This week, Jason Fried, CEO and Co-Founder of Basecamp and I, your host, Claire Lew, CEO of Know Your Team, interview each other for this special milestone episode #50 of The Heartbeat. We talk about learning how to be like yourself earlier, thinking about long-term views as leaders, how leadership roles change over time, and letting ideas go when you have to. Have you been enjoying these Heartbeat episodes, lately? If so, it’d mean the world to me if you wrote us a review in iTunes. The more reviews we have, the more we’re able to share all our lessons from leaders. Thank you! CLAIRE: Hey everyone, I’m Claire Lew and I’m the CEO of Know Your Team. Today is a super special day because on The Heartbeat, we have the one and only Jason Fried, who is the Co-founder and CEO of Basecamp, a project management tool that if you’re not using, I don’t really know what you’re using, is what we base our entire business off of. And for those of you who’ve been following Know Your Team, we were a spin-off company of Basecamp as well. But I wanted to actually ask Jason to come back on the show because Jason was the very first person I interviewed for The Heartbeat when I started this series two and a half years ago, when I look back. And today is a particularly special episode because it is the 50th episode that I’ve done of these, interviewing all sorts of leaders that I’ve admired all over the world. And I thought Jason, for this particular one, Jason and I talk regularly. He sits on our board at Know Your Team that you would be possibly the best person to maybe flip the tables this time around and ask me the one question that I’ve been asking leaders over the past two and half years on this podcast. So, I thought that’s how we would kick things off and then I have a bunch of questions for you because there’s so much to hear. Should we start there? JASON: Yeah, this is great. First of all, thanks for having me on. It’s an honor to be on the 50th episode and to be chosen to ask you this very special question which is basically as you start off all your interviews, you always ask, what’s one thing you wished that you’d known earlier about being a leader? So, let’s turn the tables and ask you the same question. What do you wish you knew, let’s call it, 10 years ago? CLAIRE: It’s so funny. I’ve literally asked this question likely more than 50 times and maybe in the best form. You try not to think of your own answer to the question that you ask. And I even knew that we were doing this episode. So, it’s funny, it’s like I didn’t really prepare for it. I’ll just share the first thing that comes to mind, which is: I really wish I had learned to be more like myself earlier, which is probably some leadership poster cliche thing that’s written everywhere. Be more like yourself or trust yourself. But I just have noticed that when I was first starting out, and I mean, you’ve known me for a while before I was even running Know Your Team and getting started. And I think one of the hardest things when you’re even just leading yourself, so before I even had a team is figuring out, “What do I believe in? What do I care about? And how true do I actually even stay aligned to that?” And I think the first instinct when you’re trying to answer those questions when you’re starting out is you pattern match and you go, “Oh, I’m really a big fan of the stuff that Basecamp does. I’ll talk to Jason and David and you hear about how they run their teams and how they work with people.” Or maybe I’ll talk to some professors or I’ll talk to other mentors or people who are older than me and wiser and making lots of money. This just seems like this would be the right path. And I would try those things and who’s to say to what d