The Wealth Elevator Podcast: Real Estate, Taxes, Investing

Lane Kawaoka, PE

🎓 Get free access to our 12-module Masterclass and start your journey today at TheWealthElevator.com/master. The Wealth Elevator is your ultimate guide to financial freedom. From my humble beginnings buying small rental properties in 2009 as an W2 working engineer to becoming a general partner in over $2.1 billion in assets, we reveal the three-step wealth-building system, covering: 🚀 Alternative investments to diversify your portfolio 💰 Tax income strategies for financial independence 🏦 Infinite banking to maximize your wealth Join our community and get access to our free Masterclass - theWealthElevator.com/club Welcome to those who found us through the new book! Welcome to our Ohana! Hosted on Acast. See acast.com/privacy for more information.

  1. Green Bay Football-Themed Airbnbs: PigskinJourneyman’s Short-Term Rental Business

    2d ago

    Green Bay Football-Themed Airbnbs: PigskinJourneyman’s Short-Term Rental Business

    📚 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.

    47 min
  2. How Business Owners Use ESOPs to Reduce Taxes on an Exit w/ Vistage Speaker Steven Nicokiris

    May 26

    How Business Owners Use ESOPs to Reduce Taxes on an Exit w/ Vistage Speaker Steven Nicokiris

    📚 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.

    50 min
  3. The Sandwich Generation: aging parents and raising kids

    May 12

    The Sandwich Generation: aging parents and raising kids

    📚 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.

    12 min
  4. Infinite Banking: 10/90 vs 50/50 Whole Life Policy, Cash Value, MEC Limits & Break-Even

    Apr 28

    Infinite Banking: 10/90 vs 50/50 Whole Life Policy, Cash Value, MEC Limits & Break-Even

    📚 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.

    42 min
  5. Apr 14

    Growth Focus Finder Panel: Family Office Deal Flow, AI Underwriting & Real Estate Structures

    📚 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.

    7 min
  6. Self-Directed IRA vs Solo 401(k): Checkbook Control, Prohibited Transactions, and UBIT/UDFI Explained

    Mar 31

    Self-Directed IRA vs Solo 401(k): Checkbook Control, Prohibited Transactions, and UBIT/UDFI Explained

    📚 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 Self-Directed IRA vs Solo 401(k): Checkbook Control, Prohibited Transactions, and UBIT/UDFI Explained Lane 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 Direction 01:00 Solo 401k Eligibility 02:33 Why Big Brokers Fail 06:38 Checkbook Control Basics 09:13 IRA Trust Option 11:03 Solo 401k Advantages 13:13 SDIRA Setup and Funding 13:54 Custodian vs Control 20:46 Prohibited Assets Rules 23:04 Disqualified Individuals 25:28 UBIT and UDFI Taxes 28:25 UDFI Real Estate Example 31:26 Solo 401k Tax Exemption 33:47 Solo 401k Setup Details 36:18 Solo 401k Loan Feature 37:00 Plan Rules vs IRS 38:46 Contribution Limits Explained 42:13 Loan Terms and Repayment 43:28 Roth and Backdoor Strategies 46:43 Paying Kids and Audits 47:58 Punting Taxes with QRP 51:02 Setup Timeline and Funding 54:18 Checkbook Control Custodians 58:25 When QRP Investing Makes Sense 01:04:37 Retirement Tax Trap Parents 01:06:26 Parents Money Risk Choices 01:07:24 How Much to Retire 01:08:54 Stop Overfunding 401k 01:10:32 Back Into 4 Percent Rule 01:13:47 Financial Independence Mindset 01:14:53 Three Bucket Strategy 01:16:51 Kids Inheritance Limits 01:19:28 UBIT Surprise in Solo 401k 01:21:29 Blocker Corps and AI Learning 01:24:10 Finding the Right Tax Pro 01:28:17 Trivia and Wrap Up 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.

    1h 29m
  7. Mar 17

    2026 Mortgage Rate Update: What’s Happening with Rates, Treasuries, DSCR Loans, and Investor Lending (with Jen Hernandez)

    📚 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 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 Snapshot 00:49 Rates After 2020 02:22 Tracking Rates Like Pros 04:12 Fed vs Treasury Explained 08:22 Buy Now or Wait 12:19 DSCR Loans and Down Payments 16:50 Appraisals and Rent Data 19:15 Direct Lenders vs Brokers 23:31 Reserves and Credit Prep 27:38 How Wealthy Buyers Finance 30:44 Wrap Up and Contact Info Hosted on Acast. See acast.com/privacy for more information.

    32 min
  8. Mar 3

    Tax-Free Gains: QSBS for Startup Investments

    📚 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 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 Startups 00:28 Meet the Expert: CPA Thomas Jones 01:04 Understanding QSBS: Qualified Small Business Stock 03:15 Industries and Use Cases for QSBS 06:34 Asset vs. Stock Sales: Key Differences 12:09 Investor Considerations and Tax Benefits 25:00 Advanced Strategies and Pitfalls 35:24 Conclusion and Contact Information 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.

    37 min
4.9
out of 5
461 Ratings

About

🎓 Get free access to our 12-module Masterclass and start your journey today at TheWealthElevator.com/master. The Wealth Elevator is your ultimate guide to financial freedom. From my humble beginnings buying small rental properties in 2009 as an W2 working engineer to becoming a general partner in over $2.1 billion in assets, we reveal the three-step wealth-building system, covering: 🚀 Alternative investments to diversify your portfolio 💰 Tax income strategies for financial independence 🏦 Infinite banking to maximize your wealth Join our community and get access to our free Masterclass - theWealthElevator.com/club Welcome to those who found us through the new book! Welcome to our Ohana! Hosted on Acast. See acast.com/privacy for more information.

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