Balancing Life & Running a Startup with Kevin Ryan

Speaker 1: Welcome to The Daily Bolster. Each day, we welcome transformational executives to share their real- world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, Co- founder and CEO of Bolster. And I'm here today with my friend Kevin Ryan. Kevin is the founder and CEO of AlleyCorp, and by extension, the founder of some of the most storied internet companies in the history of New York since the beginning of the internet, MongoDB, Gilt Groupe, Insider. Of course, Kevin was also CEO of DoubleClick, the company that really kind of gave birth to the New York tech, or at least ad tech scene. Kevin, great to see you.

Kevin Ryan: Happy to be here.

Matt Blumberg: So one of my favorite sayings of yours that I think I heard from you 20 years ago that I grabbed onto and repeat often is when you're talking to a founder, giving a founder advice about sort of managing their life and the insanity of running a startup is, " You can do anything you want, you just can't do everything you want." And I would love for you to just run with that.

Kevin Ryan: Yeah, no, absolutely. And I think it's an approach to life that you have to have a longer- term perspective so that, today, you can't just learn Spanish and run a startup and be a great father and stay in shape and follow the Knicks and do all these things. You're going to have to make trade- offs, and most people are not really willing to make those trade- offs and realize that 20 years from now, you'll be in a different phase of life and you can pick some of them back up. But it's better to do three of them really well than seven of them really badly. And so, when I started DoubleClick, I had young kids. Company got very big very quickly. So two, three years in, we had a thousand employees and 2000 employees after four years in 25 countries. So that's a lot to manage. And so, I decided to do three things, I wanted to be a good father and spend time with the kids, be a good CEO, and stay in shape. But the true sacrifices, I cut out probably 75% of the time I was spending with friends, which no one likes to do. 80% of the time, I was watching sports, which I also kind of like to do. Probably 90% of the time, I was going to cultural events, cool things in Brooklyn, museums, gallery openings, all gone. And now, by the way, 25 years later, I can do a lot of those things because I don't have kids at home anymore, I have more flexibility. So, just people need to make those trade- offs.

Matt Blumberg: Yeah, it is so important to do something outside of work, work, work because you can get sucked into that. And I think you're right, I think you can do one thing really well or two things really well outside of work. And I think that the challenging thing is probably for single founders, right? Once you're married and you have kids, one of your other things has to be that.

Kevin Ryan: Yeah. Although, not everyone does it. I mean, there are many, many people who have startups that look back and think, " I didn't see my kids."

Matt Blumberg: Yeah, that's probably true, but I think when you're a single founder, it's more sort of world of infinite choices and how do you skinny things down. So you can go take tango lessons, but you can only do so many things like that.

Kevin Ryan: Exactly.

Matt Blumberg: All right, Kevin Ryan, thank you so much for being here.

Kevin Ryan: Thanks.