This post was first published on my personal blog.

Weird things have happened all my life, but my relationship with Petra Koegel has to top them. I’ve been mulling it over for almost 20 years, and much more so following major psychic upheavals that began, and have continued since, August 2019.

Rather than throw around my and a few others’ opinions about what it all means — much of which is too fantastic for me to publish — I thought I’d present some evidence and let the public decide.

The Dalio Connection

Not long after moving to New York City in the fall…


Not sure what’s happening in this picture. Courtesy of Katerra. Or is it KATERRA?

This post was originally published in the blog for my new development company, The Change Order Group.

To anyone shocked at the pitiable state of construction startup Katerra — evidenced by Softbank’s recent $200M re-up investment to avoid bankruptcy — I would like submit this piece to voice an alternative narrative. Like their Softbank Vision Fund contemporary WeWork, the signs that Katerra was doomed were obvious from the start. I will highlight some of those signs and then explain what the Change Order Group is doing to present a qualitatively different and effective approach to market disruption.

Katerra first came…


This post was originally posted on my personal blog.

I have most of a first-draft that outlines the events of the last year and a half, which, for anyone close to me, knows have been the most difficult of my life. In the spring of 2019, I had a thriving real-estate innovation consultancy, an unrivaled professional network and reputation, an amazing and adventurous relationship with my two boys, superior health (running 5:23 miles), a serviceable relationship with one of the New York City’s most trophy-esque woman, and a boundless future to forward to. A year later, I was living out…


Hey Google, it’s me, David Friedlander. I know you have a lot of information about me. Many of your Sidewalk Labs team knows me directly — we’ve had conference calls, I know several of their partners, and I’ve tracked, written, and spoken on most of the project’s initiatives. I come to you as an intimate friend — one who needs to discuss a hard matter. We need to talk about Dan.

Few people know sidewalks — and crosswalks — like I do.

I know how attached you are to him. He’s your first — the one who alerted you to the crises that have befallen our global cities. I know he’s…


In August of 2001, I visited New York City with the objective of determining where I’d move next. While infinitely livable, my then-Boulder, Colorado home lacked the global scale I craved as a preternaturally ambitious 25 year-old man.

I wanted to make it big, and there wasn’t a bigger place than New York City at the time.

The other impetus for the visit was to attend my New-Yorker cousin’s wedding upstate in Rhinebeck. My august visit would be split between this high-society wedding (I shacked up at the Beekman Arms way before Chelsea C.) …


Next to procreation, bargain-hunting is surely one of humans deepest motivations. There’s a primal thrill in the prospect of using cunning to obtain a resource for less than its real value.

The bargain hunt and kill endorphin-rush support my crackpot evolutionary-psychological theory. In nature, the alpha individual must stay calm and patient in the throes of uncertainty. This is contrasted to the short-thinking masses who unload for pennies on the dollar at the first sign of disaster. …


The hotel-room I checked into yesterday was an unchangeably-frosty 64-degrees due to a likely-centrally-controlled-and-locked thermostat. I was advised by the front desk to find warmth via the PTAC — the exterior wall-mounted — heating unit.

In other words, it was recommended I balance out the blasting-AC by blasting the heat to arrive at the pleasant and cool outdoor temperature.

Then I saw it yesterday too: sprinklers missing their non-native-floral-targets amidst an all-day rain.

This is but a small sample of the quotidian — but in aggregate massive — stupidities I’ve witnessed in my 44-plus-years in the US.

I’ve seen tower-upon-tower…


Nesterly matches house and space rich seniors with cash-strapped millennial renters.

It will probably take a full-on economic meltdown to move urban housing markets away from high-end condos and rentals in prime locations. I get it, building is tough: the land is crazy expensive, most cities impose money and time consuming regulatory obstacles that would make a Byzantine bureaucrat blush, there’s no labor to build anything, and lenders shy away from any project letting off the faintest fragrance of risk. And then there are the other buyers and renters — those middle-market, debt-saddled, salary-plateauing masses yearning to be housed. Why bother developing accessible “missing middle” housing? …


“It won’t happen in New York,” that was the disheartening response of an architect friend about how to make cities affordable.* He had a point. NYC’s affordability situation is bleak, with more than half of its renters paying more than 30% of their income on housing (and many much higher). If treated as its own city, my home borough of Brooklyn would be considered the least affordable city in the country.

But it’s not just NYC. Around the country, it seems like most major cities — SF, LA, Boston, Seattle, Austin, and Miami — are beset with affordable housing crises.


Image credit

Few things are as backward as housing in the United States. Virtually everything about how housing is designed, financed, constructed, managed, and sold is beset with inefficiencies and outdated, analogue answers to modern problems. But this may be changing. A number of startups are bringing novel thinking and tech to fossilized sectors of the housing industry.

These approaches have caught the interest of VCs, whose waning interest in solving for things our moms used to do for us has sent them looking for more enduring opportunities. …

David Friedlander

Dad, runner, real-estate developer, story-maker, poet, data-pig, artist, armchair economist and astrophysicist.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store