Tom First on doing deals just before his rehearsal dinner; on crying when he first fired someone; and on why he wouldn’t change much in his past. 

Q:  What was it like, building a company and a family at the same time?

A:  It wasn’t really at the same time. I was really young—22—when we started Nantucket Nectars.  I didn’t get married until I was 29, and I was 35 when we sold the company.  During those years I was traveling like a maniac—forgot what city I was in, that kind of thing.

Q:  The company was growing fast at that point.  How did Kristan feel about your work mania?

A:  Kristan was in architecture school.  It was an odd time in our lives.  She was as obsessed with work as I was.  But even so, my preoccupation with work took some getting used to.  She grew up in LA, and we got married out there.  At that time, Nantucket Nectars was not doing well in LA, so I saw our wedding as a great opportunity to go out and meet with distributors.

She saw me for the first time at 4 pm the day the rehearsal dinner.  She said, You’ve got to be kidding me!  At the time, I didn’t get it.  I feel bad about it now.  I thought I was doing the right thing for everybody.  It bothered her, but there was an understanding that this is what I’m like.  At that point it was still a matter of survival. The company was growing exponentially, out of control.

Q:  Did having a child change things?

A:  Definitely.  It put the business in perspective. I was the most compulsive obsessive worker that I knew.  For the first time it became ridiculous to work 7 days a week.

Q:  And yet you started a couple more businesses.

A:  We lived in Cambridge for eight years before we moved to Concord, Massachusetts.  We had become dependent on the Cambridge Fresh Pond Market..  So I said to Kristan that we should open our own market in Concord.  She said, we don’t need to be opening more businesses!  But I got obsessed.  I wanted to understand retail.  I found a building, negotiated the whole deal, and got the liquor license, before I told her. We open a grocery store, Concord Provisions.

Q:  How did Kristan react?

A:  She rolled her eyes. She ended up being excited about it.  After the store was open, she looked at me one night and said, “You’re bored stiff, aren’t you.”  I had finished opening the store, but wasn’t running it.  She could tell that I was thinking about the next thing I was going to do.

Q:  She sounds like a saint.

A:  I’m not that bad.  It’s tough because there’s always something going on.  I always have something I’m excited about, obsessed about.  Most of my friends do things like market research.  That’s not me.  Kristen knows I’m crazy and she lives with it.  It’s a personality type.

Q:  Has this mode of being worked well for your personal life?

A:  For the most part.  One of my personality disorders is a high level of distraction.  Sometimes Kristan will tell me a long story that’s important to her, but other stuff comes into my head, and I get distracted.  It’s not that I don’t care.  But I am a multi-tasker.  At work I’m a juggler.  That kind of personality is not always so good at home.  I have trouble sometimes.

Q:  What advice would you give other young entrepreneurs with families?

A:  The biggest piece of advice is that any would-be entrepreneur should make sure the family is up for it.  I wonder if I could have started a business if I launched it as a married guy with kids.  I have started other businesses when I had kids but they weren’t complete start-ups. Kristan has always been a great cheerleader, making me feel good about what I was doing at a difficult time.

Q:  Looking back on your own life and business, what do you wish you’d known earlier on?  What do you wish had been different?

A:  I wouldn’t have changed anything.  For me, there’s been an experiential evolution that is necessary.  Your view of the world through the life of your family is dynamic and changes over time.  The same thing happens in a business.  So my vision, my fears, my level of understanding and my degree of patience evolved over time.  I fired someone for the first time when I was 25—I cried in front of them.  I wouldn’t say to someone new to business, “don’t’ have that emotion.”  It made me understand the situation so much better the second time.

You can’t tell someone, the first time the truck doesn’t show up, or that people steal stuff from you, you shouldn’t feel that the world is falling apart around you, because that’s how it feels the first time.  Those experiences changed the way I dealt with that stuff when it happened again.  I have perspective on business and life and family and relationship, more than I used to, because of what I’ve gone through.

Q:  Any advice?

A:  I would advise any entrepreneur to not neglect the personal side of their life.  I make time for my family, and I make time to work out.  I cook and do the dishes. I love being involved with everything.  But I’m never going to come home at five and turn off.  I’m incapable of that.

But there are times in a company’s life when there’s no way around the fact that you have to work all the time.  Kristan was lonely for long stretches during our early years together. But my partner Tom and I were on the label.  We had 150 distributors that wanted to be seen twice a year.  That makes 300 visits.  The only solution for the family is for the entrepreneur to be open with them and as present as he can be when he’s around.

Q:  How do you look back on those early years at Nantucket Nectars?

A:  We were so naïve.  Some of the stuff that happened—the chaos, always being on the precipice, the edge of a cliff, the lawsuits…. you’re a young guy and you think it’s over.  How do you say, I’m going home now because it’s 7:30 at night?

Now that I have kids, I feel bad about some of the things I thought back then, like laughing at people for commuting home all at the same time and dealing with horrendous traffic. Now I have much more sensitivity for the fact that people have families to get home to.