The next AI Roundup is almost ready to publish but first, a brief interlude on the most unlucky man I’ve ever worked with.
Hire me as CTO or tech lead for your next project.
Focus on growing the business, never worry about the tech again.
Slide into my DMs on X or Substack. Select portfolio at Deca Labs.
Unluck: when the Bill comes due
Bill was always a bit of a beta with a temper. He’d speak up, but get hurt easily. Often jealous, going behind people’s backs. Naive, often buying into dying projects believing they would succeed on his efforts alone.
None of these are quite fatal on their own, but if you make big bets and are consistently wrong, you’re going to lose. Bigly.
Back to Bill.
Last I worked with him, he was doubling down on a project I had slowly been backing away from. It was clearly losing leadership buy-in, internal customers were getting frustrated by delayed timelines, launch bugs were a nightmare, and it still wasn’t GA’d for a single end-to-end use case after two years of work from some of the Principal Engineers.
And yet, Bill still believed, and sunk another three years of his life into it. Grinding away, trying to unblock customers, trying to fix bugs himself even though he never quite got competent at the codebase.
But after the second year of layoffs, AI psychosis, and continued cultural malaise, Bill had reached the limit of what his anxiety medication could support. It was time to go.
Use Poaster’s custom AI model to pull the best quotes from your long form writing, and automatically post them to your socials.
Skip the army of virtual assistants, start today for $1/month.
So, Bill started interviewing and landed a gig at a tiny startup.
And then he wrote two sappy blog posts in back to back weeks explaining first that he was leaving and all the issues with the W2 which he hopes management eventually fixes, the second introducing the new job he was going to.
Bill was a good boy and submitted his two weeks notice.
But leave it to bad luck Bill to time his notice to be not even 10 days before the biggest layoff in company history.
While colleagues were given fat packages to leave, Bill received a brief email from HR informing him that since he had already given notice, he could simply stop working today, but there would be no severance package for him. He would not get to keep his maxed out corporate laptop. He would leave with the shirt on his back, and nothing else.
But, at least he had a new job lined up. A small solace.
In group chats in the coming weeks he pivoted quickly from being delighted with the small team dynamics and possible code velocity, to becoming incredibly dour at the engineering standards, manual operations process, hacky deploys with manual ssh commands.
Not even six weeks later, that startup showed him the door and he was now out of two jobs within two months, and no severance to show for all his efforts.
Safe to say, I wouldn’t be the lead investor in his next endeavor. He has an incredible knack for screwing things up and then kicking off his latest anxiety induced pity party for weeks on end.
Thank you to the readers who pay to make this newsletter possible.
Ready to turn your life around? Subscribe & start here and report back your wins.
This Substack is reader-supported. To receive new posts and support my work, consider becoming a free or paid subscriber.
Make your own luck
In closing, let us find in Bill’s experience some lessons that we can learn from, even while he remains nearly impossible of self-improvement himself.
Continue reading this post for free, courtesy of BowTied Fullstack.
