My Story – Jeremy Ostermiller

This is My story

Entrepreneurship has always been part of who I am. At 14, I started my first clothing business, designing and selling t-shirts to friends and family. At 15, I launched a mail-order rollerblade and accessory business, Rocky Mountain Deals on Wheels, with my parents, Marvin and Debbie. As an avid hockey player, I noticed rollerblade wheels were expensive, so I found a way to source blemished wheels and sell them at a big discount, making the gear more affordable and accessible. These early ventures taught me how to start a business, find product-market fit, and develop skills in sales and marketing—lessons that sparked a drive and mindset I carry with me to this day.

After high school, I brought that entrepreneurial spirit to the football field, playing varsity at the University of Northern Colorado before transferring to Colorado State University, where I earned a degree in Technical Journalism. Those years reinforced the importance of teamwork, resilience, and communication, all of which became foundational to my journey as an entrepreneur.

In 2002, I co-founded JFLY Presents, producing over 400 live events and working with artists like Snoop Dogg, LL Cool J, Bone Thugs-N-Harmony, CeeLo Green, and the Wu-Tang Clan. These experiences taught me more than just how to organize events—they helped me connect with people from all walks of life. Whether it was collaborating with artists, negotiating with venue operators, promoting events, or selling tickets, I developed a knack for building genuine relationships by meeting people where they are. Being able to adapt and understand different perspectives has always been one of my greatest strengths. It’s about finding common ground, appreciating where others are coming from, and creating an environment where everyone feels valued. This ability to connect has been key to bringing people together and making ideas come to life.

In 2009, I founded Altitude Digital with $500 and a vision, scaling it to $250M+ revenue, raising $30M, and earning 9X Inc. 5000 and 2X Deloitte Fast 500 awards. Beyond these milestones, I valued creating opportunities for people to grow and succeed.

Not one to stop building, I co-founded Edison Interactive in 2016. Partnering with companies like Verizon, Avis, and Caesars Entertainment, Edison grew into a leader in managing over 100,000 connected screens across North America. The work was exciting, but the most fulfilling part was helping others innovate, recognize opportunities, and discover their potential.

This passion for helping others led me to invest deeply in mentoring. Through the Blackstone Entrepreneurs Network, my role on the Colorado State University College of Business Board of Advisors, and programs like Youth on Record, I’ve worked with countless individuals to unlock their potential. For me, mentoring isn’t just about sharing knowledge; it’s about seeing others succeed, showing them what’s possible, and helping them break ceilings they never thought they could surpass. It’s about being a connector, someone who helps people see opportunities, grow into their best selves, and thrive in ways that ripple outward.

Now, I channel all of this into my consulting company, Rocketfuel, where I help leaders and entrepreneurs uncover opportunities, drive growth, and ignite innovation. Rocketfuel isn’t just about solving problems; it’s about empowering others to achieve what they didn’t think was possible. What excites me most is watching others grow, seeing the breakthroughs, the moments when everything clicks, and the impact they go on to create.

For me, success is about more than the businesses I’ve built or the milestones I’ve achieved. It’s about the connections I’ve made, the people I’ve inspired, and the opportunities I’ve helped others discover. Being a connector is what drives me, bringing people, ideas, and possibilities together to create something extraordinary. That’s what makes it all matter and keeps me energized to keep building, inspiring, and making a difference every single day.