How Medium finally pivoted its way to profitability
CEO Tony Stubblebine reined in spending and figured out how to actually reward high quality writing.
For Jason McBride, the nervous breakdown came very suddenly, but it was also years in the making.
If asked to tell the breakdown’s origin story, he’d trace it back to his sophomore year in high school, which was when he decided to become a lawyer. By then, he’d grown obsessed with politics, government, and political history, to the point where he found himself reading texts like the Federalist Papers during his free time. “I was a weird kid,” he told me recently.
Things started to feel awry soon after McBride enrolled in law school. “During the first semester, I'm like, oh, this sucks,” he said. “This is horrible. I don't think I really want to be here.” His classmates were hypercompetitive, and the curriculum discouraged the kind of intellectual curiosity that drew him to the law in the first place. “That really wasn't the point of law school. The point was to teach you to think in a very structured way, to get you into this groove. It’s all just about getting you ready so you can pass your bar exam.” Before the end of his first year, he realized that what he should have done was pursue a PhD in political science with the goal of becoming a college professor, but by that point the sunk cost fallacy had firmly set in. “I was like, yeah, law school's expensive. I've already got a semester in. The only way out is through, so I guess I'll just plow through.”
By the time McBride passed the bar exam, he knew he didn’t want to work for anyone. Two clerkships during his second year had disabused him of the idea of a career in government, and he didn’t want to spend 80 hours a week doing grunt work at a law firm. He knew several solo practice attorneys and decided to rent out office space in the same building as another lawyer he was friendly with. For those first few years, he mostly took on overflow work from other firms — a grab bag of cases across civil and criminal law. He enjoyed helping clients, but he didn’t like interacting with judges and other attorneys, so he’d dread appearing in court.
About four years into his career, McBride began to zero in on a combination of immigration law and IRS tax defense, two areas that he found somewhat interesting and weren’t well covered by other firms in the area. He was still young, but he’d already come up with an idea for an escape: “I thought that if I can bring in other attorneys, teach them the stuff I knew, maybe they can just buy me out, or I can have a very limited managing role.” Though it sounds ludicrous in hindsight, he thought building out a law firm would provide him with a shortcut for exiting the law.
McBride’s mistake soon became apparent, and he only compounded it with more mistakes moving forward. He tried to hire lawyers with similar skillsets to his, but they often dropped the ball, leaving him to clean up after their messes. He was reinvesting everything he made back into the firm, and each new hire put it in an even more precarious position, to the point where he always felt like he was on the brink of financial ruin. “I ended up finally with a really good office manager, and she helped out quite a bit, but I'd already dug too deep of a hole with all the staff that I had hired without any kind of strategic growth plan.” At some point he started seeing a therapist who diagnosed him with two anxiety disorders that stemmed from a combination of depression and ADHD. That certainly explained why he was throwing up every day before work.