The Jack Bosch Show

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141: The Multifamily Reset Nobody Saw Coming with Ken McElroy // The Jack Bosch Show

July 30, 2026

Show Notes: Ken McElroy is buying apartments at 50, 60, 70 cents on the dollar right now — and in some cases less. The multifamily legend and longtime Rich Dad advisor is back on the show, and he doesn't sugarcoat it. Ken breaks down exactly how the Fed repriced the entire market, why lenders and owners are both stuck in a standoff nobody's winning, and where we actually are in this cycle. He explains the supply cliff coming in 2027, why he expects massive rent growth in 2028–2029, and what A...

140: High School Dropout to $500M in Companies with Brian Will // The Jack Bosch Show

June 04, 2026

Brian Will was a high school dropout who went on to build companies worth half a billion dollars. He also lost everything once — and that failure taught him more than any of the wins ever did. In this episode, Jack sits down with the two-time Wall Street Journal bestselling author and serial entrepreneur to break down what actually makes a business survive: never letting one customer own you, keeping your ego in check, knowing your numbers cold, and being "ambitiously lazy" enough to turn pro...

139: Over The Counter Tax Sales // Buy Land With ZERO Competition // The Jack Bosch Show

May 21, 2026

Most investors have no clue this list even exists. When a tax-delinquent property fails to sell at the deed auction, the county doesn't toss it aside — it ends up on an "over-the-counter" or "struck-off" list, and you can scoop it up at the minimum bid with zero competition.   In this episode, Jack pulls back the curtain on the niche strategy he and Michelle stumbled onto 23 years ago, breaks down the difference between tax lien and tax deed states, and walks through how to spot the gems vs. ...