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The Wealth Elevator Podcast: Real Estate, Taxes, Investing
SPC074 - My Journey Back Home to Hawaii
My Journey Home:
Up to this point, my life has followed a steady, linear trajectory. But today... I took my own advise that time is your most important asset and I am happy to announce that I am speaking to you from Honolulu, Hawaii the new home base of Simple Passive Cashflow!
As a teenager growing up on a small island in the middle of the Pacific, I was programmed to go to college on the mainland because the cost of living in Hawaii was too high and jobs compensation was pretty poor. With the cost of living in Hawaii being 10% more than Seattle or San Francisco and 20% less pay for equivalent jobs, living a comfortable life is no easy feat. I resolved to never return unless I was extremely well off financially - although I am not where I want to be - I have the knowledge and network to get me where I need in the next few years.
Looking back on my path as a wide-eyed college student living away from my family for the first time in Seattle. And then started my Engineering career working for blood money for my first employer. I am a little dumbfounded how all that work through the traditional educational system only prepared me for a life as a worker-bee to save more and hopefully have enough after I gave away all that time during a 40 year career. But I do look back with gratitude since it gave me the means to save up for down payments and truly savour freedom when I achieve it.
I wanted to inspire others to “Burn The Boats”... to do what you want, where you want, and with whom you want - whether its buying that first rental, quitting a crappy job, getting away from a bad boss, starting a family, or just telling your mother in law to shut up.
Here are the 10 main reasons for my return to Hawaii and I hope you can find similarities to your journey:
1) It's a seller's market.
2) I don’t see many deals out in the market worthy of investing in. In fact, I can't find many that will make money. I don't believe in rent trends continuing upward. In my mind, that's called speculation.
3) Hawaii is a great place to hide out and chill. Knowing when to “hold’em” and when to “fold’em” is half the battle.
4) Environment matters. I used to live in a really affluent area in Kirkland and my Mercedes is seriously the crappiest car on the block. Homes are filled with babysitters watching kids as their parents play Bejewelled on their I-Phones. I just don’t feel like I fit in. Seattle also gets dark at 3:30 PM in the Seattle winter and I dislike being cold all of the time. Talk about Kurt Cobain! Shoot yourself in the head!
5) Embrace minimalism. My homeboy FI Fighter took the path of Extreme Financial Independence to race to a point where his income exceeded his expenses. At that point the plan is to escape the rat race which not only includes your job but the environment that contributes to lifestyle creep. On paper, Hawaii is one of the if not most expensive States to live in as evident with the median home costs of $800,000 and 8 dollar gallon of milk. The truth is in order to survive, Hawaii’s locals have to live frugally, in multiple generational households, and the housing stock/amenities is much lower quality (B tenant lives in a C building by US Mainland standards)… it's the price of paradise. From time to time we need to get back to basics and keep it simple.
6) A unique opportunity. One of my main goals is to create an investor network in Hawaii. People in Hawaii are very fiscally conservative and there is a lot of generational wealth passed on to younger generations. This creates a complex problem for people who have money and “don’t know how to fish.” My hope is to leverage the talents of others to create a non-profit financial education group based on the philanthropy of those who I will liberate from the rat race and will in turn help mentor others in basic personal financial education such as keeping a budget. If you are interested please reach out to me. The best companies are built on the foundations of culture and this is something I know everyone that comes to this website strongly believes in.
7) Technology bridges oceans. Some will say that I need to be close to the action, but I feel technology allows me to be everywhere at once. I travel to Texas and Atlanta a lot and they are major airport hubs which offer direct flights to HNL. I am also a cheap ass (which I am working to change :p), so I take the red-eye to avoid paying for a hotel that day. My situation will actually improve since instead of a 4 hour flight from Seattle to Texas, I now have a full 7 hour shut-eye flight from HNL to DFW.
8) Serve the people of Hawaii. You might be asking why am I still working? Check out this previous talk I gave explaining why you should not quit your job. I’ll be honest although, I work a few hours a day and times on the weekend on building SPC and my multi-family syndications I don’t have enough work to keep my busy all the time. I recently interviewed for a job and I told them that I was looking to work for good people who treated me fairly and with respect. For the past few years I only worked for non-private entities because I thought that they are one of those busy days at work... my efforts benefit at least the people and not a corporate entity. And now it's great that my work benefits the place I grew up. But don’t get me wrong here… I still don’t really enjoy the work I do and it is not Ikigai or the alignment for four items: 1) What you are good at, 2) What you Love, 3) What the world needs, 4) What you can be paid for.
9) Passion+Lifestyle=Happiness. Tom Corley (from Rich Habits) identifies 2 ways self-made millionaires rose from poverty or the middle-class. Either you live below your means and wisely invest your savings or you pursue something you are passionate about. I am achieving the best of both worlds. Yes, Hawaii is more expensive on paper, but it is easier to live a simple life and not get caught up in the perpetual pissing contest that many working professionals subconsciously partake in.
10) Retirement is a state of being. People wear Hawaiian Shirts on a vacation to feel relaxed. Why not make everyday like that? I am no where where I want to be but on my way. With a little Shave Ice too. I want my everyday life to feel like an indefinite vacation. #LuckyYouLiveHawaii
Live in the moment. Life is short… pull your head out off your butt before the years fly by. Don’t you see those Facebook memories posts and think where did the years go? The day is long and the years are short. Get up get out and get some. WUKAR! Lanikai Sunrise 😁 Check out the youTube Channel.
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534. Richard Duncan on Creditism, the AI Arms Race, and “Cognitism” | Macro Watch
49:03||Ep. 534📚 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 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 Duncan00:44 Macro Watch Discount01:03 From Gold to Creditism05:09 Why Old Theories Fail06:28 Credit Growth and 200808:31 COVID QE and Inflation10:54 Debt Wealth and AI Boom14:00 China AI Arms Race17:12 Energy Nuclear and Chips22:07 Stretched Valuations Risks31:58 Cognitism Explained37:36 AI Skills and Sectors41:13 What to Watch Next47:40 Wrap Up and SubscribeConnect 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.
533. Underwriting Games in Multifamily Deals: Cap Rates, IRR “Magic,” and Capital Stack Red Flags
26:31||Ep. 533📚 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 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 Setup00:42 Market Shift Overview01:21 Manufactured IRR Tricks03:32 Reversion Cap Rate Games04:22 Finding Real Cap Rates07:34 Rent Bumps Vs CapEx09:35 Discount Hype Reality10:48 Cap Rate Cycle Bets11:58 Debt Structure Risks13:24 Stacking Red Flags14:54 Preferred Equity Ahead17:23 Return Of Capital Trap19:11 DSCR And Fake Cashflow20:28 Cap Compression Review21:53 AI Deal Checklist24:52 Capital Stack Exceptions26:25 Final Q And WrapConnect 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.
532. Young Money with Jack Raines: How did it hack career growth for young professionals
52:02||Ep. 532📚 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 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 Secrets01:22 Meet Jack Raines03:01 Small Town to VC03:51 Entrepreneur Family Roots06:58 Prestige and Network09:49 Leaving the Southeast11:31 Target Schools Reality13:11 MBA as Golden Ticket15:04 Pedigree for Family Firms17:21 Spectrum of Wealth18:32 Rich vs Poor Options21:24 Capital and Quarters22:36 Merit and Social Circles25:39 Status Pressure on Rich27:19 High Achiever Burnout27:59 Pressure of Privilege29:03 Expectations and Happiness Gap30:18 New York Norms Shift31:39 Parents and Independence32:59 Stage Specific Living35:30 Funding Kids Choices37:59 Socioeconomic Marriage Friction43:01 Money Mindsets in Couples45:08 Young Money Plug47:25 FOOM Investing Lessons51:16 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.
531. Cost Segregation: Accelerate Depreciation & Unlock Tax Savings for Rental Property Investors
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530. Asset Protection for Accredited Investors: LLCs, Holding Companies, and Hybrid Trusts w Doug Lodmell
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529. 2026 Infinite Banking: How to Build Cash Value with Whole Life (90/10 vs 50/50) + Policy Loans
01:36:27||Ep. 529📚 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/clubThis 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 Overview01:21 Why Replace the Bank03:00 Whole Life vs Term04:41 Core Policy Benefits07:00 Loans and HELOC Analogy10:43 Emergency Fund and Protection11:28 Whole Life Scam Debate12:08 Premium Split Secret Sauce18:27 PUAs and MEC Limits22:32 How to Use the Policy30:49 Policy Illustration Break Even33:02 Flash Funding New Setup33:55 Choosing Carriers and Agents36:10 Riders Underwriting and Timing38:01 Advanced Triple Dip Ideas38:38 Leverage With Safe Assets39:13 Growth Years Deal Funding40:42 Liquidity Uses And Expenses41:13 Endgame Retirement And Protection41:48 Funding Options For New Investors42:34 Policy Loans Versus HELOC47:41 Accredited Investor Banking48:22 Courses Community And Trifecta51:13 Advanced Home Purchase Strategy53:12 Teaching Kids Controlled Debt54:22 Break Even And Policy Review55:43 Policy Design 10 90 Explained01:00:57 MEC Limits And Flexibility01:04:14 Costs Liquidity And Break Even01:06:44 Carrier Choice And 50 50 Compare01:09:23 Infinite Banking Fees01:11:01 Policy Design Levers01:11:52 Liquidity Versus Growth01:13:15 Best Use Cases01:20:21 Stacking Policies Strategy01:24:12 Buy Borrow Die Explained01:25:41 Loans Rates And Flexibility01:28:01 Break Even Benchmarks01:29:21 Windfall Funding Options01:31:13 Qualifying And Insurability01:32:52 Paid In Advance Premiums01:35:58 Final Thoughts 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.
528. Luxury Travel That’s Actually Worth It: How Travel Advisor Creates Seamless, Memorable Trips w/ David Axelrod beckonaire.com
50:34||Ep. 528📚 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/clubhttps://www.beckonaire.com/david@beckonaire.comThe 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 Matters01:05 Meet the Luxury Planner03:11 How Advisors Get Paid04:56 DIY vs Pro Planning06:24 What Luxury Costs09:49 Easy Luxury Upgrades14:50 When Luxury Is Not Worth It16:44 Boutique vs Big Brands18:49 How Pros Vet Hotels21:00 Choosing the Right Advisor24:42 Avoiding Instagram Traps28:20 Designing Meaningful Trips31:09 Thrill vs Comfort Balance37:32 Hands On Family Memories40:23 Exit Trips and Quick Getaways44:22 Travel Before You Cannot47:24 Travel as Time Investing49:29 Where to Find David50:10 Final Thanks and GoodbyeConnect 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.
527.5. I Got Into SpaceX Before the IPO. Here’s What Retail Investors Miss
14:23||Ep. 527.5📚 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.
527. Green Bay Football-Themed Airbnbs: PigskinJourneyman’s Short-Term Rental Business
46:36||Ep. 527📚 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.