
Ask HN: Do you regret leaving corporate for entrepreneurship? - ryeguy_24
With all the benefits at a corporate job I still want nothing more than to be out on my own and start my own SaaS business.<p>Has anyone left a great corporate job for entrepreneuriship and regretted it?
======
drenvuk
I have said this before in other topics when someone is getting fed up with
their job and want to try their hand at making a company. Get the business
started, running, profitable and automated (with humans, bots, or scripts) and
then quit. Do not remove your major source of income which also happens to be
your major source of investment and start the clock that runs until your bank
account empties and you need to look for work again. It is not a good idea to
kill your company's lifeblood.

The added pressure and energy drain from working on your own machinations
while working a full time job pales in comparison to the added pressure and
energy drain from working against the clock. In my case it became a source of
depression and a constant demotivator when I realized I was running into
roadblocks. You cannot foresee all of the difficulties you will run into, you
cannot rely on stories of other entrepreneurs doing so. They are half truths
and tell only the triumphant side of it, ignoring the failures of the hundreds
or thousands of others who's companies made it only to the paper stage then
died with a whimper, much less being in the spotlight of the medium and
techcrunch and online news articles and forums. You're hearing about certain
entrepreneurs solely because they're outliers, not the norm - they're a good
narrative.

Keep your job. Make the product. Make connections. _Get Customers_. Then make
the company. Not the other way around. If you're the one in a million already
has the connections and skills to make it happen then more power to you but
statistically speaking, you probably don't. You should acquire those qualities
with gusto but also with prudence.

Good luck.

~~~
beat
This. Yeah, I made that mistake. On one hand, working on building a company
full-time was the best time of my career. But it failed, and I lost a lot of
money in the process. And going back to the corporate world was...
demoralizing.

(As an aside, I think the biggest problem I had was lack of a committed co-
founder. I had help and support, but it's not the same. Later, I tried pushing
again with potential co-founders, but they got distracted and lacked
commitment when I really needed them.)

edit: I do plan to get back to it soon. I'm taking a forced six month hiatus
to reset that concludes in July, and I'm kind of chomping at the bit for it.
But only while doing my dayjob too! Not going to leave that again until I have
paying customers.

------
_5meq
I'm a dev.

I did this a few years ago, started my own company.

I failed for two reasons:

1\. I wasn't experienced enough as a developer IN THIS TECHNOLOGY to hit the
ground running.

When you are self-employed, time = money. You don't have time to learn the
technology, figure out your business, and write the code. You have to hit the
ground running and burning time on ramping up is extremely expensive.

2\. I lacked the discipline required to maintain myself while working
extremely hard at my start-up.

Additionally, I didn't take good enough care of myself. I was ignorant about
how to be productive. I was working all of my waking hours, martyring myself
for my start-up and then getting up the next day and doing it over again.

Here's a tip: This is bad and leads to failure if you aren't careful with your
time, food, and sanity management. A lot of people like to glorify this
behavior but really, excellence is a 24-hour job.

Working out, eating well, getting a good night's sleep, and then coming into
work the next day with clear-eyes beats running yourself ragged with panicked
late-night programming sessions every time. ( Although, some people like to
work at night and that is totally fine, we all have our own form of
productivity. )

My point is really more about taking care of yourself and BEING DISCIPLINED.
Unless you are wealthy, you do not have time ( remember, time=money ) to make
mistakes. Discipline is your buffer between your degrading sanity and your
ability to make good decisions.

~~~
carlsborg
Developing this cadence takes deliberate effort. Same for remote working when
you are a few hours ahead of the main team. Remember to pack it up when you
are done for the day !

------
Meekro
I left my "real job" for entrepreneurship about 8 years ago (at age 23) and
haven't looked back. I've run several small companies since then, with a game
server host[1] being the most recent.

I'm pretty happy with how it's gone and I have no regrets over leaving. I was
happy and well-treated in the real job, but nothing beats the freedom to work
on what I want, when I want, using whichever technologies I want.

The biggest downsides for me:

1\. Fewer opportunities to meet and collaborate with other nerds. I love
working independently, but "argue with smart people" is a great way to refine
your ideas. I wish I had more of that.

2\. Fewer opportunities to learn from larger companies. Many companies have
internal technologies, tools, processes, shell scripts, etc. that are truly
inspired. Former employees get to take these ideas (though not the code
itself) with them when they leave, to apply to future jobs or to their own
startups. The more time you spend in the corporate world, the more of these
tools you accumulate in your own tool belt.

[1] [https://indiehackers.com/businesses/arkservers-
io](https://indiehackers.com/businesses/arkservers-io)

~~~
sodafountan
This is great advice. Did you work on your first business part-time while
working your last "real job"? I feel like I'm in a similar boat and I'm not
sure what to do next. I'm 24 and I work for a great company with really smart
people whom over the past two years I've learned from quite a bit, I've always
wanted to start a business though, actually in college I did just that to earn
money. I created an app development business targeting Windows Phone and was
able to build a pretty sizable passive income stream which kept me satisfied
throughout college. I'm now debating finding a new job but really what I'd
love to do is go back to entrepreneurship, yet on the other side I know how
valuable learning from people in the industry actually is.

Any advice?

~~~
Meekro
I started my first business while I was in college, and kept it going on the
side while working the real job. After a year at the real job, I decided to
leave and focus on the business.

What happened to your company from college-- did you shut it down? Sell it?
Did it die on its own?

I don't think anyone can tell you whether it's the right time for you. Neither
decision is permanent, though: If you do leave and it doesn't go well, it
shouldn't be hard to go back to your old job or find a new one. "I took a year
off, started a business, learned a lot, failed, and now I want a job" should
go over well with most employers. If you don't leave, you can spend the next
year learning more from your employer while tinkering with your idea on the
side -- and then leave next year.

As you age, you'll tend to accumulate obligations. Marriage, kids, mortgage,
elderly parents/relatives that need care, medical problems of your own --
things like this will make it harder and more risky to quit your job later in
life. So if you're going to do it, your 20s are a great time.

~~~
sodafountan
I appreciate the reply,

My business kind of evaporated given the ever decreasing market share of
Windows Phone. I was able to carve out a pretty nice little niche where I
created small apps for Windows Phone in even smaller targeted niche markets
where there was usually almost no competition. (I built Workout apps targeting
specific exercises, I built small little games that were popular on iPhone and
Android but never got ported to Windows Phone, alarm clock apps, I created a
piano app that did really well, things like that) given the sparse selection
of apps on Windows Phone most of my apps did pretty well with no marketing
whatsoever.

I tried to pivot to iPhone and Android and saw a bit of success on Android but
the business model didn't really translate to those platforms given the
oversaturation of the app store, I saw my revenues dwindle down consistently
and by the time I landed my first job two years ago my passive income had
dropped to about 500 dollars a month, it's now completely gone, nobody uses
Windows Phone anymore.

I am working on a much bigger app now targeting iPhone and Android, but the
app market is tough to penetrate. I guess the only path for me going forward
is to either stick with my current job that I know well and put in more work
on the app, or look for a new job where I can learn more and earn a bit more
but my responsibilities will most likely increase and I'll be forced to learn
a new tech stack which can take a toll and could affect my ability to work on
the app in off hours, I've been working on the app for about five months now
and I really don't want to lose my momentum.

Anyway sorry for the rant lol, that's my predicament. I agree I could always
go back to the workforce if anything goes awry but I'm not even at that
decision yet, it's more a question of how do I allocate my time properly until
I become profitable enough to make that decision, and how long do I put off
moving my life forward given the uncertainty of the app market.

------
scrollbar
I've hacked away on projects over nights and weekends, hoping that one of them
would be my ticket to a self-led lifestyle, but with no success. Then I landed
a contracting client, and quit my job to commit fully to the client. I took
the chance! Six months later, I was fairly burnt out on working alone with
this client. In retrospect, I wish I had kept the client and tried to grow the
business, even if reality wasn't as rosy as I had hoped.

Since then I've tried to find more clients and not had much success, after
taking a job and then quitting again. Looks like I may end up back in the
corporate world soon enough.

So- no regrets from this attempt to find freedom, even though it's leading me
back to where I started. I will say it's become clear to me that our
socioeconomic system is not set up to support people becoming more free...
quite the opposite.

Maybe if you try to make a SaaS business into something that requires VC-style
scaling, it could backfire and cause regret, as you're committed to something
that becomes more all-encompassing and lasts many years.

------
overcast
What's wrong with working the corporate world, and moonlighting your SaaS
business? If it ends up taking off, then quit. I don't understand why it has
to be either or. I run multiple side gigs, while keeping the safe corporate
job, for now.

~~~
aardvark291
If your side-project is at all related to your day job, this most likely runs
afoul of your employment agreement and IP considerations. Typically, your
employer claims ownership of all IP you generate that pertains to your work or
its business. For example, if you work at Google, I think it's essentially
impossible to simultaneously work on any other side project that you wish to
commercialize that will not be owned by Google.

~~~
overcast
Baloney, unless you're using corporate resources to get it done, they don't
own work you do outside of working hours. No judge would ever uphold that.
There are tons of Google / Facebook / whatever employees that build software
outside of work.

~~~
tokyodude
That's not my understanding.

At least in California AFAIK the law says exactly what the poster above said
which is that the company owns work related their area of business even
outside work hours and not on company equipment.

I always think of it this way. You're at dinner (ie, off company time). While
a dinner you think of a solution for something at work. Do you own that
solution? Can you charge the company $$$$$ to sell them this solution you came
up with outside company hours?

If yes then there's an incentive for you to never think on company time. If no
then it seems pretty clear there's a spectrum from clearly related to the
company's area of business to absolutely not related to the company's area of
business. If you work at Facebook and on the side you design a new IoT coffee
maker that's probably on the unrelated side. If you work at Facebook and on
the side make a new social networking site probably on the absolutely related
side.

If you want to be safe rather than wait for a court to decide get it in
writing. At least when I was at Google they offered that service. You could
bring them the idea and they'd tell you if it was related or not and if not
give you a signed contract saying they officially had no interest in your
outside project.

------
a13n
Heck no I don't regret it.

Just over three years ago I left my cushy job at Facebook to start a company.
It took a year and a half of grinding to make our first dollar. Now we're
ramen profitable and still growing strong. [1]

The reason it took so long is because I was an inexperienced founder. I could
build the product, but stuff like getting customers, pricing our product,
writing a landing page... These are not things that software engineers at big
companies have to worry about. It took years for me to pick up these skills,
and I'm still learning loads.

And I'm so glad I learned them because now if I started all over again, it'd
take a fraction of the time to build something successful.

Now, different people are different. If you really love solving technical
problems and don't really care about sales/marketing/business, being a founder
might not be right for you. If you have a low risk profile, or care a lot
about work/life balance and comfort, big companies can be great for that.

[1]: [https://canny.io](https://canny.io)

~~~
riku_iki
> I could build the product, but stuff like getting customers, pricing our
> product, writing a landing page...

It would be extremely interesting to read what lessons you learned on this
road :-)

~~~
a13n
Ask and you shall receive!

[https://canny.io/blog/saas-startup-ramen-
profitability/](https://canny.io/blog/saas-startup-ramen-profitability/)

[https://canny.io/blog/lessons-learned-bootstrapping-
saas/](https://canny.io/blog/lessons-learned-bootstrapping-saas/)

~~~
riku_iki
Oh, thanks!

------
mlthoughts2018
I greatly regretted leaving a finance job early in my career to work in an
early stage start-up.

The start-up workplace culture was worse, work life balance was worse, the
loud open-plan office was unhealthy, distracting and frustrating to work in.

Even on a generous expected value basis, favoring only high valuation exits or
IPOs, and even as a super early stage employee, the compensation was way worse
at the start-up compared with a stable high salary, bonus, retirement plan,
and benefits.

To be clear, that is even if you assume away a lot of the risk for bad
outcomes at the start-up and favor high valuation possibilities. Even still,
the equity is manipulated by founders and investors and is so drastically
unlikely to work out in a favorable way for employees.

------
cgopalan
If you want to hear a "yes, go for it" then yes, go for it.

If you are still open to suggestions, lets play out that scenario where you
quit your job and start a business. Then you would: 1) Make an overall vision
for your business. 2) Translate it to several phases. 3) Translate each phase
into tasks. 4) Start working on tasks. If a task is too big, break it down to
subtasks. 5) Incrementally start finishing tasks.

Now, can you do the above devoting an hour or so each day to it while being in
your corporate job?

~~~
optymizer
(skipping over legal and tech arguments for a moment)

Sadly, if your business is in software, then your corporate employer will own
your IP, and the answer becomes "No".

~~~
shawn
Not a chance. If someone wants to hire me, they do not own my work outside of
business hours. It's the new serfdom.

~~~
optymizer
The fact is, lots of software devs, aside from you, are employed by the large
tech companies, and depending on the state, the courts side with the company.

I wish we could all collectively refuse employment, but once you get the
offer, not everyone has the luxury of saying "no, I'll go with a much lower
salary at a smaller company".

------
deepaksurti
You won't regret it if you go to entrepreneurship and ship.

The problem is not about entrepreneurship but in not planning for failure and
having backup plans.

John Carmack: "There is wisdom that only comes from complete product cycles --
no amount of job hopping can provide it." [1]

From personal experience, I can say go for it not because you hate corporate,
but because you want an end to end experience, then come back to an even
better role, better pay cheque corporate job, if the gig fails but you have
shipped and have good landing zone on failure (some months with expenses in
bank mainly). HTH.

[1]
[https://twitter.com/id_aa_carmack/status/761986843319660548?...](https://twitter.com/id_aa_carmack/status/761986843319660548?lang=en)

~~~
nikanj
Nothing worse than shipping and having absolutely no sales.

~~~
gschier
Not true. Not shipping at all is much worse. Shipping and having no sales is
how every business starts. The next step is learning WHY. Talk to people,
iterate, and repeat. That's business.

------
deweller
Having a paycheck and being an entrepreneur is not an either/or proposition.
There are things in the middle.

You can find a well-financed co-founder and get a commitment for a paycheck
for a fixed length of time (1-2 years). You will probably receive less equity
in this situation, but you can still get enough equity to feel like a true co-
founder along with enough of a paycheck to not be stressed about making ends
meet.

------
squirrelicus
In August I quit my cushy (cushy!) day job to go full time on my startup,
fully bootstrapped, living on my savings account.

I discovered what panic attacks were, and made it to February a few months ago
before getting a less cushy day job. Although I had the financial runway to go
longer, I didn't have the mental fortitude to keep it up with a wife and three
kids I have to provide for.

We're still continuing nights and weekends at a much slower pace, but at a
much more sustainable pace. The biggest challenge is keeping a moonlighting
team motivated. My decision to fully vest my cofounders up front is paying off
with this approach. I suspect it will be another 6-12 months before we go live
at this point.

------
wenbin
I don't regret. I left my day job in late 2016 and started to do this startup
thing. I'm still very happy.

I've seen people who left day job to start companies and became very unhappy
very quickly (within 6 months). The key thing is to have the right motivation
and to manage expectation.

If the primary reason to start your own company is to look good in front of
your other fancy friends, then you'd better not do that in the first place.
Doing startup is roller coaster. You won't look good in front of others all
the time. Actually, for a long period of time (many months ~ many years), you
may look pretty bad, in terms of product metrics, income, company
reputation...

Some of my friends asked me whether they should start a company, I typically
suggest them to answer these questions first:

* Have you made over $10k on your own? Not from your day job salary. Not from public stock market. Making money needs practice. You start a company to make money. You'd better have some experience of making money first.

* What's your longest project? Have you worked on anything for multiple years? Grit & patience need practice. Building a successful company takes multiple years, even decades. Be prepared.

* When was the last time you were insulted by others? If you grew up in a very comfortable environment (rich family, great schools -- because your parents went to those great schools too, great companies, ...), probably you already get used to compliment for your entire life. Now you are going to face very very diverse set of people who don't know your family background or don't recognize your family name, if you start a company. If you are the kind of people that are easy to be upset, you'd better stay in the friendly corporate.

* What happened when you broke up with your ex or your friends? People relationship is complex. You'll experience a lot of bad people relationship if you start your own company -- breaking up with cofounders, firing employees, fighting evil investors, fighting con man, fighting bad reporters, dealing with malicious users, dealing with competitors (sometimes in person)... All kinds of drama. You'd better practice this kind of things before starting your own company.

~~~
majkinetor
Nice points m8.

------
glancast
I started a SaaS business, which is now my full-time gig -- I would say don't
leave a job until you have something producing a ramen-noodle level salary for
you. When I was able to pay myself $2,000/month it was enough to live on for
my situation at the time. I was working 80 hour weeks in my underwear,
scrambling to answer support requests, fix bugs, and move the codebase
forward. If I had to do that while also trying to find product-market fit and
worrying about running out of money, I might have broken down.

No regrets with my decision now. Once my business slowed down (read: I
automated much of it), I actually went back and spent two years at a startup +
1 year contracting to bring in some extra money and get new experiences. The
extra cash was certainly nice, I used it to setup a nice start on retirement
and buy a house. Ultimately, though, my hatred of corporate politics and
building wealth for the capital class without equity of my own led me to re-
focus on my SaaS app. I've been enjoying the freedom and challenges ever
since.

------
grosjona
I went back and forth between corporations and startups. The money and hours
are way better when working for a corporation; especially if you manage to get
a contract position with a high day rate.

But I've realized with time that I'm just not built for the corporate world so
it's not even an option for me anymore. After 6 months working for a
corporation, I feel like shit and I have to quit for my own mental health.

After working for startups for a while and taking risks all the time, I'm no
longer the same kind of person as the typical corporate office worker and it's
hard for me to fit in such environment.

If I didn't have better options, I would probably do contract job hopping from
one corporation to another every 6 months... I did that for a while and it
gave me a certain feeling of control over my life which made me feel kind of
like a one-person startup.

------
slipwalker
How about the other way around ? Leaving entrepreneurship in order to take a
corporate job and not looking back ?!... a bit of history: just around college
( 1996-1997 ) with the internet boom in brazil, i took my first consultant
clients, since then worked with several "fintech" ( wasn't called that by
then, but that is what those companies were/are... ) and tried to grow my
company ( software consultancy and tailored code ). But being a tech
entrepreneur below the equator line is not for mere mortals ( crony capitalism
everywhere, labor and tax laws very fluid and incomprehensible by most
professionals, terrible and costly infrastructure... ) so, last year i gave
up. Took a corporate job writing code on a multinational corporation (
gargantuan enough to have access to the juicy contracts, contacts and clients
) and now i have a paycheck every month, in exchange for just 8 hours a day of
my life. Before, it were 14 to 16 hours a day, plus weekends, no payed
vacation, no time left for my family, and most months ( after payroll and
taxes ) there were no money left for me...

~~~
nikanj
I've seen people pre-exit startups. Be one of the founders, take a corporate
job as soon as the initial vesting is complete and the business has solid
traction

You're basically gambling that the other founders won't scuttle the startup
just to spite you. This way, you get to enjoy the possible lottery winnings
from the startup eventually making it big, while simultaneously having the
safety and comfort of a corporate job.

------
danni
Not leaving a corporate job, but slowly transitioning from freelancing to
working on my SAAS business
([https://www.scraperapi.com](https://www.scraperapi.com)) full time. I'll
throw out the suggestion that maybe you should seek a bit of freelance work on
the side so you can have some level of income while you work on your business.
Even if it's just 5-10 hours a week, if you can get $100/hr from someone for
that you can cover a large portion/all of your living costs if you live
frugally. Good luck!

------
godot
I did this. Left a cushy corp job a few years ago, then worked on my own
startup for 3 years. While we had some small funding, we could only pay
ourselves very little salary (almost below livable standards for bay area,
cutting into savings a little monthly), and in the end it had to shut down
after 3 years. Went back to regular job (non-corp, an early-mid stage startup)
after that.

I think the _only_ factor that I have regrets about was financially. Not so
much about having to cut into savings because I had good enough cushions
anyway, but just realizing that I could've had 3 more years of high pay and
stocks and padding the investment account with more money, and putting myself
3 more years away from retirement (or maybe more considering compound etc).

Other than that, entrepreneurship was an awesome experience that I wouldn't
trade for anything else really.

------
adamnemecek
I quit my job to work full time on something I’ve been wanting to do since I
was like 12. It’s been like two years now, mich longer than expected, but
there was a lot of shit I had to plow through, the project is more researchy
than I thought. I don’t regret it whatsoever, what I regret is stressing
myself over launching ASAP in the first nine months of this thing, which
really caused me to burn out. I would never take time off cause I thought I
was wasting money, but it’s impossible to do that in the long run. If you want
to play a game, play it, you’ll return back to your project soon enough.

Here’s my project, it’s not launched yet but check it out
[https://www.ngrid.io](https://www.ngrid.io)

------
TaylorGood
No. It was a mission to secure cash flow at first, but I’m very happy with my
MRR which is services based.

The looming regret I felt coming on in my great corporate job would’ve been
not leaving. Having close to no control over your schedule except for PTO is
no way to live.

------
tonyedgecombe
No regrets but there are a couple of things that made the decision easy for
me.

1\. I started by switching to contracting, I had a good reputation in my niche
and plenty of contacts. Mostly it was lots of fairly short contracts which
allowed me to develop my own product in the inevitable quite periods between
jobs. I did this for two years before I quite contracting.

2\. I wasn't a very good employee, it wasn't until some time after I left the
corporate world that I really understood that it didn't suit me.

3\. I'm a saver, it would have been much harder to do if I lived from pay
check to pay check.

------
m0llusk
I'm barely making it but that for me is better in every way than my life as an
employee. Corporate products were always disappointments, the teams rarely
stayed functional for long, there was zero security, and the money simply
wasn't worth the cost of not being able to even try out my dreams in the real
world.

------
murph37
Contemplating this decision myself. Would love to hear others thoughts!

~~~
flanban
Money turns into time tokens. Therefore reducing your cost of living = more
time.

It's a different way of thinking and I like it. The comfort & security that
comes from a steady paycheck can go in an instant. Don't let that false
security keep you stuck in the rat race. Nobody wants to pay for you if they
don't have to.

I went to someone else's startup to escape corporate then success turned it
quite corporate as well. The process left me burnt. Now I contract and it's
not all roses, but I would never go back to the office life.

Corporate was unhealthy for me in mind body and spirit. You get lumpy, you
drink more, you eat garbage, you sleep worse, potential back & cardiac
problems down the road and most importantly sex dies.

fwiw, my father was an alimony ridden fine artist and my step father was a
senior partner at a big 4 accounting firm. My dad was a really happy, well
read and interesting guy. My stepdad's life is textbook american dream
perfection and it's a very sad and bland one.

~~~
yelloweyes
and where did he get the money to pay the alimony?

~~~
flanban
He was the head of the art & architecture department at a women's college.
Hence the alimony.

