Parker Conrad, founder of Zenefits and Rippling, recounts his dramatic ousting from Zenefits in 2016, which he attributes to three exaggerated media narratives. The first involved insurance licensing: his lawyers advised that representatives didn't need licenses in all states, a mistake later fixed to over 95% compliance. The second was a "macro" script he wrote to avoid manually clicking a button for 18 hours during an online licensing course; he argues it wasn't cheating since he scored 94% on the exam. The third was an alleged party culture, sparked by a used condom found in a shared building, which the media sensationalized. Parker claims these were pretexts for his removal by investors, particularly David Sacks, who issued a different press release blaming Parker for compliance issues. In reality, Zenefits faced genuine business challenges like declining growth and negative gross margins. Parker was legally gagged from defending himself because the company controlled attorney-client privilege and legal fees. He believes Sacks scapegoated him to avoid personal blame, as most compliance failures occurred under Sacks' own management. Despite the turmoil, Parker went on to found Rippling, another successful unicorn.
I'm Jessica Livingston and Carolyn Levy and I are the social radars. In this podcast, we talked to some of the most successful founders in Silicon Valley about how they did it. Carolyn and I have been working together to help thousands of startups at Y Combinator for almost 20 years. Come be a fly on the wall as we talk to founders and learn their true stories. Today we're talking with Parker Conrad, who founded Zenefits in 2013 and Rippling in 2016. Two startups that went on to be unicorns. YC funded both. Parker's story is one of the most dramatic you'll hear on this podcast. So buckle up because here we go. So Carolyn, today we're talking with Parker Conrad, the CEO and co-founder of Rippling. And the story of Rippling is very much intertwined with Zenefits, the company he started before that. For listeners, Zenefits handled payroll, health insurance, and employee benefits for businesses. And it grew very fast and was a big media darling, but by 2016 Parker, you'd been ousted in what was essentially a palace coup. And then the press tried to paint you as this tech villain. The press had a list of bad things they attacked you for and they were all bullshit. Can we just dive right in and have you talk about what these things were and what really happened? I think there were kind of three things that sort of ended up being in the media about Zenefits. There was this thing about insurance licensing for our reps. There was this thing about the macro. And then there was the supposed party culture of the company. And there were three sort of very different things. So I can talk about them each in turn. But on the licensing side, the people at Zenefits were for the most part properly licensed in their home states. But they weren't licensed in other states around the country. The company was, but the individuals weren't. The simple reason is that we didn't think that they had to be. And we didn't think they had to be because that's what our lawyers had told us was required. And by the way, what happened is at a certain point our lawyers had looked, you know, regulators are really pushing back on this. Is this really something we want to we want to fight on? Why don't we just get everyone licensed everywhere? And we did and sort of in the last year that I was at Zenefits, the compliance with the specific out of state. Licensing rules went to the over 95% and getting your license actually once you have it in your underlying home state, getting your license in these other these other states around the country. All you have to do is you go to this website, you swipe your credit card, you pay like 75 bucks, usually. And now you have your license in the other state. And so there's no additional training required. It's really just it's an occupational licensing requirement and a licensing fee that you need to pay. And there was like zero benefit, you know, this is not a lot of money. There was zero benefit to the company of, you know, not getting people licensed like this wasn't. It wasn't like a part of our business strategy, you know, it wasn't like Zenefits's model is like, you know, screw the occupational licensing rules around insurance license, you know, it was just a mistake. Because your lawyers advised you that it didn't matter. Yeah, I think I think there's just a different sort of moral character to making a mistake like this. Then, you know, sort of going out and, you know, sort of like saying we're going to undermine the sort of licensing regime. And so what happened is we got, you know, while I was there, we got to this point where we will, you know, everyone was licensed everywhere. But at the time, Zenefits was by some measures, the largest small group insurance producer in the United States by the volume of sort of new business we were writing. And so I hired PWC to come in and basically audit all of that and sort of figure out for every deal that we had done, what was the sort of provenance of it. And then we decided, look, what we're going to do is we're going to go to regulators. And we're going to say, look, Mayakulpa, we, you know, we sort of thought the rules were one thing. We understand that you guys view them as being another, you know, here, like we're coming to you with sort of like an accounting of all of this. And we want to pay some fines and move on. And that was the plan, you know, sort of we were preparing this. We had sort of, you know, meetings with the board kind of every other month to go through this and go through progress on this right up until the day that I left. And on the day that my departure was announced, you know, we had drafted this sort of, you know, mutual press release that sort of said kind of, you know, the same sort of anodyne things that you always say when someone leaves. And, you know, sort of mutually on both sides, like, you know, sort of appreciation and that sort of thing. And then the company just issued a different press release. And it said, Xenifits had these compliance issues because this this parker guy didn't care about compliance. And that and he's the issue, but now he's gone. And then it sort of continued from there. Do you know now what happened between the review of that press release that everyone's like, this is the one. And then there's this period of time and then this other press release. Do you now know the sequence of events that led up to the second press release? What I was told is that there was just always a plan to issue a different press release that there was this sort of kind of sort of fake exercise with, you know, this exercise with me and Kim from Andreessen Horowitz and David in the background drafting this press release that was never going to be issued. And for the listeners, that's David's acts. Okay. Got it. Because they needed a scapegoat. Why they decided to go in this direction like I, you know, I don't to the state, I don't really understand. One of my like firm beliefs is that, you know, when I left, I thought that Xenifits was going to be really successful. And I thought, look, you know, the company was facing just enormous commercial challenges, you know, like a lot of our growth had sort of started to evaporate. Things that were working for us top of funnel had sort of had gone away. You know, we were missing our plan, you know, investors were frustrated. We were upside down on gross margins. It's my belief that like, you know, in retrospect had I stayed. I would have been able to kind of turn it around. And I thought when I was leaving that by not sort of getting into a war with the investors, I was sort of leaving, you know, like David, like maybe David would figure out the sort of commercial side of this. But what happened instead is David sort of became the company's chief antagonist and was sort of going out and saying, you know, as CEO, like this company's unethical, you know, they're, you know, doing all these bad things. And it was really hard. The company didn't recover from that. It didn't, you know, it didn't make the company successful. It's sort of like Barry dead. And I don't, to this day, I don't really know why. I mean, I have, you know, kind of like my own theories. But one of the things my theory on this is that David had this sort of artful way of describing the licensing issues and the compliance issues at benefits. And so there's this video of him at TechCrunch disrupt. He was talking with Connie Lazlos about benefits. And he has the slide and a deck that he presents where he sort of had three bullet points. And the first bullet point was I'm paraphrasing here, but the first bullet point was like it's no secret that's benefits has, you know, huge compliance issues. And bullet point two was the culture of the sales organization is broken. And bullet point three was the sales organization always reported directly to Parker and not to me. And the sort of implication of that sequence of bullet points was that the compliance issues were on the sales team. And that actually wasn't true. It was sort of an artful kind of lie. And most of the compliance violations as it turns out were on the account management team that reported right up to David. Like, look, a CEO. I'm responsible for the whole thing. So I'm accountable for, you know, the misses in all parts of the company. He was sort of always sort of strange to me that like David was attacking me for these licensing failures. 70% of which happened in, you know, his org. And while he was he was running it. And that was like a very closely guarded secret. And I was under like enormous legal restrictions. And was well, I wasn't allowed to talk about it. So, you know, I would meet with regulators and Zenefits would send their attorney to those conversations with regulators. And they would they would ask me like, why weren't people licensed in in these other states like what led you to believe that was OK. And the benefits attorney would step in and say, well, that's attorney client privilege communication. You know, we object to Parker answering the question because that touches on advice that Parker got in his role as CEO of the company. And because it was advice that he was getting a CEO of benefits, this is a privilege and attorney client privilege communication that benefits owns the privilege on not Parker. And so we don't want him disclosing that. And my lawyers explain to me, look, you can't you can't disclose it. And if you do that, you know, the company will sue you. And you know, they'll stop stop paying your legal bills. I had sort of an enormous number of legal bills all of a sudden and really didn't have the financial resources without the company sort of paid for it to defend myself. And so, you know, I kind of didn't have a choice. I had to sort of, you know, keep it, you know, zipped and go from there. That really kind of never came out in all of this. David emerged from zenefits as kind of the white knight of compliance. And I'm sort of guessing at this, but I think that in David's view, you know, there was some something that would attach itself to him. I don't think that David was out there to sort of purposefully, you know, screw up compliance either. I think it was a mistake. But I think it might have looked like, hey, you know, you know, he David, you were CEO.
of this company, your lawyer, why weren't you on top of this? And I think he managed to sort of extract himself from the situation without that sort of becoming part of the narrative. And I think that's why he did what he did. So the second piece of this is the macro. And what the macro was is when I was first applying to Icommonator, I needed to build a prototype. And to do that, I needed to get my insurance license so that I could get planned data and pricing information from insurance carriers. And to get your insurance license, one of the requirements is you need to take a course. And this course is offered by a couple different vendors, but one of them is Kaplan. And they have an online version that you can take. And when you take this online course, you sort of click through on their website, these pages of content. There are a few paragraphs on each page. There are like hundreds of pages across the course. Every few pages, there's a short quiz or exercise that you take. And at the end, you take a proctored in-person exam. And I got like a 94% on the exam. I knew my stuff. But at the end of the online course, I got to this blank page that had this timer counting down. And it said something like you have 18 hours and however many minutes remaining. You have to stay on this page until the timer is complete. After five minutes, this sort of dialogue window opened up and it said, hey, it's been five minutes. Are you still there? You'll be logged out for inactivity, click here to stay logged in. And so I click there and I sort of suddenly realize, like, man, I have to stay here and keep clicking this button every five minutes for like the next 18 hours or whatever. That's crazy. Because it says you must be doing this for 40 hours or whatever. It's right. There's a minimum. It's like 40 hours or 52 hours or something like that. And so I kept there clicking that button for hours. And eventually what I did is I wrote a three line script. And what it did is it clicked, I'm still here. Then it waited five minutes. And then it was like go to line 10 and repeat the process. And all that it did was maintain the session and kept you logged in. What's important is what it didn't do. It didn't take the test for you. It doesn't give you any of the answers. It doesn't advance you through the course content. It just kept you logged in. And I thought I had hit like a bug in the system. I didn't think that anyone really intended or wanted me to sit there clicking that button for 18 hours. It turns out that's exactly what they want you to do. And so that was the macro. And that ended up getting described in a lot of the media reports about this is insurance fraud and cheating on the licensing exam and stuff like that. And I think it was naive. I obviously wish I hadn't done it. But again, I think there wasn't-- I don't think it was-- there was no intention to cheat anything. And I think that, like, look, my view is I knew my stuff. I passed the test. I got a great score. I had done put in the work to understand how this all worked. And in sort of all of everything else I've done at school and academically, skipping ahead or learning things in less time has always been something that's celebrated and not something that you get punished for. So I can clarify, any reasonable human being is not going to spend 20 hours hitting the refresh button for every five minutes so that they don't get logged out. It's just ridiculous. So I just think what you did was something any reasonable person who was capable of writing a script would have done. People who take that test probably pay their children to keep clicking the button. I mean, it's obvious no one's really sitting there. And so that clarifies that. You said a third thing, party culture. The third thing that came out about benefits was this party culture at the company. And what I'll tell you about this is it's just complete BS. I don't want to say there weren't issues with the culture at benefits there were. And a lot of them had to do with just the overwhelming amount of work that people were taking on. And sort of there was a real burnout culture at the company. But there really wasn't, like, as far as I could tell, like a huge party one. And like, look, we had beers in the office. And 8 PM on Friday, people would get together and have beers with their colleagues. But it was 8 PM on a Friday. And most people were still at work. And where this came from is there was a Wall Street Journal article. And sort of the origin of this Wall Street Journal article is that the landlord of our building at 303 Second Street in San Francisco sent an email to our office manager that said, hey, we found a used condom in the stairwell, in the sort of line that you guys are in. Can you please tell your employees that this is completely unacceptable behavior? And unfortunately, our office manager sent an email out about this to 1,600 people. And one of whom ended up fording this along to the Wall Street Journal. And it became a really big story. The thing is, and that story, by the way, got written and rewritten and rewritten. Oh, yeah, that's juicy. Sex and the stairwells of-- high-flying-- orgies at high-flying tech startup. And the thing is, they're like 30 other companies in that building. It's not even clear that it was someone that-- It's not even clear it was someone in the building. Let's be honest. Like, could it have been anybody? I don't know. But that became this sort of scarlet S that was sort of came to really define the company in the media, even though I think it was really just sort of completely inaccurate. But those were sort of the three sort of big public controversies at Zenefance. It was the licensing, the macro, and sex and the stairwells. OK. Well, I am really glad that we got to the bottom of all three of those things. Let me just also say this is-- you're not saying this, I'm saying this. Like, press, as we know, Carolyn, are eager for stories of founders misbehaving. And if they can latch onto anything, they'll twist it. And they'll keep reusing it. And I mean, can't tell you how many examples there are of some lie that was told about someone at YC that's just perpetuated over and over. And then it appears in the New York Times or the Wall Street Journal. And now it's a fact. With all these three things, do you think that David Sachs or the board or whoever made the decision sort of used these blown out of proportion stories as a pretext to oust you? Zenefance had some very real problems. And the very real problems were about the business and the financials of the business. They all really stemmed from, I think, this original sin decision that I made at the company, which was in the early days of Zenefance, everything was working so well for us. I mean, I had come from a company before Zenefance where, man, we would try sort of five things to try and get customers. And four of them would fail miserably. And one of them would mostly fail, but would work just enough that it would sort of inspire us to keep going for another six months and pivot the company and try and get something to work. And we kept doing that for seven years before I left and started Zenefance. - Wow. - Then at Zenefance, it was like the complete opposite. At Zenefance, it was like, we would try five things and they would all work. And we would try two things that we thought would never work. And those would kind of work too. And so as this great example of just, you know, what things look like when it's working and when the market is sort of sucking the company into the market or the void is kind of sucking the company into the market. And so our biggest fear was that actually, you know, there were gonna be fast followers that there were gonna be other companies. We had sort of uncovered this pot of gold. And there were gonna be other businesses that were gonna sort of establish a toe hold. And I thought that we really had to sort of suck up all of the oxygen in the room. And basically say, look, we've got to soak up all the demand. We can't leave room for someone else to come in. Because if we do that, it's unclear when things like sort of settle out. You know, at some large scale, we thought there were gonna be network effects in the business, but it was not super clear. Like if someone else was willing to push the gas pedal all the way to the floor, would we even be, you know, having discovered the market? Would we be the ones that the sort of lens of the market was centered on, you know, at the end of the day, if we weren't able to sort of grow and sort of take up, you know, all of the oxygen in the room? And so we made this decision, the sort of insight behind Zenefits was really that, you know, there was all of this, it before Zenefits, you know, companies tend to have multiple systems for HR and benefits. So they would have, you know, something for payroll, something for 401K. You know, most of the sort of for small businesses, most of the stuff around insurance was offline. And you handled it via the fax machine. And so you'd have to fax it in application for medical insurance, for dental insurance, for vision insurance for each employee. And so we sort of said, look, you can put the insurance pieces online and then you can do all of this together in one place. And that just dramatically cuts down on the administrative work required for people to run the HR systems within their company. And so what we said we do is early on, we said, look, companies have all of this administrative work. We're going to take all of that administrative work on ourselves. We're going to do it for them behind the scenes. And over time, we're going to work to automate it and work to sort of put it all in software. You kind of had to do it that way because the insurance companies didn't have like good systems. You know, you still had to interface with them via the fax machine off at midnight.
manually. And so it created this, it meant that Zenefits was sort of secretly behind the scenes, you know, this giant sort of operational machine. And there were kind of two problems that that or a couple of problems that we faced with that. And one was that when you scale something up with manual ops, it's very hard. It's much harder to come back later and automate it. If you sort of start with automation, you can gradually scale out the automation over time. But the system, it just kind of grows too complicated when you start with ops and it gets really big to come back. And so the automation was constantly running behind. You know, we had these estimates on like when it was going to be fully automated and it was constantly getting pushed out. The second problem is that whenever you're doing something manually, there's an error rate around that. And so what customers started noticing is that, you know, in that error rate, if you're really good, it might be 99, you know, you might be 99% accurate or even 99.9% but you're just, you're never 100% and customers started noticing that everyone's well, they were these sort of unexplained errors where things would go wrong. In these critical areas of their business where they didn't want errors to exist at all. In the sort of conventional wisdom on Zenef, it's shifted from, you know, hey, this is incredible to, well, the concept behind this is amazing. But the execution sort of leaves something to be desired. And once that happened, everything that was working for us top of funnel, stopped working and it stopped working very quickly and it happened just a few months after we had raised this enormous amount of money at this very high value evaluation, having sort of promised investors that the top line revenue of the company was going to grow at these sort of really abnormally high rates. And so, you know, the growth sort of plateaued, you know, the burn was enormous because it's really expensive to be doing things in this way. Our gross margins weren't great because again, it's really expensive to be doing things in this way. And investors were freaking out. This was, you know, our lead investor was in Drieson, Horowitz. It was their single largest investment ever. Really? Oh, I didn't know that. At the time, it was their single largest investment in any company. What year was that? This was in 2015. And so it was in that context that suddenly, you know, these compliance issues came to the fore. And like, look, I mean, the compliance issues were real, but I truly believe that like, look, had the business been working. There's no way that that would have led to, you know, the company we all, all would have sort of locked arms and sort of resolve these issues with regulators. And it would have been, you know, a bad press cycle for a week or two. And then we would have moved on. And that's what I believed, you know, even when I left, that was sort of what what I believe was going to happen. That, you know, we were, look, I was going to leave the company, but we were going to, you know, we're going to sort of resolve this stuff, you know, sort of arm and arm, even after my departure. And then it just it changed overnight. And then that's not what happened. Oh, I was just going to say, I don't get the strategy though. Like the strategy was going to be let's lock arms and just go say, may a copa to the regulatory authorities pay a fine and move on. And this was a completely different strategy. But how is the strategy they picked going to help what were the companies real problems? Like, how does that all wave together? I mean, it didn't. So in retrospect, what happened at the board meeting where I agreed to resign, Lars and Ben laid out, you know, they sort of said, look, we want you, we want you to stay around. We want you to stay on the board. We want you to continue to run product at the company. We want David to step in a CEO and we want to keep David as CEO for six to 12 months. And then we're going to bring you back as CEO. And I had had this sort of bad experience at my previous company where I had kind of stayed around for a while, like after, you know, after I had been sort of demoted. And you know, I sort of told him, look, I'm like, I think clean breaks are the best thing here. So if you guys want me out, I'm out. And, you know, Lars turned to me and said, well, what are you, what are you going to do? You know, what, what's your kind of next step here? And I said, well, I think I'll start another company. And now that was not, that was not a popular answer. And Lars sort of said, look, I, you don't have it in you. I don't think that there's any way you're not going to start another company. And I think that, you know, they were worried about, about me competing with benefits or doing something. There was an enormous over the next, like, year, there were just like enormous efforts from the company to try and get me into an enforceable non-compete agreement. Pretty tough in California. So non-competes are not enforceable in California, except there are some exceptions. And one exception is if they are signed in connection with a stock sale transaction. And so the, the effort was always to arrange some kind of stock transaction that could be paired with a non-compete that then would be enforceable. And there were, I mean, some really extreme efforts here. I mean, like, you know, at one point. So first, I mean, I actually didn't intend to start another company in this space at first. And then what happened is it just, it became clear to me that David, like in my view, David was not trying to make benefits work. He was sort of the company's chief prosecutor in the media. He was, he fired all the wrong people. He promoted all the wrong people. You know, he canceled all the wrong projects. It was, and so what it looked like to me was David's, you know, just like, you know, sinking the company driving into the ground. And I totally understand why it, you know, it seemed like, you know, it was sort of to help with his personal reputation. But it seemed like, man, you know, for whatever reason this thing that I thought benefits was going to be is not going to happen. The company's going to go to zero. That was when I decided like, okay, you know, I'm going to start a new thing and start from zero. And I viewed it as like very much like I was going to continue what we had started at Zanifits. And, you know, I went from having, you know, $600 million in the bank and, you know, 1500 employees in an existing product and, you know, you know, 75 million revenue to having zero, zero and zero and starting over from square one. But I thought like, okay, you know, what we're going to do is we're going to rebuild a lot of this. And we're going to go down the path that we would have gone down had David not come in and sort of like turn the company in a different direction. And that was really to sort of expand from this idea of, you know, employee data, you know, all in one HR systems to employee data as this primitive for business software. Red large that the idea was that for the same reason you kind of wanted to have one place to set up an employee or to onboard them across all your different HR systems across payroll and 401K and, you know, medical insurance and dental insurance and so on and so forth. You actually kind of wanted the same thing across the entire company. You wanted that to work for IT for, you know, getting them set up in email and Slack and Dropbox and Salesforce and GitHub and you wanted it to work for, you wanted to ship out their computer and their laptop and get them set up in all of these other places as well and sort of broadly manage employee data across the business and that was sort of the idea behind Riplin. But at one point, you know, when we were in YC so when Riplin was in Y Combinator shortly before Demo Day, David heard that, you know, through the grapevine that that I had started this company that was, you know, going to compete with benefits and sort of got an inkling of kind of what we were up to. And right away, there was a one of the investors in our series C-Round at Riplin was Insight Partners in New York and Insight delivered a lawsuit to my lawyers. So they didn't file it, but one of the things that lawyers sometimes do is, you know, as part of a negotiation as they will say, look, we have written this lawsuit and we're going to, you know, drop it on your doorstep and we're going to file it, you know, next week, unless you settle with us. And so Insight dropped this lawsuit and the company's lawyers, you know, David's attorneys, called up my lawyers was like, it was like the same day or the next day or something and said, hey, we heard you have this problem with this Insight lawsuit and they said, we can make this go away for you. But we're not going to make the lawsuit go away if Parker is competing with us. And so what we need is we need Parker needs to, you know, give us or sell us in some way a bunch of stock and sign a non-compete that is going to say that for five years, Parker will not start a company that does anything and be to be software because it's now enforceable the non-compete in California because you've sold a part of this stock because there as long as you exchange some stock as part of it, you can make it enforceable. I said, no way. You know, it would have, you know, it was, this was like, literally it was right around demo day for YC with, with Rippling. And so I would have had to sort of give up doing Rippling if I signed it and sort of, you know, I'd like, it was sort of mortgaging my future. So I said, no. And there was a huge fight. There ended up being enormous, you know, personal consequences for me of that. But Insight ended up not filing the lawsuit. So it ended up, you know, at least on the litigation side being a bluff. It just causes my stomach to be a nots hearing the story. It was basically sort of a low grade intimidation tactic to try and force like a signing a non-compete and do a stock sale transaction to make it enforceable. And they said, look, this is a lawsuit that,
you know, again, you personally, I had a decent amount of sort of financial difficulties through this period because I had sold some secondary at benefits, but not so much that like I was going to be able to afford a lot of legal defense. So I had a pre-existing agreement as most executives at companies will have that I was indemnified, you know, by the company for, you know, my for legal defense as a result of, you know, things that came out of my role as the CEO of the business. And so through all of this, Zenefits was, you know, had to pay my legal bills. But what was interesting about the sort of threatened insight litigation is Zenefits said, "No, we don't have to pay your legal bills for that. That's your own personal thing." Like that's not. And so it was sort of engineered to be this thing where, you know, hey, it would actually be, you know, millions of dollars to defend this lawsuit that the company would say, "We're not going to pay it." And so, you know, you know, sort of like you're kind of screwed on that front. So you can't, you can't, like even if you think that you'll win the lawsuit, which my lawyer is always very clear, like there were no grounds for the litigation, you still need to spend millions of dollars defending it, that was sort of money that I didn't really have. Of course. So you were being like threatened financially with this lawsuit. I believe also that Zenefits was using the press to blacken your reputation, correct, for quite some time. For like six months, there were just these ongoing daily or weekly attacks. And there were reporters that reached out to me and said, "Look, I get pitches from the company's PR reps, you know, every week about to write an article about you." And David, like when David took over, he hired this guy, Lanny Davis, who is sort of a crisis PR person, who he represented the Clintons in Whitewater, he's gone on and, you know, represented a bunch, a bunch of sort of, a bunch of other folks. But he's a very, you know, David has this philosophy about sort of, you know, media fights that I think Lanny really sort of exemplifies. And so David, you know, sort of explained this to me as Zenefits when we got into this sort of fight with ADP, one of our competitors. And David's view was like, "Look, when you get into a fight with someone, you've got to attack, attack, attack, attack." And if the other guy rolls over and cries, "Uncle," that means it's working. And you've got to keep attacking, attacking, attacking, attacking. And that was his sort of philosophy on doing this. And so that was what David kind of turned against me, you know, once he took over a CEO. And this continued for about six months. And it stopped, like I'm convinced, it stopped only because of YC. You know, at the time, you know, Sam Altman was running YC. And Sam came to me, you know, Sam was just talking to me about what was going on. And I was sort of telling Sam about, you know, how hard all this was. And I didn't hear anything for a few weeks. And sort of out of the blue, Sam called me and said, "Look, you know, I've spoken with Mark and Dresan and told him that, you know, he's risking his relationship with YC. Or if these attacks continue." And Mark went and spoke with David and told David that David was risking his relationship with a 16 Z if he continued. And there was apparently, you know, a big fight about that and sort of a couple of other people sort of like, you know, told me that they had sort of, you know, seen this or overheard it. And then overnight, it stopped, like overnight. And there was still, you know, there was ongoing bad press. But there wasn't, it was very clear that there wasn't someone driving it. You know, there wasn't someone kind of trying to get, you know, more stories every single week. And that's when it stopped. David works Sam Altman. Yeah. Helping out Parker. Yeah, exactly. Because I can only imagine, and it's like, I wish I had been in closer touch with you at this particular moment because you must have, you must have just been devastated at this point, beaten down and just so demoralized. It, I mean, it was, it was really hard. I was super depressed. You know, I really kind of withdrew from, you know, I sort of spent, you know, sort of six to nine months, just kind of like hiding at home, not really seen many people or talking with, with many folks. And, you know, because it all, it all sort of unraveled so quickly. And, you know, but it really was, I mean, like, I mean, Jessica, you say you didn't do anything, but like, you know, YC was really, they were, you know, like YC really stood by me through all of this. And it was, it was, I think one of the incredible things about, about the program is there was, you know, I was really radioactive for a while. Like people would, you know, when we announced our series A, you know, people got attacked for investing in, like, why would you invest in this like awful person and, you know, you know, supporting me was like sort of a deep sort of moral failing. And, and YC was like, you know, they were the most consistent supporters in, in Jessica, we're, you know, sort of in the first round of seed investors and in the Rippling. So, so I will always be like, deeply grateful for that. Oh, well, I'm just glad now that we can kind of move on to the, the new part of the story and talk about Rippling. What gave you the strength to be like, I'm going to do this again, because I would have quit. So there were two things. One is, one is that I really wanted this product to exist. And it was just, I felt like, the benefits had sort of suddenly collapsed for all these crazy reasons that had nothing to do with the fundamental, you know, success of the approach. You know, and so I remember talking with Persona, who is my co-founder at, at, at Rippling, and Persona asked why do you want to do this thing that's kind of in the same area. And I said, I was like, look, nobody's going to build this if we don't. And there's, there's a hundred billion dollars like lying on the floor right or on the street right there. And like you and I are the only people that can see it. And everyone's just kind of walking by oblivious. And like all we have to do is like go over there and pick it up. Like we know, like if we build this, it's going to work. This is what people want. Persona was a YC founder, right? A different, from a different company. He was a YC founder. He started a company called Like a Little. And then he worked with me at, he was an engineering director at Zenefits and then joined me to start Rippling. I just want to take you back. You're, you're kind of at home hiding, feeling very depressed about all this going on. What kind of got you out of that? Was there an event? Was there a conversation or was it just like time just, you just needed time. And then you sort of emerged and you're like, okay, I'm ready to do something new. I, it took years to sort of snap out of that. I mean, I think it wasn't that I sort of came out of that. It was that once I sort of realized that David was kind of like bearing the company. It wasn't going to work. I thought, you know, look, so one was I wanted this product to exist. But the second piece of it was that I sort of was not good at, you know, there, there, some of the, like David is an incredible polemicist. Like he's really, you know, he's an incredible writer and really good at sort of, you know, sort of framing these kind of like attack narratives. And, you know, you see it with some of some of his political stuff now. And that was like, I've never been like really good at that. And so I sort of thought, I'm not, I can't, I can't win on that, on that front. And the only way for me to sort of, and I wasn't allowed, you know, I wasn't allowed to sort of talk about the things that I'm talking about with you guys or have been talking about with you guys right here. And so I thought the only way for me to sort of talk about this to speak in, in some way to like my former colleagues to, you know, extended, you know, friends and family to the tech community, to the media about these issues is, is to build this specific company and build it into, you know, an enormous, you know, $100 billion outcome. And that if I did that, that would, you know, make a statement and it would force like a reassessment. And that was the thing that got me going. And so it wasn't that I wasn't depressed about all of this. It was that, you know, this, this felt like the only path forward was to do this and to make it, you know, sort of really successful. And that was, you know, look, over, over the last seven years, there are many other sort of, you know, things that I love about Ripley and I love the product. I, I really like the people that I work with and enjoy that an enormous amount. But there was a long period of time where, you know, that was, you know, sort of that was the first thing on my mind every day when I woke up in the morning and the last thing every night when I went to bed. And that was the thing that sort of got me to sort of put one foot in front of the other. Oh, wow. On the subject of Ripley, I know it centralized all employee data for its customers. But can you talk a little bit more about it and what makes it unique? There's one critical insight behind Ripley. And that is that employee data is really widely distributed across an organization and, and importantly, not just inside of HR systems. And because of that, I think the right way to think about employee data is as a primitive for a lot of business software that companies use. There's sort of a,
problem that this situation creates for businesses that we can solve. And there's this related corollary opportunity for RIPLIN. And the problem that it creates is that this sort of fragmented employee data across your organization and across all these different business systems is secretly the cause of a very large percentage of the administrative work required to run a company. And you see this as a company in stark relief whenever you hire someone because you need to set them up in all these different places. And you don't just need to set them up in HR systems. You need to set them up in every business system that your company uses. And one of the great things about RIPLIN that we see is we've had third parties go out and look at businesses that use RIPLIN and businesses that use anything other than RIPLIN. And look at people that the number of people that those businesses have in HR, IT, and finance. And one of the things that they found is that at every stage of growth companies that don't use RIPLIN have about twice the number of people in those G&A roles in HR, IT, and finance as businesses that do use RIPLIN. And it's because of the sort of additional administrative burden that you have if you're using really anything other than RIPLIN. And it gets quite extreme. It like a thousand employees. I think it's something like, you know, 46 people for businesses that don't use RIPLIN versus 28 people for companies that do use RIPLIN. That's amazing. And so there's a real operational RIPLIN makes your company more operationally excellent because you don't have a bunch of people doing things in this, you know, doing a bunch of administrative work that you otherwise would have. The second sort of corollary opportunity comes from the fact that, you know, companies that make business software. And I don't mean companies that make HR business software. I mean, all companies that make business software, they're kind of aware of this dynamic. They sort of know that if they ask you for a lot of information about your employees, it just means a lot of work to implement their software because now you've got to load all that data into their system and you've got to maintain it. You know, anytime you hire someone, anytime something changes, you've got to make changes in their system along with all the others. And so companies that make business software, they tend to ask for little information about your employees as they possibly can. And that's led to this situation where companies, business software just knows much less about your employees than it ought to know. And that has a whole set of product implications. It means that, you know, most business software, you know, is dramatically under permissed because in rippling, you can set up role-based permissions that are inherited based on someone's job or function within the organization. But in most business software, what happens is everyone has no administrative permissions at all by default. And you need to click and make someone an admin one person at a time, which means you don't do it very much. And you end up with this kind of bank teller situation in most business software where there are a very small number of admins and everyone needs to sort of wait in line for those people to kind of help them do their job. Just like the way you used to have to, you know, if you wanted to check your account balance or make it a deposit or a withdrawal, you had a wait in line for like the bank teller to do that for you. A second example of this is most business software is really weak on approvals, things like approvals because they don't understand relationships between people within the organization. They might know who someone's manager is, but they don't know who the VP of their department is or their HR business partner or their strategic finance associate. And often you want to route approvals to people based on those types of relationships as well. And reporting is weak in most business software, because in analytics, because a lot of the way you take transactional data and turn it into insights about your company is you want to look at it by department, by manager, you want to zoom in on a particular work location, you want to filter out your interns, look at only people that have two years of tenure. And so often a lot of the sort of data stacks that people put together, you know, what today we call ETL and data warehouses and BI tools is really about, you know, getting all of this data joined and transformed in a way that you can, you know, combine it with org data to get to sort of insights about the organization. And so the opportunity for Ripley is really like, look, what if, you know, what if you didn't, if you had a different set of assumptions, like if you didn't start from the assumption that you're just not going to have access to this data about employees and about the organization, there's a lot of business software that you would build very differently. And it would be, I think, much better as products. There are a lot of product capabilities that you would have in all of these other areas. If you started with employee and organizational data deeply embedded in the foundation of the product. And is this what you refer to as a compound startup? Yeah. And so that's when I talk about, you know, a compound startup, that's what I mean. It's it's saying, look, we're going to build a whole suite of like deeply integrated and interoperable products that are all built on top of, you know, this foundation of, you know, at the very base layer, this just deep understanding of all of your employee data. We call it the employee graph because it's this sort of graph-based representation of not not just like, you know, employees in their department and their work location, but also data that's coming in from other other parts of the product, or even other third-party products and, you know, information about, you know, their GitHub pull requests and their their opportunities that are in their name and Salesforce. And you know, and that that sort of forms the foundation of that data layer. And then on top of that, a set of what we call middleware components or platform component capabilities that are like shared sort of capabilities across all of our products. So, you know, things like analytics and permissions and workflow automations and approvals and a few other things, that then you take as reusable Lego blocks and you use to then build sort of all as the sort of, you know, underlined structure for a lot of different business software. Yeah. You know, our goal at Ripley has been to launch five new skews every year. And so, you know, we were sort of constantly seeding or nucleating new product organizations to build these new products on top of this sort of larger system. And the advantage is always that these products are, you know, deeply understand your organization in ways that they're competing standalone products don't. We tend to invest really deeply on these sort of fundamental components of business software, you know, analytics and permissions and approvals and workflows and things like that. And so, they tend to win on those things because competitors will kind of build those things as sort of afterthoughts. But because we're building them across all these products, we can invest much more deeply. And everything's all in one system with one UX and sort of, you know, sort of much easier to use for that reason as well. Well, I'm glad you brought up competitors because going back, that was one of the driving concerns at Zenefits, right? You were talking about how, you know, you guys really wanted to make sure you were the ones and that you banished all competitors along the way. Different mindset, probably for Rippling or maybe not, like you tell me, what, how do you think about competitors now? Yeah, I mean, so Rippling competes with a ton of different companies. I think the mistake that we really made at Zenefits is I think, you know, we did this thing, you know, we to sort of grab market share very early on, which was not scalable. And I think that was okay for, you know, at first. I mean, why is he's monstrous? Like one of why is he's sort of pieces of advice is do things that don't scale? And I think that's absolutely right early on. But the sort of counterpoint to it is like, eventually you need to scale them. And we really didn't. And that was the problem. And so the issue, I think the sort of the real sort of mistake at Zenefits was doing all of this manually. And and we should have, you know, maybe we should have done that during YC, but then we should have really focused on automating that before we started growing again. And that was the thing we did that very differently at Ripley. And so at Ripley, it took us a long time to launch. I mean, we had, you know, for for two years, the company was like 50 engineers and me and a few other people, but mostly engineering. And we sort of built this thing end to end, but all in software, you know, there were no operations of any kind inside the company for a long time. And actually until we were at like 5 million in ARR, we didn't have anyone in support in the company. And so, you know, I did a lot of the customer support. The engineering team did a lot of customer support for their specific products. And it was only, you know, once, once, you know, we got to some really large scale that we started bringing in a support team, but it sort of forced us to kind of just drive down all of the operations work inside the business. When did you get an HR team? We hired our HR team reasonably late inside. I mean, when I was when I'm talking about operations, I meant more like customer operations. So it's like, you know, things to get people enrolled in insurance and, you know, man, and so, right. And so we were trying to make sure that everything ran on software rather than people for customers. But actually, one of the things that that's still true about Ripley is that I'm the only full admin for Ripley in Ripley. This is going to be my question. I wanted to confirm if you are the HR administrator for Ripley. Well, that's where I was going with my question too. So, so to be clear, we also have a great HR team that does, you know, you know, helps with other types of things. And obviously, if
it's very important from things like compliance and making sure that things don't go off the rails that you have like really good, strong in-house HR. So we have a great HR team, but in terms of like a lot of the administrative work around HR, that's something that I handle personally. So I run payroll for rippling as 2,000 employees across a dozen countries. And I run payroll for everyone. I manage employee benefits, manage a lot of sort of IT, app provisioning rules, things like that. I approve every expense above $10 in the company 'cause we have a met expense management software. And so that's amazing. A lot of why I think the product works so well for customers and why you see that customers are able to have so many fewer people in these functions is because we spend a lot of time working to sort of make it possible for me to keep doing that. And that forces you to kind of constantly automate more and drive down the level of administrative work. And that then sort of, you know, there are benefits that accrue to all of our customers from those investments. - And for any founders out there who are listening, I need to point out that like we get really excited when we hear of founders who are eating their own dog food. - It's a huge advantage because look, I promise you, look, we have payroll competitors that don't use their own system for payroll. SMV payroll systems that run on workday, 'cause they can't use their own system. And I know the CEOs of ADP and PayLocity and PayCom and UKG, and they're not, they don't run payroll for their companies. And so I think that doing that, it gives me a right, I think it gives me a right to an opinion about the product. You know, it like a lot of, you know, like I can, one of I think the great pieces of advice that YC always has for founders is to talk to customers. And that's great advice, but another way to kind of do that is to really be the customer yourself. And then you can have, you know, those conversations in your own head and they're often like much higher fidelity and can happen much more quickly. - Your own user, I love it. Can I go back quickly to this sort of kind of modular structure where you, you know, where you try to launch the new products and stuff? I've also heard that you hire a huge number of founders to sort of run those business units. Is that on purpose that you've done this or is it just worked out that way? - What Ripley is doing by, when we're building all these different products in parallel, it's very much counter to the conventional wisdom on how you're supposed to do this. Because the way you're supposed to do this is to focus on one extremely narrow thing and go deep on that. And I happen to think that that advice is wrong or at least limiting. And that I think that the way that we've built business software over the last 20 years is mostly incorrect. And it's been to build a lot of these sort of narrow point solution products that inhabit these sort of local minima from a client perspective. But actually like the global minima is to take this compound approach and have one system that kind of does a whole bunch of things for companies that the way we build software today, and this is not my idea, I'm stealing this from someone else, but it's kind of like if you bought a car and instead of buying a car, you bought a steering wheel from one company and a chassis from another and a carburetor from a third. And you sort of brought it home and sort of tied it all together with Scotch tape and glue. And then of course when you're driving down the road, you'd have parts falling off and wouldn't work very well. The right way to do this or the sort of global minima, the ultimate product for customers is to do all in one and not just all in one, but all in one is in one. And so that's the approach at Ripley. One of the things, so we knew when we were starting Ripley that this was unconventional. And so we were always, we thought, like look, this compound approach was both something that could become like our biggest enduring advantage, but was also like, if the company doesn't work, why will it not work? And it was like because it's like really hard to do this and there are a bunch of reasons why this is not supposed to work. And so a lot of our focus at the company has actually been on making this particular approach to building software work and finding all of the different places where it breaks down and then finding solutions for each of those things. And there are a bunch of places where it breaks down or places where we've had to find sort of like really clever solutions, but one of them, one of the things that you absolutely need is you need to be able to sort of create these small teams that are individually very focused and sort of can sort of run quickly to sort of build products within Ripley. And the best profile of person for doing that are people that have had this experience of starting a company. And so we hire a lot of former founders. I think the last time we looked at this, it was like a year or two ago. And I think we had something like 50 people that had started companies at Ripley. Including-- - Wow. - Yeah, including a whole bunch of former YC founders that work at Ripley and in a variety of different roles, but many of them have started in our leading individual products and sort of business lines within Ripley. - I love that. That makes me so happy. - Yeah, it's great. - Speaking of which, you know how you were saying you have this sort of underlying system that has all the employee data and sort of seamlessly just works amongst all these different business units because that underlying operating system or technology, if you will, is so robust. Will that make it easier to sort of introduce AI into different things if you wanna do that? Are there any plans for that? - My take on AI is-- I mean, first I'm like, I'm really skeptical of companies that sort of issue press releases announcing that they're now an AI company. So like one of the things that one of my goals is to like never do that. And I also think that like-- - That's funny. - I think that like when people incorporate chat GPT into their products, I think they're actually incorporating the wrong part of it. They're sort of copying the chat interface and I think the chat interface is a bug and not a feature. And that nobody actually wants to chat with their payroll software or their expense management software. And that, but there are a bunch of ways that you can incorporate or that you should incorporate sort of some of the ability to work with unstructured data and the capabilities that that brings into your product. And so like I guess like my sort of thesis about rippling an AI and we're sort of very early in kind of doing this, is that a lot of the B2B AI use cases will end up requiring like a deep understanding of your organization and your company. You know like almost any time that you want to sort of do something AI related with employees. And again, that's not just an HR software. It might, you know, could be in any sort of vertical you know B2B software vertical. It kind of matters like you need to understand is this person, is this person a junior IC employee or are they the VP of a department? Are they an engineering or in customer support? You know, are they in San Francisco or in Bangalore? Are they an intern, a contractor, a W2 employee? What teams are they on? You know, what sort of all of that context about their job and role and function and their relationships to other employees within the organization is a really important input. For almost anything that you might want to do from an AI perspective in a B2B software context. And so that, when we think about AI, it's always about sort of what are the types of applications that require this sort of deep contextual understanding of your company and that sort of the, those are sort of the areas that I expect that we'll focus on. Okay, we won't hold you to anything specific. How was why a combinator different? How was your experience different between the winter 2013 session and 2017 that you went through it twice? Yeah, so the, I mean, the first time I did why a combinator, I mean, it was the three most productive months of my life. It was an incredibly, incredibly intense experience. And I think it was intense both because the YC program is like designed to do that. It's very effective at doing that. I think the real value of the program, which I only came to understand once I was doing it, is that YC is just great at sort of creating a whole bunch of urgency inside of your company right from day one. And the challenging thing, one of the challenging things I've always found about starting a company is like, it feels superficially like being unemployed. You know, like you're kind of sitting around on your couch, you know, screwing around on the internet. And like if you don't get anything done on any,
particular day, like nothing happens. Like nobody gets mad at you, you don't have customers that are yelling at you. And so it's really hard to get in this groove of just moving quickly. But that's like absolutely critical for making the company successful. And I think why I see with like, you know, having this cadence of dinners where, you know, it's sort of once a week, but not not five days a week, you know, you know, it's, it's like just precisely tuned to sort of create a lot of urgency and you sort of look around, feels like everyone else is accomplishing something. It creates a lot of pressure for you to do the same. That is what has always been so powerful about YC for me. And that was very true for us the first time around. There were a few things I think made it really different the first time around. So one was, I just remember PG's like opening talk to the batch and it was really incredible. And I had, you know, I had come off of this sort of seven years of working at another company where things were not working. And PG at one point sort of said, look, there are, I mean, there were many, many, really great lines in this talk. And I don't, I don't remember all of them, but I remember he sort of said, look, there are two or three of you in this room that have what it takes to be really successful founders. And, you know, the rest of you probably don't like that's okay. Like there are other things that you can do. But I, you know, I remember thinking like, oh my gosh, I hope it's me. And then one of the other things that was that really sort of dialed it up a notch for us is that there were, there was another company in our batch that was doing the same thing that we were doing, called simply insured. And they started in a slightly different area and then pivoted and we were kind of doing, oh yeah, I think they pivoted into it. And I remember, so for us, it was just the level of urgency was just extra high because we would see them like talking to someone at dinner and it was like, they're talking to our customers. And and the reality is is every company like your competitors are out there. But you often like, you don't have to confront that in quite as viscerally away as we did in, in, in Y Combinator and that sort of first go round. The third thing as I remember having office hours with, with PG. And I joined, so I joined Y Combinator as a solo founder and then Lux, my co founder is, and if it's joined a few weeks later. And you know, I had built like the barest outlines of a prototype. I mean, there was not, I mean, we were so far from having like a real working product. And I remember meeting with PG early on and saying, look, you know, and obviously, YC has said you got to launch early, you got to, you know, get start selling to customers, you got to do all this before demo day. And so I said, okay, I'm going to have to sell it. And we think if we really push, we can get a product live, you know, by like March 15th. And that'll give us two weeks to sell before demo day. And PG, looks at us and said, you can't do that. You got to launch, you got to launch by the first week of February, no matter what. That's just not enough time. You know, I said, well, there's just no way. Just know, you know, it's already like, you know, the second week of January, like we can't build this thing in three weeks. It's not possible. And you kind of looked at us and said, well, you know, I don't know what to tell you. Like you might as well, you might as well give up and like go home because like your company's not going to work if you can't get this live by the first week of February. And I was like, oh my gosh, like I already failed. You know, like what? What are we going to? And so, and so Lux and I we we focused on this and we figured out we figured out this way and like, you know, and we just really pushed ourselves and figured out a way. And we ended up launching like, you know, not the first week of February, but the second week of February. And it actually made a really big difference because we launched and tech crunch wrote an article about us that said, you know, hey, a company doing this interesting thing, like doing insurance online and, you know, all the sort of interesting stuff and a video stuff. And then simply ensure launched like two weeks later. And they there was an article about them that was like, weird, there's this company like copying Zenefits, you know, like, why where did they come from? And so it actually made a really big difference to to the company and was absolutely the right advice. And I think like the second time around, like, why she was still a great program, you know, it was not as intense for me personally. And I think in part because I had done it before. And so I was doing it. I wanted to recapture that same intensity. Like that was why I did it the second time around. I thought it was really important to go back and, you know, be right, right back at square one. But it was not it was not like totally the same. I think in part because I had done it before. In part because there was no simply insured in the batch quite frankly. And so it was not. And then also because, you know, I think PG, PG as much as like, you know, the the partners there are great. It was not it was not the same without without you guys there without PG there. And so I actually tell them that I remember there was there was this like moment in office hours or in the in the sort of, you know, small batch meetings where there was a company that was building a sort of assistant, like an AI assistant built into sort of Android. And one of the partners sort of asked them, how long do you think it'll take for you guys to get something live that will be, you know, really useful for just one person. And the, you know, the founders sort of thought about it. And they said, I think if we really push, we can get something live that's useful for one person by demo day. And I thought like, you know, like, they're going to get it. Like, I could just wait to see what happened. But then the partner sort of said, like, okay, that's great. And then sort of moved on. I was like, Oh, like it's it's a little bit different. I mean, I look, I get that there's a balance between, you know, sort of how how much sort of urgency and anxiety like people can absorb about this stuff. You know, and there's probably a balance there. But I thought I remember thinking like, huh, it's not like totally the same as it was before. Also maybe different because group dynamic versus one on one. I mean, it sounds like when PG was cracking the whip on you, it was just you and he and your co-founder probably. Yeah, that's hard. Group office our dynamic. I think maybe you. Yeah, yeah. It's a little bit of a gentler. It was definitely it felt a little a little kinder and gentler, which is, you know, they're both they're both good things about that. And and something, you know, maybe something that you miss. Hang on now, though. Now we're getting, I've just realized something. So you're going through why I see the second time demo day. Did you raise money after demo day or was it sort of before or what was the timing of when you raised the money and wasn't there some attempt to um, Kibosh the round. So we end up we raised a pretty decent seed round earlier on in the program and there were a couple of reasons why we did that. But among them, quite frankly, is like one of the big ones was just there was so much like while I was going through YC with Ripley. There was a lot that was still happening with benefits. Okay. And so one of quite frankly, we wanted to just show that like there were still, you know, investors that supported me. And so one of our investors told me said there's there's one reason to invest in Ripley. And there's one reason not to invest in Ripley. And they're both the same reason. The reason reason being my my involvement with the company. And and so there were always there were always a lot of investors that came out on on sort of you know, there were people that came out on both sides of that that dynamic. But they're always enough that you know, believed in believed in me and believed in the business that that they invested that we were always like, you know, did great. But when we did our series A, you know, there were, I mean, we ended up with a ton of term sheets and the moon from Klinger Perkins ended up leading the round. But it was a controversial round. And there were a bunch of investors that that backed out. I had a general partner meeting scheduled with benchmark. And, you know, the GP that I was working with there called me up on a Sunday night and said, you know, I'm sorry, but you know, so the Jeep general partner meeting you get, but for the blisters, you might not know what that is. It's sort of the penultimate step in a fundraising process where you meet with the full partnership. And if it goes well, you might get a term sheet after that. And so we had a, and they usually happen on Mondays. And so on Sunday night, the benchmark GP called me up and said, look, I'm sorry, but Bill Gurley is poker buddies with with David Sacks and just, you know, had a conversation with him. And so we have to cancel the GP meeting. And, you know, same thing happened, something similar happened with Graylock. And, you know, even Mammune at K.P. had a run in with David, you know, after after we signed a term sheet, you know, David sort of found out about it. Got, you know, really upset and had sort of a very, you know, sort of a huge confrontation with him about it. So there was, there was this sort of behind the scenes effort to kind of derail the fundraising. And then I think after after the series A, that sort of mostly went away. It sort of stopped from there. Wow. What a story. I'm glad Mammune stood his ground and got the series A done. Okay. So after all of that, when you measure results by what software has been created, do you think that the world is net ahead with Rippling? Yeah. I mean, well, so first, I mean, I think it's important to say, like, look, we're not, we're not curing cancer at Rippling. And so, yeah, I don't, I don't want to sort of, like, I think, you know, it's a mistake to look, you know, sort of,
be two sort of like, oh my god, every tech company's changing the world in some way. But I think we have a lot of customers that are doing that. I think look and-er-o's one of our biggest clients. I think they're doing great things for the United States and for the conflict with between Ukraine and Russia and that's a really important company. And I, you know, look, we're very small, you know, sort of part of everything that they're doing. But, you know, to the extent that there are a lot of companies out there that can focus on, you know, focus a little bit more on, you know, their own products and what they do. And, you know, if we can make that a little bit easier and a little more efficient, I think that's really cool. Good. You the world is net ahead. That's how I phrase the question. Not are you doing something as important as carrying cancer, but is the world net ahead? Yes, it's a net ahead. Yeah. It was a leading question, I think. I think that's fair. Yeah, that's a softball. We, well, Carolyn, let me ask you, do you have questions? Because your mind must be racing since you are a lawyer. I have a ton of questions, but actually, I want to ask them completely unrelated to anything legal. So you are Parker, literally, the textbook example of formability for YC. And when I say literally, I mean, like, we used to record interviews. I don't know if anyone at YC's ever told you this, but we actually rewatched your video a whole bunch of times because we're like, this guy's so formidable. Like, can we find clues? And the way he answers questions that tip us off that, like, he's so formidable. Anyway, I don't, that was a long time ago. So I don't actually remember any of the specific takeaways, but I guess I'd ask you, when you think about yourself, even like as a kid, as a teenager, whatever, were you always like this? Like, what makes you so formidable? Like, in other words, character circumstance, combination of both, what do you think? That's interesting. I mean, so I think I've had a lot of like really big ups and downs in my life. And there are a lot of things that have been great for me. I mean, like, I had wonderful parents, have wonderful parents. You know, but like I was, you know, they're fairly well off. And my dad is a corporate lawyer in New York. And a lot of people have a lot of hardship, you know, in that area that I've never had. But, you know, I also, you know, I had a really hard time in middle school was just, you know, sort of bad situation, like really sort of bullied and picked on. And that I think has ended up being kind of like really defining for, you know, me like psychologically. But then also, you know, I, you know, in college, I spent, spent all my time working on the newspaper, which was a lot of fun. For me, I think I ended up being kind of like running a startup. You know, you're sort of running this, this organist. The Harvard Crimson, right? The Harvard Crimson, yeah. Yeah. I was managing at the Harvard Crimson. But I spent so much time doing that that I, I failed out of school and had to take you off. And that was, that was just like really hard. And, you know, and then just like, by the way, YC's co-founder, Robert Morris, not alone. A lot of great people had failed out. You know, and had to take you off. Yeah. That's why I was laughing. I'm sorry to laugh for your pain. I was just like, oh, that's, I mean, it's a really nice story. In tech, you know, there are a lot of people, it's sort of like, oh, I am badge of honor, like tech, you know, college dropout. But it didn't, it didn't feel that way to me. It felt like just like a deep and miserable failure at the time. Very humanity and embarrassing. You know, then, then same thing with my first company, you know, I ended up, look, I mean, it was a hard slow grind. It was, you know, seven years of just ongoing failure. And I think when that happens, different people react in different ways. But I think for for my co-founder and I was kind of like, you know, I sort of, I haven't experienced this, so I don't know, but I sort of think of it as kind of like what it would be like to be, you know, in a marriage and, you know, a child dies. That it, you know, just the other person constantly reminds you of everything that's going wrong. And it led to a lot of, you know, interpersonal conflict and you really ended, I think, like the friendship that I had with him. But also resulted ultimately in in me being sort of fired from the company. And similar, similar type of thing, like I thought when I left, I thought I would never be able to do something like I thought my first company was going to go on to incredible success. And I was not going to be a part of it. It was this incredibly depressing thing. And so I think, you know, there just been like a lot of, a lot of sort of really big ups and really big downs. I don't like, sometimes people would say like, you know, you learn so much from your failures. And I don't think I've learned a lot from failure except for, you know, how much it sucks and how much you really want to avoid it. And so I wouldn't advise it for anyone. I think it's like, you know, very, very destructive. But I, you know, I do think that, you know, like, I don't know if I would describe, I mean, I'm like flattered that YC thinks that I'm formidable. But I'm like, I think that like to, to accept that there's like, like a certain kind of tenacity, you know, maybe that I think that's probably where it comes from. We are such fans of yours. Well, thank you. And we're so proud of you. I mean, you're doing so well. And you're just, there's so many things that aspiring founders could learn from you. We're so glad, you know, you're part of the YC community. And I know you recently came back to talk to one of the first back in person dinners that they've done at YC and that it was off the charts. That's pretty awesome. That's amazing. John Levy, you know, aka J. Levy, Carolyn's husband was just raving about it, saying it was one of the best talks he ever heard. So thank you for being an important part of our community. Sure. Thank you for opening up today. I mean, I think it was a really fascinating conversation. Well, thank you very much. And congratulations. Thank you. We'll talk to you soon. Thanks for coming, Parker. Bye. Bye. What a story here. Wow. That was amazing. I know. I mean, I think we just need to kind of basically leave it at that. Let the story speak for a while. Because I don't think there's we can add anything. It is a dramatic story. I mean, I will say between us, we've seen a lot of dramatic stories in Silicon Valley. Some that people know about. Some that people don't. No, that's a good point. And that definitely classifies as, you know, very bad investor behavior and very sort of horrible things happen. Yeah. Kind of one for the record books in terms of crazy behavior. Exactly. But I will say because I don't want, I don't want would be founders to get scared away. Don't you agree that that was sort of an exceptional story and that it's oh my gosh. Of course, that's why I'm saying one for the record books. Like that is a wild story. And yeah, like there's a, I mean, that's just very unusual. That's not really what investors do. So. Yeah. So we'll just, we'll just leave it there. I'm very much looking forward to it coming out. Really appreciated Parker's. Yeah. I mean, telling that story couldn't have been easy. And you know, I feel like he took ownership of the things that he got wrong because he did get a few things wrong. He definitely didn't get wrong in those things that he was accused of getting wrong publicly. You know, but he did get a few things wrong and he took ownership of it and I appreciate it. Appreciate it that and I'm glad he was comfortable sharing it with us. So I think I think it's going to be a good episode. I think so too. All right. I'll see you next time, Carolyn. Bye. Bye.
Podcast Summary
Key Points:
Parker Conrad was ousted from Zenefits in 2016 amid media attacks claiming compliance issues, a cheating scandal, and a party culture, which he argues were misrepresented.
The compliance issue involved insurance licensing; Parker believed based on legal advice that representatives didn't need licenses in all states, but later fixed it to over 95% compliance.
The "macro" was a script he wrote to stay logged into a licensing course, not to cheat, as he knew the material and scored 94% on the exam.
The party culture accusation stemmed from a found condom in a shared building, which was blown out of proportion by the media.
Parker believes his ousting was a pretext by investors, led by David Sacks, to scapegoat him for Zenefits' real business problems, like declining growth and poor gross margins.
He was legally restricted from defending himself, as the company controlled attorney-client privilege and paid his legal bills.
Summary:
Parker Conrad, founder of Zenefits and Rippling, recounts his dramatic ousting from Zenefits in 2016, which he attributes to three exaggerated media narratives. The first involved insurance licensing: his lawyers advised that representatives didn't need licenses in all states, a mistake later fixed to over 95% compliance. The second was a "macro" script he wrote to avoid manually clicking a button for 18 hours during an online licensing course; he argues it wasn't cheating since he scored 94% on the exam.
The third was an alleged party culture, sparked by a used condom found in a shared building, which the media sensationalized. Parker claims these were pretexts for his removal by investors, particularly David Sacks, who issued a different press release blaming Parker for compliance issues. In reality, Zenefits faced genuine business challenges like declining growth and negative gross margins.
Parker was legally gagged from defending himself because the company controlled attorney-client privilege and legal fees. He believes Sacks scapegoated him to avoid personal blame, as most compliance failures occurred under Sacks' own management. Despite the turmoil, Parker went on to found Rippling, another successful unicorn.
FAQs
Zenefits employees were properly licensed in their home states but not in other states, based on legal advice that it wasn't required. The company later fixed this by getting everyone licensed everywhere, but it became a major media controversy.
Parker Conrad wrote a simple script to keep his online insurance licensing course session active by automatically clicking a 'still here' button, avoiding the need to manually click every five minutes for 18 hours. He passed the exam with a high score, but it was later portrayed as cheating in the media.
No, Parker Conrad says it was mostly false. Employees often worked late and had beers on Fridays at 8 PM, but the 'sex in the stairwells' story came from a landlord's email about a used condom, which could have been from anyone in the 30-company building.
He thinks the board used media-blown controversies as a pretext to oust him, masking real business problems like evaporating growth, missing plans, and poor gross margins. A planned mutual press release was replaced with one blaming him for compliance issues.
He decided to aggressively capture market demand by taking on all administrative work for clients, fearing fast followers. This led to rapid growth but also burnout culture and financial challenges.
David Sacks implied the compliance issues were on the sales team reporting to Parker, but 70% of violations were in the account management team reporting to Sacks. Parker was legally restricted from revealing this due to attorney-client privilege owned by Zenefits.
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