Success in startups takes time. It's a long, long road.

My first startup was Student Lofts in 1998, a loft-building company for college dorms rooms.  I started it on my 3rd day of freshman orientation.  It was the first time I ever created something of my own.  My second startup was DC Discounts, a local discount card company that I started while I was working on Capital Hill.  I started it 3 weeks into my internship when I had grown bored of answering mail.  My third startup was Openvote, an online platform for polling your community.  It was the first time I ever did anything on the web.  My fourth start-up was FlightCaster.  It was the first time I ever found success.  It's been a long road.

1998 - 2002: Student Lofts made good money for a college student.  But on my per hour basis, it was below minimum wage.

2000 - 2001: DC Discounts failed before launch.

2006-  2008: Openvote failed without making any revenue.  It took my investors' money and everything I had, plus credit card debt.

2009 - 2011: FlightCaster sold.

I've been doing startups for over a decade now.  I have skipped summer vacations.  Passed on interesting internships.  Missed on-campus recruiting.  Worked through every Thanksgiving.  I was near-broke for most of my 20's.  I have failed dozens of times.  I've been depressed.  I've been lonely.  In case you were wondering, startups are really, really hard.

Do I regret any of it at all?  Not a chance.  I've sat in BigCo cubicles for very short periods of time.  I know with absolute certainty that it's not the life for me.  I've chosen the life of an entrepreneur because, well, there's nothing else I would rather be doing.  I love creating things from scratch.  I love innovating.  I love motivating people to go beyond what they think is possible.  I love fixing problems.  I love the thrill of closing deals.  I love the rush of being responsible for so many different moving parts.  I love interacting with fantastic people.  I love feeling proud of what I'm doing.  I love being able to go rock climbing at 3pm.  I love biking to work.  Startups are hard, but there are certainly benefits.

It took 4 companies and 10 years of education to get it right just once.  I've read 1000s of blog posts and dozens of books.  I've asked 100s of people for advice.  It's been a long, long road. 


I just chatted with an MBA student that came to me for advice.  He was planning on spending his 2nd year of business school working on his startup.  

I asked him: What then?  

He responded: If it takes off, I'll turn down McKinsey and do it full-time.


Sorry dude, it doesn't work that way.

I could be wrong.  Maybe your startup is going to hit the market just right and take off.  You'll be so busy trying to scale, you'll barely have time to deposit checks from investors...

But, I'm probably not wrong.  If you work really hard, you'll get a product launched and hopefully build up some buzz.  Maybe there will be some traction.  But when that decision to McKinsey is due, there is a 99.9% likelihood that you won't have enough traction yet. But if you keep at it, work your ass off, stay determined, iterate like crazy...well, then you might just make it big.

But that's not going to ever happen, is it?

You already know you're going to take that McKinsey offer.  You're Eduardo Saverin from Facebook's infamous history, who did a summer internship at Lehman Brothers while Facebook was skyrocketing with growth.

And that's okay, if that's your decision.  I don't have grudge against the jobs that 99% of people do.  Entrepreneurship is not for everyone.  If you decide to take a job that makes sense for your career and helps you support your family, I support that decision 100%.  But when you ask for advice about your 'startup,' my response is never going to be about your product.  I care far more about you and the potential implications of you romanticizing what it means 'to do a startup.'  My advice:

Don't waste too much of your own money.  

Don't waste anyone else's money.  

Don't drag any co-founders or employees along with you.  

Do it as an educational hobby, but don't call it a startup.

If you're on the fence about entrepreneurship, just don't do it.  This is a big plunge.  If you're not ready to jump both feet first, than you're just not ready.  If you want to be an entrepreneur, a real entrepreneur, you should know up front what you're going to do with that BigCo offer letter.  Skip the whole romanticizing entrepreneurship part. There will be lots of failure.  Lots of opportunities for giving up.  Real entrepreneurs, for whatever reason, keep going at it.  And they know that from the start.  If you're signing up for that long road, give me a call.  I'll help you in any way that I can.



Find discussion of this post on Hacker News 

I'm Jason Freedman.  I co-founded FlightCaster.  
You should follow me on Twitter: @JasonFreedman.
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14 responses
Awesome post - it's exactly why I've been plugging away since 2004. Thanks, I needed to read something like this right about now!
Great post Jason. I clearly remember you doing Student Lofts in our dorm room at Duke. We've come a long ways!
First of all, congratulations.

I am pretty sure Chris Patton stole my idea for a comment. It is an excellent post and I also needed to read something like this right about.. now.

I love your style of writing, please keep it up!

What a wonderful and refreshing post. A friend and I had just recently been lamenting the attitude of the founders of some new startups. Especially in the tech industry you seem to get two types of people - (1) the sort that are so focused on their idea that they forget to eat/sleep and just build for building's sake, and (2) the sort that want to ride the tech wave. The second sort tend to fall flat not necessarily because they have a bad idea, but because the startup is a means to the end for them. Sure, and exit strategy can be important - but except in very rare circumstances the startups that make it big are the ones that were the brainchild of sightly obsessive-compulsive founders who gave up everything else.
This seems useful, but also disheartening.

The flip side of what you're saying is that if you have something to lose -- if you can't face telling people "uh... I'm still trying to make this impossible thing work, and no, I don't know if it will, and yes, I've thrown away my career for this dreck that I'm not even trained for, just because it captured my imagination and I like to code" -- then you shouldn't be doing it. Because you will have a period when you look like a loser.

Aw, fuck.

Amazing post. Thanks for that man! Definitely is a ton of work and I feel crazy sometimes for pouring everything I've got into my business. At the end of the day, though, it's hugely rewarding and I would much rather be building a brand, my brand, than taking the "safe" road.

As a entreprenuer in software development, who routinely builds others dreams, I hear about a lot about people with a sometimes good idea wanting to get on the rich startup gravy train. Often with no marketing plan, or no understanding of business.

It occured to me, thanks to popular media, Startups have the same romanticism that people view the lottery, without the stigma of normal small business like opening a coffee shop.

The .001% that make it big covering up for the 9% that are doing okay and the 70- 90% that never make it (and sometimes fail spectacularly).

Entrenurialism doesn't buffer you from the raw reality, business is a competitive sport, people don't play fair, things don't always...and sometimes almost never go your way, but somehow that makes when things go right so much more meaningful.

In my "tour of duty" I have had seriously almost everything imaginable happen I never saw working for others. Servers failing at perfect times. Partners failing at "perfect time" Armed bandits, floods nearly carrying away office buildings etc. LIke hitting 20 stoplights in a row, 3 days in a row, sometimes I question if the universe is telling me to quit, or just testing my resolve, it seems like I'm at a level 10..and then I'm forced to dig in an go to 11 etc.

What keeps me going is having been in many normal companies, I know exactly where you can go, and it's usually pretty limited. The risk is much higher in the outside, but so are the rewards.

They say the first million is the hardest, and It only takes one to change everything.

thanks for the post .. can easily relate ...
Interesting that you mentioned getting depressed. That does happen - the highs are great but the lows suck.

Nice post, Jason. Thank you.

Wow, I've lived most of what you've mentioned in this post. I even started a damn coupon website/discount card service, and made some cash, but probably a pretty low per hour average.

I love having my own business and projects, but after a while, I do find myself just wanting to take that nice safe job... then I eventually wake up and go back to doing my own thing all over again!

Great clip and well timed for me? I've been at a startup for over 15 months now with a couple of flashes of success but mostly frustrating indifference to our service. I keep asking myself "where is the line between believing/ hard work and stupidity?". A more tangible question- what is the time frame of if my product/ service has nottakn off yet will it ever take off? I believe in us and it's a great group of people but something is not adding up....
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