From Teenage Founder to Scaling a $250M Business: Dan Schiffman on Building, Exits, and Pivots

05/08/2025 43 min

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Episode Synopsis

Dan Schiffman founded his first tech startup at 15, almost 25 years ago. Since then, he has built a playbook that covers every stage of the founder journey: bootstrapping an e-commerce startup to a $1 million exit, co-founding a VC-backed trailblazer (TVision) that has raised close to $60 million, and leading the transformation of another business from $50 million to $250 million in just 18 months.In this episode, Dan breaks down the lessons from his unique career. He shares the strategic differences between bootstrapping and raising venture capital, his counter-intuitive rules for building a company that’s destined for a major exit, and his definition of the one word that matters most in entrepreneurship: "Hustle."Follow 23mile on LinkedIn or X and email us at [email protected]

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