📚 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.

📚 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.

📚 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.

📚 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.

📚 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.

📚 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.

📚 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.