Parker Conrad’s Revenge Fantasy

Rippling was born out of kind of this like revenge fantasy. That's what kind of got the company going. And it's certainly what, what kept me going for the first couple years. I love the people I work with. I sort of really like the problems that we're solving. I feel like we're, you know, making a difference for customers in this sort of small way for their companies. And that's all extremely motivating. But early on, you know, it's, it's a grind. People come to me all the time. They're like, oh, I'm like thinking about doing, you know, starting a company.

What do you think?

And my advice is always like, don't do it. It's a terrible.

Okay. In this episode, you're going to hear from Parker Conrad. He's one of the most compelling CEOs in Silicon Valley, in my opinion. He runs Rippling. It's an amazing back office software company. It's a $17 billion market cap with 4,000 employees, incredibly successful. Almost everyone, including myself, never thought he would get this company off the ground. And that's because he was very violently fired from his last company's benefits. And I remember when that went down and I thought, man, he's done. He'll never get up off the mat. And I'm really impressed he has and how well he's done. He's also had a lot of drama with a competitor deal very recently who was spying on information inside his systems. And there's a lawsuit and arrests and all kinds of drama around that. So there's lots of good drama in here for you who are into that. But in between the drama, there's some pearls of scale up CEO wisdom. He's not your typical CEO. He rethinks things from scratch in a way that I find compelling. I like the way he thinks about hiring. I think it's quite interesting how his company has over 100 former founders in it. I like the way he thinks about scaling without getting sclerotic. 4000 people is pretty big. It's still moving fast, very hard to do. And I like how his chip on his shoulder can supercharge his whole career and that can supercharge yours too. So he's going to get into that. Parker's basically written the book on turning your darkest professional moment into your greatest competitive advantage. I hope you like it. How you doing?

Doing pretty good.

At Sequoia, one of the things they always talk about is they like founders with chips on their shoulders. Do you have a chip on your shoulder?

I Think so. I think it's like, you know, maybe faded a little bit over time. You know, I tried very hard to keep it honed to razor sharpness, but I think certainly Rippling was born out of kind of this, like, revenge fantasy. And, like, that's what kind of got the company going. And it's certainly what. What kept me going for the first couple years. You know, there are a lot of other things that I love about my job. I love the people I work with. I sort of really like the problems that we're solving. I feel like we're, you know, making a difference for customers in this sort of small way for their companies. And that's all extremely motivating. But. But, yeah, early on, you know, it's. It's a grind when you're starting a company. And this wasn't like, my first rodeo. It's my third. And doing it the third time around, I think they're really like, it was helpful to have this, like, extra bit of motivation that was there for me every night when I went to bed and like, every morning when I woke up.

Do you think that you have exacted revenge on those doubters and those people who did you wrong or not? And do you think you'll ever put that to bed in your own brain? Or is it. Is it a source of constant motivation for the rest of your life?

I don't know. It's so. Have you ever seen. There's a South park episode, the. Probably the Underpants Gnomes I love.

It's my favorite episode.

So it's sort of. Yeah, underpants for. For people who aren't familiar with it. You know, the kids sort of follow these gnomes that are, like, stealing everyone's underpants, and they follow them to their secret underground lair, and they're like, why are you stealing everyone's underpants? And there's this sort of secret plan for world domination, and it's like, step one, like, steel underpants, step three, world domination. And the kids are like, what's step two? And they're like, oh, shit. We never really. We never really thought about that. And sometimes I think it's a little bit like that with me, where it was like, you know, I felt like when things went south at Zenefits, I wasn't allowed to talk about it. And the entire story was being written by sort of my antagonists, you know, that were just saying all the stuff that, you know, I felt wasn't. Wasn't true, wasn't actually what was going on. Like, it was unfair And I couldn't do anything about it. And so for me there was always kind of this idea where it was like step one, build this like multi hundred billion dollar outcome in like the exact same space and by doing it in exactly the opposite way of everything that they said was like the right way to do it. And then like step three was like somehow like you know, get, get like revenge on all of them. And like step two was like always sort of like vaguely like how's like connected to be was like sort of has always been sort of unclear. The company's a lot of fun. You know, like I, I started out.

And not just revenge.

Yeah. I mean everyone sort of told me, well you need to develop actually early on like our, our, our series A Investor. You know, I, I was very open about these motivations and, and Mamoon was like, hey, that's kind of dark. Like maybe you should, maybe you should talk to someone about that. And actually there's like an exec coach that came in and I talked to this guy and you know, he was sort of constantly like you need to have all these positive motivations and no negative motivations. And he went and he did sort of interviews with all of my direct reports of the company. And one of his questions was like, how do you feel about the fact that Parker is like motivated in these ways? And, and everyone was like, I hope he never loses it. And so there was definitely like that element of it. But like over, over time I think, you know, despite all of my attempts to sort of like focus my anger on this stuff, I think that, yeah, like the, a lot of, you know, sort of day to day is like, you know, all of that stuff is very distant and it's much more about sort of the excitement of what we're building and the problems that we're solving and the people that I work with, who I really enjoy working with.

Yes or no? Have you exacted revenge on your antagonists from Zenefits?

I don't think so.

Will you at some point answer that question as a yes? And at what point is that a yes?

I'm not sure that there is any.

Just 100 billion dollar IPO kind of thing. It's like, okay, check I was right.

I don't think that, that I'm not sure that like one leads to the other, you know, and I think that you don't necessarily get that kind of satisfaction. But also everything sort of fades with time. It stops being the thing that is like the focus of what you're doing every Single day.

I remember when that whole thing went down. And then I remember you got your Series A. And I thought, okay, you had A. Someone painted a scarlet letter on you. And I was like, it's going to be hard for him to raise again. And you raise, you talk about that fundraise and how did it go down? Like getting over that must have been non trivial.

It was a weird process because there were definitely like, I mean, at the time, Rippling was doing really well. I mean, like the numbers, we kind of showed everyone our numbers and the numbers were, I think, quite impressive.

And you had personally, you know, angel funded it. I assume you seeded it.

I did some amount. And then, and then we raised a seed round where we had a bunch of like really early believers a lot. And a lot of them were former Zenefits seed investors. Yep. Who really. Who backed me again? Yeah, And a lot of sort of people in the YC community. YC Partners initialized, you know, Gary Tan, Sam Altman, all those guys.

So you're doing the A, you got the scarlet letter.

And so then we went out to raise our Series A. And it was very controversial. And there were like, every firm was really interested because the numbers were so good. And I think there were a couple of firms that went really deep. Like basically at the time, the partner at Sequoia, Mike Vernal, who was looking at the deal, Mike came to me and he said, look, there's one reason to do this deal and there's one reason not to do this deal, and they're the same reason. And that was what everyone was trying to figure out. And I think Sequoia went really deep. And I think Mike told me that you guys did, because Sequoia always does this just incredibly deep diligence. Talk to 50 different executives or people in management positions at Zenefits to really understand the picture and came away with a lot of conviction that they felt like, okay, we, Sequoia feel very comfortable with this. Unfortunately, we didn't end up working with Sequoia at that point. It was a little bit later. Yeah, but a couple of other firms did that as well. And there were a couple that kind of just like backed out. And you know, one firm sort of lead guy there, you know, called up David, David Sachs and you know, I got a phone call on a Sunday night, said, hey, so and so spoke with David, we've got to cancel the job meeting on Monday. You know, like it was just. There was sort of a, a more superficial amount of diligence on it. There Were these two camps and. And, you know, but even so, there were enough people in the camp of, like, we're excited about the business and not concerned about the history, that the round was, like, really competitive and got done nice, you know, on great terms.

Nice.

We were pretty excited about it.

When was the last time you saw David?

I have not spoken to him since about a week before I left Zenefits.

I see.

I've sort of, like, seen him across the room at a conference since then.

Is there anything you want to say to him today?

Probably. Probably not a great idea.

How about. I'll say it for you. I told you so. I don't actually.

I don't actually think that. That's what I think. Like, if I was talking to David, I would really be like, why? You know, like, why? Like, I look at it and it just. It feels like it was so unnecessary.

Yeah.

You know, like. Like, even in a world where they were like, hey, we've got to make a change. Like, those types of things are usually not accompanied by the type of character assassination. Like, and it was, like, deep and prolonged effort. Like, they hired people, and those people were. Were sort of doing this in the media, like, pitching stories, but, like, week after week after week. And that is just like, it's unusual. It's expensive. It's like, a lot of effort.

I remember it went down. And I remember the media, they wrote some things that were very tough. They basically blamed a lot of stuff on you. I don't remember the prolonged. But why do you think they thought that was a good idea? I mean, they're relatively rational economic actors.

Some of this, I think, is like David. And some of this you sort of see in the way that David, I mean, is like, you know, very successful as sort of this more political type of actor. And I remember David came to me at one point, we know, at Zenefits, when we were having our own sort of conflict with adp, we ended up in some litigation with them. And David told me, he said, look, here's the thing. If you're ever in kind of one of these media shit fights, you want to attack, attack, attack, attack, attack. And if the other guy rolls over and cries uncle, that means it's working and you want to keep attacking, attacking, attacking, attacking. And I think that that was like his playbook. Like, that was sort of the way it operated. And, you know, and some of it, it wasn't. It wasn't just that, like, they blamed me for everything. I mean, like, look, ultimately, I'm the CEO I, I, you know, I am responsible for things. It was the way that things that were mistakes, you know, that were like, hey, we, we thought this was what we were supposed to do and it was something else. Were instead the legal word for this would be like, you, this is like, you know, like there's some intentional kind of thing for what was, I think in retrospect, much more just sort of accidental. Like as companies are growing quickly and you know, little things that, you know, you sort of don't recognize as, or just unaware as. Like things that are, you know, suddenly are like actually you overlooked something.

And how did you feel like when you first saw it? I assume you didn't have a heads up. You saw it. Like, was it anger? Was it confusion? What did you say to your wife? Like, what was going on inside the four wal your body?

One of the things that happened right before the announcement is I was like so depressed about the whole thing that I stopped looking at the media. And I didn't read stories about me or about rippling for like five or six years from that point. It was a long time or zeniths. And my wife would always read them. And so when the announcement came out, there was a press release that, that we had drafted. And it was sort of one of these sort of anodyne things that was like, hey, look, company needs new type of leadership.

Yeah.

Parker, you know, like, great job taking it this far.

Yep.

David coming in, wants to spend more time with his family.

Typical stuff.

Typical stuff. And, and, and instead they just like, David issued a different press release. And the press release was like, this company has a whole bunch of compliance problems. It's because, you know, Parker doesn't care about compliance. He's not here anymore.

Yeah.

And it went south from there. And I remember, you know, when it came out, I mean, it was such a shock. It was just very unexpected. And then it just got worse from there. And it was actually my wife that read it and turned to me and said, oh, they, they, you. Like, she was like, don't even read it. Like, don't look at it. It was deeply depressing. I mean, there were like really, really dark moments. And some of like the chip on the shoulder was kind of like, I'm either. There was sort of this one little ray of light, this one path out, which was like, you know, build this company and make it successful or like it's just all over and you kind of give up. And it was kind of like it felt like those were the two choices and like that and that Was very hard and very depressing. But it was also like very clarifying and very motivating that I felt like, okay, this is the only thing that I'm here for, and this is the only thing that I care about is making this thing work. Okay.

A lot of people listening are founders, CEOs. People want to be CEOs. You've been through some crises and some shit shows. I have two advice for people crisis going on. Most CEOs hit some big shit show crises during their tenure. Any advice?

People come to me all the time. They're like, oh, I'm like thinking about doing, you know, starting a company. What do you think? And my advice is always like, don't do it, it's a terrible idea. And like I. And people always sort of laugh. They're like hahaha. But like it's very, like it's very real. Like I do think that it is like much, much harder than people expect. It's not just that it's hard to be successful, it's that it's sort of really kind of soul destroying, like even when you're successful and very hard to kind of manage your psychology through, through that, that process. And people come out the other end and there's a lot of, you know, there's a lot of, I think, talk about, you know, failure being sort of this positive thing that you learn a lot from. And actually I think you don't learn a whole lot from failure and you learn a lot more from success. And it's really hard. You know, usually I think people. I see many more people that do something like this and don't succeed. And it sort of like destroys a lot, you know, it destroys marriages, relationships, you know, ambitions. You know, like people kind of come out like a shell.

Yeah.

Their former selves and. And so it's not something that I, that I'd recommend.

I kind of agree. I describe HubSpot as like two steps forward, one giant step back. Two steps forward, one giant step back.

Over and over again.

It was, it looks smooth and easy from the outside, but man, it was a grind. It was not easy. And there were, there were a lot of moments where I really hated my job. Yeah, you feel the same way?

Yeah. I mean I would say that one thing that was, that was different about rippling, I think in part because of the experience at Zenefits is like people sometimes ask me like, you know, what I learned and sort of there's like insouciantly. I'm kind of like, I didn't learn Anything like, you know, Zenefits failed for dumb reasons and like, there was nothing to learn from that. But I do think that like, you know, over time you sort of slowly accumulate a kind of pattern recognition about like, what matters and what doesn't. And, and that can, that makes things a little bit easier because there are a lot of things that come up where you're like, this probably doesn't matter. Yeah. You know, okay, when it sucks, but like, it's nowhere near. And no matter how bad things have ever been at Rippling, they have never come even close to how bad things were in the sort of six months, like, you know, right after the end of Zenefits or when I left Zenefits. And so everything kind of pales in comparison. And, and that is always this sort of comforting in a way, what you.

Brought something up, what matters and what doesn't. Like, what matters that people don't think matter and what doesn't matter that people think matters.

I mean, sort of the advantage of having done something before, I think you start to have good judgment about what is, you know, because so many of the things that come up are probably like, doesn't matter.

Yeah.

Not going to make a difference. And some things come up are like, ooh, that one's going to count. And I think it's hard for first time CEOs to really see the difference between those. It feels like everything's going to matter.

Yeah.

And that's part of why it's like so overwhelming and awful.

Yeah.

And some of the things really actually do matter.

What really matters. I think getting your strategy right, like, where are we headed in the bus and getting the right people on the team are really important things. And a lot of other stuff can fall by the wayside.

Yeah. I mean, those things matter and kind.

Of getting like your mission set up so people can get excited about the darn thing.

Yeah. I'm trying to think, like, I mean, I think like there are little, little things that go wrong that feel very consequential in the moment that you start to realize over time don't matter. And like, if you're not growing that, that obviously matters. At Rippling, it took us like two years to get to a point where things started working.

Yeah. HubSpot was about that too.

And like for two years it was sort of this exercise to try and like basically beg the team not to leave until things started working. But there was also like zero doubt in my mind that it was going to work and that that was sort of a big difference. Because like, I sort of knew that like if you built these things and got, and got to this sort of, you know, this island of product market fit that was admittedly pretty far over the edge of the horizon line. But like, I knew that there was land out there and, and that if you could get there, this was going to work. And I, you know, had, having seen what was working and why at Zenefits, I just had like unshakable conviction that this was. And so there was never a doubt that was going to work and it was merely about like whether like, quite frankly we could keep, prevent everyone from quitting, like before we, we got there. And so early on actually like, you know, trying to just keep the team together.

Yeah.

Mattered a lot.

Yeah.

And at that point, whether it was like working today or not, like didn't so much in this very specific context of the company that I was building. And I think for a lot of other companies that's not true because like, you know, you might believe that things are going to work, but you're probably wrong or you know, like you're, if you have a lot of conviction about it, your conviction is like misplaced. Yeah, maybe mine was too. But I, you know, like, I was sort of crazy enough or believed that I had reasons to believe that this was going to work. Parker.

You'Re kind of a contrarian along a lot of lines. That's one of the things I've always liked about you. What do people have totally wrong about being a CEO? Like there seems to be sort of a rule book around it that is kind of getting rethought these days. And I feel like you're rethinking pieces of it. What, what's all wrong about CEOing? What are these founders, CEOs? What mistakes are they making?

Well, I'll tell you, I mean, I don't know. I know so little about like any business that's not my own. So it's hard, it's hard for me to have like big opinions about like sort of the ecosystem. But I think that like one thing that I, that I sort of believe in, that maybe is becoming like, you know, more, more sort of more, more of the conventional wisdom today is I've always struggled with the idea that as a CEO, you're supposed to kind of manage top down through a set of deputies. And you know, you, you hire people who are knowledgeable about this area, you trust them and you let them kind of do their thing. And that's just never worked for me. Like what's, what's what's worked is you kind of have to reason from first principles, and you can do that with some of your lieutenants who can help you through it to sort of convince yourself of exactly what the right approach is in. In that area. And you have to have, like, real on an on the ground understanding of what's actually going on yourself. And if you don't have that, like, that's the only thing that's. That's worked for me. And it's really. It's tough to scale. It's tough to scale that. You know, it's hard on you. I think it's hard on some of the other people, but it's the only thing that sort of worked for me. And the only thing that. It's the thing that's really worked for Rippling. And so we have a leadership principle that we formalized on this that we call Go and see that's basically like, look, if you're. It's true for me, but it's also true for, you know, executives and managers that, like, you know, you've got to. You've got to go right to the ground.

Coal face.

Yeah. And get. That's a good way of saying it. Right. And you've got to, you know, something. There was a point in time where things were just, like, really going wrong with tax operations. And like, you know, we're. We're a payroll company. One of the things that we do is we do, you know, we do these sort of quarterly filings for clients. And, you know, there are thousands of agencies across the country that you need to send these to. And. And there are a million little things that can go wrong. And if anything's off by like, a penny, clients get, like, angry letters about this, and it's really bad. Things were going wrong. Like the notice. The rate at which clients were getting notices from Rippling, we knew, was like, higher than the notice rate at other companies. And it was like a. An existential threat to the business. And like, that was something where there was some muscle memory for me that this was actually something that would kill the company. It matters. You know, it was something that matters. You know, the only thing that worked to solve it was, you know, was what happened is I got, you know, like, me and my COO and like, you know, the person running the team and like someone else, we sort of wiped out our calendars and we sat down and we said, for the next week, you know, we're going to just be tax ops agents. And so we're literally going to you know, because there was this growing backlog of notices that needed to be addressed that clients were sending us. And we're just going to pick from the queue and start figuring out like calling up the tax agency why did the client get this notice, what happened, you know, why did they believe that, you know, the, the amount was wrong or the money didn't get there or the filing was not on time or something. And, and then reverse engineer it in our systems and be like. And it was just like doing, doing the actual work of doing it was the, the only. And then sort of like by doing that we developed this understanding of like what was broken about the process, what was broken about the systems, what were the changes be made. But it was like impossible to diagnose or understand without sitting there and doing that. Okay.

On the matters thing, it seems to me from just listening to you and I also spoke to a couple people on your team, a lot of things matter and then one of the insights I think you've had is details matter from the CEO on down and you're in the details in a big way for a company that has four, four or five thousand employees. Is that fair to say? I think more so than me for sure. It seems like you are like you sit in the middle of the engineering floor. It sounds like you are on the coal face for somebody in a pretty good sized organization.

I certainly try to be and so I view that as like a huge compliment from the team. I think the place where I try and do that the most and what's maybe sort of most unusual about ripplane is that I'm the only full admin for Rippling in Rippling. And so I run payroll for the entire company across dozens of countries. I manage sort of like benefits and a lot of IT policies and other stuff within the system approve expense reimbursements, things like that.

I was similar in HubSpot. I was a very active user of HubSpot Spot, one of the most active users for many years.

So I think that's important. It's like one of the things like people you know learn when they join Rippling is like the CEO approves every expense reimbursement over $10. And the reason for that is like not that I'm like this jerk that's like harassing people about their expenses, it's that I'm trying to actually use the product in the same ways that that clients would that like a diligent controller or you know, sort of accountant.

Yeah.

Would use the system and help review it in the same ways that they would and try and use that to sort of iterate and improve on things over time. There are a lot of things that we get wrong as a company, but I do think that, that that element is like a little bit of a superpower because I know that, you know, the CEOs of you know, ADP or.

They'Re not doing that or never run.

Payroll in their life. No, like never. You know, there's a sort of on the ground understanding of the system and that, you know, that doesn't mean that, you know, we always get everything right. But I think that, you know, it's a, it's a sort of control on the system and one of the ways that it play. One of the things that I'm most proud about is that we did this study where we, we looked at companies that use ripplane and companies that use anything other than ripplane and some of them use like modern systems competitors of ours that are sort of more recent market entrants. Some of them use the more old school systems. And you just look at how many people those companies have in HR, IT and finance roles and GNA roles within the organization based on LinkedIn data and what you find is that the companies that use Rippling at any given size range. So you have to look at it by company size. Obviously, you know, companies that use Rippling have about half the people in those functions than companies that use anything. I love that, I love that set. And that's. Look, I think that, that you know, it's not that, you know, our pitch is not like, hey, like, you know, like lay off people. If you use Rippling, it's those extra headcount. They, they represent all of this administrative burden. They, they represent attacks on your business because those are people that are just moving data between systems dealing with administrative pain that you could instead redeploy for things that matter within your business.

Parker, so you're in the details. You just talked about your own CEO journey from like the four of you to the 40 of you to 400 of you. There's 4,000 of you. Somehow you've managed to stay in the details. How has your job changed? What advice do you give to that founder with 40 people on how to scale it? How did your job change and how did your day to day change?

I think probably the most important thing was the people a level below me. And honestly I think probably their jobs have changed a lot more interesting than mine has because the executive team at Rippling has been pretty stable over Time there's been like, there's been some turnover, but I think, you know, a lot of the people that are there, you know, like our CRO was the eighth person in the company and you know, my COO joined when, you know, right after the series A. But he and I, you know, had known each other since college, so we've been friends for a long time. You know, there have been a bunch of people that have sort of been there a long time. And so there's just, I think, a lot of trust and I think every, you know, everyone's kind of like, everyone's sort of grown in their, in their function and in their job over time.

One of the things I've noticed Parker VCs do, as soon as they make their investment, like the first thing they say is, like, we got to up level the team. Yeah. And when I look at the best companies, a lot of the management teams are kind of homegrown. Like a lot of HubSpot's management team been there since the pretty early days. What do you think of that advice? I think Homegrown's really underrated.

Homegrown's underrated, but also like, if the people, sometimes the people that you're trying to grow are not going to make it sometimes, you know. And so I think what I would say is like hiring people that you just are, you're really close to, I mean, it's weird to say, but hiring people that like, you've worked with, that you're friends with, that you enjoy working.

With, like, really lowers the risk.

Really underrated, actually. Yeah.

Lowers the risk. It's underrated. Yeah.

And, and so went to school with. Yeah, there are people that we brought in that, you know, we hired that were not like that, that had been unbelievably successful as well.

Yeah.

But there is something to the fact that like, you know, for the, for a long time, Rippling cmo, he's now stepped into a different role, but was this guy, Matt Epstein, who was like, you know, I worked with him as cmo. My first company, he was CMO at Zenefits. He joined Ripplane, was CMO at Rippling. Like it was just this long standing, like, professional relationship that I had. And there's sort of something to that. I feel like I have a pretty good sense of whether someone's going to make it or not. And I'm sort of wondering, like, how would I do your job at Sequoia and advise like an entrepreneur on their team? I would have a lot of humility about it and I'd be like, man, I just don't, I don't know how I would explain that or judge that. And, and one of the problems I think for investors is I think it's actually really hard to do from the outside. And so even if you have like done it yourself, you know, you're just not spending enough time at the company to really know about this exec and whether they're going to make it. And so the advice is like maybe not all that useful. And then, you know, if you're, if you're an entrepreneur, it's doing this for the first time. It just, I don't see how anyone figures. I mean, look, looking back, I'm like, I don't understand how anyone figures their way through this because it seems like so hard to know having not seen it.

I'd say the one thing I've noticed with so many of the early stage, mid stage startups is their hit rate on hiring that external. Been there, done that. CMOC would have is it's 50% within 18 months. It's much harder than it looks. People don't talk about it. What have in, in this vein, you're interviewing somebody. What, what's your filter? What are you looking for? What's your process? These. Like, do you, is there anything unusual you're doing around there that you think you might be. Have some intuition that people don't.

Here's what I do and I don't, I'm not, I'm not saying that what I do is like the right thing to do.

Yeah.

But usually what I do is I send candidates all of the investor materials that I prepared. So I send them like we write up a memo on the business. There's like some metrics and I send all of that to them ahead of time so they have context and they show up to the meeting and I'm just like, look, this first meeting is really just a chance for you to ask me questions. So you know, sure, you had a chance to look through this. You know, what, what didn't make sense to you? What were you like? I don't think that's right. What did you have questions on? And let's talk through it. And then usually we sort of talk through their questions and sort of secretly, I'm sort of judging them by how that conversation progresses. And so some people have no questions and that's usually a pretty bad sign or some people have clearly fake questions. And some people, like actually even very skeptical questions are really good. Like if they're Smart. There are some people that they immediately get to the core of the issue where they identify the two things that are going to really be problems. And then sometimes we have a great discussion about it. Because I've thought about those things too. I spent a lot of time. Here's how we're approaching it. Here's what I think and here's what didn't work, and here's what I think is going to work. And this is why this is so important. And sometimes the people that ask those really challenging questions, they get it really quickly and they're like, oh, yeah. And that means also that. And then as a consequence of that. And I think it works because it kind of simulates what the actual working relationship is going to be like where we're going to have those types of conversations in our one on one meetings. And that's going to work. So that's always been the thing that's been most telling for me. That and back channel references.

Yeah.

You know, I usually ask people, like, give me like six references, not two, because everyone's got two. So, you know, give me six. And then I call two randomly from that list. And then I try really hard to find people that are not on your list.

I'm the same. Yeah.

And that, that's been really telling. The thing that I've always. I don't have a good answer for is, is I found it's really hard to summon great executives on demand. And so.

Wait, what do you mean by that?

Well, it's like someone suddenly someone leaves or someone is like, it's like not going to make it. And it's, you know, and you're like, crap, I need a cto.

Yeah.

Our current cto, who's amazing, was someone that randomly fell into my lap, you know, that, that someone at Sequoia introduced me to. And, and, and it was like, wow, like, this is amazing. And it was very clear that, you know, this person was exactly who we should hire. But we'd hired someone else, you know, six months earlier, it was not working out and we hired that person sort of like it was one of those things where we had been looking for so long.

Yeah.

You gave up, you know, looking for so long. I was like, oh, maybe, maybe it'll work, you know. And we had.

Does that ever work?

Never, never, never does. But like, what are you gonna. I mean like we'd been looking. I don't know, I think we'd been looking for like a year.

Yeah.

You know, it's just.

And all the, his direct Reports report to you in the meantime, which is, like, brutal.

Yeah. And so. And you know, and. And so what? I mean, I'll tell you what doesn't work is, like, usually, like, exec recruiters don't work.

Okay, I was just about to ask you that. Okay.

Exec recruiters are, you know, great at sending you solid B candidates, and there's always the exception that proves the rules. So we hired our cfo, who's amazing.

Good person to hire. Through an executive recruiter.

Through an executive recruiter. But, like, actually, like, really incredible. Yeah. And so there are. Are some exceptions, but usually they send you a lot of B candidates. And the problem is that I think the really incredible people, they get snatched up totally before they know before they leave. With an exec recruiter, like, they're like, you know, they've always got people paying them and they get a million options and they've got relationships with people and someone is yanking them out, and, like, they sort of, you know, they sort of secretly whisper to their spouse that maybe they're thinking about leaving. And there's five people this morning that heard about it and are already, like, you know, been talking with them for a long time and have worked with.

Them before and have been nurturing them. They're on drip marketing campaign.

Make it into the.

Okay, let me ask. Related to this, you hire someone, it's a month in. You're like, I might have fucked this up, but it ended up working. Has that ever happened?

Never.

Okay, so a month in, if your gut tells you it's not right. But how long do you wait?

Always longer than a month.

How long do you wait? Six months.

Yeah. And the frustrating thing is I see this behavior in managers at rippling, and I get very upset about it and very angry about it. Like, why did you. Why did you fuck this up? You know, like. Like, you can see it happening. Like, I have this conversation all the time where I'm like, you know, I'm like, okay, here's your team. How many of these people right now, like, tell me which of these people you would bet your career on? And like, whoa. And it's like, well, this person and this person. And I'm like, none of the rest. They're like, well, it's a tough. You know, And I'm like, okay, get, you know, like, fire all, like, let's start over, you know, and. And like, oh, no. You know, like, yeah, but, you know, there's all kinds of reasons why, you know.

Yep.

You know, not yet. And inevitably, they're all gone.

In a year, they're all gone.

But it takes a long time to get there. And it's so frustrating, so infuriating. And it's like, why, why can't you as a manager just do the job that we expect of you and make the hard decisions? And I make all the same mistakes myself.

Right.

You know, it's like, you know, equally difficult for me when things are not working out.

It sounds to me from people I've spoken with inside of Rippling and yourself that it was an intense startup and all startups are pretty intense, but it's now an intense scale up. You've kept that pace and intensity up as you scale through the years. Most of the founders I work with are really struggling around 100, 150 employees. They're bringing in new people they didn't know well, there are a couple middle managers showing up that intensity and that pace doesn't seem to scale. How have you scaled that?

Well, I think one, one thing that I believe very firmly is that there's ultimately only one person in the organization. There's only one constituency for speed and it's you as the CEO. And so it's really one of your biggest jobs is to sort of set the clock speed of the organization. And the reason is, is that everyone else in the can sort of solve for all of their problems by just extending the timelines. You know, like they can get it done to, you know, in the ways that they want to get it done. They can, you know, they don't have to, you know, sort of make unreasonable asks of people that they're, you know, like every, every other constraint can be solved for, with more time. What happens is things start to get like really slow. And there are real problems with that for the organization long term, but usually not for like any individual manager or executive within the company. And so you're the only natural constituency for moving quickly. And so you really have to be, you really have to care about it and you have to sort of pay attention when people are trying to slow it down. And so one of the, one of the things that happens is like your team will often come to you and they will present you with what I call CEO in a box decisions where they will say look, we can do A or we can do B like you choose. And it's this illusion of choice.

It's a tyranny of war.

Yeah, it's, it's this ill, but it's an illusion of choice because the choice has already been made for you. Because the important Choice was the decision that A and B cannot coexist. And usually my immediate reaction when someone brings me something like that is to just on principle insist that we have both A and B and understand what laws of physics are violated that prevent A and B from coexist. It's like the second law of thermodynamics problem. Sometimes it's like it's much harder for the team to do A and B and they would prefer not to do that. Sometimes it's actually just as simple as asking people for a third path, you know, to like say, I don't, I don't like these options. Like can we just think a little bit harder? And is there some way to kind of get there? When you think about like the pace at which organizations move, I think the natural thing is people sort of believe, man, if you're like tyrannical CEO, that's like driving people really hard and what's going to happen at most maybe it's like 20% more. Patrick Collison has this great site that he put together on things that moved absurdly quickly and things that moved very slowly. And it's this example of the space program to land someone on the moon was like four years and the Van Ness bus lane was like two decades or something in San Francisco. And you sort of look at these at two different organizations that might both have good, well meaning people and like, you know, the organization that moves quickly, it's like, it's like orders of, it's like an order of magnitude faster. It's not like 20% faster. It's just amazing what you can accomplish. And so maybe the sort of slightly more positive way of articulating this is, I think that people are often capable of so much more than they believe themselves to be capable of. And so if you can sort of challenge them about the perceived constraints on the problem and explain to them the impact of being able to do A and B and why, like what happens if we could do A and B? Startups are somewhere between completely impossible and very, very, very, very hard. And there's such a narrow ray of light that passes between those two. The companies that make it through, usually at multiple points in the journey, find ways to do things that are seemingly impossible. And it is, you have to sort of acknowledge that what you're asking for is like really hard. And you understand that. And it's just there's no other way, you know, and so let's sit down together and think about whether it's possible. And sometimes people find clever solutions or new reserves of possibility to kind of get there. And if you kind of do that enough, it compounds and like, you can accomplish a lot more than the company that isn't doing that.

I had a line where somebody would bring me something like that and I would say, when Moses came down from the mountain and he had the tablet, Was there an 11th Commandment that we all missed that we couldn't do this thing we're talking about right now?

Yeah, exactly. You know. Yeah.

Like it's not. It's not a law of physics. We can figure it out. Okay, I hear you've got something like 40 or 50 ex founders on your management teams in your company. What's going on with that? Why are you doing it? How do you manage that? Chaos.

I think it's actually a lot more than that now. Okay, but why. I think that.

Are you aqua hiring or hiring? Like, what's the. What's the.

Sometimes we acquihire, sometimes we hire. It's. It's a profile that we look for, you know, rippling. You know, we sort of coined this phrase. I know HubSpot. HubSpot's been doing this for a long time, but we coined this phrase of like, compound software.

You know, I'm really mad at you about this.

Yeah.

Because we are compound star. But we never came up with a clever name like you. It totally stuck. Yeah. And everyone's like, Parker's the original. Like, we're the original compact subspot was.

Doing it long before us.

Well done.

But the reason that we do this is because I'm convinced that this is the right way to build software and that actually we've been building software wrong for a couple of decades now. And most people believe, yeah, yeah, you're doing compound software. There are some, like, sales and marketing advantages to building, you know, good enough, but integrated products. And that's not it at all. I think the belief is that actually you can build better products by building them in this integrated way. And you can do it because the fact that these things are deeply integrated and seamlessly interoperable on its own makes them better. But also when you're building across multiple applications, you can afford to invest much more deeply in a set of capabilities that are common to all of the applications. Things like analytics and permissions and workflows and custom objects and stuff like that. But I think a lot of, you know, and this was sort of the original, like, before we were this articulate about what we were doing and why. It was one of the original founding principles of ripplane. Was that we were going to do more things, not less. And this focus thing was bullshit. And like, you know, that was like what David wanted us to do, but that's completely wrong and we should do it this way. And so a lot of same with HubSpot.

We're like, this whole focus thing, like, just do one thing really well. We were like, nope, we're going to very thin, but we're going to get to table stakes at some point. It was the exact same thesis we had.

Yeah. So.

Yeah.

But a lot of the history of the company is trying to figure out novel solutions for the very real challenges with that approach, because there are a lot of reasons why it is easier to focus on one thing. Along the way, a lot of problems come up and there are bottlenecks that develop in different parts of the organization. And one of the places that a bottleneck forms is really at the level of sort of executive attention around these things. And so you end up needing people who can be like the CEO of these products or who can drive things forward, who can find a path. Because a lot of people who are very good managers and executives and engineering or product or whatever, what, what they do is they. They come to you with problems. And so they say, there's a series of gaps we have. Like, in order to win, here's like a long list of things we need to do. And they unroll the list and it rolls out onto the floor and goes all the way down the hallway, you know, and, and like, we've prioritized it by sort of most important on, on down. And I have a team of this size, and this is about one quarter's worth of work is like, you know, these things this far down the list. And so we're going to do one quarter's worth of work and we're going to solve these things. And, and, and that's what it is. And the problem is, is like, yeah, but the list goes all the way down the hallway. And. And they're like, well, but my job is to sort of, you know, that's your problem, right? You're like, you're like. And so they're asking you to find a way to make ends meet, because their job is just to kind of move down the list and then you're still fucked. Because at the end of the day, they're going to do those things, but you still haven't solved the problem, which is like, you need to win. And so you need people who can find ways to do the impossible that sort of understand look, the CEO that's asking you to do unreasonable things, I didn't create this situation. The market created. Like, this is the reality that we find ourselves in, which is like, we need to do these things and if we don't, we're dead, we're screwed. And so we need to find some way or some alternate path or some sort of, you know, there needs to be some effort to solve the whole problem or like, it doesn't matter. You know that.

And you think X founders are particularly.

I think ex. Founders understand breaking the laws of physics or they just, they've been in situations where they've, they understand that. Like, yeah, like, it's like we either, you know, they've sat there and stared at the dwindling bank balance while, you know, while the sales isn't working and they're like, oh. And like, and they understand that. Like, yes, it's absolutely true that, like, you know, this is a reasonable set of expectations for the team this week, this month, this quarter, this year. And yet if we do the reasonable set of things, we're dead. Yeah. And so we can either give up or we can try and find a way to accomplish an unreasonable set of things.

How do you manage them, though? Founders are typically a little unruly. Want a crap ton of autonomy. Often don't play that well with others. Like, how do you manage the chaos?

I don't know if I found that to be the key because, like, you know, if you're, if you've started a company, I mean, look, there's all kinds of people, but like, you know, man, like you've got to convince a bunch of people to work for you, you know, that, you know, when it doesn't make any sense, you know, and like, there's a certain amount of charisma or interpersonal skills that you've had to, like, develop. Like, even if you didn't have it, I think that, that most people are more, well, socialized than that. But they're always, I guess, exceptions. And, and we do give people a lot of autonomy because, like, the best thing in the world for me is someone who can run with something, you know, and, and sort of take it off my plate. Like, that's, that's ideal. So everyone, everyone's aligned. Yeah. On there being that kind of autonomy.

Just switching gears briefly. Deal, your main competitor. Been a lot of drama around it. Do you want to talk about it?

Sure. Weirdly, I would say deal is a competitor, but probably not the main one. You know, the companies, you got a lot of Them. Yeah, there's a lot of, you know, if I was like, who's our main competitor?

Space?

I would be like, man, you know, in payroll, it's probably Paycom, Paylocity, adp, you know, workday for hcm, maybe, you know, Gusto down market.

Yep.

You know, we. We come up against Deal in specifically this sort of global part of the business where you're. I need to hire someone in XYZ country, and I have like one or two people that I'm hiring there, and I don't know anything about it and need some help. But, like, that's where we compete with them. But. But we have, you know, much, much stronger competition. And with these other companies, it's just that this weird stuff happened with them.

Tell me about it. So when was the first inkling you had that there was a spy, that someone was spying on someone from Deal was spying on your company?

The weird thing about Spy is Spy makes it sound.

It's great. It's a podcast.

Sort of sexy and fun.

Yeah, that's the idea part, which for podcasts, great.

But I think it's really, like, it's not the deal with Spyence that they were stealing. It was just theft, pure and worse. From the CEO of the company. Yeah.

Source.

And the thing that happened is we got a reporter who was writing a story, sent us a bunch of rippling internal Slack messages, many of which were sort of cropped in sort of unflattering ways and taken out of context, and was asking for a comment on it. And just, you know, because of the context, it was. It was very clear, for a bunch of reasons when you thought about it, that the only place that this could have come from, like, it had to have been Deal. Like, no one else would have sort of known to send this stuff to that reporter. And so the implication was the Deal had, you know, full access to our Slack. And then from there, you know, we. So we sort of knew what was going on immediately.

But even before that, did you have an inkling, like, in some territory that they were winning an unusual number of deals and, like, how are they doing it? Was there an inkling before that?

They're really, you know, once you started looking, you know, there were these examples. There were, like, when this story came out, you know, there were customers that wrote into us and former customers, you know, that. That wrote into us. And there was. There was a guy that was a former Deal customer that took a demo with Rippling and was talking with us, came to us because he wanted to switch and he spoke with a Rippling account executive. And within hours he got a WhatsApp message from Alex Boozes, this CEO of Deal, you know, who he didn't know, never met before. There was like, hey, I hear you're like, you know, looking at other stuff. Like, you know, let's try and find a way to get you to, you.

Know, like, seems like an awful big coincidence.

Yeah. And he emailed at the time and this was before we knew anything, anything was going on. He emailed his rep and he was like, whoa, this is super weird. Like, this freaked the hell out of me. Like I, you know, how did, how did Deal know that? Like, you know, and of course the rep thought nothing of it. So it didn't go anywhere. Right. Until later. You look back and you're like, oh yeah, you can actually trace the person that was a Rippling employee that Deal started paying to send them all of this internal steel. Rippling internal data, including mostly like CRM data. Just like every opportunity we were working, every customer we were talking to, the pricing we were offering them, the objections they had, you know, it was just every single day just sending all of it directly to Alex. Disease.

Do you think Alex and crew targeted someone or took an employee and got them to work for you or. Or there was somebody working for you that they got to Ladder. They co opted somebody.

And you know, the thing is that hasn't been talked about a lot is it really seems like it was, you know, wasn't wasn't just us. There are a bunch of other companies. So, you know, there was.

That they were doing it too. Or in the industry writ large. Is a lot of this going?

No, no. That. That Deal was doing this.

I see.

You know, like we were not the only ones.

Yeah. And it was a defined play.

Yeah. I believe that that company was built on this foundation of theft from competitors and that that was like a critical component of what they're doing. And so, you know, one of the things that we decided to do is we decided to be extremely public about this and come forward even before that.

So you get this thing from your press guy. Like they have to have access to our.

Yeah.

And then you ran a honeypot operation to kind of prove what you thought. Can you just talk about that meeting and what was going on? Can you just give us a glimpse behind the scenes of what happened in that meeting?

Well, so actually first, before that, what happened is we needed to figure out like, who was doing this. And my assumption was that this was probably a former employee that left you know, because sometimes people leave one company, they go to another, and sometimes people like, you shouldn't do this. It's wrong, it's illegal. But sometimes it happens that people take some stuff on the way out. And so I was like, maybe there's someone who kind of like, you know, did, did their new employer a favor on the way and sort of unethically, instead of, you know, what, what we would do in a situation like that is we would say, whoa, whoa, whoa, like don't, you know, delete that. We don't want, you know. And unethically they said, goody. You know, like, great. And then what we did is, you know, the sort of light signature of the behavior that really popped up was the search history in Slack. Like what, you know, there were certain searches that this person had to have been doing.

Did you invite your IT guy in? Like, how, how did it.

Well, so this is the crazy thing is the search search logs in Slack are not visible to Slack clients.

Oh, you ping Salesforce.

And so, and in fact, like, cynically, I think they were doing it in this way precisely to avoid detection as they were doing searches and then getting things from. Not joining the channels, but getting things from the preview from the search from the actual searches. And so really the only way we were able to do this is we got introduced to some like, very senior people at Salesforce who like, to their credit, you know, sort of agreed to help us track this down. And they, they pulled from their own internal logs what this search history was. And it was very clear exactly who the person was. And that person was still an active, rippling employee.

Who is the one who came up with the idea to look at that particular thing, to look at the searches? Yes.

I can't even remember, but it was so obvious.

It was like you called a meeting of a bunch of smart people and like, how are we going to catch them?

It was like, I mean, it was a very small team. It was like, you know, it was like, you know, me, my, my general counsel, like, you know, the deputy gc, you know, it was like a couple. It was like two or three people on legal, two or three people on security. And it was like, hey, how are.

We going to catch them?

You know, to, to get this in this, the slacks that we saw, they must have done these searches to get, you know, so yeah, we, and these are weird searches, like someone. And so we've got to be able to find this. And so then we clearly was one person that was like doing this. And it was very Clear who it was. The big kind of insight was like, well, look, it's actually because we were thinking like, is there something that we could do where we could put something in slack, you know, like maybe like put like a fake customer in salesforce with a phone number that like goes to our law firm, put that in slack and like, see if a deal sales rep calls that phone number, you know, and like kind of triangulate that way. It was just. It was too hard to sort of know because it was too hard to see what deal would be doing with it. And so the insight was realizing that you could flip it around and you could actually the thing that we could see was the searches. And so we could see what this guy was searching for. And so we had to do it the other way. We had to give some information to deal with and see this guy searched.

For how did you get the information to deal?

So, you know, look, a lot of companies that are in competing spaces have some somewhat regular exchange of like legal letters where, you know, for whatever reason, you know, they send you a letter and they're like, we're angry that this person joined and make sure that they're, you know, or this person recruited someone they weren't supposed to recruit. And you know, and so this is a certain sort of fairly form. There's a sort of low level of that that was kind of happening. And so there happened to have been a letter that they had sent us about something or other related to a deal employee that had joined rippling that we had, you know, sort of, I think at the time had decided we're not even going to bother responding to this. But we suddenly said, well, let's respond to it. And when we responded to it, we said, okay. We decided to put together like a screenshot of a slack message that was like basically like a fake slack message. Although to make sure that it wasn't actually fake, we actually had someone send that slack message so we could be like, no, no, it was a real slack message. But we put this thing together and the slack message, what's actually the funniest part of this is that initially this was designed by the legal team. And man, the slack message was so boring. It was like no one would have cared. It was so uninteresting. And so, and this was a very closed circle of like, you weren't allowed to tell anyone about what was going on. And so I called up our former cmo who was like, that he had moved into a new role at rippling, but he was like, One of the things about him that's so amazing is he's, like, just great at writing, coming up with, like, cold email messages. And so he was always the guy we went to when we needed, like a new cold email to send people. That was good. And so I called up Mepstein and I said, mebstein, we need you to write a cold email that's going to have a 100% S1 to S2 conversion rate that like, like, definitely someone's going to have to click on this. And he came up with the actual thing. And it was this message that sort of suggested that there was this channel in rippling Slack called D Defectors, where ex Deal employees were talking about Deal maybe in ways that were unflattering. And there were, you know, we sent them the message and then just for added sort of theatrical effect, we like, blacked out, like, key parts of it, you know, to just be like, really be like, what are the blacked out parts of it? And it was included in this letter that we sent to their CFO, who is, you know, the CEO's father, and their outside counsel and their head of legal. That was the sort of person's title. So there's only three people. One of them, you know, presumably it's not the outside counsel, and then the other two are quite senior within the company. And we sent them this letter, you know, at like, I think it was like 8pm and then we waited. And I remember waking up at like 4 in the morning and checking my slack, and there was just all these messages. It was like, holy shit, it. They did it. And like, we were getting.

Somebody was searching on that channel.

He was searching and going in, you know, this. Going in this channel. And like, you know, it's a. It was purposefully a weird search term. It's never been searched before. We checked, you know, it was not a real channel, you know, so there's only one way that this could have happened.

Okay, now you know who it is. Your month and a half search is over. Then what happened?

Well, then, you know, who approached him. So this. The. The employee was. Was based in Ireland.

Yes.

And Ireland has. The Irish legal system has an extraordinary form of relief in civil litigation that allows you to file an ex parte process. So basically you can. You don't have to alert the other side. You can go to court and get, without the other side being aware of it, an order from the court that's effectively sort of like a warrant, you know, in the US Legal system that exists in like a Criminal case, but not in civil litigation. And so we were able to get this because of the sort of strength of the evidence that sort of there was a court order to get access to this guy's phone. And so there was a court officer that came to.

Police officer. Ish person.

I don't know about police officer, but court officer. It was like a solicitor is the uniform. I actually don't know. But, but in, in, in the Irish legal system, they're solicitors and barristers and, you know, and so maybe more like.

A lawyer wearing a white wig or.

Man, I don't even know now I'm going to look that up. But anyway, you know, they showed up at the office, met this guy, was take, you know, sort of, you know, went into a room for a meeting and there was this team raid with, you know, sort of forensic IT people. The sort of officer of the court said, look, I've got this order for your phone. And he sort of said, I don't have my phone with me, I need to go get it. That turned out not to be true. And then he sort of, while he was like going to get it, kind of ran into a bathroom and locked himself in the bathroom. And what we later learned is that in the bathroom he did a factory reset on his phone, tried to flush it down the toilet and then came out of the bathroom. And, you know, the, the court officer was telling him, look, you're violating the court order. There's, you know, this is something that you can be in prison for. And he ran out of the building and took off. Yep. And then, you know, over the next sort of 10 to 12 days, there was this sort of sort of ongoing legal process to try and get, you know, sort of like real, like police enforcement of this to get this guy to, to get a lawyer to sort of and, you know, get like contempt charges filed. And eventually what happened is, is he, you know, sort of facing, you know, sort of these legal consequences. He eventually sort of like turned and sort of started cooperating and said that he had destroyed his phone. But he also, he told us, and this is all, you know, in the sort of, the sort of court proceedings and the affidavit that he produced. But according to these proceedings, you know, allegedly what happened is that he, immediately after he left our office, he got called. Alex, the CEO of Deal, told him what had happened. Alex said someone would reach out to him, you know, allegedly. And, and, and then two attorneys at Deal, like employees of Deal, who were attorneys, called him back and they told him to Destroy his phone. Which is like, if you're, that's a, that's a bad thing for anyone, but it's really bad for attorneys to be, to be saying that, told him destroy his phone, get a new burner phone, call them back, delete all of his accounts. And they offered to relocate him and his family to Dubai and get him out of the country. Dubai is no extradition, you know, like, not a lot of extradition options. One of those lawyers, by the way, who was based in the uk, practiced law in the uk, has since relocated to Dubai himself. I see this all came out. And so there was, and so there was this crazy thing where he detailed, you know, like the, the person who's doing this detailed exact everything that happened and how he was recruited by the CEO directly and sent all of this information as CEO and was paid, how he was paid and sort of all of this stuff.

Do you think this is going on a lot in tech?

I don't think it's going on a lot. And look, I think the reason that we really came forward with this.

Yeah, you went very public.

Obviously there's a reason for rippling for the business. We need to defend the business. But more importantly, I do think that if deal sort of moves forward, like in a way that's unscathed, there is this risk that the Overton window shifts and that this becomes a norm. You know, that it's sort of like, ah, you know, your competitor paid someone to steal your CRM data. If you can't stand the heat, get out of the kitchen. You gotta be doing the same thing and everyone set a precedent and everyone's gotta have an S espionage team and a counter espionage team. And, and, and I just don't think that that's the, that's not the way I want the world to work.

Okay. Anything else you want to tell the audience? Any other advice you would give to founders and people who want to go from four people to 40 to 400 to 4,000 and 40,000 someday?

I think like everyone kind of needs to find their own path through this stuff. It's one of the things that's, that's kind of hardest. Like, I don't, I don't really think that there are a lot of rules and recipes. And so, you know, it's why I probably have like a lot, a lot more. You know, there was a point in my life where I was like very angry at investors and, and I think I've sort of, sort of reached some point where I actually have a lot of Empathy for investors and, like, how hard it is to be in. In their position and. And how impossible the job is. And. Because I think it's really hard, you know, even if you have a lot of experience yourself, you know, there are, like, people all find their own paths and things change. Like, Rippling was like a business that was like, so close to what we were building at Zenefits. Like, it wasn't. Was the same industry slight, slightly tinkered with, kind of the sort of principle, kind of the foundational principles of sort of what we were building. But, like, the world was like. Like four years into the future from when I had started Zenefits. And that one thing, like, changed everything. It was like, you know, all of the things that, you know, or many of the things that had worked for us at Zenefits didn't work at Rippling. And like, you know, just like. Like everything was different because of a few changes to the starting assumptions. And it really sort of made me realize why so much of the advice that people give out about how to do this is so useless. Because everyone is fighting yesterday's war, you know, from their own experience. And, like, things are very different. You know, things have changed just because of the slow advance of time, if not because this is a completely different business in a completely different industry with a totally different set of people. So it's a real struggle. And it's probably one of the reasons why I'm like, man, it sucks. If you have any other thing that you can go do, maybe that's the right thing to do instead of getting involved in this whole thing.

I appreciate you. Thank you on behalf of the listeners. You're an inspiration to many. Congrats on all your success. Congrats on your revenge tour.

Well, thank you very much.

Appreciate you. Okay. Hope you liked that interview with Parker. I really liked it. He's a smart guy on hiring. He's got a bunch of cool ideas, some of which I'm definitely going to borrow. I like his idea that if he's got a candidate that's coming to meet him, he sends them an old board deck or his investor memo, lets them read it, and he spends, like, the first half of the interview just talking about that. And the reaction of the candidate to that memo and the ideas they come up with really says a lot about them. I love that he does that. He relies a lot on reference checks. He does something interesting there. He asked the candidate to give him six references, which is kind of a lot, and he only calls two. He's Trying to figure out if they have six references or not. But then he leans much more heavily on the blind references. And this is something I did as well. I would say 60% of my decision criteria was around the third party references of people who used to work for them. So I thought that was interesting. This is something we didn't do at HubSpot, but I really liked how he hires a lot of ex founders. And he talked about how ex founders are used to breaking the laws of physics. They're used to just really tight constraints and having to really do hard things. And so he has this sprinkled throughout his org and he's had a lot of success with them. He likes his senior team to be a mix of homegrown talent and Bend, their dumbbeck talent. And this is pretty consistent across most of the CEOs I interviewed. And I feel like it's a little bit of conventional wisdom and scale up land that you just hire a bunch of bend there done that people. I'm not sure that's right. A lot of HubSpot's team over the years was 50% homegrown and 50% been there done that. And that mix I think is just about right. I took some things away from on pace. He's at 4,000 people. A lot of companies slow down when you hit 4,000 people. He seems to be keeping the pace up and he does a few things that I think are smart. And a lot of the CEOs I interviewed do a couple of these things. First, he really tries to stay on the coal face with the customer. He's one of the most active users of Rippling, the product. He runs payroll for all 4,000 employees at Rippling. So he seems very close to the customer experience through that. He stays on the coal face with the employees too. He sits right inside the engineering organization where you can see what's going on, hear what's going on. And he talked about the CEO sets the pace. CEO slows down, the org slows down. CEO speeds up, the org speeds up. One of my big takeaways on Parker is he doesn't have a chip on his shoulder. He's got a boulder on his shoulder. And that boulder really drives him. He calls it his revenge Tour the whole company. I think this is pretty common amongst some of the best CEOs and can be a real motivator. And in his case, David Sachs put a boulder on his shoulder. I have a chip on my shoulder and I had an old boss put it there. I had a guy I worked for, for a decade. When I went to resign, he said, you'll be nothing without me. And this is like 30 years ago and I still remember. And if I really want to get fired up, I think about the day I resigned from that company. So Boulder on the shoulder. Super useful. Channel it. I think it can be really useful for you. My last thought on Parker and about scale up startup land writ large. I meet with lots and lots of founders these days. There's a new breed of founder I call five Tool founders. Now a great baseball player can hit, can hit with power, can catch, can run and throw, all at an elite level. And I'm noticing a new breed of founder who is kind of like that. And I think Parker's one of them. I think Brett from Sierra is one of them. Mati from 11 Labs, Gabe from Rogo, Dara from Delphi, where they're very good at coding, they're very good at design. They have vision, they can recruit and they can sell. Those are all five tools that they have in their bag Tag. And I'm noticing more and more of them. And if you're one of those founders that's deeply technical like them, but can't quite storytell and sell, I would work on that and get some coaching on that and get some feedback on it because those five tool players are worth their weight in gold. And if you can be a five tool player, that really opens up a lot of doors for you. Okay, those are my thoughts. Lots of takeaways from Parker. I'll see you on the next episode. Sat.