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Latent serendipity

When I was a kid I liked to dress up in the stories of successful people.

I read about how Bill Gates used to rock in his chair when he was thinking, and for a few months after that I made sure to rock back and forth whenever I was programming. I read a book about Stephen Hawking that described how Oxford graduate students would buy huge sketchbooks to scribble physics formulas in, and so I went out and bought a huge sketchbook to carry around with me.

We all do this. We read little snippets of people’s lives in long magazine exposés, or see adaptations of their adventures in 2-hour summer biopics, and we take their personality traits and try them on like a pair of new shoes. Then we look at ourselves in the mirror of our minds and ask: “Does this fit? Do I do that too?”

When it’s something like rocking back and forth in our chair we can usually fudge it and say, “Yeah, I do that.” Sometimes we really do end up doing those things for a couple of weeks. Something in our brains tells us if we’re similar to these people we’ll be more likely to share in their success.

But sometimes, trying on these stories doesn’t work at all. There’s a special class of stories that make our minds come up blank.

You hear a singer say, “Well, my parents always played Aretha Franklin at home so she was a big influence for me.” Or an entrepreneur say, “Well, I noticed early on that customer service was the biggest part of running a successful business, and so that’s why our vision is to help companies do better support.”

It’s like successful people have these little insightful anecdotes that they can use to explain their lives. Things like, “This has always been important to me.” Or, “I noticed this from a young age.” Or, “I’ve always been really interested in this.” These anecdotes, these calcified bits of personal history, carry a certain kind of inevitability about them. Like they were always important, and clearly pre-destined to have a huge impact on the life of the person telling them.

When we hear these things, we think to ourselves, “What did I notice early on that I can use to start my business?” or “What did my parents do that’s going to influence my future success?”

Usually, we don’t have an answer. Our brains say, “Your parents never listened to Aretha Franklin.” Or, “You never noticed that customer service was important when you were a kid.” There’s nothing obvious about our daily lives that will inevitably lead to our future success.

Why is is this? Why do we feel like we don’t have this special kind of story to tell? Why can’t we talk about these obvious parts of our lives that will inevitably lead to our success?

And, if we don’t have them, how did these successful people get them? Is it causational? Are they successful because they’ve always known what was “unique” about their experiences that they could apply to their lives? Or is something else going on?

A step into story telling
To answer these questions the first thing we have to do is think hard about how stories work. A good way to do this to look at how some of the most popular stories are constructed: Hollywood movies.

Hollywood movies are split up into three acts: in act one the hero is confronted by a problem, in act two the hero is almost (but not quite!) destroyed by this problem, in act three the hero conquers the problem in an act of unlikely redemption. This forms what we call a narrative arc: it’s a story that is told in such a way that it builds tension and emotional attachment, gets us onto the edge of our chairs, and then resolves the tension nicely and neatly at the end for everyone to live happily ever after.

As Kurt Vonnegut said, “Somebody gets into trouble, then gets out of it again. People love that story. They never get tired of it.”

In all of these stories, there is also generally something special or unique about the character that happens in the beginning that becomes helpful to them later on in overcoming the adversity they will eventually face.

What’s interesting is that if you look at how we write stories about entrepreneurs, or singers, or writers, they’re generally written in the same way as a Hollywood movie.

We like to talk about their lives in a nice neat narrative style. The character usually faces a problem: “I was rejected by 25 different publishers before one took a chance on me.” And the stories are scattered with these same anecdotes that we’ve been talking about: events at the beginning that foreshadow their later success. “I was a big fan of Star Wars growing up, so that’s why I decided to set my novel in space.”

The problem with telling stories in this way, however, is that if you actually followed someone around who was in the process of becoming successful, their lives would look very different from what we might imagine from watching a Hollywood movie or reading a story about them.

A peek behind the curtain
The first time this was really driven home for me, I was reading an article about my friend Noah Ready-Campbell. After college and a stint at Google, Noah started über-successful women’s second-hand clothing startup Twice. Founded in 2012, they’ve grown extremely quickly and recently raised an $18.5 million Series B led by Andreessen Horrowitz.

The article was in the Wall Street Journal and it was basically a question-and-answer format interview between Noah and the journalist. One of the first questions she asked him was:

“What do you know about the market for women’s secondhand clothing?”

It’s a pretty obvious question to ask – especially to a guy who co-founded a fashion startup that focuses on women. Noah replied:

“I went to boarding school in New Hampshire for high school and I was on financial aid, but I had to wear nice clothes every day. I used to go to the Salvation Army. I remember one day buying a Brooks Brothers shirt. Still had tags on it. It was a $200 shirt, and I got it for $10.

I remember thinking it was an incredible deal. That experience growing up gave me a little bit more insight on [secondhand fashion] than probably your typical entrepreneur in Silicon Valley.”

What I found interesting reading that quote is that it contained exactly this kind of story that we’ve talked about being part of every success story – the kind of special characteristic or experience that the character has at the beginning that foreshadows their later success – but I could read it in two different ways:

  1. As someone who’s known Noah in some capacity since before he started Twice
  2. And as my younger self, reading a story about an entrepreneur I admire

Reading the story as my younger self I would have pictured it in the same way as it would be portrayed in a movie: Noah growing up with this big enduring insight about the price of second-hand clothing firmly fixed in his mind, and who pretty much always knew he was inevitably going to found a company like Twice.

But knowing Noah, I know that Twice is far from the first thing he’s worked on. I know that he’s had many insights throughout his life, and that most of them had nothing to do with second-hand clothing. I also know that the vast majority of his experiences (obviously) didn’t make it into this interview.

Looking at his story from both angles it seems clear there are lots of things that this Hollywood-style of story telling leaves out about our lives and experiences. Interestingly, this is an issue that people have been struggling with for a long time.

Modernism, Woolf, and Nassim Taleb
Around the beginning of the 20th century a movement of writers – the modernists – began to realize exactly the issues with traditional narrative form, and began to question whether this was actually the best way to tell stories.

At the time, novels followed the same kind of neat story arc as the Hollywood movies of today. But the modernists realized that life doesn’t really feel like a Hollywood movie as we’re living it. They thought that authors were just writing novels in the traditional format out of habit – not because it truly reflected the experience of living.

Virginia Woolf, one of the most well known of the modernists wrote:

“The writer seems constrained, not by his own free will but by some powerful and unscrupulous tyrant who has him in thrall, to provide a plot, to provide comedy, tragedy, love interest…The tyrant is obeyed; the novel is done to a turn. But sometimes, more and more often as time goes by, we suspect a momentary doubt, a spasm of rebellion, as the pages fill themselves in the customary way. Is life like this? Look within and life, it seems, is very far from being ‘like this.’”

Woolf argued that life doesn’t follow a regular narrative structure. That’s too convenient, too clean, too easy to digest. Instead, she wrote:

“Life is not a series of gig lamps symmetrically arranged; life is a luminous halo, a semi-transparent envelope surrounding us from the beginning of consciousness to the end.”

Instead of dressing it up with idealized narrative and pre-defined plot structure the modernists created a form of literature that attempted to deal more closely with human existence as we actually experience it.

One of Woolf’s most famous works is a book called Mrs. Dalloway. The plot – if you can call it that – follows an eponymous London socialite from morning to evening of a single day as she gets ready to host a party.

No details are left out. For example, we watch her walk to a flower shop to buy an arrangement for the party, and listen to the things that pop in to her head as she walks. It’s essentially just a collection of moments written as they happen, and it’s actually one of the earliest examples of a novel written in “stream of consciousness” form.

What’s the difference between Woolf’s stream-of-consciousness style and Hollywood movies? A Hollywood movie is written in retrospect. It’s stripped of unimportant moments – every scene has a “reason” for being included, every moment pushes the story forward or foreshadows what’s to come.

By contrast, Mrs. Dalloway is full of “unimportant” details – just like life is. Woolf doesn’t care what’s going to be important to the story later. She just talks about everything that happens, as it happens.

When we talk about success, we tend to talk about it in a Hollywood style – leaving out everything that seems unimportant. When Noah talked about that moment in the thrift shop, he didn’t walk us through a minute-by-minute account of his high school expeirence. Instead, he gave us a one second clip of his early life that related to the company he later when on to found.

This makes a lot of sense when you think about it. It would be terribly inefficient for an entrepreneur to tell a reporter about everything that ever happened to her in high school in order to explain how she gained the one insight that helped her found her startup. And it would also be terribly inefficient for her to remember much less be able to talk about it all. Author, financier and philosopher Nassim Taleb tells us:

“Events present themselves to us in a distorted way. Consider the nature of information: of the millions, maybe even trillions, of small facts that prevail before an event occurs, only a few will turn out to be relevant later to your understanding of what happened. Because your memory is limited and filtered, you will be inclined to remember those data that subsequently match the facts.”

And importantly, this distortion results in a particular kind of survivorship bias: everything that seems irrelevant to the story becomes totally invisible, completely left out. It’s hard for the person who experienced those things to remember them. And the person reading their story assumes that the irrelevant facts don’t exist.

This seems like it answers most of our questions. When we tell stories about success and we leave things out that are irrelevant, we make everything look much neater, more story-like and more inevitable than they would otherwise. This accounts for much of the differences that we’ve been discussing between “success-as-it-is-experienced” and “success-as-it-is-talked-about-later.”

But does this really solve everything? Is all of this just a combination survivor bias and hindsight bias rolled together?

I don’t think it does because it doesn’t deal specifically with how pieces of our lives become important. It still assumes that importance is static – that the significance of everything that happens in our lives is always clear. As though the first time our singer listened to Aretha Franklin she could immediately list her as the key to her future success.

Clearly, there’s still something else to be addressed here.

Retrospective coronations
In his book on evolution, Darwin’s Dangerous Idea, the philosopher Daniel Dennett writes that there are certain events in nature that have a unique attribute:

“You can’t tell that [the event] is occurring at the time it occurs! You can only tell much later that it has occurred, retrospectively crowning an event when you discover that its sequels have a certain property.”

An example of this kind of retrospective coronation, Dennett says, can be found by thinking about the woman who scientists call Mitochondrial Eve – so named because her mitochondria (the energy sources for the cell which are passed down from mother to child) are present in every human being currently in existence.

Paraphrasing Dennett, let’s think a talk more about Mitochondrial Eve by thinking how she got her title:

Consider the set of all human beings currently alive. Each person alive today was born of one mother. Each of those mothers has one mother – the grandmothers. Each of those grandmothers have mothers and so on.

The sets get smaller each and every generation until they contract down to one person: Mitochondrial Eve, the “woman who is the closest direct female ancestor of everyone alive on earth today.”

Dennett asks, how does a person go about becoming Mitochondrial Eve? Was there something special about her? If we had a time machine and could go back to visit her, would we be able to tell that she was going to be the most recent mother of every human alive today?

According to Dennett the answer is no. And it has nothing to do with our ability to gather information. It’s not a question of better microscopes, or more careful observation. “It is important to remind ourselves that in all other regards, there was probably nothing remarkable or special about Mitochondrial Eve,” he writes.

Why do we know there was nothing special about her? Because her current status is a complete historical accident! If things had gone differently at some point in human history, the current Mitochondrial Eve would have had absolutely no historical relevance.

For example, consider a scenario in which tomorrow a plague spread after which only 1% of the population survived. “[The survivor's] closest common direct female ancestor…would be some woman who lived hundreds or thousands of generations later than [the current Mitochondrial Eve], and the crown of Mitochondrial Eve would pass to her, retroactively…This historically pivotal role is determined not just by the accidents of [Mitochondrial Eve's] own time, but by the accidents of later times as well. Talk about massive contingency!”

Consider another example (also from Dennett): Imagine a doctor coming home from the office and telling his wife, “Guess what I did today! I assisted at the birth of Victor Hugo!”

There’s something clearly absurd about that. Obviously, the birth of Victor Hugo was not significant at the time it happened. It only became significant much later.

Connecting the dots backwards
So let’s think about how this ties back in to what we’ve been talking about. We know from the modernists and from Taleb that we enforce a story-like structure on to events to make them easy to digest and that, in order to so, we leave out everything that seems “unimportant.” And we know from Dennett that there are events that have a special property: we can’t know they’re important until much after they have occurred.

How can we relate that back to these little insightful anecdotes that successful people share, like hearing a singer say, “Well, my parents always played Aretha Franklin at home so she was a big influence for me,” or an entrepreneur say, “Well, I noticed early on that customer service was the biggest part of running a successful business, and so that’s why our vision is to help companies do better support.”

Maybe the answer is that, like the case of Mitochondrial Eve, there are certain events that happen in our lives that we can’t tell are important until many months or years after they have occurred. And in just the same way that we can’t tell that a particular woman will be Mitochondrial Eve by examining her more closely, we also can’t tell which events carry this special property by paying closer attention – the importance is latent and invisible. What makes them important is their serendipitous connection to what comes later – they are only retrospectively crowned.

You can think about it like this:

Try to imagine every event that happens in your life as a bead. Depending on what kind of event it is the bead gets a different color. As each event occurs you get a new bead, and you throw each bead into a pile of all of the other beads representing all of the things that have happened in your life.

What do you get after living for a few years? A vast pile of beads. Very little structure, very little coherence. Beads of every different color piled together. It might be hard to pick out anything special about your pile by just looking at it.

But now imagine that at some point in your life you get a special kind of bead. This bead marks an important event: you become the first person in your family to graduate from college, you get a big promotion, your novel becomes a bestseller, or your business takes off. Let’s imagine that this special bead is black.

When you get this special bead, something interesting happens: people become obsessed with your origins. They ask, “How did you do it? What was it about your early life that helped you to get this bead?”

In order to explain yourself, you go back through your pile of old beads looking for ones that match it.

And when you look through your vast collection of beads, suddenly the black beads begin to stand out. The black ones didn’t seem special at all before, but now you begin to notice them. It’s sort of like when you first buy a car and you suddenly start to notice all of the other people on the road that have that have the same one – they were there the whole time, you just didn’t notice it.

Sometimes you even notice that blue beads can become black if you look at them right. So you slide the blue beads on to your string with the rest of your black beads, and position them in such a way that they appear black when you look at the string in the light.

When we ask people to tell their stories, we’re really asking for this string of beads.

But what we don’t see when we look at someone’s string is that these beads – the visible beads – aren’t everything. That far from having beads of just one color, the black beads that we see are just a tiny collection pulled from a mountainous pile of beads – the totality of which represents the vast constellation of memories and experiences they’ve had throughout their life.

What we don’t see is the fact that although the first bead on the string is from many, many years ago, at the time they got it they might not have put the bead on a string. It was, very likely, just one bead among thousands of others. Totally mundane. What we don’t see when we look at the string is that it was only much later that the bead became important enough to be picked out of the pile.

Latent serendipity
So what do we do with all of this? What’s the use of seeing the stories we tell about our lives in this way? Is this a pessimistic way of looking at life?

Let’s get back to Noah’s story about noticing the value of used clothing in high school. What’s really interesting is that if you asked Noah today what the big insight from his high school days was, he might tell you that story. And he would be absolutely right – it clearly holds vast relevance to his day-to-day life as a CEO.

But if you had asked Noah while he was at Penn which of his memories from high school would turn out to be most relevant to his future career as an entrepreneur I’m almost 100% certain he wouldn’t have talked about that particular memory.

Clearly that moment changed enormously in significance from the time he was in college to now. What started out as an every-day observation filed away along with millions of others inside of Noah’s collection of beads became something much bigger.

For young entrepreneurs this is a frustrating realization. As young, ambitious people we’re constantly looking for a moment of insight like that. We get these ideas, and we stay up late at night obsessing about them, planning for what the world will look like after we bring them to reality.

But we often aren’t very good at applying this knowledge that the ideas and insights that end up becoming significant often don’t look that way at the time they occur.

This is an important lesson for me, because it applies directly to my story. In December of 2012 while I was still a sophomore in college my dad called me to tell me that he had an idea for a product.

“When I’m on the phone with someone it’s very difficult to explain to them where to go on a website,” he said. To fix this, he wanted to have a grid – kind of like an Excel spreadsheet – expand down from each person’s screen. Then you could tell your friend on the phone, “Look at cell E5,” and you would always be talking about the same thing. He wanted to call it GraphNet.

At the time I think I said something along the lines of, “That’s interesting Dad, but it would be really hard to make it work well on different computers and different browsers. It would probably have to be a browser plugin. I don’t think people would use it.”

I told the idea to my co-founders who built the first version at a hackathon a few weeks later.

2.5 years after that we had built the company that came out of that phone conversation to the mid six figures in revenue with just 2 full time co-founders, a few part time employees and $20,000 in funding. Two months ago, I flew from my college graduation ceremony to finish negotiating the sale of the company to Pega.

Like all young entrepreneurs, I’ve had plenty of moments where I came across an idea and thought: “This is it! I’ve found it. This is going to be huge.” And none of those turned in to anything meaningful. But this small, insignificant-at-the-time little conversation somehow became something very important to my life’s story.

So the first lesson is not to despair at reading these stories. They are excellent inspirational material, but poor instructional manuals. The second is, even though we see it in movies and read about it in magazines it’s not necessary to imbue forced significance on to any particular event or idea as it happens – many successful people didn’t recognize the importance of their experiences until many years after they occurred.

And the third lesson is the most important: whether we recognize it or not the potential for something extraordinary lies in pretty much every moment of our lives, large or small.

It means that each moment carries a kind of latent serendipity – a hidden ability to become something special down the road – if the right combination of events occur to unlock it. It means that the apparent character of a particular moment doesn’t matter. Because ultimately the difference between an important moment and a million others is not how significant it seems when it occurs. The difference is that an important moment happens to produce a spark that doesn’t go out.

And the beauty of it is this: the not-knowing what our story will be requires faith that eventually the beads of our lives will be connected on a string. And it encourages a sense of wonder as we look at every moment – because every moment could be one that becomes woven into the fabric of our life’s story.

As someone flawed, weathered, and wise once said, “You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something – your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well worn path; and that will make all the difference.”


Thanks to Mark Bao, Jesse Beyroutey, Ajay Mehta, Wesley Zhao, Alex Rattray, Quentin Farmer and Paul Singman for reading drafts of this.

29 Sep 2014, 9:39pm | 9 comments

What I learned bootstrapping a 6-figure business from school

When I got to college three years ago I set two goals for myself. By the time I graduated I wanted to:

  1. Be well read
  2. Learn how to build a real software business

By real business I meant a business that has paying customers from day one and that makes enough money every month that I could work on it full time when I graduated.

Although I wouldn’t go as far as to call myself well-read (I don’t think that’s something to be achieved, just pursued) I can confidently cross goal number two off of my list:

In about 11 months we’ve built Firefly up to well into the 6 figures in recurring revenue.

We’ve done this primarily through two channels: on-site website signups and large partnerships.

In July we announced a partnership with Olark to roll our cobrowsing out to their 5,000 paying customers. We’ve also struck similar deals with much larger customer support companies as well as companies in other verticals like financial services.

What makes this somewhat special is that there’s just two of us working on the business, we’re entirely bootstrapped (except for 20k from the excellent Dorm Room Fund), and this year I’m going to be a senior in college.

Because the past few years have been such a crazy ride, I wanted to take some time to write down some of the things I’ve learned along the way. Continue Reading

11 Sep 2013, 4:15pm | 59 comments

You’re selling it wrong

The other day I had coffee with two friends, we’ll call them Peter and Alex.

Peter is working on a new startup, and Alex runs a large organization. Here’s how Peter pitched what he’s working on:

Peter: So basically I’m working on a startup called W. It does X, Y and Z for large organizations. It’s especially great if you need to organize and respond to lots of support emails.

Alex: Wow, that sounds awesome. We definitely need to respond to lots of support emails for Organization X.

Peter: Yeah, it should be perfect for you guys. Would you pay for it?

Alex: Hmmm, I’m not sure. I’d really have to think about that. I think I’d have to see the product before I could say.

Here Alex is pulling away. Peter senses this and pushes further.

Peter: It could really save you a ton of time though. Think of all the hours you spend answering support emails.

Alex: Yeah, yeah definitely. It’s just I think I have to see the product itself first.

Awkward silence.

Ok, let’s stop and rewind. Where did this pitch go wrong?

The first thing to note, is that Peter is doing the right thing by asking for money.

If you’re in Peter’s position, the only way you’re really going to be able to tell if someone is going to buy your product is if they actually give you their credit card number.

But the thing to be aware of when you’re pitching your startup is that you’re not asking for an early customer’s credit card because you want their money – not really. You’re asking for for their money because it’s an excellent way to elicit useful information: people aren’t polite when money is at stake.

The problem is that when some founders ask for money, instead of using it as a tool to gather feedback, they end up steamrolling the person on the other end. They unintentionally smother the signals that are being given off in the conversation because it feels like the goal is to get the credit card.

To be clear, the goal is not to get a credit card: it’s to get information.

The first sign of trouble was right after Peter asked Alex if he would pay for his product. His response was, “I think I’d have to see the product before I could say.” With a response like that, it’s clear that Alex is pushing off a purchasing decision.

Peter sensed this, but he was in Sell Mode so he pushed further about the potential benefits of his product: “Think of all the hours you spend answering support emails.”

Now Alex feels trapped and antagonized. So instead of doing what Peter wants and agreeing to buy, he just politely pushed him off again by saying, “It’s just I think I have to see the product itself first.”

And after that second attempt the conversation was basically over. Peter learned nothing except that Alex didn’t want to buy his product that day.

But that’s not really useful information is it? What Peter needs to find out is: why didn’t Alex want to buy?

Here’s what should have happened:

Peter: So basically I’m working on a startup called W. It does X, Y and Z for large organizations. It’s especially great if you need to organize and respond to lots of support emails.

Alex: Wow, that sounds awesome. We definitely need to respond to lots of support emails for Organization X.

Peter: Yeah, it should be perfect for you guys. Would you pay for it?

Alex: Hmmm, I’m not sure. I’d really have to think about that. I think I’d have to see the product before I could say.

Here Peter encounters the same resistance as before, but instead of steamrolling over it he decides to find out where it’s coming from. The first thing to check is whether Alex can actually make a buying decision for his organization.

Peter: Gotcha, no problem. So if you were going to buy software like this, what would the process be like?

Alex: Well basically I’d take it to my team and we would discuss it. Fred is in charge of the support side of things so it would really depend on how useful he thinks it is.

Bingo. Now Peter knows that Alex was resisting because he couldn’t even buy the software if he wanted to. Now Peter should find out if there are any other reasons why Alex didn’t want to commit, and also how much his organization might be willing to spend.

Peter: Oh that makes perfect sense. Do you guys use any software that does this already?

Alex: Yeah, we actually bought Zendesk for everyone in the office. It’s about $24 bucks a month per person.

Now Peter knows that he can at least charge $24 bucks a seat. Now he needs to find out more about how they use Zendesk.

Peter: Interesting, how do you use Zendesk right now?

Alex: Glad you asked! I love Zendesk, but there are also some things I wished it had…

Do you see how easy it was to take an antagonistic pitch that lasted 4 minutes, resulted in zero sales, and generated no useful information and turn it in to a long, meaningful, and constructive conversation where both parties are engaged and interested?

Be prepared to listen when people give off subtle signals. Read between the lines. Ask for money because it’s the best way to get useful information, not because you want money.

Always try to listen more than you talk.

17 Aug 2013, 12:02am | 8 comments

Public speaking for introverts

A few days before I have to talk in front a lot of people I get this queasy feeling in my stomach that won’t go away.

I don’t want to eat. I just want to cancel the talk because I don’t want to deal with the stress.

My hands get sweaty before I get on stage. I feel like I want to run away. I consider asking someone else to get up there instead of me.

And then I walk out there, do what I have to do, and everything works out fine. I’m usually even pretty exhilarated by the time I get done. Continue Reading

12 Aug 2013, 3:39am | 27 comments

How to get your first 10 customers

Preface: the assumption for this essay is that you’re building a B2B app, and you have something built but you’re having trouble getting people to pay for it

There are three problems with getting your first few customers:

  1. You (probably) don’t know how to sell things
  2. You don’t know who you’re selling to
  3. You don’t even really know what you’re selling

Nobody tells you how to answers these questions, and so most people go out to get initial traction in a haphazard way:

  1. They have a vague idea in mind for who wants their product
  2. They’ve already built the product, so they put together a landing page which which, like, totally speaks to the core value proposition
  3. They write some combination of any of the following:
    A few half-baked ads
    A few forum posts
    A few comments on relevant blogs
    A few blog posts
    A few cold emails to journalists (because, dude, we would BLOW UP if we could just get ‘Crunched)
  4. They send these out into the wild, and (no surprise!), get very few responses
  5. They conclude that the product must suck and that nobody wants it, because Mark Zuckerberg did exactly the same thing to launch Facebook at Harvard and look at how that worked out for him

If you try to get initial traction this way, it’s very difficult to untangle why it didn’t work:

Were the ads targeted to the wrong keyword?
Was the copy not compelling enough?
Was the sample size too small?
Or does no one want what I’m selling?

When they fail to get initial traction, most people conclude that the product is the problem. That no one wants what they’re selling.

They never consider that the way they’re selling might be COMPLETELY wrong (either in the way the product is being pitched, who it’s being pitched to, or some combination of the two.)

I think most of us have been lulled into this sense that the second you post your new product to a listserve you should automatically get sucked into a 4 minute montage scene featuring dark ominous 9 Inch Nails background music only to be spat out at the end with enough money to buy that estate on the Amalfi Coast.

And when that doesn’t happen, our first response is always to blame the product.

Formally this is called the actor observer bias which tells us that we tend to blame things that don’t go right in our lives to circumstances beyond our control:

“No one responded to my emails, so the product must suck. Nobody wants it, otherwise it would already be on TechCrunch.”

This is wrong. Here’s the truth:

You have learned nothing from spending $200 on Adwords, or writing a few comments, or sending cold emails to journalists.

Let me repeat: You have learned nothing. You get a big Zero. You have no actionable information.

Your product could suck. But it could still also be completely your fault. Or it could be completely random that you didn’t get any responses. Maybe the journalists were having a bad day, or the three people who clicked on your ads were just bots.

The point is: buying a few ads, or sending a few emails, or writing a few blog posts is not enough to conclude anything.

Untangling why you’re not making sales seems like an almost insurmountable problem, especially when you realize that at the beginning you don’t even really know what you’re selling.

The problem with startups is that you have to figure out WHAT you’re selling AS you’re selling it.

It’s like having a big black bag with a product inside it, and you have to run around selling it to people you see on the street. And worse, you’re not allowed to look into the bag to know what it is you’re selling. You can put your hands into it and feel around, but that’s the extent of it.

Ok, so how do you deal with this? How do you start to figure out what you’re selling, who you’re selling to, and how to sell? How do you get those first few customers? Continue Reading

17 Jul 2013, 6:49pm | 51 comments

So that’s what they were talking about

There’s a great scene from Woody Allen’s Manhattan that goes like this:

Mary Wilke: Facts? I got a million facts at my fingertips.

Isaac Davis: That’s right, and they don’t mean a thing, right? Because nothing worth knowing can be understood with the mind. Everything really valuable has to enter you through a different opening, if you’ll forgive the disgusting imagery.

I think it poses an important question for entrepreneurs:

What can we understand intellectually? And what, to paraphrase Woody, has to enter you in a different way? Continue Reading

2 Jul 2013, 4:30pm | 13 comments

Why you’re on a startup rollercoaster

Let me know if this sounds like you:

Some days you feel like what you’re working on is going to turn into the biggest company, like, ever. You feel like you’re on top of the world. Like all you really have to worry about now is how you should style your hair on magazine covers, and whether Ben Mezrich is going to write a totally unauthorized account of your meteoric rise to fame and fortune. “No comment,” you’ll say when you’re asked if everything he says about you is true.

But on other days you feel like everything sucks. Like all of this was a total waste of time. Like your prospects are slimmer than a candle in a hurricane. Like you’re surprised that you could ever think that your idea could ever go anywhere.

And the funniest thing is that rationally you know that there is very little difference between the days when you feel great and the days when you feel terrible. In other words, even though you feel different nothing meaningful about your company has really changed.

In short: running your company is an emotional roller coaster. Continue Reading

19 Jun 2013, 3:24pm | 19 comments

On negotiating your first few partnerships

This post was republished on PandoDaily.

Dealing with partnership contracts as a new startup is hard.

There’s very little in the way of “standard” terms and conditions when it comes to software (at least that I can find). Everything is specific to the kind of software you have and the kind of company you’re partnering with. When there’s no standard to work with, the first few deals can be kind of a pain if (like us) you’ve never done this before.

The way we managed to get through this was:

  1. Get good advice about what’s reasonable from people who have been there before
  2. Once you’re actually in the contract phase have a good lawyer (I love you Lowenstein Sandler!) to help you craft language and avoid common pitfalls

Because a lot of this advice cost me about time, money, blood, sweat and tears I thought it might be worthwhile to talk a little bit about these kinds of deals on a high level and get into some specific things that we’ve run into that are helpful to think about. Continue Reading

14 Jun 2013, 10:00am | 13 comments

How to read a lot of books

This post was republished on Lifehacker

My girlfriend says I have a thing for books.

I probably spend more money on books than any other expense aside from food. Walking into a bookstore with a good selection (like Strand in New York, or Pyramid Books in Princeton) makes me want to rent a truck and haul their entire stock away to pile in my house so that I can read every single one of them. Continue Reading

12 Jun 2013, 6:08pm | 76 comments

Why are you in such a rush?

This post was republished on PandoDaily. You can read it here.

I see a consistent attitude among a lot of young entrepreneurs both technical and non-technical that I think leads to more harm than good:

They’re always in a huge rush.

They’re always in a huge rush to get the prototype out, to get it on TechCrunch, to get it to go viral, to raise money, to reach a million users in the first year, to be bought for a billion dollars the year after that, to retire to a beach somewhere before they’re 25.

And they always have a ton of reasons for why they’re in a rush:

  • “It’s a market opportunity that’s huge and I’m the first person to realize it so I need to move as quickly as possible to take advantage of it before competitors swoop in and claim it.”
  • “If we don’t get it done by the time I graduate then I’ll have to get a job so I only have a limited time to make it work.”
  • “I want to prove whether or not I can do it so I know if it’s a legitimate career path. So I’m giving myself 6 months to make it happen otherwise I’m going to do finance.”
  • “The funding climate is great right now and I want to raise money before it goes away.”
  • “When I graduate I don’t want to have to move back in with my parents so I either need to raise money for this, or make enough revenue to live on. If I can’t do one of those by June I’m going to have to find a job and shut it down.”

These rationalizations play off of the way an entrepreneur “should” think: move as quickly as possible at all times, do not pass go, do not collect $200. If you’re a real entrepreneur you’re only going to experience success by throwing yourself 100% into your idea from the very beginning even if you have no experience or skills and very little else other than manufactured conviction.

Moving as “quickly” as possible feels good. It feels productive. But ultimately I think being in a rush often slows you down. Continue Reading

11 Jun 2013, 10:00am | 28 comments


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