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20 Companies and Over 1 Billion Dollars Later

Brent Freeman was 23, fresh out of USC and carrying a quarter million dollars in student debt, when he closed a $10 million deal in Dubai. He celebrated that night and the next morning he woke up expecting to feel fulfilled. Instead, he felt empty. “Full stop. Money does not make you happier,” he told me on Founder’s Story. Going From $1 Billion in Deals to Total Burnout Freeman went on to co-found 20 companies that generated over $1 billion in revenue. Italy’s former royal family knighted him, and he founded the world’s number-one Airbnb experience. But he is…

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