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Thanks HN: Goodbye, Golden Handcuffs

347 points by jriley ↗ HN
I'm a YC '08 Reject underwhelmed by my safe, boring corporate gig. Regular scans of HN remind me of the excellent things happening elsewhere. I was particularly struck by the theory that the best example you can set for your kids (0 so far) is to pursue your dreams, not an income.

I quit today, bought the supportive girlfriend a ring, and will start January 2011 as my own boss. I'm giving myself six months to bootstrap. Thought you should be the first to know.

Let the fun begin.

120 comments

[ 4.3 ms ] story [ 154 ms ] thread
arianb
It'll be a tough and long road, but if you're really set on it, you'll be happier than ever. Good luck, man.
kaffeinecoma
What are you planning to work on?
jriley
The original project exists in working order and my partners agreed to let me buy their share. I'll be building out v2 as we designed. We all took 2 weeks off in 2007 to build it, launched it, and hardly ever touched it again. v2 carries it to iPhone, iPad and starts marketing it.

If I have ambition after that I've got a few quick ideas (a short e-book on an area I've developed expertise, an obscure niche how-to site, fixing up my rental property, etc).

tapiwa
Well, good luck.

Do not necessarily do one project at a time though. Keep a list of things you want to work on. Whenever you find yourself needing to take a break from the main project, chip away at one of the secondary projects.

You might be surprised to find the idea you deem least important actually giving you the biggest payoff.

doublez
+1
Semiapies
You took a few downvotes from a faux pas; don't worry about it, but keep in mind that here, we just upvote the original post for a direct "+1".
jey
Relevant: http://www.youtube.com/watch?v=jwG_qR6XmDQ

Rumor is that the "boss" was actually David E. Shaw himself.

hasenj
I already regret not learning serious hacking in high school and university.

I got lots of A's (and B's), mind you, and I did work on projects of my own and everything, but I really saw it as just a hobby. I was always on windows, mostly dependent an IDEs, and I always thought I gotta be doing something more serious, like gasp oil and gas.

Good thing I'm still 25.

But I really feel like I should've started thinking about doing a startup when I was 18 or 20.

gregpilling
I am 41 with a product to be launched soon. It is never too late.
earle
It's not a rumor, Jeff Bezos did indeed work at D.E. Shaw & Co. So did quite a few well known people in technology.
[deleted]
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skbach
6 mos ain't enough, but otherwise, great idea.
sachitgupta
How much do you think is enough?
nostrademons
3 years.

http://friendfeed.com/paul/0268007b/how-long-does-it-take-to...

eru
You can start making money with less than a good product. And needing no customer feedback, because you have long runway, may actually not be the best external stimulus to choose.

(Take this opinion with a grain of salt, I haven't done my own startup, yet.)

joshuaxls
Unless you're Groupon or any number of other startups. It helps to start out with a business model.
nostrademons
Andrew Mason first had the idea for Groupon in September 2006, which was more than 2 years before Groupon officially "started" in November 2008, and probably at least 3 years before they achieved mainstream success.

http://www.chicagomag.com/Chicago-Magazine/August-2010/On-Gr...

chc
My mom first had the idea for rollerblades in 1968 — that doesn't mean she's a cofounder of Nordica. Thinking of an idea for a business is so many light years away from actually acting on that idea.
nostrademons
It sounds like Mason was actively working on The Point/Groupon for those two years, not just passively thinking about it. He quit his day job in 2006, he was enrolled as a student during the time period, he launched The Point about a year afterwards, he was in full contact with Lefkofsky during the time, and he launched Groupon a little less than a year after the decision to refocus The Point on something that could actually make money.

That's very different from dreaming up an idea and then forgetting about it for 30 years while you work on your day job.

stevenj
I think Andrew started out by creating The Point in 2006 which was focused on collective action, rather than collective buying.

It was focused more on supporting/eliciting action regarding "causes" than selling local services at a significant discount to msrp.

nostrademons
That's the sort of iteration that basically every business needs to go through, though. The great-grandparent post points out Groupon as an example of a business that succeeded in much less than 2-3 years because it started with a business model, and I pointed out that Groupon neither had a business model when it started nor took only six months. This whole subthread started with a question about whether 6 months is adequate for someone just now quitting their day job - it's most likely that someone in that situation is at that "I'm thinking of a web platform for collective action" stage, not at the "I have a web platform for collective buying" stage.
lrm242
6 months isn't enough for what? To build a product and start selling it? To raise venture money? To put together a presentation and pitch 10 customers?

6 months is plenty of time to accomplish a lot. It's enough time to build a product and get non-trivial revenue. It's certainly enough time to prove to himself that he made the right decision.

cmer
I completely agree with this. 6 months is definitely not enough runway to iterate a few times and find a winning combination. I've seen too many people fail because of the lack of runway.

I suggest that you do a few consulting gigs on the side to keep you afloat...

Congrats on your big move!

noelchurchill
Your account is less than an hour old. Did you create a new one since applying to YC in 08?
jriley
Yes, just created this account. I never posted on the old account, just read.
dorkitude
Congrats :)

If you're in SF, let me know

We have a sweet co-working space for hackers with all of the three C's: coffee, camaraderie, and a fast connection

jriley
Appreciate it. I'm actually in Austin though, and eager to meet some like-minded folks. I'll be checking out the local bootstrap chapter to start.
lrm242
Love to meet Austin entrepreneurs. Send me a note and let's get coffee: LinkedIn is in my profile or marascio at gmail.
codypo
I can vouch for getting together with Louis. He and I have done coffee a couple of times now, and he's got a great perspective on everything from funding to really in-depth technical issues.
malbiniak
Congratulations, good luck, and reach out often and always if you need a nudge or support. Full disclosure: I've been in the same boat and have been threatening to jump. If you're open to it, I'd love to exchange a few emails.

ps, wasn't there a new incubator recently announced in Austin?

codypo
I can speak from experience when I say that Austin's entrepreneurial community is welcoming, supportive, and full of very sharp folks. You should definitely check out the Lean Startup group (http://www.meetup.com/Austin-Lean-Startup-Circle/). Our next meetup is a joint holiday mixer with a lot of other Austin groups (like Austin on Rails), and it promises to be a great way to meet a ton of folks.

Also, I'm not sure if you're looking for a workspace with a lot of people in the same position, but we've really benefited from participation in the Austin Technology Incubator.

Edit: why do I say folks so much?

jacoblyles
How big is the Austin startup community? Austin seems like a hell of a lot nicer place to live than the Bay Area, but I'm afraid I'd miss the incredible magnitude of the support available to startups here.
edash
I'm in Austin, have a company that's tiny but growing and have a few friends doing startups. I'd love to help any way I can.

Email me! It's in my profile...

dannyr
In the Bay Area here.

Where/what is your coworking space in SF?

PStamatiou
Another SF-based startup here - I would love to know as well. We usually work out of my apartment (don't tell my landlord!) but getting a change of scenery from time to time would be nice.
[dead] joshstrike
Yeah, but what they don't mention on Ycomb. is that this is all, 100% hype, and none of these ideas has a profit model. The rent around here is paid out by trust funds and the last dregs of the second web VC hysteria.

There are only two guaranteed ways to make money with an internet startup: Porn, and gambling. Ironically, the only two things YC won't invest in. So wholesome, they are.

staunch
> Thought you should be the first to know.

Good and good luck. Now please tell your fiancée!

suhail
jriley: Email me suhail@mixpanel.com -- You just got free Mixpanel, good luck when you launch we're here to help.
DanielN
This is some of the best and most simplistic advertising and pr I've seen in a while. I've heard of mix panel probably 50 times but this was the first time I clicked through your website to see what you guys are all about.

Nice product by the way.

patio11
Congratulations on making the most important decision of your life and, secondarily, on opening the business. Words cannot express how much better self-employment is than what I used to do for a living.
stavros
Well, it's only good if it's making you money...
thenbrent
It's only sustainable if it's making you money. It's always good, even when it's bad.
StavrosK
It depends on your definition of good, then... It's certainly enjoyable, but if you lost years of your life and have nothing to show for it, I wouldn't consider it a tremendous success. That said, there's nothing I'd want to do more than having a startup.
thenbrent
if you lost years of your life and have nothing to show for it

If you have nothing to show for it, you haven't actually started a startup. You may not get a 7 figure bank balance to show for it, but you'll get something out it. Be it a website you can show off, better anecdotes for job interviews & parties or a network of new friends.

cicero
There are things that are far more valuable than money that a person can gain from an experience.
roc
> "if you lost years of your life and have nothing to show for it"

That's kinda how I feel about corporate gigs. You have stuff to show for it, but there comes a time when you realize most stuff doesn't really have lasting value.

And to those who suffer a bad gig to have money to do the things they really love: well, it's funny how little money most of those things really require.

daeken
I disagree. I spent 3.5 years doing the startup thing. I made effectively no money. Knowing what I know now, I'd do it again in a heartbeat, no questions asked. I learned more and grew up more in that time than in the rest of my life.
StavrosK
How did you afford food/rent if you made no money?
huffer
I second that! I'm amazed by the fact that half the time people seem to disregard completely this fundamental obstacle in doing a startup: you need to have at least the basics covered, like food and a roof above your head. You shouldn't live like a king but even the modest living costs.

Is it only people in US who think that? I don't think so, US is not particularly known for social security and such -- maybe this comes from people who either are already wealthy or they live with their parents :)

I have worked for 2 years plus to earn and set aside the money that will allow me 6-7 months of freedom to start something up (well, and then I screwed my hard-earned freedom, but that's another story); with this tempo you'd (I'd) need to slave away 8 years to earn 2 years of freedom, the amount I'd deem necessary to start up something serious and see money coming back to you.

So please, always mention how you have your basic needs covered and for how long before preaching bootstrapping to others :)

Kurtz79
If you work a couple of years in a "boring, corporate gig" and watch your spending carefully (i.e. rent a "decent enough" flat, buy a used and "working well enough" car, eating reasonably cheap), you should be able to save enough to support yourself for the same amount of time, in my experience (and I'm on a Spanish salary, considerably less than the equivalent in the US or nordic countries here in EU.)

Of course the whole time you must be prepared to sacrifice bits of your quality of life, before and during the bootstrapping period (hopefully not after).

I really depends on your goals in life.

nostrademons
I'm curious - what do you think is a "typical" salary for software developers, and what do you think are "typical" expenses for someone living in, say, Silicon Valley?
krschultz
You have to radically reduce your expenses if that is the case.

Are you tracking your monthly expenses? I assume rent is the highest, can you take in a room mate? Move into a smaller place? Sell your car and buy a beater?

I took 3 months off (not for a startup, I went skiing the whole time) for <$4,000. I can save that up in 3 months of working, but I drive a 10 year old car and rent a small apartment while most of the guys I work with are driving $30,000 cars and living in big places. But the car doesn't matter to me nearly as much as the freedom to take time off.

daeken
The first year of it was spent living with family, paying the bills via some light contract work. At that point, I wasn't really sure of where I wanted to go startup-wise, so I leaned on them for a bit.

From there, I moved to Atlanta and into the house of a business partner of mine. Initially, he was working fulltime at a day job while I worked on our product. This lasted for about a year and a half before he left that job.

The last year and a half were spent surviving off savings, stocks, about two months of contracting, etc. In the end, the runway ran out, and the house was foreclosed on (kinda happens when you don't pay the mortgage for a few months). We launched our product the day we moved out of there.

It was the most stressful time of my life, the most work I've ever done, and I feel like I aged a decade in that 3.5 years. But it was easily the most amazing time of my life.

I'm now living in Manhattan and working for an awesome company, but I still miss the startup life. I figure I'll end up doing it all over again in a few years, once I come across the right idea and strategy.

bradhe
>I'm now living in Manhattan and working for an awesome company, but I still miss the startup life.

When I was finishing college I could not WAIT to get outta there -- what between homework, regular work, and just being plain TIRED of school. The day after I got my degree, I said "man I already miss school!"

How did you feel right after you left your "startup life?"

daeken
I can't really say for sure, simply because there was no "ok, well, my company is dead" moment -- the company is still going, I'm just not really doing anything. I guess the closest thing was my first day at Matasano, and I was mostly just excited at that point. I miss doing the full-time startup thing, but not so much that I'd jump at the opportunity to do it again right now. I'm sure that I'll get the itch in ~3 years, though.
csomar
Family. You can live with your parents, actually nothing wrong about it in many countries. If you eat with them and they have Internet, your living costs are around 0.
gawker
Yep.. it's all about being filial in Asia.
jasonkester
Not necessarily. Neither of the sites that have done the most for my quality of life have ever brought in much in the way of direct income. They have, however, put me out there as a guy who's capable of building products like that, which have led to some really good consulting gigs, thus allowing me to keep traveling the world and doing my thing from a laptop.

So even though it was years before I hit on the first product that generated significant income on its own, there was still a net benefit from having put out my shingle right from the start.

rick_2047
They have, however, put me out there as a guy who's capable of building products like that, which have led to some really good consulting gigs, thus allowing me to keep traveling the world and doing my thing from a laptop.

So indirectly it's only good if it's making you money...

:)

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jeromec
Let the [work] begin.

FTFY I hope you're prepared to work at least five times harder than you did at your safe job, and for little to no guaranteed reward. Actually, if you're only giving yourself six months, make that ten times harder. I would say good luck, but considering around 90% of startups fail, work hard, be persistent and expect difficulty, seems more helpful to say. The success stories appearing on HN can give a skewed impression on how hard it is to succeed. Congratulations, though, for bucking a potential path of regrets.

Edit: A bit more advice is release early, and often. The trick is finding the balance between minimum viability and having enough value for traction. Iterating on an idea is almost always necessary, so be on the lookout for how that can help and possibly even save your endeavor. A six month deadline to succeed means you're really going to be up against it.

rewind
The comments and/or advice you're giving (and the tone you're using) are the type of things you say to someone before they decide to make the jump if you want them to think long and hard before making a tough decision. When you say it like this to someone who is announcing that his decision is made, you just sound condescending. It doesn't help that you throw in a bunch of advice when you don't even know who he is, what his company/product is about, or what his plan is.
jeromec
I don't mean to sound condescending. I can't help the timing of the decision, either. I'm also guessing he's read HN enough to have more than my comments to weigh for various perceptions of a startup. To my knowledge the failure rate of startups is around 90% (not my doing). In light of that, I felt the best thing I could do if I wanted to truly help, which I do, is try and foster a tough, ready for battle mental mindset. His announcement seemed a bit cheery and optimistic, and I wanted to suggest that, realistically, the road to startup success is not usually a cakewalk. HN is largely a startup community, so I figured others might find value in my comments as well, and if such comments harm his enthusiasm, and are more destructive than constructive then, IMO, he's quite likely to end up in the 90%.
c2
There's nothing wrong with a bit of honesty.

You need to be mentality prepared for the difficulties inherent in starting a business all by yourself. It is a different set of challenges then corporate life and the more you understand that ahead of time the better off you'll be.

I appreciate advice like that over a superfluous "good luck", "you made the right choice"< etc.

toast76
Wow. The Thanksgiving parade was last week Mr. Raincloud.

Here's some positive thoughts for you!

- Running your own business is quite simply the most rewarding thing you can ever do (professionally at least). - Succeed or fail, you'll come out of it better off than you started. - Don't measure your success by whether TechCrunch writes about you. Measure it by being proud of what you achieve. - Even your biggest failures are at worst just one learning step to your first success. - If nobody has heard of you in 10 years time, but you're happy, enjoying your work, have a happy and healthy family and you're still your own boss...then you've succeeded. Congratulations.

Most importantly - Ignore "minimum viability", "traction", "iteration", "deadline" and all the other things a dozen different "5 steps to success" books might tell you.... if you have the confidence to go it alone, then do what works for you, YOUR product and YOUR dream.

roel_v
"Succeed or fail, you'll come out of it better off than you started."

About half of the comments I read so far have said something to this effect so far, there's only so much a man can take before he needs to speak up ;) : this is bullshit. I know many (as in, 10+) people who started a company and got utterly fucked for the next decade, maybe two, because of its failure; and all they have to show for it is a period on their CV that they have to make excuses for at any interview they go to.

Sometimes, failing can bring you valuable experiences that you can apply afterward, and only if you go into a specific direction as an employee after your business has failed. This hippy bullshit 'all is great, even if your wife leaves you, you're 100k in debt and you've spend the best decade of your life not even in an office but in a spare bedroom hunched over a desk made of an old door' needs to go and be replaced with realism: spending 5 to 10 years in abject poverty, rebuilding a life at an age where most of your peers are living a happy life with their families sucks.

The potential upside is huge, and yes if you just manage to sustain your company you've been successful, but don't make it sound like it's going to be great no matter what the outcome, because it's not.

scorpioxy
Part of being an entrepreneur is knowing when to change directions or abandon an idea all together. Spending a decade on an idea that is not working and won't possibly work is not all that smart.

This type of life is definitely not for everybody.

The fact that you know people who have failed also doesn't mean anything. I know a lot of people who haven't even tried and that, to me, is a lot worse.

roel_v
Spending 10 years chasing one pipe dream after the next isn't smart, either. My point is that 'doing it' or 'not doing it' are not inherently smart, brave or whatever. "It Depends"(TM) on the circumstances. The sweeping generalizations about how great the entrepreneurial life is that are made here are unwarranted.

"The fact that you know people who have failed also doesn't mean anything."

Of course not, it's just anecdotal. But it does disprove the notion (your notion even, maybe) that no matter what happens, if you start your own business you're always going to be better off.

"I know a lot of people who haven't even tried and that, to me, is a lot worse."

Depends. If whatever they'd like to try (assuming they'd even like to) is not going to work, they're better off not doing it. Obviously there's no way to knowing up front if something is going to work or not. Still, being realistic about your prospects and deciding that objectively and realistically you're better off not trying, then that's a valid and honorable decision.

Sukotto 

  I know many (as in, 10+) people who started a company and 
  got utterly fucked for the next decade, maybe two, 
  because of its failure; and all they have to show for it 
  is a period on their CV that they have to make excuses 
  for at any interview they go to.
Why make excuses? Talking about that experience opens the door to discussing just how well suited you are for the job you're interviewing for.

Q: I see on your resume you spent ten years at example.com which does not seem to exist any more. Tell me about that.

A: Starting up example.com was an amazing experience. After ___ years at ______ company I decided that I really wanted to try starting and running my own company. [Overview of the main ideas and pivots of the various things he tried].

Unfortunately I learned that I just not strong at some critical business skills like ______ and _____ though I did hone my ______ and _____ skillset [where these two are relevant to the job you're interviewing for].

yesno
Could backfire you. There's no guarantee that this is a home-run to get a job. Keep that in mind that the world is not "ideal".
pbhjpbhj
At least they know you're not likely to leave to start your own business ...
toast76
The point of my comment was not to say, "hey everything's going to be great! Throw your money away, you CAN'T lose"

The point was to counter the negativity of the GP with some positive thoughts.

Being positive doesn't mean to ignore risks, or to turn a blind eye to consequences, it means starting off with the belief that you can succeed.

hasenj
> I know many (as in, 10+) people who started a company and got utterly fucked for the next decade, maybe two, because of its failure

Really? That's odd.

Sounds like they didn't know what they were doing.

Did they by any chance spend a lot of money in a field they didn't know anything about and just hoped somehow it will magically work?

Yea, if you're non-technical and you think you can build a product by hiring 10 developers and 4 product managers at 100k/year each, of course you will get utterly fucked.

roel_v
Maybe I should've been more explicit since on here it's reasonable to think of 'tech startup' when one mentions 'business', but I meant in all sorts of businesses - actually the tech scene is very small here, and even then it's mostly IT services or web development (i.e., mo product development); I don't know anyone who had a failed business in that field and was seriously affected by it.

When you start for example a plumbing company or whatever and you buy 25k worth of tools and a lease contract on a van, and it fails and you need to take a job afterwards, on a employee plumber's salary that 25k is huge, enough to make your and your families life miserable.

I agree that for tech companies, the situation is usually not as precarious - if you have the skills to start a company like this, or even if you don't but almost do, you can get a fairly well-paying job and not be as affected. In those cases you would presumably get proper legal and accounting advise and shield personal money from the business liabilities but many businesses start as sole proprietorships and are very vulnerable to even small setbacks.

jasonkester
This is what everybody says, but I just haven't found it to be true.

I work 40 hour weeks sometimes, 20 hour weeks other times, and often go entire months not doing much at all on the startup. The ball is always moving forward though, and things are always getting better.

It really doesn't take a huge amount of effort to get your first version out the door. And it doesn't take much effort beyond that to get to the point where money is coming in. Once that happens, there's no particular reason I can think of to work 60 hour weeks, unless that is something you want to do.

Naturally, it depends on what you're building. If you're a single founder though, it pays to build something straightforward that solves problems for people with money. There's lots of things like that that need building. Build one and you'll (hopefully) find it doesn't monopolize your life.

jeromec
I certainly agree that's possible, but not everyone finds the road rosy. See here: http://news.ycombinator.com/item?id=1961429. Better to overestimate the difficulty and be pleasantly surprised than vice versa IMO (especially in the context of a 6 month deadline).
sreitshamer
You might need a lot more than 6 months. But, like my wife always tells me, you don't fail as an entrepreneur until you quit. And the ride is sure worth it. Life is short.
kadavy
Amen on that. I figured I'd need 6 months starting about 3 years ago. Things are really starting to come together now though.
pbhjpbhj
>you don't fail as an entrepreneur until you quit.

I'm not experienced in it, but I imagine that one can fail as an entrepreneur because you didn't quit.

Flogging dead horses and all.

rrrhys
Best of luck, very envious over here!

Do you have a blog?

jriley
Thanks, no blog yet. Plan to start and post as I learn (Austin places to work/meet, local grants and SBA loans, best library for tech books, etc).
middlegeek
Good deal, I am happy for you! Get some stuff done.
toast76
If I have two pieces of advice I can share,

1. Pick up some contract work - you can easily turn 6 mths into 12 mths, and then 2 years, then 3...no matter how many projects fail to get off the ground, if you have a bit of side income, it'll help in the long run.

2. Don't ever forget why you quit - if that is to "pursue your dreams, not an income". Write it on a wall above your monitors and don't ever forget it.

EDIT: Oh, and good luck! :)

gommm
Be careful with contract work though, it's very easy to fall into the trap of taking on too much and pushing back your own project...

Contract work can be worse golden handcuffs than a job in corporate

jacquesm
It beats personal bankruptcy hands down though.
nerd_in_rage
how much cash do you have in savings? i'm thinking of doing the same thing.
jriley
Living Fat = 3 months, Living Lean = 12+ months. I'll use my 401k but not Roth IRA. Also have some equity/cashflow from a duplex that helps. FWIW, I woke up this morning feeling great on 4 hrs sleep and not worried about money at all - the prior six months mornings were filled with worry and dread.
volandovengo
Good for you man, I did the same about a month ago. Amazing how hard I found getting rid of the golden handcuffs.
checoivan
Glad to hear this kind of stuff. Your words encourage me to do the exact same thing.
gshannon
This is the best thing you will ever do.

You will look back at this moment and realize it is the defining moment in your life.

kj12345
Good luck! One odd piece of advice I have is to recommend limiting the amount of startup advice you read online. It's too generic now that you've committed. Focus on what you're creating, not on making your venture look like the internet's current concept of "startup". Look, for example, at the popular phrase "Minimum Viable Product". You'll find a lot of excitement around the "minimum" part, but the "viable" part matters also and is fully dependent on what you're doing. There are many things that are unique about individual businesses, but generic online advice by necessity exaggerates the shared aspects.