Most founders spend years chasing a bigger exit — bigger multiple, bigger acquirer, bigger headline. Delano Massey built a $74M marketing agency, became the #1 minority-owned agency in the country, and then walked toward something entirely different: a legacy built on government contracting expertise, disability advocacy, and mentorship that outlasts any single company he’s built.
Delano Massey — known across the government contracting world as “Mr. B2G” — spent over three decades helping businesses win hundreds of millions of dollars in federal, state, and local contracts. He built Jacob’s Eye Agency from zero revenue to $74M, ranking among the top 5 marketing agencies in the country and becoming the #1 minority-owned agency in America — all while managing a life-altering injury from his military service that most of his professional network never knew about.
In this conversation, Delano and Kwame explore what it actually means to build a name that survives the business: the discipline the military instilled in him, the personal tragedy that reshaped his priorities, and the moment he realized his agency’s success was never going to be the legacy he wanted to leave behind.
WHAT YOU’LL LEARN:
- How military service shaped his risk management and discipline as an entrepreneur
- The real story behind building a top-5 marketing agency — and the theft that nearly derailed it
- Why he founded Mr. B2G & Associates and The Proposal Factory™ to help other businesses navigate government contracting
- How a private, years-long physical recovery shaped his public leadership style
- Why he’s building companies around impact first, revenue second — and what the data says about purpose-driven businesses
If you’re a founder thinking about what comes after the business — or wondering how to build a reputation that opens doors long after any single company is sold — this conversation is a masterclass in doing it with intention.
Guest Bio
Delano Massey is the founder of Mr. B2G & Associates and creator of The Proposal Factory™, an AI-powered government contracting operating system. Widely known as “Mr. B2G,” he has spent over 30 years helping businesses win hundreds of millions of dollars in federal, state, and local government contracts. A retired U.S. Army JAG Corps veteran and former EO Atlanta President, Delano also founded Jacob’s Eye Agency, grown to $74M in revenue, and leads Eradicate Impairment and New Vision O&P, organizations focused on prosthetics and recovery care for underserved communities.
Connect with Delano Massey:
Websites:
https://mrb2g.com/
https://jacobseyeagency.com/
https://www.linkedin.com/in/delanomassey/
Will your name outlive your business?
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