Shark Tank to Sam.Gov - The Real Money is in Gov Contracts

Every so often, I talk with someone whose career path immediately grabs your attention—not because it was planned perfectly, but because it unfolded in a way that most people would never expect.

Greg Coleman is one of those people.

On paper, his background doesn’t follow a straight line at all. He helped build a venture-backed tech company that landed on Shark Tank. He spent years flying high-profile missions for the U.S. Air Force. Then, instead of chasing the next flashy startup exit, he moved into a space most founders either ignore or misunderstand entirely: government contracting and defense innovation.

In our conversation, Greg breaks down what it really takes for startups, consultants, and small businesses to work with federal agencies—especially within the Department of Defense. He doesn’t sugarcoat the process. He explains how programs like SBIR and OTAs actually work, why so many companies get stuck after their first government contract, and what separates founders who break through from those who quietly disappear.

If you’ve ever wondered how companies get government funding, how innovation programs inside the DoD actually operate, or why some startups manage to turn prototypes into real contracts while others stall out, Greg’s perspective offers a rare, inside look.

A Career That Bridges Military, Startups, and Federal Innovation

Greg’s story starts long before startups and accelerators.

He served as an Air Force officer, flying VIP and aerial refueling missions across multiple presidential administrations—Bush, Obama, and Trump. That experience gave him something most entrepreneurs never have: a deep, operational understanding of how the military actually works, how decisions get made, and how technology is used in real-world environments where failure isn’t an option.

After his military service, Greg co-founded Sworkit, a fitness and wellness technology company. The company raised venture capital, scaled commercially, and ultimately appeared on Shark Tank, where it closed what was, at the time, the largest tech deal in the show’s history.

That experience matters more than people realize.

Running a startup—meeting payroll, answering to investors, managing burn rate, and constantly fighting uncertainty—gave Greg firsthand empathy for founders. That empathy becomes a critical asset later in his career, especially when advising early-stage companies trying to sell to the government.

Inside the DoD Innovation Ecosystem

Where Greg’s path becomes truly unique is what came next.

He spent years working inside the Department of Defense innovation ecosystem, holding leadership roles with organizations like MD5 (now part of the National Security Innovation Network), NSIN, and the Defense Innovation Unit (DIU).

In these roles, Greg wasn’t just observing innovation—he was actively managing it.

He evaluated early-stage technologies, ran prototype programs, oversaw multi-million-dollar portfolios, and worked directly with founders trying to navigate the government maze. He saw, up close, how the DoD searches for new capabilities, how programs get funded, and why so many promising technologies never make it past the prototype stage.

This is what people often call the “valley of death”—that dangerous gap between early research funding and sustained government adoption.

Greg’s work focused on helping companies cross that gap.

SBIR, OTAs, and What Founders Get Wrong

One of the most valuable parts of Greg’s insight is how clearly he explains programs that most founders find confusing or intimidating.

He breaks down SBIR (Small Business Innovation Research) as what it really is: the government’s version of seed funding.

SBIR contracts typically start with:

• Phase I, a relatively small feasibility study

• Phase II, larger funding to build and test a prototype

For startups, SBIR is often the first real entry point into the government market. It provides non-dilutive capital and access to military stakeholders—but Greg is quick to point out a critical truth:

SBIR alone does not equal long-term success.

Too many companies win SBIR funding and assume the hard part is over. In reality, SBIR is just the beginning. The real challenge is transitioning that technology into a program of record—something the government actually budgets for and buys year after year.

That’s where Other Transaction Authorities (OTAs) come in.

Greg explains OTAs as faster, more flexible contracting tools that allow the government to prototype—and sometimes move directly into production—without following the traditional FAR-based acquisition process. OTAs are often more founder-friendly, offer better IP protections, and move at a pace that resembles the commercial world more than traditional government contracting.

But again, access to OTAs isn’t automatic. It requires relationships, credibility, and a deep understanding of military needs.

Relationships Matter More Than Pitch Decks

If there’s one theme Greg returns to repeatedly, it’s this: government contracting is a relationship business.

You don’t win simply by submitting proposals or responding to solicitations. You win by:

• understanding the mission

• knowing the end users

• building trust over time

• showing up consistently

• and speaking the language of the operator, not just the investor

Greg’s military background gives him a unique advantage here. He understands how operators think, what they care about, and how new technology must fit into existing workflows. That operational credibility allows him to translate between founders and government buyers—two groups that often struggle to understand each other.

Seeing the Future of Defense Technology Up Close

During his time managing innovation portfolios, Greg encountered technologies that most people never hear about until years later.

He talks about:

• beta voltaic power sources capable of lasting decades

• maritime autonomous vehicles that can operate submerged

• hybrid electric propulsion systems for unmanned platforms

These aren’t science experiments. They’re real projects funded through government innovation programs—quietly shaping the future of defense capabilities.

For founders, this reinforces an important lesson: the government isn’t anti-innovation. It just moves differently.

What Greg Does Today

Today, Greg runs five5strategy, an advisory firm helping technology companies enter and navigate the government market. He also co-manages a defense-focused startup accelerator under the Founder Institute, working with companies from pre-seed through Series B.

His approach is practical, grounded, and refreshingly honest.

He doesn’t promise shortcuts.
He doesn’t oversell government contracts as “easy money.”
And he doesn’t pretend the system is simple.

Instead, he helps founders understand reality—and prepare for it.

Why Greg’s Perspective Matters

What makes Greg Coleman so valuable is the combination of experiences he brings to the table:

• real military operations

• real startup pressure

• real government decision-making authority

Very few people have lived on all sides of this equation.

For founders, consultants, and small businesses exploring government contracting for the first time, Greg’s story offers something rare: a clear, realistic starting point—without hype, without fear, and without guesswork.

If you want to understand what actually separates successful federal vendors from everyone else, Greg’s journey is one worth studying closely.

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