Why I'm Doing It All Wrong

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.

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.

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.

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.

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...

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.

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.

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?

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".

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.

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.

"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.

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.

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.

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.

>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.

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

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.