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I recently wrote about how the cannabis industry has been rocked by losses and layoffs in 2019, and this troubling news hasn’t been strictly limited to growers, producers, delivery services, and dispensaries. Last week brought the news that cannabis media organizations are being hit hard, and one of the giants of the sector may be going down fast.

Print publications of all kinds have been facing financial challenges, but recent reports indicate these are very low days for High Times, the longest running nationally available cannabis publication, which has been in print since 1974. Beginning in April last year High Times went on a buying spree scooping up Green Rush Daily for $7 million, Dope magazine for $11.2 million, and Culture magazine for $4 million.

The impact of these purchases may not have been noticeable to readers, but were keenly felt by the magazine staffs almost immediately. Dope magazine laid off a dozen employees shortly after the High Times acquisition in 2018, and in October of that same year, completely shuttered their Seattle-based headquarters, firing another 11 staff members and transferring operations to its Los Angeles offices, with a mere three staffers being offered the opportunity to join them.

The purchases of these three assets were structured around the payment of a combination of cash and High Times stock, but trouble began shortly after the ink had dried on the deals. In June of this year, Culture magazine announced they were suing High Times over the alleged failure to be paid their promised $4 million.

The stock portion of these deals accounted for a majority of the purchase prices—for Dope magazine, the estimated $11.2 million purchase price involved $1.2 million in cash and 909,129 shares of High Times Class A common stock, which at the time was valued at $11 per share. Green Rush were promised $500,000 and 577,651 shares of stock. Both magazines may be wishing they'd gone for all-cash deals instead.

In March 2018, High Times announced they were planning to offer stock on the Nasdaq to investors in a model akin to crowdsourcing. Over 23,000 investors poured in $15 million, only to find that—surprise—the listing with Nasdaq didn’t materialize. Since then High Times has announced and then pulled back on several subsequent promises to launch trading on Nasdaq or over the counter (OTC).

Those investors may soon wish they had invested elsewhere. Celebstoner spoke with a securities specialist, who said that if High Times can’t manage to get the shares listed on Nasdaq or any OTC platform, investors are screwed. “Do investors easily get their money back if High Times doesn’t manage to list its shares?" asked the analyst. "The short answer is no.”

Cash is part of the issue High Times is having with getting their stock listed. Nasdaq requires companies who wish to list their stock to have $4 million in stockholder equity. High Times doesn’t have that—in fact, according to Marketwatch they are presently over $105 million in debt. “In its most recent earnings report," Marketwatch writes, "High Times Holding incurred a net loss of $11.9 million for the six months ended June 30, 2019, on revenue of $10.7 million.”

This is leading to speculation by some that High Times may not be around much longer. The company made an announcement which read in part, “because of recurring operating losses, net operating cash flow deficits, and an accumulated deficit, there is substantial doubt about the company’s ability to continue as a going concern for one year from the issuance of the financial statements."