Men, Money, Work and Kids

Let’s get a few things straight from the start:

• My kids (ages 18, 16, 7) are the most important thing, along with my wife, in my life. I love them so much it hurts
• I work damn hard to make a lot of money
• I really don't care what anyone else thinks
• It has taken me decades to understand the importance of #3

As 21st century fathers we are in a double bind. We are suppose to be providers, making tons of money, and yet at the same time be hands-on dads. If feminism was born out of the desire of women to leave home and be treated equally in the workplace, giving rise to the Super Woman phenomenon in which women were supposed to be able to do it all, dads who have made their way back from the office, into the kitchen and the kids' playroom, are now faced with a similar Super Man challenge in which we are expected to do it all and are unable to do anything as well as we would like.

I know. I have lived it.

I'll give you the short version because it’s so long ago now that it feels like a different lifetime. And frankly it still hurts.

In early adulthood I fell into the version of manhood that was all about career. I had been a competitive rower in college and a hard drinker shortly thereafter. I went to business school and realized I was better than I ever expected at math and making people like me. By the time I was 30 I had become Chief Financial Officer of a large company that I took public and then sold 90 days later for $2 billion.

Only problem was that I had two baby children I barely knew.

The week after I announced the big deal -- the very thing I had thought would make me a real man -- my then-wife threw me out of the house. In a moment, I realized just how much my macho calculus had been wrong. All the money on the face of the planet wouldn't make up for losing those two kids. The idea of not living with my own children threw me into pain so profound I can only describe it as the tearing of my own flesh. It left a scar on my heart that even 15 years later has changed me forever.

When the deal closed I got a nice big check and was sent on my way, no longer needed or wanted by the acquiring company. For a year I lived in a furnished studio apartment that can only be described as depressing. I decided not to get another job but instead focus on spending what time I could with my kids and improving myself in the hopes of becoming a decent father.

A real turning point was that Christmas in 1996. I didn't see my kids, who were 1 and 3, because they were with their mom. December 28th I was in New York causing trouble with my friends. I woke up with the realization that I had to stop drinking and start taking a long, hard look at myself in the mirror.

It would be another two years before I went back to an office and anything resembling a real job. I spent that time learning how to take care of my two kids on my own with no back-up whatsoever. I went to a ton of "Mommy and Me" classes, went to the playground, changed diapers, and fed them bottles. They always seemed to vomit on my watch. I was constantly pushing them around the Back Bay of Boston in a double stroller.

I will always cherish that time, even though in many ways it was very challenging. Not many dads get that kind of total immersion crash course in the nuts and bolts of fathering. I came to realize there is no one right way. And in fact the "right" way is what is hardwired into the soul. For me and my kids, I eventually found what came naturally. We'd go to the top of the Hancock Tower or run around the Tower Records that was just around the corner because they became our favorite activities. We listened to Harry Potter tapes, when they got old enough, whenever we were on a long drive even though we pretty soon knew them by heart because it was soothing to each of our souls.

I developed my own cherished rituals with the kids. Bedtime was, and has always, been something I look forward to. It began with the simple feeding of a bottle to my then infant son in my bachelor pad for the first time. I inhaled his innocence and found myself in a way I never had before. No deal ever felt so good, never allowed me such a deep sense of peace.

After two years of not working I started my own venture capital firm. I made sure to put our office around the corner from the kids' school and playground. And I was greatly liberated by this little black pager looking box called a BlackBerry that allowed me freedom of movement while still being reachable. I kept up my weekday hours with the kids even though they were during normal working hours because everyone knew where I was and could reach me if necessary. And I more than made up for it with late night follow up once the kids were in bed.

After six years on my own I found the perfect woman for me and got remarried. On Valentine's Day, 2005 we had my third child. Cole is 11 years younger than his sister and 9 years younger than his brother.

One of the best parts of my 47 years has been the experience of raising Cole with my wife Elena from day one with none of the complexity that made my time with my big kids so challenging. Don’t get me wrong, I cherish every moment of solo parenting. But with Cole I was able to take all that I learned the hard way and just relax into the joy of fatherhood. And I got to watch Kerry and Seamus adore their little brother. Nothing could warm the heart more than that kind of unconditional love.

After my initial stumble with putting work before family, I have had my moments of getting dangerously close to the edge. Running a venture firm is not a small task, especially since most of our investments were made just after the Internet bubble burst. But my thinking was always informed by the idea that my kids come first no matter what. Yes, I am highly competitive and work very hard, even obsessively hard, at my career. But if my kids are suffering as a result I really don't give a crap. The career goes out the window.

In a counter-intuitive sense, I think this attitude about my work has been an advantage. It has meant that I don't view risk taking at work with the same kind of all-or-nothing fear that I often saw in my peers. They seemed to be so pre-occupied with getting their sense of identity and self-worth from financial success, that the very thought of failure often paralyzed them.

I had seen failure up close and personal, unfortunately, not in finance but in the eyes of my baby children. No lost deal or cratered start-up would ever be as bad as that. Not even close. So it liberated me to roll the dice where others might overthink an opportunity.

My very best investment of all time, a company called Art Technology Group, was one I stumbled upon during those first months of changing diapers and playing at the playground, when my heart was still in my throat most days, with the combined impact of getting sober and trying to learn how to be a dad on my own. I met a couple of MIT grads between "Mommy and Me" classes. A couple years later our collective company was worth over $5 billion.

I will never, ever value my career over my kids. But that doesn't mean I don’t enjoy a win just as much as the next guy.

We're partnering with The Good Men Project for Father's Day, and hearing from actual dads about topics that matter most to them. You can also head to our Dad Salary Wizard to find out how much dads are worth, and even print out a paycheck for yourself or the dads in your life!