In 2004, Rich Toscano launched Professor Piggington’s Econo-Almanac for the Landed Poor.

I asked him the other day to explain why he did it:

In order to inform my own financial decisions, I became very interested in the question of whether real estate was in a bubble or whether the price rise was legit. I didn’t find much in the way of good analysis on this question, so I started digging into the data myself. Upon doing so, it became very clear to me that there was a massive speculative bubble underway.

My friends and I had been debating the “bubble or no bubble” topic for a while, so of course I set about showing them all my graphs and evidence. At some point I decided to just put it up online and refer people to the website.

To his surprise, more than just his friends found it interesting.

Its central thesis was that the housing market had reached unsustainable heights. It would come down.

This, of course, was absurd to many: buying or keeping your house was a no-brainer at the time.

But Toscano stood apart.

He explained things with a comic flair and conversational writing style that was so attractive, the site started making him money. He even began charging for premium content and eventually decided to dump his career as a software engineer and become a money manager.

(Full disclosure: I discovered him while wrestling with the decision to sell or keep a condominium in 2005. We decided to sell it, in large part, because of his analysis.)

Toscano became San Diego’s most beloved housing bear. National reporters would call him for the token quote about how things might not be as peachy as everyone assumed.

He had haters too. Lots of them. Many shared the belief that housing prices would never collapse. Maybe, some would concede, a “soft landing” was on the way.

In 2005, Toscano also began writing for us. His insights helped us justify investing reporting talent in covering the housing market, which we were proud to provide independent perspective on in 2005 and 2006. For a while, we were best known for our political coverage but best read for our housing coverage.

Then, the housing market plummeted. And you know the story from there.

All the while, Toscano watched. Nope, still unsustainable. Still high. Over and over someone would say we’d hit bottom and Toscano would say, “Yeah, doesn’t look like it.”

But over the past several months, he changed his tune. Homes were now almost cheap, with mortgage payments finally competing with rents. His graphs were starting to look not so distorted.

And just last week, Toscano completed the purchase of a house.

Who knows if this really is the bottom of the housing market? But as he explains in this week’s VOSD Radio, it made sense to him to buy.

It’s a great conversation, I think. Give it a listen.

And congrats, Rich!

I’m Scott Lewis, the CEO of Please contact me if you’d like at or 619.325.0527 and follow me on Twitter (it’s a blast!):

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Scott Lewis oversees Voice of San Diego’s operations, website and daily functions as Editor in Chief. He also writes about local politics, where he frequently...

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