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 buyer, a private equity firm, or a buyer like Harbor that keeps the team in the town where it grew up, and owners consistently choose the path that protects the legacy. Harbor backs that up with flexible structures, using earnouts, seller financing, and varying equity so the deal fits the owner.
His most timely insight is that trust outlasts any single asset or revenue stream. When tungsten prices spiked because of China and hit his machine shop, Harbor could call a congressman who came to walk the shop floor. Andrew credits relationships, built in part through writing openly on LinkedIn, for access that does not show up on a balance sheet.
Perfect for owners weighing succession, investors interested in longer-hold alternatives to private equity, and anyone curious about how local ownership shapes a regional economy.
FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/andrewdunlap
FOR MORE ON ANDREW DUNLAP:
https://harbor.capital
https://www.linkedin.com/in/dunlapandrew/
FOR MORE ON COREY KUPFER
https://www.linkedin.com/in/coreykupfer/
https://www.coreykupfer.com/
Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.
Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Episode Highlights with Timestamps
[00:00:00] - Introduction and overview of Harbor
[00:01:48] - Andrew's first deal, a two-for-one lawn-mowing bulk rate
[00:02:42] - How he stumbled backward into building Harbor
[00:05:05] - The recirculation research, 52 to 53 cents local versus 14 cents once a headquarters leaves
[00:13:25] - The untimed fund and avoiding caffeinated decisions
[00:21:00] - The Clark Precision Machine acquisition and the owner's five-year contract
[00:34:54] - The red flags that kill a deal and the earnout bluff test
[00:45:32] - Why trust is the only currency that always matters
[00:49:40] - The freedom question
Guest Bio
Andrew Dunlap is the founder and CEO of Harbor, a holding company that buys established Virginia businesses to keep them in the state. He grew up in Baltimore, moved to Roanoke a decade ago, and came into acquisitions after coming out of a venture-backed startup in Richmond in early 2024, where he had helped build a software company with users in 60 countries. Harbor's leadership also includes M&A and securities attorney Tad Fisher and operations leader Krista Glassburn, who previously ran a manufacturing company in Tazewell, Virginia and grew it from 15 to 190 million dollars while acquiring seven companies. In its first two years, Harbor has acquired a CNC machine shop, a FINRA-registered broker dealer, and moved toward closing on an industrial services company.
Show Description
Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster.
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Keywords/Tags
Andrew Dunlap, Harbor, buy and hold holding company, keeping businesses local, Virginia acquisitions, mergers and acquisitions, business succession planning, alternative to private equity, earnouts, seller financing, deal structure, CNC machine shop, FINRA broker dealer, metal fabrication, economic recirculation, DealQuest Podcast, Corey Kupfer
