5 Conversations With Leaders I Admire That Stuck: Howard Chai

Five years into building PUBLiSH, I wanted to mark the milestone by sharing a collection of five honest conversations with people I admire.

A conversation with Howard Chai, Award-Nominated Real Estate Reporter

Howard is a journalist. A pattern spotter. Someone who deliberately covers what others overlook. Howard has built his reputation covering the business of real estate with precision, leaning into industry blind spots before they become headlines. His perspective on attention — who deserves it, who doesn’t, and why — reshaped how I think about signal versus noise.

Max: What’s your filter? How do you personally decide what’s worth paying attention to?

Howard: I pay attention to everything within the broad realm of what I cover (and many other things for my own pleasure), but there is a different calculus to decide whether to pursue a story.

I would say the primary thing I consider is whether other publications will cover the story.

If it’s something I think many will cover, I will often pass on it.

But if it’s something I’m confident others will not cover or cannot cover as well as I can, then I am more likely to pursue it.

Max: What signals do you trust most: data, instinct, editors, audience response, sources?

Howard: Sometimes it’s just my sense of whether something is newsworthy, sometimes it’s really just following my curiosity, with sources and expected audience response mixed in too.

Max: What’s getting too much attention right now, and why?

Howard: I think Canadian news organizations spend far too much time and resources on American news.

I took a screenshot of CBC’s homepage on January 27 and literally everything above the scroll (on desktop) was about the Minnesota ICE situation. It was a big story, I was following it pretty closely myself, but why is CBC dedicating that much space to it?

I get it, I’m sure it’s a traffic booster, but I think that is just crazy, particularly for CBC. There are news organizations that have to chase traffic in order to survive. The CBC does not, so I think it is such a waste and their resources could be better spent covering stories in Canada that smaller news organizations may not be able to cover.

Max: What’s not getting enough attention, but should be?

Howard: In the United States, there is an entire ecosystem of journalism focused on covering the journalism and media industry itself. There are full-time reporters who cover media companies, journalism issues, and things in that realm. Besides some one-off stories once in a blue moon, that pretty much does not exist in Canada. I get the feeling that it’s kind of a third rail topic for news organizations in Canada to cover other news organizations, but it shouldn’t be. I think the journalism/media industry actually suffers because of that.

Max: What’s one story you’re glad you leaned into early?

Howard: Real estate insolvencies.

I didn’t make a conscious effort to lean into it, but the first big insolvency was just too big to ignore, and in covering that saga, I learned a lot about insolvency processes. Then insolvencies just kept happening, so I made use of that experience.

There is also not a lot of competition there, in terms of coverage from other news organizations, so I felt like I could take advantage of that hole while covering what I believe to be an important industry-wide trend.

Max: What do you pay attention to that most people overlook — and why?

Howard: Court cases. I don’t think people realize how many potential stories are just waiting to be found there.