Scrappiness and learning by doing: How to start a company without dropping out of school

Carson Hunt and Jorge Obeso discuss their journey founding Upparel — an end-to-end custom merchandising solution

Upparel connects suppliers and business buyers of custom merchandise. After years of experiencing the pain points of both sides of the market, Carson and Jorge set out to develop and distribute technology that would change the way the promotional product industry operates. 

Jorge Obeso spotted a problem during his sophomore year of college, when he was the apparel chair for his fraternity and realized that students were overpaying for t-shirts. He had previous graphic design experience and decided to make custom apparel for his fraternity — which quickly spread to other houses across campus and to different universities.

He co-founded Upparel with Carson Hunt, who he knew from high school, after they worked together for months selling apparel as a side hustle. 

As the intermediary between suppliers and buyers, they began to notice a larger issue — the order process was overtly inefficient: they spent days going back and forth via email and phone calls to place orders for clients —  and it was clear that the industry had little to no technological adoption.

“We were selling t-shirts to Greek houses, and then eventually to businesses and large enterprises. Throughout this process, we wanted to do everything we could to streamline our internal operations and provide a better customer experience through e-commerce and different design tools,” Carson explained. “After doing that for a couple of years, we realized the technology we were using for ourselves could work for the other 40,000 suppliers in the U.S., too — so we began to focus on the tech.” 

Upparel started as a side project in late 2017, was incorporated in 2018 and eventually pivoted to focus on technology in 2019. Now, it’s providing promotional product suppliers with the necessary technology to modernize their business alongside a rapidly changing environment. They’re helping other suppliers achieve Upparel’s original goals of streamlining operational capabilities, expanding production, and providing a frictionless customer experience. 

Focus on gaining real-world experiences

Jorge’s entrepreneurial journey began years before university and Upparel: he was selling plush toys at 8 years old, sneakers throughout middle school, and had founded his first company — a full-suite digital marketing agency — at 13.

“School came easy, but I was always more passionate about solving complex problems with different business ideas I’d come up with,” he said. “It wasn’t till the year before college that I came across the word ‘entrepreneurship,’ and realized there was a world for this.”

He was on a full scholarship at Indiana University and balanced keeping his grades up with gaining tons practical experience. He worked on Startup IU, a community of close to 2000 people across campuses and different startups, and dove into understanding the fundamentals of entrepreneurship. By his junior year, he had interned at, a VC firm, where he worked with the CEO of a portfolio company to raise their Series A and architect an 18-month strategic growth plan.

While Jorge balanced school and work, Carson, who was previously on the Dean’s list at the University of Central Florida, took a more extreme approach and put startups before schoolwork.

“I thought I couldn’t do well at both, and ended up prioritizing the business,” he explained. “I’m super passionate about this, and in my experience, the lessons I was learning in academics were too one-dimensional and structured.” 

Carson, who previously interned with Lockheed Martin and Tesla, advocates for university students to place more emphasis on real-world experiences. 

He practices what he preaches, and puts Upparel and work experience first. In fact, once his grades began to fall, he received a letter from the company explaining that his GPA had fallen below the threshold required to continue working at Lockheed Martin. He was no longer eligible to work there — but this only encouraged him further, he explained as he gestured to the framed letter on his wall. 

“I’m super stubborn and took that and rode with it,” he said. “But it’s certainly something that came with the decision I made.” 

But with a high GPA or not, juggling school, a company and other real-world responsibilities can feel like an impossible feat. Carson and Jorge explain how it requires lots of hard work, taking initiative on things early on, and often sacrificing sleep. 

“It’s definitely a commitment. Being close with your professors and trying to immerse yourself in the community of your school helps with leniency, but ultimately you have to be willing to sacrifice certain things” Jorge said. “Realistically, it’s a lot of late nights, grit, and discipline and not a lot of partying.” 

Learn what you need to learn 

As founders who need to form and hone business and technical skills, school is a great place to learn — but not every lesson applies. 

 “I choose what I want to learn within the business school. If it’s just theoretical concepts and superfluous business terminology, I wouldn’t pay attention,” said Jorge. A lot of it was YouTubing and teaching ourselves things as we went, but I try to take any sort of class that can grant practical value in building a business — even if it is outside my degree track.”

Upparel pushed them out of their comfort zones and forced quick learning — they had to be scrappy and resourceful to get things done. 

Neither Carson nor Jorge are developers, but they bootstrapped $300k in traditional promotional item sales to reinvest in an offshore development team. They flew to Mexico over 5 times during the school year to meet suppliers and had to teach themselves the necessary skills to manage an offshore team and develop Upparel’s technology. 

“Part of it was understanding that there are more qualified people than me in just about every vertical, and seeking out their guidance,” said Carson. “There’s some things you can learn at school, and others you can’t. Read books and watch videos on past CEOs and founders. If you can’t talk to them, you can learn how they think and view the world. 

Leverage existing connections and expand your network

Both co-founders couldn’t emphasize the need to network enough — and they even leveraged their internships and connections to forgo traditional sales channels and get their first clients. 

“I swear up and down by LinkedIn,” said Carson, who has over 3500 followers on the platform. “It’s such an important tool for people who don’t have a network to form a network. It isn’t about finding internships, it’s much, much more than that.”

When building a technology company, a basic development understanding can only get you so far — so they leveraged their connections from previous internships to help vet talent, launch Upparel’s MVP, and strategize their best path forward. 

Jorge found success with two things: reaching out to people through cold email and finding a way to provide value first. As an intern at, he made a conscious effort to meet every CEO, and talk to just about everyone he could to seek out mentorship and learn from as many people as possible.

“Coming from an immigrant family with no background in business, I didn’t have a preexisting network so I had to find a way to make one. The key is to surround yourself with people you can learn from, provide them value, and work harder than everyone around you. Most people don’t really extend out, so it’s important to make yourself known and to not be afraid to ask for guidance,” he explained.

Both recognized that reaching out can be easier said than done — and that people are often scared of taking the first step. But as a college student, a strong network can be the biggest asset for a first-time founder, and it’s important to change the mindset that it’s rude to send an email to someone “high up” asking for guidance. 

“Don’t be afraid to reach out for advice, whether it’s your Dean or a CEO, you’re never in too low a position to reach out for help,” Carson said. “If I were in their position, I’d be impressed by the courage it takes to send that first email.” 

Written by Mahira Dayal, Head of Content at Dorm Room Fund. Follow her on Twitter.

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