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 | 14 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 | 77 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 | 32 comments

19 things that should be fixed

I don’t normally do list posts, but I thought this might be a fun departure from my usual 2,000 words. Maybe you’ll find your next startup idea in here. Feel free to add your own to the comments section.

1. When they bring you bread and butter and the butter is too hard to spread

2. When I call in to a customer support line for the 10th time they still have no idea who I am or what my account number is

3. If I’m disconnected from a customer support call I have to go back through the phone chain again and start over

4. If I’m looking at an ad it doesn’t have a box at the bottom that says “Is this relevant to you?”

5. Chrome opens up a new process every time I open a new tab

6. I forget 99% of the things I read

7. My weather app can’t tell that I’m going on a trip soon and show me the weather in the place I’m packing for automatically

8. It takes 4 emails back and forth to schedule a coffee meeting with someone

9. When light switches aren’t backlit so you can’t see them when it’s dark

10. When they don’t put light switches on the left side of the door so that you can easily turn them on as you walk into a dark room

11. When doors have “pull” handles and are actually “push”

12. Window latches that don’t tell you what state they’re in

13. When I’m on a train and four people have MiFi’s and I can’t pay to use one of them

14. When buildings have great comfortable seating areas for people to do work in but have forgotten to put power outlets near them

15. When a sign in form says “username” but I actually signed up with my email

16. When a sign in form says “email” but I actually signed up with a username

17. When a video player crashes before it starts playing, I refresh my page, and am subjected to the same ad I just watched

18. When a bus has wifi but it doesn’t actually work so I end up wasting 10 minutes vainly turning WiFi on and off, reconnecting, and then refreshing the page

19. When I have no more clean socks

22 Apr 2013, 2:06pm | 23 comments

How to figure out what you’re good at

This post was republished on Lifehacker.

A lot of success advice revolves around the idea of “being honest with yourself about the things you’re good at, and pursuing those things relentlessly.” We’re told that all successful people can be boiled down to a paragraph which states their chosen field and the personal style they brought to it which allowed them to be successful.

Here are some examples:

Bill Gates: entrepreneur and philanthropist. intensely smart, workaholic, ruthlessly competitive.

Christopher Hitchens: master wordsmith and essayist. contrarian. known for his outspoken views on Athiesm and his pugnacious writing style.

Oprah Winfrey: media mogul. revolutionized the daytime tabloid talk show. philanthropist. known for her ability to get celebrities to open up about their lives on TV.

Woody Allen: writer/director/actor. known for raucous one liners, Marx-brothers inspired slapstick comedy, portrayal of neurotic Jewish characters in romantic comedies, and a prodigious output of films over his long career.

Because successful people can be described in this way, the common wisdom goes, if you can figure out what you’re good at in a similar way it will help you be successful.

In order to figure out what you’re good at, a common piece of advice is: “Be brutally honest with yourself about it.”

But the problem with this advice is that for most of us younger than 22, asking ourselves “What am I good at?” returns a blank response.

Most success advice doesn’t recognize this because it’s generally written by people who have spent a lifetime figuring out the answer to that question. By contrast, even the most prodigious 20-year-olds among us probably have been working successfully for five years, if that many. Continue Reading

31 Mar 2013, 11:54am | 40 comments

How to make a million dollars

Some people know how to quiet a crowd.

Conrad looked at the floor. He crossed his arms, standing lazily in the center of the stage. Subtle murmurs from the audience gradually died down. Slowly they focused their attention on him, waiting.

As he stood there, they looked more closely, drawing in their breath. Perhaps they were missing something. They moved their eyes slowly over his jeans and t-shirt. Why was he just standing there?

A few stray coughs echoed through the back of the auditorium.

The seconds ticked by.

Conrad could hear the audience’s breathing stop. Silence crescended through each row as they waited for him to say something – anything.

He looked up.

“How many of you are not where you want to be in your lives?” Conrad said. A few hands crept into the air.

“How many of you have started a business but are having a hard time making it a success?”

More hands.

“How many of you want more users, or more revenue? How many of you want to raise money?”

“How many of you want to be independently wealthy?”

More hands raised. Conrad smiled knowingly.

“I can help you with those problems. You see, I was once where you were. Broke, fresh out of school with no money. Working on a few business ideas on the side.”

“In 15 years I’ve built and sold two businesses, both for more than 100 million dollars.” Conrad spaced out the words ‘million dollars’ for emphasis as he walked to the left side of the stage.

“I’ve been featured in pretty much every publication you can think of. I’ve done it all. And now I want to give it back.”

“So what I’ve tried to do is take everything that I’ve learned over the past 10 years and condense it into this talk.” Continue Reading

8 Feb 2013, 3:33am | 33 comments

Here’s what I learned hanging out with Jason Fried

Discuss on Hacker News.

I went to meet Jason Fried so I could learn how to stop selling software by accident.

Since I started programming 10 years ago, I’ve made a fair amount of money online. But those sales were mostly coincidental.

By that I mean, I never thought deeply about how and why products were bought. I would build something, release it and drive traffic to it. Sales would almost always trickle in. But I never took the time to understand who was buying and why. I never worked on refining my sales copy, or understanding which forms of traffic brought the most customers.

Once I released a product I would do one of two things: start working on adding new features or start working on something else. I didn’t take time to understand what was working and what wasn’t. I wasn’t really interested in refining and simplifying – just seduced by the prospect of building something new.

You can learn things by doing this. I’ve learned a lot in the last 10 years. But I think getting from being good to being great requires something else. Building great products requires constant practice at the art of building understanding. It also requires getting rid of everything except what’s absolutely necessary.

With this in mind, what my co-founders and I have been working on over the past few months with Firefly is learning how to sell deliberately. When we make a sale, we want it to be because the copy addressed customer pain and offered a solution they could connect with on an emotional level. We don’t want to make a sale because a customer is smart enough to swim through a list of features he doesn’t care about, and come up with a reason to pay money on his own. Continue Reading

7 Jan 2013, 3:41pm | 29 comments

The choices are fake and the truth is all made up

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

I like the holidays because they’re a chance to take my foot off the gas a little bit, get out of the car and reset the engine. They’re a chance to take a look at the map and make sure I’m headed in the right direction.

Over the years I’ve had a lot of conversations with some very smart people about what it takes to be successful. And as I get older, it’s interesting to get a chance to look back and see the parts of the conventional wisdom that turned out to be untrue.

I guess you can call these things myths, but really they’re statements that I can slip into a conversation with someone and have very little fear that they’ll do anything other than nod in agreement at their self-evident truth.

Two things have stuck out to me lately. The first is that the highest opportunity cost for an entrepreneur is when she’s in her early twenties. The second is that an entrepreneur has to drop every other interest in their lives except for business in order to be successful. Continue Reading

27 Dec 2012, 11:59pm | 10 comments


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