📚 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 interviews economist Richard Duncan (author of The Dollar Crisis and The Money Revolution and publisher of Macro Watch) about how ending the gold standard in 1971 shifted capitalism into “creditism,” enabling massive US trade deficits, disinflation, falling rates, and explosive growth in debt and Fed balance sheet expansion that prevented depressions in 2008 and during COVID. Duncan contrasts post-2008 low inflation with post-COVID inflation driven by supply-chain blockages, and argues credit-driven liquidity has inflated asset valuations while accelerating AI breakthroughs and fueling China’s rise via persistent US deficits. They discuss the US–China AI and defense race, energy and nuclear power needs, and risks from higher inflation and rates amid stretched valuations. Duncan introduces “cognitism,” a coming system driven by exponentially expanding AI intelligence, and highlights sectors tied to AI, semiconductors, energy, data centers, robotics, and defense, plus key macro indicators to watch.

00:00 Meet Richard Duncan

00:44 Macro Watch Discount

01:03 From Gold to Creditism

05:09 Why Old Theories Fail

06:28 Credit Growth and 2008

08:31 COVID QE and Inflation

10:54 Debt Wealth and AI Boom

14:00 China AI Arms Race

17:12 Energy Nuclear and Chips

22:07 Stretched Valuations Risks

31:58 Cognitism Explained

37:36 AI Skills and Sectors

41:13 What to Watch Next

47:40 Wrap Up and Subscribe

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 speaker reviews real-life (anonymized) multifamily deal examples to help investors spot misleading underwriting and marketing tactics. Key topics include “manufactured” IRR boosts from aggressive refinance assumptions, unrealistic exit/reversion cap rates (and the difficulty LPs have validating prevailing market cap rates), and mismatches between large CapEx plans and modest rent-bump projections that may signal weak market fundamentals or hidden reserves. They discuss how cap rate compression can inflate paper returns despite being uncontrollable, why comparing discounts to 2021 pricing can be irrelevant, and how debt structure (fixed vs floating, term length, IO, extensions, prepayment penalties) affects refinance and exit risk. Additional red flags include preferred equity ahead of common equity, side-letter complications in the capital stack, and early distributions funded from reserves rather than operations, which can mask weak DSCR.

00:00 Cap Rate Question Setup

00:42 Market Shift Overview

01:21 Manufactured IRR Tricks

03:32 Reversion Cap Rate Games

04:22 Finding Real Cap Rates

07:34 Rent Bumps Vs CapEx

09:35 Discount Hype Reality

10:48 Cap Rate Cycle Bets

11:58 Debt Structure Risks

13:24 Stacking Red Flags

14:54 Preferred Equity Ahead

17:23 Return Of Capital Trap

19:11 DSCR And Fake Cashflow

20:28 Cap Compression Review

21:53 AI Deal Checklist

24:52 Capital Stack Exceptions

26:25 Final Q And 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

The episode features Jack Raines, author of “Young Money,” discussing how growing up with money provides insider knowledge about elite career paths, target schools, networks, and promotion moves that can lead to high incomes, while students from poorer backgrounds often must choose safer banking or consulting roles to repay large loans and can’t take startup risks. Raines shares his own path from South Georgia and Mercer University football to Columbia Business School and venture capital, emphasizing education, early “prestige stamps,” and intentional living that matches life stages. The conversation explores status pressure on wealthy kids, anxiety and expectations in elite environments, and how socioeconomic differences can complicate relationships and marriage. It closes with Raines promoting his book and the host warning investors to avoid inexperienced operators by relying on trusted networks and semi-institutional sponsors.

00:00 Money Game Secrets

01:22 Meet Jack Raines

03:01 Small Town to VC

03:51 Entrepreneur Family Roots

06:58 Prestige and Network

09:49 Leaving the Southeast

11:31 Target Schools Reality

13:11 MBA as Golden Ticket

15:04 Pedigree for Family Firms

17:21 Spectrum of Wealth

18:32 Rich vs Poor Options

21:24 Capital and Quarters

22:36 Merit and Social Circles

25:39 Status Pressure on Rich

27:19 High Achiever Burnout

27:59 Pressure of Privilege

29:03 Expectations and Happiness Gap

30:18 New York Norms Shift

31:39 Parents and Independence

32:59 Stage Specific Living

35:30 Funding Kids Choices

37:59 Socioeconomic Marriage Friction

43:01 Money Mindsets in Couples

45:08 Young Money Plug

47:25 FOOM Investing Lessons

51:16 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.

Do a cost seg go to theWealthElevator.com/costseg

Lane hosts a monthly investor “lunch and learn” webinar replay on cost segregation with guest AJ Lyons of DIY Cost Seg, explaining how cost seg reclassifies non-structural property components into shorter 5- and 15-year lives to accelerate depreciation versus standard 27.5-year (residential) or 39-year (commercial) schedules, often pulling a significant portion of deductions into year one, especially when 100% bonus depreciation applies. They discuss who benefits (rental owners, short-term rentals, commercial, value-add renovations), timing (including doing studies after purchase via amended returns or Form 3115), CPA coordination, potential use cases like short-term rental material participation or real estate professional status, depreciation recapture considerations, pricing and fast report delivery, and audit defensibility and optional audit support. Lane also announces an accredited investor retreat Jan 15–17, 2027 and directs viewers to thewealthelevator.com/costseg and related resources.

00:00 Depreciation Big Picture

00:56 Retreat And Webinar Intro

02:15 Lunch And Learn Setup

03:37 Cost Seg Basics Explained

06:27 Bonus Depreciation And CPA Fit

09:39 Not A Loophole History

17:35 Who Benefits And Pricing

21:11 Fast DIY Process Walkthrough

23:26 Audit Risk And Support

28:01 Timing And Catch Up Rules

30:24 Q And A Recapture Value

38:39 Wrap Up And Next Steps

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

In this webinar, asset protection attorney Douglass Lodmell explains how investors and high-liability professionals should structure entities to reduce exposure, contrasting inside vs. outside liability and why LLCs are commonly used to hold rental properties. He discusses when to silo “dirty” assets like rentals and operating businesses, noting janitorial or similar high-risk businesses are typically kept separate and often run as an LLC taxed as an S-corp, while safer assets (brokerage accounts, stocks/bonds, many LP interests) can sit under a holding company such as an asset management limited partnership (AMLP). Lomel gives a rule-of-thumb of roughly $250k–$500k equity per rental-property LLC and emphasizes insurance as the primary defense. He explains why passive LP investors generally have no personal liability beyond their investment, outlines jurisdiction choices for LLCs vs. holding companies, and details adding an asset protection trust—favoring a hybrid “bridge trust” that can convert offshore if needed—along with considerations for homes, life insurance, crypto, and avoiding fraudulent transfers and tax-scheme promoters.

00:00 LP Liability Shield

00:35 Webinar Setup

01:18 LLCs and Liability Types

02:57 Why Passive LPs Win

04:21 Building a Holding Structure

07:28 Best States for Entities

09:20 How Many Properties per LLC

13:45 Siloing LP Interests

18:02 Dirty Assets and Side Silos

20:25 Doctor Lawsuit Scenario

21:40 Single Member LLC Tax Simplicity

23:55 Trust Layer and Collection Defense

27:03 Discovery Costs Reality

27:48 Settlement Leverage Assets

30:21 Negotiation Trump Card

34:15 Trust Options Offshore

38:04 Bridge Trust Sweet Spot

40:57 Layering LLCs Over Time

42:10 Insurance And Homestead

47:24 Crypto Placement Protection

49:17 Finding Hidden Crypto

51:30 Avoid Tax Trust Scams

55:12 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

This webinar introduces infinite banking/accredited investor banking using properly designed whole life insurance as a liquid, asset-protected “cash value” tool that can be borrowed against to invest while the full cash value continues to grow. The presenter explains why configuration matters—minimizing the insurance/base premium (often ~10%) and maximizing paid-up additions (PUAs ~90%) to reduce fees and commissions, improve early liquidity, and reach a faster break-even point. It contrasts a 90/10 design versus a 50/50 design, discusses dividends, tax-free loans/withdrawals, MEC limits, underwriting, policy loan rates (~4–6%), and use cases such as funding deals, emergency reserves, education funding, retirement income, mortgage payoff decisions, and legacy planning. A licensed, non-captive agent joins to explain illustrations, funding flexibility, and scenarios like “flash funding” after liquidity events.

00:00 Infinite Banking Overview

01:21 Why Replace the Bank

03:00 Whole Life vs Term

04:41 Core Policy Benefits

07:00 Loans and HELOC Analogy

10:43 Emergency Fund and Protection

11:28 Whole Life Scam Debate

12:08 Premium Split Secret Sauce

18:27 PUAs and MEC Limits

22:32 How to Use the Policy

30:49 Policy Illustration Break Even

33:02 Flash Funding New Setup

33:55 Choosing Carriers and Agents

36:10 Riders Underwriting and Timing

38:01 Advanced Triple Dip Ideas

38:38 Leverage With Safe Assets

39:13 Growth Years Deal Funding

40:42 Liquidity Uses And Expenses

41:13 Endgame Retirement And Protection

41:48 Funding Options For New Investors

42:34 Policy Loans Versus HELOC

47:41 Accredited Investor Banking

48:22 Courses Community And Trifecta

51:13 Advanced Home Purchase Strategy

53:12 Teaching Kids Controlled Debt

54:22 Break Even And Policy Review

55:43 Policy Design 10 90 Explained

01:00:57 MEC Limits And Flexibility

01:04:14 Costs Liquidity And Break Even

01:06:44 Carrier Choice And 50 50 Compare

01:09:23 Infinite Banking Fees

01:11:01 Policy Design Levers

01:11:52 Liquidity Versus Growth

01:13:15 Best Use Cases

01:20:21 Stacking Policies Strategy

01:24:12 Buy Borrow Die Explained

01:25:41 Loans Rates And Flexibility

01:28:01 Break Even Benchmarks

01:29:21 Windfall Funding Options

01:31:13 Qualifying And Insurability

01:32:52 Paid In Advance Premiums

01:35:58 Final Thoughts 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

https://www.beckonaire.com/

[email protected]

The host shifts from investing to spending on experiences through travel, referencing Bill Perkins’ idea of trading money for memories, especially after 40. He interviews David from Beckonaire, who designs bespoke luxury trips—hotels, villas, yacht charters, private tours, and complex logistics—explaining that travel advisors are typically paid commissions by hotels and can add perks like credits and upgrades without costing clients more. David argues advisors reduce risk and friction across transitions (transfers, visas, timing) and become essential as trip spend rises. They discuss typical five-star costs for a family of four, where luxury isn’t worth it (overpriced hotels and buzzworthy destinations), the value of boutique hotels, and examples of upgrades like meet-and-greet services, private boats, and special experiences. David emphasizes upfront conversations, rapport, and long-term “leisure time” planning across life stages.

00:00 Why Travel Matters

01:05 Meet the Luxury Planner

03:11 How Advisors Get Paid

04:56 DIY vs Pro Planning

06:24 What Luxury Costs

09:49 Easy Luxury Upgrades

14:50 When Luxury Is Not Worth It

16:44 Boutique vs Big Brands

18:49 How Pros Vet Hotels

21:00 Choosing the Right Advisor

24:42 Avoiding Instagram Traps

28:20 Designing Meaningful Trips

31:09 Thrill vs Comfort Balance

37:32 Hands On Family Memories

40:23 Exit Trips and Quick Getaways

44:22 Travel Before You Cannot

47:24 Travel as Time Investing

49:29 Where to Find David

50:10 Final Thanks and Goodbye

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 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 Hype

01:22 Primary vs Secondary Markets

02:47 Pre IPO Round Explained

03:43 IPO Pops and Pullbacks

04:58 Why SpaceX Wins Long Term

05:51 Elon as Capital Raiser

07:17 Building the Rails Analogy

08:48 My Investing Origin Story

09:58 How to Access Pre IPO Shares

13:05 Risks and Final Thoughts

13:51 Q&A and Book Plug

Connect 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/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.