Government Contracting at Risk: How AI Could Break the System!

Today I sit down with insurance expert Wes to demystify the policies every government contractor needs but few truly understand. We cover why a General Liability (GL) policy typically includes attorney fees (if you notify the carrier before hiring your own lawyer), why a certificate ≠ the policy, how exclusions (like aviation work) can leave you exposed, and how audits can trigger surprise bills if you don’t price insurance into bids. Real numbers, real stakes: a threatened $700,000 suit that settled for $5,000 (I paid a $2,000 deductible), a $240,000 aircraft damage claim denied under standard GL, audits demanding $15,000 after higher-than-estimated revenue, and cyber “social engineering” fraud that many policies only cover (often up to $250,000) if you phone-verify wire changes. We also hit W-2 vs. 1099 pitfalls, multi-state workers’ comp, and why many policies run 400+ pages—so get a second opinion before you sign or bid. Key Takeaways: Notify your carrier first. GL often supplies the attorney and covers fees; hiring your own lawyer first can void coverage. Match policy to scope. Aviation work needs aviation liability; add states for workers’ comp; price insurance into bids to avoid audit shocks. Harden the basics. Have your agent review contracts + operations + full policies (not the certificate); add cyber/EPLI and follow phone-verification for wires. Learn more: https://govcongiants.org/ Linkedin: https://www.linkedin.com/in/wes-edison/

In this episode of The Daily Windup, we dig into one of the biggest myths floating around right now — that the U.S. economy has somehow become recession-proof. Despite headlines saying everything’s fine, the hard data tells a different story: real GDP has dropped in two of the last three months, growth has fallen from 3.2% to just 1.3%, and both soft and hard data are flashing warning signs. Yet, the market’s still acting like the party never ends. We break down what the Fed’s Beige Book reveals, why the numbers don’t lie, and what every business owner and government contractor should be preparing for right now. Key Takeaways: GDP growth has fallen from 3.2% to 1.3%, showing the economy is slowing — not stabilizing. Soft data is finally morphing into hard data weakness, signaling a potential recession ahead. The Fed’s Beige Book is a must-read for anyone tracking real economic health across sectors. Learn more: https://federalhelpcenter.com/ https://govcongiants.org/ 

In this episode, I talk with Frank Kendall, former Secretary of the Air Force, about how artificial intelligence is reshaping defense and government contracting at lightning speed. Frank explains why AI isn’t just a buzzword—it’s “software that works”—and why the government must learn to be a smart customer, not a slow gatekeeper. We also break down how large language models like ChatGPT are driving a second wave of transformation, creating both massive opportunities and serious risks around bias, human control, and infrastructure strain as electricity demand surges to power this revolution. Key Takeaways: The next wave of AI, powered by large language models, is redefining how defense and government contracting operate. $100s of billions in AI-related contracts are on the horizon, but speed without oversight risks bias and control issues. The Air Force’s 700,000-person, $170B enterprise depends on adapting to AI faster than adversaries like China. Learn more: https://federalhelpcenter.com/ https://govcongiants.org/ 

In this episode, I dive into one of the most perplexing financial phenomena of 2025 — the S&P 500’s explosive rally to new all-time highs. Despite no rate cuts, no fiscal stimulus, and no major breakthroughs, the market has surged more than expected — a “four sigma event” that’s occurred only 0.4% of the time in the past 35 years. We break down how psychology, not fundamentals, is fueling this run — a blend of greed, fear, and herd mentality that could set the stage for a painful day of reckoning when reality hits. Key Takeaways: The S&P 500’s rally is a four standard deviation event — statistically almost impossible. Markets are being driven by emotion, not fundamentals, as fear turns into unchecked greed. Without fiscal stimulus or Fed cuts, this could be a short-lived rally before a major correction. Learn more: https://federalhelpcenter.com/ https://govcongiants.org/ 

In this episode, I sit down with Frank Kendall, former Secretary of the Air Force and Undersecretary of Defense for Acquisition, Technology, and Logistics. Frank shares what’s really happening behind the scenes of the newly announced $175 billion “Golden Dome” program—a reboot of Reagan’s Strategic Defense Initiative that could balloon to $500 billion. We talk about what this means for government contracting, the risks of rushing massive programs, and his firsthand look at managing $170 billion budgets and 700,000 personnel in the Air and Space Force. Key Takeaways: The Golden Dome could open unprecedented government contract opportunities across defense and space sectors. Rushing a $175B program risks massive waste and inefficiency—potentially doubling its cost to $500B. The Air Force’s 2050 vision focuses on AI, autonomy, and long-range power projection to counter China’s military buildup. Learn more: https://federalhelpcenter.com/ https://govcongiants.org/ 

In this episode of The Daily Windup, I expose the hard truth about financing in government contracting—why banks lend only to those who don’t need money and how the wrong SBA loan can trap you for years. We unpack a real story of a contractor who borrowed $800,000 under a 10-year SBA loan only to find it blocked her from getting new funding for awarded contracts. I also share how the SBA’s EIDL loans differ, why subordination matters, and the top five things you need to know about Encore Funding—a company that truly understands the business of federal contractors. Key Takeaways: $800,000 SBA loans can backfire if you grow faster than your repayment schedule. EIDL loans can be subordinated—traditional SBA loans can’t, and that can limit your funding. Encore Funding specializes in helping contractors with flexible working capital when banks won’t.

In this episode of The Daily Windup, we explore how small businesses can leverage over 200 proven GovCon templates and AI-powered tools to win millions in government contracts—while also learning how shifting regulations and compliance costs are reshaping the financing landscape for contractors. I also share a real-world story of one entrepreneur who scaled her business over 15 years, exited successfully, and walked away with a major payday. Whether you’re just starting or ready to scale, this conversation shows how preparation, partnership, and persistence turn contract confusion into generational wealth. Key Takeaways: Access to 200+ GovCon templates and AI tools can accelerate your path to winning contracts. New federal regulations often lead to higher lending costs that contractors must plan for. Building a solid 10-15-year track record can lead to a lucrative exit or business sale. Learn more: https://federalhelpcenter.com/ https://govcongiants.org/ 

In this episode of The Daily Windup, I break down how billions in government contracts go unclaimed every year—and how to make sure your business isn’t part of that statistic. We walk through the pitch deck process, TRL levels, and the exact details you need to win over DoD evaluators. You’ll also learn why following formatting instructions (yes, down to Times New Roman font) could mean the difference between getting funded or being instantly deleted. Federal contracting success isn’t luck—it’s precision, presentation, and professionalism. Key Takeaways: Every year, billions in government contracts are left on the table because small businesses don’t follow simple instructions. Nail your pitch deck by focusing on validation, scalability, and cost savings (save $10M over 5 years, for example). Follow DoD formatting rules to the letter—one wrong file or missing item can get your email deleted instantly. Learn more: https://federalhelpcenter.com/ https://govcongiants.org/ 

In this episode of The Daily Windup, I dive into what separates struggling government contractors from the ones winning consistently—it’s not luck, it’s relationships. We uncover how transparency, community, and the right financial partners can make or break your business. I share why visibility matters (Encore’s team hit 24 conferences nationwide), what questions to ask your lender, and why ignoring these red flags could cost you your next government contract. Ten minutes of pure insight, zero time wasted. Key Takeaways: Don’t trust financial partners who dodge your questions—transparency is everything. The right community and visibility can open more government contract doors than cold calls ever will. Ask smarter: know your lender’s background, cost of funds, and industry presence before signing anything. Learn more: https://federalhelpcenter.com/ https://govcongiants.org/ 

In this Govcon Giants episode, I sat down with Eric Raven, former Under Secretary of the Navy (2022–2024) and longtime defense budget insider, to uncover how a $260B department with nearly 900,000 people actually buys from tens of thousands of small businesses—and where the next wave of Government contracting dollars is headed. From small-business access through Gold Coast (Navy Gold Coast Conference) and buying commands like NAVAIR and NAVSEA, to workforce demands in the submarine industrial base, to the administration’s ambitious “Golden Dome” missile-defense program, this episode is packed with insights you can act on now. Access & Wins: How to engage Navy buying commands (BSOs), why responding to RFIs/Sources Sought matters, and how to leverage events like Gold Coast. Scale & Policy: The shift toward “teeth > tail,” OTAs, and commercial practices that scale pilots from a handful of units to 10,000+. Where the Money’s Going: Submarine base supply chain (17k suppliers, 100k workers needed), the U.S. shipbuilding gap (0.1% vs. China’s ~50%), and the $175B–$500B Golden Dome initiative. Learn more: https://govcongiants.org/ Erik's Linkedin: https://www.linkedin.com/in/erik-raven-7359a6324/