Episode 415: Building a Permanent Home for Virginia Businesses with Andrew Dunlap

From a two-for-one lawn-mowing deal he negotiated with his neighbor as a kid to founding a holding company that keeps established Virginia businesses in Virginia, Andrew Dunlap shares his data-driven origin story, a fund built to avoid short-term pressure, and why he believes trust is the only currency that always matters.

Andrew is the founder and CEO of Harbor, a long-term, buy-and-hold company that acquires established Virginia businesses and keeps their teams, leadership, and jobs rooted in the state. In roughly two years he has completed three deals, including a CNC machine shop and a FINRA-registered broker dealer, with an industrial services company moving toward close. He describes himself as someone who stumbled backward into this work by digging into merger and acquisition data.

WHAT YOU'LL LEARN:

You will learn why keeping a company's headquarters local changes how much of its revenue recirculates in the community, how an untimed fund with no AUM fees removes the pressure to make what Andrew calls caffeinated decisions, how Harbor structures flexible deals to become the buyer owners actually prefer, the earnout test that separates a real growth forecast from a wishful one, and why Andrew treats trust as the most durable asset in any market.

ANDREW'S JOURNEY:

Andrew grew up in Baltimore and moved to Roanoke, in Virginia's southwest, ten years ago. Coming out of a venture-backed startup in Richmond in January of 2024, he noticed how few senior roles existed in his region, then pulled the merger and acquisition databases to find out why. He discovered that 87 percent of external buyers in Roanoke, and 82 percent across Virginia, were from out of state, which meant companies and their leadership kept leaving. The research he found showed that a locally headquartered company recirculates roughly 52 to 53 cents of every revenue dollar in its community, a figure that falls to about 14 cents once the headquarters moves to a larger city. That gap became the foundation for Harbor.

TRUST AS THE ONLY CURRENCY:

Andrew closed the conversation on a theme he keeps returning to. Trust, he argued, is the one thing that holds when assets turn and revenue streams dry up, and he sees it as underdeveloped in a digital, globalized world where people invest too little in relationships.

KEY INSIGHTS:

Andrew's foundational insight is that owners care deeply about who becomes the next steward of what they built. He lays out three options for a seller, a strategic