Ask HN: anyone leave a high paying job to work at a startup?

I didn't leave a high paying job, but I did turn down a high paying job offer from Google. My consideration wasn't "will this make me rich"; rather, it was "can I make enough money in the long term doing this that I won't be dramatically worse off".

I suspect that for most people the calculation comes down to some version of "what's the most interesting work I can do while still having a reasonably comfortable income".

I've turned down very good offers to stay in startup-land. But you're right: given success rates and the upside exposed to non-founders, it's not a great move.

Start something small on the side. Fix your personal finances so you can build up a warchest (it's easy: just live the lifestyle you're considering living as a startup employee). Then, in a couple years, go work for yourself.

High paying is relative but after doing the calculations of joining a startup with ≈15 employees the possible upside was really low when compared to benefits such as stock options, employee stock purchase programs and 401k matching.

I realized the the upside really exists for the founders...so that's what I'm doing.

I left a great well paying job at TripAdvisor for a startup. It was definitely a hard decision and I don't know which way it would have gone had I not gotten into YC.

Had my job offered to double my salary or something rediculous like that I probably still would have left, but coming from a middle-class family where having a high paying job was a major motivator (for the stability, not the luxury), it would have been a very painful thing to do.

yep, i did. i found out that you go from $ to 0. And it's very hard to make the first .01 cent. But you will learn a lot, so take it as having fun for a year and learning more than you learned in Univ. and you will be ok.

Actually I wish our profession wasn't just 0 or big chance payout but had some in between too.

You probably won't get the same pay to work at a startup as you would get at a bigger company. However, I currently work at a startup and I wouldn't consider myself destitute. Just because you're working at a startup doesn't mean you'll have a low standard of living.

If salary is important to you, I'd recommend a later stage startup. It will likely be the happy median between an early stage startup and BigCo.

I left a well-paying gig but left knowing 3 key things:

1. Had a solid financial cushion via savings to really give myself enough runway to do the startup thing sincerely and whole-heartedly

2. Knew that if even things blow up, I'd always be employable

3. Very few folks become really wealthy working for someone else

The upside monetarily is a motivator, but the bigger thing I've realized after jumping to startup-ville is that my worst day in my startup is honestly better than my best day in corporate America. There are immense non-monetary benefits (and a whole lot more stress as well)

I wouldn't call my previous job "high paying," but it had a good enough salary. I could've stayed for years and save enough to live a good middle class life.

I've since left and joined a startup, I'm making slightly less and with less benefits but I'm definitely having more fun and learning 10x as much working in a small very early stage startup versus a corporate 100+ year old company.

When I was in middle school, I left my usual clique of friends to be in the "Abercrombie & Fitch" clique. Reasoning that being popular would expose me more to cooler people and prettier girls.

When I was in high school going over college, I decided to go to a school based on its prestige over the school I fitted in. Reasoning that a school with a better name would help me get a better job and impress people when I go to dinner parties.

When I was in college, I decided to chase girls that I can't have and break off with girls who I clicked well with. Reasoning that I should get what I can't have and that most people will judge me better with a good-looking girlfriend.

When I'm working, I chose to work at a well-known Wall St. company over a unknown startup. Reasoning that the compensation and the cocktail impression factor would be better this way.

Like a trader, everyday people make choices. Some people choose to play it safe their whole life, stay, work, marry & die in the same town that they were born in. Some people take incredible unwarranted risks, like dedicating their lives to be a professional athlete/musician/actresses despite overwhelming evidences that they don't have the talent for it. Some people take huge risk by letting themselves emotionally vulnerable when they fall in love. Some people follow the most optimized investment plan, go to the right school/major, work at the right company, choose the right partner, put the right contribution into one's 401(k) plan, have the kids and then retire the right time and finally die the right way.

But the market is simpler than life because in the end, everyone's measuring stick is the same, how much money you made/lost. But in something vague as life, everyone has different measuring stick; what's even more frustrating, your own measure stick is constantly changing; what I thought was important two years ago is completely trivial to me now and vice versa for what I thought was trivial.

And there's no use in predicting what you think would be important to you in the future because you most probably end up being completely off; plus, it'll just leave you frustrated to forgo your present moment to work towards a future that you might discover that you won't want anyways. Attribute that to any philosophy or psychology B.S you want (cognitive dissonance, confirmation bias, existentialism), all I know is that it has happened and will happen again.

The only certain I'm certain about is the present; I'm not talking about being hedonistic, but to take risks for the present and to leave the present moment without any regrets. Kiss the girl, stay up late to finish coding & take the day off just to take a walk.

I did - and this is in India, where "high" isn't really all that high to begin with.

My thought process was pretty simple: at the time, I was more or less independent, and living /very/ frugally, which made the decision easy. I do know this: if my financial needs were different, I wouldn't have moved.

This just boils down to "what are you looking for in life?"

18 months ago I was at a "high paying job" by most standards. I worked 45 hours a week, had great coworkers, and even generally enjoyed my work.

I left because a regular job gets in the way doing other things that are important to me: enjoying the sun in the middle of the day, not working on tuesday if i don't feel like it, traveling for 3 weeks at a time, etc.

Being incredibly rich or owning shiny toys isn't nearly as important to me as scheduling freedom (and hopefully eventually location independence), so it wasn't for me.

Sure, it'd be great if I somehow had a big payout for doing what I'm doing now, but its not even in the top 5 factors for why I chose to pursue "the startup route".

No amount of encouragement or advice from others who have left their jobs will help you decide if its the right choice for you. You have to dig deep, figure out what you ACTUALLY want, then you can decide if leaving the day job is right for you.

throwaway account: When I left my job a few months ago, my total income from my employer to that point this year was over 400k. It includes payouts from my last startup I sold, but this would have continued for the next year or so had i stayed.

Since this is a financial article, I'll focus on financial stuff.

Its anecdotal but I think the average financial return for doing a startup is slightly better overall, and probably decently better if you are highly intelligent and skilled overall.

If you are not highly intelligent and skilled overall its possible working at a company is a better deal.

Two questions to consider:

Q1: Long term--what will open up more avenues of opportunity for me?

In general I was not a very good corporate climber. Some ppl are. Some ppl aren't. I am not. I dress casually, speak colloquially and comparatively don't care too much about what other ppl think and don't like 9-5.

Given I already have startup success, it was easy for me to decide startups are financially more lucrative for me.

Why didn't I stay and wait for all my earnings to pay out?

1. I got most of it already

2. I'm not getting any younger

3. I found a great team that I wanted to start a company with.

4. The remaining cash would not change my life significantly.

Given all of that, I decided I'd rather leave.

Q2: Having been in your position when I was a bit younger and first starting out (relatively high paying job...didn't love it but i wasn't going to shoot myself), I'd ask myself the "bezos/jobs question" : When you are 80 and on your deathbed, your life flashing before you in your last days, will you look back and regret the decision you took to jump ship and do a startup?

Imagine all sorts of realistic worst case scenarios....completely flops, you go bankrupt, waste 3 years of your life, gf leaves, mess up your health for a while...whatever is really bad but realistic.

Does the 80 yr old regret the decision of doing the startup? If so, then thats fine. Don't do it. I think I would have balked if I had a mortgage, kids and no savings.

However, in general people regret things they haven't done more than things that they did.

I'll provide a counterpoint. I have a corporate job that pays pretty well and I am very happy with it, to the point that I wouldn't consider leaving it outside of a ludicrous offer. I love managing people and complex projects involving wide variety of variable inputs. I love a global organization. I am enthralled with coming to work everyday and being able to pick any number of opportunities for a) improving people's lives, b) streamlining business process, or c) creating new business opportunities. I'm only one step removed from CIO and I have a boss who encourages me to run my org (currently 60 people) like a startup. I am encouraged to learn about customer development, cutting edge technology, business law (mostly contracts at this point), and all sorts of semi-random business processes. I love the chaos of it all, and I especially love that I am trusted enough to be autonomous. I feel like I'm running my own little company... that just happens to be inside a Fortune 200 global mega-corp.

Jeff Bezos is a great example of someone who had a high-paying job, but quit to go create a startup (Amazon.com).

"...and the framework I found which made the decision incredibly easy was what I called -- which only a nerd would call -- a "regret minimization framework." So, I wanted to project myself forward to age 80 and say, "Okay, now I'm looking back on my life. I want to have minimized the number of regrets I have." I knew that when I was 80 I was not going to regret having tried this..."

- quoted from http://www.achievement.org/autodoc/page/bez0int-3

From my answer on Quora (http://www.quora.com/What-made-you-quit-your-comfortable-sal...)

Jeff Bezos' Regret Minimization Framework:

"...it really was a decision that I had to make for myself, and the framework I found which made the decision incredibly easy was what I called -- which only a nerd would call -- a "regret minimization framework." So, I wanted to project myself forward to age 80 and say, "Okay, now I'm looking back on my life. I want to have minimized the number of regrets I have." I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed I wouldn't regret that, but I knew the one thing I might regret is not ever having tried. I knew that that would haunt me every day, and so, when I thought about it that way it was an incredibly easy decision. And, I think that's very good. If you can project yourself out to age 80 and sort of think, "What will I think at that time?" it gets you away from some of the daily pieces of confusion. You know, I left this Wall Street firm in the middle of the year. When you do that, you walk away from your annual bonus. That's the kind of thing that in the short-term can confuse you, but if you think about the long-term then you can really make good life decisions that you won't regret later."

See: http://www.youtube.com/watch?v=jwG_qR6XmDQ

A big payout is definitely a large factor in jumping ship if you're arrogant enough to believe that you can attain such a thing. If you just want to "work at a startup" without having much of an idea about which startup and no intention of starting one yourself, then frankly in my opinion, jumping ship isn't for you. If you're this concerned about your financial status today, at a company you don't drive the vision for you're going to find it harder to drum up the ambition and drive it takes to get through times where a huge financial payout is not as certain.

OK, the goal is independent wealth: a low risk passive income. The math for this is pretty simple.

Say you are a rock star making $100k/yr. After taxes, in CA, that's ~$60k/yr. If you are single and super-cheap (i.e. celibate), you can live acceptably on about 30k. Thus, you build 30k/yr in capital.

Say you need $3k/mo bare minimum, pre-tax, to retire, and refuse to draw down on capital. At a 5% return you will need $720k. It will take 20+ years to get there, assuming you survive as a corporate cog for that long, which is unlikely, given competition from emerging markets.

Of course, if you ever get married and have a family, this won't work at all. And if Wall St somehow takes 30% of your portfolio one year, you are in serious trouble.

Now, instead, say you quit working for The Man, and build a service priced at $10/mo. You have the tech background already, and work hard to learn the necessary ops, marketing, sales, and other skills. You automate everything. You work from home (saving 1 hr/day commute), have excellent margin, no employees, etc. With a web app, to hit $3k/mo, you probably only need to average 400-500 paying customers.

There are several billion people on the Internet. You just need 500.

Sure, a business producing $3k/mo after expenses is not exactly equal to having $720k in liquid investments. It's much less liquid, requires more of your time, faces competition, etc. But it also has some advantages, such as the potential for very rapid growth.

Most importantly, it scales: you can build more than 1 app. So even though you'll probably fail a lot before success, you're probably still better off.

I wish somebody told me this 10 years ago.

I left a high paying job two weeks ago mid-project to start a start-up. I did it because each day in that cube I cared less and less about money and more and more about freedom. I spent the better part of the past two years making my company over 7.6 million in just six months, and actually much more over the full two years.

I needed to create and to be rewarded for my efforts fully. Everyone I know was against it, wife, family, and friends. Thought I was throwing away something they could only hope for. At the end of the day we live once I'd rather be poor and happy trying something I always wanted than stay in that cube always wondering.

What prompted my move so abruptly was interviewing a guy for a senior position. We asked him what his ideal job would be, and he gave an answer of doing his own business. He excused it as a dream because he has kids, and that's when I realized everyone I worked with had the same reason for not just doing it. That's when it snapped in me.

Week later I put in my notice. No jobs no nets to fall back onto. I actually worked on my own project last week and it was heaven. I have a meeting for a three month contract next week to feed my funds to continue this dream. Brother this has been the best two weeks of my life.

Keep in mind that however much people talk about startups as a shared mission or a calling, it's also about the money. Try asking for a meaningful chunk of equity if you want proof. The goal of every startup is to reach an exit, which is an acquisition 99% of the time. Once the retention agreements expire a year or two later, the newly-enriched founders will be gone while the employees will watch the acquirer systematically dismantle the company. Or they'll be laid off.

This is a business; don't get too romantic about it.

I felt seriously underchallenged at my day job, even though I was making six figs. It was quite a difficult decision, given the fact that you hear horror stories about people not able to find jobs in the current economy. However, what it came down to, for me, was I was just wasting my time at my day job, and after awhile I realized that time and my sanity was my most precious commodity.

You say there are a lot of risks associated with a startup. As part of my decision process, I realized I had to consider the long-term risk of being unfulfilled at your job, not developing your skills and talents the way you expect. This is a bigger risk IMO.

Yes, and the high-paying job I left was at a big company that acquired my previous startup.

Post-acquisition, the salary was good, the bonuses amazing, but the company was dumb as a bag of hammers, and the job became soul-crushing. Dilbert bosses, communication by powerpoint, pointless projects. It got to a point where I just had to get back to a startup. All but one of the really early employees left for similar reasons, and also to join startups again.

That said, I'm not sure I'd make quite the same decision if I couldn't get in very early to a startup that I thought had a really good chance of succeeding.

You may want to read this, written by an Indian so more in lacs and rupees than in dollars and millions. But you would get the point. http://www.pluggd.in/why-work-for-a-startup-297/

My suggestion:

if (there is a very promising good startup offer): take it else: work on your side project until it takes off as a real startup

speaks, are you trying to find a rationalization to stick with what you're doing?

the whole 'fun' thing has two aspects.

There's the practicality aspect i.e. business in general and startups in particular are painfully difficult and you can't really win if you don't like (or ideally love) what you jump in to.

If you can work only 8 hrs a day but your opponent loves his work and words 14 hours a day you're screwed.

There's also the reality aspect. NO ONE ever does a start-up without motivations like money and pleasure and importance.

If your prime modality is making money and comfort then a start-up isn't right for you at all.

Also, all your reasons for wanting to do a start-up are meaningless. stepping stone to other opportunities?

if you're taking such a big risk fucking do something that is the ultimate opportunity.

I did not leave a high paying job to start my own company but I rejected an offer and didn't collect others before I started my own company directly after finishing my studies.

I have a double Masters in Business Administration and the "traditional" way for students like me is to start as a consultant (McKinsey and the gang), investment banker or whatever. In Switzerland that meant a starting salary of at least six figures but money was not really a factor in my decision it was mostly based on the fact that I wanted to do what I liked.

In the year between my Bachelors and Masters degree I interned 6 months for a Swiss web/technology consulting company and 3 months for Accenture. Both experiences bored me to a degree I had not thought possible. It wasn't that I had no responsibility - which I had - or that the tasks were repetitive - they were only slightly - but I just wasn't faced with the challenges I was looking for. From quite early on I loved to create my own things and I realized that just was not possible in a corporate environment and I had to do something about it. My first plan - following conventions - was to be a part-time entrepreneur. I wanted to work at one of those strategy consulting companies and have my own thing on the side. When I look back that idea seems crazy but at that time I was convinced I could do both. But in March I talked to a successful Swiss Entrepreneur and he convinced me that this is an all or nothing game. Either I went all-in or I had to fold. I decided to go for it and haven't looked back.

As I said before money wasn't really a factor in this decision and that is for a few reasons:

1. I have a safety net through my parents. This obviously is a very comfortable situation that not everybody has.

2. I looked at my potential salary as opportunity costs and decided that it was worth the costs that I could do what I wanted.

3. If I need to I can still go work for those companies I decided to forgo now or another company. I have an excellent education and I see my entrepreneurial endeavors as an extension on that. Obviously after having been an entrepreneur for several years I probably won't fit into the mindset that Strategy consulting companies look for but there will be plenty of opportunities if need be.

4. I never had massive amount of money available to me. I always lived comfortably and still do but I was never a big earner and therefore don't have an expensive lifestyle to support. Also at the moment I don't have any responsibilities, no family, no children to support.

On a side note: The consequences of my decision to start my own business have not always been easy. One of the harshest things is that many of my friends now almost can swim in money but once I talk to them about their Job I am convinced to have made the right decision.