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Gregory has a verifiable track record in everything from politics to military engagements and from early- stage startups to enterprise business. Managing “clean-up” operations and turning around struggling companies.

Greg has had the honor of contributing to a congressional candidate chairman, and military wargame moderator. His experience spans early- stage startups, enterprise businesses, rollups, cleanups, turnarounds. He has built and exited 12 businesses, two of which won four PE Awards for transactions between $250M and $1B.

He has been published/quoted in over 100 publications including, Fortune, Entrepreneur, The New York Observer, The DEAL, and Thrive Global. He is a BenBella Book Author Forbes Contributor and has been featured or quoted in publications like Fortune, Entrepreneur, The New York Observer, The DEAL and Thrive Global.

From TEDx to crowds of thousands, he's had the honor of speaking on some of the most iconic stages in the world, is host of a Forbes Podcast and guest on over 100 podcasts, and has had TV appearances. He founded an early-stage startup investment syndicate, plus a startup school that powers universities, accelerators and government programs.

Gregory served as a strategic advisor to Campa-Najjar’s congressional campaign for the U.S. House of Representatives

We went from a $3.8MM to $40MM exit in less than two years. Enough said!

Gregory was instrumental in transforming my business from a service-based model to a successful product-based company. He not only helped me build a strong management team but also guided me through a successful exit. His expertise is truly invaluable—if you have the chance to work with him, consider it pure gold!

Gregory has a rare ability to craft a forward-thinking strategy, develop actionable plans, and execute them flawlessly. His skill set is incredibly hard to find—he's both a rare gem and impossible to replicate.

Working with Gregory was like plugging our startup into a power grid. His frameworks gave us clarity, structure, and speed — and his insight saved us from at least three expensive mistakes.

Gregory helped us understand not just how to grow, but when to slow down, standardize, and scale properly. His advice isn’t just smart — it’s timed perfectly.

Before Gregory, we were guessing. After Gregory, we were executing. His system is startup science, but his heart is all founder.

I learned more in weeks then i have in years!

Teaming up with Gregory Shepard for our company, Protectionary Solutions ApS, was like finding a magic wand during our early “what now?” days — his laser-sharp insights and startup wizardry guided us through chaos with solutions tailored to our toughest challenges. His strategic brilliance didn’t just improve our operations — it transformed them with visionary planning and practical execution. Gregory is the go-to for any organization looking for consultancy that actually delivers.