Ask HN: Leaving a Job at Big Tech Giants for Startup | Hacker News Reader

Ask HN: Leaving a Job at Big Tech Giants for Startup

79 pointssujesh68 comments

What does HN think about leaving a posh job at big tech giants for creating a startup?

My entire career has been startups. On average, your startup will be a failure.

If you want to create one, then it should be for an idea that you really believe in and that has value. Because you're going to have bad days--lots of them--and want to quit. And if you don't believe in what you're building, then you will quit, and it'll all be for nothing. (Plus, if you believe in what you're building and it fails, you won't regret it later.. you'll at least appreciate what you learned.)

The fact that you're asking at all, tells me you should probably stay at your job. If I (a random 3rd party) needs to convince you to do a startup, then forget it. The idea must not be very compelling--it certainly isn't to you.

And if you're thinking that is the path because you've read a bunch of success porn.. you're in for a rude awakening.

Yep money comes second , product validation and market fit comes first

Well, there's two types of money, aren't there?

"Real" money comes after product development, market fit testing, market penetration, iteration, supporting early adopters, building market presence, etc.

"Virtual" money comes after product sketching, roadmapping, pitching to VCs, and cashing out (ideally before the 'market fit testing' stage.)

Edit: Oof, unpopular opinion apparently.

The issue is, that if you want to create a startup because you want to get rich from it, it's the wrong attitude all together and will probably fail. Your concern shouldn't be how to get rich quick, but how to build a viable product that solves a real issue. If you get that done, the money will come.

Ha ha! I've sometimes joked that when you start a startup you have to decide who the "customer" is -- the person using the service or the VC. I've definitely worked at startups that were milking VCs. I don't really recommend it as a thing for technically minded people to do because you end up doing a lot of crazy stuff that has nothing to do with making a good product. But it definitely happens.

Precisely.

This.

The probability is that your startup will fail.

However, you would not have failed as an individual if you're passionate about what you're building, and enjoyed building it, whatever the eventual outcome.

Correction: You will not have made the wrong decision if you enjoyed the experience enough to pay hundreds of thousands of dollars for it.

This, pick something you really care about and would be willing to eat and breathe for a long, long time, because if you succeed at it, you're going to be doing it for a while. Don't aim for the Instagram style "exit for 1B in two years", if that's the goal the go to Vegas, it will save you a lot of time and tears.

If you don't, and if you're luckier than most, you might get stuck working on an idea or in an industry you really don't care about, just because you wanted to play startup and, like the poster above said, you read up on a bunch of success porn that's telling you that startups are the sexy, right thing for you.

Then you'll be stuck between a rock and a hard place, hating what you do for years, but not being able to leave because of all of the sunk cost, the shame of abandoning the team of people you've brought on board and convinced to chase a dream you don't really care about yourself, the reputation hit, the VCs who sunk all that cash into you, and the carrot of a potential, however tiny exit dangling in front of you. And the years keep adding up as you're chasing that carrot, still dreaming every day of getting out, but somehow that exit just never happens. If you're lucky/smart you'll find someone to replace you, but then they might kill the golden goose and you're still left with nothing, but at least you moved on, so that's a silver lining.

Fall in love with the problem and with the mission, that way, even if you fail or have a pretty rough time, at least you're working on something that truly matters to you. And "doing a startup" can't be the mission in itself, that's a recipe for disaster. It's one of those situations where even if you win, you still lose.

Second this. You might not even fail outright but rather realize you've worked every hour of every day for years for an average gain of a couple dollars an hour. You can do it if the environment is right for you to thrive (i.e. build something of great value) and you can tolerate the risks involved.

This too.

I've worked for startups a few years now, and as many HN commenters here have said, you WILL have many bad days. You'll see crazy shit once in a while, so it's almost always easier to answer your question by starting with why NOT to join a startup.

Justin Kan has a good writeup on this: https://www.atrium.co/blog/work-at-a-startup/

Read it, and then read it a second time. On your second pass, put more thought on the "what if the startup fails", as one tends to overestimate the upside (riches etc.) without weighing out the downside of the risks involved. Unless you feel "yes, this is what I sign up for" very strongly, you probably shouldn't.

Just to wrap this point up, here's why I'm where I'm at. I've "roughly" figured out something I can live with in my career. Working in a big company with big bureaucracy, slow processes and being told to do something insignificant kills me, and I'm better off working at startups and hopefully start something my own later on, despite the potential downsides.

Building on this. I've been deeply involved (4+ years at each) in three startups. Two where acquired and one is still going profitable. I wore a lot of hats and learned an amazing amount of stuff at all of them. Despite my lucky track record, the main financial benefit I got was being acquired while I was an executive of one startup. My 1% stake was worthless, but the retention cash and RSUs I got from the acquiring company weren't insignificant. Most people got a much smaller amount of cash and RSUs were on par with any other employee of the company.

If you want to learn, grow, and be a big fish in a small pond, go for a startup. It's fun, frenetic, stressful at times, and you can have as big an impact as you want. If you have dreams of $$$, stay at a public company that can shower you with cash and RSUs.

I have a friend who has been at 3 startups in the last 8 years and he regrets being in the startups immensely, because of how much money he has left on the table not being at Apple and Google (he was at both previous). He probably missed out on multi-millions of dollars in stock/RSUs and none of his startups panned out at all.

So, your mileage may vary.

Me personally I've done both, and I think I prefer a small, public company where my RSUs are worth something that I can sell. I don't need multi-millions, but I do need money to survive in the Bay Area.

Money is an important factor. I think in the startup ecosystem money comes second. Validating idea, iteration over it and making it market fit is a long process. Making money comes after that.

I've made more on paper in growth of equity in my home than any of the startups I've worked at. Granted my first job was at a big tech with options right out of college, which allowed me the down payment on home, but ever since....I've been picking the paper losers to work at (or start). I'd have been way better off (financially) had I just stayed at my big tech company since college, worked my way up to Senior Management, kept getting stock grants, bonuses, etc. And now, I'd be getting dividends on all that stock, too.

However, I've had lot of fun and mostly enjoyed my career being kept on my toes.

YOLO

I peek at Blind every now and then (and take everything I read with a grain of salt) but main takeaway is that there are plenty of people at FAANGs who pull in a good amount of money but are completely miserable because they have allowed themselves to get wrapped up in a rat race where all they can think of is their next raise/promotion within some arbitrary leveling system to measure their self worth against.

Also reminded with how money is not happiness with the crazy story with Jussie Smollett staging his own hate crime because he was depressed about his salary of $1m a tv season.

I think they're completely miserable because they don't know how good they actually have it. If they can unwrap their ego from the rat race then they would be much happier.

Compare that with the founders who don't make any money and have no big home runs. Some go bankrupt. But at least they chased the dream. Which would people prefer? Grass is not always greener on the other side.

I was working at Google and I'm really happy to read what's going on on Blind to be able to talk about the worst problems that are going on that you can't talk about on the internal system.

At the same time it's still a great place to work at as long as you find the right team (especially team lead).

In my personal opinion if you are doing something that risky do it when you are young. Once you cross a particular age threshold your possibilities of future pivots back to jobs will be decreased considerably. Especially in the tech industry ageism does exist. And at a young age you tend to take a more irrational leap of faiths and to an extent, that's a must for an entrepreneur in his early stages.

In my own experience, i jumped into the entrepreneurial journey right after my graduation. Was it a well thought out decision. No of course not. It was a kid chasing his dreams. All cliches aside sometimes dreams don't feed you. But if you ask me "do i regret", i would confidently say No. If you choose to be an entrepreneur, no one or no book in the world can prepare you for the shit that you are going to face and 60% of the time you'll have bad experiences. So why choose it over a well-paying job? That's a question you might have to answer. And that answer will change over time. If you go with it, be prepared for the following

It not fun (As mainstream media portray it to be). Every morning when you wake up & your rational mind will ask you why? be prepared with an answer. Embrace the uncertainty and learn to survive on hope.

And finally, save some money at least to survive for 3 years. Live frugally

This was roughly my thinking. When I was young, single, and had no responsibilities, I did the startup route and thrived in the stress, excitement, and ability to make a big impact. Now that I'm older and have a kid, a public company with RSUs that I can put a dollar amount on (vs. options), and some measure of stability are important. When I was 24, I could find a couch to crash on while getting back on my feet if the job went south. Now, I'm worrying about college, mortgages, and stability.

I like to be at a small corporation (we're about 70 people, 25 of which on the tech side). We work on things that I think are important, I have real influence in how everything is done, and it's still a normal job where I don't have to put in insane hours.

There isn't a binary choice between Big Tech and Startup.

If your motivation is making multi-millions one day, you're better off buying a lottery ticket or staying at your FAANG-equivalent job.

I left my large company job 7 years ago to found my own company with a friend. We initially tried our hand at a saas product then figured out we were too green at the business side of things to make it work (read we had no idea how to sell) so moved on to web-dev consulting.

Consulting has been a huge slog, we made every mistake in the book we could (and learnt from them) so we were making meagre salaries for a number of years. However we (lucked out and) met some great people who wanted to start new Saas products with us and could take care of selling and marketing while we build and product manage.

Now we've made our way back to boostrapped-saas-product-land much wiser than before. Been at it for a year now so not quite ramen profitable yet. I am poor AF, my cofounder is poor AF, we are late 30s/early 40s now.

The only reason why we come to work each day is because we have products we believe in, customers who we want to help and employees who we love (and wish we could pay more).

This has been made possible by understanding wives and families too who are happy to scrimp now for a shot at a future they believe in too.

I'm in a similar situation. How are you holding up?

Thanks for asking, I'm alright. I used to have this thought process which was 'if I didn't make X metric by Y date, I'd give this all up and go back to BigCo', well sure enough I've never ever made it but I'm still kicking around. I had to read a bunch of philosophy particularly on stoicism to get me through some of the tougher times a couple of years ago.

There's no point in focusing on the money/wealth that I didn't earn over the years because I took this path and I made a choice to. What matters is the here and now. That's not to say I don't plan for the future but I boiled it down to a simple trick to keep me going - is there progress? Is your trajectory up or down? If up, no matter how small or slow the progress is, keep grinding away another day/week/month. We're slowly adding customers, slowly improving our product to be indispensible to our current customers and getting paid on a monthly basis for it so there's a pin-hole of light at the end of the tunnel. I've already paddled half way across the ocean, I just have to keep going on.

"If I don't make X metric by Y date..."

I've found this to be the most dangerous type of thinking. It's always going to take longer, go worse and be harder than any of your best estimates. When you don't meet your dates or metrics, that's when you'll lose your motivation.

The key to keep grinding away relentlessly on a project is to improve habits and systems for making progress. The creator of Dilbert wrote a great book about it:

https://www.wsj.com/articles/scott-adams8217-secret-of-succe...

Personally I don't consider myself successful, but because of the advice to stop making goals I'm failing faster, staying motivated and getting stuff done. So hopefully eventually it will pay off.

I left Facebook 3.5 years ago to start a startup and I'm quite happy.

Software engineer and founder are two different roles, and it takes time to transition. Don't expect to be wildly successful in any short period of time.

Launch quickly and try to get users and talk to them. Try to make your first dollar quickly. This will help you learn about business, marketing, product market fit.

I believe that starting a bootstrapped SaaS startup minimizes your risk and maximizes your outcome. It's relatively easy to make money and become profitable, compared to other kinds of startups. Once you're profitable, it's hard to die.

Lastly, bring a designer with you from big co (assuming you're an engineer). People want to use well designed products, and simple UX coverts better.

easy to build means easy to replace. is it true?

Not in my experience, so far.

Most of us here on HN have done a startup, been an early employee of a startup or hang out here at least in part because we dream of doing a startup. Given those biases I think the default is leaning that way.

On the other hand you already appear to be living the alternate dream talked about often here on HN - good job at a tech giant at least if it is one of the FANG and not one of the older school tech giants.

My own experiences would indicate that one should not underestimate the likelihood of market failure. When we say "high risk high reward" many of us focus much more on the second half of that phrase and discount the first half. We assume that we are smart enough to avoid the risks and persevere till we reap the rewards. And, sometimes we are, but often we are not.

Just the other day I ruminated with a friend that I almost certainly would have been a lot better off financially picking a boring but useful domain and getting really good at that rather route that I did take. Focusing on R&D, innovation and a couple of versions of startups. On the other hand I feel like my life has been pretty interesting.

I work at a startup in India. I saw many articles on quitting jobs from big companies and pursuing dreams. I was very curious to know how are they balancing their work and life. Creating a startup is very difficult than a job at the company. Unless it's a high funded startup, most of the founders handle all the department. The stress is very high. Iteration over the product idea is another thing that makes crazy. How are you guys manage all that? But passion is a fancy word!!!

My experience working at a startup biased me against it. I'm much happier at a big tech giant.

Totally agree. I'm not at a company known as a "tech company," but it is a household name. Vastly superior in pay and culture to the startup I worked for.

I did this and my advice would be “it depends”. It’s been a mixed bag. Financially I’m much worse off than I would have been staying at my 300k job (who knows what it would have grown to now?). I will say the stress of not knowing what you are doing and questioning yourself can be immense. That being said perhaps I’m not the best example as I took years off living a hedonistic lifestyle and truly adopted the YOLO mentality. I consulted here and there. It was fun but ultimately draining.

The corporate coding lifestyle can be without a doubt an existential mind fuck. It partially depends on your mindset and job responsibilities though. If you care about the purpose of your product, you aren’t some product managers code monkey, and you are making money that isn’t the worst thing.

That being said... FOR ME I have learned that the concept of retirement is a joke. It’s not all that great and at least for me people feel better having a meaningful purpose. Even if your purpose is make believe I think it’s neCessary. So I wonder about the utility of doing something you hate for 30 years just to end up “retired” and miserable anyway. That’s what I’m trying to do, I don’t want to retire but I don’t want to sit in front of a computer coding up some app UI for someone else. but I have a family on the way so we’ll see how it goes.

I think maybe optimize for that purpose you have in mind for yourself rather than starting a business just for the hell of it. If you are getting paid 500k by google to prosecute child pornographers that’s likely going to make you feel better than starting your own 1 man SaaS business running email marketing....

It depends.

Been at bigco, did a few startups, a couple paid out, most did not.

As an option, I'ld explore a side-hustle first, see if you like doing that enough before going all-in. Your goal for side-hustle, 20k MRR or gross margin monthly (ecom). Choose a metric that's real. If you can't hit it on a part time basis, you probably won't make it on a full time basis (for venture style startups that is. If you're targeting lifestyle growth levels, you can always do that part time. So what if it take 3x longer because you spend 2 days a week instead of 6 on it. ).

Run it like a startup, eg. hire folks, pay for them (out of your salary), manage them, build out specs/build stuff/etc. Do all the things you would need to create a startup. Low risk, a little expensive as an experiment, but if you didn't leave your posh job, you can afford it. eg. it's a 100-200k experiment, but that's 'ok'. You'ld have certainty.

I've seen many many of my friends try the side hustle, and none succeed. Mostly they burn themselves out from working so many hours and then stuff gets tough, as it does, and they bail. I think a better approach is to make some savings and take a sabbatical to test out what it's really like. If your day job is cushy and unstressful then maybe that's a different story...

^ This, so true. Lot of people preaching the side hustle who either havent actually tried it OR have very lax jobs that allow for this kind of thing.

So since none of your friends succeeded in doing a side hustle that means you shouldn't?

Yes. Doing a (venture) startup is tough. If someone can't handle the stress/hours/etc of building out a side-hustle.. they won't succeed as a founder of a full fledged startup either. It's a signal. Stay in the job.

Sabbatical: yep. definitely do that if possible/available.

If you have savings to cover at least 1.5 years worth of expenses, do it. If within a year you don’t manage to pull it off, you can always go back. I just did so myself. 2 weeks ago I left a very cushy job at Amazon making $500K/year to work for myself. I wrote more about it here: https://medium.com/@dvassallo/only-intrinsic-motivation-last...

Don’t bother with people saying you can only do this at a very young age. I’m 35, have 2 small kids (ages 2 and 4), and no household income right now. You don’t need to risk anything important to try your own thing. I wrote about my risk taking attitude here: https://medium.com/@dvassallo/freedom-from-success-54ca98fd6...

You were making $500k a year, that isn't normal, regardless of what you tell yourself.

His medium post said he was making that while leveled as a senior engineer.

Using levels.fyi and the sde 3 title, it looks like the average for that position in San Francisco is $482,000/year.

https://www.levels.fyi/SE/Amazon/Google/Facebook

I've seen people speak of how big corporations state-side offer more pay and packages, and that startups are mostly for the bored looking for new challenges and make their mark (plus a little gambling of their time that the startup will make it big).

Can confirm the same situation in Europe (Germany). With that said, I'd advise against joining a startup. In Germany, even with stereotypically strict laws favoring the employee, startups are extremely abusive.

- They will lowball you - They will lie to you about all the "great perks", mostly free fruit. Very rarely do they offer stock options and if they do, the terms designed to screw you over as much as possible (e.g. if the company doesn't go public or get bought over in 5 years, the value of any options is zero) - They expect you to work long hours, disregarding any "work-life balance" BS stereotypes about the way Europeans work

Founders fall in love with there idea and that shades the conversation creating lies.

You may also want to consider the timing in the economic cycle. During the last recession Paul Graham wrote an essay or post to say that was a good time to start a venture. IIRC he mentioned plenty of talent available cheaply, not many competitors in your space... The corollary may be that now is not a good time to start a venture- shortage of talent at astronomical costs, multiple competitors in every niche... The current market reminds me a lot of the dotcom bubble. And the first response saying 'this time it's different', I'm going straight out to short tech stocks.

I would say no to the people who say it's good to have a startup when you're young. For investing and money compounding the first 5-10 years of your working life are the most important.

If you want to make a lot of money, I would look at investing (especially commodities now that stocks/bonds/houses are overvalued) instead of trying a startup. Most people get rich ($3M+) by investing and letting compounding do its job.

Doing a startup is risky, investing can be done in a relatively safe way.

If you really want a startup for some non-money related reason, you can do it when you have money in your bank account.

I’m finding this out the hard way. I recently shut down a startup that became very distant from my interests, and now I’m having trouble finding jobs in my actual interest area, hardware engineering. I’m no longer a ‘recent grad’ so my college internships don’t have much weight. I wish I had taken advantage of the amazing opportunities afforded by being a fresh grad instead of starting my own thing, and I wish I had had the foresight to not do a startup that would distract me from my career path.

I'm sorry for you, I know heavy is the age bias in the industry.

Get a software engineering job at a company thst has hardware engineering as well, it's usually easier to switch as an insider.

All of the responses in this thread are vague because your question is vague.

If you have put away enough money to fund your own idea or live salary free for a year (or amount of time you're comfortable with not earning) then go for it. If this is just some itch you're looking to scratch try changing team in your company first and see if you still want to leave.

This question depends on so many variables that you can't possibly expect someone to give you a clear answer.

What matters more than leaving the posh job is to know what you're leaping into. Will the problem and company you work at be something you want to wake up and work on for the next 7-10 years? Are the founders people you love spending every moment of your waking hours with? Are they pleasant when you disagree with them?

If you have a current opportunity, it would be much easier to compare X with Y than talking about hypotheticals, so my advice is keep looking around for opportunities, and once one arrises think hard and then think again and then take the leap.

In the meantime, focus on becoming a kick-ass coder and/or product person and/or manager and/or fundraiser and/or marketer because these are all critical skills for building successful organizations.

I am currently a masters student doing a 4+1 year program in a prestigious school CS department. I know that if I go work at a big tech company, I will have no motivation to put in my 110% effort, so that's what influenced my decision to join a medium-sized startup. Besides, life is too short to be doing something you don't enjoy.

Validate demand and validate yourself.

Validate demand: You should understand whether you can launch a very crude version/maybe no product but customers lined up to pay you for your thing which'll become ready soon and get some validation from the market. If you can't do this, what makes you think that you can do it after you quit? Stay at your job if customers are not ready to throw money at you. If you can see solid demand, you should validate yourself.

Validate yourself: Do you think you are mentally prepared? Do you have enough savings? You probably have the skills to create a product, but do you have the skills to create a company? Will you enjoy working on this for the next 5-10 years?

On savings: Do the math for yourself, but in order to be able to work without financial stress, you should have enough money for = ((number of months you foresee your startup to take off) x 2.5[correction for you optimism] + 3-6 months[It'll become hard to work stress free and irrational to continue if you don't have something solid, so better go get a job now]) * (amount you think you'll need in a month * 1.3-1.5[you are also optimistic about your expenses])

It certainly depends on how you're approaching it. If you're thinking it's a chance to make more money, nope, you're better off making money at your posh job, or switch to a company focused on maximum payout (e.g. netflix). If you're passionate about it no matter what and are willing to work through five years of continuous failure (e.g. airbnb's story), then no need to ask, you're going to do it no matter what.

However, if you're somewhere in the middle, I think startups are a great learning experience. Go work at an early-stage startup that will pay you less than your current job and less than your market rate, but you get to experience a different style of company and style of work. Or save up money from your posh job so you can afford to not make money for a year and try starting your own company for that time. Or just coast a bit at your posh job and take that extra energy and put it into starting a side business.

What's your take on a side business? What kind of thing could it be? And would it be legal?

Big tech giants also have ton of interesting work to be done, yes the pace may be slower than what it would be at a startup or if you just go on a sabbatical. On the flip side, big tech can give you the resources you need to succeed.

Why don't you find an intersection between your idea or the reason you leave the big tech and the big tech itself? Then work it out with your manager to transition to that. It may take time but how different it would be from working on your idea, pitching it etc?

Why not opt for work of your choice in a big tech giant? Win-Win and even to win at startup lottery, eventually you need to reach the win-win stage!

My spouse worked at a ~150 headcount (c round funding) tech startup and hated it.

She now works for a massive revenue, mid-size firm and ... mostly hates it.

At one time in my life, I worked for a company that would have been considered a tech giant of its time (one of the 100 most profitable firms in the US at the time), and it was OK-ish.

My opinion is that I would do it, if I had the opportunity to do it. If you can afford to take the chance now, then consider taking the chance now. You never know if you will be able to do it in the future.

Creating a startup is very tough, If you have a great job I'd be careful. If you can I'd try to do something small as a side project first and see how much money you can make. A lot of people here are good coders but have no clue about business, if that is you tread carefully.

It also depends on how much experience you have. If you've been working 1-2 years I'd say no way. 5 years: maybe.

But as others said its good to do when you're young. Combined with living in Thailand or something sounds great.

That sounds cool. A fair idea. Working on a side project, validates it and then take a decision based on that. Experience also plays a major role.

The problem here is the dilemma when to go full-time. Its always a tough call. Compared to a side-project building up a scalable business model is a different ball game altogether. So brace for that once you go full time everything changes and without going fulltime you'll probably reach nowhere

What's a good filter for knowing when to go full-time? Covering your monthly expenses?

I have a consulting business that pays me handsomely. But I also have a side business that has paid for my monthly expenses the last 3-4 months. Would that be a good metric to jump ship from consulting and go full-time with the side hustle?

Yeah, that sounds fair. But there is a small caveat here thou. The income from side projects are so volatile, sometimes you can't predict on them. You can only make them stable if you invest enough time on it and study the usage pattern. And most of the time you'll have to get on full time to get those metrics. So we will get back to that chicken and egg problem again

Entrepreneurs that go to Thailand to start a startup are mostly digging their own grave. Talent may be everywhere, but opportunity is not. I have met a couple of founders that moved to Thailand that didn't make anything of themselves. They mostly went there for a cheap living and ended partying most weekends. I would advise against starting a startup in Thailand.

Worked in a dozen start ups and all but 2 still stand today. Going from startup to big tech is hard because there's a process you will need to follow and the work may not always be exciting. But the pay, bonus, options make up for it. Going from big tech to start up is easy when you have a nest egg built up. If you don't it'll be a major struggle and it's not worth it to be honest.

I left a big corp job in Silicon Valley and returned to India to work on a startup. I must say that even though I am poorer in terms of $ earned or net-worth, I can honestly say I am happier.

I wrote an article recently about my leap of faith and four pivots. The link is in my bio.

Depends on the type of person. For some it’s the only way to have a sense of control over ones own destiny. Others who lack the discipline to always be selling and pushing forward are better off sticking to their current role.

My recommendation would be to be very clear on the opportunity-cost, and be ready to share that burden and risk with an investor.

I think people lazy enough to ask a question like this are not suited to entrepreneurship.

Why is it a binary? Can't you launch and see if there is any interest? You

If you have to ask, you should probably stay at Big Tech Giant.

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