The Wealth Elevator Podcast: Real Estate, Taxes, Investing

Episodi

• I Got Into SpaceX Before the IPO. Here’s What Retail Investors Miss 13.06.2026 14min

  📚 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/clubThe 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 Hype01:22 Primary vs Secondary Markets02:47 Pre IPO Round Explained03:43 IPO Pops and Pullbacks04:58 Why SpaceX Wins Long Term05:51 Elon as Capital Raiser07:17 Building the Rails Analogy08:48 My Investing Origin Story09:58 How to Access Pre IPO Shares13:05 Risks and Final Thoughts13:51 Q&A and Book PlugConnect 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.
• Green Bay Football-Themed Airbnbs: PigskinJourneyman’s Short-Term Rental Business 09.06.2026 46min

  📚 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/clubThe 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 Intro01:18 Wacky Whistle Origins02:00 Dubai Retail Chaos03:59 Product Longevity Mindset06:15 Real Estate Pivot Begins06:54 Football Brand Story09:20 Family Football Inspiration10:29 No Guru Policy14:21 Canton Market Strategy17:26 Purchase Rehab Numbers20:21 Revenue Ops Systems22:26 Rockne Compound Expansion24:18 Two Houses One Compound25:14 Compound Pricing Strategy27:13 Minimum Nights Party Risk27:43 Dynamic Pricing With PriceLabs29:29 Direct Booking Challenges31:16 Next Market Jim Thorpe PA33:17 Who Books These Stays36:39 Scaling Risks And Diversification37:35 Future Markets Hawaii Texas39:13 Graduating Beyond STRs42:13 Life Logistics And Time Zones45:18 Wrap Up Links And AdviceConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.
• How Business Owners Use ESOPs to Reduce Taxes on an Exit w/ Vistage Speaker Steven Nicokiris 26.05.2026 49min

  📚 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/clubLane 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 Taxes01:09 Meet Steve From Vistage01:39 Where Owners Hold Wealth03:21 Three Exit Options06:34 Legacy And Your Why07:22 ESOP Buyer Is Internal08:47 Who Qualifies For ESOP09:53 Minority Owned Advantage12:41 What An ESOP Is14:06 Valuation And Annual Costs15:46 Funding And Share Allocation20:21 Benefits Monetize And Retain25:36 Downsides Complexity And Debt27:23 Seller Notes Reality Check27:46 Best ESOP Candidates28:30 Ongoing Costs and Leverage29:44 Dress Business ESOP Win31:23 Estate Planning Value Drop32:31 Professional Services Fit34:06 Fair Market Value Explained35:43 Owner Commitment Required37:11 Engineering Firm Numbers39:42 ESOP as Bridge Strategy41:36 Tax Benefits and 104244:32 Gifting Exemptions Strategy45:49 Trusts and Team Approach46:58 1042 Rollover Mechanics48:56 Wrap Up and ContactConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.
• The Sandwich Generation: aging parents and raising kids 12.05.2026 11min

  📚 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/clubThe 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 Intro01:21 Meet the Caregiver Cheryl02:30 Estate Planning Pitfalls04:09 Money Choices Under Pressure05:40 Wealth Building to Preservation06:19 Post Sandwich Investing07:25 Fear of Taking Risks09:04 Testing Alternatives Slowly10:01 You Are Not Alone11:08 Community and RelationshipsConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.
• Infinite Banking: 10/90 vs 50/50 Whole Life Policy, Cash Value, MEC Limits & Break-Even 28.04.2026 42min

  📚 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/clubLane 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 Hook00:29 Infinite Banking Basics01:31 Designing a 10 90 Policy04:39 Minimums Maximums and MEC09:02 Choosing Carriers Wisely10:03 Year One Cost and Break Even14:44 10 90 vs 50 50 Comparison19:04 Use Cases and Strategy Fit22:10 High Net Worth Use Cases23:07 Parents Funding Kids Policies23:58 Early Access And Loan Cycling24:49 Comparing Container Size26:10 One Policy Or Stack26:36 Agent Incentives And Fees30:00 Buy Borrow Die Explained31:27 Policy Loans Versus HELOC33:50 Breakeven And Flexibility35:10 Windfall Funding Strategies37:02 Qualifying And Insurability38:41 Paid In Advance Premiums40:53 Start Early And Use Spouses41:47 Wrap Up And Next StepsConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.
• Growth Focus Finder Panel: Family Office Deal Flow, AI Underwriting & Real Estate Structures 14.04.2026 7min

  📚 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/clubThis 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 Kickoff00:27 Lane Kawaoka Intro01:33 Contrarian Investing Approach03:11 Creative Deal Structures04:20 AI Underwriting Workflow05:29 Million Dollar Insight06:49 Audience Q&A WrapConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.
• Self-Directed IRA vs Solo 401(k): Checkbook Control, Prohibited Transactions, and UBIT/UDFI Explained 31.03.2026 1h 29min

  📚 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/clubSelf-Directed IRA vs Solo 401(k): Checkbook Control, Prohibited Transactions, and UBIT/UDFI ExplainedLane and John Park discuss how investors can use qualified retirement plan funds to invest in non-traditional assets like real estate and private equity through true self-directed structures, contrasting them with “self-directed” brokerage accounts that still limit investments. They compare self-directed IRAs (which require an IRS-approved custodian) with Solo 401(k)s (which allow the account holder to be the trustee), explaining checkbook control via IRA LLCs or IRA trusts, including why trusts can reduce recurring LLC fees in states like California. The conversation covers Solo 401(k) eligibility (legitimate self-employment with no employees other than a spouse), higher contribution limits, Roth options, participant loans, and the exemption from UDFI. They also review prohibited investments (life insurance and collectibles), disqualified persons rules, UBIT/UDFI tax concepts, deal-funding timelines, and investor Q&A including a real-world UBIT surprise from new-build profits.00:00 Intro to Self Direction01:00 Solo 401k Eligibility02:33 Why Big Brokers Fail06:38 Checkbook Control Basics09:13 IRA Trust Option11:03 Solo 401k Advantages13:13 SDIRA Setup and Funding13:54 Custodian vs Control20:46 Prohibited Assets Rules23:04 Disqualified Individuals25:28 UBIT and UDFI Taxes28:25 UDFI Real Estate Example31:26 Solo 401k Tax Exemption33:47 Solo 401k Setup Details36:18 Solo 401k Loan Feature37:00 Plan Rules vs IRS38:46 Contribution Limits Explained42:13 Loan Terms and Repayment43:28 Roth and Backdoor Strategies46:43 Paying Kids and Audits47:58 Punting Taxes with QRP51:02 Setup Timeline and Funding54:18 Checkbook Control Custodians58:25 When QRP Investing Makes Sense01:04:37 Retirement Tax Trap Parents01:06:26 Parents Money Risk Choices01:07:24 How Much to Retire01:08:54 Stop Overfunding 401k01:10:32 Back Into 4 Percent Rule01:13:47 Financial Independence Mindset01:14:53 Three Bucket Strategy01:16:51 Kids Inheritance Limits01:19:28 UBIT Surprise in Solo 401k01:21:29 Blocker Corps and AI Learning01:24:10 Finding the Right Tax Pro01:28:17 Trivia and Wrap UpConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.
• 2026 Mortgage Rate Update: What’s Happening with Rates, Treasuries, DSCR Loans, and Investor Lending (with Jen Hernandez) 17.03.2026 32min

  📚 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/clubThe host interviews mortgage expert Jen Hernandez to get an update on the residential mortgage landscape after 2020, focusing on one-to-four unit properties and what single-family investors and homeowners are seeing in 2026. Jen explains that rates nearly doubled quickly in 2022 and have hovered in the low 6% range for about six months, with forecasts from major institutions (Fannie/Freddie and large banks) calling for mostly flat movement and possibly high-5% rates, but no major drops expected. She notes that historically very low rates have coincided with government “rescue” periods, and suggests watching the 7- and 10-year treasuries because mortgage pricing tracks those longer-term bond instruments more closely than the Fed’s overnight rate. They discuss the common misconception that Fed cuts immediately lower mortgage rates, and Jen explains how bond-market behavior, investor risk appetite, and the inverse relationship between stocks and bonds can move mortgage rates differently from the Fed funds rate.Jen gives practical guidance on whether to buy now versus wait, emphasizing that the answer depends on local market conditions; in Houston/Texas she’s seeing some price suppression, more seller negotiation, and opportunities for closing-cost credits or rate buydowns. She argues that a 6% rate is not bad historically and that buyers can refinance later, while purchasing during softer pricing may allow for future appreciation. The conversation then shifts to investor lending options, including DSCR (debt service coverage ratio) loans that rely on market rent rather than full income documentation, can allow financing in an LLC, and may offer rates that are sometimes better than conventional—though typically with a 2–3 year prepayment penalty and baked-in points (around 1.5%). Jen outlines DSCR qualification constraints, especially the need for market rent to cover PITI(A), which can push required down payments from 20% to 25% in high tax/insurance areas like Texas.They cover appraisal and rent trend observations in Houston (generally stable, with some appraisals coming in at or above price), discuss when investor “experience” matters (primarily when using rental income from tax returns to offset debt), and explain the lending ecosystem: big banks/servicers, direct lenders who underwrite and fund in-house, and brokers who connect borrowers to lenders but don’t control underwriting or timelines. Jen details reserve requirements for investment loans (typically 3–6 months of PITI(A), often across all mortgaged properties), warns that consumer credit scores from apps may differ from mortgage FICO models, and recommends getting prequalified months in advance to optimize credit and terms. Finally, they touch on high-net-worth purchase behavior in Houston (cash purchases, leveraging investment lines, recasts, ARM usage), personal views on leverage, and how to contact Jen via loanwithjen.com, noting she can lend in 42 states and can refer trusted contacts elsewhere.00:00 Mortgage Market Snapshot00:49 Rates After 202002:22 Tracking Rates Like Pros04:12 Fed vs Treasury Explained08:22 Buy Now or Wait12:19 DSCR Loans and Down Payments16:50 Appraisals and Rent Data19:15 Direct Lenders vs Brokers23:31 Reserves and Credit Prep27:38 How Wealthy Buyers Finance30:44 Wrap Up and Contact Info Hosted on Acast. See acast.com/privacy for more information.
• Tax-Free Gains: QSBS for Startup Investments 03.03.2026 37min

  📚 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/clubIn this episode, we dive deep into the strategy of investing tax-free into startups and operating businesses using Qualified Small Business Stock (QSBS). Joined by CPA Thomas Jones from Sweeney Conrad, we explore the intricacies behind QSBS, part of tax section 1202, that offers potential tax-free gains up to $15 million on eligible stock held for a minimum period. We discuss the eligibility criteria, the types of businesses that can benefit, different investor scenarios, and potential pitfalls to watch out for. Learn how to effectively leverage QSBS for significant tax savings and make informed investment decisions, whether you're an angel investor or a business owner.00:00 Introduction to Tax-Free Investing in Startups00:28 Meet the Expert: CPA Thomas Jones01:04 Understanding QSBS: Qualified Small Business Stock03:15 Industries and Use Cases for QSBS06:34 Asset vs. Stock Sales: Key Differences12:09 Investor Considerations and Tax Benefits25:00 Advanced Strategies and Pitfalls35:24 Conclusion and Contact InformationConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.
• Multifamily Market Trends & Predictions for 2026 | Podcast Update 17.02.2026 11min

  📚 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/clubJoin us in today's podcast as we provide a comprehensive update on the multifamily real estate market. We'll cover the market's recent history and predict where it's headed, focusing on key changes in prices, demand, rental growth, and supply. We'll also discuss the importance of long-term fundamentals and interest rate expectations. If you're interested in gaining more insights, attending private events, or participating in live webinars, visit wwealthelevator.com/club. Don't miss our live webinar on February 18th, 2026, for goal-setting strategies. Additionally, mark your calendars for our in-person event in Denver, Colorado, in March 2026.00:00 Introduction and Podcast Overview00:10 Upcoming Events and Webinars01:18 Multifamily Market Update01:52 Key Takeaways on Prices and Demand03:11 Rent Growth and Market Dynamics05:00 Supply Pipeline and Construction Challenges06:34 Long-term Fundamentals and Interest Rates09:24 Conclusion and Final ThoughtsConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.
• Tax Savings for 2026 with Tony Hong, CPA 03.02.2026 44min

  📚 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/clubJoin Tony Hong, a licensed CPA with over a decade of experience, as he walks you through essential tax planning strategies in this comprehensive masterclass. Discover the importance of having a tax strategy versus just filing taxes, and learn how to save money and stay compliant. Tony delves into common tax misconceptions, the pitfalls of using TurboTax for complex tax situations, and the levels of tax management from basic to advanced. Learn about various tax-saving opportunities, including the benefits and drawbacks of different business structures, investment tax credits, income shifting, and the importance of real estate professional status. Tony also discusses practical scenarios, such as the real-world struggles of W2 employees to optimize their taxes and how certain tax strategies can significantly reduce your tax liability. This session is packed with valuable insights to help you create an effective tax strategy for the new year. Don’t miss out on tips that could save you thousands of dollars annually.00:00 Introduction and Welcome00:26 Meet Your CPA: Tony Hong00:58 The Importance of Tax Planning01:24 TurboTax vs. Professional CPA03:12 Tax Strategies for Real Estate Investors08:04 Advanced Tax Planning Techniques09:42 Entity Structures: LLCs, S Corps, and C Corps14:10 Tax Benefits for Passive Investors19:16 Income Shifting and Investment Tax Credits21:22 Introduction to Capital Gains and Depreciation Recapture21:36 Unlocking Passive Losses from Syndication Deals23:37 Grouping Elections and Their Implications26:51 Charity and Tax Deductions29:38 Real Estate Professional Status and Tax Strategies33:51 Investment Tax Credits and Passive Investing43:24 Final Thoughts and Tax Planning AdviceConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.
• Buffett’s 2-Step Formula REVEALED (And the New 4-Step Strategy to Beat the Market) 20.01.2026 40min

  📚 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/clubIn this episode, we delve into the world of investing in individual stocks with expert Daniel Jiwani, author of 'Pick Stocks That Go Up' and 'Buffet's Two-Step Stock Market Strategy.' Daniel shares his journey from his first investment at 16 to becoming an accomplished investor by studying Warren Buffett's methodologies. We discuss the key aspects of successful investing, including identifying wonderful companies, buying at a wonderful price using discounted cash flow, maximizing upside by choosing growth industries, and essential risk management strategies. Whether you're interested in stocks, real estate, or other financial assets, this discussion offers valuable insights to enhance your investment strategy and make more informed financial decisions.00:00 Introduction to Stock Investing00:15 Guest Expert: Daniel Jiwani01:13 The Importance of Discounted Cash Flow02:14 Stock Market Realities04:49 Avoiding Investment Losers13:57 The Four-Step Investment Strategy20:49 The WorldCom Scandal: Earnings vs. Cash Flow21:44 Netflix's Accounting Practices22:32 Warren Buffet's Investment Philosophy23:01 Maximizing Upside Potential23:11 The Coca-Cola Case Study25:14 Angel Investors and Upside Potential26:26 Managing Investment Risk31:14 Economic Profits and Industry Attractiveness32:54 The Flipping Mindset vs. Cash Flow Mindset36:27 Investment Strategies and Portfolio Management38:33 Conclusion and Final ThoughtsConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.
• 2026 Market Predictions: Real Estate, AI, Interest Rates, Private Equity, Energy 06.01.2026 1h 10min

  📚 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/clubIn this 2026 market preview, we offer key predictions and insights into public and private investments, with a focus on AI, real estate, and key macroeconomic trends. We'll discuss recent Fed rate cuts, the concentration risk in public markets, and the implications for real estate investors. The video also covers the impact of interest rates on various asset classes, including multifamily housing, single-family homes, and the retail sector. Additionally, we delve into the increasing trend of retail capital flowing into private markets, the significance of business acquisitions by baby boomers, and the growing influence of AI and technology on investment strategies. Stay tuned for practical advice on asset allocation, the benefits of involvement in private equity, and the importance of understanding market cycles to make informed investment decisions for 2026 and beyond.00:00 2026 Market Preview Introduction00:24 Current Market Conditions and Predictions01:42 Understanding Public vs. Private Markets03:44 Valuation-Led Correction Cycle06:05 Real Estate Market Insights18:49 Retail Capital and Private Markets20:44 Baby Boomers and Business Transfers23:12 Interest Rates and Real Estate Strategies24:08 Inflation and Investment Predictions25:02 Single Family Homes and AI Impact26:17 Hospitality and Private Credit Funds28:48 Multifamily and Long-Term Investments31:44 Community and Investor Goals33:46 Transition to Macroeconomics34:00 Emerging Investment Trends: AI, Crypto, and Bioscience34:54 Manufacturing and Defense: Shifting Landscapes35:55 AI's Impact on Investment Strategies38:39 Energy Sector Insights: Clean Energy vs. Fossil Fuels42:31 Commercial Real Estate: Current Trends and Future Outlook52:27 Single Family Homes and Market Dynamics55:49 Investment Strategies and Market Cycles59:56 Multifamily Sector and Institutional Investments01:06:47 Final Thoughts and Future PredictionsConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.This message is for informational purposes, assessing potential investor interest, and isn’t an offer to sell securities or investment products. Investors must review and sign all offering documents, including the Private Placement Memorandum, which supersedes previous communications. While we aim for reliability, investors should conduct due diligence. Stated objectives are illustrative; past performance doesn’t guarantee future results. Tax implications of investments can vary; we don’t offer tax/legal advice. Investors should consult certified tax professionals/legal advisors for tax outcomes based on individual circumstances. Hosted on Acast. See acast.com/privacy for more information.
• Decumulation Tactics in 50s: Preparing for Financial Independence & Retirement 29.12.2025 20min

  📚 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/clubIn this episode, we dive into 'Decumulation Tactics,' an essential topic for those nearing retirement. Aimed at individuals in their fifties on the second or third floor of the 'wealth elevator,' we explore strategies for drawing down your wealth effectively as you approach the last quarter of your life. We discuss everything from creating a spending plan, the importance of trading money for experiences, to avoiding common mistakes like overly conservative drawdown strategies. We also touch on the emotional and psychological aspects of this phase, informed by real-world examples and insights from the Bill Perkins book 'Die With Zero.' Additionally, we announce upcoming retreats and community events, emphasizing the importance of interaction and shared learning. Tune in to gain valuable insights on how to enjoy your nest egg while preserving your financial security.00:00 Introduction to Decumulation Tactics00:50 Reflecting on a Decade of Podcasting02:24 Upcoming Events and Community Announcements03:14 Understanding Decumulation and Its Importance05:13 Strategies for Smart Decumulation07:37 Real-World Examples and Mistakes to Avoid12:38 Setting Goals and Planning for the Future19:21 Conclusion and Final Thoughts Hosted on Acast. See acast.com/privacy for more information.
• Lines of Credit with Business Owner Andrew Amann from ninetwothree.co 23.12.2025 50min

  📚 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/clubLane chats with his friend Andrew, an accomplished entrepreneur who transitioned from being a mechanical engineer working on government defense projects to running a successful AI consulting business. Andrew shares his journey, insights on entrepreneurship, the importance of cash management, and how he leverages different financial strategies to maintain and grow his business. They also discuss the ups and downs of entrepreneurship, the significance of having a solid support system, and Andrew's experiences working with big names like SimpliSafe and FanDuel. This conversation offers invaluable lessons for current and aspiring business owners looking to navigate the complexities of starting and scaling a company.00:40 Infinite Banking and Business Owners02:15 Podcast Introduction with Andrew Amen03:42 Andrew's Journey from Engineer to Entrepreneur06:40 Financial Struggles and Lessons Learned13:55 Consulting Business and Financial Strategies26:20 Understanding Brokerage Accounts27:12 Leveraging HELOCs for Business and Personal Finance29:05 Navigating Financial Challenges31:14 The Importance of Good Debt36:07 AI Studio Success Stories37:13 Future Plans and Exit Strategies41:51 Financial Planning and Monte Carlo Simulations44:17 Personal Finance Advice for Entrepreneurs46:24 AI Studio Services and Client Acquisition48:18 Mascot Memories and Closing RemarksConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.
• Ask an Estate Attorney: Values & Planning with Andrew Howell 16.12.2025 28min

  📚 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/clubLane interviews Andrew Howell, an experienced lawyer specializing in tax and estate planning. Andrew shares his expertise on the importance of proactive estate planning and the generational transfer of wealth. He emphasizes the need for crafting plans based on clients' core values and family dynamics, rather than a one-size-fits-all approach. Topics covered include the pitfalls of traditional estate planning methods, the impact of generational shifts in thinking about wealth, and the benefits of keeping assets concentrated within the family. Andrew also introduces the concept of purpose trusts and offers insights into how families can successfully navigate the transfer of assets across generations while maintaining cohesion and avoiding common pitfalls.00:56 Common Pitfalls in Deal Flow03:39 Estate Planning Insights with Andrew Howell12:59 Core Values in Estate Planning16:27 Practical Implementation of Estate Plans26:43 Final Thoughts and Contact InformationConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.
• Rethink Your 401(k) Strategy Now: Important Tax Implications 09.12.2025 6min

  In this episode, we delve into why many investors over 55 regret heavily contributing to deferred 401(k)s and other retirement plans, primarily due to future high tax brackets. We discuss alternative investment strategies like real estate, which offer immediate tax benefits, and caution against the long-term tax implications of deferred retirement plans. Tune in for insights on whether to keep money in qualified retirement plans or invest it elsewhere, and learn about our upcoming Hawaii retreat for deeper financial discussions.00:00 Introduction: The Pitfalls of Deferred Retirement Plans00:42 Upcoming Hawaii Workshop Details01:53 Podcast Introduction: Rethinking 401Ks and IRAs02:01 Key Points on Retirement Plans and Taxes03:38 The Importance of Tax Benefits Today05:34 Conclusion and Final Thoughts06:29 Join Our Annual Hawaii Retreat Hosted on Acast. See acast.com/privacy for more information.
• Networking with Accredited investors is Critical 02.12.2025 35min

  📚 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/clubIn this episode, we dive into a podcast replay where Lane Kawaoka, founder of Wealth Elevator, shares the inner workings of his investment retreats and the importance of building real relationships with other accredited investors. He discusses the need for curiosity, the value of mentorship, and the significance of community in personal and financial growth. Lane also highlights his journey from an engineer to a full-time investor, the importance of alternative investments, and how his events foster meaningful connections among high net worth individuals. The episode wraps up with insights on how to prepare for major life transitions and the future plans for Wealth Elevator.00:00 Introduction and Podcast Replay Announcement00:40 Guest Introduction and Initial Thoughts on Growth01:14 The Importance of Curiosity and Coaching02:26 Building Confidence and the Role of Peer Groups05:10 Adapting Strategies for Changing Environments07:15 Lane's Real Estate Journey and Investment Strategies12:38 Transitioning from Engineering to Full-Time Business17:10 Creating Effective and Curated Community Events29:01 The Future of Community and Human Connection33:11 Closing Thoughts and Final RemarksConnect with me:LinkedIn: https://www.linkedin.com/in/lanekawaoka/Facebook: https://www.facebook.com/TheWealthElevatorInstagram: https://www.instagram.com/TheWealthElevatorLane 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.
• Taxes Before Year-End: Using Oil & Gas Investments to Lower Ordinary Income 25.11.2025 1h 3min

  In this episode, Lane and guest tax expert Jack Hollander dive into strategies for offsetting ordinary income through oil and gas investments. They discuss the unique tax benefits, including intangible drilling costs and depletion allowances, and how these can provide significant deductions for high-income earners. The conversation addresses common mistakes with passive losses and real estate professional status, provides insights into how to properly utilize oil and gas investments, and answers questions on minimizing tax liabilities and optimizing portfolio strategies.00:00 Introduction to Tax Deductions in Oil and Gas Investments00:39 Understanding Passive and Ordinary Income01:11 Limitations of Passive Losses02:09 Real Estate Professional Status and Short-Term Rentals02:48 Introduction to Oil and Gas Investments03:02 Misconceptions About Bonus Depreciation06:08 Importance of Consulting Professional Advisors07:42 Basics of Tax Law and Income Buckets12:07 Financial Planning and Investment Considerations13:24 How Oil and Gas Investments Fit into a Portfolio15:23 Tax Benefits of Oil and Gas Investments23:53 Intangible Drilling Costs (IDCs) Explained35:16 Understanding Passive Losses and Tax Benefits35:53 Investment Strategies for Self-Employed Individuals36:33 Navigating Tax Forms and Returns37:27 Managing Investment Expectations38:37 Cash Flow and Tax Savings39:49 Evaluating Oil and Gas Investments41:15 Portfolio Diversification and Tax Planning43:15 Risk Management in Oil and Gas Investments53:09 Using IRAs and Roth Conversions01:03:01 Final Thoughts and Upcoming Events Hosted on Acast. See acast.com/privacy for more information.
• Jailbreaking you 401k: Investing Through Self-Directed IRAs & Solo 401ks 18.11.2025 54min

  📚 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/clubIn this episode, we delve into how new investors can unlock their retirement funds through self-directed IRAs and Solo 401ks. Learn about the transformation process, the role of custodians, and the potential to invest in real estate or other alternative investments. Our guest, Ted Damp from Advanta IRA, shares his expertise on unique investment strategies, partnering, commingling funds, and navigating IRS rules. We also discuss prohibited investments, transactions, and the unrelated business income tax (UBIT). Discover how to avoid common pitfalls, diversify your portfolio, and leverage your retirement funds effectively. Visit WealthElevator.com for more resources, including event information and vendor referrals.00:00 Unlocking Your 401k and IRA Funds01:05 Introduction to Self-Directed IRAs01:48 Meet Ted from Advanta IRA02:27 Understanding Partnering and Co-Mingling Funds05:41 Basic Rules and Prohibited Transactions09:21 Real-Life Self-Directed IRA Experiences13:36 Disqualified Persons and Entities23:45 Case Study: Partnering on a Real Estate Deal28:43 IRA Ownership and Expense Sharing29:25 Rules on Percentage Ownership30:36 Co-Mingling Funds for Investments32:59 Non-Recourse Loans Explained37:51 Partnering and Co-Mingling in Real Estate44:14 Alternative Investments and Syndications51:26 Final Thoughts and Contact Information Hosted on Acast. See acast.com/privacy for more information.