At 22, Garry Tan watched a bug fix stall in a big company's maze

Garry Tan was 22 when he walked across the highway in Redmond with a baseball bat.

He was a young engineer working on Windows Mobile, Microsoft's early system for phone-like handheld devices, years before the iPhone. His team needed help from the Windows team, which worked in a separate set of offices across the road. Tan said he and his mentor, a product manager, made the trip because emails went unanswered and bug reports went nowhere.

"They wouldn't reply to our emails, they wouldn't fix our bugs, they wouldn't even mark it as won't fix, they just ignored us," Tan said. He said he did not know why his mentor brought the bat. It was not to hurt anyone, just a vague threat. He called the memory hilarious now.

Tan, now the president of Y Combinator, the startup school that funds and coaches young companies, tells the story to explain what he thinks is broken about big companies and what should replace it. The middle layer of managers who route requests, track dependencies, and resolve conflicts, he argues, should be software agents, programs that can do office work on their own.

The problem, as he remembers it, was not that anyone was cruel. It was that there were about seven levels between his team and the person who could fix the problem, and that person never learned that Tan's team had spent four hours chasing what he described as a low priority bug that he thinks was blocking a thousand users.

"What kind of bureaucratic hell is it," he said, where two capable engineers are stuck because of a distant fiefdom. He wondered aloud how much humanity is wasted in that kind of delay, and how many anxious 2 a.m. wake-ups happen because someone wanted to avoid a hard conversation.

He ties his fix to that Microsoft experience. He recalls once getting an iPod and doing competitive research comparing it with Windows Mobile. Separately, he imagines that today a team there could use a simple text file with instructions, called a markdown file, paired with a reusable skill that runs automatically on a schedule to track team status. It would map who is working on what, who is blocked, and who is blocking them.

That loop, he said, could let a team release in a day or two something that once took six months. In his version, senior leaders still set direction and individual workers still do the work, but agents handle the organizing in between. Startups, he said, must work that way, even if giants like Microsoft cannot.

No baseball bat required.