
Being a Solo Founder of a 24x7 Hosted Web Application - tortilla
http://garrettdimon.com/post/27002421078/being-a-solo-founder-of-a-24x7-hosted-web-application
======
jasonkester
I think the key is to choose your technology and customer base carefully.

A lot of the fear I detect here is along the lines of "what if (something
breaks|customer calls) at 4am on the day my wife is giving birth???" The
reality for me in the last five years is that's not something you need to
worry about.

My sites generally don't break, and not because I'm awesome or anything. They
don't break because they're built on a stack that doesn't need any attention
pretty much ever, and for the most part they don't try to do anything
particularly remarkable. Reading/writing from databases and displaying the
results on a web page is pretty much solved. You get four nines right out of
the box unless you go out of your way to choose a flaky platform.

My customers do actually call from time to time, but it's not the sort of
thing I'd consider getting out of bed to worry about. The ones that pay money
generally get a response within a day, and the ones that don't pay me anything
will probably get a response when I get around to it. That, also, has worked
perfectly well for the last five years.

So while it did in fact turn out that I had a "crisis" at 4am while my wife
was giving birth, it was in no way a priority for me to do anything about it
just then. I had much more important things on my mind. Putting off the
disaster recovery process possibly led to losses in the two, possibly three
figure category. Fortunately as a single founder, that's the sort of decision
I get to make all by myself.

~~~
garrettdimon
That was one of the points of the article. At first, that fear dominated my
life. As time has gone on, and a few things went wrong here and there, I've
learned it's not quite that bad.

Also, we have a very different view on customer service. I strive to respond
to all customers immediately. We could reply within a day, but going above and
beyond for customers is important to me. The support requests in the middle of
the night aren't even a problem. It's just part of the gig.

~~~
jasonkester
_Also, we have a very different view on customer service_

Indeed. Though going above and beyond is important to me as well. We just seem
to have different ideas about what that means too.

I think patio11 says it best:

"I appreciate that you'd feel safer going with Brand Name X, and Brand Name X
will indeed have someone around to answer your phone call at 2 AM.
Unfortunately, they won't be able to do anything for you. Their only job is
getting you off the phone before you can speak to someone capable of resolving
your problem, because those people cost money. And you know what happens if
you call at 2 PM? You get the same guy."

As in, you might not get a response for 16 hours, but when you do it will be
from me, the guy who built the thing. And it'll be to tell you that your
problem has been solved and no further action is required on your part.

Incidentally, I don't have email on my phone. Nor do I carry my phone around
most days. I sometimes go a few days without checking email while on vacation,
and I'm on vacation _a lot_. If I could give you one piece of advice, one
solo-founder to another, it would be to figure out what you can change about
your product so that you can do the same. It's entirely your gig, so it's up
to you to choose whether anything unpleasant is part of it.

~~~
garrettdimon
I hadn't heard it put that way, but that's definitely a good point. My view on
all of this is still evolving, and we're getting to a point where it's not
going to make sense for me to the primary person on support. As far as above
and beyond, you're definitely right. It's all relative. If that part of it
bothered me anymore, I'd probably look to make some changes, but oddly enough,
I enjoy it, so it's not too big of a deal to maintain that kind of turnaround
time.

For us, the biggest change was adding an awesome system admin to the mix on
retainer. He's been a huge help and we now have a much more resilient
architecture. It's all evolving though as I find time to streamline the
processes as needed.

All definitely some good food for thought. Thanks!

------
wheels
Biggest lesson from the days where I was the only technical person in our
company:

Get a monitoring system in place that you trust. Then get a second, completely
independent one in place that you trust. Then also get on-machine monitoring
(monit, et al) that tries to fix things if they go bad.

In retrospect, that should have happened a lot earlier. Once we had redundant
monitoring systems and a firm belief that if something was down that I'd be
notified about it, the world became much more chilled out. If I didn't have an
SMS, the services were up and running.

~~~
jvoorhis
" If I didn't have an SMS, the services were up and running."

I wildly agree. I'm more apt to deploy a second monitoring system than replace
one. I don't worry until it reaches the PagerDuty threshold.

------
patio11
I was once under the impression that selling web-enabled software was a stupid
decision as a solo founder, because it would tether one to a server and uptime
problems. I have since found that this is not the actual nature of the world,
and that there are many, many reasons why web apps or similar server-dependent
software are probably the sweet spot for solo software-product-writing
entrepreneurs.

If you're thinking "That sounds like an ideal gig but the technical support
burden / server maintenance / etc will crush me", as me for specific
elaboration, but in general this is _much_ easier than you think it is.

~~~
tomjen3
How can you say that when you also talking about taking calls from customers
in the middle of the night? That would be pretty bad for me, at least.

~~~
garrettdimon
It sounds like this was a question for me, but it looks like a reply to a
different comment. I actually never take calls, especially in the middle of
the night. :) Sometimes, I'll email customers and ask if they'd like to chat
on the phone about their ideas, but phone support isn't realistic for us.

I do respond to emails if it seems like the customer could really benefit from
a response, and even sometimes when they aren't looking for a response.
Sometimes, if it can wait, I'll go back to sleep and handle it first things in
the morning.

~~~
tomjen3
Nah, it was memt for patio. I stalk him om here so the taking phone calls was
based on another comment he made elsewhere.

------
griffordson
I was in this situation from the summer of 2008 until about a month ago. I'm
just now starting to feel the relief of having another technical person to
bounce ideas off, and eventually, to be able to take time off without worrying
that the servers could go down at any minute.

Being the one person responsible 24/7 for a web app that can not go down is
incredibly stressful. Doing that year after year is no joke. I think it
changes your life as dramatically as having kids does. I'll never look at
technical decisions the same way again, even though I know things will be less
stressful in the future.

There were many low points and I know if I didn't have cofounders and
customers depending on me, I likely would have quit and found a "normal" job
several times over the years.

But I can't even describe how satisfying it is to be able to make the lives of
customers just a little bit better every time I check something off my todo
list. I'm not curing cancer, but I also have a much closer connection to the
work I do and the impact it has on the lives of real people than I ever have
before. And our customers are amazing and very appreciative of the work we do.
We've had many tell us that they'd quit their businesses if they had to go
back to the days before they had our product. That makes all the stress and
many, but not quite all, of the sacrifices worth it.

If you can, definitely find another technical cofounder from day one. But the
reality is that many businesses just can't make that work without
supplementing revenue with consulting or from some other source.

Congrats and good luck Garrett! Thanks for sharing your story.

~~~
lsc
>Being the one person responsible 24/7 for a web app that can not go down is
incredibly stressful. Doing that year after year is no joke. I think it
changes your life as dramatically as having kids does. I'll never look at
technical decisions the same way again, even though I know things will be less
stressful in the future.

I think you might be exaggerating about the kids, (I mean, I don't have any of
my own, but I'm the oldest of 6... really quite a bit older than all but one
of them, so I think I have some idea as to what is involved.) but I really
agree with the rest of that. Everyone that makes technical decisions should
have to take a turn on the pager.

~~~
griffordson
I've been a parent since I was 18 and I have 4 kids. I don't say that lightly.

I've also been on pager duty before. But being the only person responsible for
keeping a critical system running for years on end is an order of magnitude or
two worse than standard page duty I've ever done. I should add, our business
is very seasonal and very unpredictable.

~~~
lsc
> I've been a parent since I was 18 and I have 4 kids. I don't say that
> lightly.

Now, /that/ is impressive. I mean, yeah, I'm not impressed by the pager. I've
been on pager more often than not from 17 onward. But, I don't have kids, and
my significant other is also technical, also works a lot and is super
understanding. (well, and it's really only been the last five years or so that
I had a relationship I cared about more than my servers, anyhow. Maybe less
than that. I like my servers a lot. and I think there is a trial period for
partners.) - I mean, that's the hard part about pager for most people; "hey
honey, I've gotta stop paying attention to you, bring out the laptop and fix
something real quick" and that isn't all that much of a problem for me. I've
never really been a 'planner' so getting high priority interrupts isn't a huge
problem.

but yeah. juggling that /and/ kids would be tough. well, kids in general would
be tough.

eh, have you ever been the only technical guy at a company? I think it's a
pretty similar experience. Either way; being a sole founder, and being the
only tech guy at a company is way easier (assuming you have the skills and
power to fix the system so that you don't get paged more than once a week)
than being on pager on a giant and seriously broken cluster for other people.

I've worked other places where the pager went off three times an hour. Sure,
you only had one week out of four, and only 12 hours a day, but if you fucked
up even a little bit, the company would lose hundreds of thousands of dollars.
It was a completely insane situation, and completely broken, as it should have
been pretty easy to automate most of what we did. (most of what we did was
telling the cluster 'okay, don't use that node, it's broken') Now, why didn't
we fix it? I dono. there were some sharp folks there. Maybe we were all too
burnt out from pager? maybe it was internal resistance to just throwing nodes
back to our (really shitty) burn-in routine? (I mean, the idea was you were
supposed to log in to the broken node and troubleshoot rather than just
pulling it. But realistically, you only did that for the first day or two.) In
the end, most of us ended up leaving.

This was the only pager that has phased me. Out of being on pager more often
than not more than 20 years (well, uh, I guess it was closer to 15 years at
that time) that was the only job where the pager broke me. Really, that was
the only job where the pager bothered me much at all.

But yeah, compared to that? being a single founder is super easy. I get to
make all the decisions, so I can choose things that break less. I can take all
the shortcuts I like, and avoid the shortcuts I don't like. If the system is
unreliable, it's completely my fault. If I want to take a pay cut so that I
can hire someone else to lighten the load? my decision.

I mean, it's kinda like being the only tech guy at a small company, but you
have a whole heck of a lot more power, so you can make decisions like hiring a
customer out of IRC to help you out, which the boss almost never approves.

>I've also been on pager duty before. But being the only person responsible
for keeping a critical system running for years on end is an order of
magnitude or two worse than standard page duty I've ever done. I should add,
our business is very seasonal and very unpredictable.

I guess my main point is that normal pager (when you are the only/head
sysadmin) has all the responsibilities of being the single founder on pager,
with a whole lot less power to fix the root cause of those pages. Being the
new guy in a large organization usually gets you a little bit less
responsibility, (not all that much less if you've sold yourself as some kind
of super-expert sysadmin, or at least, that's how I felt.) but very little
power to actually fix root causes.

Personally, I think the power to fix the root cause makes the job incredibly
easier, and incredibly more interesting and satisfying. Otherwise it feels
like you are just playing whack-a-mole with the problems. Nothing bothers me
quite as much as fixing a problem without knowing how I fixed it.

~~~
michaelt
> I mean, yeah, I'm not impressed by the pager. I've been on pager more often
> than not from 17 onward. [...] Out of being on pager more often than not
> more than 20 years [...] that was the only job where the pager bothered me
> much at all.

So how does pager duty work with your employers? Most places I've worked have
asked for a 15 minute response time (which effectively means being within ~12
minutes of home) and being sober. That means no going for a bicycle ride or a
run; not going on dates, to restaurants, the theatre or cinema; not visiting
friends or relatives; and not going to the gym or going swimming or going out
dancing.

Doesn't pager duty basically mean you have to sit at home on the internet for
all your free time?

~~~
lsc
Fifteen minutes is... kinda a long time for logging in and checking things
out. The thing you miss, though, is that there are all sorts of devices with
which I can log in.

I have ssh on my cellphone which is on my person at all times, and while doing
anything involved is difficult, I can usually verify that there is a problem
and it's nature, and if it's easy, I can deal with it then. But that satisfies
the 'respond in five minutes' or whatever. I responded, I can tell people
involved what's up and how long it's going to take me to get more info.

The next step up is my laptop, which usually stays in the car. I jog to the
laptop, boot it up, use the cellular modem dongle thing, and it's about as
good as being at home, most places. I have a cheap inverter in the car if my
batteries are low.

If I'm willing to take a social hit, I can also call someone else and say
"Hey, I'm drunk to the point where I can't handle root, or I'm 20 minutes out
and my laptop took a shit. X paged me. can you deal with it?" and repeat until
someone says yes. I look like a fool in front of my co-workers, but eh, the
problem gets solved, and everyone does this every now and again.

(This is the big problem with being a sole founder. You can't just call up a
random consultant; you need to know the system to be able to fix it. It's
really nice to be able to call two or three people that know the system well
enough to help you out in these times. In this case, I think even someone that
doesn't have a lot of experience but is willing to be trained, and that you
can afford to pay often enough that your system is fresh in their mind, is
better than just calling someone really good that doesn't know the system when
the system is hoarked.)

So yeah, I can go to movies. I might need to walk out of the movie, but I can
go. Restaurants are easy; I don't even have to leave; I just whip out my
laptop and fix what needs to be fixed. dancing? same deal. Yeah, I look like a
dork or an asshole if I get paged and I whip out the laptop in the middle of a
social engagement, but honestly? I'm not sure that really changes anything.

Really, anywhere I can take my laptop that has cell reception and power, I can
go. I mean, I know I might get interrupted, but I probably won't be.

The hard part is really the mental state. You really want to make sure you go
to bed before you are exhausted, because problems that take five minutes when
you are fresh can take, well, much longer when you are not. Alcohol too; I
find that the DMV limits are reasonable, and if I stay under those I can
handle myself (on a computer; I'm a little more conservative when it comes to
driving, as I'm a pretty shitty driver to begin with.) Sleep, really, is the
problem I struggle with, but I have a hard time keeping a schedule anyhow.

(Oh, also, the 20 years is clearly a lie. I'm what, 31? something like that.
and I think I got my first pager at 17, so considerably less than 20 years.
For some reason, this week my sleep schedule has been pretty messed up, and I
haven't been mentally 100%. I've been writing a lot, and writing poorly about
stupid bullshit that doesn't matter. Odd.)

~~~
davidandgoliath
The life of a hosting company owner in a few brief paragraphs. "Me too" would
be fairly easy to state, albeit slightly different: I had my operation when I
met my significant other and as a result have a fairly varied and flexible
schedule.

Overall I think she enjoys that, adding a child to the mix has been fun &
surprisingly hasn't changed much at all -- in the first few months it gave me
an even better excuse to be up at 4 in the morning.

I've been at this for about ~6 years as a solo guy (albeit, with hires -- so
that changes things entirely) and a few years prior at other companies in
slightly lesser capacities as an admin.

Which reminds me, I need to get back to you one of these days.

------
abcd_f
I did exactly what title says for 18 months. 3 million users, about 20%
simultaneously active, 5 servers. Not a web app, but an online service
nonetheless. Programming, design, support, scaling the damn thing, busdev,
support, marketing, scaling, sales, support, IT matters, support, scaling, OEM
version, support, scaling, dealing with fraud, support, support. Fun times.
Never again :)

~~~
jbigelow76
You can't leave us hanging like that. 3 million users? We need deets (please)!

~~~
abcd_f
Sorry, I like my privacy. And it was more of a viral accident rather than a
result of clever marketing and precise positioning.

------
dangrossman
I've been on-call for my webapps 24/7 since I was 18 and started offering
subscriptions. I'm 27 now. I have never truly taken a day off; even on
vacation I'll have a laptop in the hotel room, and a phone with me to get SMS
alerts of any failures.

~~~
ThomPete
Wouldn't you have some sort of ability to outsource some of it?

~~~
lsc
eh, the stress of pager depends a whole lot on how often it goes off; I've had
people that could take pager for the last two years, and haven't put them on
it. I take pains to see to it that the pager doesn't go off often, and eh, I'm
not paying enough, really, to expect that out of others.

I mean, this is what being a SysAdmin is. Something is very wrong if you get
paged more than once a week, but you carry that pager all the time. It's part
of why we pull down real programmer money with only a subset of real
programmer knowledge.

I've got a cellphone with extra batteries and a Verizon dongle thingie that
can get me online from just about anywhere, so it's really just the power I'm
worried about. Sometimes I carry extra laptop batteries.

For me, the biggest problems have been when I was paged when exhausted, sleep-
wise. A few times I've had to hand off because I was in that state. (I've had
a problem where I handed it off because I needed to sleep, then Nick handed it
back to me in the morning because he needed to sleep.)

So yeah, having someone else is pretty important, I think, and worth waiting a
few more years for the 'real money' payout, but eh, if you are doing it right,
you can be front line pager forever without too many issues. (that said, I'm
going to a family reunion soon, in Montana. probably the farthest away I've
been in a while, and certainly the longest time I've spent on a plane. Nick
will be primary on pager.)

------
njx
I am in the same boat. I am the solo founder of Infocaptor and Mockuptiger.
Lot of times I wish for a co-founder with whom I can bounce off ideas and
plans to take over the world. Sigh...but on the flipside it gives tremendous
sense of responsibility.

Automation and monitoring is crucial when you are solo founder. Think about
automating every little thing that takes only few minutes to do but the
budgeted time is 5 times of actual time it takes to finish it.

Outsourcing, automation and dashboards are your friends. I have either
outsourced majority of my activity or automated it.

But the problem with running startusp is the task list keeps changing every
day and is like a bottomless bin. Everyday you automate something and you keep
finding new things to do.

Healthy work and life balance is so crucial. Due to stress at one time had to
visit the emergency department, glad it was just "Stress increasing the
acidity" and wife had all the reason to take control of my routine (just few
days). After that episode, I immediately put breaks on all the stressing out.
I realized there was simply no need of making things happen all at the same
time.

I put back my meditation routine on track ( avg 2 hrs/day) and that has helped
so much in terms of health and clarity (plus other things). I recommend
everyone who wants to be involved in startups to start meditating. It will be
a huge favor for your family and yourself.

Goodluck and cheers to all the solo founders!

------
einhverfr
Yeah, trying to switch my business here from self-employment mode to startup
mode (and hence moving from consulting revenue as the big thing to scalable
revenue as a big thing, though consulting will stay for reasons of business
strategy). The big thing I am doing first is trying to get a co-founder on
board.

This has actually been an interesting process. I came up with three people,
had one in mind as an ideal candidate, and approached all three. My idea was
that if others really worked out, we could go with more than two people. the
top candidate and I are still talking, but the other two never went anywhere.

There are a bunch of reasons for this. First it is easier to apply for funding
if there is a team, but more importantly having a second individual provides
needed feedback and makes total screwups a bit less likely. It is _always_
important to keep folks around who will give good, honest, and occasionally
brutal feedback. Nowadays I am not even sure we will apply for funding. We
might bootstrap.... But getting a team in place is for now the _critical_
task.

So I completely agree with the article's conclusion that he would have tried
to get a co-founder if he did things differently. This is _so_ important to
do.

------
bdunn
As a new solo founder, who also gave up running a consultancy to build a
project management product (<https://planscope.io>), this post REALLY
resonates with me. A lot.

I'm bootstrapped, and don't ever plan on outsourcing anything - except for
maybe writing blog posts. But the feeling of needing to be close to a phone or
Internet connection at all times in case of the inevitable really concerned
me.

But then I sat back and breathed - downtime happens. It's not the end of the
world, my customers will survive. I've recruited a close sysadmin friend of
mine to be on call should anything ever happen, who I'll pay per incident. But
that's it, life is too short to worry constantly and be glued to your phone
while with your family or loved ones.

~~~
garrettdimon
I would say that deciding not to outsource anything is a mistake. We regularly
turn to great people to help with some JavaScript features or systems
administration. We've even had some folks help with Rails work a couple of
times.

Thus far, without being able to hire full-time, outsourcing that stuff was the
best decision that I've made yet. It enabled us to launch some features that
might have otherwise taken me forever to get around to building.

------
dm8
On a side note, you should not use Lobster type face for content. It looks
"hip" for logos and all. But it becomes annoying for content.

~~~
jbigelow76
I thought the quality of the content outweighed the cliche type face selection
(but my initial reaction was to the type face as well).

