

Why I'm Doing It All Wrong - ZanderEarth32
http://danshipper.com/why-im-doing-it-all-wrong

======
oz
Solid, solid post.

For _years_ I held to that mentality of "drop out of school, and do big
things." I dropped out after 1st year of CompSci to to work at a telecom
startup back in 2006. I was eventually fired and floundered for a few years.
I'm in a good place now, clients paying me real money while I work from home
in my underwear :). Life's good, and getting _so_ much better by the day.

But I was very, _very_ lucky.

In Jamaica, you can't point to potential employer to a GitHub profile. They
want to see your degree. And you don't have luxury of folding your arms and
saying, "Well, I wouldn't want to work for a company like that anyway." The
rent needs to be paid.

If I could go back 5 years, I'd finish school, and start a business while in
school, keeping it as a side project while I worked for a few years, got real-
world experience and saved some money. I'd be much better off now.

There is no shame in having a backup plan. There is no shame in choosing the
'easier' way. And don't bother with those wonderful fantasies of "burning your
ships." 'Tis a fool's errand, for the simple reason that in the Real World,
Shit Happens™

Dan is doing it right.

~~~
redrory
Hey oz, what a story. Another Jamaican here we should connect. Email in my
profile.

~~~
oz
Email sent.

------
jaf12duke
When Grant Hill was asked why he stayed at Duke for all 4 years instead of
jumping to the NBA after his freshman season, his answer was simple: College
is fun.

The single best response I heard from you Dan is that you enjoy school and you
enjoy bootstrapping Airtime. That's it. It's one of the things I love about
you--you spend a good deal of time in reflecting on what you actually want.
When you enjoy what you're doing, you should just keep doing it. When the
north wind blows and you're ready for something different, you'll go after it
then. The world will still be there, full of problems that need solving.

Doing startups in San Francisco is not some fleeting magical opportunity. It's
hard, it's stressful, and 99.9% of time doesn't end like Instagram did. And
you'll probably be doing it for the next decade of your life at least. So
there's no rush. We'll all be here waiting when you're ready.

~~~
juan_juarez
The basketball reference is a good one - even if you're the best player you've
ever known coming out of HS, the odds of making it in the NBA are obscenely
low.

Spending every weekend and vacation throughout childhood hacking really limits
your perspective on the world. Sure, you might get the inspiration to write a
GitHub that targets developers. Then you have things like Instagram, Facebook
& Basecamp that require actual life experience to understand the need.

Get out and experience the world, take the liberal arts classes, make friends
with 'normal people', get laid, work some shitty jobs The Man - whatever it
takes to expand your mind. There's a lot of things that a middle-class, tech-
obsessed geek just out of high school, no matter how bright, just doesn't get.

~~~
stdbrouw
> Spending every weekend and vacation throughout childhood hacking really
> limits your perspective on the world.

No disagreement there, but what kind of perspective on the world do a project
management app, a social network and a photo app require? Surely, there are
better examples out there.

~~~
eitally
Well, to be fair, a project management app designer should really have
significant project management experience, preferably in an enterprise
setting, since that's where things go plaid most regularly and spectacularly.

------
jc4p
This is an excellent post.

I'm somewhat in the same circles as you (friends with Wesley, working with
guys from Penn right now) and have been trying to make a decision on staying
in my mediocre school and getting a degree in what I'm interested in learning
(economoics/math) and dropping out of school and working full-time at all of
the companies I've gotten offers at in the last few years.

I quit a six-figure job last year to go back to school and now that I'm doing
summer work again I'm really regretting that decision, so I've been trying to
make my mind about this for a while. It's amazing to see how clear headed you
are about the similar situation you are in and what you have decided on. I'm
definitely going to consider it when I make my decision.

Thanks Dan.

------
jason_shah
Implicit in your description of the different paths you and your friends have
taken is an important fact: everyone's path to success is different. So is
their definition of success.

Dropouts have made it. Dropouts have failed. People who stayed in school have
made it. People who have stayed in school have failed.

Ultimately having conviction about what is right for you and not wavering with
the startup flavor of the day sounds like it will serve you well. It may lead
to a different path of success if these other opportunities involving you
dropping out pan out well for those companies that you could have been a part
of. But it in no way does it preclude future success or suggest that you won't
have your own homerun later. Excellent self-aware post, Dan.

------
ef4
Anyone who actually think's that's "doing it wrong" needs to step outside the
echo chamber for a while.

~~~
huggyface
This. It's like a straw man in a way. The vast, vast majority of people do it
this way. By every common criteria it is considered "right". Just because
Thiel got a lot of news for proposing an alternative idea doesn't justify this
ridiculous notion that doing otherwise is somehow contrarian. Quite the
opposite.

------
brandnewlow
Dan, just make sure you don't buy too much into the other side of things.

There's no glory in being "holed up in an office in Philly for $650 a month
working 14-hours a day this summer."

You don't get any special reward for doing things the hard way. Maybe you know
this. I sure wish I did when I decided to bootstrap in Chicago 4 years ago. I
made things really hard on myself thinking there was some special reward that
would come from it. Other than raising my tolerance for suffering and comfort
with extreme poverty, there really wasn't. And living on $1200/month made it
really hard to do good work. Again, this might not be your situation. But I
hear stuff like this from people when they explain why they're staying in
place X and bootstrapping what they say will be a big world-changing company,
and I wonder...

------
ansible
That is all amazingly wise and level-headed for someone his age. I am
impressed.

------
akrymski
I don't know if you're wrong or right, but I'll give a contrarian view cause
it may actually help you (instead of just nodding in agreement). Here goes:

Make sure you've decided not to go the YC route because you're afraid of
responsibilities it brings. Your first reaction may be - "BS!". But humans are
really good at coming up with logical explanations not to do something when
they're afraid, eg walking up to a hot girl in a bar :)

What responsibilities? Well running a "funded" startup means failure is
harder, you are committed to more employees, investors counting on you, and
the whole startup ecosystem waiting for you to hit it big or fail. There's
more pressure. By adding focus to your life, like saying you'll be an NBA
player, you've limited your options and failure now has a much higher
probability. College is a safety net.

I've started my first business in my last year of uni (DotHomes.com), raised
multiple rounds of funding before achieving a small exit and have learned
tremendous amounts. I've barely learned anything useful at uni though (and I
went to one of the best). If I was to do it again - I would start that
business before going to uni (something I considered at the time) because had
I been at least 2 years earlier into my market - my chances would be a LOT
higher. (eg at the time barely anyone did SEO in that space, by the time I
launched getting traction was 3x as hard). Things have worked out alright tho,
I've been accepted into YC since, working on post.fm, but it doesn't mean it
was the optimal choice.

Success is more a function of being in the right place at the right time.
Smart people are those that are able to establish what that place will be
TOMORROW, and move there. It seems like now the right place to be is YC /
Silicon Valley. If you believe bootstrapping is a better approach to building
a startup - convince your friends of it, and do it at YC. imo that's not an
excuse.

Nobody forces you to raise lots of money there, you could still bootstrap if
you want to, but life is a race against time. Industries, like economies, move
in waves / cycles / trends. Steve Jobs was "lucky" to ride the PC trend, had
he decided to do that 10 years later - he may have been too late, no matter
how genius. Perhaps the Google guys could have done something else, but the
search opportunity window would have closed, and that other thing would
probably be not as big.

I don't believe this "startup ecosystem" will be around forever for you to
pursue. Nothing is. We still live in a world where markets dictate the next
boom or bust. I've had a major exit fall apart because of the 2008 market
crash. My point is - the world doesn't stand still. Like in poker there are
times when you have to go all in if you want to be one of the best. Your
friends went all in. You didn't. I bet Paul appreciated the fact that they
were persistent. At this point in the startup wave - they've made a sensible
decision because they've got a good hand (if YC accepted them). Maybe your
time will come and you may have a good hand in the future as well, maybe not.
But making things harder for yourself isn't a recipe for success. It's a
recipe for geeks who like to tinker with things without finishing them (and
god knows I've done that too many times) because they enjoy the process too
much.

In fact bootstrapping is just that - giving yourself a longer runway to do the
stuff you love. You probably don't love hiring, managing, presenting,
pitching, etc - all the stuff that CEOs and not developers have to do. Once
you have a product/market fit the only reason NOT to pour gasoline on your
fire is if gasoline is too expensive. Right now that's not the case.

The risk / reward for your friends is now very good. Even if they don't hit a
homerun - they'd have learned so much doing it, it's worth infinitely more
than uni. Life is short, be bold, you have nothing to loose, and you can
probably always go back to college. If you never find the courage to talk to a
chick that's a "10" - you'll never be dating one. And as years pass, you only
get older and more conservative.

This will probably generate lots of downvotes, but I thought I'd rather give
you the other side of the coin just in case you're not being honest with
yourself. Of course it's a lifestyle choice and there's no right or wrong, nor
am I remotely the expert. But I'd give anything to be 10 years younger right
now.

------
jonmurray
The 'raise a lot of money and swing big' is very much a silicon valley way of
thinking. It's not necessarily wrong, but it's definitely not the only way,
and not the right path for every entrepreneur / business.

I had a lot of smart people tell me early on that my last company was a waste
of my time because the opportunity wasn't large enough. Large enough for whom
though? Hearing all that feedback was incredibly discouraging when I was
starting, but I passionately believed that I was right about the opportunity
and the value we could create, even if it may never be a billion dollar
business. So, I hired a co-founder, recruited a very small core team, worked
24x7 for 18 months, and we were acquired. At the time we sold, we actually had
pretty reasonable Series A terms sheets on the table, but we decided selling
was the right path, for a number of reasons.

Many (definitely not all) silicon valley investment types would probably look
at that and the amount we sold for and assume the company was a failure. I had
a lot of people question not going the VC route at the end and trying to blow
it out (many of these doubters were the ones who doubted going after it at all
initially). I would have done it if I thought it was right for the business,
but it was not. And I now own a home in Marin (and one in Sonoma), my kids are
in private school, and I just don't worry about the shit I worried about 10
years ago. My life is radically different and better. AND I had an incredible
experience creating a real business, learned a ton, and am a far better
entrepreneur now than I was when I started.

Now I'm back at it, and swinging much bigger this time, but with that
experience (and added confidence) under my belt. We actually just did YC (it
was awesome), raised money, and are going after a massive opportunity. But I
think it's right this time, for this founding team, for this opportunity.

The best professional advice I ever received was from Chris Moore at Redpoint
Ventures. He told me a few years before my first startup to think about my
career as a process, and not to be so focused on just jumping to the end
point. For me, this was the right advice at the right time. I wouldn't be
where I am today had I not accumulated a number of experiences along the way
which helped me to succeed later. Everyone's different. Explore your passions,
but also be true to yourself. Know who you are and what you want. And surround
yourself with smart people to bounce things off - but just be sure to treat it
only as input. No one can tell you what you should do.

Also, there's just no shame in creating something that's 'smaller'. You are
right to not give a shit what other people think (and it probably helps that
you're in Philly in that regard). There are a ton more buyers of companies at
$10MM or $20MM than there are at $250MM or $500M. Hell, even an exit for a
couple million can really change your life (with the right cap table). If you
raise a shit ton of money because "that's how things are done", you are most
likely shutting off any early exit (at least, in a way that will be meaningful
for you). So, just be sure it's the right thing for you and your business, and
don't focus too much on what other people think is the right path.

------
jermaink
In my past I worked in a small racing team in Germany. Still young, there were
two things I learned from my co-pilot who was a known race driver in the late
80s:

1\. 'It's not the speed that kills you, it's the sudden stop.'

2\. 'always better, never perfect.'

It took some while until I understood that the petrol head was a better
philosopher as I thought.

Might be that you discover tour own thoughts in these two quotes too?

~~~
kbronson
Related to 1: "It's not the bullet that kills you, it's the hole".

------
edw519
The best advice my mentor ever gave me, "When all is said and done, you still
have to go with your gut."

It's so easy to get caught up in the frenzy of "start-up culture", "easy
money", and "herd mentality" that we often have to make an effort to stop and
tell ourselves, "Wait a minute. This doesn't make sense."

Sounds like you're really going with your gut, Dan. Keep up the good work and
the great writing. I, for one, have great hope for your "sustainable happy
ending".

------
mwd_
Realistically, chances are that if you could come up with a good idea for a
startup and successfully follow through before university, you will still be
able to do it a few years later. Even if the startup world implodes, you'll
probably just have to wait a couple more years. I would guess that the added
education improves the odds for most people, and failing a startup with a
degree and related career to fall back on its far better than the alternative.

Aside from university being fun, you should also be learning skills and
meeting people. I'm working for a startup that started at my university and I
heard about it through another student. If I decide to do a startup one day
I'm guessing my experience and contacts will be an asset.

~~~
larrys
"Realistically, chances are that if you could come up with a good idea for a
startup and successfully follow through before university, you will still be
able to do it a few years later."

True but you also have to consider the people you know who might be able to
help you. If your friends are leaving [1] to do something (and you believe in
it) then that opportunity may never present itself again. Having close
relationships with the right people you know well and can trust is important.
You can't just establish that on the fly (think of any girl you have ever
dated and how the relationship changes over time as an similar example).

[1] Or if it's your idea and they will leave with you.

------
trentonstrong
This post really really resonates with the thoughts bouncing around in my head
currently.

In the current environment (at least where I am) of well-funded startups with
no shortage of benefits and work/life balance, a lot of people will think
you're crazy for not taking advantage of it.

I personally like the closing sentence:

"Interesting indeed. And somehow, I have a feeling that it’s all going to work
out in the end. For both of us."

While optimistic, it reminds me that try as we might to codify and generalize
all the ways to be successful in business, your own personal heuristic
approach is all that's going to matter in the end.

~~~
dshipper
Thanks for your thoughts. "Your own personal heuristic approach is all that's
going to matter in the end." I absolutely 100% agree.

------
francov88
Great post. the part that stuck out the most personally:

"Homeruns by definition aren’t sustainable. They’re not predictable. Sometimes
you hit one, but most of the time you don’t. That part of things is mostly out
of your control."

This is very true and I think lots of folks in the startup scene have adopted
herd mentality - but I believe there are advantages to both methods (dropping
out+raising or building in a sustainable fashion). It all depends what fits
with your ideals.

Either way, I think it will all work out. I've worked on my own businesses
since I was 11 starting by mowing lawns and shoveling driveways in the winter
- and I wouldn't trade those experiences for any kind of "homerun".

In the end, it is the synthesis of your experiences that make you, and that's
the point of the advice to pursue all opportunies presented to you. A friend
once told me the best thing you can have in life are options.

Just keep your chips ready.

------
yason
Once again, the world is different for everyone. Following your gut feeling is
all you can do because no rational process will get you to the answer; it will
only get you the "whys".

What I mean with world being different for everyone is that you can't
extrapolate from someone else's experiences. Things that are just right for
him are possible totally wrong for you. And what worked for you probably
doesn't work for another guy. Dropping out of college to start a startup works
if it's right _for you_ : for him it was more important to slowly build his
own thing instead.

I feel so happy about people who do their thing, whether it's going with or
against the things other people do.

------
jonathanjaeger
Haha, well the title is definitely one to click on, but your premise is
essentially the opposite (or at least your path is different, not wrong, as
you mentioned).

Entrepreneurship is a path to solve a problem you're interested in, change the
world, satisfy your ego, work on your own, or dozens of other reasons why
people start companies. There's no right way, and even many YC companies are
going to fail. If you see a small idea that's a lifestyle business as a good
way to gain experience and get there quickly, it might make more rational
sense than being part of a YC batch. It just depends your priorities in life
at the time and what makes you happy.

------
sb1752
I love it. You acknowledge what others do and are fully aware of the culture.
Yet, you decide to go your own path. I really admire this way of thinking.
Don't just follow the crowd. I think its crucial, especially in these times,
to not just give in to herd mentality. Challenge everything, especially when
'everyone' is doing it.

A commenter here brings up a great point though. As long as you are doing this
because you think it will be better for you and not because of any fears you
might have, I personally think you're on the right track and will find success
and happiness.

------
lobotryas
>Funding can’t be counted on and so I’m not concentrated on it.

>Every successful business follows from solid fundamentals. Customers, money,
funding. And that’s what I’m concentrated on.

This part seems a bit contradictory. Funding "can't be counted on", but it's
one of the fundamentals that are "by definition sustainable. Which one is it,
Dan?

Also, if you're working in a small team, what are the advantages of spending
money to rent an office? Alternatives would be Hive 76, a team member's
apartment or a semi public space.

~~~
jkimmel
I believe he means that revenue needs to come before you seek VC funding, in
essence, he feels bootstrapping is a more sustainable business model. Though
it doesn't have the glitz and glamour of YC or a large bank account, Dan is
bright enough to realize that this funding climate won't always exist. If he
figures out how to bootstrap effectively, VC funding is that much easier in
the present, and he can keep going in the future when there aren't so many
angels out there throwing down fairy dust from Sand Hill Road.

------
mangoman
After reading that post, I feel like I'm doing it wrong. I figured I'd learn a
ton taking the hardest programming courses I could find, and yet I found it
striking that you're spending your time in school learning about making a
business. I suppose the foresight I thought I had is a little too narrow.
Maybe I can change my classes before the next semester starts and add a non-CS
class to expand my horizon. Thanks for the great post!

------
sharps_xp
I'm older than you in human years, but you're probably old enough to be my dad
in entrepreneur/developer years.

------
yonasb
Great post, I generally agree with it. But the homerun lure is too strong
right now. If it were me, I would probably step up and swing if I were in your
shoes. If funding is easy, let it be easy and do what you have to do when the
climate changes. Adapt

------
rthprog
Good for you Dan.

I'm curious - is 'Airtime for Email' keeping it's name now that Sean Parker &
Shawn Fanning started 'Airtime'?

~~~
dshipper
Thanks! Yes we are.

------
tferris
I like your ambitions and the ability to write popular posts on HN. But I do
not buy into this post, it's obvious that there's is something which bothers
you:

You together with your friends were rejected by YC in the past, now your
friends got into YC _—without you._

So, what does it mean? Was it because of you? Are your friends more
entrepreneurial than you and are they just smarter? Graham says the team is
always more important than the idea and that he rather takes great teams with
mediocre ideas than the other way round—so it must be you, you do not fit into
YC?! Or was it just by accident? Nobody knows but this awkward feeling will
stay with you for some time.

Getting into YC is for many younger entrepreneurs and starters a great
opportunity and finally an approval for their skills. Saying "I decided not to
go" to the interview and then after your friends gotten into YC saying "but
again, I said no" and writing just a long blog post is just—sorry no
offense—the desperate try to keep your state and save your face. It's like
those guys in a bar seeing a hot babe too shy to approach her saying "no, she
not my type" or "c'mon guys, is this your league? She is ugly!".

Bringing up the job offer from Friedman (which was more kind of a PR stunt of
42floor) is another weak try to prove that you go your own way forgetting that
this job offer was ok but not a real opportunity like YC.

Not that YC is everything and that you won't have other opportunities but we
all know that YC could have been a great opportunity learning new stuff for
you and why miss it? This was a heavy bummer which you haven't worked up yet.
You don't need to tell the world about it or that it hurts you but don't tell
us that you are fine that you missed the hot babe while your friends are
dating her already for months.

~~~
caw
This post got downvoted, but there are some interesting points.

I also read the part about "my friends got in without me" and was like "Oh
snap, that's awkward." Reading a post on the Internet, you don't know what
happened in the mean time. Maybe they worked really hard. Maybe Dan really was
dragging them down, and the team seemed more solid without him. Maybe it was
just luck (the rest of the applicant pool was weaker 2nd time around). There's
some introspection Dan could have here. What was different? What was missing,
and do I need to work on that piece?

But they still wanted Dan to join. Those are some pretty good friends.

>"We all know that YC could have been a great opportunity learning new stuff"

Who cares? I also don't believe that YC is the end-all-be-all. If you accept
something "just for the opportunity", then you'll be perpetually running
around looking for that. For one, college is an opportunity his friends are
passing up (for now).

It reminds me of a situation a friend of mine was in. He was applying to
Techstars for his startup, and then he got an internship at Facebook. He
accepted, but he was trying to decide whether he should quit the internship if
he got into Techstars. A professor of ours suggested that he had greater
opportunities at Facebook than Techstars, because he'd meet hundreds of people
in the mobile space, and that was worth more than what Techstars was going to
provide him for his mobile advertising system. If he left for the "great
opportunity," then he would have left Facebook. By the way, that's where he
joined after graduation. That was quite the opportunity that he would have
passed up.

I agree with Dan that we always need to periodically stop and evaluate what
we're doing and why. Sometimes things are done a particular way because
"that's the way it is." If there's newer and better ways of doing something,
do that. If there's another path that will get you to the same endpoint (a
flourishing business), is the route going to matter that much? The vision will
keep you going in the right direction, and so long as that doesn't change, it
doesn't matter what obstacles are thrown in your way.

