mindset, delaying investing and diverting cash flow to education and parent-related needs. Many clients (often 55–65) only pursue alternative, direct investments after parents pass away, freeing bandwidth and capital and reducing fear of making mistakes. The episode emphasizes that this struggle is common and highlights the value of community and relationships among like-minded investors. 00:00 Sandwich Generation Intro 01:21 Meet the Caregiver Cheryl 02:30 Estate Planning Pitfalls 04:09 Money Choices Under Pressure 05:40 Wealth Building to Preservation 06:19 Post Sandwich Investing 07:25 Fear of Taking Risks 09:04 Testing Alternatives Slowly 10:01 You Are Not Alone 11:08 Community and Relationships Connect with me: LinkedIn: https://www.linkedin.com/in/lanekawaoka/ Facebook: https://www.facebook.com/TheWealthElevator Instagram: https://www.instagram.com/TheWealthElevator Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club Lane and Tyler discuss infinite banking using specially designed whole life insurance policies that minimize commissions and maximize paid-up additions to function like a liquid “pseudo bank account.” Using a $50,000 annual target premium over 10 years, they explain the 10/90 design (about 10% base premium, 90% cash value) versus a 50/50 design, covering funding duration, “bucket size,” annual minimums and maximums, rollover contribution room, and the IRS MEC (Modified Endowment Contract) limits. They compare early liquidity and break-even points—about years 3–4 for 10/90 versus around year 7 for 50/50—and note agent commissions can be about five times higher on the heavier base-premium design. They also cover carrier selection, illustration realism, use cases (investors, business inventory financing, college planning, wealth storage), policy loans, and options for large windfalls including splitting funding or paying premiums in advance. 00:00 Break Even Hook 00:29 Infinite Banking Basics 01:31 Designing a 10 90 Policy 04:39 Minimums Maximums and MEC 09:02 Choosing Carriers Wisely 10:03 Year One Cost and Break Even 14:44 10 90 vs 50 50 Comparison 19:04 Use Cases and Strategy Fit 22:10 High Net Worth Use Cases 23:07 Parents Funding Kids Policies 23:58 Early Access And Loan Cycling 24:49 Comparing Container Size 26:10 One Policy Or Stack 26:36 Agent Incentives And Fees 30:00 Buy Borrow Die Explained 31:27 Policy Loans Versus HELOC 33:50 Breakeven And Flexibility 35:10 Windfall Funding Strategies 37:02 Qualifying And Insurability 38:41 Paid In Advance Premiums 40:53 Start Early And Use Spouses 41:47 Wrap Up And Next Steps Connect with me: LinkedIn: https://www.linkedin.com/in/lanekawaoka/ Facebook: https://www.facebook.com/TheWealthElevator Instagram: https://www.instagram.com/TheWealthElevator Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.

📚 Unlock the secrets to building wealth! My book and 12-module Masterclass cover everything I’ve learned about passive investing and creating financial freedom. Watch it on-demand for FREE: http://thewealthelevator.com/master 🤝 Join the Hui Deal Pipeline Club and get a one-on-one call with me to discuss your investment goals: https://thewealthelevator.com/club This panel introduces investors discussing how family offices and operators are allocating and scaling amid higher interest rates. Lane Kawaoka, a Hawaii-based former engineer, shares his path from buying 11 rentals by 2015 to operating over $2B in apartment acquisitions, and explains why rising holding costs, insurance, and taxes have pushed him to also act as a multifamily office seeking opportunities beyond real estate. The conversation highlights a contrarian, P&L-driven approach, emphasizing grassroots relationship-based deal flow with long-term partners (brokers, contractors, vendors) and special real estate structures where developers need short-term capital to finish projects. The panel also covers using AI and quantitative checklists to quickly screen deals and reduce underwriting workload, plus a “$30k rule” of paying trusted third-party consultants to validate financials when investing outside core expertise. 00:00 Panel Kickoff 00:27 Lane Kawaoka Intro 01:33 Contrarian Investing Approach 03:11 Creative Deal Structures 04:20 AI Underwriting Workflow 05:29 Million Dollar Insight 06:49 Audience Q&A Wrap Connect with me: LinkedIn: https://www.linkedin.com/in/lanekawaoka/ Facebook: https://www.facebook.com/TheWealthElevator Instagram: https://www.instagram.com/TheWealthElevator Lane Kawaoka is a developer and multi-family syndicator who owns 10,000+ rental units and is the leader of “Hui Deal Pipeline Club” which has acquired over $2.1 Billion AUM of real estate by syndicating over $200 Million Dollars of private equity and most importantly distributed more than $45M back to our investors since 2016. Check out our Top-50 Investing Podcast, The Wealth Elevator. Hosted on Acast. See acast.com/privacy for more information.