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.
Fair enough. I am an IC, but also an early-ish employee. And the startup I currently work at might be anomalous in how much they share about the company. With that said, if you are joining a startup to get founder level experiences, you almost certainly have some agency in this matter (that is kinda the point of working at a startup after all, you get more input and higher level input than at BigCo.) Go out and talk to folks about what they are working on. Ask the founders to share details about the company, including board slides, financial details, and product initiatives. If they don't oblige, it probably makes sense to work somewhere else.
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.
> Is more more useful than having a longer runway from big co savings? Doubtful.
Having worked at a startup before, I now know to never risk a substantial amount of my own money on the venture. The risk of failure is too high. I would either a) go the side project->bootstrap route or b) have angel or accelerator money lined up, which should be easy because having worked at a startup before, my network now includes angel investors.
> This information is available in YC Startup School, lean startup, etc...
I have participated in Startup School. It certainly has some value, but it is in no way a substitute for working at a startup. Not even close. Also, your competitors have access to the same resources, so it is not exactly a competitive edge.
> Whats the best way to reach rural RV buyers, what keeps people from renting a room for a night
That is called marketing and market research. Almost every startup in existence does it. And if you work at a startup, you will get a close up look at how it is done, and you will get some valuable lessons on what to do and what not to do. And having worked at a startup, I now also have a list of potential freelancers in case I wanted to contract that work out.
What position were you in that you worked closely with the marketing team and the angel investors?
I was a dev, so I never interacted with either of those groups closely. And when I started my own startup our dev doesn't really interact with marketing and has never met our investors.
Engineer. Employee #7. Maybe as an addendum to my above comments, my startup is fairly open about all of our operations. Other than peoples salaries, pretty much everything about the company is discussed at our all hands. Additionally I just like to ask people what they are working on. It is a good conversation starter.
Maybe another lesson here, is if you are running a startup, consider oversharing with your employees. A fair number of them may be there because they are trying to figure out if the next step for them is founding a company. And oversharing is a good way to keep them engaged. I have been at my current startup for 6-7 years, and would definitely not have stuck around this long had I not felt like I was learning much.
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).
As an incident management tool, getting certified was a thing we knew we needed early.
Gotta hand it to Chris (one of our founders) who came from being Director of Platform at Monzo (a UK neobank) and had spent years battling auditors, and knew exactly how to play it.
Kinda hammers home the point of my article... but about three months into our company life, we were SOC 2 certified, and it didn't feel like much effort at all.
In case anyone is looking for actionable advice, we used Vanta to help us through the process. If you're funded, I think it's well worth the money.
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).
I think the content is still useful, though. Especially as it gives some examples of the type of challenge that appear routinely when scaling a company, and why experience seeing this before can help you avoid similar mistakes if you ever start your own thing.
I'd personally love to see people write competing posts from other angles, even if they too will be limited by the author's own experience.
It would be great to hear what type of stuff you can learn from working at a large corporation was particularly useful when starting a company. I'd read that in a heartbeat!
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.
I worked at early, fast growing startups and later founded and raised venture capital for my own startup. You'd think I'd agree with this article, but I actually don't, here's why:
1) Working at fairly successful startups gave me excuses to put off starting my own company because I was still "learning so much." In retrospect, I should have started my own company years earlier.
2) Identifying startups that will turn into rocketships is hard. If you are that good at identifying successful startups early on, you should probably consider becoming a VC. :)
Hmm I feel like most founders I know just started companies after college without much experience. While people that want to get experience first seem to never end up starting a company. I think it mostly comes down to risk adversity.
I am absolutely not saying you can't do this. In fact, GoCardless is an example of a company started by very young founders with little start-up experience, and is now a unicorn.
The difference is that if you have this experience when starting a company, it can help you avoid so many stumbling blocks, and you can skip forward to more mature company stages.
While you can't really compare two companies, I think it's interesting that the company I currently work at (incident.io) has only taken a year to go from me joining as the first employee to 40 people + series A + hundreds of customers now.
There's no way we'd have moved so fast if it wasn't a case of replicating what we already knew worked, tweaked for the environment we found ourselves in.
So yes, it doesn't mean you can't be successful as an inexperienced founder, but I do think it makes a difference in terms of execution.
I think this may just be your bubble - I'm 39 and worked as a programmer since I was 18 in 3 different cities/countries & I know lots of both experienced people and people out of college who started companies.
Is a "startup" the same as starting a company? If I start a company without ever seeking external funding/accelerating/etc, is my company a "startup" in the same way that "founding a startup" implies?
I was under the impression that starting a company in general and 'starting a startup' are not exactly the same thing, though I surely might be wrong about this.
I think the average US founder age is 40s. But I'm not sure since most statistics focus on successful founders. This link seems to look at all of them.
The average founder of a business is not founding a VC-targeted startup, or even a technology business. There are a lot more landscapers counted in all of these surveys of successful startup businesses than founders who even considered YC.
If you lack the confidence to start a startup then working at one can help you gain than to create one in the future. But I'm not confident it increases the chances the company is going to be successful.
Actually if you had the chance to work at a company that became a unicorn, you will have better chance to get founding which increase the chance that your company is going to work, so yeah.
Except for that confidence and founding part I'm not sure it is valuable
I'm first employee at a start-up now, and while not a founder, the experience I have from seeing this stuff in previous companies totally changes the game.
When we decide to do something, such as make key hires, build new teams or invest in infrastructure, we have way more confidence that we're doing it at the right time. And when we do it, it's 90% what we need, skipping so many of the painful intermediate stages I've seen before.
It makes a huge difference in velocity, which is key for successful start-ups. So while you're right about funding and network, you execute better too.
Yeah so what you explain is that you have more confidence about what your do, but that says nothing about the success rate of previous startup employee vs success rate of others
Yes, having experience in a domain can help you be more confident in your decisions. Are you trying to argue that experience plays no role in long term outcomes of building businesses?
I don’t think he’s arguing about the benefit of having confidence and experience in a domain, but rather the origin of the experience and confidence and how it impacts a startup’s success.
In this case: the startup success rate of those who worked for startups vs those who worked in some other institutions (or for some, no work at all).
Sure, working at a startup might make you be confident at making decisions, but will that confidence lead to good results when you’re a founder? Working at another place can give you confidence as well, but again, will it help you get the results you want in your startup?
Anyhow, I’m not sure the answers matter much because the author didn’t write much about the uniqueness of the skills learnt in startups. He emphasised more on velocity of learning skills that can be learnt in many places, but high-growth startups can provide the fastest route.
Another massive advantage is finding cofounders and employees from the pool of people you work with and meet.
I think that is the best way to find suitable people outside your specialty where you can properly judge people’s integrity, ability, and their match with you (working style, filling the holes in your skills, compatibility, boss vs employee).
I have done this, no I have seen other successful entrepreneurs do it.
But aren't these already valuable? I now run my own startup and i feel i benefited a lot from my former stints in other startups, even when some of it fell into the "what not to do" category :)
Also in a startup you're more likely to need to wear multiple hats and deal with uncertainty, which are two things you'd definitely need to deal with even more in your own company.
As somebody who's worked at startups aplenty, this is ok advice for the first X years of your career, where X might be ~2-5. Beyond that, if you're still joining startups to found one eventually, you have to question what you're gaining from the time you spend at a startup. It is easy to claim you're preparing for an iron man triathlon, and just keep training and never actually participating in one.
Contra a lot of popular belief here: I don’t understand how working as an engineer (because this is always what seems to be implied) will improve your odds at starting a startup.
Working as an engineer, and kickstarting a business are two very different jobs.
Even in practice successful tech startup founders seems to be 40 yos with a background in management consulting. So I really wonder where do people get the idea that working as an engineer is a path towards entrepreneurship.
EDIT: and it’s rather ironic that the author doesn’t himself run his own startup.
I'm not sure most successful tech start-up founders have management consultant backgrounds, I've not seen that at least!
Speaking to the point about not having been a founder myself: you're right, and hope I was clear about that in the article. But I have spent the last year as the first employee working on building out a start-up, where a big challenge is in establishing a team and learning how to build a product that people want to buy.
When you build a start-up as a founder, you need to know how to do that stuff. Otherwise there won't be much point in being good at the founder-specific work like raising money etc, because there's not a business around it.
The main point is to try to minimise the 'firsts' you might have when you start your own company. If the only thing you're doing for the first time is exclusively founder responsibility, then I think you're much more likely to be successful.
> But I have spent the last year as the first employee working on building out a start-up, where a big challenge is in establishing a team and learning how to build a product that people want to buy.
Lots of people have these experiences but don’t succeed as founders.
I suspect a key difference is you are currently doing it without real risk, and with someone else’s risk appetite. I’d be wary of trying to apply the exact same approach when it’s your company on the line. So in that sense there will be just as many “firsts” either way.
The key assertion of the fine article seems to be that if you've worked as an engineer in a startup, then you at least have seen first-hand how startups work, how they are run, what problems they encounter and what solutions work/fail there. The dynamics of a startup are quite different from those in a large, stable (even if growing) company, so an ex-startup-engineer might have seen more relevant things than a middle manager from some Fortune 500 company.
No doubt my desire to start my own thing has increased 10x since joining a startup (back in November)
Why? I think it's a mix of:
- Getting comfortable building from scratch (we're early stage so almost everything we are doing right now is from the start)
- Getting comfortable with new technologies that previously felt inaccessible to me (ML, AI)
- Founders are very transparent with the operational and legal details of our startup, so I learn a bit here and there about the non-technical hard things
- The chase for the first dollars. This is really energizing (and hard) part of where I am at right now. It can be prone to burnout, but I do now want to try and go for my first $100/month
Counterpoint: I have seen some very bad habits carried over by founders from growing companies. Success isn't always the result of excellence.
Also, many founders that worked in somewhat larger environments before tend to rush into 'mature' processes long before their benefits outweigh their costs. This almost always grinds progress to a halt, creates a ton of middle management and other non-productive overhead in a startup/scaleup.
Even as a solo founder who’s worked at startups and large companies and knew to avoid this, I still did many mature/best practices that have slowed me down. I haven't discarded them, but I definitely set many of them aside until later.
As an employee, you need to vhet the startup even more closely than an investor. An investor will spread their money to multiple startups; but you can only have a single full time job at a time.
Now imagine absolutely inexperienced founders and external senior management. You have a total lack of knowledge around how to run an org combined with the urge to rush into super-mature organisations. That is fun...
I've been speaking with friends about starting their own companies recently, and one thing it's made me consider is what experience would best prepare you to become a founder.
Having spent my career in start-ups, the idea of founding my own without first working at one and seeing what works terrifies me. There's so much stuff you only learn from doing it over and over again, at different company sizes, and seeing how it works/doesn't.
I thought it might be useful to share some of that experience, if only to justify why joining an existing start-up can be an amazing education for anyone wanting to start their own. As opposed to, for example, joining an existing big-corp or jumping straight into start-ups without that experience.
Want to found a startup? Just become great at your craft. Dont waste time with success stories and their advices, because it is all survivor bias. Just keep building.
This and “never give up” are the only solid startup advice one should follow.
What I work on today I can imagine myself doing until I die.
I’m 15 years into my first startup and 3 into my second. Maybe it takes a simpleminded person to have that patience but that’s how you win.
I haven't worked at a startup. I have worked at two FAANGs (F+G). So I can't speak to the actual experience of this but when considering options, startups, particuarly very early stage startups, seemed like such a terrible value proposition.
There could be qualitative benefits and I think this is why a lot of people go this route. Things like less structure and a bigger feeling of impact.
But your equity is most likely going to be worth exactly $0 and the upside isn't really that high. For every Craig Silverstein there are 100,000 people who got nothing. Look back at any HN thread where people are asked about their exits (as an employee) and it's sobering. $10-20k after 4-5 years is disturbingly common.
A first employee if they have a lot of pull might get what? 0.5%? Maybe 1% if they're a rock star? It gets worse than that because your equity and founder equity (let alone the investor's equity) aren't the same. Theirs will have things like liquidation preferences and participating preferred. Yours may well just disappear on dilution or the kiss of death: a down round.
If your startup gets bought in the sub-$100 million range, the acquirer might avoid paying out employees by giving signing bonuses to the founders to join as VPs and pay out the investors while paying pennies on the dollar to common shareholders. This may have changed but there were rules around acquiring companies for less than ~$60 million that meant it was much better to buy the company for $60m and pay founder signing bonuses for another $40 million rather than acquiring it for $100 million and that $40 million difference is coming out of your pocket.
On top of all that, you, as an employee, will have very limited opportunities to liquidiate your equity prior to an IPO that will probably never happen (you'll get acquired instead and that company may well be public). Founders and investors may sell some of their equity on future rounds. Sometimes employees will have access to this but often they won't.
Now compare this to the FAANG path. It's pretty easy to get to $400k+ total comp for really not that much stress and very little uncertainty. You'll never make $100 million this way (unless you become an SVP+) but let's face it, your startup isn't making you $100 million either.
Honestly, things like this read like VC propaganda just trying to keep the pipeline of warm bodies fed. Outliers are used to sell this well I have some outliers too: Jeff Bezos, Larry Page, Sergey Brin, Steve Jobs and Steve Wozniak. None of them worked for a startup first.
I don't see a lot of people arguing that vest and rest at FAANG is going to bring you more money and less stress - in the vast majority of cases - than working in a startup.
It's just that some people would rather have the stress, freedom and excitment that come with working at a startup, rather than completing their OKR to avoid being put on a PIP at the next PSC. Even if that means earning less money - on average.
Actually, Jeff Bezos worked at a startup, Fitel, for two years, as his first job out of college. (Maybe 1990 D.E. Shaw would be considered a startup, too, actually.) But good points regardless.
We have a "Founders Program" for people that know they want to start a company in the next few years. I think it's better to have full transparency on both sides:
As the company: You get highly motivated, amazing talent
As the employee / future founder: You make your intention clear to leave in x months to start your own thing and can openly discuss strategy for your company with the current founders instead of hiding your side projects.
I took this idea from Mighty / Supabase.
Application process is simple, pitch me at mike@luabase.com. Tell me what you want to do to grow Luabase and what you're thinking of doing for your company.
We have a few people who are explicitly at incident.io to gain experience of how to build companies. It may be that they won't go to do this, but their time here will put them in a great position to do so, if they ever want to.
I've seen some companies who have a standing offer to angel invest in your start-up too, though I was never sure how I felt about that.
On the angel investing, I was thinking that was the next logical step too but rather than building an internal mechanism and pulling focus I wonder if you could just partner with an early stage vc to give them first look in return for special consideration and earlier mentorship or something. Tons of early vc's with dry powder and minimal differentiation to lean on!
So we are doing exactly this, which is cool! I think the primary value is in leveraging the investor network, as you say, though the angel investment is a nice bonus.
That's a super cool program, props to you for actually putting it in place! I guess the next step is to also have a small internal vc mechanism (or partnership with a vc firm) that gives the first check to people who join? I know that'd be a huge plus for me just as an option for something I could potentially rotate to in the future if I was thinking of joining a new co, it definitely sends a strong pro-entrepreneurial signal regardless of whether you're founding something or not.
We'd never write checks out of the company, but I personally angel invest and make intros to our investors and any others I've talked to. I've pitched nearly every VC someone would want to talk to.
How do you pick a high-growth startup that makes it through several stages? It's like saying the best way to make money is to pick stocks that beat the market.
Look for the phrase "scale-up" instead of "start-up", these are usually well-funded, up-and-running companies that still have some of the start-up mentality but without the financial worries.
Of course, some of these are already a decade old and may employ hundreds or thousands of people already, so YMMV; they might just be like older, boring enterprises, just not as formal or fixed in their ways.
Those are companies that believe they have product market fit though. At that point they are starting to transform from a startup into an established company.
So most of the early stage learnings can no longer happen.
Look at their investors. When interviewing, ask to speak to the investors. See what they say. When speaking with founders do they have numbers they can show or is it pure show-personship?
I mentioned this above, but unlike an investor you don't have to pick a start-up that exits successfully for you to gain really valuable experience that can help you on your own.
Pick a company with a team you respect, a product you connect with, and has money in the bank (just completed a funding round).
You can't go much wrong if you do that, at least in terms of learning.
I don't buy this argument at all. It fully depends on your mindset. No big company pays you to become lazy and entitled, at least not the FAANG ones referred to by most as the gold standard. If you cannot show initiative and growth in a big company you don't belong in a start up. People with initiative and a drive to do things thrive anywhere and in any condition. They solve problems no matter what the form is and forge ahead. I do see that working for a startup can be great, but this whole "work at a start up first" is just trying to glorify startups and nothing else.
I've worked at several startups, but my experience has been that I've been relatively siloed in my work. Maybe I wasn't taking advantage of the startup experience, but aside my limited view at standups, I didn't know how the sausage was made in different areas of the company. I couldn't see how it all fit together, because I had an incomplete picture.
This is like half the sell from start up ceos. "Want to start your own company someday? Come here and get paid to learn how to do that."
As many other have said... You might learn how to run a start up but its just as likely you will be able to see mistakes the company you joined made and hopefully be able to prevent your company from making those same ones.
For me, it was good to see that the person who started the start up I worked at was just a normal guy. He hired this CTO though that was amazing to work with.
Unfortunately, my impostor syndrome (along with my inexperience) became quite crippling and I had to leave.
Looking back, I probably should have left sooner or been comfortable with standing up for myself.
I think a better framing would be: Want to found a company? Work at one first.
Every startup is different. A bootstrapped startup that has to be cashflow positive from day one is different than one built on an initial investment.
Having work experience also means you can better understand if a startup model is actually appropriate for what you're trying to build. Startups in the sense that VCs use the term are high risk high reward and optimize growth for a high ROI exit. This is great if you want to take the gamble for a chance to retire at 35, not so great if you just want a fulfilling work life or can't afford to loose.
The quickest way to tank a startup is to run out of money, yours or your investors'. I guess if you want to optimize for outcomes, the best advice would simply be: Want to found a startup? Be wealthy. But that doesn't make for a good blog post.
> Almost immediately after I arrived, I learned our VP of Engineering – who I hugely respected – was leaving. Disappointing, but nothing like the shock one month later when, at a Friday debrief, it was announced that our CTO and the two other most senior engineers had also resigned.
> I remember that meeting, where I and two others remained at the table after everyone else had left the boardroom. “Shit” and “well this is fucked” was all we managed to say into the shocked silence, and I began to worry that I’d made a terrible mistake.
This was my experience, too. The company just released its v2 app and was having meetings finalizing an acquisition the first week I was there. Within 5 months, the engineering team I worked on went from 7-8 employees to 3, including the resignation of the CTO. It's going alright now, but it definitely was worrisome.
> it was announced that our CTO and the two other most senior engineers had also resigned
> As it turned out, everything was pretty much fine. Different for sure, but people step up and companies evolve, and while it was challenging to fill the gap made by those who had left, it happened faster than you might expect.
> Knowing you’ve been there before is what allows you to respond with “I know this will be ok” instead of overreacting, or allowing the situation to impact you too harshly
This is spot on and I can deeply relate. In my startup (150 employees) we had some senior devs departures and the Junior staff was acutely impacted, requiring me to put a lot of effort into managing the situation and reassuring the team we'd overcome it. Fast forward 3 months and we have filled the vacant positions, morale is good again and productivity is mostly restored.
Idea generator and fundraising are also a couple of benefits to joining a startup before starting your own.
1. Finding ideas can be hard especially when you start from scratch. Most startups (particularly fast scaling ones) can give you ideas if you look for:
* de-prioritized ideas due to "hyper-focus"
* listening to common problems that customers [0] have that aren't necessarily solved by your company.
* product features built that many other companies would find useful (e.g. collaborative editing infra)
* internal tooling that other companies would find useful
2. Fundraising[1]
Many friends got their first checks from investors that were investors of a startup they previously worked at. And the truth is, if you choose a slow-scaling/zombie startup, you will learn a ton still but honestly, the investors of that company aren't going to be stoked to invest in you if you spin out your own thing.
A quick list of common strategies that worked for them:
* Choose founders who don't treat investors as "dumb money"
* Choose companies backed by great investors
* Join startups that are scaling fast
* Join early (< 40) so you can be part of the "success story"
* Ask to meet the investors throughout your tenure (ideally you are upfront with the founders of the company you join)
* Stay there and be a part of the solution through 2+ tough moments (ie. investors can associate you with the success of the company)
[0] Getting to know potential customers and understanding how to acquire them is also super useful.
[1] You can avoid the fundraising focus by going to YC (or equivalent) because you'll get the necessary clout to get investors knocking. If you're going to a startup anyway to get experience and find ideas, you may as well prep for fundraising.
I feel like this article makes valid points, but they don't necessarily support its conclusion. The question it asks whether to start a startup or work at another startup first. Yes, working at a startup and gaining experience will likely improve your abilities and increase your chances to succeed later. However, so would starting your own startup.
The question about working somewhere else is not "is it better than nothing", but "is it better than starting a startup now". It can be equally true that "founders that worked at other companies before are more likely to succeed" and "the ideal course of action for a person who wishes to start a successful startup is to start it now".
I think the thing about starting your own start-up without experience seeing what works elsewhere is you're highly unlikely to avoid making some big mistakes.
If you've spent time in a growing company and at least seen how things evolve over the years, you have an idea of what does work that you can base your first attempts against.
Trying to come up with novel solutions for everything from hiring to org structure is a recipe for pain, and I'd invest my money with a team of people who've experienced good versions of these things over those with none any day.
I don't doubt that. But you don't have to come up with 'novel solutions' for everything because you can read books, watch conference talks, listen to podcasts, read blog posts, by people who have done it before. Working somewhere will give you a very close and detailed, but n=1 experience of one company.
But I'm biased, as I started my first startup at 16 and failed, and proceeded to re-try at 18, and succeeded. I'm not doubting that someone with years of experience in high-growth startups would have been a better founder than me at 16, but I do think that starting a startup was a choice that lead me to startup success faster than trying to get a job and then attempting.
> and I'd invest my money with a team of people who've experienced good versions of these things over those with none any day.
This is an absolutely valid (and imo likely correct) assessment, but it's a different question than "What should I, as the potential founder or employee, do?".
Another bad stereotype is the university dropout founder. The reality is that most startup founders, especially the successful ones, come from Ivy League level universities if you look at the data. This makes sense from the perspective of risk mitigation
Potentially good advice here, but some of the details seem off to me. Here are some quick attempts to summarize hopefully as constructive criticism:
In my experience the best options are almost always the middle ground. That is, the startup mentality drives sloppiness and excuses while the big company mentality drives slowness and perfectionism. The best option is somewhere in between. At a startup it can often be extremely valuable to have a "parent in the room" enforce big company thinking and oversight, and at a big company it is almost always useful to at least envision a shorter path than the usual consult with everyone and make a design and see how it goes kind of thing.
The "allows you to respond with “I know this will be ok”" statement as a reaction to major changes and challenges sets off red lights all over my dashboard. The situation will be okay because you made it okay. This is true in companies of all sizes. Fail to take responsibility for the full situation and you are likely doomed.
The "any process you introduce will break by the time you double the headcount" strikes me as classic startup sloppiness. If you really know what the situation is and why you are doing what you are doing then even when changes are necessary it is usually quite explicitly clear what and why. Solid processes and operations often go the other way: even with significant changes the core ideas and methods endure, so be careful what you start with.
Hiring from your personal networks first is another classic sloppy startup error. This tends to end up with clubby teams made of people who aren't actually as good as they might be and that exclude the people you really want to hire. Better to start well outside your personal networks and bring people in as needed. Sorting out the interview process at least at first also works better if it isn't all friends and long time coworkers.
And this business of defining levels is a real mess. All the best organizations I have contributed to have been close to flat.
There are always many paths, but given how treacherous the path to startup success can be it seems worthwhile to air criticism.
Work in a startup where the founder has done it before and top management has some experience. I've worked in many startups and seen many more, and if people are not knowledgeable enough, you can't learn a great amount of things.
This article is not really about what’s unique about working at a startup that can give you an advantage when founding your own, but more about how to accelerate the learning of skills required to do so. Hence, the emphasis on high-growth startups.
But, obviously, not all high-growth startups can provide an environment of rapid learning. It’s not just about high-growth; it’s also about how much output the startup is trying to extract from its people. The more they try to extract, the faster the learning cycle. In that case, a high-growth startup with limited resource seems to be the ideal company to work for.
Does anyone care anymore about just having five kids and a backyard and a loving spouse and a wall full of books and solid church community? I'm so tired of people just trying to make money.
My wife and I are quite religious (LDS). We have 50~ nieces and nephews, 2 rooms full of books, a little over a half acre yard, grow a sizable percentage of our produce, and nature willing would like to have kids.
I still would like money though, lots of money. I need 600k-1 million USD to quit working just to live. With my current income, inflation, etc., I'll likely still be working until I physically can't though. If I magically had that 600k-1 million today to retire, I'd then be content on the money side. I would have the freedom to pursue whatever I wanted to do with my time, from volunteering way more to tinkering with crafts/considerably expanding our growing/YouTube/writing/whatever.
You can want a morally upright life with lots of personal relationships, and still want/dream of a nice little pile of money.
I have worked at a startup, joined the founding team of a startup, as well as consulted at a VC before. IMHO, I don't feel that it is a pre-requisite to work at one first. Though there are spirits a successful founder needs to have, but "working" at a startup is completely different from "owning" it. The mindset, pressure, things to handle, are at totally different levels for the founder. And that's not necessary being gained/build by working at a startup.
After working at a startup, I don't think I would ever start one because I'm not interested in exploiting people when it comes work life balance or compensation.
I would suggest joining even smaller than 40 if you can, although that’s not bad. I had joined a 250 person startup before founding my first company and I can say confidently I had no idea what I was getting myself into, and I think the experience would have helped.
Either way you’re going to be figuring out a lot of stuff on your own, but I think I would have recognised that earlier and would have had a little more practice.
Sounds like the big lesson is having autonomy to do whatever needs to be done to solve the problem at hand. Pattern matching how to handle situations based on previous success/failures might not be the best way to deal with early stage startup questions where you have to navigate unknown territory.
Good general advice -- it's been good advice for a lot longer than the term "startup" has been around.
But the choice of company you work for is important, too. Startups are not all the same. You should choose one in the same field as your interest, and one that operates with similar goals as yours.
The most important skill of the startup founder is to find funding and customer, while find talent to implement, and if there is no suitable talent at that time, he can at least take the task until find someone. None of these skills can be acquired if you just work for a startup.
I think I failed to communicate this nuance in the article, but my major point was how to most quickly develop the experience you'd need to start your own company.
I'd imagine McKinsey is a great place to see loads of companies and be exposed to a lot of useful stuff. But it probably won't pack as much relevant experience into as short a time as several years in a start-up 5-10x'ing in size.
Hiroki Takeuchi and Matt Robinson – two of the GoCardless founders – both left McKinsey to start GC. I'd imagine that experience was incredibly useful, though you'd have to ask them if they think it's more or less valuable than seeing things at a different start-up beforehand.
Really, the secret ingredient was McKinsey? Maybe I'm biased but except for one person, I've never worked with McKinsey folks (and working in Germany you work with many) and thought they'd be great entrepreneurs
I give this advice to many aspiring founders I meet and I practice it myself. Have been working in multiple early-stage and growth startups at different stages with the goal of becoming a founder one day including right now at FlyCode (S22)
Working at startup sucks. Lower pay, lower stability, overworked, much higher risk for the company to go bust. There is literally no benefit apart from the fact that the bar is somewhat lower and easier to get a job
Most startups don't know what they are doing, so first-time starter-uppers get the wrong idea. Instead of moving at a steady pace without burnout, the lesson they can take away from it is that startups are all about heroics and working until 2AM while chugging tequila.
There are a lot of clowns out there with a serious case of Dunning-Kruger who run these companies (usually into the ground).
I've worked for startups, both under an agency and as a contractor, and IMHO the problem isn't how well a startup executes, it's how much runway it has. Or some combination of those things. We can always gain experience and improve our execution, but funding is (sadly) still an open problem.
I adore HN obviously, but am concerned about the idea of mentorship as a prerequisite to success. Truthfully, I was far more clever fresh out of college at 21 than I am in midlife after learning how to supposedly do things better. All I needed was any money at all to work on my own projects (something like $24,000 annually in the year 2000) but nothing like that existed. We didn't even have Kickstarter. So I worked a bunch of dead end jobs making rent and all but wasted the most productive years of my life.
But there have been several changes over the last 20 years that removed the artificial barriers to entry that kept me and makers like me on the outside. The main one being the JOBS Act of 2012:
If I were starting out now, I would largely ignore what other people are doing, and figure out a way to raise 2+ years of income, or at least $100,000 per person, by checking all of the boxes needed for crowdfunding. Then show the campaign to older people who have some disposable income that want to invest outside usurious and rent-seeking systems like stock markets and real estate.
Then I would use something like a referral program to bootstrap:
Everything else on the technical side is honestly pretty easy to figure out for programmers. There's just not that much to learn, it's mostly about balancing process with pivoting to make steady forward progress each day. Two-person teams have been more productive than entire companies.
And nobody wants to hear it, but, I feel that up to 90% of "best practices" today are about working around fundamental inadequacies in our tools which still haven't been addressed. For example, all databases needed event streams (like Supabase) so that we could have had reactive programming from the beginning. Jira and countless other similar tools have just not kept up with their errata. The level of expertise needed to set up cloud deployments has passed the point of believability. Native mobile development probably shouldn't be a thing, except for certain performance-critical components. And so on.
The big opportunities today are probably NOT in the typical high-effort approaches common to startups mired in scaling issues. We can look down the road a little and bypass those eventualities, assuming that we can scrape up enough funding to work independently and avoid groupthink.
As someone that spent 15 and a half years working for FedEx and then jumped ship to join TrueNorth shortly after their Series B I've definitely found it interesting.
FedEx:
- an ancient dinosaur, using a LOT of ancient tech (I did my job in an AS400 terminal for 15 and a half years).
- A bureaucratic dinosaur, even backfilling positions could take 6 months just to get a posting and even simple office fun activities had to be kicked up the chain to corporate legal for approval
- You were a serial number, mine was 628254
- Everything I did was micromanaged to the second via time stamps
- Reviews were rigid, mechanical, impersonal
TrueNorth:
- Agile, even in the 6 months I've been there things have rapidly changed (and for the better) and that just blows my mind. I know it's normal for a startup but it's truly like magic to me.
- Not a bureaucratic dinosaur, our CEO is hands on in the trenches still. She's there asking questions, looking for feedback, keeping a decent working knowledge of everything that is going on. There aren't a dozen people between her and the lowest rung of the ladder.
- I'm not a serial number, I'm just Ryan. I'm treated like a human being.
- Reviews are typical for modern companies. I can also ask my boss for feedback any time and, unlike at FedEx, know I'm going to get actionable feedback and not have him scrutinizing everything I do for the next few days/weeks wondering what I'm trying to hide/cover up in my work.
---
I definitely see a lot at TN that is being done much better than at a dinosaur like FedEx, we have the ability to just try something if we think it's going to work better unlike at FedEx where it would have to be kicked up through multiple rungs of management, then non software engineers would be tasked to investigate it, then maybe 3-4 months later a very limited time study would get approved and done, and then that new process - regardless of if it was better - would get buried. At a startup it's just "sure, give it a try, see what happens" most of the time or a much more immediate feedback "actually, that is going to be an issue because of x, y, and z".
I did join TN when it was north of 50 people though. It had 2 years and change of operating before I joined so I did miss out on the truly chaotic bits but 100% I would say I'm now better equipped for either a brand spankin' new startup or a decades old company due to my time here. I absolutely think differently than when I started 6 months ago and I don't feel stifled by some antiquated system of doing business. If I have an idea I can go explore it, or even try it, I can grab 15 minutes from someone's calendar to ask why they're doing something a certain way and what about it is annoying/is awesome, and I can take that and maybe apply it to my work or even let my brain percolate on how to improve that for them.
If I ever had an idea for a startup, I 100% feel better equipped to take stab at it now that I've worked for one. I definitely know what is working as far as communication, documentation, scoping, etc.
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 :)