Brad Feld: Life With an Entrepreneur

The last thing on this thread that I want to give you is this notion of living your life. I hear this over and over again. I talk a lot about work, life, balance. I've had my own issues understanding this when I was 35. So a decade ago, this is 2002. Ish. Maybe 2001. In that time frame, let's say 2001, Amy and I were going to spend a long weekend together with some friends in Rhode island, and we met up in Boston. I don't remember where I flew from. I don't remember where she was. We drove down to Rhode Island. I was on the phone all the way down, talking about trying to save some company that was going to fail. Anyway, we get to our friend's house, and I'm still working. It's Friday night. We're drinking a little bit, but I'm still working on something or talking on the phone or some such nonsense. We finally go out to dinner, and my phone rings in the middle of dinner, and I get up and I leave. And, you know, you come back. At least I'm smart enough to leave the table and go outside the restaurant. I come back and they're done with dessert, right? So, like, it's over. Dinner's over. We go back to the room, to our friend's house, and, you know, we hang around for a little while. Later, we get in bed. And for those of you that are involved with somebody, you know, if you get into bed, you almost always immediately know if there's something wrong, and you could just sense it. And, you know, I was sort of laying there, and she says to me, I'm done. And I said, yeah, this was a tough week. I'm tired. It's really been a schlep, man. So much shit going on. And she says, no, no, no, you don't understand. You're not even a good roommate anymore. And I said, what do you mean? She says, I'm not angry at you. I love you. I think you're awesome, but I'm just done. I don't want to live. And I said, timeout. Not interesting to me. Let's not go here. It's Friday night. She's like, no, no, really, this is not working. And an hour later of that conversation that I think probably many people have had, we're sort of back to, let's spend the weekend and let's really talk about it. The ledge is here. You're no longer on the ledge. And in that moment where there's only certain moments in time where you can do this and get away with this. But just as we're falling asleep, I nudge her and I say, so I guess that means I'm not getting any tonight, huh? And to her credit, she laughed and it was perfect. I didn't get any, but she laughed. And I knew that I wasn't on the edge anymore. Like, I knew that we could actually have a rational conversation. So we spent the weekend talking about it. I gave her my phone and I said, let's look, I've got an engineer's brain. Give me some rules. Oh, that's not romantic, that's stupid. Let's just try it. It couldn't be worse. Like, you told me I was a shitty roommate. It couldn't be worse. Let's just try it. And we ended up with a series of rules. An example of some of the rules. We go away every quarter for a week. No phone, no email. So we call it our quarterly vacation off the grid. And I've now been doing it for over a decade. And the first two years of it, the first eight or ten times were awful. Total traumatic experience to just disconnect for a week. And now I just, I look forward to stepping onto the airplane, giving her my iPhone and getting it back in a week. And, you know, my assistant knows how to find me, my partners know how to find me if it's an emergency. And they decide there's no emergency that they could possibly want to bother me for. So I'm never bothered. It's wonderful. Another is we have something we call Life Dinner. So the first night of every month, we go out together. Not on a date. We have plenty of dates, we have plenty of going out to dinners. But we had this very specific dinner on the first night. And I said to her, as we were defining this, and I said, well, first night every month, I can probably commit to that. That probably works. She says, don't you use a calendar, online calendar? Very sarcastically? And I said, yeah. And she says, don't they make these things called repeating appointments? Yeah. She says, why don't you make a repeating appointment from 6 to 10pm on the first day of the month from now until forever. So we have a series of things like that. And on Life Dinner, we talk about the previous month and the next month. That's the agenda for the dinner. And it could be a two minute long conversation, or it could be a three hour long conversation. It could be wide ranging, it could be about a specific thing. But we've used that as sort of rhythm in our relationship. Now the reason I'm telling you these stories around this is that part of what was important to me at this moment in time was I was involved with this person that was more important to me than anything else I was doing, but who also respected and valued my level of commitment to the things that I did as an entrepreneur and as an investor, and the way that I wanted to live my life, and I respect the way she wants to live her life, but the intersection of that was important. We had to understand what that meant in the context of living our lives and me personally living my life.