Bob Stasio

Never Stop Learning

Bob Stasio didn’t come from a military background, but as he was finishing high school and looking toward college, something about military service appealed to him. “I didn’t know what life in the military would be like,” he stresses, “but I found it interesting. Plus, I could go to school and study whatever appealed to me. I thought that was a pretty good deal to get my education paid for in return for military service.” In August of 2001, Bob signed his ROTC scholarship. A month later, the events of September 11, 2001 drastically changed the course of his future.

I took a calculated risk partly because I like to zig when other people zag. Without knowing anything about it, I picked the field of intelligence.

“I originally thought I would go in and do some desk duty somewhere,” Bob remembers, “but 9/11 changed everything.” Although Bob considered enlisting immediately, his instructors encouraged him to stay in ROTC and complete his training before heading overseas. “Before 9/11, much of the ROTC training involved infantry training and a lot of individuals continued down that path after graduation. I took a calculated risk partly because I like to zig when other people zag. Without knowing anything about it, I picked the field of intelligence.

From there, Bob’s career in intelligence flourished, but it was consistently an uphill battle. After training, he was deployed to Iraq during the Surge in April 2007. “I remember hitting the ground on day one and having absolutely nothing, no resources,” Bob recalls. “It was the most dire situations I’ve ever faced in my life. With over 150 attacks coming in everyday, It felt like an impossible, unwinnable situation. We had no equipment, literally nothing, nowhere to start.” Unlike most units, Bob’s Signals Intelligence Platoon was not relieving an existing unit, and thus, they had no one to show them the ropes. Their workspace was an empty room that was devoid of the tools Bob knew they’d need to conduct intelligence operations.

But during the course of his 15-month deployment, Bob and his team managed to completely turn the situation around. By the time his unit left Iraq, attacks in the area had been reduced drastically thanks to targeted raids informed by high-level intelligence collection. “We built everything from the ground up,” Bob says. “Seeing us become successful was a defining moment for me. My team and I picked ourselves up by our bootstraps and embraced the team concept. Because of our efforts we ended up winning an award for best Signal Intelligence unit in the Army that year, the NSA Director’s Trophy Award. We were the lowest level unit to ever win it.”

Today, Bob is the Managing Director of Dreamit Ventures, and the Founder and Managing Director of Secure Tech, a vertical within Dreamit. Although he’s worn many hats since college and developed a broad range of professional skills, one thing has remained consistent: his dedication to challenging himself and adopting an attitude of continuous learning. As Managing Director of Dreamit, Bob has brought many of the skills he acquired in the military, at NSA, Bloomberg, IBM, and as a small business owner to bear. He’s also acquired new skills as he’s learned the ins and outs of the finance world.

Dreamit Ventures is a venture capital fund with a tiered accelerator program dedicated to developing and investing in promising small businesses. During the course of a 14-week period, select businesses are put through a rigorous bootcamp with two major areas of focus—customer immersions and the investor roadshow. First, Dreamit makes connections between the small businesses and potential customers over the course of two weeks. “We hit Tampa, Philly, Boston, and New York,” says Bob, “and we’re going to get about two meetings a day with different customers that want to see start-ups. It’s a very intense two weeks.”

Next, Dreamit pairs the companies with a network of over 2000 investors and sets up one-on-one meetings. “Mostly, we’re looking at pre-series A companies that have a little bit of traction,” explains Bob, “we do a bicoastal tour, from New York and DC to San Francisco. We handle all the logistics and set the meetings. The average start-up has nineteen different meetings across two weeks and about 50% of our start-ups raise money. If they do raise money, Dreamit has the option to put $500,000 into the company as another investor.”

With this model, Dreamit has invested in over 300 companies over the past ten years, with about 140 still in its portfolio at a $2 billion total valuation. Their success as an accelerator has afforded them a global reputation; and global is the scope of the search as new companies are considered for the next 14-week program. “We canvass the world to find companies,” affirms Bob, “and we usually screen about 300 to find five to ten companies. It’s quite competitive with only a three percent acceptance rate.”

Dreamit invests in three major sectors—HealthTech, which encompasses medical devices and software; UrbanTech, which is dedicated to the design of smarter cities and smarter construction; and finally, the newest vertical, SecureTech. Bob was brought on to manage SecureTech because his extensive background in intelligence, cyber security, product management, and small business management made him the perfect candidate to identify and mentor promising security start-ups. “I’m giving them advice every day,” says Bob of his role. “I’m making connections for them with people, setting meetings with potential customers; it’s really the whole process from cradle to grave, from recruiting the companies and bringing them in, to guiding them through the process and working with them along the way. I have seven right now that are going through the process. Ideally, we’d like to invest in all of them, but only about 50% of the companies end up raising money.”

SecureTech allows Bob to make use of many of the professional skills he’s learned across a long and impressive career in intelligence, but he also gives particular credit to a less obvious source—working at his family’s jewelry store growing up.

As a kid growing up in the working class in the suburbs of Long Island, Bob, his younger sister, and younger brother spent most of their free time cleaning out the storage room, arranging displays of necklaces and earrings, and speaking with customers at the family jewelry store. Bob’s mother’s family owned two stores—one in New York City and one in Long Island—and for generations everyone in the family contributed to the success of the family business. “In the 1930s when my family came to the U.S. from Italy, they started jewelry stores,” explains Bob. “My mother worked there quite a bit, all of my aunts worked there, and my uncles were running it. From pretty much the time I was 11 or 12, I would sweep the floors, I would get them lunch and, I learned how to interact with the customers. It was actually a very formative background for entrepreneurship.”

Remaining calm under pressure, never saying ‘no, we can’t do that,’ and figuring out how to solve the situation, were skills that helped me in Iraq and to this day”

At the jewelry shop, Bob learned the importance of customer service. He learned how to accommodate seemingly impossible requests, how to deal with problems and bizarre situations, and most importantly, how to get a point across respectfully but firmly. “I also learned persistence,” Bob says, “and the value of a strong work ethic. It also helped to be creative when a customer came to you with a seemingly unsolvable program. Let’s say a customer comes in on February 13th and asks for a custom job for Valentines Day. Remaining calm under pressure, never saying ‘no, we can’t do that,’ and figuring out how to solve the situation, were skills that helped me in Iraq and to this day” Bob continued to work at the jewelry store during breaks all through college.

Bob’s father, meanwhile, was constantly juggling various side jobs and hustling to make ends meet. He worked construction, and when one job ended, he was immediately finding his next paycheck. “He had a wide variety of roles,” says Bob, “including catering, working at a muffler shop, and eventually working as a project manager. If he lost a job he would immediately jump in and find something else, he was always keeping busy and always trying to improve himself. I learned that from him.”

As a kid, Bob was more interested in video games than most team sports. He developed a particular affinity for games that challenged him to think strategically—a skill set he would later use throughout his career to both manage intelligence operations and guide small business to success. “A lot of those games are about resource utilization,” says Bob, “you have resources you have to mine or harvest, and then allocate. I think I kind of got started there, in that kind of thinking.” Meanwhile, at school, he developed a strong interest in math and physics. At the age of 10, he stumbled upon a physics book called About Time, and although many of the concepts were beyond him, he became fascinated with the subject.

In high school, Bob finally developed an interest in a sport; but as might be expected for him it was a bit off the beaten path. Fencing became a major part of his high school career. He competed in national tournaments, served as the captain of the Varsity team during junior and senior years, and ultimately even tried out for the Olympic fencing team. “It’s an extremely strategic game,” says Bob, “some people call it physical chess. You have to anticipate the opponents’ movements. I didn’t know anything about it when I started but happened to be pretty good at it. And I loved the strategy of it, the competition, and winning.”

When it came time to apply to college, Bob knew his parents hadn’t saved money for him to attend, and that he wanted to avoid taking on student debt. Therefore, the military seemed like a natural fit, and he entered the ROTC program at the University of Buffalo. He majored in mathematical physics, a joint program between the math and physics department. As always, he found himself in uncharted territory. “The school was large, it was a 35,000-person school,” says Bob, “and out of 35,000 people, there were only ten people with my major across four years. So it wasn’t a very big department! But it was a great program.”

“The T-shirt is a reminder of how the Army ROTC experience helped accelerate my interest in the military and in leading and achieving.”

ROTC was similarly challenging with its rigorous academic and physical requirements. Bob particularly remembers an event called the Ranger Challenge as a formative experience. Teams of cadets in Ranger Challenge competed to climb ropes, run, shoot, assemble weapons, and perform other feats. “I still have the T-shirt my team members and I wore,” Bob says. “The T-shirt is a reminder of how the Army ROTC experience helped accelerate my interest in the military and in leading and achieving.”

After college, Bob received his first duty assignment at Fort Lewis, Washington. “They were standing up a new unit from nothing,” recalls Bob. “It was a new type of unit called a Striker Brigade. I got there and there were literally 10 people in the whole unit out of 3,000. There wasn’t a lot to do initially so I took the opportunity to expand upon my knowledge base and skills. I took a lot of intelligence training classes, interrogation classes, and forensics classes. You name it, I took it.”

Over time, soldiers began to arrive in Fort Lewis and Bob was assigned to be a Signals Intelligence Platoon Leader. Building the unit proved to be a real challenge, not least because the resources allocated to them were sorely out of date. “The equipment was from the Cold War period,” says Bob, “and was not designed for counter-insurgency operations. And as I was learning more about what was happening in Iraq, I knew the equipment we were given wasn’t going to cut it.” Once again, Bob sought out a challenge, and began studying counter-insurgency warfare.

“My non-commissioned officers and I helped design a program to train all the soldiers to address this new issue, this new type of warfare” says Bob. “I actually consider this one of the more entrepreneurial things I’ve ever done, because I really went against the grain and I got a lot of flak for it.” Bob took it upon himself to cross-train his soldiers and turn them into analysts.

Therefore, when Bob and his Signals Intelligence Unit were confronted with equipment shortages and a lack of guidance, they were prepared to face it head-on. Fifteen months later they won the NSA Director’s Trophy and Bob was approached by the NSA Director and asked what he’d like to do next. When Bob replied that he’d like to work at the NSA, the Director assured him he would make it happen.

Bob was moved to Fort Meade and, again, began learning an entirely new skill set. “I went from a very tactical job to a very strategic job,” he explains, “gathering intel and doing intel work that was literally being briefed to the President.” As a Captain, he was the youngest person on staff, but quickly distinguished himself. He became Company Commander for one of the cyber companies at NSA, and took on an additional intel job to insure he understood the workload of his soldiers.

In 2011, Bob chose to leave the military but remained at NSA. “I basically left one day, and came back doing the same job in a suit instead of a uniform,” says Bob. He stayed there for two more years as a civilian employee at NSA, but ultimately he again began thirsting for new experiences. “I was observing a lot of cyber attacks that were occurring against the private sector,” reflects Bob. “NSA is a big national strategic asset, and it’s not designed to respond to attacks in the private sector. We were ill equipped to handle the situation, and I realized there was a need in the marketplace and that the private sector needs this skill set.”

From this thought, Bob’s small business was born. Founded in 2012, Ronin Analytics employed four staff and worked to provide threat assessment services. “We would simulate what an attack would look like from an adversary,” says Bob. “We did some technology integration and had money coming in, but it was a very crazy situation. I jumped into the private sector without really knowing anything about how to run a business or, how to sell anything. I realized we needed to look at scalability and create some type of product.”

The Ronin team came up with something called CTOC, Cyber Threat Operations Center, which was essentially a security operations monitoring center. “Think of an antivirus software,” says Bob, “but something that had a lot more capability to monitor specific issues on a machine.” As Ronin explored options to get capital, a company called Cyber IQ offered to buy the business and help them scale up. “The deal was, I’d come on as an executive at the company, take some stock, our investors would be paid off and everything would be great,” says Bob, “but then basically Cyber IQ ran out of money in about six months.”

Right as Cyber IQ was shutting down, Bob happened to give a presentation at Bloomberg, where the Chief Risk Officer offered him a job on the spot. For a year Bob worked in cyber intelligence for the company, but the 4-day a week commute to New York from DC began to wear on him.

In 2015, he was recruited by IBM for a product management position. “It was a very interesting role and learning experience,” says Bob. “I had been looking for a product manager role. We launched the new product and in the first year took it from $0 to $45 million. I learned how to launch a global product and how to sell in many different markets.”

After two years in that role, Bob transitioned to another job within IBM, as the Chief of Operations for the X-Force Threat Center. There, Fortune 500 companies trained their staff in a cyber-threat simulation program. “That was interesting, but I didn’t really love living in Boston,” says Bob. “It was then that I got an offer from Dreamit. I had been aiming my career toward venture capital but wanted to have a tactical background and some experience in project management. Having my own business and the experiences at IBM made me the ideal candidate for Dreamit and Secure Tech.”

Always be learning, always challenge yourself, always jump into things that make you feel uncomfortable.

To young people just now launching their careers, Bob offers the advice he always followed himself. Never rest on your laurels. “It’s one of the biggest mistakes you see people make,” he warns. “Someone who’s accomplished something interesting early in their life and, they’re just sort of staying alive until 65. They’re sitting by, they’re not making themselves better, and they’re not learning about new industries and sectors. Always be learning, always challenge yourself, always jump into things that make you feel uncomfortable. I’ve always found that when I’m in a job, and I feel like I’m static. When I’m not learning anything anymore, it’s time for a change.”

Bob Stasio

Gordon J Bernhardt


President and founder of Bernhardt Wealth Management and author of Profiles in Success: Inspiration from Executive Leaders in the Washington D.C. Area. Gordon provides financial planning and wealth management services to affluent individuals, families and business owners throughout the Washington, DC area. Since establishing his firm in 1994, he and his team have been focused on providing high quality service and independent financial advice to help clients make informed decisions about their money.

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