Watch Keeper Holdings

Blog

  • Death of a Software Engineer

    As a long-time developer, the productivity jump is undeniable—MVPs that used to take weeks now take hours.

    But something feels off. The role of the traditional software developer is clearly shifting, and not everyone wants to admit it yet.

    I won’t pretend to have the answers. I do have reading material that’s actually thoughtful:

    
    Critical thinking didn’t go away. It just got more expensive.

  • Is losing $500,000 something you’re willing to risk? 

    Of course not.

    But that’s exactly what Rick did.

    Rick ran a roofing business doing $2M in revenue and $450K profit. After 15 years, he was ready to sell.

    He got a $1.5M offer.

    He turned it down.

    Why? Because someone once told him a business is worth 1× revenue. No valuation. No expert advice. Just a gut feeling.

    The buyer moved on.

    A year later, Rick was burned out. Sales dropped to $1.7M.
    The next offer? Still $1.5M—but now with an earnout to hedge the decline.

    By chasing a made-up number, Rick lost time, leverage, and potentially $500K+.

    Bottom Line: What you think your business is worth doesn’t matter. What the market says does.

    If selling is even remotely on your radar—now or within a couple years—let’s talk.

    I might be interested in buying directly. And if it’s not the right fit, I can introduce you to a broker or two.

    No pressure. Just a quick call to help you make smart moves. Book some time, it could save you $500k

  • Gov Con deals

    💼 Consulting & Technology Services

    A certified consulting and technology firm delivering business, engineering, IT, and management solutions across public and private sectors, offering diversification, defensible positioning, and steady growth potential.

    🗃️ Project Red Stapler

    A long-standing service-disabled business specializing in office and facility planning, furniture procurement, project management, and relocation logistics for government clients. It has a stable contract track record, seasoned management, and clear operational efficiencies to improve margins and expand services. 

    📡Project Raider

    A provider of essential IT and communications services for government and first responders, benefiting from sustained demand, deep technical capability, and strong expansion potential with the right investment.

    ☢️ Project HazMat

    An established hazardous waste treatment and management operation with multi-state reach and long-term contracts, delivering stable cash flow and regulated-market expansion opportunities.

    ⚓ Defense Technology Anchor

    A technology and training solutions business with 20+ years supporting defense missions, ~20% margins, priced near a 4x multiple, and not dependent on contract set-asides—built for stability.

    🎖️SDVOSB Logistics & Training Platform

    A Service-Disabled Veteran-Owned Small Business specializing in logistics, training, and management services, providing durable access to protected GovCon niches and strategic set-aside advantages.

    🔒Long-Term Federal Technology Services

    A federal technology services firm currently in year one of a 10-year performance contract, offering long-dated revenue visibility, downside protection, and a strong base for disciplined growth.

    💻 Gov Con information technology (IT), staff augmentation, and research & development for high profile Gov Agencies.

    The Company provides information technology (IT), staff augmentation, and research & development (R&D) services. The Company specializes in IT modernization, and orchestrates a flexible workforce ecosystem to build cloud and artificial intelligence (AI) solutions that enhance business outcomes for the aerospace and public sectors. Profitable EBITA

    Email me for more details on any of these deals.

  • Licence to Scam for the US Gov!


    Email from Watch Keeper Holdings, LLC

     

    THE WATCH PERSISTS…

    Signed On the Dotted Line… an adventure into #govcon

    “The Trump administration is preparing to enlist private companies in more aggressive efforts to go after criminal and state-sponsored hackers, according to people familiar with the matter.” Bloomberg Article & archived article

    Finally, a bit of validation.

    For years, I’ve had what you might call a profitable mind. Ethics are what kept it in check. So when I read that the Trump administration may enlist private companies to more aggressively pursue criminal and state-sponsored hackers, my reaction was simple: Sign me up, I have portfolio I scams! 
    

    Scams cost Americans billions each year. Southeast Asian syndicates run nonstop operations using forced labor. Crypto has made it easy to wash the money so fast, the gov can’t even keep up.

    I know because I’ve spent years building automation and identifying profitable loopholes in complex systems—legally. The proof is in the chart. I even made an accounting system for the revenue. Sorry I can’t fully explain it because you all might want in on the deal… 

    Now it’s time to scale. This is a chance to turn cyber defense into offense, profit while disrupting billion-dollar scams, and actually change the economics of fraud. The market is massive, Uncle Sam is saying go for it, are you ready to partner?

    📓Field Notes📓

    🤔 OPM and OBM are getting married. Probably divorce in a few years… I don’t see any synergies? 🤷‍♂️

    🥊 Two Proposal AI Heavyweights Step Into the Ring. 🏆 I won — because while everyone else was pitching AI to write proposals… I just submitted a proposal to every contracting officer offering to help them analyze all the AI-written proposals instead.

    🤝 I’m not really start up guy anymore, but a Military Vet Start Up might interesting.

    🤝 Prime Contractor, Subcontractor, Mentor-Protégé or Joint Venture? Got an idea or want to talk? I’m around…

    Constant Contact

  • The Microsoft Way…


    Email from Watch Keeper Holdings, LLC

     

    THE WATCH PERSISTS…

    Signed On the Dotted Line… an adventure into #govcon

    My friend Bill Gates always used to tell me, If direct entry is difficult, strategic acquisition is the solution.

    📓 Deals 📓
    • The DoD Anchor (Stability & Established Performance): This technology solutions business is the most established, with over 20 years of history providing mission-critical technology and training solutions primarily to the DoD. It offers a solid 20% margin and is available at approximately a 4x multiple with no reliance on contract set-asides.
    • The SDVOSB Advantage (Strategic Niche): This is a Service-Disabled Veteran-Owned Small Business (SDVOSB) specializing in logistics, training, and management services. Its valuation is tempered by the SDVOSB set-aside status, but it provides access to a specific government contracting niche.
    • Project Sword (Future Revenue Security): A technology services company, founded in 2013, providing federal agency support. This deal is attractive because its revenue stream is secured by being in the crucial first year of a 10-year performance contract.

    Additionally, I am tracking several Early-Stage Leads that require some preparatory work before they can be seriously pursued, shoot me a Signal if you are interested.

    📓Field Notes📓

    🤔 CMMC enforcement begins with mixed industry readiness, are you ready? Don’t worry you can send war plans on signal! 🤷‍♂️

    🚁 Drone Gauntlet challenge? Maybe it would be better if it was a reality Competition show?🎖️

    🤝 Prime Contractor, Subcontractor, Mentor-Protégé or Joint Venture?

    Watch Keeper Holdings is at the ready.
    Constant Contact

  • Before You Even Open This Email, I’ve Already Reviewed Dozens of Opportunities—Faster Than You Can Say ‘SAM.gov.’


    Email from Watch Keeper Holdings, LLC

     

    THE WATCH PERSISTS…

    Signed On the Dotted Line… an adventure into #govcon

    Before
     

    After

    Before I even let the dogs out in the morning, I can tear through new solicitations, score them against my capabilities, map out the risks, and—if it’s worth the calories—spin up a proposal. 
    
    The above opportunity? 1 out of 7 on my internal fit score. Instead of wasting half a day downloading twenty attachments just to realize the agency wanted a unicorn.

    I may not be in the “AI pickaxe” business like everyone else right now, but I am building tools that directly support my mission—so I rolled my own code.
    

    And here’s the real kicker: if I can build this internally, imagine what I could build for your organization.
    

    Oh—and yes, there’s a video.

    📓Field Notes📓

    🤔 Should Your Tech Company Enter the Defense Market? Five Considerations to Weigh. (probably not, I don’t want any more competition.) 🤷‍♂️

    ⛓️ AI + Military supply chain: Good Luck to Exiger and Palantir. As someone who worked in S-4 previously… your going to need it! 🔗

    🎸 Giving Tuesday… is that still a thing? Here is my new favorite charity. 🎖️

    🤝 Prime Contractor, Subcontractor, Mentor-Protégé or Joint Venture?

    Watch Keeper Holdings is at the ready.
    Constant Contact

  • If the beach can’t have your full attention, this email definitely shouldn’t…

    THE WATCH PERSISTS…

    Signed on the dotted line… an adventure into #govcon

    🌴 While I’ve been deep in my AI proposal code lately, I nearly forgot to write this update. Then again, most folks are probably reading this from the 🏖️! Here are some engaging headlines to take you into the break. I’ll be back after the holiday with an automated government proposal robot.

    🧑‍⚖️ 8(a) you have been summoned to the supreme court.

    💰 SAIC Secures $42 Million for set asides! (SAIC has been awarded a significant $1.4 billion COBRA task order)

    🤖 I Reverse-Engineered 200 AI Startups. 146 Are Selling You Repackaged ChatGPT and Claude with New UI.

    🚨 Fraud in the HUBZone, shocking?!

    🚗 For those on long drives… now is not a good time to start private equity fund. There is could definitely be a private equity for #govcon, oh wait it’s call Lockheed…

    🤝 As always… I endorsed this message… Prime Contractor, Subcontractor, Mentor-Protégé or Joint Venture? Watch Keeper is at the ready.

  • I Trained AI to Read GovCon RFPsSo You Don’t Have To.

     

     

    I Trained AI to Read GovCon RFPs
    So You Don’t Have To.

    A lot of companies swear they can “write your GovCon proposals.”
    Cute. But I actually know AI and GovCon—dangerous combo.

    Here’s how it works:

    1. Scans for opportunities by NAICS code,
      finds solicitation for the
      IRS.
    2. Auto-downloads every doc (yes, even the 14 attachments nobody reads)

    3. Analyzes everything to decide if it’s a fit — using my experience, not just robot vibes

    4. Writes the proposal
    5. Boom. Done.

    👉 If you want proposals that don’t read like a dryer manual, Let’s talk. 👈

     
    AI Coding Assistant

    📓Field Notes📓

    🧠
    The Most Valuable Military Contractor Works in 0s and 1s

    🔥 Great First-Round Interview With FireStorm. Does anyone have connections over there?
    On the flipside, the DoD & DOW are getting serious about drone countermeasures.

    💸 Anybody Got Six Million and want to be in the movies?


    An SDVOSB Media / video production business is up for sale.

    📈 Proper Planning Prevents Poor Performance


    Politics aside, spending will increase over the next three years. Are you ready?

    🤝 Prime Contractor, Subcontractor, Mentor-Protégé or Joint Venture?


    Watch Keeper Holdings is at the ready.

    Gunner Chad, USMC (ret)


    LinkedIn

  • 💡 The Secret to Saving Prime Contractors Money: Stop Paying Six-Figure Staffing Fees

    It happens every month: a recruiter calls, trying to place elite talent on your major prime contract.

    Lockheed Martin

    You pay huge fees for this service—often a six-figure commission that channels a significant chunk of your budget to a staffing agency.

    There’s a simpler, less expensive way to get the same expertise.

    ✂️ Cut Out the Middleman

    Recruiters are finding the most qualified candidates, then sending them your way. Why not skip the high fees and partner directly with the solution?

    Watch Keeper is a registered Veteran-Owned Small Business (VOSB). We handle the business, we have the clearance, and we deliver results.

    🚀 Hire the Solution Directly

    When you partner with a VOSB like Watch Keeper, you get a direct partner invested in your success.

    • You get the same elite expertise.
    • You eliminate the high agency fees.
    • You satisfy your VOSB utilization goals.

    Stop writing unnecessary checks to recruiters. Hire the solution directly.

    Let’s discuss how Watch Keeper can deliver the support your contract needs while significantly lowering your overhead.

  • 💰 Off-Market GovCon Plays – Private Credit & Equity Wanted!

    Somewhere ‘along the way’, I started my search fund investigation, then turned to a self-funded search. Now, I’ve sourced multiple deals, so I’m not entirely sure whether I’ve created a self-funded search fund, an intermediary service, or a holding company. But looking to start the conversation.

    None of these projects are under LOI yet, but they are very warm—or, as we say in artillery, target in the open. These are essentially off-market deals, all targeting the GovCon space: All 3 companies can be run REMOTE, they are not location dependent.

    As the government pushes RTO: Project Red Stapler

    As the Military/1st Responder / Police State sector ramps up: Project Raider

    Regardless of politics, proper disposal will always be necessary: Project HazMat

    Each deal involves a SDVOSB government set-aside. With the right SDVOSB owner-operator (1st option would be me), creative deal structuring ensures these set-asides remain intact. These aren’t “turn and burn” opportunities—they align with GARP principles and have a long track record of success with solid, proven returns. (All three have at least 15 years)

    P.S. This post contains a song title and a famous movie reference—let’s see who catches them.

    P.S.S. Veteran set asides are not related to D.E.I.