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I've worked at multiple startups sub 50 to >1000 (unicorn status) and have founded and sold my own company. I've also worked at a few of the FAANGs. This is com

I've worked at multiple startups sub 50 to >1000 (unicorn status) and have founded and sold my own company. I've also worked at a few of the FAANGs. This is common advice, especially among VCs since it's one of the key benefits used to pitch prospective employees on giving up that fat FAANG salary, but in my personal experience, it's not so cut and dry. Working in a startup will brand you as a startup person and help you meet VCs which may make it easier to raise. It'll also show you the problems that that particular startup faces and give you n=1 degree of pattern matching. On the flip side, something like YC can give you the same benefit or just shipping a for-profit side project on the side. Additionally, given how poorly run most startups are today, I'd posit that you're actually in more danger of learning the wrong lessons than the right lessons by joining a startup. At the end of the day, the truth is likely to be Peter Thiel's observation that joining the right, highly successful, high growth startup as a very early employee is a great way to learn exactly 1 method of starting a successful company--the way that company did it. But if the startup you join isn't that rocketship, you've only learned how to (or how not to) achieve that particular path of failure or mediocrity. Not particularly great advice though, because then the challenge becomes identify those startups. And if you could do that reliably, I'd suggest you switch careers into VC instead :)

lawrjone 4y ago
I'm not sure I agree with the comparison of picking a start-up to join being the same as one you might invest in. At least, in terms of this article, a start-up that has growth ambitions and has just raised a round is a great bet. Unlike a potential investor, you didn't need to get in before that round to make the investment worthwhile, and in a sense you don't care as much about the company itself being an outsized success: not if your primary goal is around learning, which I think is legitimate, especially early in your career. Similarly, I suspect it's not quite right to assume lessons in one start-up don't apply to others. In London at least, there's a strong network of people across the start-up scene who talk a lot. Many of those start-ups have very similar cultures and ways of working, similar enough that they hit the same problems and lessons learned it one often translate to others. My intention, writing this article, was to encourage people to view joining a start-up with momentum as a valuable learning experience before they start their own thing, possibly more valuable than a big corporation or just jumping into start-ups themselves. I think finding companies that can provide you with that growth isn't too hard, and I'd be happy to help anyone who wanted to find them, if they wanted it :)
- jchonphoenix 4y ago
  The point is that the valuable lessons and growth on how to effectively build a successful startup only occurs at those high success high growth companies. I've been at successes and failures. You learn much more from success.
muse900 4y ago
I agree with plenty of what you are saying, at the same time I believe that joining problematic start-ups or failing start-ups can teach you plenty on how not do things. Remember that before succeeding you have to fail and improve in a cycle of n times until you succeed. If you succeed without failing then there is a high probability of luck being involved.
hef19898 4y ago
I see that in real life at the moment, the part about the badly run start-up. With some experience, it is easy to spot the mistakes. Most employees are too young / unexperienced so realize it. Heck, half of the middle management is still at their first jobs out of university. And man, it shows. Nowhere near FAANG in terms or organisation or best practices. Great place to learn a thing or two, if you have the necessary background and experience.
xivzgrev 4y ago
I agree. I joined a few smaller startups and saw plenty about how NOT to do things. Only one I joined a larger company did I feel happier (in hindsight). And now if I went back to a startup, I’d feel more confident about whether the company is run poorly and how much I can help it. Some problems are organizational immaturity and can be fixed. Some problems come from leadership and won’t change as long as those leaders are there.
baby 4y ago
There really are millions of lessons to be learned though, not just the “how to be successful”. If all you did was working at a big corp or at a FAANG you will run into tons of issues which you will have to deal with at the same time as founder-related issues.
ren_engineer 4y ago
>Additionally, given how poorly run most startups are today, I'd posit that you're actually in more danger of learning the wrong lessons than the right lessons by joining a startup this can be more valuable in many ways, I've literally taken notes about things NOT to do when it comes to things like meetings, processes, etc.
- bick_nyers 4y ago
  Exactly, you get to see how early (or late) decisions have scaled up, for better or for worse. You have to take an intelligent approach though, you can't just go in the opposite direction, e.g. excess meetings can be very damaging to engineers, so let's do 0 meetings.
- ZephyrBlu 4y ago
  Learning what not to do is not an effective use of time.
qqqwerty 4y ago
There is way more than one lesson to learn from each startup. You will hopefully learn how to hire (and possibly fire) people. You will get insight into the nitty gritty of keeping the lights on at a company (taxes, payroll, office leases, etc...), and you will get familiar with the typical fundraising cycle. Most people don't appreciate how fast 18 months to two years of funding can run out. Going through that stuff once or twice when you don't have the pressure of being the founder can be very beneficial. And while going through an accelerator can be a substitute, I can't imagine that encountering a lot of this stuff for the first time while trying to start your first company would be anything less then very stressful. For most employees, the best deal for them financially is to go the FAANG route. But I absolutely recommend working at a startup if you are hoping to one day start your own. It should be said that most startup employees are not going to start their own company (even ones who think they will). So certainly keep that in mind. But I suppose another benefit is working at a startup is probably a good way to gauge if starting a startup is something you could handle. After having worked at one for a while, I have certainly come to more realistic understanding of what kind of startup I would be comfortable founding. I almost certainly would prefer to bootstrap a small project rather than go the VC route, but I think I would feel pretty comfortable taking VC money if the opportunity called for it. But I have also come to realize that the best fit for me in my next role is probably not as a founder, but most likely as a very early employee of another startup. But this time around I will have a much better idea of what to look for in the founding team.
- ido 4y ago
  I've worked at multiple startups before starting my own, some were more useful than others. In my experience only in lead or above positions do you actually get exposure to these things - a random IC doesn't really get much insight into the company's finances, raising, negotiations, hiring, etc. From those I was a lead at I got some valuable experience (including what not to do) & also contacts (some former director/C-level people I'm still in touch with). I still learned the vast majority from actually having to handle it myself in my own startup but I think I would have learned even less (in that particular area) if I was working at amazon or google before instead.
  - 4y ago
jchonphoenix 4y ago
I agree you can learn many lessons about what not to do. The broader point I'm making here is that there's a billion things not to do and a few things you should do. The successful startups will also make mistakes, iterate, and teach you the things not to do but teach you how to figure out what you should be doing. The unsuccessful ones just stubbornly plod forward and you, the employee, just know you guys screwed it up, but have no idea how to find success. TL;DR YMMV, but it's much more valuable to learn a selection of "winning moves" you can apply than it is to learn a bunch of "losing moves" not to apply.
jatins 4y ago
+1 Don't think this working for a startup offers much advantage for an engineer if they later decide to work on their own. If you already know programming, there isn't a lot of value add that couple years of startup experience offers in terms of your programming skills. The skills that you don't have -- Sales, marketing, hiring -- you will still not have. Working for a startup, as say, a frontend engineer for couple years does not help you get better at Sales. You'll need to hire for them or rely on co-founders anyway. The "wearing multiple hats" trope is extremely over hyped in my experience.
aledalgrande 4y ago
Agree with the "what not to do" not being valuable (and that's most startups). You can read that in HN comments every day. Sure you can learn "I must not do X or my devs will feel shitty and leave", but what is the answer to "how can I keep my top performers happy and growing so they don't leave and instead make the company a rocketship?" What I really want to know is how to make a buddying startup a high growth startup. And only a tiny amount of companies can give you that, and only if you are working in leadership roles.
Ken_At_EM 4y ago
Anti know-how can be a pretty good teacher as well. 18 months at a terribly run startup showed me all things not to do when I started my own.
onemiketwelve 4y ago
I disagree, my very first job was at a startup in lieu of a big company. I think I was very naive at the time and thought I knew how things worked coming out of business school. I learned tons of what not to do and saw what I thought were pretty big mistakes like not having tests, not talking to customers and actively saying no to user requests. And despite all this, the company was still afloat and was still growing. It gave me a lot of hope tbh that you can make several mistakes and still have a decent shot. And I learned tons of what to do correctly. I saw what "rockstar" engineers were actually. I drank from a firehose from a tech standpoint.
As_You_Wish 4y ago
>Not particularly great advice though, because then the challenge becomes identify those startups. Only 1 out of 100 companies, if that, VCs invest in don't go out of business. Even with their ton of experience, their smart people, and all kinds of opportunities that you don't have, it's little more than guesswork on their side. Trying to look for what is going to be a successful startup is a fool's errand. Pure luck.
Willish42 4y ago
This is much more well-put than I'd have managed to write. Had a couple years of startup experience and I feel like the instability and "wrong lessons" were too much for me personally. IMO a lot of people conflate working in a startup with the experience of being a more senior engineer becoming a founder or early employee with similar levels of autonomy. I worked in roles during my first ~5 years where I was the 4th or 5th engineer and was basically given narrowly-defined tasks to complete, with no great guidance on accomplishing them, and with my coworkers too busy to document or explain how to do basic things like run parts of the codebase locally, connect to the db, etc. You can get a lot better mentorship in those more "boring" traditional jobs at larger companies. You can get that in a startup environment too, but depending on the startup the degree to which that's actually something people prioritize and have capacity for varies wildly. I guess I'd recommend trying smaller startup environments if you happen to already know everything about their tech stack and/or have a decent amount of experience as a SWE already. Both are probably useful but I've personally gotten a lot better ROI growth-wise when working on an established team with stable goals, time to mentor, document, write tests, etc.

lawrjone 4y ago

I'm not sure I agree with the comparison of picking a start-up to join being the same as one you might invest in. At least, in terms of this article, a start-up that has growth ambitions and has just raised a round is a great bet. Unlike a potential investor, you didn't need to get in before that round to make the investment worthwhile, and in a sense you don't care as much about the company itself being an outsized success: not if your primary goal is around learning, which I think is legitimate, especially early in your career. Similarly, I suspect it's not quite right to assume lessons in one start-up don't apply to others. In London at least, there's a strong network of people across the start-up scene who talk a lot. Many of those start-ups have very similar cultures and ways of working, similar enough that they hit the same problems and lessons learned it one often translate to others. My intention, writing this article, was to encourage people to view joining a start-up with momentum as a valuable learning experience before they start their own thing, possibly more valuable than a big corporation or just jumping into start-ups themselves. I think finding companies that can provide you with that growth isn't too hard, and I'd be happy to help anyone who wanted to find them, if they wanted it :)

jchonphoenix 4y ago
The point is that the valuable lessons and growth on how to effectively build a successful startup only occurs at those high success high growth companies. I've been at successes and failures. You learn much more from success.

muse900 4y ago

I agree with plenty of what you are saying, at the same time I believe that joining problematic start-ups or failing start-ups can teach you plenty on how not do things. Remember that before succeeding you have to fail and improve in a cycle of n times until you succeed. If you succeed without failing then there is a high probability of luck being involved.

hef19898 4y ago

I see that in real life at the moment, the part about the badly run start-up. With some experience, it is easy to spot the mistakes. Most employees are too young / unexperienced so realize it. Heck, half of the middle management is still at their first jobs out of university. And man, it shows. Nowhere near FAANG in terms or organisation or best practices. Great place to learn a thing or two, if you have the necessary background and experience.

xivzgrev 4y ago

I agree. I joined a few smaller startups and saw plenty about how NOT to do things. Only one I joined a larger company did I feel happier (in hindsight). And now if I went back to a startup, I’d feel more confident about whether the company is run poorly and how much I can help it. Some problems are organizational immaturity and can be fixed. Some problems come from leadership and won’t change as long as those leaders are there.

baby 4y ago

There really are millions of lessons to be learned though, not just the “how to be successful”. If all you did was working at a big corp or at a FAANG you will run into tons of issues which you will have to deal with at the same time as founder-related issues.

ren_engineer 4y ago

>Additionally, given how poorly run most startups are today, I'd posit that you're actually in more danger of learning the wrong lessons than the right lessons by joining a startup this can be more valuable in many ways, I've literally taken notes about things NOT to do when it comes to things like meetings, processes, etc.

bick_nyers 4y ago
Exactly, you get to see how early (or late) decisions have scaled up, for better or for worse. You have to take an intelligent approach though, you can't just go in the opposite direction, e.g. excess meetings can be very damaging to engineers, so let's do 0 meetings.
ZephyrBlu 4y ago
Learning what not to do is not an effective use of time.

qqqwerty 4y ago

There is way more than one lesson to learn from each startup. You will hopefully learn how to hire (and possibly fire) people. You will get insight into the nitty gritty of keeping the lights on at a company (taxes, payroll, office leases, etc...), and you will get familiar with the typical fundraising cycle. Most people don't appreciate how fast 18 months to two years of funding can run out. Going through that stuff once or twice when you don't have the pressure of being the founder can be very beneficial. And while going through an accelerator can be a substitute, I can't imagine that encountering a lot of this stuff for the first time while trying to start your first company would be anything less then very stressful. For most employees, the best deal for them financially is to go the FAANG route. But I absolutely recommend working at a startup if you are hoping to one day start your own. It should be said that most startup employees are not going to start their own company (even ones who think they will). So certainly keep that in mind. But I suppose another benefit is working at a startup is probably a good way to gauge if starting a startup is something you could handle. After having worked at one for a while, I have certainly come to more realistic understanding of what kind of startup I would be comfortable founding. I almost certainly would prefer to bootstrap a small project rather than go the VC route, but I think I would feel pretty comfortable taking VC money if the opportunity called for it. But I have also come to realize that the best fit for me in my next role is probably not as a founder, but most likely as a very early employee of another startup. But this time around I will have a much better idea of what to look for in the founding team.

ido 4y ago
I've worked at multiple startups before starting my own, some were more useful than others. In my experience only in lead or above positions do you actually get exposure to these things - a random IC doesn't really get much insight into the company's finances, raising, negotiations, hiring, etc. From those I was a lead at I got some valuable experience (including what not to do) & also contacts (some former director/C-level people I'm still in touch with). I still learned the vast majority from actually having to handle it myself in my own startup but I think I would have learned even less (in that particular area) if I was working at amazon or google before instead.
- 4y ago

jchonphoenix 4y ago

I agree you can learn many lessons about what not to do. The broader point I'm making here is that there's a billion things not to do and a few things you should do. The successful startups will also make mistakes, iterate, and teach you the things not to do but teach you how to figure out what you should be doing. The unsuccessful ones just stubbornly plod forward and you, the employee, just know you guys screwed it up, but have no idea how to find success. TL;DR YMMV, but it's much more valuable to learn a selection of "winning moves" you can apply than it is to learn a bunch of "losing moves" not to apply.

jatins 4y ago

+1 Don't think this working for a startup offers much advantage for an engineer if they later decide to work on their own. If you already know programming, there isn't a lot of value add that couple years of startup experience offers in terms of your programming skills. The skills that you don't have -- Sales, marketing, hiring -- you will still not have. Working for a startup, as say, a frontend engineer for couple years does not help you get better at Sales. You'll need to hire for them or rely on co-founders anyway. The "wearing multiple hats" trope is extremely over hyped in my experience.

aledalgrande 4y ago

Agree with the "what not to do" not being valuable (and that's most startups). You can read that in HN comments every day. Sure you can learn "I must not do X or my devs will feel shitty and leave", but what is the answer to "how can I keep my top performers happy and growing so they don't leave and instead make the company a rocketship?" What I really want to know is how to make a buddying startup a high growth startup. And only a tiny amount of companies can give you that, and only if you are working in leadership roles.

Ken_At_EM 4y ago

Anti know-how can be a pretty good teacher as well. 18 months at a terribly run startup showed me all things not to do when I started my own.

onemiketwelve 4y ago

I disagree, my very first job was at a startup in lieu of a big company. I think I was very naive at the time and thought I knew how things worked coming out of business school. I learned tons of what not to do and saw what I thought were pretty big mistakes like not having tests, not talking to customers and actively saying no to user requests. And despite all this, the company was still afloat and was still growing. It gave me a lot of hope tbh that you can make several mistakes and still have a decent shot. And I learned tons of what to do correctly. I saw what "rockstar" engineers were actually. I drank from a firehose from a tech standpoint.

As_You_Wish 4y ago

>Not particularly great advice though, because then the challenge becomes identify those startups. Only 1 out of 100 companies, if that, VCs invest in don't go out of business. Even with their ton of experience, their smart people, and all kinds of opportunities that you don't have, it's little more than guesswork on their side. Trying to look for what is going to be a successful startup is a fool's errand. Pure luck.

Willish42 4y ago

This is much more well-put than I'd have managed to write. Had a couple years of startup experience and I feel like the instability and "wrong lessons" were too much for me personally. IMO a lot of people conflate working in a startup with the experience of being a more senior engineer becoming a founder or early employee with similar levels of autonomy. I worked in roles during my first ~5 years where I was the 4th or 5th engineer and was basically given narrowly-defined tasks to complete, with no great guidance on accomplishing them, and with my coworkers too busy to document or explain how to do basic things like run parts of the codebase locally, connect to the db, etc. You can get a lot better mentorship in those more "boring" traditional jobs at larger companies. You can get that in a startup environment too, but depending on the startup the degree to which that's actually something people prioritize and have capacity for varies wildly. I guess I'd recommend trying smaller startup environments if you happen to already know everything about their tech stack and/or have a decent amount of experience as a SWE already. Both are probably useful but I've personally gotten a lot better ROI growth-wise when working on an established team with stable goals, time to mentor, document, write tests, etc.