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The Real Estate Tax Loophole That Saved Me $1,000,000 (And Built a $100M Empire) Elliott Caldwell
Elliott Caldwell made $3.5 million in 2025. Without the strategy in this episode, he would have paid over $1 million in taxes. Instead, his bill was $160,000. Elliott is the CEO and co-founder of The Rise Collective, 13 businesses built starting from a single Airbnb tax loophole he found on YouTube in 2019. From BNB Turnkey (a done-for-you Airbnb investment service with a negat...

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How a High School Dropout Built a $2M Business (No Degree Needed)
Daniel Lackey dropped out of high school, worked the oil fields in North Dakota, and was homeless at 18. Today he owns CMD Claim Consultants, a public adjusting firm he scaled to almost 2 million dollars, and he just launched a general contracting company, RCF and Associates, with his father-in-law. In this episode we get into how he built his own firm in six months by giving a...

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Stop Glorifying Hustle Culture Sofia Kasuli on Building a Business Without Burning Out
Sofia Kasuli spent ten years building sales teams before she ever started her own company, and less than a year into running SoFluential Society, she is already helping women build sales skills, travel the world, and get out of their own way on camera. We get into what actually surprised her about the cost of starting a business, why she believes busyness itself is the thing bu...

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Spend Money As An Insurance Policy Kevin Sullivan on Building a Law Firm the Right Way
Kevin Sullivan has represented close to 1,500 accident victims and recovered more than $40 million as a personal injury attorney and shareholder at LeavenLaw in Tampa Bay, and he built most of it through social media and word of mouth rather than the billboard ads everyone else runs. We get into why he looks at running a business the same way I do, build the value first, put in...

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The Sport That Saves Lives: How Micha Seal Built a 5-Location Empire
Micha Seal's mother started teaching swim lessons out of a backyard pool in Tampa in 1979. Today Micha runs Watermelon Swim, a five location swim school teaching around 7,000 kids a week, and her mission is building a community of safer swimmers. We get into what happened when 40 percent enrollment growth almost broke her business, why her rule is if it isn't written down it do...

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