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Episode 32: Interview with Natalie Nagele, CEO and Co-Founder of Wildbit

As the founder and CEO of a company serving over 100,000 people all over the world, Natalie shares the one thing she wish she would’ve learned earlier after 18 years running her company.

Every few weeks as part of The Heartbeat, I ask one question to a founder, CEO, or business owner I respect about their biggest leadership lesson learned. This week, I interview Natalie Nagele, CEO and Co-Founder of Wildbit.

Claire: Hi there. I’m Claire Lew and I’m the CEO of Know Your Team. On today’s edition of Heartbeat, I am so thrilled to have with me Natalie Nagele, who is the Co-Founder and CEO of Wildbit, which is this amazing software development company that has built this multi-million dollar products that are used by over 100,000 people all over the world. Natalie, you’ve been running this company for 18 years and counting with your husband, no less. It’s pretty much an entirely remote team. Just fascinating story. Most recently, Natalie’s company was featured in Fast Company for doing something pretty unconventional, which is having a four-day work week. Excited to hear a little bit more about that too.

But, the big thing I wanted to ask very selfishly, Natalie, was for you. In the 18 years plus running your business, what is the one thing you wish you would’ve known earlier as a leader?

Natalie: Wow. That’s a big question. Only one? I think-

Claire: We have all day. You can talk about as many as you’d like.

Natalie: I think, probably the one that’s really relevant right now is realizing that in order to truly lead, we have to have time to think and to really step back and work, as cliché as it is, on the business and not in the business.

You know that, that’s important. You read about how important that is. Everybody tells you how important it is. All your mentors do it, but you’re still a small business and you’re stuck in so much of the day to day.

I think, this year especially, Chris and I have started to explore how much more valuable we are to the company and to our team when we step outside and when we take breaks and think and strategize and how much more productive we are and just holistically for the entire organization when we do that. But I wish I did that sooner. I wish it wasn’t year 18 when we decided that, that was important. 

Claire: I hear you. It’s funny, I think, that you mentioned that it’s a cliché because hey, cliches are cliché for a reason. It’s because they often ring true and even hearing that answer, I go, “Oh, yes, in the four years running.” What was Know Your Company, now Know Your Team, anytime you can step back, it’s so invaluable. 

I’m curious, I mean, you’re saying like, “Okay, we kind of realized this in year 18.” I mean, what caused you to finally carve out the time? Was it something that happened? Was it something you read, something a mentor said? But what was the switch?

Natalie: I think it’s been brewing for awhile. We haven’t always run the business with intention. I mean, you start a company when you’re really young and you’re just, for a long time, just trying to pay the bills and get stuff done. I’d like to think we’re more entrepreneurs and business people, so we just to have an idea, want to run with it and that’s the purpose. There’s no real business plan or anything like that. 

I think, over the last couple of years, we’ve been starting to think a lot more like why. Why do we run this business? Why do we choose to be entrepreneurs? Why do we have these products? Just asking a lot of whys. Slowly, kind of maturing into understanding why we exist and what the purposes are and then, that work as important as it is, takes that stepping away time and I think one of the first times we made a really huge impact was when we sat down as a team and created values, written values. 

We always had a focus or a culture but written values, they’re important. Then said, “Oh wow, that’s pretty impactful. Cool. Okay. What else can we do?” Then, starting to understand those whys. I think, this year was the first year that Wildbit, we made some pretty big strategic changes. We sold a product. We are building a brand new product and did some pricing changes and that actually created the first year in Wildbit’s history that we weren’t as profitable as we normally are. Really not near my comfort level. Probably very comfortable for VC-backed companies but when you’re revenue-driven, it’s a very scary place to be.

Claire: Yes. 

Natalie: That forced Chris and I to spend a lot of time saying, “Okay, well now we’re running a business and these moments are okay but what are the strategic directions that we want to take it in?” Also, that you hit 18 years and I think Chris and I have been doing a lot of soul searching, saying, “What do we want to do in the next 10 years? Is this still a thing that we love to do and what we want it to look like.”

Also, that you hit 18 years and I think Chris and I have been doing a lot of soul searching, saying, “What do we want to do in the next 10 years? Is this still a thing that we love to do and what we want it to look like.”

But when you’re in the day to day, when you’re squashing email all day long or in meetings telling …

There was just this culmination of if I want to really enjoy my life and really live it with intention in this business which is mostly our lives,, then, I just have to find time to make bigger decisions around it. That means hiring leads, creating an org structurally, there’s all these things that come with it. Right?

Claire: Sure. 

Natalie: It’s becoming a grown up business. I wish we had done it sooner. I think there would be some less stressful years had we done it sooner. 

Claire: Sure. I mean, I think there’s a few things in what you shared there, Natalie, that I find absolutely fascinating. One is you allude to this idea that, well, taking time away from the business to actually focus on the strategic direction actually helps you optimize for happiness as a business owner. Do I even like doing this? Is this fun work if I’m doing this for 18 plus years or if I’m going to do this for the next 10 years. I think, for anyone who’s listening, I think, that’s an important thing to reflect on. This is, hypothetically, if you’re spending so much time on it, is supposed to be somewhat enjoyable and so, getting to take that time off helps you realize that. I think that’s one fascinating thing that you touched on. 

I think, the second thing is you allude to the fact that it would’ve been a lot less stressful. I mean, you were saying like maybe we would’ve been even more profitable had we done this earlier. Do you recommend for the managers, leaders, entrepreneurs, founders who are watching this, like, “Hey, take this time off to work on your business instead of in it so much earlier. Don’t wait the 18 years.”

Natalie: 100%. I think, I feel like the old lady in the room is like, “Back in my day,” but we didn’t have the understanding. I run SaaS businesses, right? We thought we were the coolest thing since sliced bread, and we reinvented business. Then now, we realize like, “No. Business is still business, and these people want to buy products,” and you talk about all those things that we now are like, “Oh, okay.”

That means that you have to have a strategic vision. You have to have an understanding of why you exist. You have to grow people and do all these things that only happen if you step up.

Your team kind of needs you to do that, right? There’s this other part, I think that there’s so much guilt around what if I took a day to walk around the city just to think. It’s like, “Well does that look like I’m slacking off?” No, because … Later, you find out your team’s like, “No. I want you to go think because I want you to come back and make sure that we’re on the right path.”

Claire: Right.

Natalie: “If you don’t go out and think, and you don’t come back and make sure we’re on the right path, then, Oh my God, what’s going to happen tomorrow?”

Claire: Right. 

Natalie: It’s been such an exciting adventure for us because it’s actually less hours of work, if that makes sense. I can come up with, given the space, intentional space, so we’ll go on retreats, and we’ll go up to the woods, and we’ll do all these intentional things to get away. Come back and build something or create something that will carry us for months. It’s less actual time.

You don’t need to make these grandiose decisions every single day, but you just need the space to be able to look from above and say, “All right, cool. Here’s where we want to go and well, if we changed this, then, maybe it’s going to have a big meaningful impact.”

Claire: Yes. 

Natalie: Years ago, had we done that, I probably wouldn’t have been in this year of low profits because I would’ve had a director of finance who would be like, “Hey, Natalie, if you do all these things at once, you might not be profitable this year.” 

Claire: Absolutely.

Natalie: I didn’t have a person because I was like, “Oh, it’s fine. I’ll do it all myself.”

Claire: No. I’m nodding. I’m nodding my head here being like, “Yes, I’m with you.” I think there’s so many CEOs and Founders that I’ve talked to, who’ve experienced something very similar, where when … You just don’t see things as clearly and it just sometimes takes that extra time of stepping away. 

I’m curious Natalie, just very tactically, what does this time of stepping away look like? I mean, yeah, do you take a day off and go walk in the woods? How do you structure this? Is it something you do every single year or that you’re going to start to do every single year? Just like practically, very tactically, what does this look like?

Natalie: Lately, it’s been very intentional. I’ve come to realize, I have to carve out the time. Usually, towards the end of the year, Chris and I will go away somewhere just for a couple days. There’s a place in the woods that we really like. That could be a thing. 

But what I’ve been doing, which I learned from a story about, I think, Carl Icahn, the finance guy. I’m not into the finance world but I kind of understand what he does. Anyway, there was a story that somebody was in a meeting with him and his assistant came in and said, “I have this big problem to solve.” He said, “Okay,” and he opens his calendar and he looks at it and says, “My next thinking day is Tuesday. I’ll add it to my next thinking day.”

Whether it’s true or not is irrelevant but what it created was this realization that you can have an intentional thinking time. There’s absolutely creative time. Like, “Oh, you spark an idea.” But you can also mull on a problem and kind of your peripheral and you can sit down and for me, it usually means writing.

I just start writing. I write outlines, I write perspectives. I’ll write the same thing in four different ways to see what it resonates with. I think, for me, it’s like, “We have to solve this problem. We’re moving into an organizational structure and doing a bunch of things and working on our operations.” 

Chris and I spent the last two months with really dedicated … Wednesday, no email and let’s solve this problem. Or we went to New York last week and spent a night and we’re like, “All right, we have these three things we want to tackle.” We had an agenda for ourselves, like, “These are the things we need to think about during this time away.”

Claire: Right.

Natalie: That’s worked really well for us because it gives my brain a single focus. Let’s tackle this.

Claire: Yes. 

Natalie: What we’re going to do in the future is we’re going to try to apply it to the team, so really want to have a point where we have strategic or specific moments for strategic decisions. Let’s have annual goals, let’s plan quarterly … Let’s dedicated weeks, everybody knows they’re coming up. We’re not mid-February changing direction and in December … Just give ourselves some space to think and then space to work and not interweave or whatever that too. 

Claire: The interweaving, yeah, is never, I think, as effective. I think that’s so helpful to think about. Actually, blocking out the thinking time on your calendar, I know there was a period last year where every Friday was sort of my big picture day as CEO, thinking about, “Okay, what are the big picture things,” and scheduling it out or I do this thing where no meetings on Mondays, right? Same thing. 

People have their own version of it. I know CEOs who will literally block out three days on their calendar and people are not allowed to schedule anything in there and they go and they have that time. I love the idea of applying that to your team and this idea to really foster that sense of protecting time and protecting your thinking time and assigning that time for your team. I know folks who are listening. Hopefully, they’ll be applying that as well. 

I guess my last … I can talk to you for hours here, Natalie. For the sake of time, the last thing I was curious about is for any Founder or Manager right now, who is like, “Okay. Natalie, this sounds great in theory, right? But in reality, I’m busy. Everything is on fire. I’m really worried about these key people leaving. I know what I need to do. I just need to go do do what I mean.” What would you say to them about them about the value of maybe taking a step back?

Natalie: I mean, I agree. There’s fires.

Claire: Of course.

Natalie: Some of that… I think those problems, like a key person leaving or these big decisions that you have to make, a lot of times in my experience, they’re a lot scarier when you’re in the business than when you take a step out. Take a key person, maybe not having a good situation with that, I think a solid reflection on the outside will show you that like, “What’s the worst case scenario? Can we replace them? What are the problems?” That actually creates that clarity and the thought that when you go back into it because you’re going to have to go back into it and deal with it, right? You’re not going to be able to stay up here and be like, “Oh, everything’s great.” You’re going to deal with it but you’re going to deal with it with a clear head and I think that is … You’re going to come up with a better outcome. 

I truly, from our experience, know that if I don’t step away when there’s a lot of stress, then I will just react in ways that aren’t level … clear-minded and then, I’ll come back to it three months later but that was a really bad decision, like, “We should have not have reacted that way.” 

I don’t know. I mean, it’s hard, but even just an hour to just close it and just, I like to do all the negative questions. What’s the worst thing that happens? What happens next? Walkthrough a scenario and it’s almost never the end of the world. Once that feels so less heavy. Here’s my options. 

Claire: Absolutely. No, I think, decision making always improves when you can remove yourself from reactivity and actually then, make a deliberate decision and respond instead of just knee-jerk, “Okay, I’m just going to sort of go whichever way the wind is pushing me.” You only get that if you take a step back. I also love the recommendation. Even an hour, over lunch, whatever, if it’s 30 minutes even, even to remove yourself back from the situation. Thank you so much Natalie. I so appreciate your wisdom and I know everyone else who’s listening does, too. 

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.