The Exchanges

Q those meetings. When we think about, like, the decisions and the outcomes of those meetings, then they're communicated throughout the team, and transparency is crucial, especially in remote teams more so than ever. When we think about, like, specific tooling, Jay Simons asked this one. He asked, what specific tools do you use to be as transparent as possible, and how do you communicate inside the company, specifically on communication?

A Yeah, I mean, the sort of big company comm stuff tends to go through two channels. We've built this tool, Async, internally, that is like a I mean, the best way to describe it is kind of like a Reddit style, but long form Reddit, I guess, where you can post blog posts and assign them, like, into a category or, like, maybe subreddit if you want to, and then, you know, people can sort of like and comment on those things, and, you know, stuff that gets, like, a certain amount of activity goes to, like, the homepage, and so the homepage is kind of where things are buzzing about, and then otherwise people create these little feeds that help them get insight into their, like, Personal world view of Zapier. So if you're an engineer, it's like, okay, I care about these engineering topics, and maybe, like, this specific product team is, like, adjacent to me, so I care about their stuff, and then maybe I'm going to subscribe to Wade and maybe the VP of engineering, so I'm going to see everything that they see. So you kind of can craft your own little, like, homepage experience that is specific to you. And so that is, like, the sort of main, like, company comms, external stuff. Then a lot of the more just, like, tactical nitty-gritty, like, day-to-day work just happens inside of Slack. So we have tons of channels and That are in Slack. They follow a naming convention, and you'll find peop…

AI assessment note: “company comm stuff tends to go through two channels. We've built this tool, Async”

Q those meetings. When we think about, like, the decisions and the outcomes of those meetings, then they're communicated throughout the team, and transparency is crucial, especially in remote teams more so than ever. When we think about, like, specific tooling, Jay Simons asked this one. He asked, what specific tools do you use to be as transparent as possible, and how do you communicate inside the company, specifically on communication?

A Yeah, I mean, the sort of big company comm stuff tends to go through two channels. We've built this tool, Async, internally, that is like a I mean, the best way to describe it is kind of like a Reddit style, but long form Reddit, I guess, where you can post blog posts and assign them, like, into a category or, like, maybe subreddit if you want to, and then, you know, people can sort of like and comment on those things, and, you know, stuff that gets, like, a certain amount of activity goes to, like, the homepage, and so the homepage is kind of where things are buzzing about, and then otherwise people create these little feeds that help them get insight into their, like, Personal world view of Zapier. So if you're an engineer, it's like, okay, I care about these engineering topics, and maybe, like, this specific product team is, like, adjacent to me, so I care about their stuff, and then maybe I'm going to subscribe to Wade and maybe the VP of engineering, so I'm going to see everything that they see. So you kind of can craft your own little, like, homepage experience that is specific to you. And so that is, like, the sort of main, like, company comms, external stuff. Then a lot of the more just, like, tactical nitty-gritty, like, day-to-day work just happens inside of Slack. So we have tons of channels and That are in Slack. They follow a naming convention, and you'll find peop…

AI assessment note: “We've built this tool, Async, internally... tactical nitty-gritty... happens inside of Slack.”

Q Totally with you. Final one for the funding discussion, which I'm excited for, naturally as a VC. But, uh, I, I do have to ask you, you mentioned, like, the soul of the earth, the pull your socks up. I'm a big believer in also, like, vulnerability too within organizations. How do you think about vulnerability for yourself as a leader?

A Well, I tend to think that it is pretty useful to just be honest about, like, the situations you're in. I think that there's this sort of, like, old school mentality where, People are like, I'm the leader. I can't, I have to be perfect. You know, I have to have all the answers. I have to get it right. A hundred percent of the time, or else I'll be letting my team down or look weak in front of them. I actually think that that prevents a lot of good things from happening inside of your company. And so I think the more that you can sort of get comfortable sharing, like the full extent of the problem now, sometimes for a variety of reasons, you can't be a hundred percent transparent, but to the extent you can say, Hey, this is what we're up against. This is what we're dealing with. This is what we're trying to solve. It just gets everybody more aligned in, like, what we're trying to achieve and what we gotta do, and it helps people understand and relate. When you talk about vulnerability, like, to me, that's the trick, is it's about saying, this is what the problem looks like, a hundred percent, this is the part that I'm excited about, this is the part I'm worried about, this is the part that, like, I just don't know how we're gonna get this done, and it gives everybody the ability to sort of use their whole brain, I guess, on solving the problem, rather than, like, hiding this thi…

AI assessment note: “When you talk about vulnerability, like, to me, that's the trick”

Q It's not zero, but it's freaking low. And my point is, like, there's the trade-off of time, and, like, actually minimal dilution now, where, like, it's not 25% of old. It's 10%. It's eight percent. I mean, strike raised 600 at 95. I mean, the dilution is nil. So, I guess my question is, does your thoughts change at all when the cost of capital is so low?

A You know, it still comes back to, like, what are you going to do with that capital? What do you need it for? How are you going to spend it? If you have a good answer for it, yes, right now, the cost of capital is incredibly cheap, especially if you're a good company. I think it's different if you're a struggling company, but if you're doing really well, it is a really good time compared to most to raise money. However, the entire existence of my company, like, the markets have only gotten better and better and better, and I'm not saying that's going to be always the case, but, like, I've heard that every single year that this company has been in existence. Each time it just gets better and better, and the options for raising capital and options for taking on debt or taking other instruments to fund your company have gotten more and more diverse. So just come back to, like, do you want it or not? You know, I think, eh, just so you have it is kind of a weak argument, and I think if you have a good balance sheet already, you know, if your balance sheet is sufficient for your goals, why do you need 10 extra balance sheet? Why do you need a hundred extra balance sheet? So, like, just get really clear about what it is you want to achieve and what do you want to go do, because that equity is I guarantee you, if you're a good company, that equity is going to be worth so much more down …

AI assessment note: “it still comes back to, like, what are you going to do with that capital?”

Q Man, I've got to ask you a couple of things. Do you agree, and I, I oscillate between the two here, do you agree with the fake it till you make it? You know, you didn't know anything about marketing, really. Like, do you agree with the fake it till you make it theory?

A I think one of the things that I know about myself is that I'm a pretty good learner. Like, I've always been able to sort of pick up on things pretty quickly, and so I generally try not to fake it in areas where I know I'm, like, woefully inadequate, but in areas where I'm like, you know, I, I think I have a, a knack for this, I generally will sort of, like, say yes to those opportunities, and then, like, no, I'm gonna have to, like, dive in and learn a bunch of stuff out the gate and get going on it, and that's sort of served me well. I think, you know, anyone that's built a company of any size realizes that, like, you're gonna have to be in this sort of state of perpetual learning and constant learning, because, you know, as you keep growing, you're gonna find out there's just yet another thing that you're not good at and don't know anything about, so I do think there is some truth to it. I wouldn't, I guess, encourage people to fake being a doctor if they're not a doctor or something like that, But I do think, like, if you are good at learning things, and like, have an appetite, and are curious about a thing, like, go ahead and say yes to a stretch opportunity here or there.

AI assessment note: “so I do think there is some truth to it.”

Q me, hey, I don't know what I should do. Should I join a big company and learn from a big company organization like a Stripe or Zapier? Should I join a startup and really just do everything jack of all trades, or should I just dive in and start my own? How do you advise, I know it's generic, but how do you advise graduates when they ask you that?

A Well, if you want to learn how to run a company, I think the smaller company you can be a part of, the better, because you're just going to get exposed to, like, the whole of the thing. Because, you know, for me in that org, like, I got to be a part of product management, I got to be a part of building features, I got to Be a part of running payroll. I got to be a part of hiring. I got to be a part of marketing. I got to be a part of sales and business development, and like, we even wrote grants for the government to try and raise funds. So like, all these different things, like, I got to be a part of them. Now, we weren't necessarily great at all those things, and in fact, that's perhaps why the company wasn't an amazing thing, but I got to experience it all. I knew coming out of it, I just had my worldview had been opened much wider than it was going in, and so I knew going into any company I would have ever started, I was like, here's what all the pieces are. I may not be an expert at any one of these things, but I know what all the pieces are, whereas I think if you go to any sort of, like, post-product market fit company, you generally get slotted into, like, a role, and I think a sufficiently ambitious, smart person can still find ways to learn and have that sort of impact, but it's just not going to be there as naturally, I guess.

AI assessment note: “if you want to learn how to run a company, I think the smaller company”

Q Okay, so let's unpack that a little bit, because I also spoke to our mutual friend Shashir at Coda, and he said when it comes to staff meetings, often, you know, it's the core of a lot of kind of organizational infrastructure. How do you specifically run your staff meetings today? How do you determine who comes, the materials, the content?

A Yeah, you know, at Zapier, we, like, the exec team has a staff meeting every week. There's a prompt ahead of time that tees up the topics, and so people sort of pre-fill out their documents and Folks join a Zoom for the meeting. We do 10 minutes of pre-read. We're in a Google Doc, so everyone's, like, commenting out to the right, and a lot of small stuff sort of just gets cleaned up in that 1:10 minutes, where it's like, you know, someone from engineering had this thing with someone in marketing, and they're like, okay, we should do XYZ, and so, like, we never have to, like, talk aloud about those issues, because they just sort of get taken care of in the comments section. Then, for, like, the rest of the 50 minutes of the exec team, there's usually two or three, like, major topics. Maybe it's, like, A really key decision. Maybe there's like a strategic thing that we're trying to deal with. Maybe there's like a cultural issue that we're trying to address. Like it can sort of span a few different areas, but then we sort of designate the rest of that 50 minutes to one of those big topics. And it's usually just one or two topics that get like the lion's share of the discussion in a given week. And then anything that sort of falls below that line goes back into Slack as an asynchronous discussion after the meeting. So it's like, hey, we didn't get to this thing. Talk about it here …

AI assessment note: “exec team has a staff meeting every week. There's a prompt ahead of time”

Q Okay, so over 400 people. Can I ask, where were the biggest break points in the scaling of the org?

A You know, I think we have, Had break points at a few spots. I remember the first one was probably around 20 or 25. Like, that was where it was like, oh my god, there's no, like, management structure in this company, and we needed to, like, instill sort of proper management best practices, and so that was, like, a big step function. And I remember, like, somewhere between, like, a hundred, 125 or so, kind of like the dumb bars number, where it was like, oh man, like, I don't know everybody super well anymore. Like, I know a lot of people, but not all folks really well. And like, you started to have some of those people who were your first managers started to realize like, oh, managing like really big groups of people is its own skillset and started to have some challenges around that. So you started to bring in like a new set of executive leaders. And, you know, I think that spanned us pretty well, like one 50 or 200 to about where we're at today, 400. I feel like we're kind of at starting to get to a little bit of another inflection point where we're sort of having to reset some of how our operating cadence works. Like, how our management structure works yet again. So, like, I'd say 30, a 103 hundred kind of seem to be, like, the few points, I guess, for us of operational up-leveling.

AI assessment note: “Had break points at a few spots. I remember the first one was probably around 20 or 25”

Q Speaking of kind of the vulnerability around the decisions one makes, the other thing that I do have to ask while I have the chance is, like, you know, decision making is a passion point of mine. How do you think about head versus heart when decision making, and also, what do you do when you just don't know?

A I think for head decisions, like, when you're trying to figure out, like, what's going to generate the most customer happiness, or what's going to be, you know, the right products to go into, or the right markets to go into, you generally, like, want to follow, like, your head. You want to do your assessment and, like, dig in and, like, Understand what works, what doesn't work. When it comes down to sort of things that are more like moral or ethical or like personal, I guess, you know, there's an aspect of like, you gotta just stay true to who you are and to yourself. The times where I find myself using my heart the most are times when you sort of come to this crossroads where you're at a decision where you're like, I just don't know what the answer is, but I have this like gut instinct or belief that this is right. And I have always found that when I don't go with my gut, I regret it in those instances. I want to be able to wake up at the end of the day and say, you know, I felt this way, I tried it this way, and if it didn't work, well, at least I did what I believed in. When I haven't done that, I'm like, what if I would have done it the way that I thought originally? Like, I always have that question mark in the back of my head, so I generally, I guess, come back to the heart in those types of situations.

AI assessment note: “I just don't know what the answer is, but I have this like gut instinct”

Q it means for you to be able to invest that back in the business, not in fundraising, but, you know, when I spoke to Jay before, he did say that you kept and maintained great relationships with ECs despite never raising primary, uh, or not raising it for a long time. So, How did you approach the relationship building process with VCs, and what did that look like for you?

A Yeah, so, you know, I think despite what you've heard me say here on this podcast, like, I did say, like, hey, I do want an option. I do want to be in this situation where if I do say yes, hey, more funds would be better, like, being able to take on more capital would be a creative disaster. I did want to be in a position where we could do that quickly, and so I just sort of set up a, like, simple calendar where I said, you know, hey, One Friday, every quarter, I'm gonna, like, go snag lunch with somebody, or I'm gonna jump on a Zoom call with somebody, and build a relationship with five or six people that I think are smart, talented, maybe potential partners, and such that, if that day comes, I don't have to go through this shotgun wedding to raise money. I can know that if I'm looking for a partner in a business, this is a person that I already know that I want to do it, and they're willing to cut me a check on the spot.

AI assessment note: “set up a, like, simple calendar where I said, you know, hey, One Friday, every quarter”

Q Man, I've got to ask you a couple of things. Do you agree, and I, I oscillate between the two here, do you agree with the fake it till you make it? You know, you didn't know anything about marketing, really. Like, do you agree with the fake it till you make it theory?

A I think one of the things that I know about myself is that I'm a pretty good learner. Like, I've always been able to sort of pick up on things pretty quickly, and so I generally try not to fake it in areas where I know I'm, like, woefully inadequate, but in areas where I'm like, you know, I, I think I have a, a knack for this, I generally will sort of, like, say yes to those opportunities, and then, like, no, I'm gonna have to, like, dive in and learn a bunch of stuff out the gate and get going on it, and that's sort of served me well. I think, you know, anyone that's built a company of any size realizes that, like, you're gonna have to be in this sort of state of perpetual learning and constant learning, because, you know, as you keep growing, you're gonna find out there's just yet another thing that you're not good at and don't know anything about, so I do think there is some truth to it. I wouldn't, I guess, encourage people to fake being a doctor if they're not a doctor or something like that, But I do think, like, if you are good at learning things, and like, have an appetite, and are curious about a thing, like, go ahead and say yes to a stretch opportunity here or there.

AI assessment note: “so I do think there is some truth to it.”

Q Okay, so over 400 people. Can I ask, where were the biggest break points in the scaling of the org?

A You know, I think we have, Had break points at a few spots. I remember the first one was probably around 20 or 25. Like, that was where it was like, oh my god, there's no, like, management structure in this company, and we needed to, like, instill sort of proper management best practices, and so that was, like, a big step function. And I remember, like, somewhere between, like, a hundred, 125 or so, kind of like the dumb bars number, where it was like, oh man, like, I don't know everybody super well anymore. Like, I know a lot of people, but not all folks really well. And like, you started to have some of those people who were your first managers started to realize like, oh, managing like really big groups of people is its own skillset and started to have some challenges around that. So you started to bring in like a new set of executive leaders. And, you know, I think that spanned us pretty well, like one 50 or 200 to about where we're at today, 400. I feel like we're kind of at starting to get to a little bit of another inflection point where we're sort of having to reset some of how our operating cadence works. Like, how our management structure works yet again. So, like, I'd say 30, a 103 hundred kind of seem to be, like, the few points, I guess, for us of operational up-leveling.

AI assessment note: “I'd say 30, a 103 hundred kind of seem to be, like, the few points”

Q Speaking of kind of the vulnerability around the decisions one makes, the other thing that I do have to ask while I have the chance is, like, you know, decision making is a passion point of mine. How do you think about head versus heart when decision making, and also, what do you do when you just don't know?

A I think for head decisions, like, when you're trying to figure out, like, what's going to generate the most customer happiness, or what's going to be, you know, the right products to go into, or the right markets to go into, you generally, like, want to follow, like, your head. You want to do your assessment and, like, dig in and, like, Understand what works, what doesn't work. When it comes down to sort of things that are more like moral or ethical or like personal, I guess, you know, there's an aspect of like, you gotta just stay true to who you are and to yourself. The times where I find myself using my heart the most are times when you sort of come to this crossroads where you're at a decision where you're like, I just don't know what the answer is, but I have this like gut instinct or belief that this is right. And I have always found that when I don't go with my gut, I regret it in those instances. I want to be able to wake up at the end of the day and say, you know, I felt this way, I tried it this way, and if it didn't work, well, at least I did what I believed in. When I haven't done that, I'm like, what if I would have done it the way that I thought originally? Like, I always have that question mark in the back of my head, so I generally, I guess, come back to the heart in those types of situations.

AI assessment note: “The times where I find myself using my heart the most are times”

Q It's not zero, but it's freaking low. And my point is, like, there's the trade-off of time, and, like, actually minimal dilution now, where, like, it's not 25% of old. It's 10%. It's eight percent. I mean, strike raised 600 at 95. I mean, the dilution is nil. So, I guess my question is, does your thoughts change at all when the cost of capital is so low?

A You know, it still comes back to, like, what are you going to do with that capital? What do you need it for? How are you going to spend it? If you have a good answer for it, yes, right now, the cost of capital is incredibly cheap, especially if you're a good company. I think it's different if you're a struggling company, but if you're doing really well, it is a really good time compared to most to raise money. However, the entire existence of my company, like, the markets have only gotten better and better and better, and I'm not saying that's going to be always the case, but, like, I've heard that every single year that this company has been in existence. Each time it just gets better and better, and the options for raising capital and options for taking on debt or taking other instruments to fund your company have gotten more and more diverse. So just come back to, like, do you want it or not? You know, I think, eh, just so you have it is kind of a weak argument, and I think if you have a good balance sheet already, you know, if your balance sheet is sufficient for your goals, why do you need 10 extra balance sheet? Why do you need a hundred extra balance sheet? So, like, just get really clear about what it is you want to achieve and what do you want to go do, because that equity is I guarantee you, if you're a good company, that equity is going to be worth so much more down …

AI assessment note: “it still comes back to, like, what are you going to do with that capital?”

Q Zapier makes you happier. So how did you come to form Zapier and come to where we are today?

A Yeah, so I graduated college during the financial crisis in oh eight. I was a good student, engineering major, not, like, crazy ambitious, though, like, I wasn't very career-minded, I guess, in that regard, and so I just sort of expected, like, hey, I'm a good student, like, I'll just go to the career fair, and, like, I'm sure someone will hire me, and turned out during the financial crisis, that was not true. People were not just giving offers to, like, you know, find students left and right. It was a bit of a wake-up call, and I was like, okay, well, what am I going to do then? And I remember finding a small software company in the city that I lived in that was Five, six people, and they were hiring a marketing intern, and I was like, well, I don't really know much about marketing, but, like, I'd read some stuff about AdWords, and, like, was like, well, this is actually kind of cool. There's, like, more math behind this. Like, you can better understand, like, performance behind this stuff, so maybe I can talk my way into doing this, and they, for whatever reason, hired me, and getting to work there, like, the company was not a great startup, I guess, but it had a lot of really good people in it, and so I was able to learn how A whole bunch about a bunch of different things, and I fell in love with building software. From that experience, I was like, I want to build a SaaS com…

AI assessment note: “From that experience, I was like, I want to build a SaaS company someday.”

Q me, hey, I don't know what I should do. Should I join a big company and learn from a big company organization like a Stripe or Zapier? Should I join a startup and really just do everything jack of all trades, or should I just dive in and start my own? How do you advise, I know it's generic, but how do you advise graduates when they ask you that?

A Well, if you want to learn how to run a company, I think the smaller company you can be a part of, the better, because you're just going to get exposed to, like, the whole of the thing. Because, you know, for me in that org, like, I got to be a part of product management, I got to be a part of building features, I got to Be a part of running payroll. I got to be a part of hiring. I got to be a part of marketing. I got to be a part of sales and business development, and like, we even wrote grants for the government to try and raise funds. So like, all these different things, like, I got to be a part of them. Now, we weren't necessarily great at all those things, and in fact, that's perhaps why the company wasn't an amazing thing, but I got to experience it all. I knew coming out of it, I just had my worldview had been opened much wider than it was going in, and so I knew going into any company I would have ever started, I was like, here's what all the pieces are. I may not be an expert at any one of these things, but I know what all the pieces are, whereas I think if you go to any sort of, like, post-product market fit company, you generally get slotted into, like, a role, and I think a sufficiently ambitious, smart person can still find ways to learn and have that sort of impact, but it's just not going to be there as naturally, I guess.

AI assessment note: “if you want to learn how to run a company, I think the smaller company”

Q We spoke about remote there, and kind of staying on the theme of geo-agnosticism, really. Like, you know, you started outside the bay, you've also operated within it, and again, leaning on Jay Simons' brilliance from Bond and Atlassian, he asked, what do you feel you gained and lost from the different locations and approaches?

A You know, I think we've always just tried to borrow from the best, Our sort of Missouri Midwest roots. There's like a sort of self-reliance. There's a pull yourself up by your bootstraps, like mentality and attitude that has served us well. Like we knew that to be successful, we were going to have to do that work ourselves and get it done. And then we were sort of instilled that into the culture. And so there's like a very down to earth, salt of the earth humbleness that you find inside of Zapier that I think is pretty rare for most like Silicon Valley companies. I think also having operated inside of Silicon Valley, like We've tried to sort of borrow some of the ambition that you find in companies there. Like, I think you don't necessarily get that in the Midwest. And so we've tried to, like, find things that we like from each and say, like, hey, these things are the good parts, and then sort of jettison the things that we think are not so helpful. I think it was, uh, Bruce Lee has, like, his fighting technique is something like that, which is, you know, hey, borrow the stuff that's good, and then throw away the rest of it. His sort of fighting style is this hybrid of a bunch of different things. And I've always just, like, thought that that was, like, a really good mental model for anything that you do is to not get sort of overly fixated on a particular playbook, but instead…

AI assessment note: “we've tried to sort of borrow some of the ambition that you find in companies there”

Q to a lot of founders' mindsets in a lot of respects, and, you know, you chose a very different route, obviously, and so raising one round of funding since 2012, which is an anomaly, let's just say, when I look at my past guests. But I do have to ask, like, why, when everyone else around you was raising large sums, did you feel that that approach was not optimal?

A Well, this is where I think a lot of Founders, CEOs just get bought into the hype and don't actually do their own assessment of this stuff. This is a thing that I just feel the VC community is just so good at marketing and selling itself that it is really hard to resist that temptation. And one of the things I like to, when I get a chance to talk to like groups of early stage founders, I say, look, you are not raising money. You are selling a part of your company. That's what you're doing. And be honest with yourself about what you're actually doing here. And make sure that when you're selling a part of your company that you're getting what you hoped you would get out of it. Don't do it because of a reason that isn't true to you. And so you need to dig in and say, you know, if I gave up 20% of my company for ten million dollars or whatever, is that ten million dollars going to advance my mission and advance my cause in a way that I feel is worth that? Because down the line, that 20% is going to be worth a lot more than ten million dollars. And so you better be sure that That you can turn that ten million dollars into something much, much better for yourself. And I see a lot of companies go out and just, like, taking these war chests and, like, selling all those parts of the company only just to sit on the cash and never do anything with it. Or to go spend it in ways that aren't…

AI assessment note: “you are not raising money. You are selling a part of your company.”

Q Can I ask, how do you think about accountability with those follow-up tasks? I'm always wary of accountability tied to two people, not one person. How do you approach that?

A You know, I'll be honest, like, we're not super great at this. I tend to say, you know, because we've intentionally put them below the, like, priority list, I don't worry about them all that much. Like, I kind of take the mindset of, like, well, if it was really important, it would have been, like, the number one thing we were And the fact that it wasn't, I personally am not going to drive a lot of accountability for those things below the line. Now, the exec team, if they like feel that it is important, they're free to go do that and drive on that, but it doesn't come from me. It comes from them on those things that are sort of quote unquote below the line. I don't know if that's ideal or not. Like, I think there's times when that's bit me, but we've also like not wasted a bunch of time on other things too. So like, it's just sort of a trade-off that I think we make.

AI assessment note: “I personally am not going to drive a lot of accountability for those things”

Q to a lot of founders' mindsets in a lot of respects, and, you know, you chose a very different route, obviously, and so raising one round of funding since 2012, which is an anomaly, let's just say, when I look at my past guests. But I do have to ask, like, why, when everyone else around you was raising large sums, did you feel that that approach was not optimal?

A Well, this is where I think a lot of Founders, CEOs just get bought into the hype and don't actually do their own assessment of this stuff. This is a thing that I just feel the VC community is just so good at marketing and selling itself that it is really hard to resist that temptation. And one of the things I like to, when I get a chance to talk to like groups of early stage founders, I say, look, you are not raising money. You are selling a part of your company. That's what you're doing. And be honest with yourself about what you're actually doing here. And make sure that when you're selling a part of your company that you're getting what you hoped you would get out of it. Don't do it because of a reason that isn't true to you. And so you need to dig in and say, you know, if I gave up 20% of my company for ten million dollars or whatever, is that ten million dollars going to advance my mission and advance my cause in a way that I feel is worth that? Because down the line, that 20% is going to be worth a lot more than ten million dollars. And so you better be sure that That you can turn that ten million dollars into something much, much better for yourself. And I see a lot of companies go out and just, like, taking these war chests and, like, selling all those parts of the company only just to sit on the cash and never do anything with it. Or to go spend it in ways that aren't…

AI assessment note: “a lot of Founders, CEOs just get bought into the hype and don't actually do their own assessment”

Q We spoke about remote there, and kind of staying on the theme of geo-agnosticism, really. Like, you know, you started outside the bay, you've also operated within it, and again, leaning on Jay Simons' brilliance from Bond and Atlassian, he asked, what do you feel you gained and lost from the different locations and approaches?

A You know, I think we've always just tried to borrow from the best, Our sort of Missouri Midwest roots. There's like a sort of self-reliance. There's a pull yourself up by your bootstraps, like mentality and attitude that has served us well. Like we knew that to be successful, we were going to have to do that work ourselves and get it done. And then we were sort of instilled that into the culture. And so there's like a very down to earth, salt of the earth humbleness that you find inside of Zapier that I think is pretty rare for most like Silicon Valley companies. I think also having operated inside of Silicon Valley, like We've tried to sort of borrow some of the ambition that you find in companies there. Like, I think you don't necessarily get that in the Midwest. And so we've tried to, like, find things that we like from each and say, like, hey, these things are the good parts, and then sort of jettison the things that we think are not so helpful. I think it was, uh, Bruce Lee has, like, his fighting technique is something like that, which is, you know, hey, borrow the stuff that's good, and then throw away the rest of it. His sort of fighting style is this hybrid of a bunch of different things. And I've always just, like, thought that that was, like, a really good mental model for anything that you do is to not get sort of overly fixated on a particular playbook, but instead…

AI assessment note: “borrow some of the ambition that you find in companies there.”

Q Zapier makes you happier. So how did you come to form Zapier and come to where we are today?

A Yeah, so I graduated college during the financial crisis in oh eight. I was a good student, engineering major, not, like, crazy ambitious, though, like, I wasn't very career-minded, I guess, in that regard, and so I just sort of expected, like, hey, I'm a good student, like, I'll just go to the career fair, and, like, I'm sure someone will hire me, and turned out during the financial crisis, that was not true. People were not just giving offers to, like, you know, find students left and right. It was a bit of a wake-up call, and I was like, okay, well, what am I going to do then? And I remember finding a small software company in the city that I lived in that was Five, six people, and they were hiring a marketing intern, and I was like, well, I don't really know much about marketing, but, like, I'd read some stuff about AdWords, and, like, was like, well, this is actually kind of cool. There's, like, more math behind this. Like, you can better understand, like, performance behind this stuff, so maybe I can talk my way into doing this, and they, for whatever reason, hired me, and getting to work there, like, the company was not a great startup, I guess, but it had a lot of really good people in it, and so I was able to learn how A whole bunch about a bunch of different things, and I fell in love with building software. From that experience, I was like, I want to build a SaaS com…

AI assessment note: “From that experience, I was like, I want to build a SaaS company someday.”

Q I love that, and I didn't know that. Tell me, what was the last time your mind was blown by something, and what was that thing?

A I mean, this happens a lot. So I'll tell you one that is on my mind recently is, so we actually just acquired this company, MakerPad, and Ben, the founder over there, one of the things that, like, got him on my radar is he would just post these tutorials on On, like, how to build clones of these, like, pretty major tech apps. Like, he built, like, an Airbnb clone and, like, some of these other things using no-code tools, and I was just like, oh my gosh, this is so cool. Like, this is incredible. Like, he is pushing the envelope farther than anyone else has pushed what is possible with these tools, and so that certainly was perhaps not the most recent time, but it is an area that has blown my mind.

AI assessment note: “it is an area that has blown my mind”

Q Can I ask, how do you think about accountability with those follow-up tasks? I'm always wary of accountability tied to two people, not one person. How do you approach that?

A You know, I'll be honest, like, we're not super great at this. I tend to say, you know, because we've intentionally put them below the, like, priority list, I don't worry about them all that much. Like, I kind of take the mindset of, like, well, if it was really important, it would have been, like, the number one thing we were And the fact that it wasn't, I personally am not going to drive a lot of accountability for those things below the line. Now, the exec team, if they like feel that it is important, they're free to go do that and drive on that, but it doesn't come from me. It comes from them on those things that are sort of quote unquote below the line. I don't know if that's ideal or not. Like, I think there's times when that's bit me, but we've also like not wasted a bunch of time on other things too. So like, it's just sort of a trade-off that I think we make.

AI assessment note: “I personally am not going to drive a lot of accountability for those things”

Q No, I, I totally get you. Uh, we mentioned the primary capital element there. Secondaries are becoming more and more a prominent Part of our ecosystem, which I think is a great thing. I'm a big advocate for secondaries. How did you approach secondary sales, Wade?

A Uh, you know, I generally think that, particularly for founders in particular, like, having a little secondary generally is a good thing. When you run a company for a long time, you tend to not pay yourself super well. You take on a certain, like, personal finance debt, and so at some point in time, when your company is in, like, really good shape, you know, taking a little bit of money off the table in a secondary is, like, I generally think the risk-reward equation there is probably a Pretty reasonably smart. You know, I think even, you know, like the base camp crew did this, who is like, I think even more sort of anti-VC than I am, right? So I generally think it's like, just a sort of smart thing to say like, hey, I'm in a position where I can sort of set myself up, set my family up, and not have to worry too much is helpful to your business, because now you can take bigger bets, take bigger swings, without worrying too much about how that's going to blow back on your personal situation.

AI assessment note: “taking a little bit of money off the table in a secondary is... reasonably smart”

Q No, I, I totally get you. Uh, we mentioned the primary capital element there. Secondaries are becoming more and more a prominent Part of our ecosystem, which I think is a great thing. I'm a big advocate for secondaries. How did you approach secondary sales, Wade?

A Uh, you know, I generally think that, particularly for founders in particular, like, having a little secondary generally is a good thing. When you run a company for a long time, you tend to not pay yourself super well. You take on a certain, like, personal finance debt, and so at some point in time, when your company is in, like, really good shape, you know, taking a little bit of money off the table in a secondary is, like, I generally think the risk-reward equation there is probably a Pretty reasonably smart. You know, I think even, you know, like the base camp crew did this, who is like, I think even more sort of anti-VC than I am, right? So I generally think it's like, just a sort of smart thing to say like, hey, I'm in a position where I can sort of set myself up, set my family up, and not have to worry too much is helpful to your business, because now you can take bigger bets, take bigger swings, without worrying too much about how that's going to blow back on your personal situation.

AI assessment note: “having a little secondary generally is a good thing”

Q well, there's many incredible things, but, you know, topic du jour is obviously remote work, and I hear so many interviews, and they just give, like, the most B.S. answers to, like, what makes remote work successful. So I'm really interested, when you think about, like, what specifically you do or did when it comes to remote work that allowed you to succeed, what do you think those would be?

A I think it comes down to a few things. One, at the end of the day, working remotely is not so different than working in an office, in that people want to feel like they have autonomy, mastery, purpose, like, those things from, like, the book Drive is, like, Daniel Pink's stuff, like, still applies. You're just still trying to, like, how do you give that in a slightly different environment? And a big part of that stems from management and leaders. Like, if you have great management, great leaders, they're going to be able to sort of help set up these systems and structures in a way that are going to be effective. Now, sure, you don't sit around a coffee table or a conference room table. You sit on Zoom. Sure, you should probably lean to more asynchronous work rather than synchronous work. But, you know, you're probably going to have to work more on, like, camaraderie and community building in a distributed team. You can't rely on The cafeteria room and the kitchens and stuff like that. So there's things that are like, okay, the default setting in a remote is going to maybe be harder in these dimensions and easier in these dimensions. So I think it just really boils down to like identifying like, okay, these are the things that are going to be a little harder and we're just going to have to be a little more intentional about those things versus actually we have a bit of an advant…

AI assessment note: “lean to more asynchronous work rather than synchronous work”

Q well, there's many incredible things, but, you know, topic du jour is obviously remote work, and I hear so many interviews, and they just give, like, the most B.S. answers to, like, what makes remote work successful. So I'm really interested, when you think about, like, what specifically you do or did when it comes to remote work that allowed you to succeed, what do you think those would be?

A I think it comes down to a few things. One, at the end of the day, working remotely is not so different than working in an office, in that people want to feel like they have autonomy, mastery, purpose, like, those things from, like, the book Drive is, like, Daniel Pink's stuff, like, still applies. You're just still trying to, like, how do you give that in a slightly different environment? And a big part of that stems from management and leaders. Like, if you have great management, great leaders, they're going to be able to sort of help set up these systems and structures in a way that are going to be effective. Now, sure, you don't sit around a coffee table or a conference room table. You sit on Zoom. Sure, you should probably lean to more asynchronous work rather than synchronous work. But, you know, you're probably going to have to work more on, like, camaraderie and community building in a distributed team. You can't rely on The cafeteria room and the kitchens and stuff like that. So there's things that are like, okay, the default setting in a remote is going to maybe be harder in these dimensions and easier in these dimensions. So I think it just really boils down to like identifying like, okay, these are the things that are going to be a little harder and we're just going to have to be a little more intentional about those things versus actually we have a bit of an advant…

AI assessment note: “you should probably lean to more asynchronous work rather than synchronous work.”