The Wealth Elevator Podcast: Real Estate, Taxes, Investing cover art

The Wealth Elevator Podcast: Real Estate, Taxes, Investing

The Wealth Elevator Podcast: Real Estate, Taxes, Investing

By: Lane Kawaoka PE
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🎓 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


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Career Success Economics Personal Finance
Episodes
  • I Got Into SpaceX Before the IPO. Here’s What Retail Investors Miss
    Jun 13 2026
    📚 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.
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    14 mins
  • Green Bay Football-Themed Airbnbs: PigskinJourneyman’s Short-Term Rental Business
    Jun 9 2026

    📚 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.

    Show More Show Less
    47 mins
  • How Business Owners Use ESOPs to Reduce Taxes on an Exit w/ Vistage Speaker Steven Nicokiris
    May 26 2026

    📚 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.

    Show More Show Less
    50 mins
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