After a lead investor in a round of funding abruptly shifted interest, Addressable was unable to cover a bank loan and existing business commitments, leading to a sudden shutdown Thanksgiving week.

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This article was last updated Dec. 18, 2023.

Direct mail marketing company Addressable abruptly went out of business the week of Thanksgiving after a round of funding failed to materialize, rendering it unable to cover the cost of operations, according to its founder and CEO, Chris Tosswill.

Reached by phone on Dec. 18, Tosswill told Inman he is limited in what he can share about the closing by an NDA, but explained that the company was very “cash-constrained,”
and when the round of funding collapsed, so did the company.

“We were basically two weeks away from receiving a significant amount of additional capital. And when that round fell apart, I spent the next two weeks scrambling to try to find additional financing, additional investors, but was unable to make that happen,” Tosswill said. “It was a fatal cash crunch.”

Initially, the company left only the following message on its website, which has since been updated with a simple form to request more information about account status.

“It is with a heavy heart that we announce Addressable is halting operations. We were unable to secure additional financing to keep the business operating at this time. We will not be able to  fulfill any current or future mailings at this time.”

Inman discovered the shutdown in an attempt to contact Tosswill about serving on an Inman Connect Panel about artificial intelligence. Tosswill studied the technology in college and used it in the company.

Preston Holmes, who led public communications with Addressable, responded via text at the time, merely saying he no longer works with the company.

Inman was contacted by customers of Addressable seeking information about the abrupt closing, one having only recently opened an account with Addressable, paying them close to $13,000.

“You have to prepay everything with them, and use your credits within six months, but it takes some time to get your campaign up and running,” said agent and broker John Rainville of the Brokers Realty Group Limited in Lewisberry, Pennsylvania.

“I was going to send to nine neighborhoods around my office, and we hired a company to confirm the addresses, and I have two huge billboards up in my market in that neighborhood, and had heavy web marketing with Adwerx and Nextdoor,” Rainville said.

Rainville said he’s “chasing Baby Boomers” and direct mail resonates well with that demographic. His plans were to send 2,000 mailers before Addressable went into “reverse stealth mode.”

Tosswill admitted to Inman that the closing “could have been handled better.”

“Addressable had a large loan with the bank. And so at the moment in which it looked like the business was no longer able to repay that loan, the loan immediately defaults,” Tosswill said.

He stated that he is not in control of the company’s next steps, and that its assets are now owned by the bank. “One of the assets is the customer list and you know, all the technology and everything.” Tosswill said a mediary is handling all communications with customers and, in essence, sorting through the rubble.

The company’s catch has been its robotic “handwritten” postcards. It had also implemented a ChatGPT-based content creation tool it called SmartCopy.

“Addressable has always been committed to providing innovative solutions to help our customers grow their businesses,” said Tosswill in March 2023. “This feature will enable real estate agents to generate highly personalized marketing messages at scale, helping them acquire more listing appointments and grow their businesses.”

In an April 2023 Inman review, Addressable was noted for multiple features to support direct mail marketing.

“Complimenting its direct mail offering is Addressable’s Listing Architect, a solution that builds landing pages for properties. Users need only upload a few photos, enter some property features and a narrative tone, and a few paragraphs of very usable copy are generated,” the review stated.

Asked specifically about what he’d like to say to customers, Tosswill said that he appreciated everyone becoming customers and that “it’s not how I wanted it to go.”

“If you look back at what we’ve done over the last five years, it would show we created an incredible amount of value for a lot of agents,” Tosswill said. “And I wanted to continue to do that and I was working up until the final minute when, basically, we could no longer continue to operate. I lost something that I spent five years building and 50 people who worked for Addressable lost their jobs over the holidays and many customers were out their investment in marketing plans. It’s horrible all the way around.”

This story has been updated with quotes from the company’s CEO and founder, Chris Tosswill.

Email Craig Rowe

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