NOTE: This piece was submitted for publication at a national outlet on September 4 — no response. So, posting the piece here. Just wanted to note that many articles on this very issue began to appear during the last few weeks. Sometimes letting your work go outside is risky when responses are not prompt.
The pajama boys – untucked, unshaved, uncombed, flip-flopped, with a vibe you got from junior high boys who spent too much time in the basement with National Geographic. Except the pajama boys had new tools in the basement: access to a database of porn. Pajama boys bring a volatile combination to the workplace—brilliant minds obsessed with juvenile pastimes.
We depend on their skills, so we tolerate their attire, responses (or lack thereof), and extra-or intra-curricular activities. But, pajama boy CEOs are dangerous. Pajama-boys are terrific entrepreneurs who destroy their own companies, if left to their own devices. Shortly after the IPO, culture problems choke the company.
Dov Charney grew American Apparel into a stunning success. However, he had an interesting wardrobe, even for a pajama boy. Sexual harassment suits against him and the company revealed problems with Mr. Charney remaining clothed. The company, which did not turn a profit after 2008, had to go through legal wrangling and Mr. Charney’s ouster as well as a bankruptcy filing before the board could wrest control from this determined pajama boy in 2014.
Martin Shkreli, former CEO of Turing Pharmaceuticals and author of the 5,000% price increases on life-saving drugs, was described by a potential juror during voir dire for his securities fraud trial, as a “snake.” Also ousted by his board, jurors at his trial, who came back with guilty verdicts, described him as “his own worst enemy.”
Upload, SoFi, and others too numerous to mention have the label of “bro cultures.” That’s the pajama-boy mentality. They create cultures that frighten female employees and silence the rest. Uber was a pajama-boy paradise. While the board pulled the cord on the ejection seat for former CEO, Travis Kalanick, it did so 4 years after he sent a “way harsh” memo warning employees to be sure that any sex they had at an upcoming company retreat was consensual. Asleep at the wheel would be one description for this board, but the culture had festered to the point that recruiting a CEO became a tall order. The board’s short list indicated its cluelessness. Bring in Meg Whitman? Nurse Ratched trying to rein in Jack Nicholson and the boys in a cuckoo’s nest. There would have been no pretty ending for that combination.
When pajama boys are company founders, there are only two choices. Bring in some adults early or face the Charney/Uber consequences. Sheryl Sandberg got to Facebook before Zuckerberg consumed the company. Pajama boy habits die hard, and a firm hand at the helm is a must. Marissa Mayer met resistance at Yahoo when she tried to make people show up for work, . . .in the office. The nerve of some broads. Her days were numbered before she even bought Tumblr.
Pajama boys are not well read in economics or history. So, they spout platitudes that have doomed societies in the past. Mark Zuckerberg recently offered us all a pearl, “Studies show that when working parents take time to be with their newborns, it’s good for the entire family.” Most of us already knew that and made the time, despite full-time jobs, in offices, to do so. Pajama boy techies are now out stumping for “universal basic income.” Been there, done that – see Venezuela.
Platitudes reveal a key trait of pajama boys: They don’t know what they don’t know. They miss consequences because they assert “feelings.” They want diversity, but fire the first whale to the surface who spouts a different view. Firing the young engineer with the memo on biology and diversity has cemented a culture of fear and silence at Google. Undaunted, Google then followed up by having one of their own think-tank’s scholars sacked for supporting the EU in its Google antitrust fines. In the isolated tech/Internet world, neither history nor views of those in the heartland make their way into the Silicon Valley offices’ foosball and beer rooms.
The missteps and pratfalls by pajama boys are numerous and legendary. The dot-com pajama boy debacles are too numerous to list. Zenefits: Why not develop a software program to create fraudulent licenses for your insurance agents? Theranos: Assume you have a blood-testing program that works without testing; just sell it. More pajama boy problems lie ahead. Elon Musk does not walk on water. In fact, Tesla is in for some frightening times as its spacey CEO enjoys free rein.
Apple had to get Steve Jobs out in order to give him a little growing-up time. He came back humbled and focused on products and a strategy of anticipating customer needs that customers hadn’t yet realized. That’s what pajama boys do well. But, they need either time to mature or adult supervision, and both require an engaged board. Without one of the two, pajama boys’ companies cannot grow up.