
Philosophy
A point of view about old buildings, good blocks, and the long run.
I’m not an activist. I’m an investor who loves Chicago neighborhoods — and thinks the smart money and the right thing point the same direction here.
The signature home
Chicago is losing its two-flat.
Walk through Lakeview or North Center today and you’ll see it happening: a handsome 1910 two-flat that held two families for a century, gutted and reborn as a single oversized house. Multiply that by thousands.
The two-, three-, and four-flat is Chicago’s signature building — a quarter of the city’s housing and the largest source of its family-sized, lower-cost homes. It’s also disappearing fastest in exactly the neighborhoods we invest in.
The data
The disappearance, by the numbers.
4,800+
two- to four-flats lost in Chicago since 2013 — about 11,775 homes.
47.5%
of those buildings were converted into single-family houses.
#1 & #2
North Center and Lakeview lead the entire city in two-flats lost to single-family conversion.
Source: Institute for Housing Studies at DePaul University, Patterns of Lost 2 to 4 Unit Buildings in Chicago (2021).
Why it matters to me
The original City of Neighborhoods.
Here’s what I actually love about these blocks: the mix. The two-flat is the building that lets a teacher, a young family, and a retiree share the same leafy street. Lose the building and you lose the mix — the block quietly empties of everyone but the people who can buy a single-family house.
Chicago earned the name “City of Neighborhoods” honestly — block after block of different people, trades, and origins living shoulder to shoulder. The walk-up is a big part of why. Keeping these buildings full keeps that Chicago intact.


The story behind the name
Every family worth its salt has a crest.
Heraldry is how families have marked what they stand for — and what they mean to pass on. The name Heraldic is quietly built from the names of my two children, Charlie and Reid. The ladybug is hers; the kart, his. This was never only about buildings. It’s about leaving something behind that’s worth their name.

