01
Positioning
System
Position your small business to win in the federal marketplace.
Process
Align your capabilities, experience, differentiators, and federal buyer needs into a credible market position.
October Cohort · Starts October 1490 days14 of 20 seats occupied
Turn Years of Bidding Lessons Into 90 Focused Days.
Build your offer, install a repeatable Bid Loop System, and spend the rest of the program bidding live with direct guidance from Derek.
Application deadline
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Days
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Hours
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Minutes
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Seconds
Applications for the October Cohort close October 12 at 11:59 PM ET.
$3,000
Enrollment · card fee applies
10–15
Hours / week
6
Seats available
Founder-led
Derek gets in the trenches with you. You still have to do the work.
Not a beginner-only program
Meet your business where it is. Move it forward fast.
Whether you are developing your first dependable bid process or tightening a system already in motion, the work is customized to your current experience, offer, and pipeline.
The small cohort is the point. With 14 of 20 seats currently occupied, Derek can know the context behind your bids and give feedback that fits the moment.
The program map
Build the system. Then use it live.
The first two weeks establish the operating foundation. The remainder is built around real opportunities and real bidding activity.
About 2 weeks
Build your bidding foundation
- Sample Proposal
- Build a Winning Offer
- Install the Bid Loop System
Remainder of the 90 days
Live bidding with guidance
Put the system to work on your own pipeline, bring questions from active pursuits, and build the judgment to keep moving after the cohort ends.
1Selection2Contact3Quote4Proposal5Pre-Award
The GKM operating blueprint
Ten systems. One connected bidding process.
Each area has a job. Together, they create a repeatable way to decide where to compete, manage a live pursuit, and keep building a healthier pipeline after the program ends.
GKM / 01–04
Foundation
Position your small business for the federal marketplace, focus your agency strategy, and prepare to respond before live bidding begins.
02
Strategy
System
Research federal agencies and make the key decisions that focus your growth.
Process
Identify the agencies, buying patterns, requirements, and relationships that best fit your business strategy.
03
Sample Proposal
System
Practice responding while Derek simulates the contracting officer.
Process
Build a complete sample response, receive buyer-side feedback, and strengthen how you address requirements before a live deadline.
04
Winning Offer
System
Dial in an offer designed to support consistent monthly bid flow.
Process
Connect a recurring federal need to a clear, supportable offer your business can price, pursue, and deliver repeatedly.
GKM / 05–09
Active pursuit
Run each SAM.gov opportunity through the same disciplined Bid Loop so your decisions and submissions improve with repetition.
05
Selection
System
Choose opportunities that match your government contracting strategy.
Process
Evaluate the requirement, agency, fit, timing, competition, and ability to perform before committing resources.
06
Contact
System
Contact contracting officers and potential teaming partners with purpose.
Process
Identify the right people, prepare useful questions, document what you learn, and use each conversation to sharpen the pursuit.
07
Quote
System
Solicit and organize quotes from qualified teaming partners.
Process
Confirm scope, assumptions, availability, and pricing inputs so partner quotes support an accurate response.
08
Proposal
System
Produce compliant, competitive proposals and pricing.
Process
Move from the solicitation and compliance review through writing, evidence, pricing, quality control, and final submission.
09
Pre-Award
System
Build award readiness before the agency makes its decision.
Process
Track the opportunity, prepare for clarifications or negotiations, coordinate partners, and be ready for the next required action.
GKM / 10
Continuity
Keep a deliberate flow of qualified federal opportunities moving toward a bid decision.
10
Pipeline
System
Build a winning pipeline of upcoming SAM.gov solicitations.
Process
Track due dates, agency fit, next actions, teaming needs, and bid decisions so qualified opportunities keep moving into the Bid Loop.
The work compounds through repetitionPosition → pursue → learn → strengthen the next pursuit.
A dependable weekly rhythm
Your recurring schedule
Mon
Tue
Wed
Thu
Fri
Tuesday6 PM ET
Member-led call
Work through the week with the cohort and learn from active bidding across the room.
Thursday6 PM ET
Weekly check-in with Derek
Bring decisions, bottlenecks, and live work that need experienced eyes.
Month end
Schedule your recurring 1-on-1 call with Derek
At month end, book your private one-on-one with Derek, centered on your business and current pipeline.
The curriculum covers October 14, 2026 through February 11, 2027, with December off. All dates are subject to change.
Hear it from Derek
What the Bid Challenge asks of you.
Watch the program overview for the clearest picture of the work, the support, and the standard you will be expected to meet.
6-minute program overview
High access, practical feedback
Support that follows the bid, not a script.
Direct access
Telegram and voice messages when you need direction.
Proposal review
Screen-recorded feedback before your proposal goes out.
Practical support
Email access and help with key communications when appropriate.
In the room
Derek may join a call with a teaming partner when the situation calls for it.
19%
of students actively bidding in the program win within the 90-day window.
Important context
A win can happen inside 90 days. It is not the promise.
The goal is to leave with stronger systems, repeatable processes, better judgment, and a pipeline that keeps creating opportunities after the program ends. Government awards depend on many factors outside any coach’s control, and no award is guaranteed.
Student results
Hear it from contractors who did the work.
Real students sharing what the Bid Challenge changed for their business.
Martha
90-Day Bid Challenge student
Wilziane
90-Day Bid Challenge student
Brian
90-Day Bid Challenge student
Jason
90-Day Bid Challenge student
Nati
90-Day Bid Challenge student
Waleska
90-Day Bid Challenge student
Dana
90-Day Bid Challenge student
Clarence
90-Day Bid Challenge student
Jeremiah
90-Day Bid Challenge student
Derek’s story
In federal contracting since 2013.
Derek James has watched too many talented entrepreneurs struggle because they did not have access to someone who knew the work. That is why he coaches.
He does not currently bid because he does not compete with his students. His focus is putting contractors in position to compete by teaching them to write stronger proposals, identify real opportunities, and build sustainable systems.
The 90-Day Bid Challenge is how he works closely with people who are serious about learning: no fluff or hype, just hands-on guidance grounded in industry experience.
“I’ll get in the trenches with you. But you have to do the work.”
Is this a fit?
Two starting points. One standard for the work.
The Bid Challenge is customized to where your business is today, so the fit test looks different if you are entering the federal market than if you are already operating in it. Be honest with yourself here — the cohort is small and the work is real.
Just entering the federal market
New small businesses
You are building your first real bid process and want to learn it the way the work is actually done.
A strong fit if
- You are highly driven and willing to put in the reps week after week.
- You are open to research and data — you look at what agencies actually post and buy before deciding where to compete.
- You understand you have to be a solutions provider to the government, and you position what you offer around an agency’s problem.
- You are open to working across several focus areas while you learn the market, instead of locking into one narrow niche from day one.
- You can join at the start of the cohort and keep the pace for the full 90 days.
Not a fit if
- You want one narrow niche handed to you and will not look past it.
- You would rather skip the research and go straight to submitting.
- You need an award promised before you will commit the time.
Already operating, ready for the next level
Existing small businesses
You have a business that works. You want the federal pipeline to work just as reliably, in less time.
A strong fit if
- You accept that the federal space is different from the commercial space and are willing to rebuild your assumptions.
- You are open to learning how the government buys and why it differs from the other B2B sales you already do.
- You are willing to write government proposals in the format and to the standard agencies expect.
- You are open to new pricing strategies instead of carrying over commercial pricing.
- You want the years it normally takes compressed into a focused 90 days.
Not a fit if
- You assume commercial sales experience transfers without any adjustment.
- You will not change pricing or proposal approach to fit how agencies evaluate.
- You want the writing, follow-up, and paperwork handled for you.
Not a fit for anyone right now
Derek reviews every application personally. If this is not the right fit, you will hear it directly within 48 hours.
Every coaching hour in the program is with Derek himself; a team member may help with administrative support.
- You cannot protect 10–15 hours each week for the work.
- You need a guaranteed award before you will start.
- You are looking for a passive or hands-off income play.
- You are not prepared to own your own pipeline and your own submissions.
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Days
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Hours
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Minutes
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Seconds
Applications for the October Cohort close October 12 at 11:59 PM ET.
How to join
A clear path from application to enrollment.
01
Apply
Tell us about your business, experience, goals, and readiness for the work.
02
Application review
Derek reviews your application and you receive feedback within 48 hours.
03
Schedule a call
If it looks like a fit, schedule a call to answer any remaining questions.
04
Enroll on the call
If both sides agree it is the right fit, complete your enrollment during the call.
--
Days
--
Hours
--
Minutes
--
Seconds
Applications for the October Cohort close October 12 at 11:59 PM ET.
A straightforward decision
$3,000 for 90 days of focused execution.
You are not buying a promise of an award. You are investing in a smaller learning curve, direct feedback, a disciplined bidding rhythm, and systems designed to keep working after day 90.
Credit-card payments include a $150 processing fee.
Payment plans are available and discussed during the enrollment call.
The fit
- You are serious about government contracting
- You can commit 10–15 hours each week
- You want feedback tied to your actual business
- You are prepared to own the work
14 of 20 seats occupied
6 seats currently available
The cap protects the intimacy and attention the program is built around.
Disclaimer
Derek’s primary product is proposal writing and proposal reviews, offered through his courses and coaching services.
Derek is not a lawyer and does not have a professional designation to interpret the law or federal regulations. He shares his experience working in the industry, and you operate at your own risk. Derek does not propose “set it and forget it” middlemanning. His discussion of regulations is intended to increase awareness and encourage small government contractors to follow them.
If you win a contract as the prime, you must remain involved in and in control of its key and vital tasks. You must stay actively involved when managing teaming partners and should share in as much of the work as possible so you can learn and grow your own business. This is not a hands-off or passive industry. It requires substantial work and can also be rewarding.