Founders Never Say Die

“Sir, we’re going to need you to move your vehicle, or the Secret Service will have to have it impounded.”

This was not, needless to say, how I had envisioned my day turning out.

Three weeks earlier I gave most of my stuff away, packed the rest of it in my 2002 Honda Civic, and headed for Silicon Valley to finish building and start fundraising for Grasswire. I didn’t have much cash, but by living in my car I could squeeze by.

I hadn’t, however, included my car’s complete mechanical breakdown on the 101 just a couple hours before Barack Obama’s caravan was set to roll through town in my financial forecasting.


The bad news is, I was no longer just poor; I was completely broke. I neither had a way to pay the bills that were coming next month nor the option to cut costs to live within my means.

And just like clockwork came those few hours of a weird entrepreneurial depression. When it hit, everything I’d done up to this point felt completely pointless. All of those hours my co-founder and I had spent conceiving and building this thing — all of that was just pixels on a screen. Why would anyone be so foolish as to think that pixels on a screen would ever be worth anything? We may as well have been running in circles.

It’s times like those that make creativity so terrifying. You made a ballsy decision to go against the status quo, convincing yourself that you could create something great out of thin air. But what if you couldn’t? What if the status quo was right all along? It’s the status quo for a reason, after all.

Yet these fears and this depression-like state are completely decoupled from reality.

When I find myself in that state I try to run a sort of a gut check. What if my company were Facebook? What if it were Twitter? Would I still feel the same way if I had millions of daily active users? If I had millions in net profit? How would I feel?

As an entrepreneur you need both the highs and the lows. When you hit a high you start to see your vision of how you could really take over the world. This will work, you tell yourself, and when it does, the world will be different because of this. But you also need those lows. This could fail because x and y and z. Our users don’t like this, our customers don’t like us because of this. And you get to work fixing them.

The highs are when you develop your vision. The lows are time for self-correction.

Yet if I’m honest, I never seriously considered calling it quits. Sure, I was floating on my credit card, which is something i promised myself I would never do, but I would make it work somehow; at least I wasn’t living on cereal like the Airbnb guys. I wasn’t millions of dollars in debt in my own name like Chris Sacca was either. I had no idea how I would make it, but every time I considered going home the words from Sacca’s legendary PandoMonthly kept popping into my head: ‘That’s just not a @#$%ing option.”

And I’m kind of glad I waited a couple weeks to write this, because now I can say that I figured it out and paid everything off by hustling for a while on one crazy Saturday (more on how I did that in the next post… it was kind of sketch but it worked out).

I can’t say with surety that grasswire will be successful, but this I do know: If it goes down, I’m going down with it.

Here’s to living the dream.

AngelList Syndication Changes Everything – And Nothing

AngelList syndication is shaking things up.

AngelList syndication basically lets you say, “If so-and-so invests in a startup, I’ll automatically invest $x.”

For example, Tim Ferriss yesterday picked out Shyp - a startup he would invest in, and offered to let others invest alongside him. Shyp raised $250K in 53 minutes.

Jason Calicinacis, at the time of writing, has $216,000 syndicated from 28 backers – that’s after day one. He proudly announced on Twitter that LaunchFund’s bandwidth went from $100-250k a deal to $250-500k. But is that really the case?

What’s really happening is the way investing has always worked is becoming more transparent. Investors blindly follow the most popular investors in hordes just as they always have, but now it’s official and automatic.

There have always been investors with a bunch of money and not as much time willing to follow Jason into a deal. If you had LaunchFund as a lead investor you would have no trouble closing up the rest of your round, probably with a very similar list of investors to those who are syndicates of Jason. Investors can be kind of like high school girls – if one likes you they all do. Raising money had an almost binary outcome – you would close up your round fairly easily or you would be spinning your wheels looking for a lead investor.

In that sense, nothing has changed, it’s just now immediate and more transparent.

Yet, for founders, who to go after and who is following whom will become more more obvious. If you land a Jason Calicinacis, you get pretty close to closing a seed round. If you land someone who follows Jason, who have a pretty good intro to Jason.

Honestly, it’s about time. Thanks, AngelList.

Voluntarily Homeless in Silicon Valley

I’m writing this post from the trunk of my 2002 Honda Civic; the place that I will call home for the next few months as my co-founder and I finish building and publicly launch Grasswire.

While the adventure has just begun, I honestly feel like this type of homeless lifestyle while building a company is not only possible, but sustainable.

Obligatory Backstory

A couple of months ago I left a link to our half-built product somewhere in the middle of a HackerNews thread. I hoped a dozen or so people would hit the site, look past our obvious UI/UX deficiencies, and give us some useful feedback.

Three days later we still had hundreds of people simultaneously on the site (most of our traffic came from Reddit, Facebook and Twitter by that point). Somewhere amidst the classic startup story of pizza, caffeine and the rush that comes from your server crashing from traffic as quickly as you can upgrade it, we concluded that what we were building had legs. The time had come to really pursue it.

We had been talking about the possibility of moving to Silicon Valley for a while, and had won some money in a couple competitions tech companies like ours had no right to be in (we finished 2nd place behind a popcorn seasoning company). But if I’m completely honest, it’s not about the money.

Candidly, living in a car in Silicon Valley had much more appeal to me than a single bed and a shared bathroom. If I happen to save some money by virtue of trying a new adventure, I’ll take those side benefits.  Much more than money, what fuels me is obsession with minimalism, reading way too much Thoreau, and trying to continually see life from a different angles (not to mention a passion for the company we’re building). It’s about questioning society at its fundamentals, and seeing what a life not tied down by a foundation really feels like. And so far I love it.

But How Do You ___?

The first thing someone will say when you tell them you’re living in your car is, “But how will you X?” X could be “sleep” “eat” or “shower,” but it’s never that complex, you just have to figure it out. Kurt Varner did an excellent job answering some of those questions on Quora, but since so many people ask, the run-down is this:

Sleep: Fold the back seats down, throw a mattress of some sort into the trunk (I recommend a slim air mattress generally used for sleeping on cots), and you’re golden. It still leaves plenty of room to store stuff.

photo 4

Eat: Don’t buy perishable stuff. The trunk actually stays cool enough to store things like cheese, but milk isn’t recommended. The Hacker Dojo (see “work” below) also has a break room style kitchen. You won’t want to plan on cooking there, but the microwave will get you by.

Shower: Stanford has free showers designed for those that use transport (please don’t abuse them), or you can get a YMCA or gym membership.

Work: The Hacker Dojo is only $100/month, allows 24/7 access, and includes the only thing more important than food or water: a 100 mbit Internet connection.

Park to sleep: Palo Alto hasn’t yet passed a law that makes living on the streets illegal, but I usually just find a random place that’s dark where there are a few cars (to make sure it’s legal) and climb in the back. Last night I was in front of some random people’s house and they were coming in and out and never noticed. People aren’t that observant, it turns out.

Jumping In

I have had my share of part-time, college-kid-grunt-work kinds of jobs–the kind of “sit at a computer and enter data until your eyeballs bleed” kind of job that makes you generally miserable. This is how I learned an important lesson: If you hate your work, you won’t just be miserable at work. Misery will spill over into your evenings and weekends. Eventually, very little about life is fun, interesting, engaging, or enlightening. It’s a miserable way to live–no matter how well it pays.

Living in a car doing what you are passionate about, by contrast, is  awesome. I get up every morning enthralled with the work we’re doing, and I have to force myself to turn off the computer and get some sleep. I’m not sure if you can just will a company into existence, but I believe what we’re building is something the world sorely needs, so we’re going to give it everything we’ve got. I’m not sure if it’s OK to recommend homelessness, but I recommend it.

And if anyone reading this happens to be an entrepreneur in the Valley, I’d love to meet as many of you as I can. So shoot me an email or follow me on Twitter, and we’ll see where this adventure takes us.

Can We All Agree “The News” is Sufficiently Broken?

I’ve had this blog post brewing in me for a long time. Years, to be precise. So despite the fact that it’s my finals week and I have an absurd amount of studying to do, I’m writing this stuff that not many people will read, because the situation has gotten out of hand.

Today, when CNN announced that a suspect in the case of the Boston Marathon bombing had been arrested, the world saw what happens all the time at news organizations but nobody really notices. That is, what was reported wasn’t even remotely true. No one was arrested. It’s simple, black and white, they were wrong.

This happens all. the. time. We’re not even talking about the bias of this company or the other or the fact that what really should be highlighted is often neglected; they were just wrong. It would be easy to wave a hand at this and be reminded that everybody makes mistakes, but the problem is much more fundamental and deep-rooted than a mistake some drunk intern made. The problem is that there was one individual who was making that decision.

I don’t care whether you’re the government of North Korea or a corporate executive; information changes the way people view the world and the way people act, and even if you’re the benevolent information dictator, no person or small group of people should have that much power when there’s another way to go about it.

The real question here, is what function does CNN serve? So far as I can tell, their main purpose is to find the best tweets and YouTube videos and distribute them to their absurdly large audience. If we’re honest, that’s all they really do anymore, is watch the AP feeds, find some great tweets, and have a pretty face share that with the world. With a few exceptions (i.e. Anderson Cooper), there is little dignity or true reporting going on.

To see why it came to be this way, you have to go back a few years to before the Internet was truly “a thing.” If you take yourself back 20 years ago, you had to be on the scene. You had to send a physical reporter with either a notepad or a cameraman to the scene to gather information and relay it back to us: Without these individuals there was no content. That’s difficult to imagine now, but when these sources were your only connection to the world that was a service you would gladly pay for. But now there are thousands of people on the scene with cameras and accounts, tweeting and posting and publishing immediately. As Clay Shirky points out, publishing is no longer an industry — it’s a button. We are all reporters. The greatest news of the 21st century will be recorded with grainy photos and videos and will not be written according to AP guidelines, but it will voices we’ve never been able to hear and content we’ve never had access to until now.

But this comes with its own challenges. The challenge of news today is the same as that of the Internet in 1998: There’s too much information. We have the Yahoo!s of the news who send editors or moderators through to pick out the best content and display it for all to see. That’s Buzzfeed, Gawker, the Associated Press and most news organizations, with varying degrees of success. But there is no Google. There is no one to tell us “according to the data that is provided and the way people interact with that data, here is the best content.” No one is truly telling us what is the best stuff, and no one is allowing all of us to fact-check the information collectively. We’re missing out on an enormous opportunity to see the world through the eyes of eyewitnesses and the people directly involved, and to be confident in that information, coming to ou own conclusions. What’s important in the news needs to be decided by the collective decisions of everyday people just like you and me, in the same way it is now created by the actions of everyday  people just like you and me.

It’s time for the democratization of news and information in a way that we can all make sense of.

Everything You Need

“Do not spoil what you have by desiring what you do not have. Remember that what you now have is among the things you only hoped for. Nothing is enough for the man to whom enough is too little.” – Epicurus

Here it is: the list of everything I need in life to be happy.

  • Somewhere to sleep
  • Something to wear
  • Something to eat
  • Someone to love
  • Art (music, literature, visual art, and something to make those with)
  • A computer with Internet connection
  • A soccer ball
  • The chance to travel and see something new

And that’s about it. Everything else is convenient but superfluous.

I’m just now fully realizing that if I let all of the unnecessary stuff fall away, I can live exactly how I’ve always wanted, and spend all day every day trying to change the world in a way I’m passionate about, instead of spending my life stressing to find a way to pay for things that won’t make me happy.

Here’s to more adventures.

Risk and Poverty

People tend to over-weigh risks on a personal level… It’s so easy to earn enough money just to live somewhere and eat food. Very easy to do. So I don’t know what they’re afraid of. Mostly afraid of failure, I think, but people should be less risk averse, when there’s not much at risk. – Elon Musk

Some people squirm when I say this, but I feel genuinely blessed to have lived in different states of what most people in the United States would deem “poverty.” I’m not sure whether I did so as a result of stupidity or a sense of adventurousness, but I’m grateful nonetheless.

There was the time in China when a crooked “landlord” stole my rent money at the same time as I was sued by one of the largest makers of language-learning software in the world. The software company (whom I can’t mention as a part of the settlement) agreed to settle for “how much do you have in your bank account?” (Note to self: don’t answer that question). I barely had enough money to buy rice. I had to hustle and do some quick freelance work from Craigslist to pull myself out. But I made it.

There was also the time when I was living in my car trying to get grasswire off the ground and the car broke down. I was desperate, broke, and felt very alone. I ended up scalping soccer tickets to pay for the car repair. But I made it.

But even if all those efforts failed, I would have found something else. There’s always a way. Even imagining the worst possible scenario, I would have wound up living in my parents’ basement. I could have sold my car and bought a greyhound ticket home. I could have stayed with a friend.

Granted, this is not the case for everybody. I don’t mean to imply that *anyone* can avoid poverty if they would just work at it. But for me, personally, because of all the things I’ve been blessed with and all of the opportunities I’ve been given, I can afford to take risks that many others couldn’t. And, to a certain extent, it feels like my duty to take those risks if I believe they have a chance of bettering the world, because I have an awful cushy place to land if I fall.

Now that I have a family this changes, but not that much. It changes because as hard as it would be to tell my parents that I failed and needed to move into their basement, it would be harder to tell my wife. Luckily I married the type of person who would help me pick myself up and figure it out.

And the thing that no one who is in poverty will tell you, is that although the living conditions aren’t ideal, it’s really not that bad. Especially if it’s temporary, you have marketable skills, and someone to rely on. Not all people have that; you should be grateful if you do.

The “worst-case scenario” most of us really fear isn’t that we’ll not be able to eat or not have a place to stay. It’s that we’ll have to admit failure.

Sometimes, failure and poverty is the best place to start. That’s why Jan Koum, the founder of WhatsApp, which sold to Facebook for $19 Billion yesterday, made sure to sign the acquisition papers on the door of his old welfare office.

It’s OK to fail. But if you truly believe in something, it’s not OK to not try.


Media Responsibility During Tragedies

I’ve had a rather unique opportunity over the past few months; as Garrett and I have been building and testing GrassWire, we haven’t been required to operate according to traditional journalistic rules and ethics. We are breaking ground and exposing news in a new way (or at least we hope to be), and as such, the journalism world is our playground.

And as I watch and read the coverage of the shootings in Colorado and Connecticut, I have to say: I think we’re doing it all wrong.

The Streaker Rule

It’s standard in sporting events that should an unauthorized individual enter the field of play, cameras should look away. Commonly called “the streaker rule,” this rule applies to those that are clothed as well. The purpose of doing so is to not draw attention to the individual at fault. Naturally, if every streaker had a few minutes of airtime on national TV, the number of people streaking would increase.

Of course we are curious. Everyone wants to know what is happening, whether they think that streaking is funny or they see it as a serious distraction. But the cameras are responsible enough to divert their attention so as to not provoke more incidents.

Why, then, when an armed individual enters a school and massacres children, do we profile the suspect as intensely as we can? With this most recent example, multiple reputable news sources even found the Facebook profile of the wrong person, instantly plastering it all over the news and social media channels. Later, full hour-long episodes will be dedicated to the shooter, just as they have in the past.

For Columbine, it took a few people that were absolutely diabolical. Now all it takes is someone willing to sacrifice their lives and the lives of others for a little notoriety. That’s dangerous.

We are all morbidly fascinated. What would drive a person to enter a school full of children and begin murdering them is beyond our comprehension and boggles our minds a little bit. But should there not be a “streaker rule” for a tragedy like this? Wouldn’t it be better for all of us, in the long run, to turn the proverbial cameras away?

Sandy Hill Coverage

A lot of unethical things were done during this coverage for the sake of ratings and page views: 6-year-old children were harassed by reporters immediately following the shooting, essentially trying to get them to break down for the rest of the world to see. Somehow a reporter got the phone number of a woman who lost both a child and a grandchild in the shooting, and remarked that when they called to question her she became “silent” and “despondent.” Of course she was!

You would never approach a family member at a funeral and interrogate them as to how they’re feeling. Of course we want to sympathize. We want to understand a tiny portion of what it must feel like to be in the shoes of those people. But doing so needn’t require us to harrow up the most painful of memories from those that badly need to grieve.

There are times when those involved want to tell their story; for some this comes quicker than for others. Give them the option to come forward, give them an outlet through which they can share their thoughts and feelings with us, but don’t prod them.


Those in the journalism industry understand that they will often be asked to make a decision between ethics and profit. The line between tabloid and respected publication seems to be wearing thin. But especially in cases like these, in which so much is at stake, we need to take the high road. As the national media and journalistic institutions of this country, we can do better.


Why Successful Entrepreneurs Are Usually Liars

I made a rather bold statement on Twitter today: “I’m convinced 90% of startup success comes down to market research.” I’ve also said, “I feel like most of the time when an entrepreneur is telling you about what made him successful, he’s lying a little bit.”

I really meant it.

I think a lot of startups get deceived when they hear success stories. Take the startup I helped found when I was 18, Stubtopia, for example. This is how the story goes:

I was an eBay junkie, so when my family wanted to go to an event in New York I looked at tickets on eBay. They were expensive, I was intrigued, and I decided to come back to it later. A little while later, my brother emptied out his life savings, we bought some tickets, doubled the money really quick, put the savings back, and kept making a bunch of money. Later we moved it off eBay, turned it into a real business, and it’s still around today making millions.

It wasn’t exactly a secret that Stubtopia did pretty well; my brother won the Utah Student 25 (a student entrepreneur of the year award) while I was on an LDS mission in Ukraine, and in doing so Stubtopia’s revenue numbers were exposed.

It was really interesting to watch what happened in the entrepreneurial ecosystem after that. It was publicized that some college kids made good money, and other people started doing the same thing. A couple of friends went out, bought thousands of dollars worth of tickets to try to resell, and lost it all. They probably determined we were lucky, cut their losses, and moved on.

But something was different; something was missing. I bolded it above.

Almost all entrepreneurs intentionally leave out the secret sauce. It’s usually something that anyone could replicate if they were told, but it takes a long, long time to figure out.

Even before we started selling tickets, I was selling silicone wristbands on eBay, not unlike the LiveStrong wristbands which received an absurd amount of popularity. It was an extremely flooded market; there were thousands on eBay at any given time, but I would regularly make $6-7/wristband while everyone else on eBay fought for pennies. The secret sauce? I used the word bracelet. Personally, if I were looking for a silicone wristband, I would never, ever use the word “bracelet” to describe it, but apparently some people do. Their selection was so limited that they would pay 600% of what other eBay users would pay.

When we started selling tickets, I watched the eBay auctions for about a month. I kept detailed information (some on spreadsheets, some in my head) about what seats sold for what, which seats didn’t sell, which cities sold well, which didn’t, etc. By the time we bought tickets, we knew exactly what we were buying. We knew the dates, venue, times, keywords, and even what times we would list on eBay to receive maximum exposure. That was part of our secret sauce. We didn’t flippantly buy tickets, and if we had, we would have failed.

When we moved it off eBay and onto the real-life Internet, I was really nervous. We didn’t have an already-available market we were selling to. So what did I do?

I sat down for about a month. I probably did thousands of Google searches, private messaged hundreds of people in forums, joined IRC channels, and spent 40 hours per week for about a month just researching. I cold called would-be competitors, I made a few friends (whom I still talk to today), I talked to a few drunk people at some trade shows, and we figured out exactly what we needed to do to market our tickets. We developed some marketing channels that probably still account for over 90% of Stubtopia’s sales. If we hadn’t had that (which a lot of future copycats didn’t), we would have failed. We had to have about 100 things exactly right for it to work, including a bunch of things that other members of the founding team figured out when I had messed up. But doing so made us a lot of money.

And now, as I work on a new project, I’ve spent a month and a half head-down trying to figure stuff out. I know this goes against the “get out of the building” mantra that many entrepreneurial leaders talk about, but I “get out of the building” online. There’s usually not a lot of information online about what I’m trying to find; I often have to try about a dozen different search queries, search a few different forums, and talk to a couple people in order to get an answer. But we’re really close to it again; we’ve almost got the secret sauce. And once you’ve got the secret sauce, you’ve got a magic box where you put $1 in and $10 comes out. And then you never tell anyone what that secret sauce is, you tell them everything peripheral. Other entrepreneurs who think, “Oh, I could do that too” will probably fail. Not because they’re not as good at executing as you, but because they don’t have the secret sauce.

You have to become an absolute expert in what you’re trying to do, enough that you will be able to make money and do so at scale, and that requires an absurd amount of what I’ll call “market research.” You can’t just arbitrarily throw stuff against the wall and hope it sticks; if you’re doing that, you might as well play the lottery. If I had my way of saying it, this is how I would rephrase the whole “nail it then scale it” or “customer development” mantra: become an absolute expert. Know everything. Make it so that when you show up at trade shows people think you’ve been in the industry for years. Innovate in ways that seem completely natural to you but seem absolutely foreign to everyone who has been in the industry for 15 years.

And when you talk at entrepreneurship events about how to be successful, give vague answers like “work hard” and “learn fast” and “hire well,” but never, ever reveal the secret sauce.

Why “The News Media” is Fundamentally Broken

One of my favorite tech writers, Hamish Mckenzie, wrote a piece today about Elon Musk fighting the media, and how Musk is right to do so. As a part of that article, he explained, with precision that I never could, what is wrong  “the media” and “news” as a whole.

There is no established rubric for peer review in the media; adherence to truth is largely a matter of self-regulation. Instead of peer review, in which experts check the work of other experts, media has editors and fact-checkers. Often, those people are not experts in the matters their institutions are covering. Worse, sometimes they are novices on subjects ranging from climate science to jet propulsion to even basic statistics.

But they still get to control the headlines on those stories. They still serve as the major conduit through which the public is informed about what are often intrinsically complex but extremely important matters. And even with strong editing standards in place, it is inevitable that some of the reporting for which they are responsible will lack crucial nuance or just be plain wrong.

I remember a particular article I was interviewed for over the summer. I spoke at length with a reporter about grasswire, an effort we’re building to effectively crowdsource every aspect of breaking news, from production (which is already outsourced to people with camera phones) to curation and fact-checking. The reporter grilled me about the possibility of everyday people fact-checking as well as someone who graduated with a degree in journalism. Someone who did this for a living and had really become a professional at telling stories and getting the facts right was needed, he argued. Would it really be possible for everyday people to do the same thing accurately?

When I read the article I had to laugh when he mentioned I wore “a red T-Shirt and red pants.” My pants were definitely brown.

As we took further interviews about grasswire and my living in my car to get it off the ground this summer, I noticed how difficult it was for me to convey what was happening to reporters. They would ask simple, direct questions, with answers that were very complex and nuanced. At times I could feel the reporter wanted me to skew an answer one way so that it would better fit their narrative. Other times I could tell a reporter was new enough to a topic area that they simply couldn’t understand what I was saying.

Even after fact-checking a couple of times I had to email people about the finished pieces and say, “I can see how you got that from our interview, but this piece is technically incorrect. You need to change it to say X.” It wasn’t the reporter’s fault: What they do is hard. The fundamental problem is that “the media” relies on outsiders to tell a story. There’s no way, for example, you can take a day, a week, or even a month to jump into my religion and fully understand it. It’s very complex with many, many moving parts.

The same is true of events. Creating a story by asking some people questions and trying to bind their responses into a single narrative with one story that makes sense is often-times impossible. Not because the reporter is doing a bad job, but because their task is impossible. The war in Syria is often shown as two warring factions, when in reality there are dozens of groups who play off each other and fight against each other at different times. Even the armies themselves are trying to piece together who is fighting for and against whom today; to expect a reporter to do so is absurd. But that’s exactly what we do.

How, then, can we have any hope of gaining a definitive understanding in the world, if even people paid to do so full-time have difficulty grasping it? Maybe there isn’t any. Life isn’t simple, people aren’t just good or evil, and situations are never binary. Maybe we’re not ever supposed to look at what’s happening in the world and say, “I understand now; it’s simple.” Because it’s not. If we think that we’re probably missing a lot of pieces of the story.

Google+ Comments Turn YouTube into a Spam Platform

The Google+/YouTube integration has receive a lot of criticism, but most critics are ignoring the most important piece: The spam.

I understand that spammers will always try to exploit every system, but the Google+ comments on YouTube make it far, far too easy.

A couple of important changes took place in conjunction with the new commenting system:

  1. External links are allowed
  2. The comment with the most “activity” (read:replies) goes to the top

It’s fairly obvious how you could spam that: Post a comment with a link to whatever you’re trying to promote, and get a bunch of accounts to reply to it. Child’s play. But it goes even easier than that.

It appears you can actually reply to your own comment, There doesn’t appear to be any rate limit for how often you can comment, and the comments don’t even have to be different; they can just be a random string repeated 1000 times.

So I can write a comment with a link, then run a script (or even a macro) that will reply to that comment, and in a few minutes I will be the top comment on any video on YouTube.

If you have a popular YouTube channel, it might be advisable to turn your comments off immediately. And Google – it’s time to start fixing one of the most broken things I’ve ever seen you do.