Ilana

How do you make sense out of it as a leader that on one hand, people tell you, you will not be fired if you're an IBM, but you will be fired if you're a startup coming in, right? And you screw up. So how do you balance it? You landed on the fun, authentic side.

How do you make sense out of it as a leader that on one hand, people tell you, you will not be fired if you're an IBM, but you will be fired if you're a startup coming in, right? And you screw up. So how do you balance it? You landed on the fun, authentic side.

And what I'm hearing also is your growth as a leader, right? From somebody, you know, right from the dorm rooms, basically in college, and suddenly running a 200 people team, et cetera, et cetera, multimillion, right? What do you feel helped you grow as a leader to be able with your money mindset, suddenly dealing with a lot of income and revenue, et cetera, debt sometimes, right?

And what I'm hearing also is your growth as a leader, right? From somebody, you know, right from the dorm rooms, basically in college, and suddenly running a 200 people team, et cetera, et cetera, multimillion, right? What do you feel helped you grow as a leader to be able with your money mindset, suddenly dealing with a lot of income and revenue, et cetera, debt sometimes, right?

Like what helped you grow there?

Like what helped you grow there?

What you just said, I had to write it down because that happens a lot in hiring. That happens a lot with different growths in different directions.

What you just said, I had to write it down because that happens a lot in hiring. That happens a lot with different growths in different directions.

Right? But as a leader, how do you balance between, on one hand, you want the chaos, you want the speed, you want the creativity, you want to let your teams get freedom. But on the other hand, you need to drive results and not throw spaghetti on the wall. How do you see it as a leader?

Right? But as a leader, how do you balance between, on one hand, you want the chaos, you want the speed, you want the creativity, you want to let your teams get freedom. But on the other hand, you need to drive results and not throw spaghetti on the wall. How do you see it as a leader?

Which I love because that's how you learn, right? That adaptability, that experimentation, you get the feedback really quick instead of, I still remember some of my enterprise companies that I was with, we had the requirements and nine months or 12 months later, something would chip and the requirements probably already changed. So I think that agility is really critical.

Which I love because that's how you learn, right? That adaptability, that experimentation, you get the feedback really quick instead of, I still remember some of my enterprise companies that I was with, we had the requirements and nine months or 12 months later, something would chip and the requirements probably already changed. So I think that agility is really critical.

Chris, could you share a hard moment? Because again, you're running this big thing for many years now. What was a hard moment that you needed to catch yourself?

Chris, could you share a hard moment? Because again, you're running this big thing for many years now. What was a hard moment that you needed to catch yourself?

Oh, my God. I mean, the roller coaster. How do you even get up in the morning and keep on going? What do you do?

Oh, my God. I mean, the roller coaster. How do you even get up in the morning and keep on going? What do you do?

First of all, you've been around for a while. You had an exit opportunity. You decided to decline, which is insane or not. But tell me what made you decide not to sell?

First of all, you've been around for a while. You had an exit opportunity. You decided to decline, which is insane or not. But tell me what made you decide not to sell?

That's incredible. And I think not only from the business side of you, but having that plan also, you started being very intentional about the life that you want to live together with this business. And can you share a little bit? Because I think that's super interesting.

That's incredible. And I think not only from the business side of you, but having that plan also, you started being very intentional about the life that you want to live together with this business. And can you share a little bit? Because I think that's super interesting.