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 :)
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.
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.
Is more more useful than having a longer runway from big co savings?
Doubtful.
Most of the lessons you learn are either going to be
1. General startup lessons (This information is available in YC Startup School, lean startup, etc...)
2. Lessons specific to the problem you're trying to solve (Whats the best way to reach rural RV buyers, what keeps people from renting a room for a night)
Working at a startup will teach you a little of 1, and none of 2.
So I'd easily trade the knowledge gained during two years of working at previous startup for 2 extra months of working on my startup.
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.
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 :)
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.
+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.
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.
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.
>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.
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.
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.
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.
>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.
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.
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.
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.
Just go to point X directly. Too many people shy away from their dreams and delay, because they want to learn first, practice first, and get ready before the real adventure. You will never deplete "more things to learn". You are only depleting your lifetime. And no matter how close working at a startup is to working on a startup, it will never be as close to it as itself.
If you need to save up some money or take care of any other blockers first for your own safety, fine. If there is a great company working on a great problem that you are excited by, great. But if you want to start a new company, then working at a startup is not a practice for starting a new startup. It is a practice for working at a startup and a practice for wasting another day of your life not living the way you really want to live.
The reality requires balance. For example, in university courses, prerequisites are required and enforced for good reason.
People try all the time to learn calculus with a weak foundation in precalculus, and they really struggle unnecessary. People also try to learn physics with a weak foundation in mathematics, with similar results. I would argue that the same is true for software development. You can develop bad habits (e.g. not using a style guide at all) by not doing initial prep work first first.
I agree that some people put things off indefinitely and end up in "tutorial hell," and for them it's better to err to going right to doing. But it's not always the case, and sometimes educational opportunities (e.g. getting work experience before starting a company) can really increase your skills.
> I would argue that the same is true for software development.
One can learn best practices without having to work at a startup / tech shop / MANGA. Besides, software development isn't the only skill required, there's likely a lot to learn but not enough time. With most upstarts, timing is more crucial than most other learnable factors, because you can never rollback time.
I wish I had had that opportunity back in 1985 when I founded my first one, but being outside of the Bay Area (as in 1500 miles away) there were basically no software startups at all, and with no internet/web/ycombinator etc, no way to learn anything except by trying and failing. We did ship our product, do marketing, make some sales but not enough so we had to sell the product and close down. Today I know all things I did wrong but back then you were working in a world unlike today, and not even one person to ask as everyone starting software companies back then was just as clueless unless you were in a few places in the country. It's hard to explain to people today just how hard this was (for example I tried to borrow some money at a local bank to buy computers, and when told we were a software company, the loan officer assumed we were making ladies undergarments).
Very cool. I think one doesn't need to join a startup for such experience nowadays. Simply joining YC/XYZ accelerator might help get a structure around the million things that are now institutional knowledge so you can focus on what matters.
A rather unique take on spreadsheets that would wind up influencing others to try experimentations on the spreadsheet idea, but all were ultimately killed by Excel, as what happened to us. Search "trapeze spreadsheet" on google if you care to know more.
My experience at a few startups does not align but I support the overall thesis.
More than one startup talked a big game in hiring about the product, the customers and the culture only to be more of a cult of personality where decisions were made in private between cofounders despite being an "open" company, unequal pay despite "transparent" salaries with bands, a lack of managerial skills or care for personnel management (once told not to bring my feelings to work) and in almost every single instance a technical founder or early engineer that cannot or will not share work by delegating.
The most important things I have learned have absolutely came from being involved with startups and 90% are what NOT to do.
The good thing is I identified what I love:
"Devops" and adding automation and structure to processes very early. Everyone thinks is has to get in the way or will slow them down. Slow is smooth and smooth is fast.
Building people is was more fun than building tech but you have to be on top of your hiring game early on. And you have to be willing to share and trust.
You have to ship. But that doesnt mean you dont invest in yourself. If you have money for 100 days then build for 100 days. If you have money for 2 years then build for 2 years. This means making that investment in your tools and your process.
Lastly, if you are B2B, buy a SOC2-in-a-box and get it over with and use something like auth0 or workos and just be ready with SSO integrations. Dont put off the foundational tablestakes of doing business with other tech companies.
Last suggestion deserves a caveat. Unless more than 5% of your revenue will unconditionally require SOC2, you should avoid doing it and accept the small revenue hit.
But you are correct, if you do need it, you should do it as early as you can and buy it out of the box as much as you can. I recommend Tugboat Logic for this.
For those that do not know, an audit is going to cost AT LEAST $20k but the total cost could be more than $50k (certainly more if you are paying market rate and you account for the team's time to pull everything together). And the requirements can cause side effect costs (penetration tests, etc).
Founder here. Seen plenty of people who “want to start a startup” come through the doors over 10 years.
To my knowledge, only 1 ever took the plunge, the rest all moved on to different jobs when they finished up with us. In every case they told me that an advantage of the new place is that they’d learn some more things they need to know for when they start their own thing.
To be clear I don’t judge their choices at all. Just pointing out that this is a pretty common thing people tell themselves.
By contrast the former employees who have gone on to do their own startup expressed no interest in the topic until one day they were suddenly a founder.
This seems about right. Startup ideas are the white collar equivalent of day dreaming about how you would spend the money if you won the lottery. It's cheap to talk about, easy to fantasize about, and many people have a very distorted perception of what skills are necessary to be an effective tech founder so (in their minds) their technical proficiency makes it plausible.
I am in the same boat as an employee who left a cushy job at G to join a startup with the motivation to start my company, but I feel there's a limit to "preparation" and one needs to be honest and take the plunge. Else, I am bs-ing myself.
I would have been in this camp, except I would not have said the next role would be stepping-stone to founderdom.
The main thing I learned is that I never, ever, EVER, want to start my own company, and actually never want to work in a company with fewer than 30 people again. Maybe seeing the stress and the actual type of work that makes up the work of an early stage founder (or indeed employee) is quite off-putting for people. I don't see that as a bad thing either.
I think a lot of people are allured by the idea of starting a startup and it shows in your numbers.
Where as "natural" founders are allured by "an idea" and decide the best way to push forward on this idea will be through startup org(in terms of freedom, financing => obtaining more people, interfacing with users of the idea etc).
Follow a top CEO/CTO as person 2-10 with a market you like...
... And then:
* Learn how 0->1 , product market fit, and overall process works, which you miss by joining growth-stage
* Grow from working with customers hands-on to becoming an area owner with responsibility around customer journey, revenue, hiring & firing, etc. VP Sales, early CTO/Dir of Engineering, CTO where you are heavy on sales/solutions engineering flow in big enterprises, ... . Working for a VP/director/manager is different from owning a part of the business, especially where you have a teneous & sales-oriented external aspect like revenue or customer success. Likewise, not owning the customer journey hides a lot, which is easy to miss in a growing company as specialization happens fast, esp in engineering.
* Pick carefully on enterprise vs consumer, which market within that, and which internal teams you work with. That's the customer persona you need to live & breathe later.
Not easy!
Also, fwiw, there is a big class of professional startup people who are 'scale up' experts that can take a working product, VC capital raised by other people, and help that grow faster. The OP's advice is more for getting on that track. And from a founders perspective: you can just hire them, everyone wins. Just don't confuse that with a 0->1 skillset, not inherent..
> If you can’t hire exceptional people then you shouldn’t expect exceptional outcomes: e.g, the outcomes most VCs expect.
BS. Exceptional people are mostly an illusion - yes, there are (for example) Linus Torvalds and Fabrice Bellard, but there are much less such people than startups, orders of magnitudes less. Exceptionalism comes from the combination of the idea quality, low level of mistakes in execution, some luck in the market, some combination of qualities, like perseverance, which smoothes out some problems - and other qualities like that, engineering level is certainly important but you can have exceptional results with just competent engineering. It's hard to find an example of textbook successful startups where engineering was outstanding. Sorry, won't give examples, just look for yourselves.
Yep, perhaps I should have said if you can't create an exceptional environment – of which team, culture and mission are all parts – then you can't expect exceptional outcomes.
Hiring people who have experience in those environments before can help you replicate that success again, though. So worth picking them, if you have a choice.
> I believe if you want the best chance of succeeding as a founder, first join an existing high-growth start-up where you can learn what good looks like, before you start something yourself.
We're all entitled to our beliefs, but this seems very specific to me. Why doe sit have to be "high-growth"? What if your startup isn't meant to be "high-growth"? Why do you specifically have to work at a startup? I believe getting some work experience is a good idea, mostly just because if you want to put other people's livelihood in your hands, one should probably mature a bit.
Additionally, this advice falls into the classic trap of "I did this, and therefore I think everyone else should". The advice could be true, or it could not, there is no way of knowing, so at the end of the day, the value of such advice is pretty low, IMO.
Specifically, high growth is useful because you can spend a few years there and get experience of doing many things at several different company sizes.
It means you get several opportunities to learn how to do a specific thing, and see how different attempts yield different results. At a company that grows more slowly you'll need to revisit things less frequently, which reduces your opportunity to learn.
You're right though, I don't have experience doing things other than what I've done. I can only speak to how useful my experience has been when going back to very early stage as a first employee, which has a lot of overlap with founder.
And in that sense, I'm continually thankful I have the experience I do in my current position. I think it means I'm materially more impactful, and I can only imagine performing significantly worse without it.
> You're right though, I don't have experience doing things other than what I've done. I can only speak to how useful my experience has been when going back to very early stage as a first employee, which has a lot of overlap with founder.
I think you're missing the critique: you don't know how useful your experience has been just because you experienced it. This is why systematic studies are necessary: to collate a lot of experiences to see what works and what doesn't (and even those are hard).
The needs of a startup are quite different than (and often conflicting or opposite to) the needs of a stable, large company. So if you have learned "what good looks like" elsewhere and have no first-hand experience in a high-growth environment, then you as a founder may be prone to decisions that are a poor fit in the context of a startup, which by definition is a high-growth. Launching an "ordinary" (i.e. non-high-growth) new business in an established niche will have much more overlap with previous work experience at some corporation than trying to get product-market fit for a startup.
Let's take it as a given that the needs of a startup are different from a stable, large company. That doesn't mean working at a startup is the best way to learn how to make your own startup. You could work at a company that is seriously dysfunctional and learn things you shouldn't. You could work at a company that just fell into amazing success and not learn anything that applies to the startup you'll make.
Because startup companies are by definition high-growth. The term has become significantly overused by clueless journalists and business types looking to pad their resumes with buzzwords.
Readit News
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 :)
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.
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.
Is more more useful than having a longer runway from big co savings? Doubtful.
Most of the lessons you learn are either going to be
1. General startup lessons (This information is available in YC Startup School, lean startup, etc...)
2. Lessons specific to the problem you're trying to solve (Whats the best way to reach rural RV buyers, what keeps people from renting a room for a night)
Working at a startup will teach you a little of 1, and none of 2. So I'd easily trade the knowledge gained during two years of working at previous startup for 2 extra months of working on my startup.
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.
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 :)
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.
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.
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.
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.
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.
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.
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.
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.
Great place to learn a thing or two, if you have the necessary background and experience.
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.
Just go to point X directly. Too many people shy away from their dreams and delay, because they want to learn first, practice first, and get ready before the real adventure. You will never deplete "more things to learn". You are only depleting your lifetime. And no matter how close working at a startup is to working on a startup, it will never be as close to it as itself.
If you need to save up some money or take care of any other blockers first for your own safety, fine. If there is a great company working on a great problem that you are excited by, great. But if you want to start a new company, then working at a startup is not a practice for starting a new startup. It is a practice for working at a startup and a practice for wasting another day of your life not living the way you really want to live.
People try all the time to learn calculus with a weak foundation in precalculus, and they really struggle unnecessary. People also try to learn physics with a weak foundation in mathematics, with similar results. I would argue that the same is true for software development. You can develop bad habits (e.g. not using a style guide at all) by not doing initial prep work first first.
I agree that some people put things off indefinitely and end up in "tutorial hell," and for them it's better to err to going right to doing. But it's not always the case, and sometimes educational opportunities (e.g. getting work experience before starting a company) can really increase your skills.
Agreed.
> ...university courses, prerequisites are required and enforced for good reason.
Perhaps, but see also this article and discussion: https://news.ycombinator.com/item?id=32497780
> I would argue that the same is true for software development.
One can learn best practices without having to work at a startup / tech shop / MANGA. Besides, software development isn't the only skill required, there's likely a lot to learn but not enough time. With most upstarts, timing is more crucial than most other learnable factors, because you can never rollback time.
And if you fail, you already worked at a startup (by founding it)
More than one startup talked a big game in hiring about the product, the customers and the culture only to be more of a cult of personality where decisions were made in private between cofounders despite being an "open" company, unequal pay despite "transparent" salaries with bands, a lack of managerial skills or care for personnel management (once told not to bring my feelings to work) and in almost every single instance a technical founder or early engineer that cannot or will not share work by delegating.
The most important things I have learned have absolutely came from being involved with startups and 90% are what NOT to do.
The good thing is I identified what I love:
"Devops" and adding automation and structure to processes very early. Everyone thinks is has to get in the way or will slow them down. Slow is smooth and smooth is fast.
Building people is was more fun than building tech but you have to be on top of your hiring game early on. And you have to be willing to share and trust.
You have to ship. But that doesnt mean you dont invest in yourself. If you have money for 100 days then build for 100 days. If you have money for 2 years then build for 2 years. This means making that investment in your tools and your process.
Lastly, if you are B2B, buy a SOC2-in-a-box and get it over with and use something like auth0 or workos and just be ready with SSO integrations. Dont put off the foundational tablestakes of doing business with other tech companies.
But you are correct, if you do need it, you should do it as early as you can and buy it out of the box as much as you can. I recommend Tugboat Logic for this.
For those that do not know, an audit is going to cost AT LEAST $20k but the total cost could be more than $50k (certainly more if you are paying market rate and you account for the team's time to pull everything together). And the requirements can cause side effect costs (penetration tests, etc).
To my knowledge, only 1 ever took the plunge, the rest all moved on to different jobs when they finished up with us. In every case they told me that an advantage of the new place is that they’d learn some more things they need to know for when they start their own thing.
To be clear I don’t judge their choices at all. Just pointing out that this is a pretty common thing people tell themselves.
By contrast the former employees who have gone on to do their own startup expressed no interest in the topic until one day they were suddenly a founder.
The main thing I learned is that I never, ever, EVER, want to start my own company, and actually never want to work in a company with fewer than 30 people again. Maybe seeing the stress and the actual type of work that makes up the work of an early stage founder (or indeed employee) is quite off-putting for people. I don't see that as a bad thing either.
Follow a top CEO/CTO as person 2-10 with a market you like...
... And then:
* Learn how 0->1 , product market fit, and overall process works, which you miss by joining growth-stage
* Grow from working with customers hands-on to becoming an area owner with responsibility around customer journey, revenue, hiring & firing, etc. VP Sales, early CTO/Dir of Engineering, CTO where you are heavy on sales/solutions engineering flow in big enterprises, ... . Working for a VP/director/manager is different from owning a part of the business, especially where you have a teneous & sales-oriented external aspect like revenue or customer success. Likewise, not owning the customer journey hides a lot, which is easy to miss in a growing company as specialization happens fast, esp in engineering.
* Pick carefully on enterprise vs consumer, which market within that, and which internal teams you work with. That's the customer persona you need to live & breathe later.
Not easy!
Also, fwiw, there is a big class of professional startup people who are 'scale up' experts that can take a working product, VC capital raised by other people, and help that grow faster. The OP's advice is more for getting on that track. And from a founders perspective: you can just hire them, everyone wins. Just don't confuse that with a 0->1 skillset, not inherent..
BS. Exceptional people are mostly an illusion - yes, there are (for example) Linus Torvalds and Fabrice Bellard, but there are much less such people than startups, orders of magnitudes less. Exceptionalism comes from the combination of the idea quality, low level of mistakes in execution, some luck in the market, some combination of qualities, like perseverance, which smoothes out some problems - and other qualities like that, engineering level is certainly important but you can have exceptional results with just competent engineering. It's hard to find an example of textbook successful startups where engineering was outstanding. Sorry, won't give examples, just look for yourselves.
Hiring people who have experience in those environments before can help you replicate that success again, though. So worth picking them, if you have a choice.
We're all entitled to our beliefs, but this seems very specific to me. Why doe sit have to be "high-growth"? What if your startup isn't meant to be "high-growth"? Why do you specifically have to work at a startup? I believe getting some work experience is a good idea, mostly just because if you want to put other people's livelihood in your hands, one should probably mature a bit.
Additionally, this advice falls into the classic trap of "I did this, and therefore I think everyone else should". The advice could be true, or it could not, there is no way of knowing, so at the end of the day, the value of such advice is pretty low, IMO.
It means you get several opportunities to learn how to do a specific thing, and see how different attempts yield different results. At a company that grows more slowly you'll need to revisit things less frequently, which reduces your opportunity to learn.
You're right though, I don't have experience doing things other than what I've done. I can only speak to how useful my experience has been when going back to very early stage as a first employee, which has a lot of overlap with founder.
And in that sense, I'm continually thankful I have the experience I do in my current position. I think it means I'm materially more impactful, and I can only imagine performing significantly worse without it.
I think you're missing the critique: you don't know how useful your experience has been just because you experienced it. This is why systematic studies are necessary: to collate a lot of experiences to see what works and what doesn't (and even those are hard).