Wade: Yes, let’s do it.

John: Yes. Wade is the CEO and co-founder of Zapier, a workflow automation and productivity software used by over a million people. He’s a Y Combinator alumni, avid racquetball player, and Missouri native. Wade, take a minute, fill in some gaps from that intro and give us just a little glimpse of your personal life.

Wade: I work on Zapier most of the time, I play a lot of racquetball, I hang out with my wife and dog, and, you know, that’s it. That fills the day for me.

John: Well, by the time people hear this, it’ll be said and done, but while we’re talking it’s the middle of March madness. So are you a Missouri fan?

Wade: Oh, I’m excited. We’re back in the dance for the first time in five years so it should be good. I’ve got it all cued up, ready to watch on Friday night they play.

John: Well, listen, if you got some time on Friday afternoon you can watch my team, Providence College, who’s in it for the fifth straight year, one of only 13 teams to do that by the way. Pretty awesome stuff. We’re gonna be playing Texas A&M at 12:15. So I’m pretty fired up for that.

Wade: That’ll be good. A&M’s got a good team.

John: So listen brother, we’re gonna talk about Zapier because as we’ve shared in the little pre-interview chat that we had, Zapier does make people happier. It’s just a reality. But first and foremost, what would you say today your area of expertise is?

Wade: At our stage, we have 140 people on the team. The thing that I’ve become better at, and perhaps even good at, is just learning quickly. Because as our org grows fast, you kind of have to reinvent what you do every six months or so. And so I’m constantly trying to learn new things, stay ahead of the curve just a little bit, get the right people around you, the right advisors and mentors and all that stuff to be able to learn fast enough. And as a result, I think we’ve built a pretty cool and useful and productive team over here at Zapier.

John: 140 people, that’s a massive team. I’m really impressed by it. I didn’t actually know it had grown to that number so that’s huge. Question that I would love to have you answer for us is, what’s something that’s surprised you while growing a team to 140 people? Something you maybe didn’t expect but now you’re like, wow, that could have been good to know.

Wade: If you’re an entrepreneur, or at least if you’re like me as an entrepreneur, a lot of times you get into the business because you wanna do your own thing, right? You wanna control your own destiny, your own direction; you wanna call your own shots, that sort of stuff. And you kind of assume that of the folks that you hire in and bring around you, so you kind of shirk off traditional management. You’re like no one wants a boss. That’s not super interesting to folks.

And so I kind of was slow to implement a more traditional management structure at Zapier, but I did a complete 180 on that. And now I’m like the next company I do, we’re gonna have traditional management pretty much from the get-go because it’s so valuable to helping your team level up, align on the direction that you’re going, and make sure that you’re all kind of heading towards the same goals.

John: So I guess basically the summation is if you could kind of do it all over again, you would have started implementing more of a traditional structure early on. What does that look like exactly? What is one step that you would have taken earlier that’s really helped you get to where you’re at now?

Wade: The most basic thing I would have done is weekly one-on-ones with every person on the team for just 30 minutes and just hey, how’s your week going, how’s life, how’s work treating you, just tell me what’s on your mind. I would have done that from the very get-go, even with our first employee.

John: Fire Nation, Paul Graham is famous for saying do things that don’t scale. And yes, we’re entrepreneurs, we wanna leverage, we wanna scale our faces off, but you have to do things that don’t scale if you are going to do things that eventually do scale. And let me just tell you, having those one-on-one conversations would have been absolutely revealing to Wade early on in his game. And I mean, that’s just one of the things where you can do those things that don’t scale at first, but then you learn things through those conversations, through those sessions, that you can then implement that’s gonna help you scale and leverage down that road. So don’t be afraid of doing things that don’t scale. I love that feedback, Wade.

Now, let’s go to your journey as an entrepreneur. I mean, you weren’t always rocking Zapier at 140 employees with over a million users. I mean, those are just massive numbers. And honestly, I’ll be surprised if anybody listening to this show hasn’t heard the word Zapier before. I mean, your branding’s been great, a lot of people use it. It’s kind of become that verb in a way where people say like Kleenex instead of tissue. You know, when people are trying to connect two different softwares they just say Zapier instead of anything else. You’ve done a great job with that, but what was the worst moment that you’ve experienced as an entrepreneur? Take us to that moment, tell us that story.

Wade: I think the thing that was toughest for me was in that very first year when we were starting Zapier, we were working crazy hours to be honest. It’s not something I would recommend for the long haul for most entrepreneurs to do that. We were working insane hours, we’d moved to California, my wife had come out, we were away from family. And I got a call from my mom one afternoon saying my dad had had a heart attack. And it turned out he didn’t make it. And I think that was a bit of a – just a smidge of a wake-up call for me. It’s like, you know, this business I’m working on is important, but the friends and the family that I have around me, these are the people that are gonna be with me until the end.

And so it was – it’s not that I was ignoring them or not spending time with them, things like that, but my priorities have shifted just a little bit toward Zapier. And I think it was a bit of a chance to step back and kind of realign and think about what my daily routine should look like and how I should spend my time and schedule my weeks to be more productive at work so that I could have the life that I wanted with my friends and family.

John: There are a couple things I wanna add to that because, Fire Nation, this is such an important topic on so many levels. No. 1, I actually, probably about three or four years ago had this incredibly realistic dream that my father passed away. And I mean, the dream was so real. It was one of those dreams like your emotions are so real that when you wake up for a minute it literally still happened. I remember one of my biggest regrets waking up and having that still feel real to me was that my dad was not gonna be able to continue to see the success of what I was building with my show because I know he was so proud of me and I was so proud to make him proud.
That dynamic was so important to me, but I didn’t really realize it until I had that dream and he died. And the first thought was oh my goodness, I don’t have him to “impress” and kind of drive me from behind the scenes right now. Does any of this even matter? I mean, that was kind of a dramatic thought that I went to, but that was my honest first thought. And it made me really think that wow, family is obviously so important. I knew that, but it made me kind of double down on that.

And another thing that was really interesting, I’m not sure if you’ve actually read this yet, Wade, but it’s a great article on Wait But Why, this website. And the author is Tim Urban. And he has this really, kind of just brutally honest article about how we live our lives and that by the time, essentially, you turn 25 or 30 years old, I don’t remember the exact age, but he graphs it out beautifully, you’ve already spent 90 percent of the time that you will ever spend with your parents. Like, it’s already in the past.

So if you’re listening to this and you’re 25 years old, you’ve already spent 90 percent of the time that you will ever spend with your parents. You only have another 10 percent left, meaning one to 18, most people, you’re seeing them every day, breakfast and you go to high school and all these different things. But that’s just such a slap in the face. It’s like wow, I literally have 10 percent of the time I’ve spent – of the 100 percent of time I’m going to spend with my parents in my lifetime, 90 percent of that’s gone.

And, you know, that’s made people like Tim Ferriss actually go back and start to plan vacations with his family and his parents now because he realizes hey, it’s gonna be over at some point. And it’s just a realization it’s better to make sooner than later. I’m going on a cruise with Kate’s parents and my parents this coming October in Rome. I mean, it’s these type of things that you just gotta get on the schedule, Fire Nation. You have to make it happen because you’re only gonna have regret if you don’t take the time now.

So, Wade, I kind of wanna move forward now and talk about your aha moment. You’ve had a lot of great aha moments. Actually, maybe I’m kind of curious. Maybe I’ll even try to directly ask you what was the aha moment for Zapier? How did that idea, which has now turned into a million users, 140 employees, how did that idea hit you? Where did it come from?

Wade: So my co-founder Bryan and I, we were doing a lot of freelancing back in Columbia, Missouri at the start – well, before Zapier. And we’d often get asked to build these one-off integrations. You know, we did a PayPal QuickBooks thing; we did a WordPress Salesforce thing. And Bryan messaged me on iChat one afternoon. He’s like, you know? I think we can make this thing that allows folks to set these types of integrations up on their own. They don’t have to hire engineers to make this stuff. I was like, you know, it makes some sense. Let’s see if we can get something going.

And so we started hacking around on it, but even then, when you have the initial idea, a lot of times you’re like – it’s a good idea, but you don’t feel it. Like is this really the thing that’s gonna be that – that’s gonna work really well? And so for me, the moment that tipped over to, like, holy crap, this is gonna work, was I had cold emailed Andrew Warner of Mixergy asking him about – he was on a forum asking for a PayPal Highrise integration. And so I messaged him and said hey, you still looking for a PayPal Highrise thing? If so, we might be able to help you out. If not, curious what you found. He’s like no, I’m not, but I really need this [inaudible] [00:10:16] thing.

So we built it out for him that night and I got on Skype, showed him how to use it. And it was bad, to be honest. The product was bad at that point in time. But at the end of that – at the end of chatting with him he was like oh my god, this is gonna help my business so much. How much money do I owe you? And I remember getting off that call and thinking holy cow, this product is not very good yet and he was so excited about this. You could just hear the energy in his voice. And I was like this is great. We have got something now. Because if we can actually make this product good, imagine the reaction then. And so that to me was like the tipping point of we have something here.

John: Fire Nation, the curse of knowledge is so real. When we as humans know something, we kind of assume that other people know those things, when the reality is probably 90 to 99 percent of people don’t, at least to the level that you know that thing. And when you’re really good at building out stuff or doing X, or doing Y, or doing the software and you don’t think it’s that good, well 99 percent of people might think it’s pretty good. And that should be an exciting thing for you to realize, hey, if they think it’s good at this level, what if I even step it up to the next level? I mean, this could really be something special.

So don’t have this curse of knowledge where just because you know something you just assume other people know it. Or just because you’re really good at something and you create a crappy product that other people might not think is actually kind of decent because they’re just not at that same level. I definitely remember when I was in law school hearing this fact that will always stay with me, is that a subject matter expert in a court of law is somebody who’s defined as they know more than other people in the room. You’re a subject matter expert if you know more than other people in the room.

So Fire Nation, what are you a subject matter expert on? Don’t take that lightly. So, Wade, that’s really my big takeaway from your aha moment. What do you want to make sure Fire Nation gets from that story?

Wade: You know, I think the thing on that is to relentlessly focus on who your customer is because like you said, you do have that curse of knowledge. So what you think is good or not good, your brain can’t realize that. So your customer is really the one who is the decider of that sort of stuff. So pay attention to what they say, listen to their feedback, get your offerings in front of them, and find ways to solve problems for them. They’ll guide you to where you need to go.

John: I think it is that combination, Fire Nation. It’s you having that curse of knowledge, No. 1, so don’t let that hold you back. And then just recognize hey, let me do things that don’t scale. This is the theme that we’re kind of concocting right here. Do things that don’t scale and don’t have that curse of knowledge by saying just because you assume that you know it or that it’s obvious knowledge, it just may not be for everybody else. So, Wade, let’s kind of move forward into something that you’re fired up about today. What really gets you out of bed in the morning?

Wade: You know, I think the thing that still gets me out of bed is just scaling Zapier. I’m still so excited about helping our customers and growing this team. We’re in a pretty rare position. We have 140 people, a distributed team, and there are just not that many companies that have done that. And so I’m really excited to be – continue scaling out this team and see where we can go and take this and prove some folks wrong that you can scale and build a really big distributed company.

John: Now you can’t have 30 minute chats with 140 employees every single week like you said you wish you had done back in the early days. So what do you do today to still stay connected with your audience? Or not even with your audience, with your employees?

Wade: Yeah, yeah. So I think the big thing is you have your management structure so all the people that report to me are doing those 30 minute one-on-ones and so you kind of get to hear secondhand a little bit about it. But I also make time for what’s called skip level one-on-one. So I’ll dip down a layer below me in the hierarchy and I’ll do 30 minute one-on-ones with those. We’ll do group sessions with a handful of folks to hear a little bit more from them about how things are going.

We do these things called pair chats at Zapier weekly where I randomly get paired up with one other person on the company and I just chat with them informally about how things are going, both personally and professionally. So I still carve out of my schedule on a weekly basis a couple hours to take time chatting to folks on the team who are not directly reporting to me.

John: Love those. Hope you employ both of those, Fire Nation, if you’re growing out a team. No. 1, if you’re super early, you just have a couple, have those 30 minute conversations. Believe me, Wade, myself, we guarantee they’ll be valuable. Then as your team grows to the point where that’s just not possible, implement some of these things that Wade’s talking about, you know, the skip levels and the pair chats and all these different things.

And if you think that Wade’s been dropping value bombs thus far, Fire Nation, you are correct. But guess what? More are coming up in the lightning round when we get back from thanking our sponsors. Wade, are you ready to rock the lightning round?

Wade: Let’s do it.

John: What was holding you back from becoming an entrepreneur?

Wade: I didn’t even know what entrepreneurship was, to be honest. Growing up, I grew up in a conservative Midwest town, there wasn’t really much information about that. The way that you had a successful life was you go to school, you study a good degree, you go get a job, you work for 40 years, you retire, and that’s a good life. And that definitely is a good life, no doubt, for many people. But for me, I didn’t know – I didn’t see anything else. And so having that opportunity to kind of discover entrepreneurship was a critical turning point for me in realizing that hey, entrepreneurship is much about learning the rules, but then also breaking them at the right time and saying hey, we can do things a little differently here and make something special.

John: What’s the best advice you’ve ever received?

Wade: The best time to plant a tree was a decade ago. The second best time is today. And so I think that still rings true to me where it’s like yeah, you can beat yourself up on all the things you shoulda, coulda, woulda done way back when, but you still have a lot of runway ahead of you. So yeah, you didn’t do it then, but let’s do it now and you can plant that tree and really, if you do it well and tend to it well, in five years, ten years you will have made something special.

John: What’s a personal habit that contributes to your success?

Wade: Racquetball is a really important routine. It helps keep me – I get exercise, it helps break up my days. You know, I’m stopping at work 5:30 every day heading to the gym. So it’s a really healthy routine that keeps me healthy and keeps me – keeps a bit of work/life balance in place for me.

John: Recommend one internet resource besides Zapier.

Wade: You know, a lot of these things I’ve been talking about today are management I picked up from this site Manager Tools. It’s a podcast that teaches you just the 101s of management. It gets really tactical, the words you should say, things like that. It doesn’t stay way high level in the fluffy clouds. It really gives you stuff that you can take and apply today.

John: Recommend one book and share why.

Wade: The book that changed my perception of entrepreneurship was Steve Blank’s Four Steps to the Epiphany. It really outlines the difference between entrepreneurship and a startup versus working in a company that has product market fit. So it really digs into the details and gives you kind of a tactical plan and a bit of a scientific approach to creating a product that people love.

John: Well, Fire Nation, if you’re not an Audible member you can get that book for free. Just visit eofirebook.com and you are on fire. And Wade, I wanna end today on fire with a parting piece of guidance from you, we’ll get the best way that we can connect with you, and then we’ll say goodbye.

Wade: Don’t hold yourself back. Get started today. If you see problems ahead of you, do things that don’t scale. Yeah, the best time to plant a tree was ten – a decade ago, but the second best time is now. So just if you see a thing that you should be tackling, go tackle it now. The best way to connect with me, two ways actually. I’m fairly active on Twitter, @WadeFoster, you can get me there. And also email’s great, wade@zapier.com. I may not respond immediately, but one to two days I’ll certainly be back to you.

John: Fire Nation, this is the founder of a 140 person company. This is a founder of a company that has a million users. He’s given you his email. If you have a question about something that you’re working on, take him up on this, wade@zapier.com. And, Fire Nation, you’re the average of the five people you spend the most time with. You’ve been hanging out with Wade and JLD today.

So keep up the heat and head over to eofire.com. Just type Wade in the search bar. His show notes page will pop up with everything that we’ve been talking about today. These are the best show notes in the biz, timestamps, links galore. And, Wade, I wanna thank you, brother, for sharing your journey with Fire Nation today. For that we salute you and we’ll catch you on the flipside.

Wade: Awesome. Thanks for having me.