Jeremy Ostermiller on Entrepreneurship, Leadership & the Power of the Pivot

What does it take to keep building businesses for 20 years? For Jeremy Ostermiller, it comes down to finding work you love, hiring the right people, thinking bigger, and never being afraid to pivot.

In this episode of the Mile High Success Podcast, Nick Elder sits down with entrepreneur Jeremy Ostermiller to talk about the lessons he has learned over roughly 40,000 hours as an entrepreneur.

Jeremy started his first business at 15 and later built Altitude Digital from just $500 into a digital media company that generated more than $250 million in revenue before a successful merger. Today, he is chairman and co-founder of Edison Interactive and is building consumer brands including Death Before Decaf and Steel Town Garage.

Jeremy shares why entrepreneurs should stop waiting for the perfect idea and instead find an industry they truly care about. He explains why your first idea probably will not look anything like the business you have six or eight years later—and why that is a good thing.

Nick and Jeremy also dig into one of the hardest parts of growing a company: people. Jeremy shares what he looks for when hiring, why optimism matters to him, and how his leadership style has changed from micromanaging to managing, coaching, and ultimately leading.

They also discuss building businesses that can make money around the clock, finding mentors and strong peer groups, learning from travel, creating companies that can cross borders, and looking for opportunities with room for exponential growth.

One theme runs through Jeremy's entire story: keep moving. When you reach a dead end, find another way around.

Jeremy Ostermiller is an entrepreneur, investor, chairman and co-founder of Edison Interactive, and the entrepreneur behind Death Before Decaf and Steel Town Garage. He has been named Colorado Technology Association's Entrepreneur of the Year and recognized by the Denver Business Journal as a 40 Under 40 honoree.