Connor Santana: From Military Logistics to Market Innovation 

Connor Santana's entrepreneurial journey began not in a garage or college dorm, but in the disciplined halls of West Point. Graduating in 2015, he embarked on a five-year career as a logistics officer in the U.S. Army, unknowingly laying the foundation for his future business ventures.

"During my career, I was largely in charge of moving military equipment, in shipping containers, ammunition, all of the above, across international borders," Connor explains. This expertise in logistics would later prove invaluable, though not in ways he initially expected.

The First Steps:

In 2018, while still serving in the military, Connor and his future wife began flipping houses together. "We would tear out carpet together, tear up cabinets together," he recalls. "Then after that, I would go to the field for two months, I'd come back, and she had torn out some more stuff, gutted more parts of the house."

This experience not only taught them about business but strengthened their relationship through shared entrepreneurial spirit. After leaving the military in 2020, Connor transitioned to Lockheed Martin Space, working with satellites for about a year and a half. However, the entrepreneurial bug had already bitten. In 2021, influenced by his wife's encouragement, he launched his first company selling compostable restaurant disposables.

The Humbling Journey:

The early days of the disposables business tested Connor's resolve. "I would go door to door in downtown Colorado Springs, door knocking on different restaurants with a box of 50 straws," he shares. "And it wasn't even just restaurants. I would knock on Colorado antique stores, coffee shops, even gift shops, ice cream stores, everything." The rejection was constant and crushing. One rainy day stands out in his memory: "I distinctly remember it because I was walking with my box of 50 straws. The box was getting wet. I was told 'no,' I didn't even get one 'yes' that day. And I got back to my car, and I had a mental breakdown." What kept him going? Two things: his wife's unwavering support and a crucial strategy shift. "My wife has started startups since she was 13 years old," Connor explains. "She has gone through many more rejections than I have." Her experience and perspective helped him weather the storms of entrepreneurship.

The Breakthrough Moment:

The turning point came when they changed their approach, targeting larger distributors instead of individual shops. This led to their first major success: a restaurant that ordered multiple cases - about 25,000 straws, representing half their inventory at the time. "It was that win that motivated me and drove me to realize, look, I just need to find the right people, I need to find the right exposure," Connor reflects. This success taught him valuable lessons about market strategy and perseverance.

Birth of RollUp

In 2022, while still running the straw business, Connor began developing RollUp, a revolutionary approach to junk removal services. The initial inspiration came from his time flipping houses with his wife. After a demo, they had piles of junk and had no way to transport it to the dump themselves, for they both owned sedans. They could not afford traditional junk removal services, and instead elected to cut up the junk to dispose in their trashcan over 4 or 5 weeks. They wondered why there was not an app to connect them with “a guy with a truck”, but on their terms. hisAnother motivation was Connor’s own military transition experience and observing others struggling to find consistent income opportunities. "One of my focuses is providing more job opportunities and ways for people to make money in this economy," Connor explains. "When I was transitioning out of the military, one thing that really struck me was the scramble to find a job, the scramble to find some sort of consistent income, some place to fit in." RollUp's innovative approach allows customers to name their price for junk removal services while providing flexible earning opportunities for haulers. The platform has now expanded to 14 states, with haulers able to turn on the app, make a few hundred dollars, and maintain independence in their work schedule.

The Evolution of Success:

Connor's definition of success has evolved significantly throughout his entrepreneurial journey. "My vision for success was ensuring that RollUp became the DoorDash of junk removal," he notes. "The more I get into my journey, I'm finding that success is just making it to the next step, making it to the next meeting with an investor, making it to the next state that our app is operating out of." This perspective shift came with valuable mentorship. "Recently I was talking to my mentor, who has been very critical to the success of our company RollUp. And something he made sure I understood was that you can have lofty goals, lofty visions for where you want your company ultimately going, but you can't forget to celebrate the many mini successes along the way."

Lessons Learned:

The most crucial lesson Connor wishes he'd learned earlier? "You can't really care what other people think about your journey, your career journey," he reflects. "It wasn't until I started with straws, but even probably more so with RollUp, that I recognized that it's still important to listen to family, to at least hear them out, not even just family, but friends too, but ultimately you have to keep that vision in mind and be very self-driven." This lesson proved particularly valuable as he transitioned from being known as the "Straw Man" to leading a tech-enabled services platform. The journey taught him to wear his entrepreneurial choices with pride, regardless of how others might perceive them.

Future Vision:

Connor's ambitions for RollUp extend far beyond junk removal. "Our vision for RollUp is much more than just junk removal. It's this whole concept, the technology, the infrastructure behind our app, that has many other applications outside of just junk removal," he explains. The platform's ability to create real-time market dynamics by allowing customers to set prices could potentially revolutionize various service industries. "It's this flipping of the supply and demand, today’s standard quotation and negotiation process, on its head," Connor notes.

Advice for Aspiring Entrepreneurs

For those starting their entrepreneurial journey, Connor emphasizes the importance of mentorship and community. "Find a good mentor. That would be my biggest advice," he states. "With RollUp, we've been very fortunate to have met with several mentors, and I largely owe this to Exponential Impact. It introduced me into a whole other world that I had never known."

He also stresses the importance of remembering your initial motivation during tough times. "My favorite advice is when the times get tough, because times will get tough, is to look back at what your initial motivation was for starting that company. If you know what your rock is, then it's going to make those tough days, those tough nights, a little bit easier."