Kevin Jennings

Making money in government contracting is achievable for almost anyone.

Keeping it? That's where most people fall apart.

I sat down with Geoff Cole — a GovCon veteran since 2015 — and we got into the real side of this business. Contracts lost during low performance. Lawsuits. Managing restaurants alongside government work. Legal representation across multiple states.

We also talked about the 8(a) program, bonding capacity, lines of credit, and why the "easiest" contracts often come with the thinnest margins.

And his next move? Building an Expedia for government contracts.

This one is raw and real. Full episode coming soon.

🔔 Subscribe so you don't miss the full episode drop.

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1 month ago | [YT] | 6

Kevin Jennings

New episode dropping next week. 🎙️

And this guest? A different kind of winner.

Meet Busta Free.

You may know him from the music. But this conversation goes way deeper than that.

His journey to success isn't a straight line — and that's exactly what makes it worth watching.

We're giving love to someone who built something real in an industry that chews most people up and spits them out.

Same Winners Win energy. Different lane.

🔔 Subscribe so you don't miss it when it drops on YouTube next week.

#WinnersWinPodcast #BustaFree #WealthBuilding #EntrepreneurMotivation

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1 month ago | [YT] | 3

Kevin Jennings

Federal or state contracts — how different are they, really? 🤔

Turns out, they play by two very different sets of rules. Here's the breakdown:

📍 Where to look — SAM.gov covers every federal opportunity nationwide. States each run their own procurement portal, so you register separately per state.

📍 Competition — Federal contracts draw bidders from across the country. State/local opportunities often see far fewer bidders per posting.

📍 Size & speed — Federal contracts tend to be larger but move slower (6-12+ months). State/local contracts are usually smaller but can award in weeks.

📍 Certifications — Federal has 8(a), HUBZone, WOSB, VOSB, SDVOSB. States often run their own MBE/WBE/DBE programs on top of that.

Same goal — very different playing fields.

Want to know which path fits your business? Join our 90-Day Group Coaching Program!🧀

#GovernmentContracting #FederalContracting #StateContract #GovConTips

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1 month ago | [YT] | 2

Kevin Jennings

🎙️ Winner's Win is now streaming!

You can now listen to the Winner's Win Podcast on Spotify and Amazon Music—making it even easier to learn from entrepreneurs, government contracting experts, and industry leaders wherever you are.

Whether you're building your first business, scaling with government contracts, or looking for real-world strategies from people who've done it, we've got you covered.

🎧 Now available on:
🟢 Spotify
🔵 Amazon Music

Hit Follow so you never miss a new episode.

Listen. Learn. Win. 🏆

#GovernmentContracting #SpotifyPodcasts #AmazonMusic #GovernmentCheese #GCAdvising

2 months ago | [YT] | 1

Kevin Jennings

Did you know your NAICS code could impact the government contracts you're eligible to pursue?

Many new contractors think choosing a NAICS code is just another registration step—but it's one of the most important decisions you'll make.

Choosing the right code can help you stay eligible for more federal contracting opportunities as your business grows.

Before you register, make sure you're choosing strategically—not just picking the first code that sounds right.

👉 Swipe through to learn why your NAICS code matters and how to avoid a costly mistake.

Need help getting started in government contracting? Join our 90-Day Group Mentorship NOW!

#GovernmentContracting #NAICSCodes #FederalContracts #SBAGov

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2 months ago | [YT] | 2

Kevin Jennings

The fourth quarter is one of the biggest opportunities of the year for government contractors. 🎯

Agencies are racing to obligate remaining funds before the fiscal year ends — and the businesses that are prepared right now are the ones who capitalize.

Success in Q4 isn't luck. It's preparation and execution.

Swipe through for the 5 steps 👉

Want the exact system we use to help businesses compete for (and win) government contracts?

Join our 90-Day Group Mentorship. 🧀
#governmentcontracting #howto #guided #mentorship

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2 months ago | [YT] | 1

Kevin Jennings

Shaq made millions playing basketball.
He made billions after basketball.

Not because he worked harder — because he understood the difference between income and wealth.

Skills pay the bills. Ownership builds the legacy.

That's exactly what government contracting is. Not a gig. Not a side hustle. A business that can keep winning contracts for years — with or without you in the room.

The goal was never to trade more hours for more money. The goal is to build something the government keeps coming back to.

That's why we don't just teach you how to submit a bid. We teach you strategy, systems, and execution — because that's what builds something that lasts.

👇 Join our 90-Day Group Mentorship!

#GovernmentContracting #Entrepreneur #Shaq #SuccessMindset

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2 months ago | [YT] | 2

Kevin Jennings

Today is the day. 🎙️

The 90-Day Group Mentorship officially starts today — and if you've been on the fence, this is your last chance to jump in with 20% off.

12 live sessions. A full GovCon roadmap. Bid labs. Pricing playbooks. Weekly accountability. A private community of operators all moving toward the same goal.

Everything you need to go from zero to contract-ready — starting right now.
The cohort is live. The discount is still active. The only thing missing is you.

#GovernmentContracting #90DayMentorship #FederalContracts #Mentorship #StartToday

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2 months ago | [YT] | 0

Kevin Jennings

Cabo Verde wasn't supposed to make history.

Their 40-year-old goalkeeper, Vozinha, stood against one of the greatest teams in the world and helped take Argentina to extra time.

Sometimes the biggest obstacle isn't your age—it's believing you've missed your chance.

Government contracting doesn't reward the youngest entrepreneur. It rewards businesses that can deliver value.

Your timeline doesn't have to look like everyone else's. IT JUST HAS TO START.

#GovernmentContracting #FIFA #CaboVerde #Vozinha #Goalkeeper #NeverTooLate #Mentorship

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2 months ago | [YT] | 1