
Confessions of a 20-Something Startup CTO - BenjaminCoe
http://bencoe.tumblr.com/post/28287898568/confessions-of-a-20-something-startup-cto
======
makmanalp
>I’ve always struggled with confidence issues. As a way of compensating for
this, I leaned on my programming licks; here was at least one thing that I was
awesome at. >When I got into the startup world, something shocking happened. I
started to meet people who were my equals, or even worse, better than me! This
caused an existential crisis.

Spot on. It's not just you, buddy.

Edit: Contrary to popular naysaying, there _are_ some of us who do like
reading about others' trials and errors. I also loved the article on rock
climbing. Keep it up!

------
wensing
When you say that "Bootstrapping a startup is stressful", are you only
referring to the time before you raised the $2.5 million? How long was that?

EDIT: According to CrunchBase you raised $500K two months after your company
was founded, and another $2 million 13 months later. I'm sure you just used
the word without thinking much about it, but technically you bootstrapped for
all of 8 weeks. :)

~~~
modarts
Why is there this overwhelmingly anti-bootstrapping sentiment present in the
startup community? What's so wrong with taking outside funding?

~~~
j_col
If you take outside funding, you're _not_ bootstrapping. According to
Wikipedia:

"Bootstrapping in business means starting a business without external help or
capital."

Source: <http://en.wikipedia.org/wiki/Bootstrapping#Business>

There is nothing wrong with taking outside funding, but then you don't get to
call it bootstrapping any more (as per the widely-accepted definition above of
what the term means).

This is mixing up terms.

~~~
modarts
I should have clarified that I was trying to ask a more general question as to
why bootstrapping is seen as a superior way of starting a company as opposed
to taking on funding.

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chayesfss
Ahh, I remember when I was 20 & how nice to think what you have to say is
important. I've personally found that people want to read about functionality.
They might want to read about your personal stress after you've become
successful but chances they're more interested in reading about a new
integration or how to look at something different.

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tkiley
The "MIT syndrome" thing is crucial. I think the most important trait in a
startup leader is humility. To build a kick-ass sustainable company, you
absolutely, positively must be comfortable working with people who are (in
some or most respects) smarter than you.

Also, I find it very interesting that the "high" of this roller coaster is the
funding.

~~~
dkrich
I never understand why funding seems to be the end goal either. To me, apart
perhaps from some vindication of your idea, the happiness people experience
when funded almost shows a lack of vision.

~~~
BenjaminCoe
For people with financial burdens, venture capital can be the difference
between being able to pursue your startup dreams, or letting them die on the
vine.

There are definite downsides to raising money, and I totally understand the
stigma the HN community tends to attach to it.

Having said that, a 500k seed investment let Jesse and I put down everything,
and put 100% of our efforts towards Attachments.me. I have no regrets about
this.

~~~
dkrich
I'm not debating the merits of raising cash. Most companies and businesses
have to do it when starting out. The part that I (and I'm assuming the OP)
find puzzling is the part about "climbing to the top of the hill overlooking
the city and realizing all our childhood dreams had come true" after having
raised a round of investment. This seems to me to be saying "we got a million+
investment and we won!" I think for most that's not really the point of
starting a business.

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k33n
Thanks for writing this. As a 20-something startup CEO, I frequently want to
write about something mundane (or not) but often choose not to for reasons of
confidentiality or that I worry some things will cause problems for me later.
I don't think I'm a startup god, or an expert at all. Sometimes it would just
help to vent or have a discussion about something with strangers who are in
similar positions as me.

Unlike some of the other commenters here, your post didn't strike me as self-
important. Just looked like you felt like sharing and wanted to have a dialog.

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awm
Could you elaborate on what you mention is the MIT syndrome? I saw one
definition (based on over explaining) but it seems like this is something else

~~~
GuiA
Students entering MIT are the ones acing every class, being constantly praised
by teachers/parents and feeling better than everyone else in high school. Then
they enter MIT, where they find themselves with hundreds of fellow students
just like them.

For a lot of personalities, this leads to depression and even in some
instances suicide.

~~~
Xcelerate
I would think the fact that they are one of hundreds out of billions would
inflate rather than deflate the ego.

~~~
mquander
That doesn't make sense. People emotionally calibrate themselves against the
visible skills of the people in their peer group, not a global distribution of
IQ.

~~~
Xcelerate
Yeah, I know they do that, but it doesn't make sense to me why they do that.
If everyone expects to be #1 in the world, everyone but one person is going to
be disappointed.

~~~
ajdecon
It's not a rational thing, but more instinctive. Your immediate surroundings
influence you in all sorts of unconscious ways, but all the people in that
global distribution are pretty abstract. You can quote statistics all you
like, it's difficult for them to change how you "feel" about yourself.

Also <http://en.wikipedia.org/wiki/Dunbars_number>

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fellowshipofone
Thanks for the post; running a company is not only about making the right
decisions, it is also about living with the bad ones. I think this blog post
is a good testimony that helps with that.

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dennisgorelik
I don't see much traction here:

<http://siteanalytics.compete.com/attachments.me/>

It looks like aqui-hire is the best option for attachments.me

~~~
BenjaminCoe
Our main products are a Chrome Extension, and an iPhone application. The
website itself gets a, granted small, but growing amount of traffic -- but
it's mainly just there to direct people towards the clients.

I don't think that Alexa or Compete do a perfect job of reflecting our usage
numbers, since the website itself is not the main way people interact with us.

~~~
dennisgorelik
1) Compete shows downtrend for attachments.me I understand it could be a
mistake due to low numbers, but still does not look promising.

2) What are attachments.me actual usage numbers today and 1 year ago?

~~~
BenjaminCoe
I won't give you all of our numbers, but If you look at our Chrome Extension
page, you can see that we have 35,000 active installations. Much of this
growth has happened over the past six months.

These numbers simply aren't well reflected in the Compete score.

My coworkers and I work hard, and believe in what we're doing. Rome wasn't
built in a day, let's hold of on the talent acquisition talk ;)

~~~
nanijoe
35k active installations does not sound like a lot, especially for a free
download.

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hkon
I think IT is more like confessions on anyone starting out at anything. Tanks
for verifying what carnegie said.. 100 years ago ;-)

------
larrys
"I began getting depressed about the lack of a life I had outside of work. I’d
bring this bad mood to work with me, in turn making it a worse place to be.

I’ve since made an asserted effort to dedicate time to my social life: going
on trips with friends; going on dates; and, most importantly, getting work
completely off my mind occasionally."

Serious question (and my thoughts) here I'm not trying to be cute. Regarding
your "social life".

Do you think you will grow out of this? Because what do you think is going to
happen if/when you are married and have children and aren't living in SF or
some exciting place and have much on your plate?

The best way to insure that you can live the life you want and have some fun
is to put all the effort in that you can now and try to put off having fun
until a bit later on. Now is when you have energy and should be able to work
non-stop with very little else. (I didn't surface for air for 7 years working
6 to 7 days a week ..)

I point this out also because the world is littered with people who didn't get
into a good school because they spent a bit to much time worrying about
missing something or having fun and are paying for that later. I'm sure you've
met people like this in your high school.

It's a little unclear how long you worked before you realized what you wrote.
It was certainly less than two years since you wrote this: "I’ve grown a lot
as a person in the past two years." That's not a long time to be denied the
pleasures of other people and fun (look at people on tours of duty in the war
or speaking of my own experience).

The fact that you never had a problem until later means you really haven't
dealt with the situation you are in now in the past which I think is what you
are saying. Things were easy for you until you got around a group of people
who were also good. I know first hand about the MIT syndrome since I saw
others that suffered from it at the school that I went to which was quite
good.

I didn't suffer from that for one simple reason.

Things were never easy for me it always took hard work and it also took plenty
of effort for me to get into the school I went to. So when I got there I
didn't fall apart if I got a "B+". I just kept chugging away while the ones
who were "so much smarter" who got in with their top grades and SAT's wilted
under the pressure of having to do so much work. This was a long time ago
compared to when you are in school. So to answer your question, no, things
haven't changed that much.

You've got plenty of time to have fun. Now is the time to work as hard as you
possibly can with minimal breaks in order to achieve your goals. You might not
surface for air for a few years but it will probably be well worth it.

One last thing. There will be times in life when you might have some crisis
either in personal life or business that will require you to work all the
time. I had a case where several of my top people left, I was in the middle of
a legal case, and a breakup, and I still had to show up to work doing the job
of three people and deal with personal issues and family fights. Having to go
through that and knowing I could (similar I'm sure to having climbed a certain
mountain like you are doing) was a great experience that made me realize that
I didn't have to be scared of the unknown and that I could handle it.

~~~
lazerwalker
> The best way to insure that you can live the life you want and have some fun
> is to put all the effort in that you can now and try to put off having fun
> until a bit later on. Now is when you have energy and should be able to work
> non-stop with very little else. (I didn't surface for air for 7 years
> working 6 to 7 days a week ..)

There's a flip side to the coin, though: your opportunities for 'having fun'
are very different as a twenty-something living in a big city than as someone
who's married with children in a less exciting locale. Many older people
successfully start companies; far fewer stay out partying with their friends
until 4am or go backpacking across Europe.

I'd argue you can find a balance. You shouldn't piss away your youth and your
potential, no, but life's too short to spend it perpetually saying "I'll have
fun later" because one day there won't be a later. Especially since working
insane hours is usually a game of diminishing returns: while you might have
been able to spend 7 years working your ass off 7 days a week, most normal
people burn out, even the most driven and brightest of 20-somethings.

~~~
larrys
"most normal people burn out, even the most driven and brightest of
20-somethings."

What's really important is making sure you are getting enough sleep and
exercise as well as eating correctly (although that's more of a long term
thing). Those are the few things to me that take priority over working.
Because without that (sleep and exercise) the working hours are much less
productive. And without your health you have nothing.

------
electronous
This article might have a good point, but it's hard to find it amongst all the
"my friends and I are really cool and awesome people" speak.

Does this article, coupled with the fact that the author submitted it himself,
strike anyone else as terribly vain?

~~~
GuiA
Welcome to HN, where everyone is a rockstar entrepreneur!

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heretohelp
I'm a 20-something startup CTO, why do I want to read the thoughts of people
my own age instead of people who are more experienced?

~~~
WadeF
A lot of times people more experienced are so far detached from what you might
be going through.

I've found people who have just gone through what I've gone through can help a
ton.

Joel Gascoigne sums this up better than I.

[http://joel.is/post/28198804700/why-im-helping-startup-
found...](http://joel.is/post/28198804700/why-im-helping-startup-founders)

~~~
larrys
"A lot of times people more experienced are so far detached from what you
might be going through."

Some of those people may have gone through the same and can offer their
opinions of how it worked out for them.

Have you ever had a medical problem and asked an older person about it? They
might tell you "don't worry I had that same pain and it went away, no biggie".
Don't assume someone older has no experience or empathy to what someone
younger is saying.

~~~
WadeF
I wasn't. Just simply trying to provide a perspective on why someone younger
might also have valid advice.

Life doesn't have to be one or the other. :)

