Shark Tank to Sam.gov: The Real Money is in Government Contracting
Former Air Force Colonel Greg Coleman closed the largest tech deal in Shark Tank history with Mark Cuban. But that’s not where he found the real opportunity.
After flying three U.S. presidents, building a venture-backed startup, and negotiating deals on national television, Greg knows something most entrepreneurs miss: the federal government can be a reliable path to scaling breakthrough technology…
If you understand the process.
Now, as a certified GovClose professional helping deep tech companies navigate Defense Innovation Unit (DIU), SBIR programs, and other transaction authorities, Greg is doing what he wished someone had done for his company years ago.
From the Cockpit to Shark Tank
Greg’s journey reads like a Silicon Valley origin story—except it starts at 30,000 feet. Nine years active duty flying KC-10 refuelers and Gulfstream Vs for combatant commanders. Then another 16 years in the DC National Guard flying VIP airlift missions for congressional delegations, cabinet members, and first ladies across three presidential administrations.
But the military was just chapter one.
While serving in the Guard, Greg earned his Wharton MBA and co-founded Sworkit, a fitness and wellness tech company that would eventually land him on Shark Tank. The pitch was flawless. The negotiation was even better. At the time, it was the largest tech deal in the show’s history with Mark Cuban.
“I didn’t want to do it at first,” Greg admits. “But we prepared so thoroughly that we negotiated the deal we wanted. Though we ultimately didn’t close with Mark, Shark Tank became ‘the gift that keeps on giving’—every rerun drove a spike in new customers.”
The Valley of Death Problem
While building Sworkit taught Greg how to raise capital, manage boards, and make payroll, it also exposed him to a problem he’d later spend years solving for others: how do innovative tech companies survive long enough to reach production scale?
The answer came from an unexpected source—the Department of Defense.
In 2018, Greg joined MD5 (which later became the National Security Innovation Network under DIU) to create their acceleration portfolio. His mission: help early-stage companies figure out how to work with DoD. He managed multiple cycles of SBIR programs, designed pathways from prototype to production, and watched firsthand which companies successfully navigated the “valley of death” and which ones didn’t.
The difference wasn’t always the technology. It was understanding the system.
Why Other Transaction Authority Matters
Greg breaks down what most entrepreneurs get wrong about federal contracting: “The department still looks like either the Evil Empire from Star Wars, the Borg from Star Trek, or some black box algorithm they need to crack. What they don’t understand is that this is a relationship-driven business.”
He’s particularly bullish on Other Transaction Authorities (OTAs), especially through organizations like DIU. Unlike traditional FAR-based contracts, OTAs offer:
Speed: White papers instead of 100-page proposals. Three-page submissions that lead to demos and contracts.
Flexibility: No burdensome accounting systems required. Company-friendly IP protections.
Direct paths to production: 30-40% of DIU prototype OTs transition to production—often non-competitively.
“If you get the prototype OT and everything goes well, you can be essentially sole-sourced into production capacity,” Greg explains. “That transition rate is actually pretty remarkable.”
The SBIR Roadmap
For companies earlier in their journey, Greg lays out the SBIR pathway that too many founders misunderstand:
Phase I ($50-100K): This isn’t about building a product. It’s about customer discovery and earning your “hunting license” to talk to military units. The real work is finding 2-3 potential partners who will write letters of support for Phase II.
Phase II ($1M+): Now you’re building actual prototypes with real end users. This is where the magic happens—where requirements become reality and relationships become contracts.
The key insight Greg emphasizes: “The units that will use your technology typically don’t have the money to buy it. Someone else is funding that purchase. Understanding that distinction changes everything.”
What GovClose Taught Him
After leaving DIU in 2024, Greg launched Five Side Strategy to provide fractional BD and advisory services to pre-seed through Series B tech companies. He also co-manages the Founder Institute’s Defense & National Security accelerator.
But before launching his own practice, Greg went through the GovClose certification program.
“The thing I love about GovClose is that it puts it all together and provides an actionable plan,” Greg says. “By the time you finish, you can actually understand how to go sell to the government. It’s not just theory—it’s a comprehensive how-to that anyone coming in off the street can follow.”
For companies at the intersection of commercial tech and national security, that knowledge is the difference between burning through runway and building sustainable revenue.
Ready to Navigate Federal Contracting?
Whether you’re pursuing your first SBIR, preparing for a DIU CSO, or trying to understand how OTAs could accelerate your path to market, the playbook exists. You just need to know where to look.
For entrepreneurs and sales professionals: The GovClose certification program provides the comprehensive federal contracting education Greg wishes he’d had when starting out. Learn the same strategies that helped him transition from Shark Tank to serving as a trusted advisor to defense tech companies. Start your GovClose certification today →
For companies ready to hire: Greg Coleman is one of 230+ GovClose-certified professionals who understand both the commercial tech world and the federal acquisition process. If you’re looking to hire someone with this rare combination of skills, visit Match.GovClose.com to connect with qualified candidates →
Watch the full interview above to hear more about Greg’s experiences flying presidential missions, the technologies he helped fund at DIU (from beta voltaic power sources to hybrid-electric autonomous systems), and his specific advice for navigating the defense innovation ecosystem.
Connect with Greg Coleman:
Email: [email protected]
Founder Institute Defense Cohort: fi.co/defense
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