The Highest Paid Business You Can Start in 2027 (and how much it pays)

Sep 30, 2026

When people hear "government contracting," one of the first things they often assume is that you need years of federal experience before you can compete.

I understand why people think that.

The federal acquisition process has its own language, regulations, systems and procedures. There are contracting officers, solicitations, compliance requirements, proposals, capture strategies, contract administration and an entire lifecycle that can seem overwhelming when you're looking at it from the outside.

But I've also seen people come into this industry without a traditional government contracting background and learn how to navigate it.

Omar is a great example.

Before entering federal contracting, Omar was a retail business owner. He didn't come into the industry with years of experience managing federal contracts.

He started from a completely different background.

Yet within roughly seven months of entering the federal contracting world and working through the GovClose program, Omar had secured 12 federal contracts across a surprisingly diverse range of services.

We're talking about everything from shuttle transportation and restroom rentals to fire extinguisher inspections, crane repairs, dock repairs, dumpster services and facility maintenance.

That's what caught my attention.

Not simply the number of contracts.

It's the process behind them.

Omar didn't stumble into 12 awards.

He learned how to identify opportunities, qualify them, build a pipeline, develop capture plans, understand compliance requirements, work with subcontractors and build relationships around the opportunities he was pursuing.

And that's the part of his story I want other business owners to understand.

Because Omar's experience demonstrates something important:

You don't have to spend 20 years in government contracting before you can start learning how to compete.

But you do need to take the process seriously.


Omar Didn't Start With a Government Contracting Background

Omar came from retail.

That's important because it changes the way I look at his story.

He wasn't starting with an established federal contracting company.

He wasn't already managing a large government workforce.

He didn't have a massive federal past-performance portfolio.

He had to learn the market.

He had to learn the terminology.

He had to understand how federal agencies buy.

And he had to learn how to turn opportunities into actual contracts.

That learning curve is one of the biggest barriers for new contractors.

You can find thousands of videos online explaining individual pieces of government contracting.

But knowing what a solicitation is doesn't mean you know how to build a contracting business.

You need to understand how the pieces fit together.

Omar's experience is a good example of why understanding the full contract lifecycle matters.


Government Contracting Is a Lifecycle, Not a Bid

One of the biggest mistakes I see new contractors make is treating government contracting as nothing more than finding a solicitation and submitting a proposal.

That's only one part of the process.

Before the proposal, you have:

  • Market research
  • Opportunity identification
  • Qualification
  • Capture
  • Customer research
  • Competitive analysis
  • Compliance review
  • Teaming
  • Pricing
  • Proposal strategy

After the award, you still have:

  • Contract administration
  • Scheduling
  • Invoicing
  • Quality control
  • Communication
  • Compliance
  • Performance
  • Subcontractor management
  • Closeout

Omar learned to think about the entire lifecycle rather than focusing only on the moment when a proposal is submitted.

That distinction matters.

Because winning a contract isn't the finish line.

It's the beginning of your obligation to perform.


His First Wins Weren't Million-Dollar Contracts

This is one of my favorite parts of Omar's story.

His early contracts were relatively small.

One shuttle transportation contract was approximately $1,700.

Another opportunity involving restroom trailer rental was around $1,900.

Someone looking at those numbers might say:

"That's not a big government contract."

And they're right.

But that's the wrong way to look at it.

Those contracts gave Omar something much more valuable than the initial dollar amount.

They gave him experience.

They gave him exposure to federal customers.

They gave him past performance.

They gave him a chance to learn how government requirements work.

And they gave him confidence to pursue the next opportunity.

This is something I tell new contractors all the time:

Don't overlook the small contract because you're waiting for the big one.

A $1,700 contract that you perform successfully can be more valuable to a new contractor than a $1.7 million opportunity you're not prepared to execute.

Start where you can perform.

Then build.


From Small Wins to Larger Opportunities

Omar's contracts didn't stay small.

As he gained experience, his opportunities expanded into more specialized and higher-value work.

His portfolio included:

  • Fire extinguisher inspections
  • Crane repair
  • Dock fender repair
  • Dumpster services
  • Power washing
  • UPS maintenance and repair
  • Carpet replacement
  • Mower purchases
  • Facility-related services

One fire extinguisher inspection opportunity involved a five-year Blanket Purchase Agreement with a ceiling of approximately $100,000, with an initial value around $25,000 according to the information provided.

His crane repair work included contracts of approximately $32,000 and $113,000.

A dock fender repair contract was approximately $116,000.

These aren't all the same type of work.

But there is a common thread.

They fit into a broader facilities and base-operations strategy.

That's important.

Omar wasn't randomly jumping from one industry to another.

He was building around a related ecosystem of government needs.


Diversification Doesn't Mean Randomness

This is something I want to clarify.

When I say Omar diversified, I don't mean he decided to become a jack-of-all-trades.

There's a difference between diversification and lack of focus.

His opportunities included different services, but many were connected to facility operations, maintenance and support.

That creates an interesting business model.

A government facility may need:

  • Maintenance
  • Waste services
  • Equipment repair
  • Exterior cleaning
  • Inspections
  • Transportation
  • Specialized repairs

If you're already established in that environment, you can potentially identify adjacent requirements.

That's much more strategic than chasing every solicitation you see.


The Pipeline Is What Made the Growth Possible

One of the most important numbers from Omar's experience is not the 12 contracts.

It's the approximately 60 bids he submitted to reach those 12 wins.

That gives us a rough historical close rate of about 20% based on the numbers provided.

But I want to be careful here.

A 20% historical win rate doesn't mean every contractor should expect to win 20% of their proposals.

Different markets have different levels of competition.

Some opportunities are better qualified than others.

Some proposals are stronger than others.

And Omar's results reflect his particular circumstances and strategy.

The lesson isn't:

"Submit 60 bids and you'll win 12."

The lesson is:

Build enough qualified opportunities that you aren't depending on one proposal.

That's pipeline management.


Stop Bidding on Everything

One of the concepts we emphasize in government contracting is the go/no-go decision.

Just because you can submit a proposal doesn't mean you should.

Before pursuing an opportunity, you need to ask questions such as:

  • Can we actually perform the requirement?
  • Do we understand the scope?
  • Are we compliant?
  • Do we have the required experience?
  • Do we have the personnel?
  • Can we meet the schedule?
  • Is the contract financially viable?
  • Do we understand the customer?
  • Do we have the right partners?
  • Can we compete effectively?

A compliance matrix can be extremely useful here.

It forces you to stop looking at an opportunity emotionally and start looking at it analytically.

If you don't meet a critical requirement, that's information.

Sometimes the smartest decision is no-go.


Capture Planning Changes the Game

Another major lesson from Omar's story is the importance of capture.

Capture means you're not waiting until the solicitation lands to start thinking about the opportunity.

You're studying it beforehand.

You're learning about the customer.

You're researching the requirement.

You're identifying competitors.

You're understanding the acquisition strategy.

You're figuring out your capability gaps.

You're determining whether you need subcontractors.

You're thinking about pricing.

You're building your team.

You're developing a strategy for how you're actually going to win.

That's very different from reactive bidding.

Reactive bidding says:

"Here's a solicitation. Let's write a proposal."

Capture says:

"Here's an upcoming requirement. Let's understand the customer, build the right solution and position ourselves before the proposal is due."

That's a much more mature way to approach federal sales.


Relationships Matter More Than People Think

Government contracting is highly regulated.

There are rules.

There are procedures.

There are FAR clauses.

There are compliance requirements.

But at the end of the day, government contracting is still conducted by people.

People communicate.

People solve problems.

People remember companies that are responsive.

People remember contractors that deliver.

Omar learned this firsthand.

Managing government work isn't always simple.

There can be scheduling problems.

There can be subcontractor disagreements.

There can be pricing issues.

There can be unexpected circumstances.

How you respond matters.

If there's a problem, do you disappear?

Or do you communicate, find a solution and keep the customer informed?

That difference can affect the relationship.


Compliance Is Not Optional

This is one area where I won't compromise.

You can have the best sales strategy in the world.

You can have great relationships.

You can identify incredible opportunities.

But if you don't perform compliantly, you can create serious problems for yourself and your company.

Omar learned to take compliance seriously.

That includes understanding:

  • Contract requirements
  • Proposal requirements
  • Performance obligations
  • Documentation
  • Invoicing
  • Subcontractor responsibilities
  • Scheduling
  • Quality standards
  • Communication requirements

New contractors sometimes view compliance as paperwork.

I see it differently.

Compliance is part of your product.

When the government awards you a contract, it's trusting you to do exactly what you promised to do.


Subcontractors Can Help You Scale

Omar's story also demonstrates the importance of subcontractor relationships.

You don't necessarily need to employ every person who performs every part of your contract.

Depending on the contract requirements and applicable rules, you may be able to use qualified subcontractors to provide specialized capabilities.

But that creates another responsibility:

You have to manage them.

You can't simply find the cheapest company on Google and send them a contract.

Omar looks at factors such as:

  • Past performance
  • Pricing
  • Responsiveness
  • Technical capability
  • Reliability
  • Ability to meet schedules
  • Communication

That's important.

Because when you're the prime contractor, your customer doesn't care that your subcontractor missed a deadline.

You're still responsible for your performance.


Your Subcontractors Become an Extension of Your Company

This is why I encourage contractors to treat subcontractor selection seriously.

A subcontractor may be excellent at the technical work but have no understanding of federal contracting.

They may not understand:

  • Invoicing
  • Documentation
  • Scheduling
  • Government communication
  • Contract requirements
  • Compliance
  • Reporting

That's where the prime contractor has to provide structure.

Omar's company fills some of those gaps.

The subcontractor provides the technical service.

The prime manages the overall contract relationship.

That's a powerful model when it's managed correctly.


Certifications Can Help, But Capability Still Matters

Omar's company also has access to SDVOSB and WOSB certifications through its ownership structure.

Those certifications can open doors to specific set-aside opportunities when the company meets the applicable requirements.

But Omar's approach is interesting.

He hasn't built his entire strategy around chasing set-asides.

Why?

Because certifications don't replace capability.

You can have a certification and still fail to perform.

You can have the right status and still lose opportunities.

The government ultimately needs someone who can deliver the requirement.

So I'd look at certifications as strategic tools, not substitutes for a strong business.


The GovClose Community Helped Shorten the Learning Curve

One thing Omar repeatedly emphasizes is the importance of community.

Government contracting can be a lonely business when you're learning it by yourself.

You can spend hours searching online for answers.

You can watch videos.

You can read regulations.

But eventually, you're going to run into a situation where you need to understand how something works in practice.

That's where experienced people become valuable.

Omar had access to a community of more than 400 students and professionals, including people with backgrounds in government acquisition, proposals, cybersecurity, law and federal contracting.

That kind of environment can accelerate learning.

You can ask questions.

You can compare experiences.

You can get another perspective.

You can learn from someone else's mistake instead of making the same mistake yourself.

That doesn't replace doing the work.

But it can shorten the learning curve.


His Goal Isn't to Stay at 12 Contracts

Omar isn't looking at his 12 contracts and saying, "I'm finished."

He's looking at them as a foundation.

His stated goal is to pursue approximately $3 million to $4 million in contract awards in the next fiscal year, with a longer-term goal of building Providence Federal Group into a $25 million to $35 million business within five years.

Those are goals, not guarantees.

But what matters to me is how he's thinking about growth.

He's not simply saying:

"I want more contracts."

He's thinking about:

  • Capture strategy
  • Recurring opportunities
  • Prime relationships
  • Subcontractor partnerships
  • Federal contract vehicles
  • GSA opportunities
  • State-level work
  • Operational capacity
  • Compliance
  • Pipeline development

That's how you start thinking like a company builder rather than someone simply chasing the next bid.


The Next Level Is Predictability

Winning contracts is exciting.

But eventually, you need something more important:

predictability.

Can you consistently generate qualified opportunities?

Can you forecast revenue?

Can you identify upcoming recompetes?

Can you develop relationships before solicitations are released?

Can you build teams before you need them?

Can you perform multiple contracts simultaneously?

Can your operation handle growth without falling apart?

Those are the questions that determine whether a contracting business can scale.


Omar's Journey Isn't About Getting Lucky

When someone hears that Omar went from retail to 12 federal contracts in roughly seven months, it's easy to focus on the outcome.

But that's not what I want people to focus on.

Look underneath the numbers.

He learned the contracting lifecycle.

He built a pipeline.

He studied opportunities.

He used capture planning.

He evaluated compliance.

He built relationships.

He found subcontractors.

He started with smaller contracts.

He performed.

Then he pursued larger opportunities.

That's a process.

And processes are what businesses can replicate.


The Small Contract Can Be Your First Brick

If you're new to government contracting, don't make the mistake of thinking your first contract needs to change your life financially.

It may not.

Your first contract might be $1,700.

Your next might be $10,000.

Then $25,000.

Then $100,000.

Then perhaps a larger multi-year contract.

There are no guarantees about how quickly that progression happens.

But the concept is important.

You build credibility one successful performance at a time.

Every contract teaches you something.

Every customer gives you experience.

Every proposal gives you information.

Every loss tells you something about where you need to improve.

That's how you build.


If I Were Starting From Omar's Position

If I were coming from a completely different industry and wanted to enter government contracting, I would follow a similar philosophy.

I wouldn't try to become a $30 million contractor overnight.

I'd start with what I already know.

Then I'd identify government demand around that capability.

I'd research agencies.

I'd study existing contracts.

I'd find primes.

I'd learn the procurement process.

I'd build a pipeline.

I'd establish clear go/no-go criteria.

I'd develop capture plans.

I'd find reliable subcontractors where necessary.

I'd perform extremely well.

And then I'd reinvest the experience into the next level of growth.

That's much more sustainable than chasing a giant contract simply because the dollar amount looks impressive.


What Omar's Story Teaches New Contractors

There are several lessons I want people to take away from his experience.

1. You Don't Need to Start With a Federal Background

Omar came from retail.

Your previous career doesn't automatically disqualify you from government contracting.

You may simply need to translate your existing capabilities into a government-market solution.

2. Start Small

A small contract can give you experience, credibility and past performance.

Don't ignore opportunities simply because they're not enormous.

3. Learn the Entire Lifecycle

Don't become obsessed with proposal writing.

Understand opportunity identification, capture, compliance, award and performance.

4. Build a Pipeline

One opportunity isn't a business.

Multiple qualified opportunities create options.

5. Use Go/No-Go Decisions

Don't waste resources chasing contracts you aren't positioned to win or perform.

6. Relationships Matter

Be responsive.

Communicate.

Solve problems.

Build trust.

7. Vet Your Partners

Your subcontractors can affect your reputation and your performance.

Choose them carefully.

8. Compliance Comes First

Don't treat compliance as an administrative afterthought.

9. Use Certifications Strategically

Certifications can create opportunities, but they don't replace capability.

10. Build for the Long Term

The goal isn't simply to win one contract.

The goal is to build a company capable of repeatedly winning and performing government work.


From Retail to Federal Contracting

What I find most compelling about Omar's story is that his starting point wasn't extraordinary.

He wasn't handed a $10 million contract.

He didn't start with decades of federal experience.

He started with a business background, learned a new industry, built a pipeline and began taking action.

His early contracts were small.

Then the opportunities grew.

That's how entrepreneurship often works.

You don't see the final version of the company on day one.

You build it.

Contract by contract.

Relationship by relationship.

Lesson by lesson.


The Government Contracting Opportunity Is Bigger Than One Award

If you're considering entering this industry, I want you to think beyond the next solicitation.

Think about the ecosystem.

There are agencies.

There are prime contractors.

There are subcontractors.

There are consultants.

There are suppliers.

There are specialty service providers.

There are technology companies.

There are professional services firms.

There are construction companies.

There are logistics companies.

There are businesses supporting all of them.

That means there are multiple ways to participate.

You don't have to start at the top of the pyramid.

You need to find where your capabilities create value.


Final Thoughts

Omar's journey from retail business owner to securing 12 federal contracts is a powerful example of what can happen when someone treats government contracting as a business discipline rather than a collection of random bids.

His experience reinforces something I've said many times:

Government contracting isn't about finding a shortcut. It's about learning the system.

Learn how opportunities are identified.

Learn how agencies buy.

Learn how to qualify opportunities.

Learn capture.

Learn compliance.

Learn proposal strategy.

Learn contract administration.

Learn how to manage subcontractors.

Learn how to communicate with customers.

And, most importantly, build a pipeline.

Omar's early $1,700 and $1,900 contracts weren't insignificant just because they were small.

They were the beginning.

They helped create experience.

They created momentum.

They created past performance.

And they gave him a foundation to pursue larger opportunities.

Now he's looking toward $3 million to $4 million in awards in the next fiscal year and has a longer-term goal of building Providence Federal Group into a $25 million to $35 million company over the next five years.

Whether he reaches those exact targets will depend on execution, market conditions, opportunities, competition and many other factors.

But the strategy behind his growth is what matters.

Start where you can perform. Build the pipeline. Learn the process. Build relationships. Protect your reputation. Then scale.

If you're coming from a completely different industry and wondering whether government contracting is possible for you, Omar's story should at least make you ask a different question.

Don't ask:

"Do I have government contracting experience?"

Ask:

"What capabilities do I already have, and how can I turn them into a solution the government needs?"

That is where the journey begins.

And sometimes, the business you build next doesn't have to look anything like the career you had before.


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