I wouldn’t call it success yet, but I will say we are making real progress.
I recently submitted my second offer through eOffer to obtain a Multiple Award Schedule (MAS) - basically a long-term contract that would allow Yorktown Tools to sell on GSA Advantage, the government’s version of Amazon. This has been one of my top priorities since the day the company was officially formed.
The First Attempt
My first submission was a monster - a 156-page solicitation. Don’t let that number scare you; most of it was filler with rules and regulatory guidance. Still, it took several full days of hard work to complete. A couple months later, it came back rejected with a massive amount of red ink.
Even though I didn’t expect to get it right the first time, the rejection hit hard. After putting in that much time and effort, seeing all the red marks was eye-opening and honestly defeating. It wasn’t that I wasn’t qualified - a lot of it came down to my ignorance of the process and jargon. This is exactly why so few small businesses actually win these contracts. The process is not easy, and if it were, everyone would do it.
Understanding the System
For those who don’t know, eOffer is the portal for applying for long-term federal supply contracts. Like most government websites, it’s awful - not user-friendly, difficult to navigate, and full of red tape. Before you can even begin, you have to register in SAM.gov to get a UEI and CAGE code, which is another slow and painful process.
A full GSA eOffer application is closer to a full-blown procurement proposal than a simple online form. It involves 40–100+ inputs, detailed pricing justifications, technical narratives, and supporting documents. It’s a lot.
Round Two – The Mental Grind
After licking my wounds from the first rejection, I waited. For the first week or so, I couldn’t bring myself to jump back in, I didn’t want anything to do with it. I needed a break. So, I shifted focus to other parts of the business because the thought of doing it all over again felt overwhelming. There were definitely moments of doubt and frustration even though I expected the results. I caught myself trying to justify why I should pursue other paths instead.
It took me five months to build the discipline to submit the second package. This one came in at 194 pages. I narrowed my offered products from 500 items down to just 20. My logic was simple: get my foot in the door first, then scale once I have a winning template.
The truth is, this process is a mental fuck. Investing weeks (sometimes months) of evenings, early mornings, and weekends into something only to get a big red-ink rejection is tough. You have to consciously push through demotivation. I’m glad I found the resilience to keep going, even if it wasn’t fast. Having the flexibility the Army is still giving me during my transition has been a huge help — both mentally and financially.
Lessons Learned
This experience has taught me a lot:
• Chip away at it little by little. The system, documentation, and bureaucracy are insane. Taking it in small chunks is the only realistic way forward.
• Start narrow. Offering hundreds of items on your first try is overwhelming. You can spend countless hours for nothing.
• The jargon and process are half the battle. Even if you’re qualified, the bureaucratic language can sink you.
Final Thought
Government contracting is not for the faint of heart. It’s slow, painful, and mentally draining. But the potential reward is massive. The U.S. federal government spends hundreds of billions of dollars every year, and having an awarded schedule would be a huge competitive advantage for Yorktown Tools.
I expect my second attempt probably won’t succeed either, but I’ll happily take it if it does! However, if the third attempt also doesn’t work out, I’ll likely hire a company that specializes in these submissions. By then, my own efforts should have already made a significant dent, so bringing in professionals will hopefully carry me across the finish line with minimal extra effort.
Just know I’m still very much in the fight. I’ll keep you updated as soon as we break through. Progress isn’t always linear or pretty—but it’s still progress.
These are Tools Worth Fighting For.