This is mostly accurate but it misses one essential point. And so do many of the responses here. One of the reasons to work at a startup is to get a lot of responsibility for something interesting to you, the sort of thing that wouldn't come your way outside of a startup, for a long time, or maybe ever. The point in the article that comes closest to identifying this regards "calling", but that's not the same thing.
I am 64, and worked in many startups, from 1988 through 2013. My main criteria for evaulating a startup were interesting work, and potential financial reward. I would also try to avoid companies whose business model didn't make sense to me. This worked out pretty well. I started out on an academic path, went to an industrial research lab in the 80s, and this led me to the startup world, where some ideas in software research were used as the basis of innovative products. I wasn't comfortable as a pure academic, and I loved writing software, so this was the right path for me.
At each new company, my thought was: if the business fails, at least I've had fun and worked on interesting software. And this often worked out very well:
- Startup 1: The company was building an innovative product, really a new category of software. I was given responsibility for one huge part of it, and this was my first job ever in which I was being paid to create software (as opposed to research). The company had a modest IPO. Nice payout. In my last couple of years, I started a new project which was rejected by the company. But this led to ...
- Startup 2: I took a summer off, built software based on my ideas, and merged with a startup that had complementary ideas. We needed each other. So much fun. This company was acquired toward the end of the dotcom bubble. Nice payout.
- Startup 3: Post bubble explosion, my choices were a consumer startup or interesting tech at a non-startup. I chose the consumer startup. Pretty dull, although fascinating from a sociological point of view. I left when I got bored and tech startups were happening again. Minor payout a few years later when they were acquired.
- Startup 4: My favorite. Fascinating project, three key pieces, I built one of them. I also really enjoyed building the tools to support the development and troubleshooting work. Acquired by a huge company. Nice payout.
- Startup 5: Really interesting idea. I loved the idea so much that I missed the fact it should have been a feature of a product, not a product by itself. Oops.
Startup 1: joined as the first employee pretty much straight out of school. Talked to potential customers, worked on the product and overall learned lot about startups. Modest low exit some years after I left. No payout. (Europe, so not common to have equity back in the day).
Startup 2: joined the founding team of a gaming startup. The company flopped. Built and learned a lot.
Startup 3: started my own company, moved to US, raised funding etc. Learned a lot, we had to shut it down after couple of years as failed to grow the business and didn't see a way to pivot. Returned remaining funds to the investors.
Startup 4: joined another startup. One of the first 20 employees. Build a lot, learned lot. Exercised the stock when I left. The company IPOd 6 years later. $50M payout. I had early exercised some stock so some of it was federally tax free under QSBS.
Startup 5: Joined pre-IPO FAANG, got a decent salary. Learned a lot of about politics and presenting to execs. Honed my own craft and skills on the company time. $3M payout from RSU which more than half went to taxes as ordinary income.
Anyway, been lucky with two of my last companies, but I would say the earlier startups gave me skills and confidence to operate in the level I needed.
I think FAANG is nice place to make $1-2M over some years but it’s unlikely to make $10M or more.
In all my jobs there were some crunch times every now and them, but I never worked 100 hours or over the weekend consistently. After being a founder I did realize that you don’t have to work that hard for other companies.
Startup outcomes are uncertain but you can definitely affect them by choosing the right companies. If anything else, you will learn a lot likely. Time moves faster in startups, so few years in a startup might be like 5 years at FAANG, and you actually learn to build things instead of sit in meetings.
Why did you join #5? You were already independently wealthy, was the position that much fun? (My secret fear: once one has enough money, is there really nothing better to do than get another job?)
I'd like to know the answer to this as well. I'm not sure what I would do if I were to become financially independent before "retirement age", but it certainly wouldn't be getting a job at a BigCo. Really curious to hear the motivations behind it.
I probably could have skipped my 5th startup, but psychologically, I couldn't see myself as retired. Startup #4 was, for a time, the most stressful job I've ever had. My part was distributed, and I was dealing with all the gotchas that entails, and these gotchas were being uncovered at a high rate, thanks to a stellar system testing guy.
And then, suddenly, the last serious distribution bug was solved, and the system was working, rock solid. And I glided, through the acquisition, and then for a couple of years with our new corporate parent. Interesting new development stopped, and it was all about maintaining a working system. They knew they couldn't keep people there with interesting work, so they threw money at us. And it worked for a lot of people. Me too, for a while, until startup #5 came along, and it was really interesting. So I left.
But #5 was poorly conceived, and had other difficulties, and it burned me out after a few years. A really deep burnout -- I was angry all the time, and couldn't get myself to focus on work. I figured that 25 years of startups was enough, I was able to retire, so I did.
I do sometimes struggle to keep myself occupied. I've done a couple of minor software projects, but it is difficult to motivate myself to do something that has already been done, and that nobody really needs. I have also found it difficult to motivate myself to get into new (to me) areas, e.g. machine learning. There is some amount of depression going on, for sure.
I did consider going back to BigCo, but: I really enjoy having the freedom to travel where and when I want, the lack of stress, and all the other obvious benefits of not working. But the major reason is this: If I am bored and don't know how to fill my time, that is a fundamental problem. Doing some random task for BigCo doesn't fix that problem, it masks it. I need to figure out what it is I want to do.
I did find one fun project: I decided that I really needed something that didn't involve sitting in front of a keyboard. So I decided to build a sailboat. Having no experience with woodworking, I opted for a kit that includes pre-cut wooden pieces, and it's up to me to glue, and sand, and varnish, and paint. Sort of like building a model, like when I was a kid, but on a bigger scale. Surprisingly difficult, for me at least.
Worth noting that this is an exceptional track record - 4 of 5 startups with a paying acquisition. Great story, but it’s not likely the normal result of doing 5 startups :)
It's a nice comment with an interesting point of view, but the "range of experience" is somewhat limited by the fact that their first four startup experiences ended in four "nice payouts", which is an amazing and atypical track record.
I am 64, and worked in many startups, from 1988 through 2013. My main criteria for evaulating a startup were interesting work, and potential financial reward. I would also try to avoid companies whose business model didn't make sense to me. This worked out pretty well. I started out on an academic path, went to an industrial research lab in the 80s, and this led me to the startup world, where some ideas in software research were used as the basis of innovative products. I wasn't comfortable as a pure academic, and I loved writing software, so this was the right path for me.
At each new company, my thought was: if the business fails, at least I've had fun and worked on interesting software. And this often worked out very well:
- Startup 1: The company was building an innovative product, really a new category of software. I was given responsibility for one huge part of it, and this was my first job ever in which I was being paid to create software (as opposed to research). The company had a modest IPO. Nice payout. In my last couple of years, I started a new project which was rejected by the company. But this led to ...
- Startup 2: I took a summer off, built software based on my ideas, and merged with a startup that had complementary ideas. We needed each other. So much fun. This company was acquired toward the end of the dotcom bubble. Nice payout.
- Startup 3: Post bubble explosion, my choices were a consumer startup or interesting tech at a non-startup. I chose the consumer startup. Pretty dull, although fascinating from a sociological point of view. I left when I got bored and tech startups were happening again. Minor payout a few years later when they were acquired.
- Startup 4: My favorite. Fascinating project, three key pieces, I built one of them. I also really enjoyed building the tools to support the development and troubleshooting work. Acquired by a huge company. Nice payout.
- Startup 5: Really interesting idea. I loved the idea so much that I missed the fact it should have been a feature of a product, not a product by itself. Oops.