Ilya Braude approached his first startup with caution.
It was 2006 and he was fresh out of Drexel, working at a more traditional tech company, where he built software for network management systems. A Drexel professor, whom he initially met through the Drexel Karate Club, had asked him to join his startup — a law enforcement software company called Drakontas.
Braude hesitated. It seemed risky. Would he have to worry about getting a paycheck every month? Would people tell him to “get a real job”?
In the end, his friend and fellow Drexel grad Chris Cera convinced him to do it. Cera himself had recently joined Drakontas. That was the beginning. Today, Braude, 32, has spent nearly a decade working at Philly startups, including his own: CloudMine.
But that has changed in recent months.
He left CloudMine to run a consulting business for startups and companies looking to build tech products. He’s also leaving Philly for Baltimore because his fiancee is due to start her medical school residency at Johns Hopkins, though he plans to be back and forth frequently because many of his clients are Philly-based.
Braude said he is still “heavily invested” in CloudMine, which recently raised a $5 million Series A and moved into a new Center City office, and still has equity in it. He felt like it was time to try something new, plus he knew he was going to leave Philly because of his fiancee’s residency.
When reached for comment, CloudMine CEO Brendan McCorkle wrote: “We appreciate his efforts and technical abilities, and all he has done for the company, and thank him for his contributions and value added over the last 4 years to help get the company to where it is today. We wish him the very best going forward.”
When he met McCorkle in 2011, Braude was on the hunt for a startup. He had spent three years at Drakontas and now he was ready to run his own. (Braude was also inspired by Cera, the friend who convinced him to join Drakontas, who had started his own startup, Arcweb.) By then, Braude was all in.
“I was sold, hook, line, and sinker into the whole startup thing,” he said.
He met McCorkle at a Philly Startup Leaders happy hour. McCorkle, he remembered, was very tall. (He still is.)
“I turned around and I was staring at this guy’s belly button,” Braude said. “I was like, ‘Hello there.'”
McCorkle had this idea for a startup that acted as a mobile backup for Apple and Google (this was before Apple had their own mobile backup — CloudMine later pivoted) and though Braude had heard pitches from other entrepreneurs, something with McCorkle just clicked.
“You know,” Braude said, “he’s a smooth talker.”
Soon after, they got accepted into startup accelerator DreamIt Ventures and Braude quit his job at Drakontas.
Braude later took on the role of VP of Engineering and COO, where he learned that running a startup isn’t only about technology. It’s about payroll, taxes, insurance, invoicing. Someone’s gotta do it.
He also oversaw customer support and DevOps, which meant he was constantly “on call,” the first responder if there were any server problems. He always had to carry a laptop around, just in case. That’s something he won’t miss, he said. He still has PTSD whenever he hears the ringtone he had set up for those alerts.
So what’s it like leaving a startup that you committed the last four years of your life to?
“I think about it a lot,” Braude said.
He struggled to find the words to explain how he felt, but what he did say was this: It wasn’t an easy decision to leave, even if it might have seemed like it.
“People see me as this stoic character, like ‘Execute or get the fuck out,'” Braude said. But, “I have emotions. I’m not a rock.” It was the right move for him, he said.