Jay Adelson speaking at FailCon 2010. Photo by Dean Takahashi of VentureBeat.

Jay Adelson speaking at FailCon 2010. Photo by Dean Takahashi of VentureBeat.

As executive confessions go, the one delivered by former Digg CEO Jay Adelson in a public forum this week stands out as one of the most remarkable ones I’ve ever seen for both its brutal honesty and fearless self examination.

The occassion was a fireside chat at FailCon 2010 with Cathy Brooks, who runs the Story Navigation workshops that I wrote about previously. I wrote a column about FailCon that you can read here. Even though I couldn’t fit Adelson’s remarks into that column, I couldn’t stop thinking about his session even after I had filed. So I wanted to circle back to them here and explain what I found so amazing.

Silicon Valley executives are often packaged in so many layers of spin and carefully crafted images, that when someone stands up and speaks from the heart, with no filters, it can be downright startling. Like a sudden gust of wind that catches you off guard and almost knocks you off your feet.

That was the feeling I got as I listened to Adelson’s remarkable exploration of his own failings. While many folks in the room were understandably anxious to hear about the failures of his business ventures, I was captivated by his unvarnished discussion of his personal failings, as a father, as a husband, and as an entrepreneur. He spoke with great authenticity and honesty about his ongoing fight to strike a healthier balance between his intense drive as an entrepreneur and the toll it takes on his family and personal life.

Adelson isn’t exactly a household name, though in Web 2.0 circles he’s somewhat of a giant. Here’s some quick background on him. In 1998, Adelson started Equinix, an Internet infrastructure company that went public after Adelson stepped aside at the suggestion of investors to let another more “professional” CEO step in and lead the IPO. Adelson eventually lost control and was pushed out of the company, to his enduring regret. That experience was fresh in his mind he was contacted for advice by another entrepreneur, Kevin Rose, who wanted to discuss his idea that became Digg.

Adelson had left Silicon Valley and moved to New York after he left Equinix to get away from the craziness and lingering bad feelings. But ensuing conversations with Rose got him so pumped about Digg, he wife told him he had a “wild” look in his eye. Reluctantly, he found himself agreeing to become CEO of Digg. And he took the role while commuting from New York.

And this is where the personal confessional begins. Even though he had vowed to steer clear of another start-up, he found himself too obsessed with the idea of Digg to say no.

“Next thing you know, I woke up in the back of the alley with a bump on my head five years later,” Adelson said. “And I loved every minute of it.”

Asked about regrets, Adelson said he doesn’t second guess the decision to turn down the two serious offers Digg received. Instead, he again circled back to the personal toll.

“Looking back on the personal, there are moments in time when I wish things were different,” Adelson said.

When he started Equinix, his first child had been born just two months earlier. He rationalized his decision at the time by thinking, hey, it’s the dot-com boom, and I want to take my shot, and if it fails, at least I can say I tried.

“But I don’t think I realized at the time, even if you go home at 6 o’clock, which I rarely did, you don’t realize how much you take home,” Adelson said. “In your head, you’re at work. Even when you’re at home, or rocking your baby to sleep, you’re there at work.

“I wish I had the discipline to shut it off,” he continued. “This is one of the reasons I left Digg. I think I have a problem there.”

Once Adelson is working on a start-up, he find he “puts the blinders up. And to some extent, you can’t stop yourself. It’s a compulsion.”

The reasons he left Digg back in April, of course, were more than just personal. He acknowledged there were disagreements over the direction of the company. But even after he left, he found he hadn’t really left.

“It took me four months after I left Digg for the process to slow down in my head,” Adelson said. “I still wake up in the morning and I’m still working there.”

“I love the emotional context,” he explained. “Everything about Digg and Revision3 (an online video company where he is chair) is about changing something bigger than me. And I get very involved.”

Adelson knows he’s not alone in his start-up compulsion. And to illustrate his point, he asked the room full of 450 entrepreneurs how many of them reached for their smartphone the moment they opened their eyes in the morning. About half raised their hands.

“That’s probably not okay,” he said. “Look into my eyes. That’s. Not. Okay.”

Last year, Adelson and his family moved to back to Silicon Valley even though he didn’t expect to stay at Digg much longer. He was starting to advise more start-ups here and he thought that maybe being closer to them would help him achieve a better balance. He said he’s trying hard to stick to his decision to not jump back into a start-up. He said he’s struggling because he’s hearing about so many amazing opportunities.

“Can  you stay on the sidelines for six months?” Brooks asked.

“Ask me that again in six months,” Adelson said. “It’s been very difficult.”

Brooks asked Adelson what he tells other prospective entrepreneurs about how to weigh the personal costs of doing a start-up against the thrill of being in the game.

“I think that it really just depends on you.” Adelson said. “It’s an emotional decision. Is it interesting to you? What it really comes down to is: Do you enjoy your life every day when you wake up? Do you grab that Blackberry first thing in the morning because you really care about this idea and the people you’re working with? Or do you grab it because you have to?”

Here is VentureBeat’s video of Adelson’s talk: