Leonardo Rocco '99’s successes total millions of dollars in raised capital and investments, countless hours of agonizing brainstorming and a plethora of digital technologies and products that are coveted by the leaders of the technology industry. But it’s the early failure that hardened Rocco’s entrepreneurial spirit and developed his business philosophy. It was the failure that taught him most about the self-sacrifice necessary to succeed.

“I was on the verge of being evicted from my apartment,” Rocco said. “I used the money for rent to fund the company in 2009 and 2010. Those were very gloomy days.”

In 2008, Rocco left an executive position at IBM in San Francisco to start a company that focused on ordering drinks at a bar via text message. Ultimately, due to the technology and mindsets of the time, it didn’t work.

“It was my first true experience where I witnessed complete failure,” Rocco said. “It failed both in terms of the money that I personally invested in the company and in terms of collaborating with my team, I was unable to keep the group together and I left.”

Rocco describes a startup as a marriage between all associated team members and partners which makes it crucial for everyone to communicate, work together and see it through to the end, but in this case all the stakeholders were not willing to compromise and progress towards a unified goal. 

Leonardo Rocco '99

“Any time you see people starting companies, you need to respect the sacrifice they are making and the challenges they are facing; it’s tough,” Rocco said. “You have to be a tremendous leader – great at engineering, marketing, sales, accounting, etc. You need to be great at everything.”

Despite the struggle and hardship, this wasn’t Rocco’s last attempt at building the next great organization and his persistence would pay off in multiple ground breaking deals with Fortune 500 companies in the future.

Humble Beginnings

Rocco grew up in Buffalo, New York, a community facing similar post-industrial challenges as Flint, Michigan. His father was a self-employed tailor who owned a shop in Orchard Park, New York where, per chance, a Ford Motor Company executive brought in his suits and introduced the family to Kettering University. Inspired by the co-op and experiential learning model, Rocco’s older brother Mike (’95) first attended Kettering and Leo soon followed.

“My brother had such an amazing experience and my family was actively involved throughout his college career so I was sold on Kettering since my sophomore year of high school,” Rocco said. “I come from humble means. My father is a tailor. We didn’t really have a lot of disposable income. The co-op program made it a great option.”

Upon arriving at Kettering, Rocco felt at home with the city and campus as it closely resembled his upbringing in Buffalo while at the same time introducing him to outstanding students, faculty and peers that expanded his worldview.

“What you get at Kettering are individuals who are extremely hungry to advance in life and make a change in the world and those are the individuals that seek out what Kettering can offer,” Rocco said. “It’s the highly motivated people who want to constantly get better and advance themselves out of their existing social class.”

Kettering to Entrepreneurship

There’s a moment during Rocco’s academic career at Kettering that still stands out to him to this day. In 1997, before computer technology was prevalent in the classroom, Rocco sat in Professor Jeff Hargrove’s class attempting to learn how to use CAD. The problem: the class was learning how to use a digital design program on an overhead projector and chalkboard.

“That was ridiculous to me,” Rocco said. “I set out tirelessly to put my professor’s lesson plans on the computer. I proved the theory that online tutorials or online applications can help students learn how to use software more efficiently and I specifically focused on CAD and Pro-Engineer.”

Pro-Professor was an online learning system for Pro-Engineer that Rocco was developing for his senior thesis project. The idea was to transfer learning online similar to modern systems like Blackboard and D2L on college campuses today. But this was one of the first of its kind. When he presented his thesis to his co-op employer, Parametric Technologies, Rocco’s entrepreneurial career officially began.

“Paul Cloutier (’92) ‘brokered the deal’ and convinced PTC to hire me and they subsequently acquired the IP of Pro-Professor,” Rocco said.

Rocco moved to Boston to work for Parametric Technologies after graduating from Kettering in 1999 with a degree in mechanical engineering with a minor in information systems. In addition to Pro-Engineer, Rocco began working on an automated project management software for companies like Ford, Ferrari, Intel and NASA. The aim of the software was to increase efficiency of large projects by automatically updating progress and assigning upcoming tasks to the team.

Looking for a new challenge, in 2002, he moved to Chicago to explore an MBA at the University of Chicago, however, his software development roots had him reconsider an MBA for lead a position at a new start up in San Francisco that was acquired by IBM. Rocco quickly elevated himself to the global executive for IBM’s software development relationships with HP, Cisco and Intel and by doing so, experienced his first foray into sales which further developed his entrepreneurial mindset. 

“My job was to lead a global team and help these companies standardize their software development process on IBM technology,” Rocco said. “I traveled the world more than five times – Tel Aviv, Tokyo, Moscow, Shanghai, Bombay – met with all of the different offices of Cisco, Intel and HP and helped centralize the purchasing of software from each of their Silicon Valley headquarters.”

Rocco helped broker a landmark software purchasing deal worth over $100 million which also provided unprecedented savings for the global operations of all three companies.

After experiencing extraordinary success to this point in his career, unfortunately or fortunately depending on how it’s viewed, Rocco’s creativity pushed him away from IBM and towards his first entrepreneurial failure.

Breaking the Glass Ceiling

“When you’re an entrepreneur, you have to go in 100 percent,” Rocco said. “This whole moonlighting thing might work, but you have to cut the cord at some point, you have to go all in or your opportunity of failure is higher.”

Rocco went in 100 percent in 2008 when he left IBM to start a company focused on developing a texting software to order drinks at a bar. Unfortunately, the company failed but that didn’t alter his pursuit of innovation.

“I’m a scrappy entrepreneur who takes attitude and concepts and eventually builds a company from it,” Rocco said. “I’m not a guy that needs a big company support structure. I’m molded to be a disruptor.”

In August 2009, Rocco launched GoPago – an attempt at standardizing cloud-based online commerce for small and large businesses. For example, the premise was that a consumer can order a coffee from a coffee shop before arriving and only be present to pick it up and therefore avoid or skip the line.

“The whole idea of having the phone just replace the plastic credit card – it’s just not enough,” Rocco said. “It’s about changing and improving the buying experience for the consumer and the merchant.”

The premise and execution was solid but the product was difficult to sell to both merchants and consumers at the same time. Rocco and his development team felt that they had to choose either one market or the other. After running out of money five times and on the verge of shutting down the company, they got their big break, a chance occurrence that would be ridiculed if it was written as fiction and is only believable because it actually occurred.

“In late 2010, we got an email from a JP Morgan executive saying, ‘I just used your technology at a coffee shop in Mountain View, California. I had the most awesome experience. Please call us if you’re interested in being more strategic and work with us,’ Rocco said. “We had three people in the company at the time. We had minimal money. We were operating on fumes. I was thinking: here’s an opportunity of a lifetime, if this guy only knew I had no money to make rent and the business was on the verge of failure. You have to have a steel stomach.”

While negotiating with JP Morgan, Rocco flew around the country and raised another $1 million in funds to hold the company over during the process. Finally, in October 2011, Rocco presented GoPago to Jamie Dimon’s (Chairman, President and Chief Executive Officer of JP Morgan) executive staff to sell them on the company The result: a $13.5 million Series A investment - one of the largest Series A rounds in Silicon Valley. 

“We went out and had a party,” Rocco said. “We ramped up the company from seven people to 30 employees. We’re hiring tons of engineers. We go from 30 engineers to 60 people. CNN, MSNBC, FoxNews, Wall Street Journal, Tech Crunch; every body was interested in what we were up to. We were listening to the market. We were adjusting to the product. We had to continue to pivot. We grew to a 90 person company.”

With growth came notoriety and attention and in Silicon Valley, that means prospective investors and acquirers. In GoPago’s case, that meant Google and Amazon.

“When Google comes to you and says that you’ve built the most innovative android-based commerce platform they’ve seen then we’re onto something,” Rocco said.

After six months of negotiations with both Google and Amazon, ultimately, Amazon agreed to purchase GoPago in December 2013. However, two days before the agreement was finalized, Rocco threw a caveat in the deal – he wouldn’t be a part of it.

“I told them that I wasn’t going to work for Amazon. That kind of bugged them a bit,” Rocco said. “I decided to travel with my wife instead. I got married in August 2013 and we didn’t take a honeymoon because there was so much going on at that time.”

Looking to the Future

Rocco has since returned from his travels and on Oct. t, he, along with six of his fellow Kettering University graduates, will be honored at an Alumni Dinner and Ceremony. Rocco will receive the 2014 Entrepreneurial Achievement Award.

Since selling GoPago, Rocco has become an investor in multiple companies and has joined CIELO US as their chief product officer to oversee all of their product and engineering development. He works out of their Silicon Valley office in Redwood City. After the highs and lows of founding, building and selling a company, Rocco is one again falling back on his engineering roots as he continues to map out the next portion of his professional career and entrepreneurial pursuits.

“In industries that are new and unfamiliar to me, I am able to leverage my engineering background, to learn them fast, take a fresh look, and obsessively look to disrupt and build a better mouse trap,” Rocco said. “As an engineer, you can learn anything. People aren’t born experts. People are born with the raw skills to learn and in some cases with the ability to lead. I look at every day as an opportunity to make history and an impact on the world. Imagine if everyone felt that way; where would we be today?”