Growing up on a remote ranch in East Texas, where long hours were spent doing thankless work that never seemed to end, Rob Rosenberger learned how to dream big. He hated tending cattle, fixing fences, cleaning stalls, and the fact that working extra hard one day didn’t make the next day any easier. “I knew that if I stayed on the ranch, it would be the same thing until the day I died,” he remembers now. “The world to me was a huge, mysterious, exciting place of opportunity with so much to see and experience—I wanted it all. If I ever got the chance, I was going to do something different with my life.”

There wasn’t much to aspire to in Wells, his small town of 926 residents. But on TV, he saw business executives wearing suits to work instead of blue jeans. Like them, he dreamed of becoming a successful business leader, and maybe one day starting his own company. “At a young age, I never thought those things would actually happen,” he says. “I would take my business ideas to my father, who would promptly shoot them down by pointing out the logistical flaws. If I wanted to mow lawns, whose lawnmower would I use, and how would I transport it? The list of flawed concepts presented to my father seemed endless. Discouraged, I had no idea how to even get started.”

Rob was completely caught off guard and unaware when, at nine years old, his father took him along on a drive in his truck pulling a flatbed trailer. He had learned that on such drives, he was not to speak unless spoken to, so he didn’t ask where they were headed. “I was shocked when we ended up in the middle of an endless watermelon field,” he says. “I didn’t know such a thing even existed. There were thousands of watermelons everywhere, with workers loading them onto diesel trucks idling in a line. I was even more surprised when my father’s truck and trailer were pulled into the line and the workers filled up our trailer.”

On the ride home, Rob’s father finally broke the silence. “You wanted a job?” he asked. “I got you a job. You wanted to make money and this is how you’re going to do it—by selling melons.” Rob had no idea how, so his father took a black magic marker and wrote a dollar value on each melon. He explained to Rob that he had bought a hundred melons for a dollar apiece, and that he expected $100 returned at the end of the summer. “I was paralyzed, speechless, and overwhelmed,” he recalls. “I didn’t even know enough to be scared.”

With that, Rob embraced entrepreneurship under the blazing Texas sun, selling watermelons aside the major highway that ran by their ranch. His father would park the flatbed roadside in the morning, and Rob would sit there all day, aiming to hit the number scrawled in black for each sale. By the end of the week, he had sold all hundred melons, and he was ecstatic. “I felt like David and Goliath,” he proclaims. “I had accomplished the impossible, doubling the investment in the process.”

With just that minimal experience, Rob began to understand how to look people in the eye, read a situation, and negotiate. And when he tried to pay his father back, he learned another valuable lesson. “I said you didn’t have to repay me until the end of the summer,” his father insisted. “You can do anything you want with that money until then.” Finally, the light bulb went off in Rob’s head, and he realized he could invest in more watermelons.

By the time autumn rolled around, Rob was turning around roughly a thousand melons a week. He did it the next summer, and the summer after that, growing more adventurous each year. By the age of fifteen, he had scaled to essentially become a wholesaler overseeing up to 42 workers, buying up various farmers’ fields a year in advance like commodities or futures. At sixteen, he bought a used red Porsche convertible, and in two years, he had options on approximately one thousand acres of Texas melons—a 24/7 operation.

Now the co-founder and CEO of Blackdragon, a platform company operating in the government contracting space, Rob has come a long way from the sun-drenched melon fields of rural East Texas. And though his risk-embracing ambition has been refined with experience and time, he’s dreaming bigger—and doing bigger—than he ever thought possible. “As it turns out, I’ve been blessed to have actually done most everything I wanted to do,” he affirms. “When I was a flyer in a Navy reconnaissance squadron, my commanding officer joked that I accomplish impossible things because I’m too stupid to realize they can’t be done. That may be true, but all of the big challenging and defining moments in my life have only reaffirmed my big dreams.”

Acting as matchmakers between sellers and buyers, platform companies like Blackdragon aim to link up non-monetized resources or assets with people who value them, facilitating a transaction. Examples in the private sector include eBay, Amazon, Match.com, and many other hubs, marketplaces, and apps. “Uber, for instance, takes a parked car and monetizes it by putting it into play via technology,” Rob explains. “The haves and the have-nots find each other, and the platform facilitates the transaction.”

Launched in January of 2015, Blackdragon acts similarly in the government space, connecting a large ecosystem of freelance expert consultants with companies to bid on government contracts. Unlike other sectors across the business landscape, which have evolved with time, government contracting is archaically bureaucratic, routine, and process-oriented in many ways. The company seeks to change this by monetizing underutilized assets within the ecosystem. “Often, winning a specific target contract comes down to who you know, what you know, and what you know how to do,” Rob points out. “Based on the needs of a given contract, our platform quickly pulls together a dream team of 1099 experts that seem like a good fit. Then, from a list of bidders also selected as potential good fits by the platform, they get to choose the bidding company they think they can win the contract for.”

These selections are based on complex algorithms and modeling that essentially supplants conventional industry practices, which are serendipitous, unpredictable, inefficient, time-consuming, and based on inconsistent, capricious arrangements of interpersonal relationships. Blackdragon’s data-driven modeling completes in seconds, minutes, or hours what used to take days, months, or quarters, often in greater volume at lower costs and with higher accuracy.

Once a bidder and team come together, the team partners with the client in a complementary way to conduct full-spectrum efforts necessary to win the contract. “They form themselves, manage themselves, and even pay themselves,” Rob explains. “In this way, we’re transforming the paradigm by rewriting the power rules. Before, you had to either work for the government or work for industry as a full-time employee or 1099 if you wanted to monetize your assets. But with Blackdragon, individuals can proactively monetize and then maximize their respective market value by anticipating good-fit opportunities through modeling the patterns and intentions of Congress and forecasted agency spending.” Teams work on a shared risk, fixed fee basis with some or most of that fee placed into contingency. They must win the contract to collect the full fee. Consistent with other popular matchmaking platforms, the company is paid via a small slice of each transaction facilitated between buyers and sellers.

Taken together, Rob has worked on over $30 billion worth of contract pursuits and has been affiliated with thousands of proposals over the course of his career. Through it all, he identified one common thread that unnerved him. “I realized that nobody enjoys the bidding process,” he says. “Even the people who do it full-time with a smile on their face would choose to do it differently, if given the choice. Blackdragon is here to give them that choice by switching up the model, putting consultants in charge to act creatively and resourcefully to win for the good of the whole team. That’s why our flagship offering is called, ‘Winning as a Service (WaaS©).’”

Creativity and resourcefulness have been hallmarks of Rob’s own work ethic, rooted in his childhood as somewhat of an outlier in his ranch-oriented family. His father graduated from Texas A&M with the dream of being a professional cowboy, he tried to make money rodeoing. His mother grew up as a city girl in Houston but always loved horses, and participated in rodeo pageants. “They loved working with their hands, being free, calling their own shots, and living with horses,” he recalls. “My sister got a lot of that same spirit, and is now in the top tier of national rodeo professionals, with a huge private equestrian facility in Texas. She also started her own nonprofit Christian ministry that uses horses and rodeo to reach others with the message of Christ. I’m very inspired by her.”

Rob was also inspired by his grandparents, who were his first role models of strong and routine faith. He spent significant time with them growing up, and noted how they always read the Bible and prayed before meals. He admired their conviction, but didn’t fully understand it until he was sent to a one-week church camp when he was eleven. “I thought I was being punished,” he laughs. “I just wanted to sell watermelons. My parents made me go, and thank God they did, because on the last night there, the sermon completely changed me. It was defining, piercing, and permanent. It saved me. The next morning, when I had to leave, all I wanted to do was stay and learn more. Since that time, I’ve had a devotion to God that drives and centers everything else in my life.”

From that day forward, Rob’s whole attitude toward faith and serving others changed. Church took on a whole new meaning, and became a central focus of his life along with business and sports. He enjoyed basketball and soccer, but baseball was his true passion—a bond he shared with his grandfather, who had briefly been a professional baseball player during the Depression. “I learned that what I really liked about sports was the competition,” he says. “And I didn’t just want to compete halfway; I wanted to win by the maximum amount every time.”

Through his elementary school years, Rob was first in his class every year. He graduated high school in a nearby town, where he continued to make good grades with minimal effort. His family wanted him to attend college, but he thought he already knew everything there was to know about life and earning a living. Then, when he was nineteen, a drought struck, and the melons didn’t grow that year. “I had over-bought all the fields, and I still had to pay,” he remembers. “I failed horribly and finally realized that maybe I didn’t have it all figured out. I had taught myself everything I knew through grit and hard knocks, but maybe there was something else to learn.”

With that, Rob enrolled last-minute at Texas A&M, his father’s alma mater. At his father’s dare, he also joined the Corps of Cadets to prove he could cut it—a decision he regretted the second he showed up for ROTC. “That first experience as a freshman was hell. Freshman cadets aren’t even allowed to have first names—we all shared the same first name ‘Fish’,” he reflects. “I had always been the one in charge, but now I was at the very bottom of the totem pole. It made me conform, when I wanted everyone else to conform to me. But it was one of the best things to ever happen to me. It deepened my faith even further, and I learned how to operate not as an individual, but as a unit. Our uniforms featured the Latin phrase per unitatem vis, or ‘Through unity, strength.’ I built my company around that same concept, and made enduring bonds that have lasted a lifetime.”

Despite the benefits of the program, Rob struggled financially, and his grades suffered as a result. He left college his junior year to enlist in the Navy, where he flew top secret reconnaissance missions from 1990 to 1995. He then returned to A&M with a renewed and fierce commitment to academic excellence. “God had given me a second chance at life, and I was now married to a beautiful woman who was counting on me,” he says. “I couldn’t fail her, and I couldn’t let my family down. I was also very mission-focused, with the goal of getting a job at the CIA because I had loved spy movies and books growing up.”

Dreaming big and doing big, Rob completed a bachelor’s degree in business with dual majors in management, and finance, along with dual minors in accounting and electrical engineering. In 1997, he was hired by the CIA to do contracts and negotiations, where he was put on multiple rotations in other intelligence agencies. In his spare time, he also earned multiple professional certifications and completed four graduate programs from local universities. “I loved the mission and the autonomy I had to get the job done,” he says. “I was one of the few contracting officers who actually traveled the world frequently, working directly with other entities on these transactions.” In that capacity, he became an expert in contracts, especially merit-driven, performance-based contracts, and invented a new hybrid contract type that was better, faster, cheaper, and more user friendly than other options on the table. “When I realized I could solve complex problems by transforming routine, static business protocols into something creative and unprecedented, I was on my way,” he remembers.

Rob decided to leave the agency in 2003 when the atmosphere began to feel too constraining to the free flow of his unconventional ideas, taking a job under the Joint Staff Comptroller in the Pentagon as Special Advisor to the Chairman of the Joint Chiefs of Staff on acquisitions and procurement as a contractor. Two years later, he was recruited by SAIC, where he worked at DIA. “I was willing to take on any problem, no matter how ugly,” he recounts. “I wanted the hardest job I could find—the job where I was guaranteed to lose. I thought I could do it, and I saw each challenge as an opportunity to grow. It was hard, but I gained far more than I would have otherwise.”

In 2010, Rob took an executive role at a company called Tetra Tech, and later became a consultant to Northup Grumman. Several months later, he was offered a new challenge by NCI to be the senior VP and GM of their intelligence group. He was laid off the following year, a jarring experience that led him to a position in August of 2012 at a company called DMI. There, he witnessed astonishing growth rates as the company exploded from annual revenues of $16 million to over $300 million within a five-year period. This staggering success was enabled by a fascinating proposal center built and managed by John Fanguy, an unparalleled innovator who later left the industry to become an angel investor in technology start-ups. “When I decided to start Blackdragon, I knew John was the perfect person to do it with,” Rob says. “We founded it together, and he’s now the COO. None of this would be possible without him.”

After DMI, Rob worked a short stint as COO at Metters Industries that wasn’t a good fit. Exasperated with the federal industry, he commenced a period of soul searching, taking a break from his brooding to attend DC’s annual Texas State Society barbeque for Father’s Day with his family. There, he noticed someone wearing a Texas A&M ring and struck up a conversation, only to realize it was an extended family friend from his hometown. “The young man introduced me to his boss, a Texas Congressman I had long revered,” Rob recounts. “As the conversation evolved, I was a bit too outspoken about my frustrations with Congress, and quickly apologized. But the Congressman appreciated my candor and passion for the subject so much that he offered me a part-time job on his staff while I figured out my next moves.”

Over the next fifteen months, Rob created a self-initiated innovative work product that was used for the basis of new legislative efforts across the House and Senate. After coming up with 36 separate idea memos on his own prerogative in a single month, he wanted to do it again, only bigger and better. Using his Congressional credentials, he started quietly outreaching to agency leaders, military brass, and CEOs of various corporations. “I asked them what law they’d want changed if they were king for a day,” Rob says. “I’d ask for 30 minutes, but these top C level agency directors, presidential appointees, and CEOs would give me multiple hours, speaking freely about their visions for improvement. It was really remarkable.”

With this raw, invaluable feedback and extraordinary vantage point, Rob came up with 160 recommendations for new legislation over a three-month period, validated them, and drafted ‘proposal-formatted’ memos framed in the context of existing law. And with time, his mathematic and logic mind began detecting patterns. “I saw what the government, Congress, and industry were trying to do, and what unemployed people were trying to do in the middle of all that, suffering the wrath of the misalignment,” he says. “The solution was a marketplace platform that changed the incentive structure and converged these interests in a new way. That epiphany is now Blackdragon.”

Now a bootstrapped, cash-flow positive company of almost 1,200 consultants and hundreds of clients in its first three years, the company has risen to become the foremost group of for-profit bid and proposal (B&P) experts throughout the federal industry (if not the world). Although running the company is an all-engrossing feat, Rob still finds time for his wife, Jamie, and four daughters. “Parenthood can be the easiest or hardest part of my day, but it’s always the best part of my day,” he affirms. “And I’m incredibly grateful to my wife for not only putting up with the fever-pitched pace of my never-ending entrepreneurial ambitions, but also guiding and nurturing them. She’s one of the few people that can actually get me to be a little less rebellious and a little more reasonable.”

In advising young people entering the working world today, Rob says that if you’re looking for your dream job, you’re looking for the wrong job. “Every job is a piece of the dream job that takes you to where you want to go. There’s no perfect job unless you make it such, and frankly, the job is more about the person doing it than it is about the requirements written on paper. So, own it. Make it all about what you can do with it. And don’t always fall for the easy ones, because they often come up short. Don’t be afraid to fail, because that’s how you truly grow and advance in life.”

Rob is held to this advice in his own life by the internal clock that warns against comfort and complacency, always driving him forward to the next challenge. And in Blackdragon, he’s taking on his biggest impossibility yet. “When we first started, it felt like steering the Titanic with a toothpick,” he says. “It seemed like an impossible task, but that’s what I live for. We have an opportunity to fundamentally transform an industry that’s in desperate need of change, but we’re doing it in our own way, outside of bureaucracy,” he says. “We’re not just dreaming it; we’re doing it. We’re owning it because we know what needs to get fixed. To get to witness that paradigm change is really something. It’s a privilege I will always treasure.”