Ask HN: Founders whose startups have failed, where did life take you afterwards? - aerovistae
======
jfb
I ran out of gas and left my cofounder; divorced; worked a succession of small
startup jobs, some better than others; ended up back at Apple. I have ideas
that I cannot express at Apple and so may end up taking another whack at the
piñata, now that a) I am not in the throes of a crumbling personal
relationship and b) I've gone round the carousel once, so I have some idea how
the world works.

I regret the way I left my startup, but at the time I was under an abominable
amount of pressure outside work, and I just sort of shot out sideways, like a
watermelon seed being squeezed between thumb and forefinger. I do not regret
leaving Apple to do the startup, not in the least.

~~~
rdl
I don't think it is possible to do with more than two of work stress; personal
life stress; physical safety or health stress simultaneously. One at a time is
ideal, but most startups have work stress and physical stress (due to time)
simultaneously.

You don't have to be single and childless to do a startup successfully, but if
you have family life or interpersonal relationships, they have to be good
ones, or at least low stress ones.

~~~
tluyben2
> One at a time is ideal

When people say stress they usually mean distress and zero of that is ideal.
'One at a time' for a period of time can be enough to topple you and the life
you have for a long time or forever.

------
buro9
Might be too soon to answer, my startup (
[http://microco.sm/](http://microco.sm/) ) just failed. As someone else put
it: insufficient growth, ran out of runway. But at times I wonder whether it's
because myself and my co-founder were of like skills and we didn't have a
strong enough sales function. Whatever, we failed.

I've had ~10 opportunities presented to me since announcing we'd failed. They
ranged from dev position through to CTO position, but ultimately I sent an
email to CloudFlare and have joined their team.

A startup failing is traumatic. Aside from the emotional trauma it may lead
you to doubt your own competency. I shine at product dev, and coding for that,
so sought a place to do that. To regain confidence in myself.

I also wanted regular(ish) hours and salary, to build able to rebuild some
stability. I'm getting married in a month's time and most of the cost of that
will be on credit card (founding a startup empties your coffers). So it was
important for me to be earning and giving our marriage a good start.

I may, in a few years, find that I want to return to the fray. But for the
foreseeable future I feel deeply happy that I've joined a great team working
on some hard problems, and that for myself I get stability out of it.

A startup is a ship at sea in a storm, I wanted to experience a boat in
harbour for a while.

~~~
eps
Have you at all looked at selling microcosm as a upscale managed forum
service? "Build a community" sounds like a far larger and less doable task
than "host your forum with us".

~~~
buro9
Our story is here: [https://medium.com/@buro9/the-journey-of-a-london-startup-
wh...](https://medium.com/@buro9/the-journey-of-a-london-startup-what-i-
learned-when-my-company-failed-c67acd74b862)

But in essence, we figured that out quite late... moving from helping to
assist building a community to having created an import tool and to push our
numbers harder by simply moving existing forums/communities to us.

We hit the end of the runway before the impact of that was felt. We didn't
manage to raise enough funds to continue.

We've open-sourced everything now, and I'm helping a couple of customers set
up their own instances. Most customers are staying on a single shared instance
though, as one of the larger sites is able to cover all of the costs of this
(via the affiliate fee structure we had built in).

It's a hard thing, to fail in such a way. We had 44,000 users, 280+ forums,
and some revenue. But the revenue was significantly lower than costs (when you
have employees, founders, etc), so the crunch hit us.

I hope that the platform continues to live, and that it continues to shine.
The customers are really happy, and some of the sales effort is still paying
off (I spoke to a customer 3 days ago, who have 4k users, and they are joining
the LFGSS.com instance of the platform).

It would be easier if we had failed more spectacularly, more obviously.
Perhaps by just not getting any users at all.

~~~
eps
Having read through your post I think your stagnation was due to the wrong
pitch, and, secondly and as odd as it sounds, due to that dorky faces
illustration at the top of your landing page. I can't think of a single case
where a forum maintainer would say "gosh, I need a better _community building
tool_ " rather than "I think I need a better forum". Then, say, he lands on
your page and the first thing he sees is a bunch of ugly stylized mugshots,
whereby what he's looking for is a single beautiful screenshot of a forum
page... I mean it may sound like a minor, subjective thing, but the first
impression lasts and I'm willing to bet that it had an extreme negative effect
on your bounce rate. You got the "hello" completely wrong.

(I'm writing all this because I really liked what you've been doing and I
still think it's a viable idea ... that you just happen to have overdone a
bit).

~~~
buro9
> You got the "hello" completely wrong.

Agreed.

We knew it too. But that wasn't the reason for our failure. Our sales pipeline
was already quite full and so our focus wasn't on changing the pitch even
though it was sub-optimal.

Instead we were trying to optimise the slow sales and onboarding processes as
those were what held us back at that point.

It's the usual thing: We had limited resources, and so we prioritised based on
what would achieve the most at the time. Even though our pitch was bad we
didn't have a problem with populating our pipeline, we had a problem
converting due to slow committee-based decision making and then onboarding an
existing customised/bespoke forum.

~~~
tim333
I read your Medium post and was puzzled where you wrote in regard to keeping
things running while you went and got jobs that:

"It feels very much like we would be creating an enormous amount of extreme
risk (the foolish kind)"

I'm puzzled what the risk was, unless you would still be losing money even
with no wage costs?

~~~
buro9
Yes, our costs (even without wages) exceeded the revenue and would do so for a
while. Revenue lagged behind the growth of costs, as is usual for affiliate
revenue when the communities are being built rather than traffic being
purchased.

The risk therefore was to the investors, whose support we needed to continue
even though we hadn't secured more experienced angel or VC support (not a good
signal).

------
Udo
In the early 2000s with a few friends together I founded and ran a web
development startup in Germany. Because I had been consulting for advertising
agencies since high school, building a service company for agencies seemed
like the natural thing to do. Afterall, it was the kind of customers I
understood well, and my cofounders were enthusiastic about the concept, too.

Despite doing every single conceivable thing wrong, we lasted a few years
before dramatic failure ultimately hit. I learned the insidious thing about
initial (modest) success is you become conditioned to underestimate the scope
and probability of failure that can topple you in the future.

One of my cofounders, who had always hated the startup part of our endeavor,
and who wanted us to become a respectable German company as soon as possible,
he was the first one to bail. And in hindsight he was absolutely correct about
choosing the right moment to quit. It took me a few more months of pouring my
own money in and taking on debt until I realized how absolutely screwed we
were.

Let me tell you: failing, in Germany, with your own money and in debt... it's
pretty bad. Here, culturally most of your relationships are built on a sense
of success and respectability. You lose all that in an instant. Customers and
business partners wouldn't even take my call when I wanted to do a last
farewell chat, even though we didn't owe them any money or anything like that.
The disappointment coming from my family and friends was just complete and
total, though they tried to be nice about it. The failure of my company now
meant that I as a person was also a failure.

After going down with the ship I went for a full time job, eventually sold a
side project/company for a bit of independence, and did this for a few years,
then transitioned to freelance software development.

I have to say after the startup - even considering the horrible parts towards
the end - after the startup there is a bleakness to a "normal" lifestyle I
could never quite shake off. Recently I've also gotten some very unpleasant
nudges from life which made me realize time spent on things is irrevocably
wasted if they're not important to me.

So I'm going into the fray again. In fact I'm working on a prototype right
now.

~~~
k__
Can't blame you.

I know a bunch of german companies who did everything wrong, but still operate
for years.

Many of my friends worked for so called "web agencies" who build shitty typo3
pages en masse. Most of the people working there were interns.

I worked at a academic spin off. They had good tech but bad UX. They worked on
for about 14 years and didn't make any money. Somehow the founders were good
at raising money from investors. So the bills always got paid.

~~~
Udo
_> "web agencies" who build shitty typo3 pages en masse_

This is what our initial success was built on. We had a two-pronged approach.

First, in the homeland of typo3, we got massive mileage out of our own CMS
product which could do everything that was oh so painful with the usual
products in this space. We became the "can do" guys, and we could do
everything so much faster and more elegantly than the competition.

Our second angle was our stealthiness: since agencies are in the business of
appearing way larger and more talented than they actually are, bringing in
outside contractors was a serious loss of face for them. We offered to appear
as internal agency staff in all customer interactions. We would go to on-site
meetings in their clothing style, even. Technical customer support calls were
transparently routed to our office, to complete the illusion that everything
was done in-house at the agency.

Everything else we did wrong, though. We had too many employees, some of them
were bad hires to begin with, and we worked them too hard, too. You can't keep
a whole team in death march mode all the time. We founders were terrible
bosses, as well. I was way too friendly to the point of being taken advantage
of, another founder was just generally clueless about everything, and the
third one was so harsh and troubled when he patrolled through the offices it
actually looked and felt like he was captain Ahab tormenting his trembling
crew. Then the budgets of the agencies crumbled suddenly, and almost over
night there was just no more money. The little work we got came at unworkable
margins. Agencies were poaching our employees. We took on big, risky projects
just to stay afloat. One of our biggest customers went bankrupt and then sued
us for everything they had paid for our services in the last 12 months. And
they won (still a bit unclear how that was even possible, but I found out
later their CEO was personal friends with the judge).

All in all, it was one hell of a learning experience. But there were some good
times as well. And the freedom to work on something you care about is just
priceless.

~~~
k__
> Everything else we did wrong

lol, implying completing "the illusion that everything was done in-house at
the agency" wasn't wrong in the first place.

Anyway, I still can't imagine why people found agencies.

If I want to do consulting, I'd become a freelancer, this pays much better and
there is plenty of work.

If I don't, I would work at a real software company that builds and sells
software products...

~~~
Udo
You are unkind but not entirely wrong. If you read my previous comment
closely: that's something which gave us an edge early on but later became an
albatross around our necks.

~~~
k__
I'm sorry.

I have some hard feelings about consulting :\

------
appreneur
Failed, job, startup -success...gave up company because of co- founder,started
again.. startup- success...amazing journey first 3 years...next 4 years hell
with business partner.

I have failed in the year 2011 after 7 long years at my bootstrapped company.
My business partner didn't want me around, I was pretty emotional after so
many years, I felt it's time to accept fate n move forward.

Broke up with my gf, I quit my company(gave my 67% to partner if he split
debt). So I pretty much walked out with million dollars debt and nothing on
hand, life was tough.

I started again,my small business was ok, my burn rate was low,I was ramen
profitable ...burning $2000 per month but all customers money, hired employees
fired lazy ones.

I just couldn't cope with debt sold my house, my car, my dads house , my aunts
house, fortunately n unfortunately I am from india, here people threaten with
dire consequences and people give all their life earnings for loved ones. So
all the assests cleared about 500k usd dollars.

I earned 200k usd doing consulting, mobile apps, web apps, sentiment analysis
,paid 60k usd salaries. Now I have another 200,000 usd to clear on track to
clear it but ....something beautiful happened , I married my gf after 3 years
of break, my ex-business partner wants to do business with me again since he
saw how I came out of rat hole,...

.I just have one thing to say "don't give up and hang in there with logic and
common sense"

I feel I will succeed financially in 2015 , Our product is coming
beautifully...then perhaps I can write a book...till then I have midnight oil
to burn..

~~~
swombat
How did you end up with $1m of personal debt? That seems like an epic
disaster, worth telling the tale to allow others to avoid making that sort of
mistake.

For my part, in 2 failed businesses I never went more than £10k or so into
personal debt.

~~~
appreneur
In india when you borrow for business ,it's usually personal friends, family
and distant cousins.

I never borrowed but from my family , but since my business partner borrowed
hell lot from friends, cousins, to keep it going , we were essentially paying
24%-36% interest on the debt, almost all the profit was going to just pay
interest.

And since we were Not making operational profit , we did turn over of 5million
usd , paid interest of 2 million and operationally we were in a debt trap. It
was classic case of denial of risk and peril. just thought that I will come up
with blockbuster product and wipe it all,it never happened in 7 years the
problems multiplied. Debtors were hounding on the door for their principal,
even though we paid them huge interest,it's like bank run, once they sense
things are wrong , everybody wants their money back on that day. Got into new
personal guarantee agreements ,made huge sacrifices and finally here I am.

~~~
jsudhams
Any reason why you went for 24% to 36% loan with friends rather than bank
loan? with the turn around like that you could have also taken small business
aid loan which are 12% at worst.

Also why would you pay US$ salary in India(assume)? There are lot of well
funded small startup's that would staff augment you for US20$ an hour for
decent programmer and you could have used remote college student for the
programming after initial training.

Haven't done startup as thinking of doing in in our environment gives me
jitters as I am not a very social person and gets really pissed of with govt
officials. May the that was only way you had at the time.

~~~
appreneur
I wrote numbers in dollars for wider audience understanding, I paid salaries
in rupees. As you might understand, a business loan from bank depends on
collateral security you can offer , I could only give 200k collateral hence
the business bank loan got limited there.

One of the most important lessons , I got early on is ,you need developers and
staff full time on rolls,right next to you if your business model is dynamic
and also you are not sure of staff quality. If you go to skillpages, there
will be thousand resumes claiming they know Python , once you hire them you
will know the quality, outsourcing works to that kind student quality is like
sure shot disaster.

Also I just was not lucky enough to find quality talent to outsource.

About india being good for entrepreneurs , yes and no, depends on what you are
working, but just to give up on startup idea altogether is not recommended
,choose carefully plan well and most of all EXECUTE WELL.

------
BIackSwan
Failed at a bootstrapped startup ([http://shoutt.me/](http://shoutt.me/))
earlier this year after a painful 2 years. Learnt a lot and failed a lot - in
practically everything - marketing, sales, growth, tech, operations. Lost a
fair bit of money too. Failed because the product was wrong and it took us 2
years to accept it.

Succeeded in one thing - found the right co founders.

In 2 months started working on the another idea
([https://doctorc.in](https://doctorc.in)) with the same co founders - moved
to India. Got funded this August. Could execute infinitely better on this one
because of all the lessons learnt in Shoutt. The experience of failure of the
first startup is paying off now in the second one.

I wouldn't have it any other way.

~~~
prezjordan
Shoutt was a great idea. I'm not sure why all startups like this fail to take
off - Vark, Jelly, etc. Is it a timing thing? I mean everyone has a smartphone
now, right? So how come it never works out?

Wishing you and your team the best of luck with the new venture!

~~~
BIackSwan
It seems a good idea at first. But it doesn't actually solve an acute problem.
Convincing people to use it on a daily basis is hard for such kind of an app.

------
joshmn
Had a startup (rather, small company that was established in the hosting
space), sold it when I was 19. Took that money, paid out employees, and tried
to start something new and fresh.

That failed. Had a co-founder that wasn't dedicated. Had some tech that I
could sell and did sell, but I still considered it a failure because I never
hit the mark I wanted.

Consulted, took some jobs with startups here and there. Those startups failed
for some reason or another so I went back to consulting.

I'm now consulting and lending myself out to people/businesses with ideas,
usually spending about 30 hours a week doing so. I spend another 10
volunteering and tutoring, and another 20 whipping up ideas of my own and
seeing if I can find something that I'm confident enough to run with.

My plan is to keep on trying. I have a book of ideas that I want to execute.
I'm mostly just waiting for the right idea and the right front-end guy. I'll
usually crank out an MVP and never release it because I fear it failing (and
I'm not a popularizer); sooner or later, though, I'm confident something will
stick when I find the right people to execute with (or they find me)

~~~
StandardFuture
You should publish your book of ideas as a GitHub repo and submit it here. It
might help you find a perfect cofounder for one of your ideas, etc. Or just
get general feedback. :)

~~~
JikkuJose
Have you seen assembly.com?

------
kolinko
During the past 10 years I tried launching startups a few times, failed most
of the times within 6-12 months. After each failure I spent 3-6 months trying
some more relaxing things (public speaking, dancing, standup comedy), and then
got back to doing startups again and again.

Right now I'm quite tired of all that, but fortunately the past micro-startup
& investments brought in around $300k which would be enough to live
comfortably for ~5 years in Poland.

Right now I'm 30 years old, and the plan is to keep on trying. What changed
during the past 10 years is that I'm no longer striving to go all in with a
financed business and spend 70-hour workweeks. I don't want to build a
billion-dollar business. Instead, I want to build something much smaller which
will allow me to have personal life as well.

~~~
aerovistae
In what universe is stand-up comedy relaxing??? My god I would be nervous.

~~~
kolinko
Like snowboarding or extreme sports. It's a different kind of stress - short
bursts. Compared to all-encompassing never ending kind of consistent stress
when doing startups.

------
staunch
After a previous failure, my co-founder (and co-brother) and I are moving to
the bay area this month, from LA. We're keeping our expenses low and plan to
drive for Uber part-time as a way of avoiding day jobs.

Even though I'm married and have a newborn, we're sharing a place and living
like (healthy) college students. We've both turned down huge salaries to work
together indefinitely.

I love creating products for people. I love solving problems and I love
writing code. The stress of a startup feels like a small price to pay to
create something great. And I really want to create something great.

~~~
kartikkumar
Doing a startup with a sibling, that's always intrigued me. I've thought about
talking to my brother about it a few times. Just feels like it might be
incurring too much risk to the personal relationship. What is your experience
of that aspect of doing a startup like?

Kudos got knowing what you want and going for it.

~~~
staunch
I have a lot of siblings, so I know it wouldn't in most cases. But with my
brother it's working great. Knowing each other so well makes it easy to cut to
the truth of things. And there's a level of trust that simplifies issues that
can otherwise be difficult.

------
nostrademons
[http://diffle-history.blogspot.com/2008/12/aftermath.html](http://diffle-
history.blogspot.com/2008/12/aftermath.html)

Spent 5+ years at Google after that, worked on a bunch of cool projects,
finessed my technical skills, learned how to push through difficult projects
until completion, rebuilt my confidence, and recently left to try again. We'll
see how it works out this time.

~~~
dennisgorelik
Did you notice that your blog is full of SEO-spam comments?

~~~
nostrademons
Nope, I didn't. Thanks, I'll delete them next time I bother logging into
blogger (I haven't in like 5 years). You'd think that spammers would realize
that Blogger uses rel=nofollow and so they get zero Google-juice from this,
but I guess not.

------
meelooo
I tried and "failed" a couple of times in the last 14 years. Having a family
pushed me to decide to settle down for some time. I started working as a
software engineer at Apple a week ago. The itch is still there though ;-).

~~~
monksy
Where do you think you went wrong and who do you think you can avoid that in
the future?

~~~
meelooo
The first time I picked the wrong co-founders (friends and all were
engineers). The second time I picked the wrong project. The third time my co-
founder died. The fourth time I wanted to do it alone but I almost burned out
before my family started to send the signal that it was time for a change but
I still think the tech and project are excellent though.

~~~
jjoonathan
> The third time my co-founder died

Wow, don't see that one too often (fortunately)! Was it a kinda-sorta-expected
thing (cancer, age, etc) or was it out of the blue?

~~~
meelooo
He had a scooter accident. My feeling is that he probably had the accident
because he was really pushing himself too much: he was barely sleeping 3h per
night and in the end his life was totally unbalanced with lots of prescription
pills to support it (sleeping pills, caffeine for day time, weight loss pills,
etc).

------
sirbetsalot
Started a startup in Vancouver using Machine learning to automate the sports
betting odds generating stack. Got two cofounders one MBA (yah i know) and a
fundraiser, both failed badly as I did all the code. ended up doing 40% of the
fundraising. fired the MBA for incompetence, 4 coders I had all left when
other co founder did a deal where the term sheet was pulled last second.
packed up left the company to the fundraiser and used all 12 man years of work
to bet on sports. Now a successful sports gambler, completely financially
free. Single most deadly killer to startups is a bad cofounder.

~~~
notastartup
im in vancouver too. interesting you are in to sports gambling are the odds
anything like poker? you should write an article on it.

~~~
sirbetsalot
I plan to most def, and I plan on open sourcing the machine learning tech once
I hit my first million next year. The odds are nothing like poker however, it
takes a long long time to understand all the ins and outs of making money in
sports gambling and the strategy is much different. FYI: I am awful at poker.

~~~
notastartup
be sure to tweet it when that happens, i'll check it out!

I've had the biggest temptation during this summer checking out the odds on
FIFA games. Although betting on Brazil would've been really bad!

------
nicwest
I got a job where I just get to write code, go home at regular time, and get
paid every month. it's awesome.

------
tomasien
I kept creating stuff, learned to code, ended up being on the front page of
the website that taught me to code, made a website that was in Time Magazine,
and started another startup that is now well funded and growing rapidly.

Just keep making stuff, stay afloat, and manage your mood - stay healthy, stay
happy, but PRODUCE AND PUBLISH LOTS OF WORK!

------
dont_pm_me
i worked at a startup with a couple of failed founders -- basically you grab
the next best engineering job you can find and lick your wounds until you're
either ready to start again or give up completely

~~~
meelooo
exactly!

------
blrgeek
Startup failed (early employee).

Did my own startup; growth was insufficient. Ran out of runway (7yrs of doing
startups).

Looked around & got a position as a Product Manager in AdTech, since I didn't
want to get back into a dev role, and wanted to move more into the prod/mktg
side.

Since then moved into an accelerator working with early-stage startups on
mktg/prod.

Life's been much better than I expected when I failed.

------
jeremyriney
I went and lived in a monastery for a little over a year. Then started
something new. Couldn't stay away for long.

~~~
kartikkumar
Wow, where was that? Sounds like a fascinating experience. Did you cut off
from tech altogether for that period?

~~~
jeremyriney
It was near Redding, CA. Unfortunately the monastery needed a website built
for them so I spent quite a bit of time working online. I couldn't escape it.
But building and maintaining a website for a few hundred users was much more
relaxing then building and maintaining one for tens of millions.

~~~
bjwbell
Was it [http://www.monasteryofstjohn.org/](http://www.monasteryofstjohn.org/)?
I grew up there (the town not the monastery).

~~~
jeremyriney
It sure was...

------
unclebucknasty
Another startup. And another, until it worked.

Here's a question that is less frequently asked: to founders whose startups
met with moderate _success_ wherein it turned into a lifestyle business that
could be sustained indefinitely, but never appeared to be reaching the life-
changing initial vision, what did you do?

We focus a lot on success and failure as binary concepts, but I think there
are a ton of businesses that meet with some success, but fall well short of
the initial goal.

------
aaronbrethorst
I consulted for a couple years, joined someone else's startup, consulted
again, and am currently very much enjoying a real 9-5 job with a great salary,
decent benefits, excellent coworkers, and the best work-life balance I've ever
enjoyed.

I may not have won the startup lottery, but I've never been happier.

------
jkent
In the late 90s, I started a cloud-type hosting provider, with an angel round
$100k+, dropping out of university. The dotcom crash happened and raising more
money became near impossible. I was inexperienced and tried to do everything
myself, and hired the wrong people.

I morphed it in to a web development business that did OK, then worked out it
was easier working for someone else (got my life-work balance better) - in a
VC-backed startup that ultimately got acquired.

I left to finish my degree. Got confused for a year and did a bit of sales.
Then another startup that I couldn't get off the ground (services marketplace)
- perhaps insanely ambitious.

Then I trained as a teacher (forgot that), teaching inner city kids how to add
up.

I now work at Google in partnerships, where I am largely happy, married, get
to travel a lot - and occasionally still 'get the itch' ...

------
raminassemi
Someone should start a blog interviewing failed startup founders and letting
them tell their stories and share their lessons, really in-depth. Maybe even
bring in other people for multiple perspectives.

~~~
mdparker89
The problem is these lessons are, for the most part, already out there.
Unfortunately, some things you just have to go through to really learn. All of
the mistakes I made were ones I read about. It just took me a while to
recognize that my mistakes were the same as the ones I read about.

That said, if somebody did start that blog I would definitely read it.

~~~
nostrademons
Yeah, this was the biggest surprise for me in founding my own startup. I had
worked for two previous startups to learn what to do and what not to do, and
went into my own startup with a whole laundry list of pitfalls to avoid. It
turns out that I ended up committing almost every one of them (except the ones
that were management-related, and those only because we never got big enough
to employ people. I think that when I ended up becoming a team lead at my job
later, I ended up committing a bunch of them too, or nearly committing them
and catching myself right before).

The nice thing about having knowledge and experience is that oftentimes it
shortens the time required to _realize_ you're making a mistake. Folks who
haven't done this before and haven't read about other peoples' experience can
sometimes waste _years_ doing something that clearly isn't going to work. If
you've read about it before you might catch yourself after a few months, and
if you've personally experienced it from the other side it might take you a
couple weeks. But it really does require committing the mistake, learning
(painfully) from it, and then doing it the right way a couple times before
you'll start getting it right automatically

~~~
raminassemi
> The nice thing about having knowledge and experience is that oftentimes it
> shortens the time required to realize you're making a mistake.

Great point.

Btw. seems the site you're linking to in your profile isn't working :)

------
clamprecht
While I was working on my own (small) startup, I took a contract at a job
search engine in 2004, called Indeed.com. I ended up joining as employee #1,
and stopped working on my own startup about a year later. Fast forward to
2012, Indeed.com was acquired for a cool billion. After that, I started
Searchify.com (still going), and I'm currently living in Argentina, traveling
through Patagonia at the moment.

~~~
n_coats
How is patagonia? Heard the wifi isn't so abundant there.. Congrats, I hope to
make it there one day!

~~~
clamprecht
Internet is generally slower, there is no 4G yet. Wifi is actually pretty
common it seems, but I'm in a fairly popular part of Patagonia right now (San
Martin de Los Andes and Bariloche). Tomorrow I'm driving South towards a town
called El Chaltén, where there is apparently NO cell coverage, because the
people who live there don't want it. I'll have to depend on Wifi 100% there.

Aside from Internet coverage, Patagonia is beautiful, if you like lakes and
mountains (and glaciers)!

~~~
molsongolden
Are you climbing?? You're right in the thick of it.

~~~
clamprecht
Now I'm in Calafate (glaciers). I didn't do any proper climbing on this trip,
but I did a bunch of hiking. Doing a glacier hike tomorrow too!

------
rdl
Failed, consulting, startup, failed, consulting, success, failed, job, job,
startup, sold, job.

~~~
jeremyis
This is a really interesting path. Could you supply more info for each phase?
Like a sentence or two and the maybe the time you spent on each?

~~~
jacquesm
He really should write a book. It's going to be one of the most interesting
stories in start-up land.

~~~
bshimmin
Seconded. The whole HavenCo story is genuinely fascinating.

------
100k
I left my company due to cofounder conflicts and lack of traction (we had a
few customers, but weren't able to raise funding and I didn't see it going
anywhere). I was really depressed for a while, and for lack of a better idea
started doing freelance/contract development. After a couple of years of that,
I got the itch to work on a startup again and decided to come back to the Bay
Area for that. I got a job at a seed-funded company as their first employee.

------
apa-sl
Few years ago on one day I took al my toys from the equity market (I've got
this feeling that I'm not creating any real value and wasn't happy with that)
and burned all money in my first startup
([http://fashioner.com](http://fashioner.com) domain is for rent/sale ;).

1 year later I've inspired my friend to start another startup (service market
on national level). Unfortunately VCs in Poland did not wanted to believe that
it is such a good opportunity (and it was, currently 2 big competitors sharing
this market). But the good thing was that we have inspired another friend to
join us and gathered some money.

Now, 2 years later, we've managed to create another startup from all that ;)
([http://ElimiApp.com](http://ElimiApp.com)). Just taking off, seed in the
bank, fingers crossed!

I think it is just about the way you think and what you want to do in live. I
could live very comfortably live from securities transactions (but create
nothing, nada) or comfortably while working in some bigger company (no way).
Instead I've choose to fight for years for my own thing.

------
kbouw
Began a startup senior year of college (Thryv). Managed to build a team, get
sales, generate revenue and score a large partnership. Long story short, I was
a customer of my own product and assumed I knew what other customers wanted. I
spent the next 6 months having a product built without validating my initial
assumptions before launching. The product was too niche only fitting customers
who had my specific workflow and I ultimately found this out too late when we
ran out of steam/resources. Total timeline (including fuckups) was 3 years.

I was non-technical at my first startup (domain expert &
business/marketing/sales) and after I shut it down, I spent the next 8 months
teaching myself how to build software programs, becoming a now tech co-
founder.

I then started my second startup
([http://notiontheory.com/](http://notiontheory.com/)) by getting $20k pre-
sales in 2 weeks to validate my idea before committing to it.

Attempt 2 has been far more successful and we're already beginning hiring in
month 5 bootstrapped.

~~~
aerovistae
For your number 4 bullet under "Services," I'm pretty sure you mean "Voila!"
rather than "Viola," which is a musical instrument similar to a violin.

~~~
kbouw
Thanks :)

------
mhluongo
My first startup failed after a couple years. My co-founder and I were pretty
worn out, and I had some medical issues. After a month of recovery (both from
the biz and med stuff) I started contracting at two promising startups half-
time. I went full-time at the beginning of this year, only to have a side
project take off. Currently running that with the same co-founder and a new
one.

------
almost40
Started in 2007, no tech skills..

\- Idea I published was novel & since has been copied by oodles, including
celebrities, large corps & one copy now has millions of users.

In 2009, after not being able to get my idea out in timely manner I started
doing front-end dev jobs. I've been failing at those too for the past five
years. I'm not a fast coder.

In 2013, now with technical chops & a solid tech team we created tech that got
us invited to demo to entity in the valley and received some good amount of
attention. Though the entity in the valley was not nice to us, seem like they
just wanted to possibly steal our work & squash us like a bug.

So, Im happy to say I invented something oodles have copied with success & our
work gets the attention of entities in the valley.

Though is it worth it if...

Your broke, jobless after Friday, childless, live with a parent, in debt, just
broke it off again with cheater g/f who lives with her parent and in five
months you'll be 40?

~~~
wushupork
What was the idea you published out of curiosity?

------
bgdam
Did not do enough market research before building and launching product. A
product similar to ours released some months ahead of us and got rave reviews
in a lot of dev forums (HN included). Took that as validation of our product
as well. Turns out, comments on HN don't really translate into money over the
counter. Fast forward a year and we have near zero growth. Eventually both the
similar product and us shut down.

After that I needed to rebuild some confidence in myself, so I joined a small
consultancy company as a lead dev. It's been a year since that happened, and
now I'm beginning to feel the startup itch again. Working on a few side
projects. The plan this time around is to _not_ quit the job and go full time
on the startup till it starts producing a certain amount in monthly recurring
revenue. Let's see how this goes...

------
bigpeopleareold
I am working now. I am going to stick with this for a long time now.

Whenever I want to go into a venture, anyone I work with seems to have serious
issues. I worked with someone who was a bit too controversial, another too
attached to the business model, believing things will turn around.

All I can say is: Know your founders. I'd go far as to focus on their personal
situation, like their risk tolerance, their "philosophy", their personal
attachments, etc. The goal for a company is not to save the world, but to make
money for you and your partners. If any personal attachment can get in the
way, like "saving the world", or "keeping control of the company", it will. My
major failure was not seeing this.

At least for me there is a regular salary now.

------
LogicX
Had a startup in Boston that went through TechStars 2010 (third startup) - got
funded, fizzled on customer growth.

Now in Myrtle Beach, SC building a startup community with Startup.SC
([http://Startup.SC](http://Startup.SC)) and promoting an alternative place to
do tech through [http://WhyNotTheBeach.com](http://WhyNotTheBeach.com). Also
working remotely hacking websites (InfoSec).

Looking forward to doing another startup once I build up support network,
angel investors, etc.

(Actually in Boston this week for Angel Bootcamp & TechStars Demo Day) -
contact me through profile if anyone wants to get a drink.)

~~~
frankydp
WhyNotTheBeach could get some good buy in from the other towns like MB.
Daytona, Wilmington, Panama City, Pensacola, Destin, numerous others. Pool
resources from the Chambers of Commerce and what not for decent advertising
and recruiting. Anyways, great concept.

------
benologist
Moved onto idea #2 which was a refined #1 that skipped a lot of mistakes, it
wasn't financially viable to work on it so I moved on to idea #3 while mumsy
picked up the rent.

Idea #3 was this 'passive revenue stream' idea of making tablet jigsaw
puzzles, I figured it would be very quick + easy to set up and generate enough
income to cover me for something else. That quickly changed into a full time
effort to grow the company as it was so enjoyable having a product that makes
money + could be better.

------
lrmunoz
I realised my startup had failed last year, and part of the realisation was
that it was doomed from the start. When I was coming to terms with that I
applied to a bootstrapped startup for which I'm now the CTO. It's nice to have
a steady salary now while I learn a hell lot about how to run a successful
business in the real world

Why did I fail? Well, basically what I wanted to achieve was only a nice idea,
one that everyone loved when I explained it. But then, when we implemented it,
it was so badly executed that it didn't do anything useful. Then we fell in
the feature creep trap, I argued with my co-founder and he parted (because I
didn't listen to him, and because he wasn't 100% committed), pivoted into
another failing product (at least I managed to sell it and have some real
customers) and finally entered into zombie mode for a while (actually the
company is still officially in business as I had to take on some consultancy
projects in order to pay back €50K in loans we took). Total time of my life
spent: 4 years.

In the future, I will try it again, and of course I will do different. First
of all, it'll be small from the start (I'm even thinking of doing something
that just provides some passive side income, in the level of 1000€ a month).
Then it will have to be profitable from the beginning.

------
agotterer
My co-founder and I started an ecommerce analytics company. We self funded
(minus a small accelerator investment towards the end). The tech was hard and
took us much longer to bulild then expected. We felt we were finally heading
in the right direction towards the end but we're running low on money and gas.

We spent 6 weeks shopping the software around in attempts to get acquihired.
We ended up with two interested companies after talking to about 15. One made
a small offer for the tech and generous offers for us to join the company, the
other made just generous offers and wasn't interested in the tech. My partner
and I didn't see eye to eye on the offers and were able to convince both
companies to take us separately.

Three months later we were introd to a company that wanted to buy the tech and
didn't need us to come along with the deal. It wasn't the huge exit we had
once hoped for, but it brought some closure and the product lives on.

After a promotion 2 months after joining I'm leading a 13 person engineering
team and enjoying having some money and time to spend with my wife and
friends. I have some more startup left in me but plan to see this one through
for a while.

------
acjohnson55
One of my startup's advisers intro'd me to the founder of a small consulting
company whose mission I really loved. When I first started consulting, it was
a nice opportunity to decompress from startup life and enjoy a job where I
could basically clock in and clock out. A few months later, I was ready to
start picking up some responsibility. I ended up joining the client
permanently and it's been great so far.

On the side, I advise startups a bit, which is cool because it lets me keep
the lessons I learned in my own startup fresh. I've come up with a couple
interesting startup ideas myself, but I don't feel pressed to be a founder
again any time soon.

I'd consider doing a startup again down the line, but I'd be very
discriminating. I'm entering a more risk averse stage of life, and I think I'd
rather position myself to join something as a leader that's already at least
somewhat proven but still has a lot of upside. It takes a refined skillset to
be viable for such a role, but that's what I'm aiming for.

------
peteretep
We never made any money, and I was the only permanent technical staff (but
also technically the CTO) but we had some amazeballs clients - Samsung,
Siemens, Tesco, RIM (while they were still cool), and so on.

When we stopped being able to pay me a salary, I turned it in to a real CTO
job at a 150 person software company. Our client list gave some real
credibility there, as did being able to talk a good talk and looking
presentable in a suit.

I suspect this was a phenomenal career move: the previous startup CTO stuff,
and any future small-company CTO stuff will be "real" in the eyes of
recruiters because I've also managed a big team, budgets, etc - the "real CTO"
role validates all the hacking code at smaller companies while claiming to be
CTO.

I think there can be a credibility gap for a 30 year old team leader at a
profitless company calling themselves a CTO, but having also done a more
traditional CTO role at a bigger company allows you to regain that
credibility. I can talk confidently about CapEx, OpEx, I've been through a
rubber-glove-type due diligence process, been deeply involved in high-level
strategy ... I feel like I could spend the next ten years doing 3 people
startups again, but then walk in to another "big" CTO role if it didn't work
out because of this.

Anyway, ultimately that wasn't what I wanted to do, as much as it was
incredible experience. So the wife and I packed off to somewhere warm and
cheap, she has a job that pays the bills and for the flat. I'm keeping myself
busy by running a one-person R&D lab for a large listed company whose industry
I have domain knowledge in, finishing my dissertation, and I've branched in to
staffing because it's amazing how much quick cash you can make by messaging
ex-coworkers on Facebook (and if you're a Perl developer in the UK:
[http://perl.careers/](http://perl.careers/))

~~~
mattmanser
You are suffering heavily from imposter syndrome.

Because there are so few 150 person companies, most CTO jobs are for small
companies.

This doesn't make them any less of a CTO job. In fact, the hard decisions for
a CTO are often going to be at the start. Choosing the stack, building the
initial team and engineering culture...

So stop questioning yourself.

------
hayksaakian
Keep in mind this depends on when you fail.

What happens when you take 10million in VC and then fail?

Compare to a 100k angel round and then fail?

~~~
zerr
For 10M I guess you can afford to buy chickens. They will produce eggs, so
problem solved... ;)

------
zeeshanm
One of my very first attempts was to build a tutorials site where I'd write
stuff on photoshop, php, css, html, etc. Wrote a few tutorials, (re)designed
website over 10 times before launch, but did not get any traction. Gave away
my tutorials to other sites in the ecosystem.
([https://web.archive.org/web/20050208112644/http://invano.com...](https://web.archive.org/web/20050208112644/http://invano.com/?photoshop:chocolate))

About the same time someone told me may be I should build sites where people
can contribute and I wouldn't have to worry about creating content. So, I
created this search engine that would index tutorials from all other sites.
Built the back-end and some front-end but gradually lost interest to another
project.

Then I built this another site with tools for webmasters. This was actually
launched with some modest success as by this time I had learned enough about
Apache/PHP/MySQL etc.
([https://web.archive.org/web/20051215081101/http://viewhtml.n...](https://web.archive.org/web/20051215081101/http://viewhtml.net/)).
But never figured out SEO/traction.

These were in high school and after these tries I gradually lost interest to
other stuff. So that was that.

Then in college freshman year started this company to build computer hardware
with my roommate. This was actually the first attempt to start a company.
Everything else were just side projects. The idea was to build Dell equivalent
for Linux.

I think I read this note on some mailing listing about why Linux was not
widespread (Android was not mainstream, yet) because there was not any well
established distribution mechanism. There was a need to build an equivalent of
Dell that would ship computers with Ubuntu and provide user support.

So we bought off-the-shelf parts to build our first desktop computer to sell,
built it, and installed Ubuntu. Then my roommate and I had a fallout. So that
was the end of this.

And there are a couple of more things that didn't take off. But life was not
really impacted drastically as all were learning experiences.

------
contingencies
I don't see my main startup as having failed, instead I decided not to keep it
going. It was very close to profitability in a huge market (China) with
enormous growth potential. The problem was I needed to run around doing non-
fun business stuff (raising capital) and double-down for another few years to
see it through. If I had, I'd be rich now. But I chose not to, and have no
regrets. So where did life take me? In short: better places - more money, less
stress, family, leisure, travel. Find what you want out of life (hint: loads
of money is rarely it) ... work smarter not longer.

------
phugoid
I left my comfortable job in Dubai, moved the family (with 2 small kids) to
Toronto to build an enterprise database product, launched it at the niche's
world conference, pivoted once, and spent all the money I had. That took nine
months.

When it came time to look for work I got a decent job offer in the Toronto
startup scene as a django dev, but I called up my old employer in Dubai and
found out they had not managed to replace me. So I replaced myself! Moved the
whole family back out to the Middle East.

You'd think the whole experience has turned me off startups forever, but....

~~~
skrebbel
Why not do the startup in Dubai?

~~~
phugoid
I was convinced that it wouldn't work unless I dove in and did it full-time.
You lose your residency visa when you quit your job here, and you have 3
months to leave the country. There are ways around it but they are too
expensive if you're bootstrapping.

------
sergioschuler
I have failed (about 50k people saw how I failed and what I learned here:
[http://www.sergioschuler.com/startup-lessons-learned-from-
my...](http://www.sergioschuler.com/startup-lessons-learned-from-my-failed-
startup/?hvid=3EvjLn)) and now I work for a pretty normal company, as their
digital marketing head (not as impressive as it sounds, but I enjoy it).

I am building something very simple on the side (libertarian tshirts, since
the idea is growing here in Brazil) and I still crave to solve problems.

------
wonjun
I looked for a startup job specifically because pg says joining a startup is
the next best thing, and then managed to join a growth stage startup. What's
changed from doing a startup is I no longer have to think about if the company
will survive in x months and I am just focusing on the technical side of
things. My days have become easier and I get more positive outcomes each day,
but in the long run, I feel like I have to get back in the game.

------
Ixiaus
I built another one that I left (it's still going) and am now the director of
software at a startup that went through the same Techstars class mine did.

------
32faction
Adding onto this: for those who have failed and started again, did the failure
affect your fundraising campaign once you did get traction on a startup?

------
arjunrajkumar
8 months since I stopped working on the failed startup. Learnt how to code in
Ruby on Rails by building small side projects in the evenings/weekends & also
worked full time in the last 8 months. Going to start working on something
again from this week. Life has brought me back to where I was before - but
with a few lessons learnt, better skills & more humility than last time.

------
gwbas1c
I interviewed for a bunch of jobs, and then found one with a small startup
where the leaders were much better at running a business than I was. I now
lead a very fun project to work on, and feel like I met my career goal in my
early 30s.

I'll need a new challenge in a few years, but for now it's nice to be in a
routine and be a critical member of a kick-ass team.

------
onethumb
I'm a sucker for pain, or it's in my blood, or something. Numerous failures, a
few successes, just kept trying. Finally found something that _really_ worked
and still doing it, 12+ years later. I will say - I learned _way_ more from
the failures than the successes, and they massively shaped my current success.
Good luck! :)

~~~
kirse
Funny you would say "in my blood"... any relation to Danny or Angus MacAskill?
That last name sticks out in my mind because of those two, weird to see it pop
up again. (Or is it just a really common last name?)

------
fizerkhan
Failed startup
[http://www.quadmsolutions.co.nz/](http://www.quadmsolutions.co.nz/) after
painful 1.5 year. Failed because of co-founder issues.

Then, I and my friend started working on new startup
([https://www.atatus.com/](https://www.atatus.com/)) and got 100 customers in
2 months.

------
adamzerner
My startup that failed aimed to provide more detailed student reviews of
colleges. People wouldn't answer questions, and I couldn't get traction.

It failed the summer after college (after starting it a year before). Now I'm
at a coding bootcamp. I'll work for a year or two, and then give it another
go.

------
Yadi
Moved to United States and abandoned all the horror stories I faced in my
country after what my startup brought me to! You never know, even the failure
of your dream company might be the reason you are a live or maybe your life is
begging for a new beginning and failure lead to it.

------
n_coats
For those whose startups failed and ended up working as an engineer at another
company, what would you say is the main difference between the company you
work at now and your failed startup? Basically, what lacked in your startup
that ultimately led to it's failure?

------
anubhabb
Little bit frustration, little isolation, little thinking and then ANOTHER
IDEA, ANOTHER STARTUP :)

All of these actually set well after my startup actually 'closed' as right
after the closing I was too buzy getting my employees and my guys placed in
other companies.

------
ivankirigin
I went to work for Facebook then Dropbox, and now I'm on my second startup. We
just pivoted, so it sort of feels like the third.

I've worked at a few different kinds of companies, and there are good and bad
aspects of each kind of company, each stage of development.

~~~
jacquesm
Heh, super good to see you back at it. Tenacity is the #1 factor in
determining eventual success imo. Good for you :)

------
tluyben2
Did many startups in my life and some failed; just went on to the next one. I
promised myself (when I was 13; almost 30 years ago) never to need 'a job' and
I never will do. If you have the same wish then just don't give up after
failure.

------
jobposter1234
I got lucky and found an excellent job at a local company. No connections, no
hope, other than a good fit.

There is hope. I only know because I feared the future, and came up feeling
better than I'd imagined, once I had some support.

------
aosmith
I've failed myself a few times. It normally consists of a month of bouncing
around doing passion projects / thinking before returning to work.

~~~
salemh
You don't find "returning to work" has a stigma with the bouncing around?

Meaning, startup to "big corp" or "any company" doesn't mind you were bouncing
around.

I'm just curious how dev's go through the interview/hiring process with the
jumping around like that. As a more Operations dude, it hurts me pretty badly,
even though I "jump" a lot with startups. Requires more explanation.

~~~
skadamat
It all comes down to the messaging / how you position yourself when you
interview. If each 1-2 year stint was a good learning experience and that made
you a better ops / dev, then you need to present that on your resumes / cover
letters. Also, ideally while doing startups, you've also met a ton of people
where you know that if the current project doesn't work out you can always
work with / for one of them!

~~~
aosmith
+1. I've never really worked outside of startups and there's always somebody
who needs an engineer even if it's pseudo temporary.

------
ismail
Went back into consulting, to build up my capital reserves again. Having
learnt some hard lessons and burnt through my savings.

------
jdg
To the couch for 2 months.

And then back to another startup. ;)

------
kowdermeister
I read "consulting" a lot in your comments, but what does that actually mean?

------
makuchaku
3 co founders, now working for our investors in their tech firms.

------
elwell
Contract work and actually having money

------
pulkitpulkit
what about non-technical founders?

------
xinterp
Variant 1:

A friend and I were out of jobs and eager to test an idea we had about local
real estate which had the potential to scale. I raised 25k in seed money from
family.

That person was more biz/sales oriented and we hired one of our other friend
who had experience building software. Both of them became lazy and
uninterested after a few months and quit as soon as we ran out of money.

I worked at it for almost a year, alone with a part time admin assistant.

Managed to pay back the seed money and "live through" that year but ended up
very tired and still broke.

Variant 2:

One day I get a call from a MBA in a similar industry and he was very excited
about the model. I was tired, broke and felt lonely, I easily got convinced to
re-launch under a new name for a broader market. (original was in french)

Created a whole new business, new name, new website, new everything. With the
technical side mostly handled by me. 3 months in just as we were about to
launch the new partner starts arguing all the time and suddently didn't trust
me. We were not even putting our new version in front of clients yet and he
was panicking.

He forced a shut down of the business. It was the second time I was building
this model - was still broke and exhausted.

Variant 3:

I felt relived and thought I'd go work a day job for a little while. Then 3
days later I'm sitting with one of the client of the first business and for
him it made such a difference that he trying to convince me to try again and
offered 100k in investment.

Worked my ass off again for launch #3 - except this one I was aiming for the
stars and had 100k in bank. Made a huge mistake in hiring technical talent,
took us months to get a shitty product out. Made a huge mistake in hiring
admin talent, burnt through 15k until we had to stop working with that person.
And worst, 6 months in, as we're trying to hit it really hard we realize that
the real estate markets we were after slowed down dramatically (40%-50% drop
in sales)

So we ran a test campaign and indeed, it confirmed a huge drop.

I had to cut on every aspects of the business, let go of hires, go back to the
plan and do a lot of thinking. We managed to survive a few months but it was
extremely hard to get money out of clients because they knew the market was
down and felt like they would waste money by investing in our platform in such
a downturn.

We had to pivot our business model and our client approach multiple times in
the last 3 months. Which in retrospective brought me tremendous knowledge and
made us try new innovative tactics to help my clients and show them that we
could be trusted.

Slowly but surely we've started to generate revenue and I'm proud to say that
in the last few weeks we've actually hit our target, we're no longer digging
ourselves in a hole.

I'm now still completely broke but at least I can pay our team every week and
I know that it's not just money that we borrowed but money that we earned and
I'm confident in our new way of doing things.

Reiteration works. It will get through anything, look at water. And so will I.

~~~
ckeck
Thank you for sharing...way to be persistent and not give up! Hate when I see
founders seemingly giving up too early because they don't see the instant
success/traction of the lucky few.

On another note, I wanted to ask about the admin/personal assistants. Why were
these roles necessary at this stage in the company? Asking because I'm seeing
more of this, but even with the funding I've raised it's still a hire I don't
feel like I can justify.

Thanks!

~~~
xinterp
Thanks for the reply!

About the hires, it depends on your business and where you are I guess.

In my case the idea was a new way of marketing new constructions online. I
managed to get 23 new home developers as client. That along with the 900+
prospects I've qualified and followed up with during the year.

Combine that with the fact that I was the only one working on the website and
our system in general. kept me extremely busy and I needed someone part time
to hold the books and do the small monotonous tasks.

------
paulhauggis
Since 2009, I have been a founder of 3 different startups (and 10+ different
side projects that I couldn't convert to successful products). All 3 failed.
My problem was choosing co-founders that either did not have a passion for the
idea or just weren't willing to do what it takes to run a business.

Someone may be a good developer, designer, or co-worker...but that doesn't
mean they will make a good co-founder. I learned this the hard way..and it was
painful.

I now run a small business with 2 other co-founders..and have been profitable
since day one. I quit my job over a year ago and never looked back.

~~~
tluyben2
Have had that before; also where I was a bad co-founder. Usually it is just
bad timing as I saw; decided to start shortly after which something else just
collapses (personally, past business) in such a manner that the co-founder
cannot focus. Someone I started doing an internet-of-things startup with in
2008 got hit by the crisis and divorce at the same time (they were probably
related, but I don't know that). It went very well (we worked productively
together and progress was great) for 6 months and then he just started to show
less and less interest until, at some point, his Linkedin changed that he was
now working for some big company. He forgot to mention that in the months
before building up to it.

------
schuman
2002: Started a small business.

2008: Pivoted to a somewhat more scalable and clearly defined small business.

2011: Started a true startup.

2013: Realized I'd started the wrong startup. Got a job at somebody else's
growth stage startup.

~2018: Will start another startup. But this time I'll have a hell of a lot
more understanding, expertise, connections, and

~~~
serf
>2002: Started a small business. 2008: Pivoted to a somewhat more scalable and
clearly defined small business. 2011: Started a true startup.

What's the difference? Truly curious. The singular focus?

~~~
schuman
Scalability.

They're all b2b with high ($500k+) customer lifetime values, but the first
business, in the best case, could serve about 30 clients simultaneously. The
second could serve (in the best case) a few hundred. The startup could serve
thousands.

------
michaelochurch
I spent 2.5 years at a startup and did some of that time working purely for
equity. I'm not sure if I count as a "founder", as it was unclear where the
founder/employee distinction was, and I'd say that I was probably Employee #1
or #2 rather than "a founder".

The truth? Ugh. The pitch is that, even if you fail, you'll learn a ton and be
slotted into a much more senior role in your next job. The reality? Yes, you
do learn a lot. However, you get the same kind of job you would've gotten
before the startup. Not more. That 2.5 years you spent building a complex
product from scratch? Fucking wasted. In your next job, you're still going to
be assigned to legacy maintenance, and random bugs and tickets like any other
junior, not given real work and a meaningful role.

I consider this pretty dangerous, because there's nothing worse than gaining
2-3 levels in ability, but having to linger at a low level because your
startup's failure (which may or may not have been your fault; in my case, it
wasn't) invalidates the experience completely. You might fare better,
psychologically, if you don't go through the startup and gain levels of
experience that you won't be permitted to use in the next job. It's easier to
function if you're at-level than if you gain 5 years of experience in 15
months but no one believes you.

It's pretty humiliating and you might break. (This was my Google experience.
Granted, I had a rotten manager, but the psychological load of coming off a
failed startup didn't help the situation.) I think the whole "nothing bad
happens when your startup fails" pitch that you hear from VCs is disingenuous.
VCs fix some peoples' careers after startup failure, but that's not going to
happen for an early employee (E #2, not really a founder) of a company that
didn't even make it to the A round.

This isn't just an issue that I faced. I know plenty of hiring managers who
worry about ex-startup people, not because they take the failure to mean
anything about the person (for some good news, that stigma is mostly gone) but
because they know that people who did startups are (a) a rank level or few
beyond where they'd be slotted based on seniority, and (b) have chips on their
shoulders. It's a valid concern. When it's an acqui-hire, the founders are
usually tired of startup stress and ready to take a (still well-paid and high-
status) subordinate role, but after a startup just fails you get someone who
feels a need to prove himself and won't be happy being re-slotted to a second-
year junior programmer.

So... to answer the question, it's not an easy road. After a short spell at
Google, I consulted with a horrible startup (that I've taken off my CV, and
that inspired many of my cautions about startups, see:
[http://michaelochurch.wordpress.com/2012/07/08/dont-waste-
yo...](http://michaelochurch.wordpress.com/2012/07/08/dont-waste-your-time-in-
crappy-startup-jobs/)) that wanted to hire me as VP/Eng but only if I
disparaged, in writing, the work of 10 engineers, many of whose work I knew
nothing about. (I turned that offer down.) Then I worked in finance for a
while, did a bit of consulting (including lottery design and technology
selection) and have done some R&D (new product development and data science)
in Baltimore. My life _has_ gotten better, and with the blogging and the fact
that I'm starting to know a few things about in-demand fields (machine
learning, Haskell, Clojure) I'm now finding reasonable demand for what I can
do. It's been a lot of work to get back on track, but I have, and I'm probably
stronger for having had to fight this hard.

I think that, in the long run, the experience is good for you. The year after
(or few) can be hell. The pitch to the effect of "even if it fails, you'll get
a great job afterward" is not really true. It's true for founders who line up
with marquee investors and whom the investors really like, but in the average
case and for people of average means and connections, the outcome seems to be
neutral to negative.

My case is just one data point (and an atypical one) but I think that most
veterans of failed startups (early employees hit the hardest, then founders,
then late employees) will admit that their careers have been set back, not
accelerated, by them. It's certainly not fatal, but it causes a loss of time
and, as you get older, you realize just how finite that is.

~~~
enraged_camel
>>I consider this pretty dangerous, because there's nothing worse than gaining
2-3 levels in ability, but having to linger at a low level because your
startup's failure (which may or may not have been your fault; in my case, it
wasn't) invalidates the experience completely. You might fare better,
psychologically, if you don't go through the startup and gain levels of
experience that you won't be permitted to use in the next job. It's easier to
function if you're at-level than if you gain 5 years of experience in 15
months but no one believes you.

Wow, this basically describes the frustrations I had with my previous job to
the letter. While working there as an engineer, I also founded a successful
community service non-profit on the side. Even though it was nothing like
founding a "real" company, it still gave me 2.5 years of really solid
experience with building, managing and leading teams of diverse people (among
lots of other things). We became really successful in our space. It was great.

The problem? While working on the non-profit, I first caught up to and then
surpassed my boss at my day job in management and leadership ability. He was
my senior, yet I would see him make mistake after mistake, and I'd think,
"wow, I made that mistake like, 3 years ago." I tried to help but he wasn't
interested - he is very much the "do my job during the day and then go home,
drink some beer and watch sports" type of guy. No drive for self-improvement,
even when it became obvious that he was severely lacking. I ended up building
a lot of contempt for him, and when my frustrations became too much, I left.

~~~
hkarthik
This is probably the most salient point in michaelochurch's reply.

You can always get a job after a startup, but whether you will feel happy and
satisfied in that job is a much more difficult question.

------
fleitz
Left me with a far better understanding of business, a lifetime of stories,
some great friends, and a better engineering job.

Finishing a prototype this month and going to try it again, this time with a
long time friend on the business side, and a developer who knows more than me
on the tech side. As a leader you never want to be the smartest guy in the
room.

Biggest take away was that leadership is far more about inspiring people than
giving orders, you have to inspire people personally, and then inspire them on
the shared vision.

------
rrpadhy
After 4 years of working to build a big VC fundable startups (3 different
products), I was pretty burnt out. I am continuing the last product, but now
my focus is on building lifestyle startups which brings about $1m revenue
every year.

Joined a job on the side, which would help pay my bills and help my family
settle down. In the meanwhile, I would be chipping along to build my small
revenue generating startup.

------
notastartup
Curious, how do you define failure?

