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.
