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Startups Are Hard (jazzychad.net)
410 points by tlb 2151 days ago | hide | past | web | 111 comments | favorite

There's a meme to be spawned about things that work like the parole narrative in The Shawshank Redemption, where good things only happen when you decide to stop giving a shit about them. Deal closing of all sorts definitely fits it.

In the meantime, perhaps console yourself this way: you haven't found the pitch that's opening investor wallets yet, and maybe that's a good thing. Maybe the pitch you're using isn't your best bet; maybe a "yes" at meeting 38 would have put you on a bad path.

My friends and I got a high-seven-figures "yes" in '99 that ultimately killed our company.

Meanwhile, Matasano went through exactly what you did in 2005; every company that found a "yes" got dead as a result. We're relieved to have dodged the funding trap.

Best of luck to you. You don't need gatekeeping investors to succeed.

Time and time again, anecdotes like this make me want to avoid investors entirely.

While the entire post is both cathartic and poignant, one line stood out for me because of its brutal honesty.

Am I jealous of other companies' success? I would be lying if I said no.

Thank you for saying this. I've always wanted to, but feared I'd be called out for it. In public. In fact, I think it's part of what keeps the fire burning inside - that constant hunger to try and figure out why some folks are plain better / more successful at the game, and then trying and internalizing / applying those lessons.

And it can get frustrating when you can't replicate / emulate what others have achieved seemingly easily. As a corollary, this is probably why Jack Dorsey and Dennis Crowley are enigmas unto themselves.

An important aside: Chad, I'm someone who has tracked (and may I add envied) the Notifo story. And I admire the work you've done, from fanout.js, to snagging Paul for a co-founder, to HN for Android, to PicAFight, to GramFrame, to Vorepad........I've found myself in awe of how prolific you've been (and you don't even know me).

It's possible you've been doing one thing too many (because you love APIs and can't keep from tinkering with them). What I'm convinced of, is that you have the talent, the work ethic and an incredible co-founder. All the best, I'm hoping I have to transition back into pure envy real soon.

Thank you for this.

I was doing all that "one thing too many" stuff during the "crap, what are we gonna do now" phase where we weren't super productive and just played around with prototyping some ideas.

Not shipping anything made me feel terrible, so we spent some time making random side-projects to stay sharp. All of them were good learning exercises, too. I made sure that each project had some part of it that I didn't know how to do, so it would force me to learn new things.

There's no doubt you've sharpened your saw with the projects you've worked on. It could've been way worse - I've been through the blues / in the doldrums, and couldn't get myself to do anything for weeks on end.

I happened to navigate to Paul's article on fundraising, and further, to Alexis' one on keeping calm and carrying on (http://alexisohanian.com/keep-calm-carry-on-what-you-didnt-k...) and I was blown away. There's no way I could've survived something like that. You're in great company.

I'm looking forward to what you come up with. Here's to a great couple of years ahead.

I never understood why you didn't charge for Notifo? I would have paid something for it.

The #1 reason I ignored notifo is I couldn't understand the business model. As such, for our internal systems, we notify via SMS, email and jabber. Things that I know will still be around in a year.

Why the past tense? It's still going. As far as I know, they plan to charge for over 10k notifications/mo when they get a bit more traction. I use it on my Android phone and it's fantastic.

I left my job to work on my startup full-time, and agree with all of this. It's one of the hardest things I've done. I had to detach myself from material possessions and live frugally. I don't have much of a social life anymore because it's expensive. I've had to force myself to work when I didn't feel like it days at a time. Programming was no longer fun.

If you're not ready to sacrifice everything you have, possibly including your health, then work on your project on the side. You really do have to be crazy to be an entrepreneur.

The positives: It's thickened my skin, I manage my finances better, I appreciate things more, I treat people better.

Thanks for sharing that. We've had a lot of articles lately that treat startups like 9-5 jobs so I think it's important that people like you give some perspective on how it's really like for the waste majority of startups.

This reminds me why passion is so crucial when starting your own business. You will work crazy under conditions that most employees would see as unreasonable and there is a great risk that the business will fail. But as long as your doing it out of passion you can motivate yourself through the hard times and, if it doesn't work out, walk away with the satisfying feeling that you followed your dream and gave it all you got.

Would you say that your passion played an important part in managing your business?

Absolutely. I chose the entrepreneurship route because it's something I that I feel I was born to do. Of course, I try to maintain a healthy lifestyle and a positive demeanor on the outside despite sacrificing a lot. It will take a lot of adjustments if you decide to bootstrap a startup full-time.

Absolutely. I chose the entrepreneurship route because it's something I that I feel I was born to do. Of course, I try to maintain a healthy lifestyle and a positive demeanor on the outside despite sacrificing a lot. It will take a lot of adjustments if you decide to take the plunge full-time.

I can relate to programming not being fun anymore. After my startup was finally bankrupt I just couldn't get myself to sit in front of a computer anymore at all. I did a two week bartender crashcourse and did that for 3 months.

Nicely done. I especially liked "We let them [the investors] dictate our path with their negative signaling instead of listening to our guts."

This trap is something that is so easy to fall into and so painful to pull out of. My first startup had a 'star' VC fronting it, he loved the concept but didn't really understand that his vision was often in conflict with the founder's vision. That really hurt as the company was ripped too and fro trying to achieve a couple of really orthogonal goals.

Tom Lyon once told me that really it takes three startups before you 'get it'. One which is a somplete disaster, it helps you see what you did wrong and what can go wrong. One which isn't a complete disaster but exits sideways, which is to say you work at it day and night but when it exits you find yourself exactly where you were when you started. Then the third one where you know what to expect, you have a solid idea of what not to do and you keep laser focused on getting in, getting done, and getting it shipped.

It is very hard though, always.

Anyone thinking about moving to SF to launch a startup needs to read the Sacrifies and Startup Depression section 10x, assume it will be worse for you, and then decide.

And doubly so if you're married. If your spouse isn't on board and you've minimized the challenge, you're screwed.

If you're looking for a great place to live, Silicon Valley or San Francisco aren't it: even elsewhere in Bay Area (e.g., Sonoma County, bedroom communities in the East Bay) is far more hospitable. I was very pleasantly surprised when visiting Chicago, Seattle, Berlin, Brussels: these are world class cities where transportation is a breeze, average food quality is amazing (although, San Francisco still wins out on the "high"-end dining options). This was quite a shock from growing up in Former USSR and then moving to California (where San Francisco and Los Angeles were my example of "cities").

However, there's good reason I am here in Silicon Valley. Athens at the time of Pericles and Socrates wasn't a great place to live either, far worse than Silicon Valley. Same goes late Republican and early imperial Rome, Tang dynasty Xi'an, Florence and Venice during the Renaissance, Victorian London, etc... On the other hand, people willingly sacrificed their standard of living and prestige to live in these cities and and pursue activities they found meaningful. Being a big fish in a small, provincial ponds sucks: if you want to grow intellectually or professionally, you should be around smart and ambitious people.

To be fair, there are pockets of talent elsewhere (New York, Seattle) but they're generally rather insular: a lot of the places tend to be a combination of a revolving door for some (people joining and leaving in 18 months, very frequently moving to Silicon Valley) and a life long commitment for others (lifetime "softies" at Microsoft). While exceptional talent does exist in many place outside of Silicon Valley, the stories of people joining a company, staying long enough to make a significant impact and then applying their lessons elsewhere (e.g., the "Fairchildren", "Paypal Mafia", Xooglers) are not as common in less-fluid engineering job markets.

Back when I was a physics major in college, I remember musing that there were two time/place combinations in history that I really really wish I could've been a part of. Copenhagen in the 1920s, and MIT in the 1970s. Both of them were collections of incredibly intelligent people that were feeding off each other's energy and making some really awesome discoveries.

I think that Silicon Valley in the late 2000s and early 2010s is that place. Particularly centered around the offices of Google, FaceBook, Twitter, and YCombinator. There's an energy here, a thrill of discovery, that's just missing in most other places in the world. It's enough to make me overlook that the city is basically suburban sprawl, public transportation sucks a lot more than Boston/NYC/DC, the quality of life is honestly not that high, there's little sense of history (only of history being made), and everybody wants to get rich quickly.

I don't think I'd want to settle in Silicon Valley. But when my grandkids ask questions about the birth of the Internet age, I want to say I was there.

We cannot afford to drop everthing and move to SF. And considering where we are (Richmond in Virginia) and our roots here, we feel like we owe this town. There are a lot of things we are surely missing out by not moving to the Valley, which is the startup ecosystem, the investors, the talent etc. But startups also have to deal with the noise, the saturation, and the "meh" when you launch. Where as in Richmond, we can possibly have a far bigger impact, with a lot more people who will love us, and we are right next to DC.

I am sure we will not know if we made the right choice, for a long time. But I dont buy in to the belief that unless you are in the Valley, no one will give a damn (as touted by Vivek Wadhwa a few weeks ago).

Any thoughts?

EDIT: Needed to add a couple more thoughts that came out of the responses my post received.

a) Its really hard to find talent in SF - Right now, we are one non-tech founder and two hackers. And finding android or iOS talent in Richmond is like looking for needles. But I believe that if you find a darn good hacker, then a new tool or language is just a speedbump. We are still trying to find a very good UX designer though.

b) I agree with the Valley vibe. But it sounds more of a Goldrush than anything else. And I also agree with the vibrant support system that the Valley can provide. Right now, I get that through HN, blogs and my peers over email and phone.

I'll be moving from Minneapolis to SF soon. Before spending significant time in the Bay Area, I thought that the noise/saturation/and "meh" were a problem, but my experience was different. It's a very supportive environment, with a lot of smart people willing to help out.

There are three problems to the Bay Area:

1. Massive competition for engineering talent. It's probably harder to hire 20 brilliant engineers in SF than in any other major city in North America.

2. Cost. Our burn is increasing by 20%-30% because we're moving.

3. Echo chamber. Ideas tend to get reinforced here. This is often good or neutral; SV will sometimes recognize the significance of something before the rest of the country will. (There are a lot of people who still think Facebook and Twitter are hype and will go bankrupt soon.) But I imagine that there are ideas that make sense in SV that are ultimately bad ideas. And there are ideas that wouldn't resonate in SV that are probably huge opportunities.

This is a little off-topic from the original article, which is fantastic. But circling back: startups are hard, and moving to SV isn't a panacea. It may help a little, but do it with eyes open - because you want to commit to the startup life, and SV is a good place to do that.

All the three problem areas you identified are reasons why I would not move to SF until we are ready. If I see that the idea has traction, and revenue, and I didnt care about finding investors and talent, then I would think of moving to SF. Today, what we have built and is currently building, is still a pet project. We are keenly watching where it goes from here, but simply cannot move mid-sentence to the other coast.

Good luck though. You are much better positioned due to the YC framework and which should open doors far more easily than to a couple of outliers like us.

You're too close to the forest to see the trees. Forget you are a hacker for a minute and think of yourself as say a screenplay writer. Where would you rather be, LA or some hicksville town ? If you are in LA and you bump into some two-bit actress moonlighting in a bar and talk about your script, soon, she'll connect you to someone who knows someone else who knows something who will soon reshape your unsellable script into something that can actually get made and within a span of a few weeks you'll be on a studio lot while they go over the makeup of a costar you only saw on TV until yesterday! Sounds like complete baloney, but that's how it really works!! You can read say William Goldman's book Adventures in Screen Trade where he spells it out in considerable detail - Why professors with PhD in literature are still working on the nth draft of their dream project in the English Dept at Andover while some street smart dropout hacks away at a script on a couch in some dinghy motel on Hollywood Blvd that actually gets made.

It ain't fair but that's how it is.

In you go to SF with your pet project which has no traction and revenue, it will suddenly have traction and revenue. Don't ask me how. It isn't exactly logical. Things happen. You'll meet people who'll tell you if only you change this feature and add that feature and do this and not that you'll have a saleable proposition. So you'll say what the hell and give it a shot and soon it becomes so! Its just not rational, and as a coder and mathematician I hate irrationality just as much as you. But that's how it is. Whereas with no such brutal feedback, you can labor away at some precious project until it becomes larger than life and super-brittle and soon even you don't want to touch it cause who knows which module will break which other module, and then you go looking for customers and nobody really wants it cause its gotten way too complex for anybody to decipher.

I've heard ideas that are so lame ( an app that counts ONE TWO THREE while you do pushups. Really! Yeah, that's got funding to the tune of a couple mil! ) your 3 year old could have come up with it. So its not the traction, framework, revenue model etc. Its just finetuning an idea to the point where it becomes saleable. And for whatever reason, perhaps because its in their DNA, SV seems to have the sort of people who actually give you a listen and then tell you exactly how to go about it. They actually give a damn! If you have an idea, I think you should atleast spend 1-2 weeks in SV trying to pitch before writing it off as a futile exercise. Nothing to lose, everything to gain.

I agree that its better to be in LA than in some podunk town working on a script if you wanted a movie to be made. Because movie making has not exactly been democratized to the extent that software development and creating businesses has been.

However, if what I have is a piss poor idea that has not won over customers, has no traction or revenue, then I dont think thats a problem a million dollar can solve. It will just be someone else's money that I will end up losing over a terrible idea. I would rather fail with this idea where I am now, than work on it (with someone else's money) for the next year and then still fail.

The Valley entices everyone to go there. I both drank the koolaid in 99 and ran for cover in the wake of the dotcom crash. Entrepreneurs who persevered were the ones who coupled the right ideas with a sense of commitment bordering on the insane. Thats what I want to emulate. That, to me is more tangible than a million dollars.

You missed the parent's point. It's not the money of Silicon Valley that helps you, it's the constant brainstorming of ideas. You will be exposed to so much collective experience that your product will improve. On the surface, it will seem to be magic, since really it's the same idea you had when you lived in the middle of nowhere.

Except you benefit from talking to people with deep experience. When someone here tells you "have you tried putting this button on that page?", it's because they did it and it doubled your traffic. Experience of what works and what doesn't circulates so much faster in Silicon Valley.

Why would you want to be disconnected from the flow of ideas? If you think online forums are a substitute, they are, but with a time delay.

Completely agree. I am in the same boat as a Canadian not wanting to move to the states. While it may be true that many investors will rule you out based on location; my firm belief is that first time entrepreneurs should spend their time acquiring customers, not investors.

Customers generally don't mind if you're not in the valley (although it is true that if your product is built for tech oriented people the bay area may be a high customer saturation zone.)

It matters to customers who are themselves in the valley, like me. I know the teams behind most of the products and web services I use, and it matters that I know who to call when something doesn't work. If customers in the tech world are important to you, you should be where you can go meet them for coffee.

It's not just for investors. It's much harder to exit to a US acquirer if your tax/legal structure is that of another country. Due diligence is longer and more expensive and I have heard of cases where UK companies have been skipped due to potential issues of integrating founders re immigration and IP laws.

I just came back from SF yesterday, and would certainly recommend dropping everything and going there. Better yet, relocate to Palo Alto. Every other office on University Avenue is a startup and the ones that aren't are either VC firms or gathering haunts like coffeeshops & restaurants. There is a certain electricity in the air. You have to be there to feel it. It is definitely quite surreal, like out of a parallel universe. 20 year olds in jeans & tees & sandals lugging their laptops & iphones, talking animatedly about monads and dependency injection and mock functions, while 60 year old asset managers in black suits and polished shoes walk around in reverence. I remember thinking that I would have to be an absolute rank idiot if I can't get some bloke to fund me a half mil on a quick-flip consumer web play. On top of that, the guy who was escorting me, a 25 year old hotshot ceo of a stealth startup, pointed out various coffeehouses and said things like "i pitched here", " i raised 200k there" and so on and so forth until it was clear i was a dumb fuck wasting my time in the midwest.

So why am I back to the midwest ? Well, I'm not running a startup myself, atleast not yet :) And when it comes time to do so, I'll rush over there myself.

I guess this is what it was like in the 1960s in Greenwich village in NYC, or Berkeley CA or Woodstock or whereever else. Its just quite surreal & I still haven't gotten over it.

I've lived there for several years, and in no way do I identify with this post. Not even close.

It is good to be optimistic, but I'd hate for people to get this impression that the streets are paved with gold and make some really poor decisions.

While I respect your opinion, I will say that for someone from the midwest who's never been to SV until yesterday, it does feel like something out of a science fiction movie. Its just so vastly different out here in the midwest. Hell, I can't start a conversation about currying and mapreduce even if I stand in the middle of my university's comp science department and scream. And yet, in SF, the buzz is so palpable it feels outright weird. In the span of a few minutes in which I sipped some coffee, the chap next to me drew up some enterprise routing system for something called postgres. Another bloke gave a demo of some ipad thingy called doctor krono. And a third chap was going on and on about some series A series C thingy. I dare you to find a place in Chicago where all of these things happen. Or even any of these things happen.

> for something called postgres.

> And a third chap was going on and on about some series A series C thingy.

Ok, this has to be a subtle troll...

Exactly, which is why I wrote this post. There is a lot of cool stuff happening here, and a lot of money floating around, but nothing comes easy.

If it makes you feel better, my sense from what I've read is that you're more likely to have success once you get funding. You've been through a lot of pain, and you still believe in yourself and what you're doing. And apparently some very experienced and talented people believe in you too. That says a lot.

As for the "Somebodies", it's not all about past success; there is a lot of luck and flair to it. There are, in any human culture, people who are utterly worthless but can make the magic happen. They don't know much technically, but they're great at using the herd mentality and certain exploitable vulnerabilities in weak minds in order to make other people like them, so getting funding and press comes easily to them. When they actually have to build a product and a team and a company, they're screwed, and they tend to flame out catastrophically. Whereas the people who actually work hard and have real capability will have slower paths to success but, when they get there, they'll be able to stay where they are because they've actually earned it.

This is generally quite true.

It's not unheard of that I'll be hanging out at a cafe in Palo Alto and run into other entrepreneurs I've met before.

I went to a talk at the CS dept at Berkeley and ran into a direct competitor (who actually had my app installed on his phone). Had a great convo with him.

I've also had people come up to me who are in similar spaces who propose a possible collaboration.

Most people I meet who visit SF to do a little recon end up deciding to move here permanently because the environment is so great and supportive for entrepreneurs.

Chad, Couldn't have said any better about startups being hard. I wish you and Paul success. You have so many things that are going right for you. Access to great mentors, being part of YC, being in the valley and having a supporting family. You just need that missing piece for which people would really pay. As a nobody, you have not much to lose. We will be here to cheer you on when you find that missing link.

I think that the "making something people want" at the right time is the hardest part, and maybe distribution as well.

Execution is important.

But I think many people have the skills to create what ends up being successful.

Take Groupon for example. It made something a lot of people wanted. Could most people on Hacker News have made it? Sure.

But Groupon created it before anyone else (I might be wrong about this?).

Another example is HN. Pg has said that what he thinks users want most are quality articles and discussion.

While it's "just a forum", I think Pg is right for not adding a lot of features, or spending the limited time he has working on the UI, and instead focusing on how people can discover quality articles and make/read quality comments.

"Make something people want." It's simple, but it sure isn't easy.

Take Groupon for example. It made something a lot of people wanted. Could most people on Hacker News have made it? Sure. But Groupon created it before anyone else (I might be wrong about this?).

Group buying has been done many, many times before, going back to the bubble. Many millions of dollars were burned to little avail. What Groupon actually nailed was all the hard parts of the business model that don't look really freaking difficult on the napkin -- particularly "signing up local merchants" and "cost-effective customer acquisition."

That second one is relevant for virtually all businesses and gets disproportionately short shrift here.

>What Groupon actually nailed was all the hard parts of the business model that don't look really freaking difficult on the napkin -- particularly "signing up local merchants" and "cost-effective customer acquisition."

I may be misunderstanding what you're saying, but signing up local merchants doesn't seem all that hard. There seem to be many Groupon clones that have produced deals with merchants.

The main problem for the clones is not having Groupon's scale/distribution.

I think what Groupon got right was the simplicity of its offering.

One page that clearly explains what you're getting, at at least 50% off.

When looking at an offering, I see a picture, a short and sometimes funny/interesting description of the offering, short crisp bullet points about restrictions, how many people have bought it, how much time is left, and contact info -- specifically where the place is located.

That's really easy to understand. The user can vote yes or no in a minute or two.

Focusing on the hard parts is a commonality to just about every successful startup story. It's not always pretty or interesting, but the business flows to their doorstep because competitors can't get the hard stuff right or keep up. Startup security is doing both what is hard and not attractive repeatedly until it looks both easy and fun.

Great reminder patio11

I think Pg is right for not adding a lot of features, or spending the limited time he has working on the UI

I believe HN's plain design is actually an intended feature, not a bug. From one of PG's essays:

So the most important thing a community site can do is attract the kind of people it wants. A site trying to be as big as possible wants to attract everyone. But a site aiming at a particular subset of users has to attract just those—and just as importantly, repel everyone else. I've made a conscious effort to do this on HN. The graphic design is as plain as possible, and the site rules discourage dramatic link titles.


>I believe HN's plain design is actually an intended feature, not a bug.

I agree. Though I've read several comments that suggest adding to it, and in general, I think doing that would make it less useful.

Here's another bit of sunshine to brighten your day:

Looking at the stats, and hanging out on HN for a while, it occurs to me that having a successful startup might be the coolest thing you do in your life business-wise. A zillion guys kick ass on a startup after college, only to hang around the community for decades afterwards, looking to write a check, trying to get back in on the action. As rare as profitable startups are, repeat entrepreneurs are even rarer. Maybe you're that one-in-ten-million guy. Probably not.

So if it takes 20 years, I wouldn't sweat it. If there's one thing I've learned to believe in, it's that everything in startups takes a lot longer and is a lot harder than you think it is. So even when you imagine this really tough and difficult journey lasting for years, it's probably going to be worse than that.

I'm not saying that to encourage you to give up, I just wouldn't spend a second of my time waiting for the calvary to arrive, because they aren't.

> "...everything in startups takes a lot longer and is a lot harder than you think it is. So even when you imagine this really tough and difficult journey lasting for years, it's probably going to be worse than that."

Never a truer word spoken.

It's anecdotes like these that reinforce my belief that for a bootstrapping pre-success founder it's easier to focus on revenue rather than investment. The growth curve might be slower, but the friction you face as a first time entrepreneur trying to raise money is deadly.

You are still in a better situation than many here. SF's coffee shops are littered w/ debt-laden (pseudo)-hackers who have half-baked ideas/projects, no gf's (or wives), zero connection to anyone of value and sleeping on a sofa of some friend's musty apartment.

Haha I get lots of my work done at coffee shops. :)

Someone offered me a job recently. One of the people who interviewed me knew I had a side project that could become a startup. His advice was exactly what jazzychad said: startups are hard. He had been in one, so his advice meant something.

I turned down the offer, but for reasons unrelated to my side project. Still I feel like my project/startup is floating in the Sargasso Sea. If you think getting funding in the Bay Area is hard, move to Atlanta. There's a reason Stammy is out there.

And you can't be too much of a Nobody if you can get into YC twice. I wish team Notifo (or whatever your next project is) all the best.

I think there are different degrees of Nobodiness and Somebodiness, but I also think there is a pretty big gap between the highest Nobody, and the lowest Somebody. Maybe I am moving up the Nobody scale :) I don't want to belabor the point or make it seem like I am self-deprecating, but you get the point.

> I think there are different degrees of Nobodiness and Somebodiness

Indeed. You now at least you know a Somebody or two. Many folks don't get that far.

A misquote from the article (my perspective):

> Am I jealous of other companies' success? I would be lying if I said no. I am slightly jealous when I wake up and read another story about some company getting into YC when I didn't even get an interview.

I'd also be lying if I wasn't genuinely happy for every company that gets any sort of success, because I'm now getting a taste for how hard it really is.

I think the nobody/somebody line is oftentimes: "were you a part of a team/company that made money for investors". If you are, it seems like funding often falls like rain-- people think whatever alchemy that company had might have rubbed off on you.

Brilliant post, Chad. Many thanks.

Great post! The thing that really rang true was the part about the fundraising/depression/derailment, and how that can lead a start-up to consider some random/terrible offers that would otherwise be totally bogus. Paul talked us off a few bad-acquisition cliffs as well.

We certainly went through all of that at Jamglue. It's absolutely true that being a founder, especially the fundraising part, requires a really thick skin.

Each time I think about doing another startup, I start having flashbacks to broken termsheets, bullshit EBITDA projections, and VC's telling us that they could introduce us to Quincy Jones (I swear, at least 7 different people told us this). When we came out of our fundraising stint (penniless), we realized that our product had suffered and we were completely broken people.

The ability to be self-aware about the emotional roller-coaster is invaluable, and essential to forward progress. Thanks for this honest account so that others can make some sense about what they are feeling.

This is the reality. I well remember hearing Steve Blank speak when he said nine out of ten of us in the audience would fail. But he said each of you are thinking that you will be the one who succeeds and are feeling sorry for the other nine. I didn't realize it at the time but he defined what it is to be an entrepreneur for us.

Your problem are irrationally high expectations. Most of us suffer from naive optimism and that is a great motivator, a harmless one if we use it to fuel our enthusiasm while working late at night. The problem arises when dehydration makes you see an Oasis everywhere, when you become delusional. We humans suck at calculating expected value, particularly when there are huge outcomes with very very very tiny probabilities. That's why so many people play the lottery and that's what you're doing: playing the lottery, and there's nothing you can do to win it. Even with your perseverance and focus, with your knowledge and hard work, if you win it you are just very lucky. On the other hand, there's a lot you can do to be happy. With your youth, your wife, your intelligence, and your hard work, if you don't reach a state of emotional satisfaction then you are very unlucky.

My advice to you would be to define your threshold of success as something you can control. Focus on your surroundings. Get one client and satisfy him. Don't do it for money but for the pleasure of having an impact on somebody else. You can be your first client too; in fact, that's what we did when we built Spottiness: it's for us, we do what we can, we are nobodies and we don't care.

As an entrepreneur reading your post, I couldn't sympathize more with your situation. Startups are hard, startups are not for everyone and as Arrington would say, you are not a pirate until you start a company.

However, I would change your attitude a little bit. In your post you seem to focus on your sacrifices and being jealous of other successes. Well, when I see that Color and other startups raise a ton of money, I get SUPER excited! Why? Because if they can do it, I can do it too! As far as sacrifices go, realize that you are still better than 90% of the entire world. Being grateful for things that we have is a force multiplier. I am grateful for what I have and having the opportunity to build a company in Silicon Valley is a life long dream come true. Dreams are bigger than sacrifices. If you believe in yourself, you believe in your product, your customers will believe in you and your investors will too.

Good luck. And enjoy the journey, in the end life is just a game (whether you are a doctor, investment banker or entrepreneur, we all have finite amount of time on this planet).

"The less you need money, the more people want to give it to you." - some advice I have heard about finances. Applies to businesses selling a product, startups looking for money, and, especially well, to scholarships.

The best indication that people should invest in you is that you don't need them to invest in you at all.

so wait, is notifo.com going through yc again? (I only ask, because if not, and notifo is dead, that sucks)

Notifo is not dead, but the future is not certain (just as for any startup). We are going through YC again in order to figure things out and really figure out our direction for the future.

Did you reapply? Is yc taking another cut (ownership stake)?

Are you going in with that product?

We are going in as founders with ideas. Some info we can't reveal just yet, so I'll have to leave it at that.

Well heck, getting into YC is a feat unto itself. Considering all of the others that can't even get that far, at least you have a glimmer of hope.

Edit: I'm curious - why the downvote?

I didn't downvote you, but if I had to guess, it'd be because people perceived "at least you have a glimmer of hope" as downplaying or minimizing their struggle.

Not at all. As someone going through very similar struggles, I can relate 100%.

That's what I figured. :)

Great post.

I've also had "Startup depression" where I didn't sleep for 1 week and was totally unproductive for a grand total of 2-3 weeks. Ever since then I stopped recommending doing startups to my friends.

We've also experienced the "You're Nobody until you're Somebody problem." The work-around we're trying right now is to bring a (non-technical) "Somebody" onboard as a partner/founder, who is also, unlike us, located in the US where our market is.

Location has also come up in this thread. Early on I thought that thanks to the Internet location matters "less". Not true. You have to be where your investors/customers are. Deals require massive face time.

Are starups really that hard, or do they just require certain skills? Is it luck? Are you in the wrong place in the wrong time? Do you just lack the necessary skills? Do you lack the social support?

In school, you just gotta do what the teacher tells you to do, and you get an 'A'. You get a job and you just gotta be able to do what your boss wants you to do. Startups require you to find your own nitch, and do something different. No one is telling you what to do.

So, you can work real hard and work like before, but end up pursuing an empty hole. However, is this really harder?

What I find interesting, is that you can build a fairly large and profitable bootstrapped company, but unless you got VC money in the Silicon Valley the standard way, from the right people, you will always remain a bit of persona non grata, not particularly liked by Arrington, Techcrunch and the establishment. There will be no hype, no press, even if your revenue is larger than say Digg's in its heyday. I am speaking from experience, but I know of many other examples.

I think startups are like poker.

- they're 80% luck and 20% skill

- but the people who have been successful work hard to promote the idea (which they also generally believe) that they're 20% luck and 80% skill.

Good luck to you guys! I've known Paul a couple years and even helped him catch some bugs in Skribit back in the day. The article was very interesting as a friend and I are just starting to design and develop on an app idea that started out--like many do-- as a very small humble idea but with a lot of dreaming has evolved into an interesting solution. Good luck on Notifo, and with any luck maybe we'll cross paths somewhere.

I can't believe how much you sacrificed. Here I am thinking I had it hard. It's so great that you are upbeat and energetic long after the YC days despite all your sacrifice. Best of luck to all your efforts!

Strange and pathetic as it may sound to my non-startup friends, I couldn't agree more on the point of having a support group. Everyday there are things pushing my limit, and if not for my friends, I would have gone crazy by now.

Thanks for the great post! I don't think you'll ever quit until you succeed. I think the key to creating that one successful company is about trials and errors. "Learning doesn't happen from failure itself but rather from analyzing the failure, making a change, and then trying again." Don't be afraid to fail early and fail often, until you hit the nail right on the head. One thing I didn't understand from looking at your project is, why did you feel the need to get funding to begin with? It doesn't cost much to keep a website alive, and you have the support of your wife in order to continue developing for Notifo or a new project. I'm also a co-founder myself, so I'd like to know if there's something I'm missing here. :) Another thing I'm curious about is, why you're so set on sticking with Notifo, instead of moving on with a new idea? Is it because you already have tons of users and you need money to expand your company? I've only been involved with one website and I'm still learning, so it'd be great to learn more insights so I know what to expect ahead of time. :)

Why raise money? We wanted to expand and move faster by hiring and finding office space. That takes a big chunk of money. Also, we are paying ourselves meager salaries in order to pay rent/bills, which also takes money. If we hadn't raised a Friends and Family round early last summer, we would already be dead. Raising another round was supposed to help us grow.

Great post Chad, people thinking or already starting startups have to wake up and stop believing that if every second article on TC is about another funding, that there is already money waiting for them.

And with regards to Nobody / Somebody.... this post, might get you closer than you think to Somebody ;)

Good luck! You have the right product. Think what's missing...and is it really money?

Great read! It's great to hear some of the brutal truth about attempting to do what we all love to dream about but mostly FAIL at.

Startups are harder than anything I have read online (yours definitely put another well needed perspective on this subject). I have also wondered why none of my investors (or even YC) asked what the founders sacrificed to do what they do.

I"m so glad that your plan to go thru YC again worked out. Beer time! I so believe in you two and can't wait to see what comes out.

Beer time indeed Thomas! Thanks for chatting with us when we were down in the dumps. :) You guys are part of our startup support group. One of these days I'll be able to make it to one of your basketball games!

Wow you went on a cruise? You have money in the bank? You're going through YC again? Sounds awesome! Focus on the positives. You'll regret getting down in the dumps now, when you look back and realise how good you had it. Make the most of now and stop worrying so much.

The cruise was a Christmas gift from my in-laws. No way we could have afforded it on our own :)

Yes, there are plenty of positives to focus on, and that is what we are doing. It doesn't mean that there aren't still struggles.

Certainly and it's good to hear about the struggles. I was chatting with a guy the other day about how little information there is about failure and how then only really spectacular failures make the news. There must be so much we can learn from people who don't quite make it, or who make it small time!

When reading this post, though, I was just a little nonplussed at why you were telling me how hard it all is when it seems as though you're going pretty well.

Wow, your catharsis really comes through in your writing. If nothing else, maybe there's a memoir in all this ;) Seriously though, stay positive and stay in the habit of asking people for help when you're stuck. And don't just ask investors, 'cause their agenda might force them to say 'double or nothing' every time. Ask friends, other tech people, people who work on FOSS, old college professors, online friends. You need to develop, but you also need to spend a lot of time in front of other people. Also, make sure you're doing something you like. If the work is not rewarding, find something that is.

Kudos to you for saying and admitting the hard things for the startup entrepreneur. Failing sucks. Struggling to not fail sucks even more because it can just drain you. Best of luck :)

I understand the frustration when things are not moving along, but finding a solution to that is the only thing that filters out successful startups out of all the other startups.

All the best with your YC Summer 2011!

For what's it worth - Tim Westergren of Pandora pitched 300+ VCs before he raised money for series A. More on it: http://www.businessinsider.com/pandora-300-vc-rejections-201...

"if you are having trouble putting together a round in the first few weeks of actual investor meetings, just say, "screw it," and get back to working ASAP." - this seems a little extreme, to say the least, not sure I agree. It might apply to some premium selected YC startups in frothy Silicon Valley conditions, but not in general. Putting together a round takes time and quite often much much more than a few weeks.

that's why I say "of actual investor meetings." doing all the intros, and phone calls, and scheduling leading up to the meetings can take quiet a while and are necessary. But after you get to the "meeting phase", you really don't want to be spinning your wheels too long.

So startups the YC way are hard. The sacrifice is self-inflicted, and avoidable - just give up more of your company up front, or choose a more visible partner, or have a spouse that has a real income to start with, or work at BigCo then quit and create something they need and lease/contract it back to them, etc.

Its winning the lottery that is hard, and only because you make it hard on yourself for that big prize.

No pain, no gain.

The truth is, it hasn't been worth it at all... yet.

What about being your own boss? What about learning & producing at 10 times the rate you would at a desk job?

Also, I think you'll find there are plenty of "Nobodys" with past successes. Don't do it for the fame.

Those fall into the "hard to quantify" category. They are positives, yes, but there are equal amounts of negatives to go along with them. Hard to measure exactly, so I went with the easiest way to measure "worth it" in terms of running a company... finances.

Thank you for posting this ! The whole post means quite a bit for me. Almost every word you write feels familiar.

I wish you good luck with with your startup. Actually I wish all startups having difficulty raising the next round good luck.

I'm right there with you Chad. We've got a strong team, yet are still weeks away from launching, and it's just truly amazing how much failure and rejection we have faced over the past few months.

What a bloody good read......they say nothing in life that is worth having ever comes easy....stay there chad...grit it out....you'll reach where u want....success will come..good luck have fun

Thanks for sharing this Chad. It means a lot to me, for someone who is just getting into startup life with wife and kid to support, giving up a well-paid 'secure' day job.

An inspiring poem shared by my friend. Was read out by Winston Churchill at the beginning of Second World War.


SAY not the struggle naught availeth, The labour and the wounds are vain, The enemy faints not, nor faileth, And as things have been they remain.

If hopes were dupes, fears may be liars; It may be, in yon smoke conceal'd, Your comrades chase e'en now the fliers, And, but for you, possess the field.

For while the tired waves, vainly breaking, Seem here no painful inch to gain, Far back, through creeks and inlets making, Comes silent, flooding in, the main.

And not by eastern windows only, When daylight comes, comes in the light; In front the sun climbs slow, how slowly! But westward, look, the land is bright!


Here is the paraphrase shared by the friend:

Don’t say that the long struggle [against tyranny and injustice] is of no avail; don’t say that all your efforts, and all the injuries you’ve sustained, were in vain. Don’t say that the enemy’s just as strong as ever; and don’t say that nothing’s changed for the better!

If the things you hoped for haven’t happened, well, maybe the things you’re scared of won’t happen either. Perhaps over there on the battlefield, now obscured by smoke, your comrades are chasing the enemy away, and all they need to ensure victory is that you go and join them.

Look! Those waves don’t seem to be making much headway, even though the tide’s supposedly coming in. But far behind you, unseen creeks and inlets are swelling with incoming waters: the sea really is on the move after all!

Look! The eastern window you’re sitting at isn’t the only place affected by sunrise; from there, yes, it’s true, the sun hardly seems to moving up the sky at all— but cross the room and look through a westward-facing casement: see how the whole landscape’s already flooded with light!

Clough had just personally witnessed how Garibaldi's brave attempt to help preserve a new Roman Republic had been foiled when the forces of reaction (led, ironically enough, by the French) had successfully brought the Siege of Rome to an end in 1848. He was trying to cheer up fellow-supporters of reform and of independence for Italy. They were all feeling pretty downhearted. That's the historical context.

Super duper post, Chad. What you've done so remarkably in this post is you've captured "truth." Looking forward to one-upping you in comparing sad founder stories over beers.

Good read. I hope you make it someday!

Wow, thats an eye opening picture of startup life. I really hope these guys succeed.

"A real entrepreneur is somebody who has no safety net underneath them." H.Kravis

I always thought notifo was a terrible idea. It doesn't really add any value. Change your idea please. I mean look at your services page. The number one thing is "google voice alerts" so you can save money by not getting texts. Let's say you save someone $1. There's no way they're gonna pay you $1 for that. Then you also list Skribit on that page, a dead service.

I would take the mobile notification technology and pivot to notifying about something people care about, like people in the vicinity with similar interests.

There are a lot of non-public facing services using Notifo for internal communication/alerts. We do have an app in the pipeline that is an offshoot of Notifo's tech, though... coming soon.

I'm sorry you thought it was such a terrible idea. It's hard to hear that coming from someone I have respected for a while and followed along with your successes with AR and CP.

The good news is that I care enough to say what I really think despite the definite collateral damage to my reputation by saying something negative and going against the grain of what everyone here is saying?

The social consequences to my statement make me think of pandas and lobsters - http://ifindkarma.posterous.com/pandas-and-lobsters-why-goog...

and I was eager to hear responses to my comment - perhaps related:


btw I've been rejected by YCombinator multiple times

I was eager to hear responses to my comment

I thought it was overly harsh and missed the entire point of the post. The article was titled "Startups are Hard" not "Ask HN: Please review my app" I greatly appreciated the honest reflection on how hard it is to start something. It mirrored many of my own experiences and provided a valuable counter example to the standard "Oooh, I fell out of bed into a pile of money" startup story that's usually tossed around.

Regardless of the value of Notifo or any particular case, startups (hell, all businesses) are hard and having people tell you your idea sucks doesn't really help all that much. Sucky ideas sometimes do extremely well (ie. Facebook, Twitter, and many more), and great ideas sometimes do terribly (ie. tons of shit we've never heard of because they're all dead).

You're right.

I certainly do not begrudge you your opinion. I completely respect it. Thank you for being honest and not worried about what other people might think.

Keep up the dream, screw going back to a 9 to 5 and something you settle for. Do what you love, I am in the same boat, I am moving down this summer to San Fran. and I think at times if I am making a mistake and say hell no! I rather be after my dream my whole life than settle for something. Its all about the chase of the dream.

Ps: Anyone wanting to meetup this summer in the Valley, I'm more than willing. Let me know. My first time. Rmena123 at Gmail

This post is one long moan. Of course startups are hard. So is marriage, and so is jogging. So if you're doing it, you'd better love it, because if you don't, you're going to be miserable. You do it because you love building things and love to learn things -- and you can handle failure, whether it's temporary or permanent. You can recognize that you have not actually failed if you've learned in the process, made personal connections, etc.

People doing startups need encouragement. They may need to be warned that this isn't easy, but they really don't need moans.

People thinking about doing startups do need views from different perspectives. The article is exactly that. It's not a moan, it's a pragmatic view from someone who drank the koolaid and is now seeing the reality, and shares it. It's probably something he himself would have wanted to read 2 years ago to have a more balanced view (even if he would probably have done it anyway!).

Yes, the article is not too positive, because the author is not at a great point. But it's far from a moan.

Also, some people doing startups do need encouragement, but some others need to be told that what they are doing is not valuable and they had better change course or go back home.

My apologies if it seemed like a giant moan. I was just trying to give a slice of reality about our personal experiences. Startups and the Silicon Valley Life are made to look pretty glamorous, and I wanted to offer another viewpoint.

I went into this whole thing being pretty naive about a lot of the process, so I wanted to relate some of the things I've learned along the way.

I'm not looking for pity.

Although you haven't cracked the big time yet, this still all sounds pretty bloody glamorous to me!

And, FWIW, I am not saying you have no reason to complain. But keep your chin up. If this one doesn't work out, you've learned a ton, and the next one will be better.

Let me guess: You've never been a real entrepreneur. :]

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