
Ask HN: What was it like to quit your job and focus on your successful startup? - mattbgates
For most people, dreaming about quitting a job to focus on a side project or a startup is a dream come true, especially if it ends up being successful. It can bring about so many emotions and fears all during that entire process... not knowing what is going to happen.. and what if it failed? Would it have been possible to return to your old job? So, for those who quit their jobs and were successful, how did it feel and what did you learn?
======
welanes
> What was it like to quit your job and focus on your successful startup?

1\. Time became my most valuable asset. Everything was filtered through the
lens of "does this save me time?" and so I optimized everything: The gym
(worked out at home), shopping (got delivered), dating (used fleshl...joking!
:).

In the words of Joel Spolsky, "Every day that we spent not improving our
products was a wasted day".

2\. I worked harder than ever before. My job was tough but output ebbed and
flowed with meetings, management, plus the usual office time wasters. The
startup workday is more straightforward: wake up, coffee, write code, listen
to users, coffee, learn how to add value to the market, coffee.

3\. Every two months or so I look back and shake my head at how lame the
product was, how little I knew, and how inefficient my workflow was. Which is
to say, I continue to learn at an incredible clip yet realize I still don't
know a thing. I expect this trend to continue - if it doesn't, I'm not
growing.

So, yeah, overall it's been An Incredible Journey™. My only regret is that I
didn't start sooner.

It's actually a gift how easy it is to go from idea to product to business. To
paraphrase Murakami, 'If you're young and talented (or can code), it's like
you have wings'.

We're living in the best of times.

~~~
berzerk5
What process did you use to validate your idea? That's where I'm stuck. I have
tons of ideas but I don't want to spend months and months working on something
that people don't need or care about because as they say "cashflow is the
lifeblood of a business".

~~~
acuozzo
I'm currently facing this problem as well.

~~~
HeyLaughingBoy
Build something that people are already paying for.

------
antigirl
This might be slightly offtopic but I've been thinking of working on my own
ideas for a decade now. I tried working on projects in the evening and
weekends but there isnt enough time. Not only does it effect your social life
but also effects your motivation and drive in general. After looking at code
on a screen for 7 hours, last thing you want to do is go home and look at more
code [I guess this depends on your age, i'm 32 now - not an night owl no more]

Anyway i started contracting last year for this exact reason, at around
£300-400 day rate and now i've saved enough to quit and follow my 'dream', my
last day is JULY 7th. I have enough savings to last me 2 years, sustaining my
current social life. no frugalness.

~~~
cheez
Unless you catch lightning in a bottle, you'll need 4 years.

~~~
fsloth
4 years for what? To find product/market fit? To become profitable? I presume
you are referencing some rule of thumb that is not familiar to me...?

~~~
cheez
OP is not experienced. OP has no idea what he's doing. It will take him 1 year
to realize the idea he chose sucks. 1 year to panic and freelance while he
figures out what he's doing next, then 2 years to reach profitability.

------
jasonkester
The biggest change was how much more free time I had.

When you're building a Nights and Weekends side project, you get used to
stealing whatever free hours you can to work on the product. But you also
necessarily build things so that they don't take up much of your time every
day. If they did, it would interfere with your day job and that just wouldn't
work.

So when you remove the day job, you find that suddenly you have this
successful business that runs itself in the background and you can do pretty
much whatever you want with your day.

Most people in this situation will immediately fill that time up with work on
the product, and I did to some extent. But I also made sure to take a bunch of
that time just to enjoy with my family. I eventually settled on 2-3 days a
week where I was "at work", with the rest devoted to other pursuits. Both me
and my wife are rock climbers, which is an "other pursuit" that will happily
expand to fill the time available. We're also parents, so ditto there.

I also make a point of downing tools for a while from time to time. Again,
because I can.

I took the kids out of school and dragged them off backpacking around
SouthEast Asia for a few months the first year. We did a couple more medium
sized trips this year, and I took the entire Fall and Spring off because those
are the best times for Bouldering in the forest here. Again, work is happy to
ramp up or down to accommodate because I never shifted it out of that ability
to run on nights and weekends.

So now, I burst for a few weeks at a time on work stuff (with possibly a more
relaxed definition of Full Time than most would use), then slow down and relax
for a bit.

It's actually not so bad.

~~~
yazan94
Could you elaborate on how you got your business to be successful?

~~~
zha
It is covered at
[http://www.expatsoftware.com/articles](http://www.expatsoftware.com/articles)

~~~
jasonkester
This one in particular:

[http://www.expatsoftware.com/Articles/guy-on-the-beach-
with-...](http://www.expatsoftware.com/Articles/guy-on-the-beach-with-a-
laptop.html)

------
Grustaf
For me, and probably for most, it's not a matter of quitting your job in order
to work on your "successful" startup - if it were already successful then
there'd be no issue at all. Rather it's about quitting while the startup is
just beginning to look reasonably good, _in order_ to make it a success.

Since I've been working as a mobile developer, and also management consultant
(my other career), it's always been extremely easy for me to find a new job
whenever I needed, so there has been very little risk involved.

Still, it did require some savings, since our startup is very research
intensive and will take several years before we see any revenue. We secured
some basic funding now though, and things are looking good for the next stage
too so I will only have needed 6 months or so of buffer.

In summary, my view is that if you're a reasonably skilled engineer or have
some other attractive occupation, there is nothing to fear. The worst that can
happen is really that your startup doesn't work, you'll go back to what you
did before with a few months of missed income but with plenty of useful
experience.

I don't think there are many situations or cultures where a failed technology
startup attempt on your résumé would count against you in any way, in most
places quite the opposite.

~~~
ryandrake
Your (and other) replies seem to assume that the startup is something you're
already doing on the side, while employed full time doing something else. Is
this really that common?? Most, if not all places I've worked assert IP
ownership over anything you do while employed, even on your own time. That's
100% what keeps me from moonlighting and/or starting my own thing on nights
and weekends, and keeps me from contributing/consulting for friends who want
help with their idea. How do you have any confidence that your startup is
really yours when you could get sued by a former employer the day you quit to
grow it full-time?

~~~
fancy_pantser
Even if you signed a PIIA, double-check that it's enforceable where you are
employed and is as far-reaching as you think it is.

For example, the California Labor Code stipulates that regardless of what an
employment contract or PIIA says, an employee owns the copyright and patent
rights to his inventions if the invention is made entirely on the employee’s
own time, without using any of the company’s equipment or technology, as long
as the invention (a) does not relate to the company’s business, or (b) did not
result from work performed by the employee “as an employee” of the company.
Washington and other states have similar laws that override any contract you
might sign with a company.

An attorney in your jurisdiction familiar with this area of law can give you
all the answers you need in just a few minutes for a nominal fee.

~~~
bluesroo
Your last line is very important. In PA I was able to get a full write-up on
the NDA/ IP portion of my contract for $150. If you are planning on making
something potentially profitable/ valuable in your spare time, $150 is peanuts
for peace-of-mind.

------
pedrohidalgo
I did it twice. Both times I failed but I don't regret it. I felt very good
when doing it. I lost savings but it was a good live experience.

On the second time I created this plugin:
[http://plugins.netbeans.org/plugin/61050/pleasure-play-
frame...](http://plugins.netbeans.org/plugin/61050/pleasure-play-framework-
plugin) I tried to make a living of this, I only sold 5 licenses of 25 dollars
per year and to develop this plugin took me 2 and a half months of hard work.

Didn't have a problem getting a new job both times.

~~~
keyboardmonkey
Out of all the people I know, software developers are generally the most
allergic to spending money on software.

------
williamstein
I gave the following talk exactly one year ago right when I decided to quit my
academic job to focus on my "startup dream" (now
[https://cocalc.com](https://cocalc.com)):
[http://wstein.org/talks/2016-06-sage-
bp/](http://wstein.org/talks/2016-06-sage-bp/). It's a year later, and the
quick summary is that I feel basically really, really happy to be working on
this company. It's exciting to be successfully hiring and building a team of
people who work very well together and can focus 100% on a specific problem,
unlike how things worked for me in my part of academia (pure math research).
Though stressful at times, doing what I'm doing now is much less painful than
trying to build a company _while_ doing another fulltime job (namely teaching
at the University fulltime) -- that really sucked. I'm extremely glad that
customers are paying us and investors funded us enough that I can do this.

Having the __luxury __to focus on one thing, rather than juggling several, is
much like having an office that is neat, tidy, and uncluttered. It feels good
in the same way. At least by quitting a job and focusing on a startup, you
have the option to focus 100% on it. Actually focusing 100% on one thing is a
difficult skill in itself, even with the right circumstances; however, it 's
completely impossible (at least for me) with two fulltime jobs at once,
especially jobs like teaching (which involve lots of public speaking at
scheduled times) or running a website with paying customers (which demands,
e.g., responding to DDOS attacks).

------
jaequery
Well I ran a solo startup so my experience might be different from others but
for me, it was like living a dream. While working full-time somewhere, I
started this SaaS business and soon after, the monthly income kept doubling to
the point I was able to quit my job knowing my living expenses are cared for.
When I quit, it was like wow, the feeling of liberation just hits you so hard.
I worked for 7 years prior to doing that and now I was free. The feeling of
being able to go outside anywhere at any time of the day, go shopping, or go
eat at a nice restaurant, just relax at the beach, stuffs you just couldn't do
when you are working full-time somewhere. It's like getting out of jail for
the first time. That's what it was like for me to quit my job and focus on my
startup.

~~~
patricklouys
Are you still doing that or back at a job?

~~~
jaequery
This was almost 7 years ago and I sold the company in less than a year of
operation. It wasn't like retirement money though, got about a year of break
from work. I've launched a few startups after that and joined a couple other
startups in the process. But nowadays, I just try to do consultant gigs.
Looking back, I still can't get over how great it was though and I regret
selling it too early. I also realized just how hard it is to launch a
successful business and I was pretty lucky with my first.

------
foxhop
Only asking for opinions from people who were successful is literally asking
for survivor bias perspectives.

I dream of working for myself but I've never taken the plunge. My income from
side projects is about 1/3 of the way to my minimum number to quit and go full
time.

I do a lot of thinking about this, my number is the same as my financial
independence / early retirement number.

One of the biggest things that holds me back is medical insurance for a family
of 5. Having an employer offsets this cost a LOT.

~~~
zghst
Oh that is very tough! I'm only in my early 20s, but I worry so much about
retirement, probably one of my most deep fears! I figure the only way for me
to get ahead is to be financially successful, either my startup makes it or I
go to get my PhD in a cutting edge, lucrative compsci field.

~~~
vasco
I chuckled at the thought of getting a PhD to be financially successful.

~~~
akerro
He's also in his 20s and worries about retirement money! The financial system
will crash at least twice before he retires

------
dwviel
I agree with some of the other's comments that time is the most valuable
asset. Be productive! Also: 1) Most of the advice that you find online is not
really applicable. I like the stuff that Sam Altman (yes, ycombinator) puts
out because it most mirrors what I've experienced. 2) You need to do it
yourself. Whatever it is. Just do it. 3) Funding is a game. Here on the east
coast investors pretty much only fund the growth stage of a company after you
have real traction and are virtually guaranteed some kind of success. You will
need to fund your startup out of your own pocket until then! This is what they
call "friends and family" because you will be hitting them up for money,
favors, meals, places to stay, etc. 4) The tech is the easy part, as that is
what you know. Marketing and selling is the hard part, as that is what you
likely don't know. It is the part you should try to get help with if you can,
but finding someone that knows what their doing is tough, so you can be
sidetracked quite a bit. 5) The "do things that don't scale" is completely
true. Reaching out one-on-one has been the most successful way to engage
potential customers, even though it is very time and labor intensive.

------
markatkinson
I left my permanent position and was lucky enough to continue working on a
contract basis to continue covering some of my bills.

I reached a point after about 4 months where I realised the journey to make
the business profitable would most likely be a five year slog, and while the
opportunity was there it wasn't a cause I felt I could devote 5 years of my
life to.

So gave the software for free to the people that were helping with beta
testing and went back to my job. I found the most positive thing was how it
helped propel my career at my current employer as I got a better role, they
seem to have more respect for me afterwards and I operate more independently
now.

So I suppose if you can build some sort of safety net before quitting that
helps.

~~~
1k
Thanks for sharing. Could you tell us a bit more about what were you building?

------
jonathanbull
Last year I quit a great full time role to focus on my side project,
EmailOctopus ([https://emailoctopus.com](https://emailoctopus.com)). Haven't
looked back since!

I didn't take the plunge until quite late on, waiting until it was making
enough money to comfortably cover my personal expenses. No regrets there -
growth was slow in the early days and if I hadn't had the luxury of a monthly
pay packet, I probably would have given up before I got the chance to properly
validate the business.

Transitioning to full time brought more stress than I expected, but the
experience is priceless. In the past few months alone I've learnt more than I
did in 3 years of employment.

Realistically, what's the worst case scenario? I'm a reasonably skilled dev in
a strong market so there's not much to lose. If it all goes wrong I'll get
another job with a load of experience (and stories!) under my belt.

~~~
jftuga
Nice site, looks very useful for us. We need to send out emails to many
students once or twice a year. Now that we have switched from on-prem Exchange
to Office-365, this has become a challenge.

~~~
jonathanbull
Thanks! Glad to hear we might be of use. Feel free to drop me a direct email
if you've got any questions (jonathan@domain.com).

------
jondubois
I never returned to my old job... Why would you go back? I did return to
working as a contractor for a while. A lot of failed startup engineers become
contractors.

I'm back working for a startup again now so I guess I'm just going back and
forth.

I've worked for a few startups and none of them has had an exit yet but one of
those I have shares in is doing relatively well.

Doing contracting work is a smarter decision in general. You can actually plan
to make a sizeable amount of money and then watch it happen without taking any
risks - It's all within your control. With startups, you might often feel that
it's outside of your control, especially if you're not a co-founder.

------
Disruptive_Dave
I can tell you what it was like to quit my job and focus on a very-early-holy-
shit-what-are-we-doing-startup. Was at a marketing agency for 10 years when I
left to pursue my first co-founded startup. Made the decision after we got a
little organic press and signed up 5k+ users in 24 hours. I had been looking
for an excuse to leave and do something new anyway.

It was scary as hell (no revenue coming from the startup), fun as hell,
challenging as hell. Had my savings all planned out to help support the
adventure, but still had that daily stress of knowing every dollar I spent was
not coming back anytime soon. That part wasn't fun. But I didn't have kids or
a mortgage and knew this was my chance to do something of the sort.

10/10 would do again in a similar situation, though knowing what I know now, I
might have launched a business instead of chased a cool idea.

------
RHSman2
Am 3-4 months in with concept. Have anchor client and consultancy partnership.
The biggest and wildest thing is moving from someone with an idea to a
visionary leader in a space. It's fundamentally awesome to take said idea,
turn it into a offering and go out on the line with it. I have had nothing but
wonderful experiences with others helping me out. I am 40, have 2 kids, a dog
and a wife and a pretty good network which I have had to really 'work'
(authentically) but the assistance from others, trust and good feelings are
something that have made me believe in the human race a bit more! In corporate
it's all protectionism and petty arguments AND a visionary thinker is not what
they want! I am lucky to have found an excellent co-founder who is a great
counter part. Definitely taking/balancing risks, going fast and working really
hard (doesn't feel like work building your own thing though) however the
finances have to be calculated and I have taken the consulting/product route
which seems to be good but converting a service driven model to a recurring
revenue model is the goal AND the challenge.

------
zghst
I am 2 months into doing this, it feels a lot like when I moved to SF, lot of
things up in the air but very promising. I had a 6 month financial plan but it
was hard to adapt to the lack of income and seeing my savings decrease month
by month, so I'm doing contracting and TaskRabbit. I'm not really a ramen
noodles person, so I make due with what I can get at the grocer.

I have a previous coworker who'd love to help me, but I don't want to babysit
his work and I feel he's not valuable enough to the business. I would like
another cofounder, but it doesn't bother me that I'm doing it all on my own, I
have spent the last 10 years getting ready for this, so I'm more than ready. I
am doing more than okay on my business alone, but I wish I had some expertise
for a second opinion. I am really really thinking about going into an
accelerator program or seeking angel investment, but I'm apprehensive about
taking cash at this (or any stage). My biggest fear is actually having to get
a real job again, I will do anything to prevent that from happening since that
means my startup is dead.

~~~
kakarot
I'm curious, do you mind sharing a bit about what it is you're working on?

~~~
zghst
An app to embarrasses an existing industry

------
erikrothoff
I'm on my last day at my current job before taking the plunge to focus on my
half successful startup! I'm going down in pay to about half, we're still
losing money every month for me being employed. Our runway is ~6 months before
our savings are out. Basically we have to double the monthly revenue that took
5 slow years to grow up to. Exciting and scary times!!!

~~~
kakarot
Good luck! I hope it all works out. Scary times, indeed :)

~~~
erikrothoff
Thanks! We were also able to cheaply rent a room at a shared office space, so
it feels super real. :D

------
cjr
I started my screenshot Saas product, Urlbox
([https://urlbox.io](https://urlbox.io)) as a side project back in 2013. There
were times I did think about shutting it down as the amount of time spent on
it initially compared to the revenue growth was just too depressing! A whole
3.5 years later it had grown just enough that I could begin to take it more
seriously and actually support myself full-time working on it.

As with everything there are pros and cons. The pros are obviously that you
get to spend your time doing something you enjoy (hopefully), and can work
whenever and wherever you feel like (this can also be a con!). The cons are
that you will always be worrying about stuff like churn, whether servers will
go down whilst you're away on holiday, how you're going to grow enough to
support a family etc etc.

The long, slow Saas ramp of death really is a thing, and there are no silver
bullets in terms of growth/marketing - just many small things that all
contribute. I also always used to think 'if only I could just get to $x MRR
then everything would be so much better and I'd be much more comfortable and
relaxed', but when you do eventually break through that barrier you realise
you're just more worried about how you are going to achieve the next one, so
it's kinda never ending!

I also agree with other posts here that if you're already a decent developer
in a good market, then what is the worst that can happen really? Try doing
some fearsetting. I'm sure you could always find another job if your thing
doesn't work out, but you do need to give these things time. I also failed a
bunch of times with other startup ideas, one of which was also YC backed.

------
gwbas1c
Quitting my job was great!

Let's just say that my mistake was that I was too afraid to hurt my co-
founder's feelings. If we parted ways when we should have, I might have
actually gotten somewhere. (Then again, I might have gotten nowhere either!)

------
greglindahl
I had my financial ducks in a row before I did my first startup -- I knew how
much "fun money" I could expend getting the startup to work. Most of the
horror stories I hear revolve around people who didn't do this.

~~~
gameshot911
Re: "fun money" \- how much was that figure for you? (range is fine if you
don't want to give an exact number)

~~~
greglindahl
Well, I'm single. So it was several years of living expenses at the time of my
first startup, and it's FU money now.

------
daliwali
I started doing this recently by quitting my job, and I currently have no
income.

There is this assumption that one must build a minimum viable product that has
to be released as quickly as possible, so much that it's become startup
mantra. It's no surprise that a lot of these products seem to be technically
shallow, everyone is reaching for low hanging fruit.

I feel rather alone trying to do something that I think hasn't been done
before, or if it had, wasn't executed well. I don't think I could possibly
commit to it without having strong motivation, which I struggled with while
having a full-time job.

The biggest technical/social challenge I have is to make something that a non-
technical user could easily get right away and make something with it. I think
the automation of web dev is an inevitability, and frameworks were just a
historical blip on this path. The same thing is happening to web design.
[http://hypereum.com](http://hypereum.com)

~~~
ramadis
I think the whole point of an MVP is to validate the hypotesis you make about
your users.

In your case for example, do you know who your users are? Are they
entrepreneurs? Current software developers? Anyhow, who is going to use your
service?

I'm not trying here to undermine your project since it indeed sounds pretty
awesome, but to reinstate why the whole mvp movement has a reason to be.

~~~
daliwali
For marketing-tech, sure it's a great model, but getting out an MVP as fast as
possible doesn't always make sense. Sometimes it takes an order of magnitude
more effort to get to "minimum" or "viable" depending on the product. On the
contrary, a lot of developer's side projects just feel like things that any
reasonably skilled developer could build given a few days.

The question of finding customers, is exactly the same as finding who is
demanding software to solve business problems (i.e. not current software
devs).

~~~
aregsarkissian
Getting an MVP out as fast as possible doesn't contradict an MVP that takes an
order of magnitude more effort to build. It's just that the ASAP for the
latter case is whatever amount of time that it takes to build it.

------
andrewchambers
Just a reminder that life is pretty short, and worst case, you can probably
just get another job and only be 6 months to 1 year behind your friends in
terms of savings.

~~~
zghst
Yes that is the worst case for me, but also I really really do not want to
kill my dream. I like work but I will live in the park with my laptop if it
comes down to keep going (no joke).

------
fergie
I quit my job to start my own company last January. Its been fairly successful
so far.

For somebody like me, and probably a lot of HN readers, its _actually_ a
fairly low risk proposition because qualified, experienced software engineers
are so sought after. Whatever you are doing, you will always be able to pick
up a $1000-$1500 a day gig when you need to bootstrap your actual project.

My old boss has contacted me a few times to see if I want to come back-
definitely do not want to.

You talk about "fear", and you talk about a "successful" startup. Here's the
thing: You never know if a startup will be successful, and you just have to
give it a go for the love of it, rather than any expectation of success. Don't
be afraid- there are plenty of worse things in this world than a failed
company.

Have learned a lot about bookkeeping.

~~~
afpx
How do you find your day gigs?

I've tried to do this, but the time required to do it (via reaching through my
network) has really been a lot. More than expected. And, then I tried to go
outside of my network, and I was just overwhelmed with the repsponses. I
couldn't easily discern which opportunities were worth the time.

Is there someone I can hire to be my freelancing mentor?

~~~
geff82
mail me : eriklistserve at gmail dot com

~~~
afpx
email sent!

------
wonderwonder
I landed a contract to develop a saas system before I really knew how to
program for the web, I had some prior systems programming experience but had
not coded for about 5 years. I quit my job to develop it and delivered but was
never able to land another customer.

I still have the original client 3 years later and the company grosses about
$3,500 per month and I net $1,250. It pretty much runs itself, requires maybe
2 hours of work every 2 - 3 months. I spent a little over a year trying to
grow it from the initial customer with no luck.

Landed a job as a full stack engineer afterwards and I really like it. I am
actively looking to start a new project but I will keep my main job while
doing it. I had the benefit of a wife who makes a good salary to support me
during that prior adventure (Still do :) )

------
12s12m
I actually have a different take on this. I was building a side project 2
times in my past, to a point where there was some buzz around these side
projects. And, I didn't have a job when I was working on these. However, as
the products were nearing completion for V1. I got very good offers for
contract work. I also had debts, so I took up the jobs. However, this led to
the products failing to get any traction.

So, if you are planning to leave a job and have a good product which is
getting you even half of the money you need. Leaving your job will only
increase the chances of success. However, hanging on to the job while working
on a product is going to be much harder.

------
wolfer
TLDR - Sort out your finances first, startups are extremely stress inducing
and even now with our startup at the point of break even, £1m ARR and 100%
growth predicted for next financial year, I still currently earn less than I
need to live but with the promise of a strong exit in the next 3-4 years if we
hit our targets.

Previously I contracted as a full stack developer bringing in other developers
on projects as and when the project timescales wouldn't have been achievable
with just me. Running a software consultancy alone, dealing with all of the
usual rigmarole of a business and performing proper client outreach was
stressful, but financially and personally very rewarding (especially when you
close a big deal completely on your own).

In order to get involved in my current startup, which at the outset was
comprised of a designer, biz dev (CEO) and myself as CTO I had to cut off ties
with my previous clients and dedicate all of my available time to the new
startup. I had leveraged myself quite a bit running the previous consultancy
as billings were growing year on year, so my VAT/Corporation tax accounts were
generally paid out of job fees towards the end of the year rather than set
aside throughout the year, leaving me in a negative cash flow position when
stopping work for existing clients. Luckily there were some ongoing payments
that didn't require development resource, so the small admin time required to
invoice and chase up was all that was required, and enabled me to setup
payment arrangements with HMRC to settle these liabilities over a period of
time, out of this cashflow. Setting up these arrangements was very stressful,
and I would strongly advise anyone coming into a startup to fully evaluate
their financial situation before committing even if the opportunity seems
huge.

Initial salaries in the new start-up were minimal (£1000 p/m approx), and it
took a solid three years, extremely long working days, almost unmanageable
personal stress and around £0.5m of funding before we're now up to an above
average average salary, £1m ARR, a team of 15 and strong growth projected for
the coming year.

Success is a subjective term and occasionally I have to refocus to see the
light at the end of the tunnel, but with enough grit, luck and determination,
it’s possible to tip the balance to a point where success is now more likely
than not.

------
hesdeadjim
I've had two very different experiences starting a company.

The first time I was two years out of school with $12k in the bank, had a
partner with a ton of experience, and a decent idea. We crunched for six
months, launched, failed, and then tried to pivot. I ran out of cash a few
months before the iPhone launched and had I had a longer runway we could have
ported our app to the iPhone and potentially seen success.

A year ago and nine years later than that attempt, I've started a small video
game company with another friend (justintimegame.com). Despite my life
situation being more complicated and expensive to maintain, the prior nine
years success combined with my wife's income basically lets me try and fail
until I get sick of it instead of when the money would run out. Obviously I'm
aiming for success, but the massively reduced stress from barely worrying
about money let's me be much more open to experimentation while also being
resilient to failure.

I don't regret starting and failing my first company however. It set me up for
having a higher risk threshold and an interest in startups that ended up
working out quite well for me.

------
geekme
I started up twice. First was a e-commerce market place and the second one was
into mobile app development. Both failed. I was running them for around 4
years. Now I am back to a full time Job. I never regretted my failures since I
learnt a lot from them and now I am working on my 3rd side project hoping to
succeed.

------
verelo
So for me I left a job and worked on my startup that ended up unsuccessful.
Fortunately during that time I met my current business partners and we have
since made and sold a company that by most people's definitions has been a
very good run.

Expecting to get it right is the failure we all make at some point (even when
we say out lout "this might not work out" we still somehow expect it to work).
Expecting failure to lead to something positive is the long game I'd urge you
to wait for, it's hard to remain in a good mental state at times while you're
working hard and feeling under appreciated, but that is sadly just what it's
like.

------
mezod
The way I did it was to start freelancing so that I could pay the expenses
with less hours and then use the rest of the time for sideprojects. Finally,
one of my sideprojects
([https://everydaycheck.com](https://everydaycheck.com)) shows interest and
traction, so it's easy for me to just do less freelance hours and put more
time into it, hopefully I can get to a point where I can work 100% on it.

I guess the "quit your job" problem only exists if you have major
responsibilities, like a family, or paying debt back. Otherwise, it makes no
real sense to consider it, the opportunity is too big.

------
cylinder
Self employment is incredible when the money's rolling in, and terrible when
it's not. I can't speak for a full fledged startup with funding though because
then you just work for investors.

------
smdz
1\. One day you are excited with the possible opportunities, then you are
overwhelmed and then you are depressed. If you leave without a plan, it takes
a few months to just get the mind straight. If you do have a plan - it falls
apart and you still end up spending a few months that feel unproductive. I am
not discouraging on having a plan - you must. But also note that you made a
plan with an "employee mindset".

2\. 6 month financial backup is usually not enough. I have heard many stories
where people try going independent for 6 months, run out of money and start
looking for a job. What happens is - entrepreneurship gets into you in that
time and if one goes back to a job, I can bet they feel even more frustrated.
You need 1.5 years of backup or 2-3 years of "frugal living backup". I struck
positive cashflows in just about 5 months, but it wasn't good enough. I
distinctly remember thinking "Maybe, I should have done this part time". Then
I struck a mini-gold-mine at 8 months. Having a good backup will help you
persist longer. I did not have a growth strategy that worked. But I focused on
working and doing the right thing. Keep it rolling.

3\. The biggest worry I had when starting was about providing "enough" for my
family and any emergencies for next 1.5-3 years at any point in time. Unlike
many stories, I promised myself not to wait until I go bankrupt or in a lot of
debt - Nearing that is a huge red flag, where I would typically exit and take
a regular job. However, taking a job is the last thing I want to do. That
thing kept me money-oriented for a while and made me work on stuff that
generated positive cashflow.

4\. Would it have been possible to return to your old job? - Maybe, but I
would not want to. I waited too long to jump ship. Infact, my experience on
multiple "good" jobs is what is keeping me away from them. Once you taste
entrepreneurship, its hard to go back

5\. I do not consider myself successful. May be semi-successful, some people
see it as success. But I have come a long way from fearing failures. Success
may or may not last long. I enjoy the process and the tremendous personal
growth it results into. I ensure my financial backup now gives me 5-6 years
minimum to start afresh - if I have to. Do not undervalue the role of money -
it definitely makes things easier.

6\. This is my favorite quote about Karma. I heard it many years back (and
thought it was impractical). Especially useful when I feel I did everything
right but nothing works: "Karm karo, fal ki chinta mat karo" (Do your duty
without thinking about results)

P.S.: I don't know about others, but I have restricted myself into writing
lesser HN comments because it takes quite a bit of time/energy. This one is an
act of impulse. How do other entrepreneurs feel about this?

------
apatters
If you're single, childless, and have a few thousand dollars in savings,
quitting your job to focus on a side project or startup is very easy. You can
achieve your dream in the next 24 hours. Here's the roadmap.

1\. Give your employer your 2 weeks/1 month notice (depending on locale).
Taking this step immediately is critical because the urgency and shock of the
change will force you into being fast and practical about all the subsequent
steps.

2\. Create a monthly budget for yourself which assumes no income that you are
not 100% sure about. So if you have interest from investments or a freelance
contract that's a absolute guarantee you can include it. For most people the
income side of this budget is going to be low or nothing. Your goal with this
budget is to stretch your funds out for 6-12 months. The good news is that in
2017, the principle of geoarbitrage allows you to live on virtually any
budget. If you live in the Bay Area your next step is going to be to move
somewhere cheaper. On the cheapest end of the spectrum, I'll use Thailand as
an example because I live here, you can get a basic apartment in the suburbs
of Chiang Mai or Bangkok for $100-$500/mo, your initial arrival can be visa-
free, and you'll live on delicious Thai food from a restaurant down the road
for a few dollars a day. Network heavily with people in your intended
destination before you even arrive because it'll make everything 100 times
easier.

3\. Now create a business plan for your new entity. The business plan should
include a description of the product or service which you're going to market,
how you're going to market it, what you're going to charge (start high), and
any and all costs of development and operation including your own time. It
should include monthly profit/loss projections (you're not allowed to use
these projections in your budget, they are goals, not guarantees). The most
important thing about your business isn't what product or service you
initially offer. Once you have assets and control you can try anything you
want. Until then the goal of your business is to make enough income that your
assets are growing, no matter what that entails.

If you're leaving the country as a part of this process I would advise forming
an LLC and opening a bank account before you go, as these things can be
difficult from overseas. You'll be very busy trying to make money and living
your dream so you don't want to have to deal with paperwork.

Prepare yourself mentally to work very hard for at least the next 6 months and
do whatever you need to do to make enough cash. You will become practical and
decisive, and you'll learn many realities about business, such as _cash flow
is king,_ very quickly. I got my start being nickel-and-dimed by agencies in
India over Elance. It sucked and it was hard and it was 100% worth it.

There are many objections to this strategy which typically stem from risk
aversion, or a desire to not worry about money. I would submit that if one
objects to the risk, this plan is a personal growth opportunity: it will teach
them how to handle stress, plan for contingencies, and so on. If the objection
is that they don't want to worry about money, I would point out that money is
just a way for people to quantify your value to them, and since no man is an
island, there are great personal and financial rewards to be reaped from
confronting this objection and discovering what other people truly value about
you.

Doing step 1 first and now is the key. If your path brings you through Bangkok
let me know and we'll grab a beer! I've seen many people succeed at this and a
few fail. Your odds are better than you think.

------
jhylau
one word: liberating

