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/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.

📚 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.

📚 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.

📚 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.

📚 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.