Blog post provided by Fred Diamond, Founder, the Institute for Effective Professional Selling
Northern Virginia has long been one of America’s premier regions for innovation, government contracting, and entrepreneurship. It’s also home to thousands of military veterans who continue serving our nation by building companies, creating jobs, and solving some of government’s most complex challenges.
Recently, I had the opportunity to interview fellow Northern Virginia Chamber (NVC) member Jared Shepard, CEO of Hypori, for my award-winning Sales Game Changers Podcast. I first met Jared after hearing him speak on a Chamber panel about veteran entrepreneurship. His comments were refreshingly direct. Rather than offering motivational sound bites, he shared practical lessons drawn from more than two decades of building successful companies after his military service.
Jared’s story is remarkable. A former Army infantryman and IT professional, he founded Intelligent Waves before launching Hypori, one of Northern Virginia’s leading cybersecurity companies. Along the way, he also created Warriors Ethos, a nonprofit dedicated to helping veterans successfully transition into civilian careers.
While much of our discussion focused on military veterans entering government contracting, his advice applies to every entrepreneur and business leader, whether or not they’ve worn a uniform.
Business Success Requires Different Skills
One of Jared’s first observations challenged a common assumption.
Military service develops remarkable leadership skills. It teaches accountability, mission focus, teamwork, resilience, and the ability to make decisions under pressure. Those qualities provide an incredible foundation for entrepreneurship.
But they don’t automatically prepare someone to run a business. Far from it.
Jared said, “The military teaches mission and people exceptionally well. It doesn’t teach money.”
Unlike the private sector, military professionals aren’t measured by quarterly revenue, profitability, cash flow, or customer acquisition costs. Those realities become unavoidable the moment someone starts a company. That’s why Jared offers advice that surprises many aspiring entrepreneurs: don’t rush into starting a business immediately after leaving military service.
Instead, he advises spending a year or two working inside a successful commercial organization. Learn how businesses operate. Understand finance, sales, operations, hiring, and customer relationships while someone else carries the financial risk.
It’s practical advice that dramatically improves the likelihood of long-term success.
Successful Veteran Entrepreneurs Think Differently
Throughout our conversation, one theme surfaced repeatedly: successful entrepreneurs think differently about risk, learning, and leadership.
Jared often asks veterans a simple question: What does it really cost to start a business?
Most people answer with a dollar amount. His answer is different.
“It costs time and risk.”
Before launching a company, entrepreneurs need to honestly assess their personal circumstances. How much time can they truly devote? How much financial and personal risk can their family absorb? Do they have a compelling reason customers choose them over established competitors? Passion alone isn’t enough.
Every entrepreneur must clearly answer another critical question: How will you differentiate yourself?
If you can’t explain in seconds why your company is uniquely positioned to solve a customer’s problem, it’s time to go back to the drawing board.
Jared also stressed seeking mentors who have already traveled the road you’re about to take. Rather than chasing celebrity CEOs, find leaders who recently built companies at the stage you’re entering. Their advice will be practical, relevant, and immediately applicable.
Finally, know your weaknesses. After more than twenty years as a CEO, Jared says the biggest lesson he’s learned is to hire people whose strengths complement your own. Great companies aren’t built by leaders who know everything. They’re built by leaders confident enough to surround themselves with talented people who know more than they do.
Lessons Every Northern Virginia Business Leader Can Apply
Although our discussion centered on veterans, I kept thinking about the broader Northern Virginia business community. Whether you’re leading a government contractor, a technology company, a professional services firm, or an emerging startup, Jared’s lessons remain remarkably relevant.
- Great leaders never stop learning.
- They stay humble enough to seek advice.
- They continually build stronger teams.
- They understand that winning one contract, hiring one great employee, or achieving one successful year isn’t the finish line.
As Jared reminded me, business never gets easier. It simply becomes more complex.
That perspective is especially important today. Artificial intelligence, procurement reform, cybersecurity, and changing customer expectations are reshaping every industry. Organizations that continue learning and adapting will thrive. Those that become comfortable risk falling behind.
One of Jared’s final recommendations captured this perfectly. Every business leader should understand how emerging technologies, especially AI, impact their customers and be able to explain how their company reduces cost, friction, or complexity.
Ultimately, that’s what successful businesses do.
As someone who has interviewed over 1,000 executives on the Sales Game Changers Podcast, I appreciated Jared’s honesty. His message wasn’t about shortcuts or overnight success. It was about disciplined leadership, continuous learning, surrounding yourself with exceptional people, and remaining relentlessly focused on creating value for customers.
Those principles helped him build outstanding companies.
They’re also principles that can help strengthen Northern Virginia’s business community for years to come.
Fred Diamond is the host and producer of the award-winning Sales Game Changers Podcast and the Founder of the Institute for Effective Professional Selling (IES), a member of NVC.
He is the author of Insights for Sales Game Changers: Lessons from the Planet’s Top Sales Leaders, which features sales improvement tips and ideas from over 450 Sales Game Changers Podcast episodes.
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