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The Wealth Elevator Podcast: Real Estate, Taxes, Investing
SPC080 - Moving from Single Family to Multifamily Investing
Hey guys I’m about to get naked here… I am personally making a shift in my portfolio to MFH syndications and wanted to see if you could help me find a buyer for my stabilized 10 property 1.2M portfolio.. 10 B Class properties in Birmingham/Atlanta/Indy (rents $900+/month)
I have selected a few potential turnkey rental sellers, however, I wanted to leverage my network and see if we can cut the broker commissions out of it. I’ll give you details on how you can get the P&L for the past few years on every property but first...A few PSAs.
- National Save for Retirement Week: October 15 – 21, 2017
- Scam emails to get information from more and more wholesalers
- Insurance want 5% deductible
My story - bought a couple of rentals in Seattle and 1031 exchange those to 10 SFH essentially turnkey rentals out of state in Atlanta, Birmingham, Indianapolis.
The other day I asked the question on BP… did not get much of a response since BP is a platform for newbies or active investors who flip or wholesale homes. SPC is a platform with secret Facebook groups of profession W2 employees with some cash and little time on their hands.
As I talked a few podcasts ago of a 10k repair, and multiple other headaches, my attitude for these SFHs are changing. Its kind of funny talking to the many of you that are setting up calls to get on the Hui Deal Pipeline Club to getting sent the deals I come across:
https://simplepassivecashflow.activehosted.com/f/3
Please go through the first 20 podcasts in early 2016 and love the story of this SFH buyer but then they are like WTF you are turning on us like a villain going to MFH.
"Find me an investor who has 50 SFHs and I will show you an investor who was invested under a rock and stoned himself to death with said rock" -Archimedes
After over a few hundred investor consultants over the past couple years here is what I tell W2 employees. For those who are able to save more than $30k a year or have substantial liquidity (over 200k), being a landlord and especially flipping is a lot of work. If you like it cool... but just remember why we got into this... To be free from a JOB. Directly investing in a turnkey rental or small MFH is a good way to start to learn and build up the war chest to go into my scaleable investments such as private placement syndications. Whatever you do, try to be as close to the investment as possible. This is the fundamental problem I have with Wall Street who takes too much fees off the hard working efforts of the middle class.
The straw that broke the camels back...
One of my Atlanta properties went over a changeover, tenant went MIA, went through process to evict - always start the time clock. Armed sheriff had to go and remove items on the street, dead cats were found, $5000 just to remove items, concern over the property could have been condemned. I got Proserve out of Atlanta to go in with radiation suits to clean it up, got a bill for $27K, wtf, some of the scope items were a little ridiculous like 500 dollars for gutters, 5000 for paint, and siding etc. I had them re-estimate it to give me the "dude I'm not a rich idiot price and got it lowered to 20K.
There is no such thing as turnkey. Check out these disaster photos… https://photos.app.goo.gl/R4PZLuOLGHONO5Rl2
Tony Robbins says “Things don't happen to you but for you.”
This was a sign from above which many of you guys hear from me that I sort of believe in. I was already mentally making the shift to making the move. Going down the quote from the repair company it was clear that a lot of the scope items were a bit excessive and the pricing was inflated. This was to be expected, for example paint on rooms that did not really need painting for $5000 or new gutters cleaning for $500.
If you want to see this document. Please leave me an iTunes review or send me an email referral to a friend and i'll send it over. Lane@SimplePassiveCashflow.com
Stages of trauma… denial, anger, sadness, motivation.
What I know now I am able to now only make a high yield but a fraction of the effort. None of this screwing around sending docs to my lender in the evenings for a couple months to get one dinky SFH to cash flow a couple hundred dollars a month then do it all over again 20-50 times… then to have it all taken away with a large capex or turnover repair.
Tony Robbins says “You destiny is shaped in your decisions.”
We waste so much time making decisions. A lot of people myself included get shiny object syndrome when really its an excuse.
This was my hero moment or burning of the boats moment to leave the security of a few thousand of passive cashflow a month to go liquid for a while. Hopefully Amazon will announce that Atlanta will be the new second HQ on their quest for world domination.
One drawback about selling is about repaying a lot of depreciation recapture and capital gains going back all the way from 2009. As you remember I traded my two Seattle properties for the majority of these rentals via a 1031 exchange. This is why I am not a fan of a 1031 exchange no matter what you hear on a surface level on other podcasts. Another reason to keep listening and please do me a favor and share it with friends because we go deep on this stuff because I’m learning everyday. I’ll repeat I don’t like 1031 exchanges because many of us are going to graduate in large syndications and that is not a like kind exchange. Executing a 1031 most likely means you are going into a lukewarm deal and lose all your negotiation power as a buyer. But i'll expand on this at a later date.
Picture of my back of envelope tax hit
I want to be very clear… If you are not an accredited investor, sophisticated, or have a large sum of liquify... single family homes is the starting point for you. Too many call me with lofty goals and have list of pro’s/con’s of MFH vs SFH, but you need to know the basics before you screw up the big stuff. You have to pay your dues. Set that barrier to entry lower because most people won’t do anything.
That said for a limited time I invite you listeners to make offers on my portfolio of SFHs “Lane’s Pac-10”. List price is 1.2M right about 1% Rent-to-Value Ratio (More info -http://simplepassivecashflow.com/podcast-3-rent-to-value-ratio/). Will need you to make sure you sign up for my Hui Deal Pipeline Club:
https://simplepassivecashflow.activehosted.com/f/3
I figure it was only fair if I showed you my naked photos… I mean P&Ls that you take a few minutes to complete a form with your investor profile on.
And if you are listening to this after 2017 and would like to see how frequency of rental checks, vacancy, late payments, repairs, cap ex across all my properties please leave me an iTunes review or send me an email referral to a friend and i'll send it over.Lane@SimplePassiveCashflow.com
Mastermind Club: If you or someone you refer invests at least $50K into one of my future deals you will be invited to my exclusive Ali'i Mastermind with other 12-20 other serious investors to discuss deals and our own portfolios.
Check out my Free Resources Below:
1) If you are an accredited investor and afraid of the impending market correction?Get out the stock market and into the Simple Passive Cashflow Hedge Fund!
More info: www.SimplePassiveCashflow.com/fund
2) Join a Social Club:
3) Subscribe to my podcast: Google Android Phones | Apple iPhone | Youtube
4) Once you have gone through the majority of podcasts feel free to sign up for a chat:
5) Make sure you sign up for my Hui Deal Pipeline Club to get sent the deals I come across.
6) I am partnered with a start-up Virtual Assistant firm out in the Philippines. Shoot me an email Lane@simplepassivecashflow.com if you want to try them out.
More info: https://drive.google.com/open?id=0B4gFjCt6Knc1U3YwYjdZRnYzN1k
7) Please leave a review for the podcast!
8) Coaching Program to get you to your first rental in 90 days!
9) And finally... if you are just getting started Sign-up for Free access to the 10 Module Course:
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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
39:30||Ep. 531Do a cost seg go to theWealthElevator.com/costsegLane 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 Picture00:56 Retreat And Webinar Intro02:15 Lunch And Learn Setup03:37 Cost Seg Basics Explained06:27 Bonus Depreciation And CPA Fit09:39 Not A Loophole History17:35 Who Benefits And Pricing21:11 Fast DIY Process Walkthrough23:26 Audit Risk And Support28:01 Timing And Catch Up Rules30:24 Q And A Recapture Value38:39 Wrap Up And Next Steps
530. Asset Protection for Accredited Investors: LLCs, Holding Companies, and Hybrid Trusts w Doug Lodmell
55:30||Ep. 530📚 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/clubIn 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 Shield00:35 Webinar Setup01:18 LLCs and Liability Types02:57 Why Passive LPs Win04:21 Building a Holding Structure07:28 Best States for Entities09:20 How Many Properties per LLC13:45 Siloing LP Interests18:02 Dirty Assets and Side Silos20:25 Doctor Lawsuit Scenario21:40 Single Member LLC Tax Simplicity23:55 Trust Layer and Collection Defense27:03 Discovery Costs Reality27:48 Settlement Leverage Assets30:21 Negotiation Trump Card34:15 Trust Options Offshore38:04 Bridge Trust Sweet Spot40:57 Layering LLCs Over Time42:10 Insurance And Homestead47:24 Crypto Placement Protection49:17 Finding Hidden Crypto51:30 Avoid Tax Trust Scams55:12 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.
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.