Dalton Caldwell

Partner @ Y Combinator

Page 4


How Nokia got bamboozled by Hollywood

Now that it seems fairly certain that Nokia is dead, or at the very least, dead as a stand-alone company, it’s easy to wonder what it was exactly they were up to over the past few years. How bad did things have to get for Nokia to flush every piece of software they have ever built down the toilet and adopt Windows Phone across the board?

There were many disastrous projects that Nokia embarked upon to counter the existential iPhone threat, but I would like to talk about one part of Nokia that I had constant exposure to: Comes With Music.

(Note: I should mention that I was running an ill-fated music startup when Comes With Music was rolled out, so I spent a fair amount of time trying to figure out what the competitive threat was, listening to music industry gossip, and having direct conversations with Nokia to see if there were ways we could work together. This experience provided my “...

Continue reading →


“RIP Good Times”: Silicon Valley’s Cuban Missile Crisis

Not too long ago, I found myself sitting in the second row of a conference room, anxiously scribbling notes, at what is now known as the “RIP Good Times” presentation. The presentation has become a cultural touchstone of modern-era silicon valley. I am writing this post because I am of the opinion that some of the context of that particular event has been lost.

At that time I was the Founder/CEO of a Sequoia portfolio company. I remember getting an email from Sequoia asking for my personal presence (ie don’t send a VP in your place) to some sort vaguely positioned mandatory meeting. The meeting was held at a conference center on Sand Hill Road, which I have been to many times since. There were roughly 60 people in the room. It was nicely catered.

You have probably seen the PowerPoint deck. I don’t feel a need to discuss the content of it. At the meeting, I couldn’t have imagined that...

Continue reading →


Oh, the Places You’ll Go!

A few years ago I went through an incredibly difficult period in my life. During this difficult time, I had a newborn son, which made everything both easier and harder. As a parent, I spend a great deal of time reading my son various books, but during this dark time, there was one specific book that came to hold more and more meaning to me as I read it. That book was Dr. Seuss’ “Oh, the Places You’ll Go”.

As I regularly read the book to my pre-lingual son, I began to take notice that it captured Truth about life. To be completely honest, during this difficult period, I got to the point where I had trouble reading the whole book to him without choking up. Sure, laugh if you want.

Oh, the places you’ll go! There is fun to be done! There are points to be scored. There are games to be won. And the magical things you can do with that ball will make you the winningest winner of all. Fame!...

Continue reading →


The Edifice Complex, a silent killer

I recently read the book Starving to Death on 200 Million which chronicled the 2 year rise and fall of The Industry Standard.

One of the key takeaways from the book was the extent that bad real estate deals made the company unfixable. Even though they had a great brand and it would seem there could have been some form in which the company could have lived, bankruptcy was the unfortunate outcome.

What’s interesting to me is how many times the behind-the-scenes details of what killed succesful companies boils down to terrible real estate deals.

In fact, I would argue that one of the clear dividing lines between who lived and died in the dotcom shakeout was who could most effectively wind down their real estate deals. Companies like WebVan, Kozmo, and Garden.com were all stuck with massive physical distribution infrastructure.

A real estate broker once explained to me that one publicly...

Continue reading →


Two brilliant moves that helped create the Apple iOS powerhouse

Most new announcements by Apple are digested and understood by the tech press instantaneously. Great products are great products, and it doesn’t take much time to realize how exciting things like the iPad or Retina displays are. But some moves can take years to completely understand.

So, I now bring you, my two favorite tactical moves by Apple, which I have only recently come to fully appreciate.

Move #1: Windows Compatible iPods

I remember it like it was yesterday. The summer of 2002.

I had a summer internship as a programmer. I was excited about using my new salary to purchase an mp3 player so that I could listen to music at work. At that point in time, I predominantly used Linux on the desktop.

As a devoted Slashdot reader, I was up to speed on the newest mp3 players on the market, and given my massive, Napster-provided music collection, I opted to buy a “Creative Nomad”. The...

Continue reading →


Why having an MBA is a negative hiring signal (for startups)

First off, I’d like to get a few straw-man arguments out of the way. I am not saying MBAs are bad. I am not saying startups should not hire MBAs. I am not saying there are not numerous counter-examples to the points I make below. In fact, I personally know several MBAs that work at or have founded fantastic startups. I have hired & worked closely with individuals with an MBA several times, and will continue to do so if I think the individual is a good fit. Remember, a hiring signal is just that: a signal. Other examples of negative hiring signals are: “earned CS degree from school that advertises on late-night television”, “worked at 4 companies in 3 years” or “2 year gap on the resume with no explanation”. Any positive or negative hiring signal is WAY less important than specific information about a specific candidate.

Now that that is out of the way, let’s get to the point: If a...

Continue reading →


Words that I live by

Never be afraid of failure. No one knows what will happen.

Sometimes you win, and sometimes you lose, but if you give yourself the opportunity to win enough times, you WILL be successful.

Continue reading →


Amazon.com Knee-Jerk Contrarian Game [2004]

The Beatles, “White Album”

“Kindle for your campfire; better yet an apology from Apple Records for creating this toxic waste”

“This CD looks good in a garbage can…..god awful, what were they thinking???”

“This is, put simply, one of the worst albums I have ever listened to.”

It’s important to never take knee-jerk Internet comments very seriously. Rather, they are to be saved and enjoyed.

Continue reading →


BE HATED.

I now say this to you: be hated.

It’s not as easy as it sounds. Do you know anyone who hates you? Yet every great figure who has contributed to the human race has been hated, not just by one person, but often by a great many. That hatred is so strong it has caused those great figures to be shunned, abused, murdered and in one famous instance, nailed to a cross.

One does not have to be evil to be hated. In fact, it’s often the case that one is hated precisely because one is trying to do right by one’s own convictions. It is far too easy to be liked, one merely has to be accommodating and hold no strong convictions. Then one will gravitate towards the centre and settle into the average. That cannot be your role. There are a great many bad people in the world, and if you are not offending them, you must be bad yourself. Popularity is a sure sign that you are doing something wrong.

The...

Continue reading →


The music industry vs AOL

There are similarities between the strategic challenges faced by the dial-up ISP industry (which for the purpose of this post i will treat as just one company: AOL) and the recorded music industry. Both industries were recently sitting on some of the most lucrative businesses the world has ever known. Both industries also happened to peak at the same time: the late 90s. At peak, AOL had 35 million subscribers, each paying a monthly fee. At peak, the music industry was grossing $20B annually from CDs. Times were good.

The usual straw man argument leveled against the music industry is that there was a systemic failure to boldly embrace radical new technology-based business models. The industry “missed the boat”.

By way of contrast, AOL has been consistently making bold moves towards a new business model. AOL management was and is fully aware that the legacy “access” business will...

Continue reading →