20VC: Is Speed the Most Important Thing from 0-1 | Why Hiring Inexperienced People is Better | The Biggest Lessons Scaling Zip to $1.5BN Valuation with Rujul Zaparde, Co-Founder and CEO @ Zip

24 Apr 2024 · 56 min

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In short

Podcast Summary: The Twenty Minute VC (20VC) - Episode with Rujul Zaparde, Co-Founder and CEO @ Zip

Episode Overview

  • Host: Harry Stebbings
  • Guest: Rujul Zaparde, Co-Founder and CEO of Zip
  • Main Topics:
  • Transitioning from Airbnb to Zip
  • Strategies for scaling a startup
  • Importance of speed in startups
  • Hiring practices and insights on team management

Key Highlights

  1. Rujul's Journey from Airbnb to Zip
  2. Rujul discusses the lessons learned from his failed first company and his experiences at Airbnb.
  3. The "aha" moment for co-founding Zip was rooted in personal experiences with inefficient procurement processes at Airbnb.
  1. Competing in a Crowded Market
  2. Rujul chose to enter a competitive market, believing that a crowded space indicates significant pain points to address.
  3. He emphasizes the need for startups to have a unique insight into the problems they are solving.
  1. Importance of Speed in Startups
  2. Rujul argues that speed is crucial for success, likening the progress of startups to a race where those who learn and iterate quickly will outpace competitors.
  3. He believes that being agile and willing to pivot is more beneficial than slow, methodical planning.
  1. Hiring Practices
  2. Rujul advocates for hiring less experienced candidates who demonstrate potential over seasoned professionals, as they often bring fresh perspectives and original ideas.
  3. He reflects on the mistakes of hiring too quickly for scale before truly understanding product-market fit.
  1. Scaling Zip to a $1.5BN Valuation
  2. Rujul outlines the key moments that led to Zip’s growth, including the importance of repeatability in sales processes.
  3. He emphasizes the need for founders to focus on the core pain point they are addressing rather than accommodating a wide range of customer requests.
  1. Managing Teams and Culture
  2. Rujul shares insights on the challenges of building and managing a sales team, especially coming from a product-led background.
  3. He stresses the importance of creating a culture that rewards speed and fosters original thinking.
  1. Long-Term Vision
  2. Rujul aims for Zip to be a generational company, focusing on solving procurement inefficiencies through technology.
  3. He envisages a future where approvals are automated, reducing the need for human intervention in approval processes.

Key Takeaways

  • Adapting Quickly: Prioritize speed and adaptability over perfection in early-stage startups.
  • Hiring for Potential: Look for candidates who may lack experience but show potential to innovate.
  • Focus on Core Problems: Identify and focus on the specific pain points that your product addresses rather than trying to cater to varying requests from multiple customers.
  • Importance of Culture: Build a company culture that encourages fast execution and values original ideas.
  • Long-Term Goals: Aim to create a sustainable business model that addresses real pain points in the market.

Conclusion The episode provides valuable insights into the entrepreneurial journey of Rujul Zaparde, emphasizing the significance of speed, innovative hiring practices, and a clear focus on core problems in the startup ecosystem. Through his experiences, Rujul illustrates how adaptability and a strong company culture can drive enduring success.

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Transcript

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0:00I would much rather invest in the person that has potential, that maybe hasn't done the job before. I mean, they don't have the experience, they're going to first principle the problem. So they're just generally more likely to have more original ideas. Speed is actually really, really an advantage. You're not going to be right, so you might as well just learn quickly and move on. Welcome back to 20VC with me, Harry Stubbins. Now, Zip. Zip is one of the fastest growing companies in B2B. They are the world's leading intake to pay solution, and they raised $100 million in a series Sea Round from some of the best in the business in 2023, valuing the company at $1 .5 billion.

0:34Today we have their co -found and CEO, Rijul Zepardy, joining us to discuss scaling sales for the first time as a product led founder, how to do it the mistakes often made and his biggest lessons from doing so. Before founding Zip, Rijul was a visiting partner at Y Combinator and before that was a product manager at Airbnb. But before we dive in, and Cooley, the global law firm built around startups and venture capital. Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 60 plus years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund's lifetime.

1:15We use them at 20 VCs and have loved working with their teams in the US, London and Asia over the last few years. So to learn more about the number one most active law firm representing VC backed companies going public, head over to Cooley .com and also Cooleygo .com, Cooley's award -winning free legal resource for entrepreneurs, and speaking of providing incredible value to your customers. Travel in the expense are never associated with cost savings, but now you can reduce costs up to 30 % and actually reward your employees. How? Well, the van rewards your employees with personal travel credit every time they save their company money when booking business travel under company policy.

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3:11You have now arrived at your destination. Rachel, listen, I heard so many good things from Anacone, from Ali Raul Ghani. Thank you so much for joining me today. No, thank you so much for having me. Now I would love to start. I always think great entrepreneurs are shaped early in their career. If we think about people who saw you early in yours, how would your parents, how would your teachers have described the young Rachel? Yeah, you know, that's a tough question. What I do, I, what so when I do remember is that I was always, even like, certainly high but even in middle school, like, as always with my friends, like we're always doing some like business thing.

3:50And, you know, we're always doing something like that on the site, like I remember at one point, we like figured out how to make some really terrible, really, really terrible video games. I'm not even sure what we were using back then. This is in, you know, there are at least 1 ,000s. And then we would like sell them to other people in different schools. And like, I remember we'd even started something that was like, you know, when you're driving around, sometimes you've seen those bumper stickers that say like, hey am I driving poorly? Like you could report me at this at this number. Most of them are for commercial vehicles and we had started something like that for teen drivers.

4:23We certainly couldn't drive at that time. And so we sold some bumper stickers. You know, so it was like that was the type of thing that we were working on. It was always something or the other. Do you agree that you should always be embarrassed by your V1? Do you agree what you actually think that no, you do need to put out good product today given product quality. You'll learn so much more with number one, like just put something out there because chances are what you're building, it's probably not right. It's probably not right. You just don't know what's not right about it and you won't know until you like put it out there.

4:55And one, you know, one thing I think you can always do is like if you lack something, you can always make up for it in service. You can ask better questions, you can learn, you can iterate faster. And people really appreciate that. I totally agree and you can build such customer advocates in the early days by actually just being and so responsive and so intuitive to their feedback. Tell me dude, how are we gonna get onto learnings from past, but just in terms of zip, why did you choose this? What was the aha moment for you when it came to founding zip? So it was a problem that my co -founder, Lou and I, that we had both experienced, so we had, you know, we actually met, we both worked together at Airbnb.

5:28Lou was an engineering leader at Airbnb, I worked as a product manager. You know, what happened was that I remember actually one day, We woke up to an email message saying, hey, Rajul and Lough, you know, someone so has left the organization. You guys have been designated as a business owners of our contract with this large contract, software contract. And you know, there's a renewal coming up. And we were assigned somebody from the procurement organization because it was such a large contract. And we said, sure, we'll be the business owners. Like, tell us what we need to do. And the first thing we heard we had to look what we have to do was we were told, hey, you have to go to our ERP system, create a PR.

6:10We both looked at each other and we were like, sorry, what? And the person was like, oh, it's a purchase requisition. You know, at the time, the only PR that we knew was a pull request. And so we were like, oh, well, purchase requisition. Okay, I mean, I can understand what that means. And so of course, I remember we go to the ERP and the first question is, select your cost center. And there's thousands and thousands of options in there and no one has ever asked us or told us what cost center we're in like we have no idea What to select and so we pick something and then of course later on and ask what's the what's the GL code?

6:42And we're like we don't even what is a GL code at you know at the time and of course it's an accounting classification Is what it is right but we have no idea thousands of options select something it's submit I remember we distinctly went back to the procurement person who were assigned to say hey we're done thumbs up, like just let us know when it's approved. And he said, no, no, no, no, no, you're not going anywhere. That's just the PR. You know, once you get the contract, it's got to get uploaded over in this system because that's where the legal team reviews contracts. And also it's a software renewal.

7:13So you have to go raise it, you know, an IT ticket over here because the IT team needs to review. And also we're sharing all this customer data. So now you've got to raise a security request over here. You've got to raise a privacy request over there. And so we actually do five or six different intakes if you will of this information And then of course of course as you would expect you know in a month or two months It's very hard to understand exactly exactly what's happening with this request and is it blocked and if so where And I remember anytime I would have to ask The gentleman we were working with in procurement the poor guy would have to like he would be like, hey, you know I'm really sorry.

7:48I really don't know. I'll get back to you tomorrow because what he was doing is just pinging all these people manually. And so we felt like there had to be a better way. The thing you learn about the shows is we have schedules and then I just go for it. So one of my biggest things that I look for when investing stay is that massive markets, obvious, but with very low competition. A strange one that other people don't necessarily have. When you look at this market as a newbie, you're like, gosh, you just type in procurement or spam management and it's like, add, add, add with big names. When you look to it, you're not like, a lot of players, this is not attractive because it's so competitive.

8:25In a sense, absolutely, but there's a pro in a con. The pro is that, well, if there's a lot of parties in the space in general, that means it's a big space and there must be some real pain here. And so for us, it was like, huh, there's enough here. We're not taking on like market risk. But what's the unique insight we have based on the problem? Is it a product marketing challenge? So again, when I'm investing, I'm like, okay, competitive market, but aren't you the RUJUL and LUHAVY unique insight. Then it comes to, well, how the fuck do we stand out in such a crowded market? How do you think about a product marketing challenge when buzzwords are kind of the same and you need to stand out?

9:01It's a great point. It's an education problem. It's challenging and you have to select in people in and out. Like most people won't get it. And that's okay because if they all got it, somebody would have started your company already. You have to like filter out, oh, I think this person's just not, they're not there yet, they're latered out, or whatever. It's okay. One day they'll buy, but not today. It's a big problem to go off. I'm just so interested. There's a big problem to go after like first off from day one How do you think about the product decision of whether to go in with a feature that solves one specific pain point or a much broader platform play which really tries to address a lot of the problems from day one?

9:36How do you think about that? You'll eventually get to the ladder, but I think first off like and be given how much capacity you have which is basically nothing when you're starting out you have to find and it's actually it's actually healthy that you don't have that many resources because it's the forcing function to say What is that one thing the one thing point that somebody will be like you're right? I need that thing. It doesn't exist otherwise in the world for me that because what what actually happens is When you have a platform other people have platforms too and they all do everything But then the question becomes how do you differentiate your platform from somebody else's platform and you'll actually always come back to that one thing that you started with, which is, hey, no, no, no, this is the thing that makes us special on the world.

10:16No one else does this anywhere near the level that we do. That's why our platform is better. Sure, we do a lot of things that they do, too, but this thing is different, and it's your wedge. It'll always be. With the first wedge that you had, that first pain point that you identified, did it immediately sell? Was there immediate market pull and you were like, okay, we have early product market fit with first pain point? It was relatively quick, but it took us maybe six, seven months to convince ourselves and be able to better explain what we're doing to our prospects. So to your point about product marketing, you have to start with the positioning and the messaging.

10:53And that probably took us six months. Once we started to figure out how to explain what we're doing and clearly differentiate it, it's certainly exorbit. How did you learn to explain it? For founders listening today who don't feel like it's resonating, who don't feel like it hits. What lessons do you have from that six month period of exploration to your ultimate it started to hit that you'd share with them? Yeah, yeah, no, it's a great question. So what we actually did, so we were actually quite wrote in our approach here every week. Actually, initially it was every day because we had so many calls and then we were like, we don't need to review this every day, we did it every Sunday.

11:29We would write out our quote -unquote investor pitch, which is like a couple sentences of like like what Zip does, but the investor view of it. Yeah, they've talked about like, we marketed that kind of thing. And then the customer, bitch. At one point, we were looking at both of those in one Google doc every single day. And we'd be like, what did we learn today? Would we change how we frame it? And then we would test it for all the calls that we would do the following day. Then it got to find where like, no, we don't need to change it that much. Let's review this every week. And so we basically had this process where we were constantly reviewing.

12:00Then as we started to talk to more people, we sort of morphed this and literally built an exit like a Google sheet and morphed it into ICP like we had different IC potential ICPs as the row as each row because we didn't know like are we gonna sell to IT legal procurements finance right like all these people have to approve things that people are buying but who's gonna really like be the actual ICP buyer it might sound intuitive that yeah of course you would be selling yourself through to procurement and finance people which is the case, but it didn't feel that way. In fact, our first handful of customers are IT, which was actually an interesting signal.

12:36Does that tell you something in terms of sometimes you need to say no to customers? It's like sometimes big early customers can distract your product roadmap, can take you away from what you're actually meant to be doing. I find sometimes early signals can be misleading. Like you said there, the fact that IT people bought you does not mean that they're the buyers ultimately procurement as you're home. Do you know what I mean? You absolutely should, if you need to, should not close a certain type of customer, you should fire a customer. It happened to us when we were about a year old, we signed a customer that had hundreds of thousands of employees, sort of a pilot type engagement.

13:10And you know, I realized that the company was only 15 people or so, 12 to 15 people. Very quickly, an implementation, I realized, wait a minute, because I would go to every implementation call at the time. we're not going to be able to make this company successful without sacrificing an extremely extremely large percentage of our road map. And it's just not the right thing for us to do as a company. And so I'd have really great call with our champion there. And you know, I appreciate, I respect the fact that you're telling me that you guys can't make us successful right now and call us when you're right.

13:42And then we call them later. You know, you're after that. But that was a tough decision at the moment. It's bold and a lot of people take it because the validity that it brings to subsequent customers and to investors is real. Signing a massive contract really brings confidence and momentum, especially investor bases. I do want to just hone in on the right problem. I find a lot of founders aren't actually solving the right problem. You mentioned that it was pretty early that approvals was the right entry wedge. What advice do you have for founders on how to know whether they're solving the right problem and that discovery process?

14:15I think it comes down to repeatability. Really everything about building a company is about, in some ways it's about repeatability. It's like, okay, can you do this? Then can you do more of it? And then can you have other people do more of it? And then can you have you or people do more of it? You know, and maybe quality degrades, but it still works because there's a fit all from the market. And so really the question would be, are you able to repeatedly use that same type of pitch and narrative to the same type of person and yield the same type of result? And if the answer is no, then that means you kind of have to figure it out in some way.

14:47What do you think the biggest mistakes are that founders make then? Is it the fact that they don't nail the repeatability of that pitch, so to speak? Or is it the fact that they just go off to the wrong problems? I think there are a couple of common mistakes, so one getting free customers or design partners, which is I think you use feminism for a free customer. This is like a boom. You and I both know, dude. Every founder is like, I've got 12 design partners. And I'm always like, what does that mean? I understand this. Why do you not agree with design partners? So, so, Lou and I were very strict in our thinking.

15:19We decided, look, at the end of the day, if we pick an idea, we're gonna work on it more than anybody else. Like, we don't want to waste our own time. So, what we're gonna do is this. We're gonna make sure that the first 10 customers to be close, we're gonna close them cold off a LinkedIn. They're not gonna meet people we know, they're not gonna meet more of introductions, they're not gonna be referrals, nothing. They're gonna be cold because if they buy it, they always nothing in the world. Then they actually have this problem and they're willing to pay. And we're gonna charge real money for it.

15:44Now of course, when you're starting out, you have zero customers, of course you don't charge that much money, and it goes up over time, but they're gonna pay. And something material for us at the time. And I think a lot of the times, this is my second company, but I can just see how different my mindset has been this time around and the first go around. But like early on you're like, trying to keep your investors happy, you wanna make it feel like it's working. And the second time, or at least for me, it was like, look, we're just here, we wanna build a generous company. and they're like, we'd rather just know this is a bad idea quickly.

16:12So we'll go through here. How do you do it differently when you are just trying to make your investors happy versus doing it for you and doing it to build a big company? Oh, it's easy. You care about things like optics. You care about, you know, are the metrics all going up? You know, like all these little things and when you actually are just like, you know what, I just want to build a really big company. You're just here to make the thing work and you want to protect your own time. And actually when you do that, everything actually does start to look good. Oh, that's the mindset. So I cut you off.

16:39You said like design partners number one people make mistakes with that any other But glaring mistakes mistakes in terms of Solving the right problem and actually how they articulate the repeatability of that you said repeatability being the most important thing Oh, yeah I think I think like design partner and I think like being very clear like it's so easy to fall into like slightly customizing the product for each different type of customer you have. You have so few at the time you care about a lot of them, right? You don't want to have it so many churn. You've built something that's like a different, slightly different thing to five different people.

17:13This, I think, goes back to the theme of repeatability. I've seen so many founders do that too. You know, you can talk yourself into it. That makes it really harder, right? Because every, like, how do you prioritize feature requests? How do you message your product on your website? Like, are you speaking to this person or that person or this problem or that problem? You want to just make the edge getting more customers is like you need like a weapon and then you're like, you know Going into the world with you want the sharpest possible point. You don't want something that's what? Well, you mentioned repeatability time and time again there and for investors they say it's when you have repeatable and scalable processes that is when you have product market fit I just think product market fits the most bullshit thing ever because you you scale to a new channel, you scale to a new audience, you scale to a new pricing level, and fuck, you don't have it again.

17:59And so I'd love to just hear your thoughts. Like, how do you think about product market fit? Having had it with Zip, having seen it firsthand? No, completely agree. Product market fit is certainly not binary. It's like a complicated matrix, and like the first sell in that matrix is like the first set of product market that you have. But as you distribute, like you said, we're talking about platforms as you add more capabilities, more products, right? You have to go through product market fit for every subsequent product that you launch as a company. And then you have to do the same thing for every persona you speak with, every channel, every industry.

18:33I mean, it can get gloriously complicated, every vertical, right? You might, you know, if you sell the retail, versus you sell the financial services, just because you have market fit in tech doesn't mean you have market fit in financial services. Do you build out a verticalized sales playbook? And because you can have very distinct customer profiles that you can go after with that shop, shop spear. And it's much more effective to do that than have a horizontal product marketing approach and just kind of going at everyone with the same message. And for founders listening, is that the best way to do it?

19:01So we don't do that at zip. And I think it may be, like we don't verticalize ourselves. It is extremely, extremely expensive to verticalize your sales team. And at least from other founders that are much head of us that I've spoken to, like when people do it, it is at a much much much different level of scale. Why is it? Say you have incredible pull from I'm just using this as an example, large restaurant chains. They have a huge amount of buyers across different segments and procurements and nightmare. Why not have someone to go off to hospitality? It can be a hundred grand a year, quite young person, your job, hospitality.

19:36Does it need to be expensive? I don't know. I actually think that's the right approach. I think you actually who would strap it by having like a smart like zero to one type maybe an x -found or right like that type of person like Figure out because what you need to figure out is what's the messaging like are there any like specific systems They use that like we have never heard of you know like just get all that stuff working build up the right assets and positioning Just so you know your team is can be successful But then ideally you can just fold that into the rest of the organization And maybe you have a pocket of people that are focused on it if it's very specific But it depends on how work, like whether the horizontal messaging fundamentally lands or not, and it depends on the product.

20:15If it's not that horizontal, then you may need to verticalize sooner. Did you find it hard building out a sales team? You're a very product -led organization. You're a very product -led founder as well. Was it hard building out the sales team in the way that you have to and have done? Yeah, I mean, absolutely. It continues to be, right? I mean, there are always changes in how you sell. But yeah, I mean look we both for Lew and me. I mean we came from consumer we came from Airbnb, we had worked on consumer companies in the past so this is our first root awakening to hey this is how it works with sales teams.

20:49What was the root awakening? So many different things but first it was like understanding every component of a sales cycle right? I remember we have you know so many awesome sales engineers at ZIP today and initially I was completely skeptical. I was like I don't understand why would you when anybody you ever need a sales engineer. We can just have the accounting executive do the devil. You know, they should be able to answer the questions. And we realized like we were running into limitations around like technical questions. And like, you know, you actually do need somebody that has a more technical person.

21:18So it's a lot of first principles learning around how the actual process works. And it's also, I think the other big thing is it's hard to assess, right? Like product like you can look at metrics, not to say you can't in sales, but every metric you look at the more you zoom into, you realize like actually maybe you should be looking at the anecdote. Like, let's go listen to the gong call of where this actually happened. And it's like a human problem. It's not like a software problem. And that's just harder. I love it. The CPU of Spotify says the details are not the details they are the product.

21:49And it makes me think of that when you say about kind of drilling down and going into the weeds of a gong cool. That's where the importance is. The details are important. You know, one of the things I've learned is like confidence. For a salesperson talking to a prospect. One of the most important things is confidence. One, how do you measure that? But two, how do you fix that? It's very hard. That's what makes it so complex. How do you fix that? Is it a case of jeering everyone up and saying, Hey, you know, residual, you're a rock star? How do you give them the confidence to crush it on gong calls?

22:21Better enablement. More at that. It's like, like, when you're in this type of situation, you know what to say. And you can say it with confidence. Like, you can say that, yes, That's this thing, yes, our product does that. It does it really well. Here's the two reasons why. Here's what makes us different. It's just a lot of enablement at that, which is actually repeatability. Did you bring in a sales leader first, and they built out the team? Or did you bring in reps first, and then lay it on top of sales leader? The latter, we hired one sales person who was an AD in his past, and held a number of different roles.

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22:55Basically, I fired myself from a lot of sales job, right? Because I was just doing sales at that point, and then we brought him in and then, you know, he would just shadow everything, then I would like let him do the first call deck, but I would do the demo and then he started doing the demo so we sort of moves that way. What stage did you hand off sales? What was that like? And for founders listening, I think that founder led sales transition to, you know, someone else is so hard. What stage did you hand it off? And do you have any tips or advice on how to do that well? Yeah, yeah, really challenging.

23:25I think for me it was like, hey, I have actually, I feel like I've gotten to the point where now I'm doing first calls and I'm not really learning anything. I'm just having the first call to go get the deal. And when it started to feel like that, that's when I was like and Lew and I were both like, okay, now it's time because learning anything new, let's try to get a little bit more skill, right, with one more person. It was, it's a trust building exercise, right? Because you need to get the person ramped. Of course, you have no documentation, you don't have anything. I mean, it's just a multi, you know, four or five person, a couple of you have the time at most.

23:56And so you just spend a lot of time, you shadow everything and get more and more comfortable. So it's tricky. I have other founder friends who would hire like two. So there's some competition and then go from there. We did it. It's really hard. And then it's sometimes you have two not work. And then you're really in trouble. Because it's like, is it them? Is it me? Could just be them? It could be you. It's a night. And then you lose time. Can I ask you on the losing time element? I've had so many founders on the show before say speed is the most important thing in a company's success It's the biggest determinant of whether they get product.

24:30Is that true? Do you think or not? Absolutely, I mean, you know if you think about it right like you were to bet on you know one of two horses one Oruses like really thoughtful Planning and they've got a whole strategy. They're like they're gonna execute it but they're slower and the other horse Like actually doesn't have the best strategy but it learns quickly and it just like keeps changing path like which one's gonna get to the destination faster Unless the first one is perfectly right which almost certainly is not that that first horse is not going to be I would bet on the second horse and I think that's the mindset, you know We have internal like I would much rather bet on it on a zip that you know We all we sometimes joke internally, but but it's a way for us to push ourselves to get better We sort of talk about you know like how do we compete with the others it like in an alternate reality There's a clone of art like clone of zip in the alternate reality.

25:16How would we beat that clone? And usually the answers would do something, we would just iterate faster. Speed is actually really, really in advantage. You're not gonna be right, so you might as well just learn quickly and move on. The other thing is as companies grow, they just get slow. And so we really, really want it to establish as high of a watermark as possible, because when we were a five person company, I mean, we're certainly way slower than we were when we were a five person company. Just like we're much slower than we were when we were a hundred person company. Did you be the most mythical CEO if you could actually retain speed with scale?

25:45So don't worry about that. I've never met anyone like 700 of the biggest CEOs never has anyone done that my question to you though is like as much as one possibly can what would be your biggest advice on how to retain some form of speed With scale well one it has to come from you You have to lead by example as a founder like the founders have to lead by example It pleads into the rest of the company and you have to reward that You have to reward that and call it out and shout it out inside the company like if somebody does something Quickly and like they achieve some result even if it doesn't work out You should reward them for it and you should make sure other people see that that happened And that they were rewarded for it that sort of sets the DNA of the culture I think I'm gonna repeat ability can also solve for some form of speed because it makes things more known My question she that I really struggle with is like we actually have a pretty repeatable process in media companies in terms of how we do shows.

26:41Obviously every guest is they're an individual snowflake, but shows are relatively the same in terms of structure and how that composed. We can never lose creativity though. It's so important that our social team is so creative with each show. How do you retain creativity where people bring fresh new ideas and they're not just like, visuals set the repeatable playbook? That's a really good question, but it's empowering people to like speak up and rewarding like more off -the -wall ideas and like alternative approaches. Right and rewarding first principles thinking and a lot of that relies on like I would much rather invest in the person that has potential that maybe hasn't done the job before but like has a high ceiling because that person is more likely to think through the they don't have the experience or what are they going to do they're going to first principle the problem and so they're just generally more likely to have more original ideas and so I think a lot of this is like you can sort of culturally set this up if you have more managers and leadership in the organization that's actually come from the DNA of the company and you know high potential but maybe isn't like taking a playbook from somewhere else and cutting and pasting it into your company.

27:46There's a time and place for that maybe too so you have to balance it but I think like if you only do that you don't get as much creativity out of your organization. The other thing we try to do is have a lot of brainstorms. How what does that look like like a weekly brain? How does that look in reality. Oh, if we've got a problem, like some hairy like complicated problem, what we'll do is try to get not a very large group break, because then it's not productive, but a good group of like pretty diverse cross -functional people that are working on or touching this problem, in for an hour, at least what I found work out is like, all right, everybody takes 15 minutes and write all your ideas out.

28:19Yeah, I went on one and then we just go around and then try to whittle that down and then we end the meeting with like five ideas. Maybe Maybe two of them we would have thought of anyways, but there's three like pretty interesting ones that maybe we wouldn't have thought of and that's like one way It was so hard. How important is focus everyone's like focus focus focus But then you also want to encourage creativity people come up with great ideas How do you think about where to really focus your attention and resources versus when to focus? I think it really depends on the problem and the function like for example I think marketing is such a diverse function right because it encapsulates product reckoning and growth and like content I've said, Mark, like all these different things, like I actually think like having marketing be quite unfocused is actually okay in its execution.

29:04Messaging needs to be focused. Well, execution actually can be unfocused. And I think it's actually okay in some cases like that. And I don't know, maybe that's a controversial statement, but I don't think you have to be that focused in every function. Can I ask you, when you think about speed being the most important thing, what was the decision you made with speed that with hindsight should have taken more time and should have had more consideration also put into it. Oh, that's a really tough question. I also won the other day and they said, my urge, I said, you are fucked. Ha ha ha ha ha ha ha ha.

29:34And so, okay. Actually, I'll give you a great example. So my, so it was my second company. So my first company was a company called Flight Car. TLDR, we would give you free or for parking by renting out your car. So somebody else fully insured. And I dropped that, I cost to the company. And I remember I called my friend at the time and said, hey, you know, we're both bored, like, Tara, you down, like, why don't we do a company? but he was like, sure. And I remember I grew up in New Jersey, and so of course, New Jersey, so at the time, at least, you know, you would go to Panera Bread, like that's where you would go hang out.

30:05And so we were like, all right, let's go meet up with the Panera Bread tomorrow for an hour. Whatever the best idea is that we can come up with in an hour, let's just do it. And I remember that hour, this was in 2012, I think. He was telling me, he was like, hey, there's this thing called Airbnb, and people are sharing their houses with each other. They were like, really? I never heard of that. And then we sort of one thing that's another like what would they do with their cars? And if they're gonna do it their cars, maybe they do it at the airport because they're by definition traveling They're not using their car And so that was the idea that we came up with in that one hour We did it for five years literally.

30:37I would never do that again Like we took exactly the opposite approach when we started to say but like I mean that's like what you pick your idea And you're like working on I mean you're like of course you didn't change right? We didn't then you're I mean you're just so deep in So that was one, like if you're gonna do a company, don't tie box yourself to one hour. Should you have quit earlier? It's like one of those things where like, I would do everything differently but have no regrets. I mean, what I learned from that company was, it was a very operational business. I mean, at our peak, we had 17 different airport locations, hundreds of hourly workers, washing cars, and picking up people that got me to my airport, right?

31:09I learned so much in terms of like, what it takes to be operational business, and boy, is it, I mean, is it easy to run a P2B SaaS company? We have our problems with like, it's not like we're constantly gonna be running on a money, like, you know, like, you don't have to worry about any of these things. Like, you don't have like 24, 7, 365, like, subordinated with like emergency situations, like, just not that. So I have this with founders a lot who will pitch, and then you're like, I understand, I understand the premise of Flake, it's just a really hard business to work with all the different aspects that need to come in to play together for it to work.

31:40For that margin to drop to the bottom line, I'm not saying it won't work, there's just easier things to go after to build a massive business. And I always feel quite guilty saying that. No, no, yeah, exactly. Like there are easier paths to success. And that was totally, I mean, that's the analogy that I used in that business. It's like, you know, the margin you make, it's like squeezing all the juice out of a lemon. The last drop that falls out is your margin. So if you screw up halfway through squeezing the lemon, you don't need to squeeze the rest of the lemon to understand how the movie ends.

32:08And that was the business. That was the business. Were there any other big lessons from that business? I need so many things, man. But one was do a B2B SaaS company next by far. Two, I think you don't, this is something that I think I learned later at Airbnb, but like, you know, the bar of like what a really good product designer is like, when you go into a cold, you've never worked anywhere. Like you kind of don't really know. You're just feeling your way around things. And so I think that Christianity, the hiring in the talent bar was something that working in Airbnb later on, I think really personally helped me with, which is something that I didn't have back then.

32:44I agree with you, which is why I have this kind of investment thesis, which my team killed me for, especially for saying it out loud. They terrified the first time founders weren't come to us. But I don't like the first time founders like I like Zero Lunch Purs, because you've just seen it. You know how to do hiring processes. You know what great looks like. You've seen the mistakes. You've made them. We're leveraging the mistakes you've made before. Do you agree with that thesis of like, yep, Zero Lunch Purs, you've just made the mistakes? like, no, there's beauty and naivety in use in upside thinking.

33:13For me as a second time founder, I was very, very determined. Lou and I both were to work out a company, working on an idea that had high execution risk, low fundamental market risk and then to the product risk. I think as a first time founder, you're actually much more okay, maybe because you don't know any better, to take on a lot more market risk. And so you can actually have really large outcomes, So, right, like, a lot of the social media companies, I guess are good examples, but Snap, like Snap is not a company that, like, it carried a lot of market risks, right? Like, the whole thing. And, like, I'm not sure someone would do that as a second time found, but it's obviously a wildly successful company.

33:49And so, like, you can have outcomes like that, but, like, you almost can't have as a second time found. Maybe because you're just too jaded about the world or too bad. I'm gonna go there, even though I thought that I wouldn't. You said, number one lesson was do B2B. I had Trey on from Founders Fund, And he said, serial entrepreneurs in SAS are like George Clooney selling tequila. In the way that seriously, you have a massive opportunity with your skills and talents, and you decide to do B2B and to price SAS. That is not serving the world. What do you say to that? Well, I would say it's a little bit different than Sally Tequila.

34:26and I would say that if you take what we work on as an improvement, I mean, there's like 11 times as much money that moves hands between businesses, then moves hands between the consumer and the business. So much money that moves hands. And if you can make that just a tad bit more efficient across the board, you actually create so much value in the economy that's being lost. And that ultimately, even this, of course, takes so many steps, but that does carry over to consumers. My second question to you is I spoke to Annie Raghawani and he said to me to double quick on what you just said that which is the lessons learned from Airbnb.

35:02What was something the lessons learned from Airbnb on you mentioned what great looks like so maybe that and any others? It was just so helpful for me to see Brian Chesky, you know, see a Airbnb just how the level of attention to detail when it comes to the Airbnb product. Remember design reviews where to his credit he would be able to detect that some of the is facing us off, just on our mobile app, or just like really, really focus on detail. And what that does is, of course, do those extra, I don't know, 10 pixels of white space in of themselves matter? No, but they matter a ton in terms of what that says to the company, and where the bar is for quality of the product.

35:42Just like speed, right? I think product quality, design bar, like all of that also, I think ultimately is a cultural thing and it comes from the founders. But can you have that? Can you have that micro -management, that intense focus on the pixel spacing and the speed of execution that is required. I think so, but it's because you have to focus on different things. You can't micromanage everything. You have to be selective, I guess, is the right framing about what you micromanage. Because it has to be, you have to micromanage the few like critical things that are like very, like their core values for the company.

36:15That doesn't mean you can't be quick in other areas. What are you selective in the areas that you micromanage? And what areas are you you deliberately not selective in what you might encourage. You know, I think I spend a lot of time in the actual, like, I mean, we were talking about sales, just like how, how human the problem is and how at some point you have to look into the anecdote, spend a lot of time, a lot of time on that. Everything from gone call, listening, like getting into the details of like, what exactly was said, like, what exactly is happening, like, why is this person, you know, performing better than that person?

36:48Like, can we take something that they're doing? Really double clicking on that and not trying to manage the go -to -market organization by metrics along. Because it's so hard to actually affect change that way. That's probably the number one. And which one of you like, fuck it, I'm happy to not micromanage that. I can clearly delegate that and it's not a problem. You know, my job, I think, in many ways, is to focus on what's not working. There's an area of the business that seems to be doing just fine. That doesn't mean it won't break, because it probably will. But right now, it's not the thing that's on fire, or it doesn't look like there's some smoke there.

37:20You kind of let it let it go. What's not working right now? Oh, I mean, there are always things that working. One of the things we're working through is how best to scale some portions of our sales organization, like our business development organization. It's a tough job to call people, to email them, send a message to someone, then get interest, and how do you sort of scale that team, you know, maintain productivity, and allow that team to have like a great career path into the e -wall, which is something we're really proud of. How much of net new client acquisition is from that team today? I mean, we're largely about business.

37:58So, lodging out about business. That's so interesting though, for me as like someone in this industry, I think the brand is so strong, the investor sentiment is so strong. I think it would largely be an inbound strength of brand business. No, I mean, I think a lot of enterprise sales and enterprise go to market it is given how top -down it is, is actually quite, quite outbound. And it will shift over time for us to, and I can already, in fact, is, you know, and at larger percentage than it's ever been in history of the company, but the majority is still outbound, especially after we go, after different industries, into the enterprise, so forth, right?

38:34Like, it's also about like, hey, we talked to somebody in an organization, we understand there's a problem, we have to get to the right person, like literally the right person. And that's very hard to do when you're targeting an account and an organization in an inbound way. It's also super hard because you don't have like clean day through I find on titles within companies. What is one thing in one company is another thing in another company and actually buyers a very differently place according to different companies. She said, I mean, it's not like great then. Nope, completely agree. And especially when you, you know, sort of add to that different geos, different countries like it just gets even more complicated, very hard to tell.

39:11Why we may be getting into some ways, but I'm just like skating the outbound side. I am just like, I think AI will actually destroy outbound in many cases, because it will just create infinite supply of messages, or infinite supply of whatever channel that is. And so I think you actually see the complete removal of it. I don't know how you think about that. I don't see it quite as a complete removal. All that, look, maybe in 20 years, like, who the hell knows. But I do think like there's an opportunity to increase the opportunity. And we're trying out a bunch of stuff using chat and GPT to, I mean, there's just so much manual work that goes on that you can actually start to automate even today.

39:48I mean, we'll see. I'll probably have a better read in six months for a year. In terms of like giving the team that trajectory you mentioned from my BD and outbound to A's and other parts of the sales function, it's really hard to motivate teams when they're not together physically. I know that you've been a proponent of back to office. Can you talk to me? How do you get excited about people going back to office and returning to physically co -locating? Yeah, it's such a tough thing, especially for companies like ours that were born right in the heart of the pandemic. And it's challenging because it varies by function.

40:22And one of the things we do is for engineering product and in design, we mandate two days a week, specific days, one dozen, third days, in the office. That actually was born from, you know, what we found was that it There's actually, I mean, a lot of engineering is like a make your job, right? And design, like you're, like you're writing code, you're like you have to really focus. I think what we found from a lot of our early focuses that it was kind of just like lonely to like just do that. Like they were craving some more like, some more social engagement, some more engagement in some way, shape or form.

40:49And we decided, and then they were drowning in meetings, of course. And so what we decided to do is we prioritized in office days and then try to push all the meetings to happen in office days so that there was like other times you get like a really healthy balance. I think an interesting thing that we did is so early on when we started the company Lou and I both bought these Facebook portals which I think is now I don't think Facebook sells those anymore I still have mine is right there and we would keep a zoom meeting going the entire day because we're in different locations during the pandemic So for 12 14 hours 16 hours a day we just had just a zoom meeting then we as we grew the team We had more team members join every morning you would just, if you worked at ZIP and you would just join the same Zoom meeting and keep it on video, then on mute.

41:33And so it was kind of cool. So when we up to like 20 or so people, we just had a Zoom meeting with everybody just hanging out. But what really helped was initially just me doing sales. And so whenever I was doing sales, any sales call, I would leave myself un -bueded. So even if you weren't in GeneratZip really early, you would be listening to every single sales call. There's only one happening at one time because we just want to meet. And so you would listen to everything. Like I think we really accelerated like internal enablement and learning at that time. But anyways, I think that's part of the reason why people were craving some level of social engagement.

42:04Can I ask what finial biggest hiring mistakes you learn so much from your mistakes? What have been your biggest hiring mistakes? And how did that change your thinking on acquiring and retaining great talent? And number one thing is like over indexing on someone that's done it before at like a similar level of scale. I think for even for a lot of investors, I think it's like people love the press release hire. All this person did it, they took them, they did this and they took it from 100 to 250 of ARR or whatever it is. And so we should just get them a pogum in here and it would be perfect fit and similar sales cycle or whatever.

42:39I'm not saying that can't work, it totally can, but you would incur a lot of risk. Because it also, every business is very different, every situation is extremely different. The same playbook certainly won't work and just will the person be able to figure out how to change the playbook enough? Right versus versus you know, maybe you bet on the person that like has proven themselves out in whatever thing They're doing and have a lot of potentially just get get one level above and you have an honest conversation about look You're gonna step into these you know bigger shoes. We're taking a bit of a risk here So are you and so you tell me if you think it's not working and I'll tell you if I think it's not working And let's just like both keep the you know finger on the pulse It's not that's not the right call all the time but I think it's actually the right call.

43:18Much more often than people realize. And you never get recognized for it. How quickly do you know about high? Oh, that's a tough question. We've been slow in the past. You always feel like you could have been faster. Look, I think the way I see it, if I feel like that's the case, I'm the last one to know. Right, because their team probably has figured that out already for months. Their peers have figured it out for months. So it's like, how do you find out faster? One of the things that we do is, like there are obviously trusted OG people that like I trust that I know are great. And you know, trying to maintain a close dialogue with people like that so that they can temperature check, right?

43:53It doesn't mean that they're always right. Certainly not the case. There's always like gray areas and a lot of new ones. But if you start to hear feedback that somebody's not performing from like a lot of people that you know are high performers, that's a massive red flag. And so can you use those types of people who are sort of spread out throughout the organization to give you just better signal earlier. I always remember Mattis Leuchin telling me when there's doubt, there's no doubt. And I'm not sure if it's right, but it just always stuck with me. You know, when you doubt someone's ability, there's no doubt that they're probably not the right person for the job.

44:24I don't know if that's true. I think that's probably true 8 out of 10 times. And the challenge is that it's probably not true true out of 10 times, but is it worth continuing to see if it's... Do you agree when someone's on a performance review? Just don't bother. It's always a slippery slope. I actually don't agree with that. I'll tell you why. If that is the case, that means you probably are doing the performance for a few too late. Or more of the performance plan. I assume that's what you meant too late. You're not giving the person an opportunity to like. Like, you haven't detected it earlier, I guess, and given them an opportunity to course correct earlier.

44:57Did you worry about raising too much money too quickly? So, this was my first company. I was certainly should have worried. We didn't worry quite as much because we knew we were going to maintain the discipline. Another mistake I think a lot of founders make is just higher too much. so early before they like know without a doubt that they have like clear product markets. I think that's so important though, like to really keep a small team because at that point in time, because say the thing is it working, right? Like if you know like if you're working with five six people you're hanging out all day, you're all working together, you can be like, hey guys, like actually like this is a bad idea.

45:29We should do this. All right, we should change it, right? You can do that because you have the trust, but when you have 20 people, you cannot possibly have that type of relationship with the other 19 of you. And you just sold them. You were like, oh, this is awesome company. It's great and blah, blah, blah. If you're at that point in time, you can't actually, actually I was just wrong, even though I was two weeks ago. Because of course you have that in your head. Yeah, maybe this isn't the right one. We'll figure out, but maybe it's not the right one early on. And so we certainly raised a lot of money then, and then later obviously, well, it has that point, but we were very disciplined.

46:03No matter what money we had in the bank, we were not gonna hire more. I mean, there was a point when we were a small company and cashflow positive because we had just held back higher it so much. And then we really unlocked the gates when we felt like we had coffers. Price wise, investors will pay up for assets that are great with great founders like you and Lou. We worried about the price blunt need just being very, very high in such a short space of time. It means you have to live into that valuation. It's hard and we see a lot of people struggle with that today. How did you think about that at the time?

46:33We were just so confident that there's like so much marketing and like the growth rate That we had and have it was more just an opportunity to like do something We maybe would have done a little bit later and just do it now and that's how I thought about it But so we had that confidence in we have confidence now Regile your constantly speaking to people investors employees customers What question do you not get asked that you should get asked more? Huh, that's it really that's a tough question. Do you see yourself running zip and 20 years time. Yeah, absolutely. We wanted to start a company that was going to be a generational company.

47:08At the time this was 2020 when we started a company, in 2040, it would not only be around, but people would know what it is. It's so funny. One of my biggest turn -offs when investing is when you hear like a fan say, hey, when I do my next company, or I'm doing that as well. And I've interviewed you so many of the best. And this is that life's work. Like this is the only thing they focus on. And that is such a big sign for me. I mean, not one survivor or thought of something after it. Like, there is no after. Like, there's no. Not one. Listen, I want to dive into a quick fire round. So I say, short statement, you give me your immediate thoughts.

47:42Does that sound okay? Okay. Okay, so what if you changed your mind on most in the last 12 months? I think it's probably my, like, how I managed my day to day. So there was a point early on when we had like a huge spreadsheet and every single person in the company we just literally right out there to do this for the day in each tap in the spreadsheet. Obviously that broke after like 10, 15 people. My current thing is I have a no card and I actually write out what I'm going to do for the day on the no card. It goes in my pocket and I cross it out and I throw it out and I have a fresh one tomorrow.

48:14What are you most concerned about in the world today? Well, this might be this might be right. I mean we've got a lot of tracks that we're obviously going on around gender of the eye and I'm not going to open up all the can't worms but you know you just read such concerning headlines and the news about things that can happen things that we're now going to be able to do with it. Yeah you sort of wonder where does that leave us? You've been just a handful of years. Does that worry? I take the view that bluntly we always over estimate adoption in a year and underestimate it in 10 years and I think this is like oh everyone's gonna have no jobs and all of the gross over -dramatization is like a 94 % of European corporates don't know what notion is.

48:55No, no, I actually, I agree with you. Like I think adoption in the enterprise and all of that will be slow. No, I think what actually concerns me is just like adoption for like malicious intent, like you know, to imitate somebody's voice for fraud or you know, like stuff like that. It's like, yeah, that's actually really concerning. I don't know what the solution is to that. And for people that want to commit that, I bet the adoption's not, it's pretty quick. What do you think of the biggest ways VCs and found as a misaligned? It's like the time horizon maybe, how much the outcome matters. Right, I mean, ultimately like for an investor, this is one of whatever number of full -year companies they have, and of course the dynamics are such that only one may be multiple.

49:32Lucky will return the fund or whatever, and they don't need every single one to work. And as a founder, I mean, this is your life. Just fundamentally, there's gotta be some level of misalignment. Again, it's not, it's not like an incorrect intention. It's just, it's just different. If you could choose someone to add to your board who's not on your board today, it can be anyone. Who would it be and why them? Frank Slutman, I'm a huge Frank Slutman fan and read, I put up, recently Frank Slutman. What's the biggest sin of the zero interest rate environment? You were born in COVID, so to speak. What was the biggest sin of that time period?

50:05I think like hiring to solve problems, so many companies like, oh, you have this problem, great, hire. And it's like, wait a minute, wait a minute. Like do we really need to go hire a whole human just to solve the problem? Or is there some other better way? And I think it just like was easy enough to do that. There was enough capital. It was just it was the easy lazy answer. And so I think a lot of companies were affected by that. What do you know now that you wish you'd known when you started Zip? How hard it is to actually build a world class product in this space? And how complicated it can be.

50:35When Luda were at Airbnb, at different points in time, we both worked on search. And I thought that was complicated. And boy was I wrong. I mean, this can be gloriously complicated. I mean, some of our customers are gonna be enterprise, for example, like over a thousand types of questions that can get asked, with all sorts of different logic, based on the thing that it is that you're buying. And, you know, 20 plus different types of risk reviews a lot. I mean, it can just be so complicated. Why do you wish you'd known that? Because like, when you think about the, I wish I'd known this because then I would have done this differently.

51:03So if we start, if I give a mind as long, I wish I'd known the importance of video in this age of media, because I would have started YouTube very much earlier. If that was your answer, how difficult it is to build a world -class product for this segment? What would you have done differently than as a result of having known that? That's a good question. I think we would have probably made some investments in our architecture that would have allowed us to build out, you know, we have a platform today but to build out more of a platform without having to, you know, expend a lot more resources that we've had to do as of the last six, eight months.

51:34To be fair, to be fair, maybe the answer is actually, I didn't know we wouldn't done that, because it would have just taken more time and we wouldn't have put in the engineering research just because it wasn't the right thing to do at the time. I could see the alternative too. My favorite thing is kind of like nothing's ever as good or as bad as it seems and just life goes on. Do you know what I mean? Yep, you have limited information. You do the best that you can. Okay, so we're 2044. 2044, what is Zip then and where are you in 2044? Well, I sure as hell, I'm still here thinking about procurement and that's where I think we can be as a product.

52:09If you think about it, right? Think about the notion of an approval, significantly over 90%, even over 95 % of the time, people are approving. Like if there's an approval, they're approving. You bet they're approving. Like the rejection rate just across the board, extremely low. And so when you think about that, you're like, well, that's kind of a deficient process. Like you basically have this thing where people approve stuff and then so that they can see it and then they like basically approve it anyways. So can you actually instead of managing a process that can you just not need to do approvals because the software can do it for you?

52:41We're not there today, but there's definitely a world. I mean, and hopefully a lot sooner than 24, 24, 24, or where you can say, now I actually like, right, like you don't need to have a human go in their review of the thing and then approve it. In 20 years, I think people will be like, really, you had humans like reading these documents, like thinking about them and then approving them. That seems dumb. Listen, the reason why I do the schedules, I have no reason for. I used to stick to them as you can tell, but nowadays they self -zero point. Thank you so much for joining me, Rujul. This has been such a fascinating and varying discussion, but you've been fantastic.

53:13No, thank you so much for a pravening. I just love shows like that. I always started 20VC because I wanted founders to listen, and the biggest thing for me was I wanted them to get out a notebook, take notes, and learn. I think there were so many lessons there from Rujul on how to scale a sales team for the first time as a more product oriented founder and CEO. If you want to see the video you can check it out on YouTube by searching for 20VC, that's 2 -0 VC, but before we leave you today, I want to talk about Cooley, the global law firm built around startups and venture capital. Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 60 plus years working with VCs.

53:54They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund's lifetime. We use them at 20 VC and have loved working with their teams in the US, London and Asia over the last few years. So to learn more about the number one most active law firm representing VC backed companies going public, head over to coole .com and also coolego .com, coolees award -winning free legal resource for entrepreneurs. and speaking of providing incredible value to your customers. Traveling expense are never associated with cost savings, but now you can reduce costs up to 30 % and actually reward your employees.

54:33How? Well, the van rewards your employees with personal travel credit every time they save their company money when booking business travel under company policy. Does that sound too good to be true? Well, the van is so confident you'll move to their game changing all in one travel corporate and it spends Super app that they'll give you $250 in personal travel credit just for taking a quick demo, check them out now at navan .com forward slash 20VC. This podcast is sponsored by Squarespace. Squarespace is the all -in -one website platform for entrepreneurs to stand out and succeed online. Whether you're just starting out or managing a growing brand, Squarespace makes it easy to create a beautiful website, engage with your audience, and sell anything from products to content, all in one place, all on your terms.

55:20What's blown me away is the Squarespace Blueprint AI and SEO tools. It's like crafting your site with a guided system, ensuring it not only reflects your unique style, but also ranks well on search engines, plus their flexible payment options, cater to every customer's needs, making transactions smooth and hassle -free, and the Squarespace AI, it's a content wizard helping you whip up text that truly resonates with your brand voice. So if you're ready to get started, head to squarespace .com for a free trial, and when you're ready to launch, go to squarespace .com, slash 20vc, and use the code 20vc to save 10 % of your first purchase of a website or domain.

55:57As always, I so appreciate all your support and stay tuned for an incredible episode of 20 growth on Friday, with the one and only Adam Growth, one of the masters of growth from Heroku, from Salesforce, from Dropbox, that one is not to be missed.

From the publisher

Rujul Zaparde is the Co-Founder and CEO of Zip, the world’s leading Intake-to-Pay solution, adopted by leading enterprises and startups including Snowflake, Canva, Airtable, Webflow, and others. In 2023, Zip raised $100 million in a Series C round, valuing the company at $1.5 billion. Before founding Zip, Rujul was a Visiting Partner at Y Combinator and a product manager at Airbnb.

In Today’s Episode with Rujul Zaparde We Discuss:

  1. From Airbnb PM to $1.5BN Founder

  • How did Rujul’s first company fail? What were his lessons?

  • What did Rujul learn from his time at Airbnb?

  • How did Rujul come to co-found Zip? What was the aha moment?

  • What did Rujul wish he’d known when he started Zip?

  1. Standing Out in a Hyper-Competitive Market

  • Why did Rujul pick such a competitive market? How did they stand out?

  • Does Rujul think founders should focus on pain points or platform solutions on day one?

  • What is Rujul’s advice to founders who are in the discovery process?

  • Does Rujul agree with Trae Stephens @ Founders Fund that serial entrepreneurs doing B2B enterprise SaaS are wasting their talent?

  1. The Biggest Lessons Scaling Zip to $1.5BN Valuation

  • Which key moment caused Zip to accelerate?

  • Why does Rujul think speed is the most important element in startups?

  • Why does Rujul not believe in design partners?

  • Why does Rujul believe repeatability is the most important thing when pitching?

  • Does Rujul think AI will destroy outbound sales?

  1. How to Hire & Manage Teams

  • What was Rujul’s “rude awakening” building a sales team?

  • What was Rujul’s biggest hiring mistake? What did he learn from it?

  • How does Rujul decide where to focus his attention and resources?

  • Why does Rujul believe younger managers are more creative?

 

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