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Welcome to The Elliott Caldwell Podcast on Successful DNA — the show where driven individuals break down the habits, experiences, and mindset behind building something real. Whether you’re an entrepreneur, investor, or someone chasing your next level, this podcast uncovers what it actually takes to turn momentum into long-term success.

Jake Schmidt is the co-founder of Capstar Real Estate, a hybrid brokerage and investment firm built on creative finance, digital lead generation, and lean execution. In this episode, Jake walks through his unconventional path — from college lacrosse player and poker grinder to medical device sales rep, full-time real estate investor, and founder of a fast-growing brokerage.

Jake breaks down how he sold his first deals with no experience, why betting on himself in 2021 changed everything, and how Capstar was built differently from traditional brokerages. He explains creative finance strategies like seller financing, wholesaling, private capital, and flipping — including a hoarder house flip that reshaped how he approaches projects.

Beyond real estate, Jake shares the story behind launching Cousin Vinny’s, a Michelin-recognized Italian sandwich concept that exploded from a ghost kitchen into a brick-and-mortar success — and why brand, marketing, and operational discipline mattered more than hype. He also dives into bitcoin mining, passive investing, and how he allocates time across multiple ventures.

At the core of Jake’s philosophy is a simple truth: you can’t lose if you don’t quit. From raising private capital without his own money to building loyal teams and solving deals like puzzles, this episode is a masterclass on competitiveness, resilience, and long-term thinking.

This is a raw, wide-ranging conversation on entrepreneurship, real estate, creative finance, and the DNA required to win — even when the market gets hard.

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