Darrell Vesterfelt, a founder in the creator economy, talks about separating who you are from what you've done wrong. He discusses becoming a new father while running a business, and how that pressure reshaped his identity and relationships.
Darrell, how's it going today?
Good, man. Good to see you.
You as well. And I'm looking forward to today's chat because I know you so well and I know this is going to go to a place that I'm not familiar with in regards to your story. And for me, I'm already excited, but let's just level set here. Can you, can you introduce yourself to our, to our audience, please?
Yeah. I'm Darrell Vesterfeld, founder, entrepreneur. I have started several companies, currently own a handful. I've been in the creator economy space since before that was even a term. Since about 2004. My entire kind of professional career has existed in that space a little bit. So I've worked at companies like ConvertKit in the past and I've also worked with many, many high influence pro athletes, authors, podcasters, bloggers, whatever we want to call the medium of the time, specifically around how to monetize their audience. So I've been doing that for a long time.
Yeah, yeah, you started the whole trend here with the creator economy, so I dig that.
I don't think I started it well.
Either way, you're very instrumental in the growth. But how are things going these days?
Like, overall, good, man. My life's never been better. What I love about work and life is that everything's so integrated, so I feel like I have deeper friendships than I've ever had before. Work has been challenging and fun and rewarding like never before. And it's a fun game to play. I think it's the most fun game to play is, is how to improve your life and yourself and your relationships and your business. And so I just view all of it kind of as an infinite game. And the game is really fun right now. There's lots of challenging parts of it. There's lots of frustrating parts of it. That's part of the game, but it wouldn't be fun. I think maybe Warren Buffett said it once, like, if you just hit a golf ball and it went to the hole every single time you hit it, it just wouldn't be fun. Like, part of the fun is the contrast between the roughs and the bunkers and also the sweet shots that you just hit down the middle of the fairway. And so I'm just having fun playing the game right now. Not everything is perfect, but I'm having a lot of fun playing the game. More fun than ever, actually.
Yeah, I love that quote. I'm going to, I'm going to borrow that one from you, but. Okay, so now we're going to go off this cliff where you mentioned some of the rough parts of your journey. And that's what we want to focus on today. Not in a way to exploit you or just to, you know, be amazed at your comeback, but in a way that. That motivates other people to do the same if they're pushing through some tough challenges. So. So you're up. What is the most challenging part of your life, either either personally or professionally, that you feel comfortable sharing?
Yeah. So I want to talk about part of my career four years ago. That is, I haven't actually talked a lot about it with. I've never talked about it publicly. And even you and I have been friends for a couple of years now, and I haven't even talked to you about it before right now. But it's around the week that my daughter was born and kind of the subsequent months after that. At the time, I had two companies. We were actually splitting out into two different companies. And one of the companies that was splitting out, I brought in a co founder and then investors. And it was the first time I ever had investors in a company of mine before. And I just wasn't ready, man. I was. I was really probably mentally ready for it. Like, I could do all the things, but emotionally became a pretty challenging point. So the company went from zero to a million dollars of revenue in the first 12 months, which was really great for, you know, kind of a lean. A lean startup, like small investment, just small company. It did really well, really quickly. But the problem was I was spread way too thin across too many different things. And I also just wasn't mentally prepared for how hard being a dad for the first time was going to be. So there came a moment that I'm not proud of this at all, but there came a moment where, you know, we had to. My daughter was breached. And so we had to do a scheduled C section. And I was so far behind on projects that were supposed to be launching that I was like, asking Claire to push back the C section, the scheduled C section, so I could have another day or two before was even before Collins came, my daughter came. And I missed deadlines with these big projects. Lots of money was invested in them. I just like, came to a breaking point a little bit. I didn't get the things done I needed to get done. They weren't done to the quality that I wanted them. I had frustrated partners at work, I had frustrated partners at home. Partner at home. I wasn't able to be present. And it just kind of all hit in this break point, on top of it, like, first time ever having a baby, no sleep, and something like, you know, I didn't ever think I was going to be a dad. This was something that was kind of a surprise for us, and it was a really great surprise in the end. But I was also working through this, like, complete shift of my identity of, like, I thought I was going to be this person forever, and now all of a sudden, I'm this person, and there was a loss. And I don't think that anybody ever told me that there was a loss that you experience when you become a parent, because everybody's focused on all the positive sides of it. And so everybody's like, oh, it's so amazing. You're going to love your child so much, and positive, positive, positive, positive. And nobody ever gave me the freedom to say, it's okay to be sad that who you used to be is gone now. And so I was dealing with the guilt of feeling that it's like, I love my daughter, but I'm also really sad that who I used to be is gone. And there's a lot of grief around that. So I missed deadlines. Clients were pissed off at me. My partners were pissed off at me. At home, I was stressed out and not being a present dad and partner. And then I'm grieving really heavily, and I was asked to leave the company that I started fired, basically, and asked to leave the company that I started just so that those partners could save face with the clients that I had completely made huge mistakes on. And in the moment, it felt like these were potential, like, large, influential.
