38. Harvard Law, McKinsey, and the Rules That Make Maine Housing Expensive with Aaron Chadbourne

Aaron Chadbourne got his real estate license the day after he graduated from high school. He sold his first house at 18 and took out his first mortgage before most people finish their freshman year of college. Then he went off and collected three degrees from Harvard, worked at McKinsey, and served as Senior Policy Advisor to Governor Paul LePage. And then he came home to run the brokerage his mother built.

I have been looking forward to this conversation for a long time, and it did not disappoint.

Aaron is the Designated Broker and owner of Demetria Real Estate in Greater Portland, and he was just named 2026 REALTOR® of the Year by the Greater Portland Board of REALTORS®. What makes him interesting is not the resume. It is that he can look at a housing problem from the policy side, the capital side, and the kitchen table side all at once, and he does not pull punches about what he sees.

We spent most of this episode on a question I think about constantly: why is it so hard to build housing in Maine? Aaron's answer is that it is not lumber and it is not labor. It is the rulebook. There are more than 9,000 jurisdictions writing their own housing rules across this country, and Maine has its own version of that patchwork. I share a story from a property I was on that same day where a three unit building needed three separate septic tanks, even though the whole thing has five bedrooms and the 200 year old farmhouse down the road with five bedrooms gets by on one tank. Aaron walks through the sprinkler ordinance in Gorham, the roof pitch requirements that quietly ban manufactured housing even after the state legalized it, and the shoreland zoning question he still cannot get a straight yes or no answer on for his own camp.

We also get into the first time homebuyer number that should worry everybody. The average age is now 40. Aaron makes the case that we told an entire generation to delay homeownership in favor of college and credentials, and we are now living with the bill. He breaks down what a renter paying $2,000 a month hands over in ten years, tells the story of a 19 year old CDL driver who bought an old farmhouse in Baldwin and built $100,000 in equity in a single year, and pitches an idea I really like: a preferred mortgage product for Maine educators tied to a financial education requirement.

Other ground we cover:

Why capital goes where it is welcome and stays where it is appreciated, and what that means for Portland versus Westbrook

The difference between a code officer who sees himself as an enforcer and one who sees himself as an educator

What the ROAD to Housing Act could actually change for Maine builders and homeowners

Why only 5 percent of American construction is industrialized while Japan is at 45 to 50 percent, and what a building code rules engine could do about it

Whether AI is coming for the real estate agent, and why Aaron thinks the physical world and human trust still matter

Rent control, populism, and why Aaron would rather build ladders than freeze people in place