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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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More info: https://drive.google.com/open?id=0B4gFjCt6Knc1U3YwYjdZRnYzN1k
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529. 2026 Infinite Banking: How to Build Cash Value with Whole Life (90/10 vs 50/50) + Policy Loans
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528. Luxury Travel That’s Actually Worth It: How Travel Advisor Creates Seamless, Memorable Trips w/ David Axelrod beckonaire.com
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527.5. I Got Into SpaceX Before the IPO. Here’s What Retail Investors Miss
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527. Green Bay Football-Themed Airbnbs: PigskinJourneyman’s Short-Term Rental Business
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526. How Business Owners Use ESOPs to Reduce Taxes on an Exit w/ Vistage Speaker Steven Nicokiris
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525. The Sandwich Generation: aging parents and raising kids
11:48||Ep. 525📚 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 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 Intro01:21 Meet the Caregiver Cheryl02:30 Estate Planning Pitfalls04:09 Money Choices Under Pressure05:40 Wealth Building to Preservation06:19 Post Sandwich Investing07:25 Fear of Taking Risks09:04 Testing Alternatives Slowly10:01 You Are Not Alone11:08 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.
524. Infinite Banking: 10/90 vs 50/50 Whole Life Policy, Cash Value, MEC Limits & Break-Even
42:15||Ep. 524📚 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 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 Hook00:29 Infinite Banking Basics01:31 Designing a 10 90 Policy04:39 Minimums Maximums and MEC09:02 Choosing Carriers Wisely10:03 Year One Cost and Break Even14:44 10 90 vs 50 50 Comparison19:04 Use Cases and Strategy Fit22:10 High Net Worth Use Cases23:07 Parents Funding Kids Policies23:58 Early Access And Loan Cycling24:49 Comparing Container Size26:10 One Policy Or Stack26:36 Agent Incentives And Fees30:00 Buy Borrow Die Explained31:27 Policy Loans Versus HELOC33:50 Breakeven And Flexibility35:10 Windfall Funding Strategies37:02 Qualifying And Insurability38:41 Paid In Advance Premiums40:53 Start Early And Use Spouses41:47 Wrap Up 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.
523. Growth Focus Finder Panel: Family Office Deal Flow, AI Underwriting & Real Estate Structures
07:01||Ep. 523📚 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 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 Kickoff00:27 Lane Kawaoka Intro01:33 Contrarian Investing Approach03:11 Creative Deal Structures04:20 AI Underwriting Workflow05:29 Million Dollar Insight06:49 Audience Q&A 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.