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

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 | 28 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 | 26 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

I am a terrible programmer

I recently got this from the co-founder of Artsicle, a startup I interned for over the summer after my freshman year:

From: Scott Carleton
Subject: just refactored your find_art.js that you did over a year ago
Part of me is thinking: in some ways, you were a terrible programmer
Other part is, well shit, it’s worked perfectly for the last 20 months and I’ve never had to touch it. :)

Scott is absolutely right: I am a terrible programmer. I don’t comment my code very well. Sometimes I ignore the DRY principle. I tend not to use fancy ternary statements, or worry too much about whitespace. My data structures can get ugly sometimes.

But in other ways, I (dare I say it) am a pretty good programmer. For example, Artsicle is a Rails shop and prior to working for them I had only had very limited experience in Rails or any true MVC framework. After a few weeks, I had mostly picked up the codebase and was building features without inordinate trouble.

I also ship stuff. A lot of stuff. I’ve probably built and released 20 apps over the past two years in a variety of languages and frameworks from Python to Rails to Node to Backbone.

42 Floors even publicly offered me a job to become a programmer for them. You can argue that it may have be undeserved, but either way given my ability to produce products with code, it seems that we have a dilemma on our hands.

Am I a terrible coder, or a good one? Continue Reading

8 Nov 2012, 7:46pm | 103 comments

Taking off the rose colored glasses

On Danielle Morrill’s suggestion I’ve been reading a book called The Happiness Hypothesis. The author, Jonathan Haidt combines ancient philosophy (including my personal favorite, Stoicism) with modern social and psychological research to paint a picture of a happy life that I find really compelling. What struck me however is how applicable a lot of what he says about the mind is to startups.

The thing that stuck out the most is a passage where he describes how bias works. He talks about a study in which pairs of research subjects are given a real legal case to read. One is assigned to play the defendant and one is assigned to be the plaintiff, and they are given real money to negotiate with. He says:

When both players knew which role each was to play from the start, each read the case materials differently, made different guesses about what settlement the judge in the real case had imposed, and argued in a biased way. More than a quarter of all pairs failed to reach an agreement.

However, when players didn’t know which role they were to play until after they had read all the materials, they became much more reasonable and only 6 percent of pairs failed to settle.

What he’s saying here is that when players knew their roles in advance, they genuinely read the information differently and came to different conclusions about what a reasonable outcome from the case was. This reminds me of how people evaluate their own startup ideas. Here’s how it works:

1. They come up with an idea

2. They get very excited about it

3. They avoid doing real research on competitors.

4. If they happen to come across information that indicates that there might be problems with their idea they dismiss it immediately.

5. If they come across ANY positive sign that what they’re working on might be valuable they get incredibly excited about it, and cite it as a reason why their idea will work.

6. They think that their blind insistence that their idea is The Next Big Thing is why their vision will come to reality

Conversations with these people tend to have a very similar script.

Founder: “We allow companies to view their support requests from customers as threads and then post those threads publicly to avoid answering the same questions over and over again.”

Me: “What about Zendesk? Doesn’t that do the same thing?”

Founder: “Yes, but Zendesk only allows you to submit requests as text. We’re going to allow customers to submit videos of themselves describing the problem. I read an article in TechCrunch last week that said video is the future of online communication, and we’re super passionate about videos so that’s why we think we can win.”

There are a few problems with this approach. Continue Reading

25 Oct 2012, 5:32pm | 2 comments

Selling Umbrellas in a Synagogue

A few months ago, Twitter invited me to participate in their advertising program. Basically what they do is allow you to purchase follows via a Promoted Account and purchase clicks, favorites and retweets via Promoted Tweets. I poked around the interface for a little while and ultimately decided not to try it out. To me, there’s something kind of icky about purchasing Twitter follows (even from Twitter itself).

But I got this in an email from them this morning:

Given that they were nice enough to credit me 100 bucks I decided to put aside my misgivings and give it a shot. We’ve been thinking a lot about online advertising recently at my startup, and so I thought it would be interesting in comparison to Adwords and LinkedIn Ads.

I set aside $50 to spend on a “Promoted Account” and $50 to spend on “Promoted Tweets”.

The Promoted Tweets function allows you to pick a few of your tweets and have them show up in other peoples’ stream. I selected a few of my most scintillating 140-character tidbits and let ‘er rip.

Those are pretty cool results! An 8% CTR is rather astoundingly high by online advertising standards.

The next thing that I noticed is that promoted accounts don’t seem to work too well:

They tell you to optimize your bio so people can connect with you more readily. I neglected to do so and forged ahead with all of my current settings. The result was that for $11 I got 6 followers.

My first thought was “this is dumb”. The ROI on something like this has to be very low. For the Promoted Tweets, I did get 130 clicks, but I couldn’t target those clicks at all beyond geographic region. And as far as the followers, I already have 3,000. How valuable could 6 extra really be?

For a total of $61.81 spent it didn’t seem like I was getting very much.

But as I thought about it more, I realized that what made that money seem like such a bad deal, was tied to the reason that advertising on Twitter feels icky to me: when you throw ads onto Twitter, you start treating it in the same way that you would Google. You begin to start measuring things like CTR, conversion rate and ROI.

But the way people interact with Twitter is fundamentally different from the way people interact with Google. And so measuring things like CTR and conversion rate on Twitter is completely missing the point. Continue Reading

18 Oct 2012, 9:00am | 11 comments


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