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Winner's Win

Winner's Win

De : GC Advising
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The podcast for entrepreneurs breaking into government contracting. Winner's Win delivers real strategies on federal contracts, capture management, and proposal writing — from people who've actually won the bid.GC Advising Direction Economie Management et direction
Épisodes
  • Why Buying a Business Beats Starting One: From Banker to Entrepreneur (with Sterling Birdsong)
    Jul 15 2026

    Is it smarter to buy a business instead of starting one from scratch?

    In this episode of the Winners Win Podcast, Kevin Jennings sits down with Sterling Birdsong, founder of Lendra, to discuss how SBA loans are helping entrepreneurs acquire existing businesses and build wealth through strategic acquisitions.

    Sterling shares his journey from spending 13 years in corporate banking to becoming an entrepreneur, why he left the banking industry, and how his firm helps business owners navigate the SBA lending process.

    In this episode, you'll learn:

    • Why buying an existing business can be less risky than starting one
    • How SBA loans work for business acquisitions
    • Common mistakes entrepreneurs make when seeking financing
    • How lenders evaluate businesses and borrowers
    • The mindset required to become a successful entrepreneur

    Whether you're a first-time business owner, investor, or entrepreneur looking to grow through acquisitions, this conversation is packed with practical insights you can apply today.

    🎙️ Subscribe for more conversations on entrepreneurship, business acquisitions, government contracting, and building long-term wealth.

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    25 min
  • He Lived in His Office With $500K in Debt — Now He Runs 9-Figure Contracts (with Oliver Fernandez)
    Jul 14 2026

    In this episode, Kevin sits down with entrepreneur Oliver Fernandez to talk about the real, unfiltered journey of building a government contracting business — from crushing debt and personal grief to managing nine-figure contracts and a team of 70.Oliver got his start in government contracting around 2008 as a subcontractor, facing half a million dollars in debt. Working on the massive I4 connector project, he had a pivotal realization: despite being part of such a large-scale project, he wasn't the one actually profiting from it. That moment pushed him to pivot from subcontracting to prime contracting — a decision that changed the entire trajectory of his career.With the help of a mentor, Oliver landed his first major projects, but the road wasn't easy — he shares openly about the "dog days" of his early career, including periods where he lived out of his office just to keep moving forward.We also get into:✅ Why he shifted from chasing personal survival to prioritizing his team's success✅ How he sees himself as a "conduit" — someone who exists to pass along resources and opportunity to his team✅ The personal grief and family hardship that became his real turning point✅ His philosophy on "failing forward" and staying hungry regardless of past wins✅ His current goal: building a billion-dollar businessThis is a raw conversation about resilience, leadership, and what it actually takes to scale a government contracting business from nothing.📌 Want to learn more about building in government contracting? Visit gcadvising.com 🔔 🔔 Subscribe for more real conversations with entrepreneurs who've built serious businesses from the ground up.#GovernmentContracting #Entrepreneurship #BusinessPodcast #WinnersWinPodcast

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    24 min
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