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 Hogan describes IRS bureaucracy, outdated systems, staffing declines, and increased hiring of non-tax personnel, plus the growing use of AI models that flag more returns amid a shrinking workforce.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.