Today's episode features a special guest, Jeff Bragg, founder of Bragg About This Dump. Jeff and Josh go way back, and in this episode, they are literally talking trash! Jeff shares his incredible entrepreneurial journey, starting as a high school dropout who sold candy to buy a baseball bat, to working at a warehouse, owning a pizza franchise, and even running a recreational weed farm in Oregon.

After returning home and getting into real estate, Jeff experienced a massive headache: he couldn't get a dumpster delivered to his rehab site. Out of pure frustration, he bought his own truck and trailer. He then applied the private lending and Other People's Money (OPM) strategies he learned from Josh and Tiffany to rapidly scale his new venture. Jeff explains how he grew from 10 to over 100 dumpsters using $1 million of private capital, the red flags to watch out for when renting a dumpster for your projects, and why hiring a mentor can save you a decade of trial and error.

Listen and enjoy the show!

You’ll Learn How To:

Overcome early failures and bet on yourself as an entrepreneur
Use Other People's Money (OPM) to quickly scale an equipment-based business
Structure private lending notes to manage cash flow during seasonal slowdowns
Avoid hidden fees and variable pricing traps when ordering dumpsters for your rehabs
Fast-track your success by modeling a mentor's proven framework

What You’ll Learn in This Episode:

(00:00) The value of finding a mentor to skip ten years of trial and error
(01:48) Jeff’s journey from dropping out of high school to finding his entrepreneurial spirit
(03:03) Why flipping houses with family made Jeff realize the importance of systems
(04:32) The major contractor headache that pushed Jeff to start a dumpster business out of spite
(05:44) Lessons learned from warehouse work, a 50/50 pizza franchise, and an Oregon weed farm
(09:04) Structuring 3-year private lending terms to survive slow winter months
(10:10) Josh breaks down how private lending and Other People's Money (OPM) actually work
(12:22) How Jeff used $1M in private capital to scale from 10 to 100 dumpsters
(15:27) How delayed dumpsters directly kill your rehab timelines and holding costs
(17:12) The importance of preemptive dumpster swaps for clean listing photos
(19:30) Major red flags in dumpster pricing and why to avoid "price per pound" models
(21:39) Why achievement is a science and how to "Steal Like an Artist"
(24:42) Jeff's future plans to scale to 250 dumpsters and expand to new cities

Who This Episode is For:

Real estate investors who want to better understand rehab logistics and holding costs
Entrepreneurs looking to scale an equipment or service-based business using private money
Anyone looking for inspiration on how to pivot from frustration into a highly profitable business opportunity

Why You Should Listen:

Jeff’s story is a masterclass in betting on yourself and finding the silver lining in everyday frustrations. If you've ever dealt with contractor delays that cost you money, you'll love hearing how Jeff turned that exact problem into a massive business. Plus, his breakdown of how he adapted real estate private lending models to buy heavy machinery is a brilliant lesson in creative financing that you can apply to almost any industry.

Connect with Jeff Bragg:

Jeff Bragg LinkedIn: Jeff Bragg II
Bragg About This Dump Instagram: