51–60 of 166 posts
Earlier quoted context omitted.
Do most people leave when they make a lot of money? Or do they stay and continue working?
From my expierence most people leave soon after they can cash out. It’s the top tier (VPs or people with a clear path to becoming one) people who usually stay
Success can hide a lot of problems. Companies with wildly successful products have a strong bias toward "we must be doing everything right," when in fact the truth is only "we did some things right at some point". That bias can make it hard to change things, even clearly broken things. It can make it hard to introduce new products, since anything new will be tiny compared to the old successful product. It can make it…
> "we did some things right at some point" or got lucky, but attributed the success to ability/execution instead of learning the right lessons. Then, because of over-confidence, make poor decisions and cause problems down the line leading to failure (as "luck" runs out).
There were a lot of things that we got ridiculous pushback on, justified as “at company X-1 we only needed 2 salespeople. We don’t need more than that at company X”. There seemed to be a lot of things where it seemed like he thought he’d figured out “the formula” when it was really just a lucky break. I didn’t stay long. 10 years later, they did have an exit, but it was on a dramatically longer timeframe than the first company had, and I suspect a lot of that had to do with bad choices that had worked out at the previous company.
Getting acquired and watching everything you built get rendered obsolete overnight. It's a good reminder that almost everything you build is fleeting. Especially in a startup where you often pour your heart and soul into a product. Ecclesiastes: > For a person may labor with wisdom, knowledge and skill, and then they must leave all they own to another who has not toiled for it. This too is meaningless and a great mis…
People. Success breeds some weird shit, especially if you were close to people, which happens a lot in startups with a high work ethic. Friends turn into strangers, friends turn into enemies. Some make more money than you — a lot more — and some make less than you — a lot less. Brews some weird undercurrent sometimes. Money changes things. Even if you don't make real money... the perception of success changes things,…
Successful companies also attract gold diggers. When the company is small, unless everybody is going above and beyond the call of duty, it's likely going to fail. As the company gets bigger, there is more and more latitude for failure. At some point it is successful enough that it can survive having people whose only goal is to direct a large amount of money into their pockets. This can lead to really weird decisions…
It can be a painful, frustrating, degrading, and ultimately extremely valuable lesson.
It's especially difficult if you're naive because everyone around you is talking about metrics and OKRs, you agree on OKRs with people, and everyone seems to be working toward their OKRs. Everything seems so objective! It takes quite a bit of experience to internalize that (a) metrics have a lot of momentum and lag, (b) shit changes too fast anyway, (c) managers will move teams/groups way before the goals materialize, and (d) by the time they've moved nobody will remember what happened two quarters ago.
So while everyone is talking about the OKRs, nobody who isn't hopelessly naive actually cares about them (beyond the top line stuff executives see). Your manager doesn't care at all if you meet your objectives. They just want to look good until they can move to bigger responsibilities. Sometimes that happens to align with meeting explicit objectives, but quite often there is no alignment at all.
The people who understand the covert goals will do well very well for themselves (at least until the future eventually catches up to them). The people who naively work on their OKRs usually will not.
I'd say there are a couple problems you're likely to have at a successful startup: 1) You (the early engineer) get promoted and are leading the charge, but have no mentors or role models to help you develop your career. 2) You raise a huge Series A / B, and everyone says "spend it in 18 months" so you hire a ton of people quickly, which significantly changes the company culture. Your first attempts at introducing str…
The best reason to work at a startup is if you are a founder and have significant equity. The other reasons to join are if you are enamored with a technology that they specifically use or want to get experience quickly wearing a lot of hats. There are no other reasons to work at a startup. You will work much harder, for less money, and poor benefits relative to larger companies. You work in uncertainty. Unless you ar…
For example, I’d guess the risk-adjusted return is better at a Series B company with product market fit, however you still have to be able to pick well.
But knowing a dozen people who made enough money to retire from joining early-ish at a company that had done a lot of the hard stuff I’ve gotta say it’s certainly not always true.
Earlier quoted context omitted.
Successful companies also attract gold diggers. When the company is small, unless everybody is going above and beyond the call of duty, it's likely going to fail. As the company gets bigger, there is more and more latitude for failure. At some point it is successful enough that it can survive having people whose only goal is to direct a large amount of money into their pockets. This can lead to really weird decisions…
> If you happen to be the hapless person who is innocently trying to make the company successful and who is not paying attention to where the money "should" flow, it can be quite painful for you. It can be a painful, frustrating, degrading, and ultimately extremely valuable lesson. It's especially difficult if you're naive because everyone around you is talking about metrics and OKRs, you agree on OKRs with people, a…
The best reason to work at a startup is if you are a founder and have significant equity. The other reasons to join are if you are enamored with a technology that they specifically use or want to get experience quickly wearing a lot of hats. There are no other reasons to work at a startup. You will work much harder, for less money, and poor benefits relative to larger companies. You work in uncertainty. Unless you ar…
I don't mean to suggest that startups don't have politics. They certainly do. But startup politics is different from megacorp politics, in ways that I can't really explain. All I know is that I feel much better at startups, even when there's a lot of politics flying around, than I do at megacorps, having worked at both.