Brutally honest moment: startups kind of suck.
I find "startup culture" to be counter-productive. The ping pong tables, people writing on the windows, the "tee shirt and sport coat look", constant focus on capital and branding instead of sales, it's not impressive.
Most are run by people who have no idea what they're doing - and that's fine, everyone has to start somewhere, but it's not a ride I want to take with you.
The failure rate is about 90%, so job security is out no matter what kind of expertise you bring.
Of the 10% that do survive, they fall into three categories: acquisitions, sustainable businesses, and "perpetual startups".
Acquisitions are hit or miss. Sometimes the old team stays, sometimes they go. On some rare occasions your equity is worth something when the company is acquired, but if you're a 10% or less owner and the company is acquired for $2 million, you'll be starting over and looking for a job again in a year.
Sustainable businesses are great if there's an upside - that's what you hope for at least. If the company never goes public and there is no market for your equity though, you're stuck at your salary.
And then there's what I call "perpetual startup mode" - where the company isn't an acquisition target and is never really profitable, but raised or continues to raise enough initial capital to keep the lights on. These are the worst, because you always feel like you're on the edge of something big but just can't get over the hump. Very disheartening, and you waste years of your life where you don't move forward.
Call me old and crazy, but I prefer the traditional corporate setting and working with people who are seasoned experts in proven market sectors. I like having a virtually unlimited marketing budget to test new ideas and have enough data and audience that the results are statistically significant. I like leaving work at the office and not being expected to answer the phone or respond to emails. I like flying business class and staying in nice hotels for work-related travel, and not feeling like I should be cutting back because it's "not good for the company to spend money on stuff like this". I want stock options in a company that's already public and has liquidity, so I know it will be worth something if I feel like cashing out.
Perhaps most importantly, if I get bored with what I'm doing and decide to move on to something else, I want my next employer to not only have heard of my last employer, but be able to talk about my work experience and goal achievement in a measurable way - you can't do that if the company isn't profitable, isn't there anymore, or pivoted 100 times before finally deciding what they wanted to be when they grew up.
Working for a startup is a gamble that rarely pays off. If I was still 20 maybe I'd still find that interesting, but I've watched too many people jump from company to company to ever be comfortable doing it myself. Someone would have to offer some meaningful upfront cash to even consider it again.
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