About
The long version
My path to Italy didn’t start with a classroom or a travel brochure. It started in a single room in Calabria, in the summer of 1983. One bare bulb hanging from a frayed cord. A woman whose language I didn’t speak, feeding me and then crying because I couldn’t eat any more. I was seventeen, I had everything, and I went home to Los Angeles unable to explain to anyone why none of it counted.
That December I drove to my father’s house to take him to his own company Christmas party. We had spent the year talking about my coming into the business. The plan was Austin, his factory there, and eventually the whole thing. He had been sober about a year. He was not sober that night. I got as much coffee into him as he would take and we went anyway.
Eleven days later I was identifying his body.
Then the house burned down. I moved in with the family of the friend who had taken me to Calabria, and it took me a while to work out what business they were in. I knew. They knew I knew. We never once discussed it, and they were good to me.
Then I inherited millions, which fixed nothing at all. My brother was already gone by then, a car accident with drugs in it. So were two friends, and a run of aunts and uncles. It felt like I was always at a funeral, and no amount of money made any of those rooms less empty.
The next summer Los Angeles filled up with the Olympics and I wanted out of it. Italy again. That was the trip where I met Paola. In January 1985 I left the Hollywood Hills and the Porsche behind for a $150-a-month apartment and a $1,000 car, in a country where I barely spoke the language.
1983-84
The year it all came apart
Calabria in the summer. My father dead by the second of January. The house gone not long after that. By the end of it I had money and no reason left to stay in Los Angeles.
1985-86
Two years in Italy
I stayed a couple of years, learned the language, and came home with a completely different idea of what a good life looked like. I later wrote a 12-part series on the road that led there.
Read the series →1994
A company built in a garage
I started L.A. Online, a graphical bulletin board meant to carry real-estate listings. The design work took off instead, so we followed it. The company became Cyberspace Information Systems and then Cyberspace HQ, and this was the year we left the garage for an office: 450 square feet, two of us in it. We built the first email software for Windows and the first Windows domain name server. The client list ended up including the Navy, MCI, and Nike.
1997
AddWeb, before SEO had a name
We built AddWeb, one of the first professional search-optimization tools, years before anybody called it SEO. It sold millions of copies and put us in the top 2% of all business software in the country.
1999
The $250 million lesson
On paper we were worth $150 million. The Navy ran our software and hired us for security work, and in late 1999 a VC offered to fund us and take us public. I wouldn't give up a piece of my own company, so I said no. They backed a weaker competitor instead, and that founder exited at $250 million. The irony isn't lost on me: I spent that same year on conference panels telling rooms full of people the valuations were insane and the whole thing was going to crack open. They laughed at me. I was right about the market and wrong about my own company, and both of those cost me.
2000
The crash, and the lawsuits
Most of our customers were dot-coms, so when they went, it stopped being a question of how fast we could grow and became a question of whether we'd still be here. Around the same time we were fighting a copyright suit and a false-advertising suit against companies many times our size. We settled both. The legal fees bled us dry, and that was the part that finished me.
2001
Best of eBusiness, Comdex
In the middle of all that, a 21-person team and I won Best of eBusiness at Comdex for ServiceTraq, our SaaS CRM product. In tech terms that's somewhere near winning a World Cup. The show ran that November, two months after 9/11. Attendance collapsed and no buyers came.
2006
I sold the company for one dollar
Six years of drift after the crash, and I was done. One employee had stayed through the worst of it and wanted to keep going, so I sold him the whole thing for a dollar and left the software industry, certain I was finished with tech for good.
2006
A hobby that became Culture Discovery Vacations
The same year. Paola and I started renting apartments to Americans who wanted Italy beyond the postcards. Guests asked for tours. Then cooking classes. We kept saying yes.
2007-08
Walking away from a C-suite offer
Sure the Great Recession would sink us, I took a turnaround-consultant contract with a large software company. It carried an option: after six months I could join the C-suite with a large salary and a cut of online sales. They never acted on my advice. Meanwhile our tours were selling out. I turned the offer down, twice.
2011-today
Eight countries and counting
We opened a second location and never looked back. Culture Discovery Vacations now operates across Italy, Spain, Portugal, Croatia, Bosnia, Montenegro, Argentina, and Uruguay. Now one of the largest small-group tour operators in Europe, built on keeping more than 70% of guest spend in the local economy.
Today
The house I noticed before I met my wife
On that 1984 trip, before Paola and I had met, I kept driving past the same derelict farmhouse on the way back from dinner. Every night. I remember thinking how good it would be to bring something like that back. Years later she asked whether I wanted to see her family's country house. We drove out through a maze of dirt roads and pulled up in front of it. Same house. It had been in her family for more than three hundred years, and by then it was close to falling down. We have been restoring it ever since. We named it Villa Eddarella, after Paola's mother Edda. There is a five-hundred-year-old wood-fired oven on the back patio and a view straight down the Tiber valley. It is where I live.
This is my granddaughter Aria, on the Amalfi Coast.
I started this story with a house full of money and a run of funerals, and I have spent the forty years since building the opposite of that. Everything on this page was in service of the picture on the left.