310 - The Pilot's Checklist That Built a $1 Billion Self Storage Empire
Release Date: 06/29/2026
Rock Bottom, Recovery, and the Red Hat: Larry Roberts on Losing Everything and Choosing Courage
Comfort To Courage
314 - Rock Bottom, Recovery, and the Red Hat: Larry Roberts on Losing Everything and Choosing Courage He had 12 years of sobriety, a thriving podcast production company, a recognizable personal brand, and a speaking career that put him on stages across the country. And then, quietly and completely, he lost all of it. In this episode of Comfort to Courage, Larry Roberts, founder of Red Hat Media and one of the most recognized voices in the podcasting world, pulls back the curtain on his very public and brutally honest battle with alcoholism, including multiple rehab stints, a DUI, a dissolved...
info_outline
313 - How Alpha Funding Gets Investors to the Closing Table Fast with Vance Josey
Comfort To Courage
You found the deal. You ran the numbers. And then you lost it to another investor because your lender couldn't get you a proof of funds letter over the weekend. If that scenario makes your stomach drop, this episode is about to change how you fund every deal from here on out. Jen sits down with her husband and business partner Vance Josey, real estate broker, general contractor, and hard money lending expert with Alpha Funding, to pull back the curtain on how investors actually get deals financed. Vance breaks down the difference between prequalification and underwriting, why speed matters...
info_outline
312 - She Left Caregiving to Build Luxury Memory Care Mansions with Nicole Becerra
Comfort To Courage
She watched residents cry alone on the floor, calls for help go unanswered, and a client ask her point blank, "Am I gonna die today?" That first shift as a professional caregiver didn't just break Nicole Becerra's heart. It gave her a mission. Instead of accepting that this was just how senior care worked, she asked a different question: what if it didn't have to be this way? In this episode, Nicole shares how she went from sitting bedside with dementia patients to acquiring raw land, navigating septic and zoning laws, and securing an SBA loan to build Mosaic Memory Care, a 16 room luxury...
info_outline
311 - Why This Investor Ditched Multifamily for Hot Springs and National Parks
Comfort To Courage
What if the smartest move in real estate right now isn't multifamily at all? While thousands of investors keep fighting over the same overpriced apartment deals, Zander Kemp walked away from 23 apartment buildings to chase something almost nobody else was building: luxury glamping and hot spring resorts parked right outside America's busiest national parks. In this episode, Zander, founder of Clear Summit Investments, breaks down exactly how he identified outdoor hospitality as a massively underpriced niche, still 90% owned by mom and pop operators, trading at cap rates nearly double what...
info_outline
310 - The Pilot's Checklist That Built a $1 Billion Self Storage Empire
Comfort To Courage
310 - From Airline Pilot to $1 Billion Self Storage Empire: Ryan Gibson's Blueprint for Passive Wealth What if the same checklist that keeps a commercial jet from crashing could also keep your real estate deals from blowing up your bank account? That is the mindset Ryan Gibson brought from the cockpit to the boardroom, and it is the difference between investors who build lasting wealth and those who get burned chasing the next shiny deal. In this episode, Ryan, president of Spartan Investment Group and co-host of Passive Income Pilots, breaks down the go or no-go framework he uses to...
info_outline
309 - From Addiction Recovery to 1,100 Lots: The Mobile Home Park Strategy Nobody Talks About with Tim Woodbridge
Comfort To Courage
309 - From $250K to $570K in 14 Months: How Tim Woodbridge Built a Mobile Home Park Empire Through Recovery and Resilience What if the deal everyone told you was bad turned out to be the foundation of an 1,100 lot portfolio? Tim Woodbridge bought his first mobile home park for $250,000 in 2019 with only 10 of 36 lots occupied. Experienced investors told him to walk away. Fourteen months later, after bringing in new homes and raising occupancy, that same property appraised for $570,000 and he returned every dollar of investor capital through a refinance. This episode is proof that your first...
info_outline
308 - He Lost 6 Figures as an LP and Then Became the Guy Who Vets the Operators
Comfort To Courage
308 - From 52 Houses to Fund Manager: How Tom St. John Built a Portfolio Powered by Discipline, Loss, and Unshakeable Due Diligence What happens when a single telescope changes everything? For Tom St. John, watching his father retire after 32 years at a power plant with nothing but a telescope as a gift was the moment that cracked his world open. That telescope became a symbol of what following the rules without building real assets actually gets you. Tom made a vow to find another way, and what followed was a decades-long journey through single-family rentals, multifamily acquisitions,...
info_outline
307 - No W-2? No Problem. The Invisible Prime Borrower Strategy Beating Traditional Lending
Comfort To Courage
307 - The Invisible Prime Borrower: How Efri Argaman Is Unlocking Homeownership for 42 Million Americans What if the biggest barrier to homeownership in America wasn't money, it was the wrong measuring stick? Right now, an estimated 37 to 42 million people in this country have the income to buy a home, pay their rent on time every single month, and are still being turned away by the traditional lending system simply because their income doesn't come with a W-2. That's not a credit problem. That's a broken system problem. And Efri Argaman, founder and CEO of OwnEZ, built a fintech company to...
info_outline
306 - The Doctor Who Walked Away from $500K a Year to Build $2 Billion in Real Estate
Comfort To Courage
What if everything you were taught about building wealth was designed for someone else's benefit, not yours? High-income professionals, especially doctors, lawyers, and entrepreneurs, are earning hundreds of thousands of dollars a year and still ending up financially behind, buried in debt, crushed by taxes, and handing their futures over to Wall Street. In this episode of the Real Estate Investor Growth Network, Jen Josey sits down with Buck Joffrey, MD, a former cosmetic surgeon turned serial entrepreneur who has been involved in over $2 billion in real estate transactions, to expose...
info_outline
305 - He Produced 60 Days In and Duck Dynasty and Now He's Teaching Real Estate Investors How to Be Impossible to Ignore
Comfort To Courage
What if the secret to dominating your real estate market had nothing to do with cash offers, fast closes, or undercutting your competition? Emmy-nominated television executive Brad Holcman spent 25 years in Hollywood making people impossible to ignore, and now he's revealing exactly how real estate investors can stop drowning in sameness, stand out in a crowded market, and become the only choice for motivated sellers. If your marketing sounds like everyone else's, this episode will change how you think about your brand forever. Brad introduces the powerful $2 Bill philosophy, the idea that...
info_outline310 - From Airline Pilot to $1 Billion Self Storage Empire: Ryan Gibson's Blueprint for Passive Wealth
What if the same checklist that keeps a commercial jet from crashing could also keep your real estate deals from blowing up your bank account? That is the mindset Ryan Gibson brought from the cockpit to the boardroom, and it is the difference between investors who build lasting wealth and those who get burned chasing the next shiny deal.
In this episode, Ryan, president of Spartan Investment Group and co-host of Passive Income Pilots, breaks down the go or no-go framework he uses to evaluate every deal, the same discipline that keeps an airplane in the sky. He shares the 10/30/30/30 principle for structuring your net worth, explains why self-storage has outperformed every other asset class over the last 40 years at roughly 17 percent annually, and reveals how Spartan grew from a single house flip with his neighbor turned business partner into a billion-dollar portfolio spanning 15 states and over seven million square feet. He also gets into the strategy behind converting old retail boxes, including a former Kmart and Macy's, into thriving storage facilities, plus the surprising real-world hazards that come with owning thousands of storage units.
This episode is essential listening for high-income professionals, especially airline pilots, who want true passive income without taking on a second job, as well as any real estate investor looking to diversify into a historically high-performing, recession-resistant asset class. If you have ever wondered how to evaluate a deal with the same clarity a pilot uses before takeoff, or whether self-storage deserves a spot in your portfolio, this conversation will change how you think about both.
5 Powerful Takeaways
- Learn the "extension clause" negotiating trick for 1031 exchanges that buys you extra time on the 45 and 180-day deadlines so you are never forced into a rushed, overpriced purchase.
- Discover the go/no go decision framework, borrowed directly from cockpit protocol, for knowing exactly when to walk away from a real estate deal and when you are too committed to turn back.
- Get the 10/30/30/30 net worth allocation strategy high-income earners use to balance liquidity, market growth, tax-advantaged real estate, and truly passive investments.
- Understand why self-storage has delivered roughly 17 percent average annual returns over 40 years, outperforming multifamily, data centers, and mobile home parks.
- Hear how a single house flip with a neighbor turned into a billion-dollar, 15-state self-storage portfolio, and what that growth story reveals about building investor trust early.
About the Guest
Ryan Gibson is a commercial airline pilot turned self-storage entrepreneur and president of Spartan Investment Group, now the 29th largest self-storage operator in the country with more than one billion dollars in capital organized across 15 states and over seven million square feet. He built Spartan alongside business partner and Army veteran Scott Lewis, growing the company from a single neighborhood flip into a major institutional-grade platform. Ryan also co-hosts the podcast Passive Income Pilots, where he teaches airline pilots and other high-income professionals how to build genuine passive income without adding a second job to their schedule. He applies the same disciplined, checklist-driven decision-making from his years in the cockpit to how he vets deals, operators, and markets today. More than 400 airline pilots have invested alongside him in Spartan's self-storage portfolio.
Resources & Websites Mentioned
- https://spartan-investors.com
- ryan@spartan-investors.com
- Passive Income Pilots podcast (available on iTunes, Stitcher, and YouTube)
Call to Action
To learn more about Jen Josey, visit https://www.therealjenjosey.com/
To join REIGN, visit https://www.reignmastermind.com/
Stuff Jen Josey Loves: https://www.reignmastermind.com/resources
Buy Jen Josey's Book: From Beginner to Badass: https://a.co/d/bstKlby
New episodes drop every Monday Morning at 6am EST. See you next time.