EP282 How to Become Financially Free by Holding Forever with Jonathan Barr

EP282 How to Become Financially Free by Holding Forever with Jonathan Barr

My guest today believes that Holding Forever is the best way to become Financially Free.

Jonathan Barr grew up in a real estate family and started investing after the Great Recession. He's completed Higher-End Single Family Flips, Ground Up Developments, and Multi-Family Repositions with his brother through their company JB2 Investments.

Today we're also going to talk about Fix & Flipping V.S. Multi-Family and Jonathan's investment strategy that has generated over 22 Million in profits with an average yearly return of 38%. We're also going to discuss the tax ramifications of both strategies, including cost segregation reports, depreciation, and the "Real Estate Professional" status.

Jonathan will also share details on the townhome development project he initiated in Los Angeles, and how it's taken over five years to break ground. We'll discuss the 1031 exchange he completed by selling a Los Angeles duplex in order to buy a 14-Unit in Kansas City, and another recent 1031 exchange where he acquired a 72-Unit during the Pandemic.

We cover a lot of ground in this episode, and I know you're going to benefit from the experiences Jonathan has had along the way. You can contact Jonathan on twitter: JB2Investments,

website: https://www.jb2investments.com

and ebook "The Tax Stack Strategy", which is available for free at https://www.jb2investments.com/lower

Today's episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area.

https://www.livegreenlocal.com

And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and medicare benefits.

https://www.rcbassociatesllc.com

Jaksot(589)

MREIC 2026 Speaker Spotlight: John Burley—Raise Capital for Your Next Deal Like a Pro

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Every real estate investor has at least one deal they would redo if given the chance. Some teach expensive lessons. Others leave scars. In this episode, Brian Hamrick shares a live panel recording fro...

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Rebuilding After Losing $50 Million: Rod Khleif on Mindset, Wealth, and the Future of Real Estate

Rebuilding After Losing $50 Million: Rod Khleif on Mindset, Wealth, and the Future of Real Estate

How do you come back after losing $50 million — and build it all back stronger? In this episode, Rod Khleif, multifamily investor, mentor to thousands, and host of one of the world's top real estate p...

23 Helmi 33min

The Hidden Financial Tool Every Real Estate Investor Should Know: Surety Bonds with Gary Eastman

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Most real estate investors have never heard of surety bonds, yet these little-known financial tools can determine whether a project finishes on time—or falls apart. In this episode, Brian Hamrick talk...

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Why Distressed Office and Retail Could Be the Smartest Real Estate Play of 2026, with Scott Sherman

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Billions of dollars in office and retail buildings are trading at deep discounts right now. While most investors see risk, Scott Sherman, Founder and Principal of Torose Equities, sees opportunity. Sc...

9 Helmi 27min

New 1031 Exchange & Bonus Depreciation Updates for 2026: Tax-Smart Real-Estate Strategies with Dave Foster

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It's tax season — and the rules have changed again. With new updates to the 1031 exchange and bonus depreciation, real-estate investors have more ways than ever to defer taxes and build wealth in 2025...

2 Helmi 40min

Building Affordable Homes in Hawaii's Lava Zones: Fuzzy Jardine on Respecting the Land and Creating Generational Wealth

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Kolaiah "Fuzzy" Jardine, co-founder of HUI Mastermind, joins Brian Hamrick to share how he overcame adversity and built a multimillion-dollar real estate portfolio across Hawaii—developing over 100 af...

26 Tammi 30min

Conference Announcement: Midwest Real Estate Investor Conference April 27–28, 2026

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The Midwest Real Estate Investor Conference (MREIC) is back April 27–28, 2026 at DeVos Place in Grand Rapids, Michigan, and this year's theme is Thrive. This quick special announcement features Erika ...

22 Tammi 9min

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