140: High School Dropout to $500M in Companies with Brian Will // The Jack Bosch Show
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140: High School Dropout to $500M in Companies with Brian Will // The Jack Bosch Show
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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 problems into profit. They also get real about the multifamily reckoning and why now might be the time to buy.
Grab Brian's books at brianwillmedia.com and check out his new AI venture at livingforeverai.com.
Timestamps:
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00:00 — Meet Brian Will: Half a Billion Built, Everything Lost Once
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02:44 — The 80% Mistake & Lifestyle Creep
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07:26 — "Ambitiously Lazy" & Your Personal Filter
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25:47 — The Multifamily Reckoning
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38:39 — The 5 Keys to Success + Living Forever AI