In this episode of The Daily Windup, we hear the real journey of going from lean years to landing that first prime government contract—and the challenges that don't go away once you "make it." My guest shares how he earned his 8(a) certification in November 2018, landed his first $4 million sole-source award in March 2019, and finally had the credibility to get lines of credit and scale. But the hard truth is that winning is only half the battle—sustaining and retaining contracts is the real grind.

We dig into the tough lessons every small business owner needs to hear: contracts expire, recompetes are brutal, and focusing too much on chasing new GWACs and IDIQ vehicles like Polaris, Stars III, or OASIS can cause you to lose sight of the work already in hand. He even shares a cautionary story about a mentor who lost a $45 million contract simply because they stopped nurturing the contracting officer relationship. If you think getting your 8(a) is the finish line, this episode proves it's only the beginning.