Walking On My (Startup's) Grave

Playing Against Doom

Startups are not a roller coaster, but a constant battle against death. (If that sounds like a roller coaster to you, I don't want nothing from whatever theme park you build.)

No matter how well you're doing, no matter how much money you have, you are constantly worried about death. Startup stall on growth? It's decaying. And decaying means dying. Growing but running out of funds and can't raise? Doom! Doom from lack of money, doom from lack of traction, doom from apathy! Death is always around the corner. As founders, all we do is stave off different types of death. As far as I can personally tell, this sense of ever-present doom doesn't seem to go away as things get more successful. In some ways, it gets worse. The bigger and more you grow, the scarier the prospect of death seems. So is death creeping into your startup? And what does that really mean anyway?

Dead or Alive

In your real life, it is really easy to know if you are dead or alive. Metaphysical ruminations aside, if you are dead, you most likely won't be waking up and doing stuff. In most cases, friends, family, and acquaintances will know you're dead. When you're dead, all sorts of things you were capable of doing are no longer possible. It's a full stop. But with your startup? How do you know when your startup is truly dead?

What if, heaven forbid, you are just pushing along a zombie startup

Sometimes you can't put a finger on the exact reason you know your startup is dying (though lack of growth is a pretty good one in general), but you can always tell when things are taking a turn for the worse. And then, there's a moment when you wake up and feel like everything is totally 100% definitively fucked. You may recognize this moment as the instant you turn to your cofounder and say something like "we are so fucked. we are so totally fucked and dead." 

Then you kinda lean back in your chair, breathe out real deeply, and everyone decides to go home to think on it. 

And so you are faced with impending doom, and no matter how hard you try, you can't get the damn startup to grow. You feel like you've tried every thing possible.  No matter how sexy your graph is, how fancy your pitch, you can't close the damn funding. You can't seem to get a YC interview! Or even worse, you just got rejected after an interview! You sit up at night procrastinating, ignoring that gnawing sense of failure in your gut until about 2am when you decide it's time for your startup to die and you're going to write up that email... in the morning. You're going to do it, but you just can't do it right at that moment. But you decide that in the morning, you choose death.  


But hang on a second. If, in fact, you don't raise money successfully (or get into YC), are you well and truly dead? Is your vision, your dent in the world (or whatever) snuffed out because some guy in a collared shirt won't write you a check? If you don't get that launch article, or don't get invited to that conference, has the dream died? Even at the worst, when everyone is laid off, and it's just you and your cofounders on the curb, are you dead? Death in Startupland should always be taken with a grain of salt and is often grossly overstated. 

In the end the only way you die in startups truly and unequivocally is when you decide it's no longer worth carrying on. The moment when you say "enough, I can go no further" is the actual moment when your startup dies - it's when the founders choose death. Not when funding doesn't happen, not when customers leave, and certainly not when press and peers say so.

So you wake up in the morning, and you are ready to give in to startup death, but for some reason you just can't. You know everything is wrong and not working, but your dumb head just won't let you choose death. What if you rebuilt a core piece of the product that never got the love it deserved? What if you focused on revenue over user growth? What if you tried a slightly different market? What if you just kept trying?

At this most dire darkest moment, when doom feels certain, you're still restless and the impetus to build is still there. This is probably the most overlooked and liberating moment for a founder. In those worst moments, you realize that as long as you're willing to push forward, then things aren't actually dead. All the press, the funding problems, the whole silly stresses of startup land, and the pressures therein fade away because they were never important to staying alive in the first place. The only thing that matters is you and your cofounders' determination to stay alive. When you decide to stay alive, you realize the secret of beating startup death is very simple: You refuse to die. 

Raising of Lazarus by Juan de Flandes with a minor alteration from me.

After reviewing about 30 YC Apps, here's some general advice

Demo day just wrapped up for Beacon. We feel pretty good about what we've done since starting YC in January. 

But it's been a long and winding road to get here. One of my cofounders (@dmitric) and I have applied to YC six times, getting in for the first time for Beacon. I dropped a note about it on HN last month and said I would be happy to help anyone applying and hopefully avoid all the stupid mistakes we made the first five times. 

Since then I've looked over about 30 applications and here's some global advice that I gave based on what I saw and my own experience. 

The goal of your startup is not to get into YC

So many people think that YC is an arrival destination. It's not. It is a teeny tiny stepping stone that may or may not help you get to where you want to go. Don't get me wrong, getting into YC is useful for any company, but at least for us, the timing was right because we already had signs of growth, and used the time there to really blow things up big. 

The real goal is to build a company that grows, generates value, and captures value. That means making something people want, making money off of it, and exploring how big it can get from there. A company is just a vessel to explore an experience or product that you think is valuable, and to reveal just how valuable it really is. If your ultimate goal is just to get to YC, you'll find that you've wasted a lot of time getting there, because once you're there, you basically just spend all your time working on your company. 

It is very obvious when people applying have the "if we just get into YC then we'll get money and then it's all easy" attitude. This is a recipe for disaster - whether you get into YC or not! If you're not excited about all of steps it takes to make a company, even the little (shitty) challenges of your company, there's literally nothing anyone can do to help you make things happen.

For us, YC was just something we applied to every 6 months. We knew we were going to keep working and building stuff no matter what. And funny enough, the more we focused on building, the closer we got to getting in with every step.  

Growth > everything

There is really only one thing that matters in startups and that is growth. Everyone says it, nobody listens. But it is the only thing. Every other bit of advice is more or less bullshit without growth. All good founders will tell you this. 

So when you're filling out your application - quickly and explicitly state what your product does, and then get to the damn growth! 

YC partners are reading thousands of applications. But growth really stands out. Even the most banal or tired ideas can seem like real gems if growth is there. There is an outside chance that you have an idea so novel that it stands on its own, but the chances are slim, and even then, you could still probably find a way to show growth in interest (like a sign up form) for what you're doing. 

Be committed to the cause

Founders that can't commit to being at YC or work on the startup over the months that YC happens are a huge red flag. YC is like a bootcamp - you just work, eat, work out, work, sleep - and the only people you really have for support are your cofounders. It's a huge signaling problem if part of your team can't commit, and means that most likely, this startup isn't the core passion for that person. Jessica Livingston talks a lot about how founder breakups are the number one reason startups die. 

Starting a startup is like going to war with hundreds of millions of people except instead of attacking you, they just do not give a shit about what you're doing and ignore you all the time. It's incredibly disheartening. The only people who really care are you, your cofounders, and maybe like the 10 people using your service. And in reality, when the chips are down, the only people who really care are the cofounders. So you want to make sure you're all on the same page before diving in, and YC definitely wants to figure that out before bringing your team in. 

Seriously, Growth > everything (or, why don't you already have sign ups?).

Everyone has beautiful unique snowflake ideas that, when dreamed up in the ephemera of the mind's eye, are perfectly working business entities that print money and change the world. Your ideas are beautiful, and it's great that they're exciting. But they're also not real (hélas). The good news is that you can make them real. And you make them real by building something and increasing the number of people who use it over time. 

Do not tell me how your idea is going to work, show me that it is working. That is far more convincing. Every idea out there has been dreamed up (save money on loans! deliver fresh food instantly! monetize journalism!), but very few actually grow. No YC partner (or person alive) is able to predict 100% of the time which ideas are going to be massive. But if you have a graph showing rampant growth of users or revenue, that's a pretty good indicator that there's something there. I may think delivering flowers is the lamest idea for a startup ever, but if you're growing your revenue and sales by 10% every week for 8 weeks, then you could change my mind and pique my interest pretty quickly. 

Lastly - because growth is nearly the only thing that really matters, if you can't get growth, then you should probably hang up your boots and retire from founder life. Founders that stand out are zealously devoted to making their products grow. If you believe in what you're building and are truly passionate about trying to turn nothing into something, you will find a way to keep it growing. Growing focuses your efforts and helps define crucial decisions. 

Pick a key metric, define the interval (weekly, monthly, etc.) and then just push yourself. Don't look back, and don't worry about all this other nonsense. The rest will take care of itself. 


discuss on HN

feel free to email me or say hi on twitter. thanks for reading. 

thanks to dmitri for the edits

From Backspaces to Beacon

I’ve spent the last year working on Backspaces because I was (and am) convinced that storytelling will forever be the defining activity for the human web. What I mean by that is, amid the endless streams of data, the commoditization of behavior, and the aggregation of interaction, narrative is the only thing that’s actually worth a damn. Storytelling is one of our best tools to articulate the universality of the human experience, and it’s in our best interest to enable it as much as we can.   

Backspaces was our attempt at bringing storytelling to the mobile web, with a photographic slant. It’s a fantastic product and we’ve had a lot of fun building it. When the community started growing, Dmitri and I were completely humbled by the incredible stories people were sharing.

We devoted a lot of time and effort into making Backspaces a “social consumer app” because that’s where we thought the big opportunity was. Personally, I was looking to macro trends and saw mass adoption as the key to Backspaces’ survival. User generated content as a model only works if there are millions and millions of creators.

But what we discovered with Backspaces is that creating good stories is really hard. More importantly, the economic model for web “content” is mostly ambivalent to the actual content itself, and more concerned with how high the pageviews are. When we saw that no story, no matter how poignant or beautiful, was going to beat a Buzzfeed cat listicle in terms of pageviews, we realized there was a huge problem with the whole model for storytellers.

So we began thinking of the problem at its root. And talking to smart people about it. People who were obsessed with the same problem. And that’s how we met Dan Fletcher, hot off his exit from Facebook. In three short months, we worked with Dan to put together a service that believes whole heartedly in the value of stories and storytellers. I won’t blather on too much about it here because we’ve said plenty elsewhere.

It’s a really simple product - find a writer, fund them with a $5 monthly subscription, and get access to every single story and writer on the platform. It’s like Netflix and Kickstarter rolled into one great experience for journalism. And it’s live right now. 

It’s with great pleasure and excitement that I introduce you to Beacon, the best way to empower writers by funding the work they do. 


Shitting on Quantified Self: Fitter, Happier, More Productive.

The other day I had beers with some friends and noticed one of them had a Nike Fuel Band. We got into it (we were a touch sauced to be fair) where I was basically ripping on the whole notion of the Nike Fuel Band. Most of my friends in tech know that I shit on quantified self every chance I get. It ruffles my feathers, and I instantly put on my grumpy blowhard curmudgeon hat. 

The more I think about it, the more liberal-arts-degree I sound, and perhaps that betrays my narrow mindedness about the whole thing. So now Nike is going to tell us how many steps we should take? Nike is going to help me understand health because… Nike is a good samaritan? Love the mutual win-win of me striving towards a quantified goal, and Nike selling more shit to get me there. Do child laborers and sweat factory workers have Fuel Bands? I bet their scores are off the charts! 

Ok that's the emotional reaction, the geezer reaction. And it's probably no different than how the generations before felt about TV, and before that, radio, and before that, those raunchy dirty (delicious) Shakespeare plays. 

And aren't I just a hypocrite? Seeing as how I used Google Maps to get to the bar, which told me how long it would take and how to get there. As my friends would argue, is the device telling me what to do, or is it just a dumb machine that provides me with information that I request from it? And who says that quantified data is the only thing controlling the Fuel Band wearer's life? Why can't quantified data merely add more information to help inform decisions I make, just as much as qualitative ones do? What is so wrong with measuring it?  

I really can't argue against any of these points within the context of the discussion. Ultimately, the Fuel Band is a tool like any other - use it, like TV, at your own discretion. 

The world is a more orderly and organized place because of research, data analysis and a/b testing. I prefer Mailchimp newsletters to random poorly designed emails, there's no argument there. There's nothing wrong with using science and measurement to help change things in our lives. I'll never argue against that because I'm thankful for science in as much that I've never been prescribe a drop of wolfsbane in the ER.

So I grumbled and mumbled something about Radiohead and the Matrix but conceded the debate and we parted ways. 

But days later, something still bugs me about the Fuel Band. Quantification, at least in my limited world view, seems to be a convenient end goal for discovery. We gravitate towards numbers because they're so easy to understand. How's your business doing? Use growth (where growth equals increase in profit) to measure it. Did the late great old man Scooter live a good life? Use fulfillment (where fulfillment = amount of happy activity * total number of days lived) to measure!

Not knowing is scary, but not nearly as scary as the relative uncertainty in the knowledge you have. Quantification is a fantastic way to ground that knowledge in relative truth... which just isn't that much different than just believing in deities. 

When I see tweets like "WiThings says I need to lose .5 lbs this week, almost there!" that depresses me greatly. You shouldn't obey WiThings' commands any more than the bag of Doritos telling you to keep eating those delicious Monsanto monstrosities. WiThings, and weight loss on such an incremental level, replace larger (and admittedly more nebulous) concepts such as "feeling healthy and happier."

And my Fuel Banded friends agree here. Quantification as an end goal isn't their intention. Quantification does less to help us frame our questions and much more to help us measure our discoveries. For them, it's the added measurement aiding in questions or desires they've already framed. 

Sounds good to me. But again, do I really believe the vast majority of people are so conscious of the limitations of quantification? The same world that gave birth to Bear Sterns, Enron, and Walmart is going to err on the side of couching quantification within the greater goal of living a "happy life?" 

Closer to home, tech is rife with data driven copy editing, and UX experts in search of percentage points. We are bombarded by tools that are designed to force a specific action from us. My phone commands me "Slide to unlock," my shoe company tweets "RT to win" and even my friends manage to get a few "likes" from me. Each of these interactions have been developed by very big and powerful corporations based on years of social data. Quantification to illicit a type of qualification. Buzzfeed. 

And look. I get it. The world is better with quantification... Because we can measure this arbitrary construct of "better." But in between the absolute of numbers, the messy realities of existence persist, not to be quantified and measured but simply to be experienced.

The Hustle™ - A Defense In Kind

Kyle Bragger, a friend and probably my earliest mentor in startupland wrote an article calling out the "hustle" as a false idol for entrepreneurs, builders, and people in general:

"The Hustle™ is bullshit, and a poor way to accomplish anything of lasting value.
There’s a pervasive and toxic way of thinking ‘round these parts that you’ve gotta out-hustle your competitors; that you have to pull all-nighters and throw away weekends to ship that new feature; that, by working double- or triple-time, you’ll execute better and pull ahead of the pack.


What did The Hustle™ accomplish? I gained weight. I wasn’t spending enough time with my (now) wife. I felt like shit. I began to resent my work, and the work I was producing clearly wasn’t my best. I started cutting corners. I went from a mindset of shipping with quality and integrity to “when is this going to be over?”

I can't find any flaw in what Kyle wrote. And Kyle is definitely a dude who's put in his shifts "hustling" so he knows what he's talking about. Dude does not bullshit. 

Recently there's been a lot of discussion and mounting criticism about the "hustle" life. Most of the talking points focus on working long hours, taking on too much stress at once, and the stupid belief that going "110%" will guarantee riches. Real tragedies both public and private abound in no small part to these beliefs especially now as seed startups are biting the dust from the boom of 2011. 

But why all this criticism focused on the hustle?

There are plenty of real problems in startupland - the herd mentality, the general dilution of talent and unique perspectives, the misogyny bro-culture, the disconnect from the 99% etc. But hustling is not one of these problems. If anything, there's not enough of it in startups. For me, the hustle has never been about working long hours or working harder than anyone else. I think in no small part, there is a misinterpretation of exactly what the hustle is. 

Here are some commonly accepted definitions of "hustle:"

  • To make money by any means necessary, legal or otherwise.
  • To feign a lack of skill while bets are made before a game of skill starts.
  • To move energetically or dynamically in a competitive activity.

Hustling in hip hop is a deeply American cultural construct. Money is everything. Do anything to get money. Hustling in skill competitions is a celebration of cunning, guile, and hacking the rules of the game.Hustling in sports is the 110% effort giving-it-your-all for the  whole match.

In each of these cases, the hustle represents the act of doing whatever is necessary to achieve a singular goal: Win. Hustling epitomizes a very focused (even myopic) obsession with winning. No matter what happens, the hustler will try any and everything to succeed. 

Hustling is never explicitly the act of working insanely hard, working insanely smart, lying, cheating, stealing, coercing, finagling, or scamming even if we associate these things with the term. In the hustler's mind, the "hustle" occurs when you win. The means are merely different methods to the madness. 

Some hustlers do work hard, and some work smart. They can be morally ambiguous at best, greedy at worst, but above all self-serving. In startupland, VCs love them because they represent the type of ego-driven power and cash hungry personas that map well to histories of exits and profit. It's not a guarantee of success, but it's certainly a good sign. 

And as Kyle and others have noted, the life of a hustler is a bunch of bullshit. The chances of it paying out are slim, and, for hundreds of millions of Americans, not even possible given the appetite for risk required. Instead you lose your health, your personal life, and your perspective on what it means to be a living breathing human being. Above all you focus entirely on winning… a ridiculously arbitrary notion of merit, and yet a very persistent one. 

So why defend the hustle? 

Hustling is a big fuck-you to everything that stands in the hustler's way. It is an irrational insistence about how the world should be. Hustlers actively perpetuate the Horatio Alger myth of rags to riches, a blatant lie about what is possible in America (statistically speaking). Occasionally, outside the bounds of the system, some of them succeed and things are forever changed for better and worse. 

The hustle is when you spend all your Paypal exit money on absurd dreams of the stars and electric cars. It's when you burn the park benches to keep the fire alive in your studio. Cook down leather boots for food in the winter. Hustling is defending yourself with the frying pan, Odysseus outsmarting the cyclops. Stealing the wrestling captain's girl while you're giving her math lessons.  Nothing celebrates the potential impact of a single human being quite like the hustle. 

The hustle is also when you sacrifice everything and nothing works out. It's Escobar in jail, Enron, the financial industry over the past twenty years, Color for iPhone. It's a yellow brick road littered with suicides, alcoholism, abuse, fraud and frighteningly reckless abandon. 

We love hustlers, especially in America. We recite Steve Jobs' famous quote "Good artists copy, great artists steal," rewatch the Larry Bird diving-out-of-bounds-behind-his-head assist, listen to the Jay-Z mythologies of getting out of the ghetto. It should be noted that none of these people come off as kind-hearted empathetic individuals. They only care about wining. We appreciate their singular driven goals clearly. We know that they wear not hearts but dreams on their sleeves. We admire their gumption. Their necessity is clear. And their invention is always genuine. Inside of every hustle is the soul of a determined individual filled with irrational belief.

Hustlers are rule benders and breakers. They push the boundaries of what we think is acceptable and possible. They are often the ones pushing the human condition forward AND backwards. When they're good, they're great. When they're bad, they're asshole lobbyists tanking our country. 

Above all, to hustle is to cause change. 

Bending and breaking rules to achieve something in spite of the odds. You could argue that hustlers are the only real agents of change. Tesla may have invented a bunch of cool stuff, but Edison was the jerk who brought it to millions of people. 

When we admire hustlers, something clicks inside of each of us. We are compelled to appreciate ingenuity and persistence in the pursuit of singular goals. Forces greater than our individual will are constantly at work against us, and so we cheer on the Stampers to make their log run. We believe in miracles on ice, buzzer beaters, muses for playwrights, angels for startups because we want all those people to win. Why? Probably some primeval animal instinct tied to resource acquisition and reproduction, I dunno, come back to me in 50 years. I do know that in America everyone loves the kid with the lemonade stand in the summer and the sweet smiling troublemakers in high school who sell lunch tickets for booze money (sorry mom!). 

But, if the hustle is basically some antiquated primal element of our psyche, shouldn't we, in our comfortable sophisticated society work to abolish it? They're trying this in Europe so the jury is still out on that one. 

Consider the creation of an individual human and all the processes and events required for this new person to exist. On the top level there is a tremendous amount of hustle from two individuals. But even before this, you must factor in six billion people, multiply by time and geography, then add a bunch of circumstance, and there's still so much work to do! There's that one egg that's got to make that trip (unscathed no less!), and then there's that one sperm who will need to triumph over so many peers (among other obstacles). After all this, there's still the mother's own will to persevere, and then the child's first moments in the world - kicking, struggling, and finally crying out to announce her presence in the world. And then they will need to get through middle school.

Human conception, conscious life as we know it, is just a culmination of a bunch of random separate entities that got what they wanted. So while you certainly can kick back and enjoy the life, please recognize that you can't knock the hustle. 

The best advice I've heard so far about building a company.

I had coffee with a fellow entrepreneur today. He wanted some advice about user acquisition with his new iPhone app. We talked a bit about the app, and at one point I started asking him questions about the current state of the app:

How many users are actually doing the things you hoped they'd do?
How many use it once or twice and churn away?
What is the real point of this app - not "at scale" - but right now?

Usually I ask these questions as a litmus test. If the entrepreneur starts giving me weirdly obscure answers or strange rationalizations for reasons why things aren't happening, I know they're trying to convince themselves. And I got weird obscure half-answers. 

If you struggle to convince yourself first, there's no way you're going to convince others. To put it bluntly, it should be clear that you are bullshitting yourself. In this case, my friend was bullshitting himself. 

It's funny because even a year and a half ago, I would be right there with him - trying to find some positives in what is there. But it's been nearly two years of failing now and I simply can't bullshit myself or anyone else anymore. There isn't enough time to keep doing that. None of us have that sort of time. 

So I told him some important advice that someone way better at this startup stuff told me:
Be honest with yourself about what you're doing and where you're at.
Ask the hard questions every day because no one else has the passion or belief to do it for you.

There's lots of great support in Startupland. It's crucial. But deep down, no one truly gives a shit about seeing your thing succeed except you.
If you can't ask the hard questions, no one will, and you will waste time building something that is doomed to fail.

You can't create real valuable products or services built on hopes and dreams of what will be. But you can do it by becoming obsessed with impossibly difficult questions and pursuing the answers to their fullest potential.