Leadership
Some leaders build companies. Others build a community. Shana Cosgrove, CEO of Nyla Technology Solutions, is doing both. She had a vision: bring together a group of high-performing professionals in the DoD tech space. Not for panels. Not for pitches. Just space—to connect, relax, and actually get to know each other. She made the call. Reserved the rooms. Took the financial risk. No guarantee anyone would come. But they did. Over 20 talented, accomplished leaders showed up.What happened? → Meaningful connections.→ Candid conversations.→ A powerful ecosystem of Maryland, DC & Virginia tech talent—off the grid, but fully plugged in. At the heart of it all: Shana. Taking the mic. Sharing her journey. Strong. Vulnerable. Honest. That’s leadership. Not the kind you read about.The kind you feel when you’re in the room. The best kind of leadership often begins with a risk – and no guarantees.
Problem Solving
🚨 True story from Detroit — I asked three different twenty-somethings for directions to a restaurant two blocks away!Google Maps was spinning because of the tall buildings, so I figured I’d ask a human.Not one could help. Not even close. It hit me like a brick: we’re facing a crisis of resourcefulness.And it’s going to cost us—big time. Problem-solving, critical thinking, follow-through—these aren’t just “nice to haves.” They’re career-defining skills. They’re what fast-track employees have that others don’t. So, I’ve made it my mission to teach these skills to my kids. At our house, the rule is simple: each of my kids pays half their college tuition.Sounds tough? It is. That’s the point(I’m not as mean as I sound – they had a phenom k-12 and any scholarships go to their half first 😊). Here’s how my son handled it: 📍 Private college. Full room and board. Max meal plan.📍 He owed about $5,000 each term (after merit scholarship).📍 Instead of using his summer job money, he took out a loan—on the last day, with zero research.📍 The interest rate? 12.65%. 😳 That’s $1,700 in interest before even touching the principal. I didn’t fix it for him. I sent him back. He had to:🔍 Dig deeper📄 Research the FAFSA💡 Discover he qualified for a federal loan at half the rate🏦 Cancel the first loan✅ Follow through and pay the bill That’s resourcefulness in action.And it’s exactly what the workforce—and the world—needs right now. 🛠️ We don’t need more instructions.We need more people who can figure it out. And, yes, while the system for paying for college is broken, he needed to work with what is available to him.
Resourcefulness
My first job as CEO came with zero salary.I had to raise money not just for myself — but for the whole founding team. That wasn’t the plan. I’d dreamed of Apple. Microsoft. IBM.But those companies weren’t looking for someone who was waiting tables instead of going to college. (I did get an MBA later – without college – but it didn’t sway them) What I didn’t know:While I was refilling coffee and memorizing orders, I was building something powerful. ✅ Executive functioning✅ Emotional intelligence✅ Grit But there was one skill that made the biggest difference — and hardly anyone talks about it: 👇 RESOURCEFULNESS 👇 It’s not: ❌ Funding❌ Fancy résumés❌ Prestigious connections It’s the ability to figure things out when nothing goes to plan.And the good news? You can train it. In the age of AI and instant answers, we’ve confused access to info with ability to solve real problems. But the most powerful search engine?Your own brain. Here’s what real resourcefulness looks like:✔️ Trusting yourself when the path isn’t clear✔️ Trying again — even after failing publicly✔️ Staying calm when plans blow up✔️ Asking better questions✔️ Adapting faster than your fear This is how humans survived before Google, GPS, or ChatGPT. Today, it’s a superpower — and one of the most undervalued leadership skills there is. 💡 Want to build your resourcefulness muscle? Try this: 🎯 Learn a new sport or hobby🤝 Go to an event where you know no one📺 Watch the news channel you disagree with🛑 Don’t buy anything new for a week Confidence comes from trying.Resilience comes from discomfort. Resourcefulness? It’ll set you apart in a world of shortcuts.
Equity
I almost left a negative comment on a recent VC advice post. Something I usually don’t do. The author insisted that founders should “lay down the law” on what terms are acceptable from investors. Bold take. Misleading too. Here’s the truth: If it’s your first round, and they have the money—you’re not dictating terms (there are rare exceptions, keyword: rare). Raising venture capital isn’t just a negotiation—it’s a relationship. And it’s not symmetrical. I once had an investor call me 17 times in one day—while I was hosting a summer cookout with my team—because I hadn’t closed the next round. Pressure? Yep. Helpful? Nope. Here are a few truths I learned the hard way: ✅ The right investor is your partner, not just your ATM.If they can’t stomach risk, they’ll micromanage your every move. The right investor will be here for it – and bring clear value. ✅ Not all money is equal.I once took a bridge loan to make payroll. My lead investor was furious—not just because I got leverage as they dragged their feet on closing the round, but because they didn’t consider the investor in the same league. Do what’s best for your company. ✅ Term sheets are not infinitely flexible.The best way to negotiate one? Have another. Tip: Keep interested parties separate unless they are building a syndicate. ✅ Don’t raise when desperate.They will see your numbers. A shaky balance sheet weakens your position and removes any leverage. Plan for min 6-12 months in runway. ✅ Fundraising is sales. Treat it that way.Segment investors just like you do customers: hot, warm, cold. Follow up. Personalize. Don’t spray updates and pray. The VC game is nuanced. It’s more art than science—and always about strategic control. Remember: You don’t control the money – until you do.
What is Your Word Worth?
How important is your word? I don’t know if you’ve been following the Trump “Hush Money” trial… Let’s put politics aside – as well as the merits or challenges of the case – for a minute and consider that character is on trial. The only way the State of New York gets a conviction is if the jury believes the prosecution’s key witness: Michael Cohen. This is a case about what your word is worth. This case felt familiar to me but it took a minute to figure out why. It’s because I’ve lived this narrative. In the 1970’s, my mother was a “fixer” for a Baltimore politician named George Santoni. She negotiated deals, covered his tracks and signed questionable contracts. The FBI knocked on our front door investigating a Lincoln Town Car signed for by my mother. It was abandoned by a fleeing felon and found at BWI airport. This was my childhood. And adulthood. My first week in office as county executive, an investigator was in my conference room for an unrelated matter and the first thing he said to me was, “I knew your mother.” My mother lied to the FBI for Santoni. For years. Then, in 1981, Santoni stole from her. She called the FBI and offered to be an informant. They even gave her a code name. Sure they took her calls but she wasn’t a good witness. She never understood that even if she was telling the truth, her credibility was an issue. In Trump’s case, the jury can only convict if they believe the star witness. I’m not saying whether he is lying or not, but he has served jail time for lying to Congress and admitted on the stand that he secretly recorded…and stole from…his client. Your reputation is the most important thing you’ll ever own. I shared this on LinkedIn and wanted to share here too. No political comments please.
Small World Bright Future
One of my first trips beyond my living room since having my hip replaced was to be a guest lecturer at University of Maryland for their brilliant engineering students. This cohort of some of the best and brightest in Maryland accepted the challenge to find innovative solutions to environmental challenges. I shared my entrepreneurial journey and offered mentoring and advice as they prepare for an international business plan competition in Denmark. I’ve only known one Danish entrepreneur, Bo Pedersen – and he’s amazing – so I am excited to make an introduction because his newest company is located at the Danmarks Tekniske Universitet – DTU, where the competition will be held. Plus, how cool is it introduce the Danish professor at University of Maryland to a Danish entrepreneur, in Denmark. The world is small…and the future is bright! Thank you Birthe Kjellerup for having me to your class!
Friendly Faces
In 2000, one of my company investors, Sandy Apgar, invited me to a networking event at the Corcoran Gallery in Washington, DC. It was a who’s who – the place was dark, drinks were flowing, and people were shaking hands.
First Generation
In May 2000, I had the honor of walking across a stage for the first time.
I earned an MBA, without finishing high school or college, from the Loyola University Maryland Sellinger School of Business and Management.
Parking Attendent
Parking attendant.
We spend a lot of time celebrating success. I do it myself. After working my way up from the bottom, a place filled with self-doubt, it feels great to share an accomplishment. But success can be defined in many ways.
Waitress, CEO, and County Executive
I’ve been a waitress, a tech CEO, and a County Executive — but my most important title will always be ‘Mom.’ I know how hard it is to navigate childcare and balance motherhood with a career. It’s why making things easier for working Moms is such a large part of my mission.
