The Speech That Launched a $65 Billion Enterprise

In the spring of 2005 I attended a speech at the Harvard Computer Club by a guy I knew named Paul Graham. I’d worked for at his tech startup, Viaweb, and I knew he was a smart, generous, and entertaining guy so the speech would be worth attending.

The room was, surprising to me, packed with attendees. Because I knew what Paul looked like I could pick him out from the crowd. I approached him and wished him luck. He said with a laugh, “Ah! You’re here. Now I know I can’t exaggerate anything or make stuff up.”

He then took the stage and gave a speech that killed, the audience hung on his every word. His presentation was a good one not only because he was a skilled writer and speaker, it was effective because he intuited the reason students were there to see him – they wanted to learn how to become rich like him.

Paul was, at this point, worth several millions of dollars from the sale of his company to Yahoo and from his single year working there. He was wealthy but also a member of the Harvard Computer Club’s tribe. His words resonated because he spoke the language of computer nerds.

But Paul didn’t limit himself to just programming, as many do, he could speak equally well about literature and art (as his book “Hackers and Painters” attests). He was as comfortable discussing the works of Emily Bronte as recursive functions in Python, which looks something like this:

n! = n * (n-1)!, if n > 1 and f(1) = 1

Like I said, a smart guy.

But Paul didn’t talk about recursion, instead he gave the audience what they wanted – a review of how he made millions creating a software company. It had a lot of insight and was a good guideline for aspiring tech entrepreneurs. He later posted it online and it’s worth a read.

I’ll admit, parts of it were nice for me, a former employee of his, to hear. In particular the part “Almost everyone who worked for us [at Viaweb] was an animal at what they did.” Viaweb had an extraordinary workforce, being an employee there sometimes felt like being a member of the Navy SEALS. Like the recently sainted Steve Jobs, Paul had a way of attracting the most talented and fostering innovative thinking among us.

After the speech, I cut through the mob that had assembled around him and told him it was great. He smiled and said, “Did you like the part about Linda Wilk?” I did because I knew exactly who he was talking about when he said, “The woman in charge of sales was so tenacious that I used to feel sorry for potential customers on the phone with her.”

As I turned to leave, another took my place and said to Paul, “I took a train from Virginia just to speak with you.” Later I would learn this was Alexis Ohanian, then a nobody college student at the University of Virginia and now known as the creator of Reddit, the first company Paul funded.

The small investment that Paul provided for Reddit eventually expanded and grew into something called Y Combinator. It put together a string of successes, including Reddit, Airbnb, and Dropbox. It’s now known as “The Harvard of Startup Schools” because entry into its program is about as prestigious and difficult. Companies in its portfolio have a combined value of $65 billion.

And, unwittingly, I attended the speech and witnessed the conversation that sparked its creation. Interesting things happen when you break convention, get off the couch and go somewhere. Tonight, go to a speech or a show and talk to people. I guarantee something cool will happen.

Who is Driving Your Life

Over the weekend I ran into two different guys who were both experiencing the same thing – burnout doing tech sales.

The first did it for 20 years and became a semi-functional alcoholic. With nothing to do on 18 hour plane rides, he took up drinking massive amounts of booze and it turned into a serious addiction. Standing 6’4”, at his worst he weighed 135 pounds and was a mess. He turned to AA, quit his job, and started his own business. He hasn’t had a drink in 11 years and is now enjoying life.

The second guy I talked to was still doing tech sales but was experiencing some disillusionment. Last quarter he was under so much stress that he nearly passed out walking on the beach. He saw a doctor but he still feels the pressure. He’s looking around at other jobs but he’s not sure if it will be any different somewhere else.

Both these guys, neither who knew each other, both said the same thing – they were determined to “make it.” Once they landed that killer deal, they could get off the treadmill. The guy who left his job said, “I quit when I realized there would always be a better car, a bigger house, and more toys. It would never end. I was charging at target that was always receding.”

It reminded me of a story Seth Godin, in his speech at Hubspot Inbound conference, told of being driven 300 miles in India by a hired driver. Hearing his account, I commiserated with his plight. I’d been driven great distances in Tanzania and it’s something I won’t forget. Riding as a passenger in a car on Tanzanian roads was the most dangerous part of climbing Mount Kilimanjaro.

Godin, while being driven, noticed his driver passed other cars at every opportunity. When he was stuck behind someone, the driver would ride other car’s tails and lay on his horn until they moved aside. Pushing, shoving people out of his way, the driver pushed the tiny car to its limits.

It was only after they finally reached a clear stretch of road that the driver slowed down.

In effect, the driver allowed other cars to dictate his behavior. He was always striving and pushing to gain, what? Something he could have done all along.

It brings up an interesting question – who exactly is dictating the path of your life? Is it other people? Are you allowing them to tell you what you should do, value, and pursue? Or does your life direction come from yourself? Until you confront this question, you will never be free.

User-Centric Design

When I attended the University of New Hampshire, it was located in a small town with a limited number of restaurants and stores in one central area.

None of us had cars and public transportation was spotty so everyone walked everywhere. There was one path we always took to get to the convenience store, restaurants, bars. This major hub for students had this layout:

main streetIf you examine this map closely, you’ll notice two busy one-way streets merging downtown. In this map, all the traffic, both cars and the majority of walkers, was headed towards the right, where the bars and stores were.

At one point there was a crosswalk that everyone used, drawn in blue below.

main street-crosswalkThen one day someone in the city council decided this crosswalk was a hazard, took it out and replaced it with a new, safer formation. It went like this.

main street-new crosswalkI agree, this new formation was much safer than the old. No longer did pedestrians walk in front of two merging thoroughfares. The only problem was no one used it.

The reason no one used it should be clear from the map. To get to where you wanted to go (across the street and to the right), you had to first go against your natural direction and backtrack. Also in this new formulation you had to cross two roads rather than just a single one.

I used to watch section of the street often because my apartment overlooked it and I regularly read novels and smoked cigarettes at the coffee shop nearby. I would sit there for hours, watching enormous groups of students cross the street along the old path where the crosswalk used to be. Not a single group used the newly installed crosswalk, it was too much of a hassle. Something dictated from up high with no regard to how people actually functioned.

Once I was sitting at the coffee shop with two friends, Steve and Bob. Steve noticed the same traffic pattern I did and said, “Someone should repaint that crosswalk.” The other friend, Bob, sat back in his seat, stroked his chin sagely and said, “That’s a good idea.”

Later that summer at 4 am on a Tuesday night, Bob did just that. In an act of “helpful vandalism”, he repainted the crosswalk. He videotaped the act for posterity using my apartment window. You can watch it here:

Feel free to skip around but some key parts are at 2:30 when a car comes by and Bob runs and it happens again at 5:00. You can also see where the cars leave a trail of wet paint on the road.

Bob would later to get his PhD in data visualization but I think his true calling was in user design. He realized one important thing about good UI – it’s more important to notice how users actually use something and not how you want them to use it.

My Worst Cold Call

My worst cold call happened a year ago today. I remember it well because it was near my birthday. That’s right, prostate I went on a disastrous sales call on my birthday right after getting a divorce. 2014 was a bad year for me.

I was just getting started doing freelance work after being introduced to it by the guy down the street. He’d been doing it for years and floated me a few assignments when I told him, seek “I need the work, physician I’ve got mouths to feed.” Pathetic but true.

And I enjoyed it, writing for pay. This will sound stupid but I didn’t know you could make so much money doing it. I’d always listened to writers complain about their low pay and tight deadlines and read tales of Melville dying unknown and penniless and only achieving fame long after he was dead. I foolishly believed it.

Turns out people hate writing and will do anything to avoid it, including paying you to do it for them. Because writing came naturally to me, I always thought it was an easy task that was not worthy of pay. It was a pleasant surprise that, no, you can earn a good living doing it.

As part of my plan to expand my freelance business, I sent out a bunch of emails to local tech companies. In my career, I’ve had the good fortune to work with some smart people at high performing companies and done some interesting things. So I cited these with abandon. It lead to a couple of bites, one of which became my first regular paying client and the other was the world’s worst cold call.

It was at the Harvard Innovation Lab, a student run startup that looked promising that got great press. They didn’t have any money but were interested in talking with me because I was an early employee at a start-up that was a big success.

I got dressed up, drove to Harvard, and met with the guy. It started out promising and, oh God, please don’t make me relive it. Let’s just say it was one of those moments where you feel like a total buffoon afterward. A memory that you remember with a wince. I didn’t know what I was talking about, I didn’t know what he wanted, and it went from bad to terrible in seconds. The thing was a total flame-out.

But the part that burned was he was so dismissive of me. He didn’t have the time to be polite, he was arrogant. “I am the cream of the crop and don’t have time for nonsense,” was the message he conveyed.

Partially, he was right. I did look foolish. But sometimes it is a good practice to play nice as you never know when you will encounter that person again. I think of the scene in Election where Matthew Broderick is undone by the lowly janitor to whom he was rude. One maxim I follow is, “Be nice to those you meet on your way to the top, as you never know who you will meet on your way down.”

The good news is I rebounded and over time I refined my sales technique. In those early days I accepted every interview I could just to practice. By doing this I learned what worked, what didn’t, which lines I could say that would draw a laugh, and how to tell a compelling story.

After a lot of work doing this, I now have a regular list of paying clients and am getting referrals. Word of mouth is a great thing, it removes the need to chase down leads and allows you to devote more time to billable work. And I love having several bosses instead of being tied to the whims of one. That’s real job security for me.

A couple months ago I did a search on that startup where I gave my worst sales pitch. The site is down and has been since I checked. Looks like one of us, the one that didn’t go to Harvard, knows how to set up a viable business. How do you like them apples?

The Smithereens

I was 14 years old when I first heard the opening bass line to The Smithereens “Blood and Roses.” It was played as part of a commercial for a movie called “Dangerously Close.”

In my adolescent mind, I made the mistake of thinking the movie must be as good as the music that went along with it. This was a big mistake. Reading Wikipedia, I learned the film was made by a man dubbed “the new Ed Wood” who produced a movie called “Bulletface” and later got into legal trouble in a failed movie deal with Guam.

Funny thing is, watching the video now, you can see why I made this mistake. The song is so good it makes an obviously kitschy B-movie look almost like “At Close Range” mixed with “The Breakfast Club.” A stretch maybe but remember I was 14 years old.

I mean, listen to that bassline! There’s something so dark, menacing, and noir-ish about it that would lend itself well to any movie.The lyrics were also mysterious. The incident he is describing is a bad situation but it’s unclear what exactly happened.


Not a band that will be confused with contemporaries Ratt and Poison

Another thing that helped was the un-glamorous look of the entire band. This was as far from LA hair bands as you were going to get. Just a couple of kids in leather jackets from New Jersey who let the music speak for itself. The drummer wore glasses for God’s sake. The guitarist looked like he was comfortable having a couple beers at the local bowling alley. The lead singer wasn’t exactly dashing. If I were in charge of who did what, I’d put him as the bassist in the background.

But it lent an authenticity to the lyrics they sang. When a not-so-great-looking lead singer sang:

“I used to travel in the shadows
And I never found the nerve to try and walk up to you”


“I’ll do anything I have to do
Just to win the love of a girl like you, a girl like you”

coming from him, it was a believable tale. And it resonated among people who felt the way he did. It certainly did with skinny, insecure high school me.

But there was something dark and edgy to the music they sang. The lyrics were plaintive and sincere but vaguely unsettling, like an Edward Hopper painting. In my mind it was music that would go well with drinking bourbon and smoking cigarettes in a dive bar.

The Smithereens will be playing in my hometown Londonderry on Friday the 13th. I’m looking forward to seeing them finally after all these years.