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Winner's Win Podcast

Welcome to the Winners Win Podcast, where we dive deep into the stories, mindsets, and strategies of top-level entrepreneurs who've turned their visions into reality. Every episode, we uncover the real journey behind their success—the obstacles they've faced, the lessons they've learned, and the pivotal moments that shaped them into the influential leaders the world admires today. Tune in to gain powerful insights, actionable advice, and the inspiration you need to elevate your own path to success.

GovCon Strategies & Insights

GovCon Strategies & Insights is your go-to resource for mastering the government contracting landscape. We deliver powerful strategies, expert analysis, and actionable advice to help you navigate the complexities of winning and executing lucrative government contracts. Whether you're brand new or looking to scale, you'll gain insider knowledge, proven frameworks, and real-world insights from industry veterans. Leverage our expertise to sharpen your bidding approach, build robust operational systems, and confidently grow your GovCon business.

Past Events & Workshops

Our past events have empowered hundreds of entrepreneurs to master the art and science of government contracting. Attendees have learned directly from industry experts how to secure lucrative contracts, navigate complex federal processes, and scale their businesses successfully. The success stories speak volumes—multi-million-dollar contracts secured, thriving businesses launched, and countless transformations in strategy and mindset.

Now, it's your turn. Don't miss out—secure your spot at our upcoming event and take the next big step toward mastering government contracting. Spots are limited, so act fast and join us today!

TESTIMONIALS

Driving Growth, Amplifying Impact

Ivan Knight

Founder of Cilegna LLC

For the last year or so I had been researching and seeking a mentor for government. When I came across Kevin Jennings and his program The Government Cheese it was an easy decision.

Kevin, his team and their resources are unmatched. The level of accuracy and information we receive is phenomenal. I know this will be a lifestyle for me especially with what I know now.

My family and I are grateful for this opportunity to come across people who truly care, know the business and are willing to share the information.

The group community is awesome along some of his team members like Jacqueline and Kenny.

Thank you all for your support, leadership and teachings. I'm with this government cheese family for life.

Darnell

Kevin first met Darnell at InvestFest in 2022, where he initially expressed interest in joining our program. He officially enrolled in March 2023, took the initiative by working through the course independently, and then attended our Houston boot camp in October 2023—which marked a turning point.

Just a few weeks after the boot camp, Darnell secured his first government contract: two Blanket Purchase Agreements (BPAs) with the Army Corps of Engineers, supplying roadway materials like asphalt and lime rock for their projects.

Since then, he’s won two additional contracts, rapidly transforming his business from having no government contracting experience to managing multi-million-dollar logistics and trucking contracts.

Darnell’s success was driven by strategic positioning. Although already established in trucking, he discovered limited direct trucking contracts. Instead, we targeted construction contracts with significant trucking requirements. This approach allowed him to leverage his existing strengths in logistics.

Ophelia Johnson

Entrepreneur

I'm here down in Tampa from Pennsylvania, and this boot camp was everything and more. I went to the Miami intro boot camp, and so I knew some of what to expect. But this advanced boot camp really helped take my business strategy to the next level. I feel far more equipped to build and scale my business. I got some new strategies I'm going to implement right after this. Extremely appreciated.

Tony Stephenson, MBA

CEO of Stephenson Industries

I joined the Government Cheese program to better understand how to grow and sell a business. Being a service-disabled veteran, I'm aware there are specific contracts set aside for individuals like me to grow a company and get long term work. In just two months, Kevin's guidance has surpassed my expectations. His straightforward teaching style, combined with his openness in sharing his professional network with his students adds a ton of value.

John

John joined our business advisory program in August 2024, eager to dive into the world of government contracting. Within his first two months—September and October—he successfully secured four contracts, netting an impressive $50,000 in profit during his first 90 days.

Building on this initial success, John is now actively pursuing the acquisition of an established business within the government contracting space, positioning himself for even greater growth and profitability.

Michael

Michael first connected with us at GovCon, Systems & You in 2023. At the time, he was working as a project manager for a construction company but had aspirations to venture out independently. We began guiding him through the initial stages of setting up his own company, laying the groundwork for his future in government contracting.

In early 2024, Michael fully embraced the GovCon, Systems & You program. We worked closely with him to establish robust operational systems and streamline his business processes from the ground up.

Equipped with these foundational systems, Michael successfully secured multiple government contracts shortly after launching his company. Remarkably, he’s on track to generate seven figures in revenue within his very first full year of government contracting—a testament to the power of combining the right guidance, effective systems, and strategic execution.

Q

Q attended our Atlanta event in June 2024 shortly after acquiring a landscaping business, seeking effective strategies to scale through government contracts.

Immediately following the event, Q successfully secured a multi-year landscaping contract with the U.S. Postal Service in July. Building on that momentum, he quickly went on to win additional contracts.

Incredibly, Q is projected to achieve high six-figure revenue in his first year alone, with seven-figure earnings anticipated in his second year of government contracting. Q’s rapid growth and impressive success underscore the impact of leveraging targeted government contracting strategies from the outset.

GC Advising: Proven Results.

For Service-Based Businesses Like Yours.

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