In this episode of The Daily Windup, I sat down with an entrepreneur who grew up in a family of business owners in India and carried that entrepreneurial spirit across to the U.S. We talked about the mindset and habits he picked up early—like learning how to do more with fewer resources, streamline processes, and build systems that allow a business to thrive. His philosophy? Always look for ways to cut steps, automate, and think creatively so you can scale without burning through cash. That lean mindset is what helped him grow his company and stay competitive in a demanding space.

We also dug into one of the biggest traps new entrepreneurs fall into: quitting their jobs too early. His advice is clear—gain 4–5 years of real-world experience, build savings to create a cushion, and start your business as a side hustle until you’ve secured enough clients to go full-time. By transitioning slowly, your chances of survival skyrocket compared to those who dive in headfirst with no safety net. For anyone considering entrepreneurship, this conversation is packed with hard-earned lessons on preparation, reflection, and long-term success.

In today’s episode of The Daily Windup, I’m talking with an expert who breaks down one of the most overlooked and dangerous parts of government contracting—pricing and accounting systems. Too many small businesses try to limp along with QuickBooks, only to hit a wall the second they go after cost-plus contracts. That’s when the government starts looking at your systems, your policies, your people—and if you’re not ready, you could get crushed by a DCAA audit. We’re seeing these audits more often now, especially with contracts at $50 million and above, and it’s not just about the software. It’s about compliance, procedures, and proving that your numbers tell the right story.

We also dive into the world of “price to win” consulting—a specialized skill that can make or break your bids. It’s not about guessing a number; it’s about knowing the competitive range and understanding what your rivals will do to win. But here’s the kicker: the people who do your pricing shouldn’t be the ones doing your price-to-win. That’s a conflict of interest that could land you in serious trouble. In this episode, you’ll learn why separating those functions matters, which accounting systems are worth upgrading to, and how to avoid being blindsided by the government when you’re chasing bigger contracts.

In this episode of The Daily Windup, I’m breaking down some hard truths about FEMA and government contracting. Too many people wait until a disaster hits to figure out how to work with FEMA—but by then, it’s already too late. FEMA plans in anticipation of disasters, not after the fact. If you’re serious about winning these contracts, you’ve got to be lined up beforehand. I’ll walk you through exactly why proper planning prevents piss-poor performance, and how one overlooked item—a leaf vacuum machine—might just be your ticket to a sole source contract that nobody else is even paying attention to.

But I also need to warn you. While PTACs can be a great resource, they’re not always startup-friendly. If your business is less than two years old, there’s a good chance they’ll turn you away cold. I share my own story of building what I thought was a strong relationship with a PTAC rep, only to be cut off completely when she learned I was a consultant. It’s a reminder that transparency doesn’t always pay in this game, and why you’ve got to navigate the system smartly. Tune in to hear the real roadblocks, the hidden opportunities, and the cautionary tales that can save you time, money, and heartbreak in government contracting.

On today’s episode of Govcon Giants, I sit down with Jason Miller, Executive Editor of Federal News Network, to unpack the chaos shaking the government contracting community. Over the last 4–6 months, we’ve seen partnerships shrink, contracts cut, and entire workforces pushed into early retirement. Jason pulls back the curtain on GSA consolidation, NASA SEWP, consulting contract crackdowns, and the uncertainty surrounding CMMC, NIST 800-171, and small business programs like 8(a). This isn’t just noise—it’s a direct hit on how small businesses survive and thrive in the federal marketplace.

Jason and I go deep on the big numbers—25,000 fewer staff at GSA, programs like CIO-SP3 still stuck in protest, and the seven-year delay of CMMC rollout that’s left contractors dangerously exposed. We also discuss how the Trump administration’s aggressive cost-cutting, paired with industry silence, could cripple government contractors who refuse to speak up. If you’re counting on the old rules to keep you safe, think again—this episode is your wake-up call.

Connect with Jason:

LinkedIn account: https://www.linkedin.com/in/jasonmillerfnn/

LinkedIn corporate: https://www.linkedin.com/company/federal-news-network/posts/?feedView=all

Link to your company: https://federalnewsnetwork.com/

In this episode of The Daily Windup, we hear the real journey of going from lean years to landing that first prime government contract—and the challenges that don’t go away once you “make it.” My guest shares how he earned his 8(a) certification in November 2018, landed his first $4 million sole-source award in March 2019, and finally had the credibility to get lines of credit and scale. But the hard truth is that winning is only half the battle—sustaining and retaining contracts is the real grind.

We dig into the tough lessons every small business owner needs to hear: contracts expire, recompetes are brutal, and focusing too much on chasing new GWACs and IDIQ vehicles like Polaris, Stars III, or OASIS can cause you to lose sight of the work already in hand. He even shares a cautionary story about a mentor who lost a $45 million contract simply because they stopped nurturing the contracting officer relationship. If you think getting your 8(a) is the finish line, this episode proves it’s only the beginning.

In today’s episode of The Daily Windup, we tackle one of the biggest pain points in government contracting—finding the right people for business development (BD) and proposal writing. After attending several conferences last month, I heard the same frustration over and over again: good BD professionals and proposal writers are hard to find. The truth is, you won’t find top talent scrolling through Monster or generic job boards—because the best BD people are already out there winning contracts, not posting résumés.

I share the real “secret sauce” to building your team: networking on LinkedIn, recruiting proven performers from partnerships, and even developing young, hungry talent into superstars. I reveal how I took a writer fresh out of college, invested in Shipley’s training, and within six months they went from $50k to $70k because of the measurable results they delivered. We also dive into strategies to protect your business from “sharks” who steal relationships, and how small businesses can use flexibility to outmaneuver the big primes. This is a must-hear if you’ve ever struggled to recruit or retain the right team to scale your government contracting business.

In this episode of The Daily Windup, I break down one of the most misunderstood parts of government contracting—the acquisition process. Most small businesses don’t realize that the Defense Acquisition University (DAU) is where contracting officers themselves get trained, which makes it the perfect place to pull insights. Understanding this process can completely change how you approach opportunities on SAM.gov or when you get contacted by a contracting officer.

I share a real-world example from one of our students who got confused when a vendor claimed they “already had the contract”—when in reality, the project was still stuck in the pre-solicitation market research phase. This is where RFIs and Sources Sought notices come in, and knowing how to identify this phase can protect you from wasting time and getting misled. If you’ve ever been frustrated with unclear communication or felt lost in the maze of acquisitions, this short episode gives you the clarity to know exactly where you stand—and how to respond with confidence.

On today’s episode of The Daily Windup, I sit down with Marsha, a seasoned professional who’s been in the world of government contracting since 1981. She cut her teeth as a cost engineer on the historic Three Mile Island cleanup contract with Bechtel and later sharpened her expertise at McDonnell Douglas as a pricing specialist. With decades of experience spanning pricing, accounting, and contracts, Marsha reveals why understanding strategic pricing is the foundation of success in government work.

We dive deep into the reality of pricing government contracts—breaking down cost-plus, fixed price, and time & materials—and expose the challenges that companies face when moving from commercial work into federal projects. If you think government money is “easy money,” think again. Marsha explains the hidden complexities, compliance burdens, and regulatory hoops that can make or break your success. This episode is a must-listen for anyone trying to break into government contracting and avoid costly mistakes.

In this episode of the Govcon Giants Podcast, I sit down with Larry Sher, a seasoned government contracts attorney with over 30 years of experience, to break down the massive shake-ups happening in federal and state contracting. We’re talking about billions in grants and contracts terminated overnight, including 2,100 NIH grants and entire programs at agencies like USAID, DOE, EPA, and FEMA. Larry explains why even small businesses can suddenly find themselves buried under compliance obligations, FAR clauses, and False Claims Act liability the moment they sign that government contract. He pulls back the curtain on how bid protests really work, why the “16% success rate” statistic is misleading, and how corrective actions can keep you in the game.

We also dive deep into the Contract Disputes Act, the hidden risks of subcontracting, and how executive orders are creating chaos and uncertainty for contractors. Larry warns about the dangers of signing a contract without understanding the downstream compliance requirements—and how one misstep could cost you millions. Whether you’re chasing a state contract for bulletproof vests worth millions, managing a prime contract with subs, or fighting an unlawful grant termination, this episode will open your eyes to the real risks of doing business with the government. And Larry’s #1 piece of advice? Come to him before you sign, not after you’re already in trouble.

Larry's Linkedin: https://www.linkedin.com/in/larry-sher/ 

Company Website: https://www.winston.com/ 

In this episode of The Daily Windup, we hear the remarkable story of how a veteran-owned fuel delivery company went from serving local residential customers to expanding across multiple states—thanks to a single prime government contract. The conversation dives into the high-stakes world of priority one facilities during natural disasters, where fuel deliveries to hospitals and emergency shelters keep critical life-support equipment running. We explore the behind-the-scenes challenges of winning a prime contract as a new vendor, adapting quickly to unfamiliar work like tractor-trailer bulk deliveries, and using government performance as a springboard to secure private-sector clients.

You will also learn how certifications and incentive programs open doors for small, veteran-, woman-, and minority-owned businesses to enter competitive commercial markets. From landing the Wynn Casino project through a single introduction to building long-term relationships with major construction firms, this episode showcases how one contract can transform a company’s trajectory. With lessons on readiness, seizing opportunities, and scaling fast without sacrificing service, it’s a must-listen for anyone looking to break into larger contracts and grow beyond their local footprint.