High Income, No Tax Advantage: The Wealth Problem Pilots and High Earners Need to Solve w/ Ryan Gibson
Release Date: 08/13/2026
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Most people think the hard part is making money. But Lawrence Dunning’s story shows that making money, keeping money, and using money well are three very different things. By 30, Lawrence had built a multi-million-dollar net worth on the trading floor in Chicago. Then he stepped away to pursue a dream that had a much smaller window: becoming a professional MMA fighter. When he came back, the trading business model that had made him wealthy had changed, and the income stream he once relied on was gone. In this episode of Money School Elite, I sit down with Lawrence to talk about what he...
info_outlineMost high-income W-2 earners eventually run into the same problem.
Their income gets better, but their structure does not.
Airline pilots are one of the clearest examples. They can earn exceptional money, receive strong retirement contributions, and build what looks like a very successful financial life on paper. But as the income grows, so does the constraint: almost all of it is active, highly taxable, and tied to a system that gives them very few levers to pull.
And pilots are not the only ones facing this. Doctors, executives, engineers, senior tech employees, corporate leaders, and employees sitting on major equity events can all end up in the same position. A big salary, bonus, liquidity event, or IPO can create life-changing income, but if that income is still flowing through a W-2 structure, the tax problem does not disappear. In many cases, it becomes more obvious.
In this episode of Money School Elite, I sit down with Ryan Gibson, former airline pilot and co-founder of Spartan Investment Group, to talk about the difference between earning more money and changing the facts of your financial life.
Ryan spent 17 years as an airline pilot before building a self-storage company with 90 facilities, roughly 7.5 million square feet, and about 200 employees. He understands the high-income W-2 problem because he lived it, and his perspective goes beyond simply making more, saving more, or maxing out retirement accounts.
We get into why pilots and other high earners often pay more in taxes as their income rises, how strong retirement contributions should change the way they think about excess cash flow, why ownership opens up tax advantages employees often cannot access, and how self-storage can give investors exposure to real estate without buying themselves another job.
This is not really a conversation about pilots, and it is not only about self-storage. It is about how high-income earners can turn income into structure, ownership, cash flow, tax efficiency, and long-term financial control.
About the Guest
Ryan Gibson is the Co-Founder, President, and Chief Investment Officer of Spartan Investment Group, a commercial real estate firm focused on self-storage and private real estate investment opportunities.
A former airline pilot with 17 years of active flying experience, Ryan brings a unique perspective to wealth-building for high-income W-2 professionals, especially pilots who are earning high incomes but often facing significant tax challenges. Through Spartan Investment Group, he helps individual investors access private real estate opportunities designed to create diversification, cash flow, tax advantages, and long-term wealth outside the traditional W-2 and 401(k) framework.
Spartan has grown into a national self-storage platform with 90 facilities, roughly 7.5 million square feet, and approximately 200 employees. Ryan’s real estate experience spans residential development, self-storage, infill development, finance, sales, marketing, investor relations, tax foreclosures, inherited homes and estates, and real estate syndication. He is also the co-founder of Passive Income Pilots, a platform and podcast that educates pilots and other high-income professionals on passive investing, tax strategy, real estate, and building wealth beyond the paycheck.
Spartan Investment Group: spartan-investors.com
Join the Free Academy: [email protected]
Passive Income Pilots Podcast: https://passiveincomepilots.com/
Ryan Gibson on LinkedIn: https://www.linkedin.com/in/ryan-gibson1/
About Your Host
From pro-snowboarder to money mogul, Chris Naugle has dedicated his life to being America’s #1 Money Mentor. With a core belief that success is built not by the resources you have, but by how resourceful you can be. Chris has built and owned 19 companies, with his businesses being featured in Forbes, ABC, House Hunters, and his very own HGTV pilot in 2018. He is the founder of The Money School™ and Money Mentor for The Money Multiplier.
His success also includes managing tens of millions of dollars in assets in the financial services and advisory industry and in real estate transactions. As an innovator and visionary in wealth-building and real estate, he empowers entrepreneurs, business owners, and real estate investors with the knowledge of how money works.
Chris is also a nationally recognized speaker, author, and podcast host. He has spoken to and taught over ten thousand Americans, delivering the financial knowledge that fuels lasting freedom.
Resources
Private Money Guide: https://go.moneyschoolrei.com/book-podcast
Wealth Wednesday Webinar: https://go.moneyschoolrei.com/wednesday-webinar-podcast
Mapping out the Millionaire Mystery: https://go.moneyschoolrei.com/newbook-podcast