Stories on tap: Microsoft vet consoles and entertains with talks at his Seattle-area bars

People have been offering their hot takes over cold beer for centuries. James Whittaker is no different.

But with distinguished runs at Microsoft and Google, the PhD computer scientist and former college professor is telling tales with a unique twist. Whittaker can talk tech — and more — with the best of them, and he likes to do it over beer that he brews in the bars that he owns.

Tuesday night in Kirkland, Wash., a couple blocks from Google’s sizable campus in the city, Whittaker held court at his Side Hustle Taproom for one of his “Career Storytelling” classes.

“I hope I don’t suck,” Whittaker joked as he poured himself a pint of pilsner from Bellevue Brewing Company, another establishment where he’s an investor/owner.

The place filled up quickly, perhaps in part on the strength of a recent viral LinkedIn post, in which Whittaker said he had to console a couple Microsoft managers at his Side Hustle location in Bothell after they had to lay off large swaths of their teams.

“They were sad to their very cores and bartender therapy (seriously the best kind of therapy) ensued,” Whittaker wrote, offering details on how he was told the layoffs took place with no warning, and how stress is high and morale is low at the Redmond tech giant. Microsoft cut approximately 6,000 employees from its global workforce in June, and a few weeks later another 305 got laid off in Redmond.

In his post, Whittaker also offered his views on how AI isn’t working, large language models cost too much and do too little, and — after appearing way behind — Apple will likely figure out some AI device that wins the whole race.

“I haven’t had a viral post for a while,” Whittaker told GeekWire. “But every time I say something derogatory about Microsoft, it tends to take off.”

From professor to Microsoft

Whittaker earned his computer science chops at the University of Tennessee in the late 1980s for a doctorate that used an AI algorithm — “we used to call it pattern analysis,” he quips — to predict bugs in software using IBM data.

He spent 10 years as a computer science professor at Florida Institute of Technology before moving west for his first stint at Microsoft, in Windows security, from 2006 to 2009. He quit to go to Google for three years, building Chrome and Maps.

Microsoft lured him back in 2012 to work on what he said is now Bing AI.

“It was called Internet Platform and Experiences back then,” he said. “Microsoft’s never been good at naming shit.”

Whittaker lasted 7 1/2 years in his second run at Microsoft, with a chunk of that as distinguished engineer and technical evangelist. Speaking gigs at the company took off when he said he was asked by current Microsoft CEO Satya Nadella, then the president of the company’s Server and Tools Division, to move into the Developer Division and “reboot the Azure sales staff.”

He started doing regular keynotes at executive briefing centers at Microsoft.

“I’m known for explaining complicated things in very simple terms,” he said.

Whittaker got sick in 2018, tried to go back to work in 2019 and realized he was done — the office, the meetings, the traffic were all too much. He retired and turned his focus to brewing beer and opening taprooms.

“It’s a coincidence that the thing I’m the best at, which is AI, didn’t kind of surface until I was already retired,” he said. “I get offers to go back, but I just can’t do it.”

Cheers to being human

Despite his skepticism about AI and whether LLMs are doing anything useful for how much money is being poured into them, Whittaker is finding his own clever ways to use the tech. He’s especially bullish on smaller models that do specific tasks rather than large models that need to be trained on everything.

When his mother was dying last year, he wrote a custom GPT that served as her online buddy.

“All I needed for my mom was Lawrence Welk, Catholicism, and the menu at the nursing home,” he said.

While artificial intelligence found its way into Whittaker’s event because it’s the only thing people seem to be talking about these days, his bar talks usually focus on how to tell a story. The aim is to help people in tech and elsewhere get ahead in their careers by learning how to tell the right story at the right time to spark a deeper connection.

“I’m not doing that tonight,” he said Tuesday. “I’m just going to tell stories that worked for me in my career and encourage you to find similar stories that you can tell to help you succeed.”

Over the next two hours he told at least five tales from his tech career, sprinkling them all with a healthy dose of self-confidence and profanity wrapped in a Kentucky drawl. His stories were about what he said, through chance encounters or pre-arranged meetings, to prominent tech leaders.

They included a 1997 meeting with Bill Gates in which Whittaker said he shook the Microsoft co-founder’s hand and played off the company’s famous tagline by saying, “I test software Mr. Gates, because a broken computer on every desk and in every home is no contribution to humanity.”

In other tales, Whittaker described how he managed to spark meaningful reactions — from his PhD professor as an unknown computer science student; from Netflix co-founder Reed Hastings in first class on a flight; from Google co-founder Larry Page at an office men’s room urinal; and from former Microsoft CEO Steve Ballmer during a job interview in which Whittaker spelled out how Bing could compete with Google on search.

All of the interactions were keen examples of human connection, which served as a fitting juxtaposition against the AI themes Whittaker touched on earlier and in his LinkedIn post.

And, at one point in his bar, with a beer in his hand, it was all worthy of a toast.

“We’re all here together as humans. We’re not AI,” Whittaker said. “And I think maybe bars are the last bastion of humanity where we can sit together and look each other in the eye, and we can flirt and we can talk and we can cry and we can commiserate.

“Here’s to being fucking human. Cheers, everybody.”