Who is this guy?

Learn from the Best: 10 lessons I learned from mistakes at Amazon, Google and Facebook

I didn't hold out for billions. I sold my app for millions. In 2008, I built an educational website for my 10-year-old daughter. Six years later, I sold it for seven figures. In between, I had a brush with Rupert Murdoch, Jeff Bezos, Ben Bradlee, bankruptcy and jail. Survived a flood, lost a parent and a business, then got fired. Lost a house and sold another, lost two girlfriends and got engaged. Lost a boat and a car. Bought another one of each, and sold a plane. Almost gave up. (Click below to download .pdf)

I’m not crazy. I’m just early.

The year was 2006. The iPhone did not exist. Facebook was losing millions — it was still years away from profitability. But I could see the writing on the wall: Newspapers were doomed. First, I sounded an alarm. Then I offered a radical, extensive, 10-point survival plan. I called it “NewRulesForNewspapers.” I was mocked, ridiculed, and ignored. After two years of frustration, I said “Fuck it. If newspapers won’t take my advice, I’ll just do it myself.” And I did. See story

You’re not crazy. You’re just early.

It's something that a lot of people can't do;
Trying is hard, that's why people don't do it;
Losing is hard, they can't make it through it;
But not you. See story

“I alone can fix it”

I hate Donald Trump. But when he said, “I alone can fix it,” I knew exactly what he meant. Because that’s how I feel about online dating. I’m not saying it out of arrogance. I’m saying it out of lived experience. I’ve been through it all. I’ve sat across from women like Karen – me hopeful, expectant – and then felt that gut-punch of rejection, the hurt that leaves you reeling for days. That night, I realized something bigger: if I felt this bad, millions of people must be feeling the same way. See story

The Art Department

We’re a small, independent lab exploring the art of human-guided intelligence. Our belief is simple: AI is not a science project — it’s a new medium. Here we treat engineering as design, design as psychology, and psychology as communication. See story

He taught me everything I know about computers

I remember a time when I needed the system to distinguish one capital letter from another, probably to set the width of an indent for a drop cap. But the system can’t “see” letters. It only sees zeros and ones. So John looked in the CAWTs — Character And Width Tables. He found unique codes for each capital letter, but there was no way to pass this value to the markup engine. I saw no way to make this work. I was ready to give up. But John said, “Alan, we’re not gonna let this machine beat us.” See story

Our origin story

That night, something clicked: If I feel this bad, millions of people must be feeling the same way. Every. Single. Day. Not because they’re unlovable, but because online dating is designed to fail. Apps only succeed when their users fail — because failure means more subscription fees. Success means the app loses not one but two paying customers. See story

A Passage to India

I had asked Rackspace to retrieve some data from the database. Not mission-critical data, just something I wanted. At the same time, I think a backup script was running. I don’t remember all the details. But during the process, Rackspace corrupted both the production database and the backup database. MySQL refused to load either one. In that moment, I realized all my work, all my time invested, all my money in TweenTribune were gone. See story

Buying a car from a 6'7" salesman

I just bought a 2024 Subaru Outback XT with 4,000 miles for $32K plus taxes, title, yada, yada, yada from Casey Subaru in Newport News, VA. It was the best car-buying experience of my life. Now let me tell you why. Buckle up. See story

In Aaron Sorkin, I see myself

I’ve always felt strangely understood by Aaron Sorkin’s writing. In The Social Network, Jesse Eisenberg’s Mark Zuckerberg gets called an “asshole” by his girlfriend in the opening scene. It’s a brutal word, but it’s also precise: his intensity, his relentless logic, his inability to soften for others — it all overwhelms her. See story

From cockpit to code

In an emergency — an engine failure, an instrument malfunction, a total electrical loss — the first impulse might be to ask for help. But ATC can’t fly the airplane, and the Coast Guard won’t be coming to save you. You need to fly the airplane. Because it can be the difference between life and death. See story

“I am the steward”

Spend the money where it helps. We give it away now to stand up newsrooms, not someday through a distant foundation. Cash to reporters, editors, photographers, developers. Tools that work. Systems that don’t break on deadline. See story

Transparency and authenticity are my brand

People already have hardened negative opinions about AI. As an Agent of Change, I realize how daunting the challenge is. But NO challenge is ever daunting to me, because if I have a plan I can succeed: “Plan your flight, and fly your plan.” I learned that from Capt. Bill Kight. See story

Most developers think building a website or app ends when “it works.” It doesn’t.

I test everything I build across six phones, two tablets, a PC, and a Mac — iOS, Windows, Android, Safari, Chrome, Firefox. Different screen sizes, devices, OS, browsers and cache states. Because what’s flawless on one device can break on another, and most users will just walk away if and when that happens. See story