woah woah... a bartender becomes the head of engineering at a high flying start up? This isn't the .com. Did the bartender also go to MIT?

Drug fueled founder parties? Orgies? I've clearly been doing silicon valley wrong. Or right, depending on your perspective... but not this? I've seen board game fueled parties where maybe one or two people do drugs, but it remains very nerdy? And no sex parties. Mostly sausage parties?

... so yeah. Do people really know Jims? Because I just read posts about them.

“presumably under the influence of some strong chemicals”

This is a bigger problem in Silicon Valley right now than anyone seems ready to acknowledge.

Interesting. I am sure there are Jims outside of startup world too. There will be finance Jims and entertainment Jims.

Is having a couple of pets and a ridiculous table lifestyle creep. Maybe. I think of lifestyle creep more in terms of you are not saving any money at all.

I think that comment is more telling of what is expected of founders and engineers. At least from authors point of view.

No life allowed. Definitely don't reproduce. You work, and work so you can work more.

Bit of an aside but I found it somewhat amusing that one example the author uses of Jim’s financial recklessness was getting into home brewing.

Home brewing is one of the cheaper hobbies available (though like all hobbies you can spend as much as you want). The only real requirements are a bucket and a pot.

I've met a few people like that, through what appears to be pure determination, they force success to give up what it has. Very impressive.

Drugs are bad, mmkay

You really have to believe your own narrative to do well as a startup founder, even when evidence is initially scant. This likely also has a tendency to slide into self-delusion.

I think much of this comes down to wanting to be a type of person vs. wanting to do the actual thing.

It’s easy to be consumed by “I’m the wealthy San Francisco founder guy” and doing everything that lifestyle requires, including things that may not be good for you.

I don’t trust anyone who has the general, abstract goal of being a “founder”. If there’s no great idea to go with it, it just seems like vanity. And sure it does work out really well anyway sometimes, but it’s just something I can’t get behind aesthetically.

This gets to a point my dad always made when I was neck deep in startups; so many of them felt unserious. People go to the most expensive west coast city, raise money, and then move to the next most expensive east coast city and open a second office. A lot of founders are clearly inexperienced, and to defend their inexperience, hire under experienced teams. It all sort of gets back to the root of the issue, which is that the hardest part is never the engineering, it’s networking and finding product market fit. Finding people who actually get up and do meaningful things is hard, and so Jim’s sneak in under the guise of being an outsider who understands a market and can make things happen.

Founder culture definitely has fraternity vibes - people with no other discernable talent other than being above average looking and having connections with other similar people end up in positions they have no real idea how to do.

In other words, there are a lot of people "playing startup" in the valley - some of the VC money flows too easily and there is always going to be an ecosystem of people to try to put it to work.

There are different kinds of founders in Silicon Valley now. Some are more like founders from the previous generation, like Steve Jobs and Steve Wozniak. Others are more like Elizabeth Holmes and Adam Neumann.

There are lots of earnest, sincere, and interesting founders. There are also lots who probably would've been happier on Wall Street.

I mostly stayed clear of the SV world while building and exiting my startup, but people like this came and went through my network constantly. They were always easy to pick out based on how much they glorified certain SV personalities and were desperate for their approval.

There's more truth to the "Forbes 30 Under 30 to prison pipeline" than people give it credit.

It's really hard for me to understand that people who have the chance to achieve basic financial independence (say $1M net worth) don't take that chance and make sure to stay financially independent forever.

If you do that, you're almost guaranteed to stay in the top 2% globally for the rest of your life. You've made it in life, at least financially.

The approach of not taking advantage of the lucky and privileged situation exposes you to a huge risk that your NW will go down to zero and you never get a second chance.

> Jim had participated in drug-fueled “founder parties”, group orgies and all other crazy experiences in San Francisco. This naturally led to the breakup with his fiancée and a nervous breakdown.

The Bay Area is a weird place. There are countless companies staffed by smart people doing amazing things. There are also countless people cosplaying as smart people and founders who are going through all of the motions, but producing little value.

In my experience (which is as limited as any other one person's experience) the environments at the companies doing the amazing things are on the boring side. Nobody wants to hear about those because it's uninteresting. So instead all of the public stories are about crazy parties, quick wins, huge exits, and the glamorous stuff.

People go there seeking it out. Some get lucky with some early wins, like Jim from this story. But when the time comes to do work, they flounder and get pushed out, also like Jim. It's a big place, though, and there's always some connection willing to hook you up with another referral if you press hard enough. That's the step where the performative, partying people start getting grouped up with other performative, partying people, and it snowballs from there.

Meanwhile the real companies are off quietly doing boring work and getting things done, pushing the Jims out if they accidentally get hired or acquired into the fold. It's a weird place.

> A few months post-acquisition, he got fired for an allegedly silly reason, but my intuition is that he was coasting hard and couldn’t focus at all because of home office and lifestyle creep.

This seems like a pretty dubious conclusion to make from the outside. There are a lot of reasons somebody would get fired after an acquisition. Hell, even if he was coasting, an acquisition followed by a rapid change in environment and culture can cause somebody to lose motivation for a wide range of reasons. Blaming this on "lifetstyle creep" is rather premature and, frankly, pretty judgemental or moralistic.

This is downstream of a pretty frustrating belief I've seen repeatedly in the tech industry: that whether a person is "motivated" or "hard working" is some kind of inherent quasi-moral characteristic of the person, rather than something substantially affected by environment. But hey, it's much easier to blame individuals and lean on the perf review process than it is to change organizational culture or leadership!

Real bummer of a story.

> He approached me because he was really into startups and wanted to become a tech entrepreneur, and make the big bucks

It's a shame that so much of tech culture has become about money. Money was always a part of it, but living in the Bay in 2010, there was more of a focus on building things. But once people started getting rich, especially off bitcoin, it brought in a whole host of people whose primary passion seemed to be money. We moved out in 2018. Still bums me out, SF was my favorite city, and I hoped to live there for a long time, but the values weren't my values anymore.

Ultimately this comes down VCs who fund people like this. Can we really believe the established funds look for "independent thinkers" anymore?

Airbnb’s CEO, for example, is a Jim who got lucky