An Entrepreneur’s Odyssey: Bootstrapping a Small Business in Government Contracting
Bootstrapping a small business in government contracting wasn’t necessarily my lifelong dream. It’s what came about when no company would hire a disabled combat veteran and his spouse after the war. We’d exhausted all military transition resources available through the DoD, the VA, and the multitude of nonprofits always raising money for the military community and walked away with the same conclusion: if we wanted to work, we were going to have to hire ourselves!
What we lacked in experience on the backend of how the federal program worked, we had first-hand experience of the consequences lapses in the public sector have on those whose lives they are entrusted. Agency failures resulted in casualties of people we loved, healthcare negligences left us with permanent scars, and scrupulous vendors monopolizing contracts while simultaneously delivering the lowest-quality of service cost people their lives. We knew we could learn how to build a government contracting company that did better.
However, ask anyone who’s set out on the quest to bootstrap a government contracting firm, and you’ll hear a similar story: it’s not easy…there’s so much bureaucracy…the process is slow…it’s rigged toward the big primes… it’s incredibly difficult to break in!
While we encountered many challenges along the way (and, if I’m being honest, probably uttered more than one of the sentiments above), we found a way forward — around and over the multifaceted, bureaucratic challenges on the gov-con odyssey as a bootstrapped, family-owned, veteran-owned small business. We had no special network connections, no War College degrees, and no employed experience with on-the-job training on how to build and grow a government contracting firm. We just had determination, dedication, and a willingness to learn along the way, even when the learning process was delivered via ego-bashing, public gut punches.
There are a lot of myths, legends, rumors, and tall tales about how to succeed as a small business newcomer in the highly competitive world of federal government contracting. I explored many elements of this misleading advice on my quest for success and walked away with a bruised ego on more than one occasion. However, eight years into my persistent pursuits, our bootstrapped company started winning prime contracts and has continued to see success on this front. Every failed proposal and pitch taught me something about the path necessary to cross the valley, scale the mountain, and build a solid foundation for long-term gains in an uncharted environment.
There’s an old saying, "Good judgment comes from experience... and experience? Well, that comes from bad judgment."
May this consolidated collection of lessons learned from my bad judgments provide some value on your entrepreneurial journey.
Lessons Learned from My Experience Bootstrapping a Small Business in Government Contracting
Here are a few lessons learned from my experience bootstrapping a small business in government contracting:
Government contracting isn’t easy, but it’s not impossible.
It’s not easy to bootstrap a small business. For many entrepreneurs, success is long in coming. You find yourself burning through resources you don’t really have to spare with little to no return. You start to feel stupid, trapped, and destined to fail with every sales pitch and proposal that does not result in a “win.” In my experience, very little of entrepreneurial success is sequential or proportional. Unlike academic programs, corporate structure, and military rank promotions, entrepreneurial success is often not incremental success built upon incremental success, with a few setbacks sprinkled in for good measure. Instead, entrepreneurship is complete and total BOMB, after complete and total BOMB, after an even more painful complete and total BOMB that has you questioning your sanity for ever thinking this was a viable career option.
There’s no boss to submit your resignation letter to, to make the pain end – you’re stuck with all of it – making it a success or digging yourself out of dismal failure. There’s no passing the buck, blaming someone else, or springboarding your career’s next step off another’s back. It’s just you and your near-sighted business idea that isn’t working. It’s these moments, months, or years of limited harvest that make or break your entrepreneurial success. Sure, bootstrapping a small business in government contracting isn’t easy! If it were easy, everyone would be doing it, and it wouldn’t be profitable. Entrepreneurship is difficult, and those who are able to navigate the struggles that accompany this journey are the ones who succeed in the long run
Navigating never-before-encountered challenges of entrepreneurship doesn’t “feel” good. But it’s doable if you do what it takes to do it. The lessons you learn in the process will provide you with the skills and insights needed to replicate your success over and over and over. Teach yourself how to write incredibly detailed government proposals, enrich your mind with the ins and outs of the Federal Acquisitions Regulations (FAR), and figure out ways to operate in an agile, ethical, effective manner that will set your company up for success. It takes time to build something worthwhile, and the drudgery that we so often associate with government contracting is part of the process that hones your skills and expands your capabilities.
People, Programs, and Processes are essential in government contracting.
I like doing things by myself, for myself. I err on the extreme side of self-reliant, and self-starter, as many entrepreneurial types tend to be. When encountering the friction that working in a group tends to introduce, I frequently find myself saying, “It’d be easier if I just did it myself.” While this lone wolf method may work in the early days of conceptualizing and launching a new business, it can be incredibly stifling to growth as you look at expanding your operation beyond that cluttered corner of your basement “office.”
Recognizing my own Achilles’ Heel, I prioritized three P’s in my government contracting journey – people, programs, and process. I found mentors with experience in government contracting who gave me the “cold hard truth” on my latest and greatest business ideas – pointing out weaknesses and vulnerabilities in ways I could strengthen these areas or scrap the whole hare-brained idea and refocus. We consumed all the free government contracting training available (it’s available to all of you, too, through the SBA, APEX Accelerators, and SCORE!) and worked multiple additional jobs to pay for life during this time of professional development. Then, once we found a way forward – one that resulted in winning contracts, delivering high-quality service, and earning stellar performance ratings – we formalized these methods into a process: something replicable and continuously revisable as needed.
As a side note, my “feelings” about the company’s success or lack thereof did not accurately reflect the reality. Some days, I was hopeful for the future; others, I scrolled job listings on Indeed, trying to find a way out of the self-employed sinkhole I felt trapped in. Now that our company has crossed that initial chasm, I can look back with both perspective and realization that facts trumped feelings, even on the worst of days. The disappointments along the way weren’t as bad as they seemed at the time, and winning contracts came down to effective capture processes, stellar proposal writing, economic pricing strategies, qualified personnel, and good past performance reviews rather than American politics, nepotistic network connections, or what some random commander thought of my multi-domain solutions.
What worked for others may not work for you.
When we founded our company, everyone told us to subcontract with the big primes. “This is how you build past performance,” “Subcontracting is the only way to grow your company sustainably,” “Everyone that breaks into this space starts as a subcontractor” was the advice given to me by people who knew more than I did about business, entrepreneurship, and government contracting. So, I focused my strategy on meeting primes, pitching primes, and trying my hardest to get on as a subcontractor. Resources I didn’t have – time, money, and energy – were all burned trying to follow the seemingly sage advice of those who had gone before me. I followed their recommendations, down to what to wear, who to talk to, and how to pitch, and absolutely nothing good came out of it.
The big primes stole my intellectual property, contacts, strategy, and, in one especially unethical case of “beltway banditry,” my entire Technical Approach from a proposal. They’d win contracts with my company named as a subcontractor (because we had the stellar resumes, the cutting-edge strategy, and would write nearly 100% of the proposal) and then give us none of the work. When I’d push back, they’d throw their six-person Ivy-League-educated in-house counsel team at my bootstrapped, family-owned small business, threatening in convoluted legal language to “eat us for lunch” and drive us out of business via legal fees. After years of this unproductive David-and-Goliath dynamic, we decided to do things our way. Forget subcontracting…we submitted as primes, and guess what? We started winning!
Just because most folks do it one way, doesn't mean that way will work for you.
Entrepreneurship, by definition, is doing things differently! Think about the box, try new approaches, and figure out how to make it work.
Final Thoughts - Government Contracting Success
Bootstrapping a small business in government contracting has been a good career move for me. While the circumstances of life that have accompanied me on this journey – war, health challenges, limited resources, etc. – were less than ideal, we made it work in a way that supports a sustainable life for our family in rural America. I like the people I have the honor of working with in this sector, I enjoy the challenges government contracting brings (it’s like a real-life Rubik’s cube!), and I find the opportunity to support the public sector very fulfilling.
If you’re interested in government contracting, I encourage you to strike out on the trail, adjust your journey (and yourself!) as needed, and keep persisting until you summit the mountain.