Most Contractors Quit Too Soon — The 18-Month Government Contracting Trap

In this episode of The Daily Windup, I unpack one of the most overlooked truths about winning government contracts: you’re not getting picked because they don’t know you exist. That’s where our three-pronged strategy comes in. Step one is just raising your hand and saying, “Hey, I’m here!” It might sound simple, but the truth is—if you’re not showing up, following up, and building relationships with sub-agencies in your niche, you’re invisible. And let’s be clear: the government doesn’t get the best people—they get the best people who show up.

I also break down the long game mindset you must adopt. We’re talking 3 to 18 months of relationship-building before a single dollar hits your account. Why? Because this isn’t just business—it’s national security. Think about it: would you want a stranger walking into a military base and plugging a USB into a government computer on day one? Neither would they. You’ve got to earn trust, pass the “persistence test,” and keep showing up. So if you’re in this for fast cash, this episode is your wake-up call. But if you’re ready to build a real foundation and win for the long haul, then it’s time to get strategic. Let’s get it.