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

Rujul Zaparde
I 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 20 VC with me, Harry Stubbings.

Harry Stebbings
Now Zip Zip is one of the fastest growing companies in B two B. They are the world's leading intake to pay solution and they raised $100 million in a Series C round from some of the best in the business in 2023, valuing the company at $1.5 billion. Today. We have their co founder and CEO Rajul Zapade 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, Rujol was a visiting partner at Y Combinator and before that was a product manager at Airbnb.

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You have now arrived at your destination. Rajul listen, I heard so many good things from Anna Khan, from Ali Rao 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 Raju? Yeah, you know, that's a tough question. What I do. So what I do remember is that I was always even, like, I mean, certainly high school, but even in middle school, like, I was always with my friends.

Rujul Zaparde
Like, we're always doing some, like, business thing, and, 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. And, you know, the early two thousands. 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 can report me at this, at this number. Most of them are for commercial vehicles. And we had started something like that for teen drivers. We certainly couldn't drive at that, at that time.

And so we sold some bumper stick, 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 v one? Do you agree, or do 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. And 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, 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 so responsive and so intuitive to their feedback. Tell me, dude, how are we going to get onto learnings from past? But just in terms of zip, why did you choose this?

Harry Stebbings
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. Lou was an engineering leader at Airbnb.

Rujul Zaparde
I worked as a product manager. What happened was that I remember actually one day we woke up to an email message saying, hey, Rajul and Lou so and so has left the organization. You guys have been designated as the business owners of our contract with this large contract software contract, and 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, what we had to do was we were told, hey, you have to go to our ERP system, create a pr. So we both looked at each other. We were like, sorry, what? And the person was like, oh, it's a purchase requisition.

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 picked something. And then, of course, later on it asked, what's the GL code?

And we're like, we don't even, what is a GL code? 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.

We select something, hit submit I remember we distinctly went back to the procurement person we were assigned to, saying, hey, we're done. Thumbs up. Like, just let us know when it's approved. And he said, no, no, no. You're not going anywhere.

That's just the pr. 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, oh, also, it's a software renewal. So you have to go raise an IT ticket over here because the IT team needs to renew. 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, really sorry. I 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.

Harry Stebbings
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 today is, like, 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, you know, procurement or spam management, and it's like, ad with big names. When you looked at it, were you not like, my christ, there's a lot of players.

This is not attractive because it's so competitive, in a sense. Absolutely. But there's. There's a. There's a pro and a con.

Rujul Zaparde
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.

Harry Stebbings
But actually, Rajul and Lou have a 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? It's a great point. It's an education problem.

Rujul Zaparde
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. I think this person's just not, they're not there yet, or a later adopter, 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. It's a big problem to go after.

Harry Stebbings
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, how do you think about that? You'll eventually get to the latter. But I think first off, like, I mean, 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 pain point that somebody will be like, you're right, I need that thing. It doesn't exist otherwise in the world for me. Because what, what actually happens is when you have a platform, other people have platforms, too, and they all do everything.

Rujul Zaparde
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 in the world. No 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 your wedge. With the first wedge that you had, that first pain point that you identified, did it immediately sell? Like, was there immediate market pull?

Harry Stebbings
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 sort of convince ourselves and be able to better explain what we're doing to our prospects. So to your point about product marketing, it's, you know, you have to start with the positioning and the messaging. And that probably took us six months. Once we started to figure out how to, like, explain what we're doing and clearly differentiate it, it certainly, certainly accelerated.

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 rote in our approach here every week, actually, initially it was every day because we had so many calls.

Rujul Zaparde
And then we were like, we don't need to review this every day. We did it every Sunday. We would write out our quote unquote investor pitch, which is like a couple sentences of, like, what zip does, but the investor view of it, talking about, like, the market, that kind of thing, and then the customer pitch at one point where we're looking at both of those in one Google Doc every single day, and we'd be like, what did we learn today? Like, 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 a point 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. Then as we started to talk to more people, we sort of morphed this and literally built like a Google sheet and morphed it into ICP. Like, we had different potential icps as the row, as each row, because we didn't know, like, are we going to sell to it?

Legal, procurement, finance. Right? Like, all these people have to approve things that people are buying, but who's going to really, like, be the actual ICP buyer? It might sound intuitive that, yeah, of course you would be selling your software to procurement and finance people, which is the case, but it didn't feel that way. In fact, our first handful of customers were it, which was actually, you know, interesting signal.

Harry Stebbings
Does 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 is your home.

Do you know what I mean? You absolutely should. If you need to, you 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.

Rujul Zaparde
And I realized, I mean, the company was only 15 people or so. Twelve to 15 people. Very quickly at 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 roadmap. And it's just not the right thing for us to do as a company. And so I had a really great call with our champion there.

And, no, 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 ready. And then we call them later a year 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 to especially investor bases.

Harry Stebbings
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 actually 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, I think it.

Rujul Zaparde
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 even more people do more of it? You know, and maybe quality degrades, but it still works because there's enough fit pull from the market. And so really the question would be, are you able to repeatably 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. What do you think the biggest mistakes are that founders make then?

Harry Stebbings
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 that a couple of common mistakes are one, getting free customers or design partners, which is, I think, a euphemism for a free customer. This is like a boom. You and I both know dude, every founder's like, I've got twelve design partners, and I'm always like, what does that mean?

I understand this. Why do you not, why do you not agree with design partners? So Lou and I were very strict in our thinking. We decided, look, at the end of the day, if we pick an idea, we're going to work on it more than anybody else. We don't want to waste our own time.

Rujul Zaparde
So what we're going to do is this. We're going to make sure that the first ten customers we close, we're going to close them cold off of LinkedIn. They're not going to be people we know. They're not going to be warm introductions, they're not going to be referrals, nothing. They're going to be cold because if they buy it, they owe us nothing in the world.

Then they actually have this problem and they're willing to pay and we're going to charge real money for it. Now, 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 going to pay and something material for us at the time. I think a lot of the times, this is my second company, and I can just see how different my mindset has been this time around than the first go around. But early on, you're trying to keep your investors happy.

You want to 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 want to build a generational company. Like, we'd rather just know this is a bad idea quickly so we can. Go, 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. Well, 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, and when you, 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 wanna protect your own time. And actually, when you do that, everything actually does start to look better. That's the mindset. So I cut you off.

Harry Stebbings
You said like design partners, number one, people make mistakes with that. Any other 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.

Rujul Zaparde
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 and you have so few it that actually care about a lot of them. Right? You don't want to have somebody churn. You've built something that's like a different, slightly different thing to five different people. This 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, it 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 Persona or that Persona or this problem or that problem? You want to just make the edge. Getting more customers is like you need like a weapon that you're like, you know, going into the world with and you want the sharpest possible point. You don't want something that's blunt. Well, you mentioned repeatability time and time again there.

Harry Stebbings
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 fit is the most bullshit thing ever because 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. And 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.

Rujul Zaparde
Product market fit is certainly not binary. It's like, 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, I mean, 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. I mean, it can get gloriously complicated, every vertical, right? You might, 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 verdict, Clyde sales playbook then?

Harry Stebbings
Because you can have very distinct customer profiles that you can go after with that sharp shops beer. 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. So we don't do that at zip. And I think it may be like we don't verticalize our sales.

Rujul Zaparde
It is extremely, extremely expensive to verticalize your sales team and at least from other founders that are much ahead of us that I've spoken to. 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 are nightmare.

Harry Stebbings
Why not have someone to go after hospitality? It can be 100 grand a year. Quite young person, your job, hospitality, does it need to be expensive? I don't know. I actually think that's the right approach.

Rujul Zaparde
I think you actually bootstrap it by having like a smart, like, zero to one type, maybe an ex founder. 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 out 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. But it depends on how, like, whether the horizontal messaging fundamentally lands or not. And it depends on the product. If it's not that horizontal, then you may need to verticalize sooner.

Harry Stebbings
Did you find it hard building out the 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 had to and have done? Yeah, I mean, absolutely.

Rujul Zaparde
And it continues to be. Right. I mean, there are always changes in how you sell, but, yeah, I mean, look, both for Lou and me, I mean, we came from consumer, we came from Airbnb. We had worked on consumer companies in the past. This was our first rude awakening to, hey, this is how it works with sales teams.

Harry Stebbings
What was the root awakenings? So many different things. But first, it was like understanding every component of a sales cycle. Right. I remember we have so many awesome sales engineers at Zip today.

Rujul Zaparde
And initially I was completely skeptical. I was like, I don't understand. Why would anybody ever need a sales engineer? We can just have the account executive do the devop. They should be able to answer the questions.

And we realized we were running into limitations around, like, technical questions and, like, you know, you actually do need somebody that has a more technical person. So 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 it, 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 CPO of Spotify says the details are not the details, they are the product.

Harry Stebbings
And it makes me think of that when you say about kind of drilling down and going into the weeds of a gone 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?

Rujul Zaparde
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 geeing everyone up and saying, hey, Rajul, you're a rock star.

Harry Stebbings
How do you give them the confidence to crush it on gone calls better. Enablement more at bats, it's like when you're in this type of situation, you know what to say and you can say it with confidence. You can say that, yes, this thing, yes, our product does that and does it really well. Here are the two reasons why. Here's what makes us different, right?

Rujul Zaparde
It's all, it's just a lot of enablement at bats, which is actually repeatability. Did you bring in a sales leader first and they built out the team, or did you bring in wraps first and then lay it on top of sales leader? The latter. We hired one salesperson who was an ad in his past and held a number of different roles. Basically, I fired myself from a lot of the 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 moved that way. What stage did you hand off? Sales.

Harry Stebbings
What was that like? And for founders listening, I think that founder led sales transition to someone else's 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.

Rujul Zaparde
Really challenging. I think for me, it was like, hey, I've 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 Lou and I were both like, okay, now it's time because we're not 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 four or five person company at the time, at most. And so you just, like, spend a lot of time, you shadow everything and get more and more comfortable. So it's tricky. I have other founder friends who hire, like, two, so that there's some competition and then go from there. We did.

Harry Stebbings
It's really hard. And then 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 pronounced. Is that true, do you think, or not?

Rujul Zaparde
Absolutely. I mean, you know, if you think about it, right, like you were to bet on, you know, one of two horses. One horse is, like, really thoughtful planning, and they've got a whole strategy. They're like, they're going to 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 it's not. 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 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 other zip? Like, in an alternate reality, there's a clone of art, clone of zip in the alternate reality, how would we beat that clone?

And usually the answer is, we do something. We would just iterate faster. 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. The other thing is, as companies grow, they just get slower.

And so we really, really wanted 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 100% company. Dude, you'd be the most mythical CEO if you could actually retain speed with scale. So don't worry about that. I've never met anyone like 700 of the biggest CEO's.

Harry Stebbings
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.

Rujul Zaparde
Like, the founders have to lead by example. It bleeds 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 and the culture.

Harry Stebbings
I think kind of repeatability can also solve for some form of speed because it makes things more known. My question to you that I really struggle with is, like, we actually have a pretty repeatable process in media companies in terms of how we do shows. Obviously, every guess is there an individual snowflake. But shows are relatively the same in terms of structure and how they're 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, Rajul sat 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.

Rujul Zaparde
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. They don't have the experience. 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 cut from the DNA of the company and high potential, but maybe isn't like taking a playbook from somewhere else and cutting and pasting it into your company. There'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 the organization. The other thing we try to do is have a lot of brainstorms.

Harry Stebbings
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, right? 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.

Rujul Zaparde
What I found work out is like, all right, everybody takes 15 minutes and write all your ideas out one 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 that we.

Harry Stebbings
Saw 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?

Rujul Zaparde
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 marketing and growth and, like, content marketing. Like, all these different things. Like, I actually think, like, having marketing be quite unfocused is actually okay in its execution. Messaging needs to be focused, but 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 a decision you made with speed that with hindsight should have taken more time and should have had more consideration or thought put into it. Oh, that's a really tough question. I asked someone the other day, and they said, marriage?

Harry Stebbings
I said, you are fucked. That's so funny. Actually. I'll give you a great example. So zip is my second company.

Rujul Zaparde
So my first company was a company called Flightcar TLDR. We would give you free airport parking by renting out your car to somebody else, fully insured. And I dropped out of cost to the company. And I remember I called my friend at the time, say, hey, you know, we're both bored. Like, are you down?

Like, why don't we do a company? And he was like, sure. And I remember I grew up in New Jersey, and so, of course, you know, New Jersey sort of at the time, at least, you know, you would go to panera bread. Like, that's where you would go hang out. And so, you know, 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 in that hour, this was in 2012, I think he was telling me, he's like, hey, there's this thing called Airbnb. And, you know, people are sharing their houses with each other.

We're like, really? Like, I never heard of that. And then we sort of one thing led to another. We're like, well, would they do it with their cars? And if they're going to do it with their cars, maybe they do it at the airport, because by definition, traveling, they're not using their car.

And so that was the idea that we came up with in that 1 hour. We did it for five years. Literally. I would never do that again. Like, we took exactly the opposite approach when we started to zip.

But, like, I mean, that's like, once you pick your idea and you're, like, working on, I mean, you're like, of course you can change, right? We didn't then. You're. I mean, you're just so deep in. So that was one, like, if you're going to do a company, don't time box yourself to 1 hour.

Harry Stebbings
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 and dropping them off at the airport. Right?

Rujul Zaparde
I learned so much in terms of, like, what it takes to be an operational business. And boy, is it. I mean, is it easy to run a P two B SaaS company. We have our problems, but, like, it's not like we're constantly going to be running out of money. You don't have to worry about any of these things.

You don't have 24 7365 subordinated with emergency situations. 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 flight car. It's just a really hard business to work with all the different aspects that need to come into play together for it to work, for that margin to drop to the bottom line.

Harry Stebbings
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.

Rujul Zaparde
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.

And that was that. That was the business. That was the business. Were there any other big lessons from that business? I mean, so many things, man.

But one was do a B, two B 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 understanding the hiring and the talent bar was something that working at Airbnb later on, I think really personally helped me with, which is something that I didn't have back then. I 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're terrified that first time founders won't come to us. But I don't like first time founders.

Harry Stebbings
Like, I like serial entrepreneurs. 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. Serial entrepreneurs? You've just made the mistakes? Or are you like, no, there's beauty and naivety in youth, in upside thinking.

Rujul Zaparde
For me, as a second time founder, I was very, very determined. Lou and I both were, to work on a company, work on an idea that had high execution risk, low fundamental market risk, and sort of 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. 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 risk. Right. Like, the whole thing. And, like, I'm not sure someone would do that as a second time founder, but it's obviously a wildly successful company. And so, like, you can have outcomes like that, but, like, you almost can't have as a second time, maybe because you're just too jaded about the world or too burned.

Harry Stebbings
I'm gonna go there even though I thought that I wouldn't. You said, number one lesson was do b two b. I had trey on from founders fund, and he said serial entrepreneurs in SaaS 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 b two b enterprise SaaS that is not serving the world. What do you say to that? Well, I would say it's.

Rujul Zaparde
It's a little bit different than selling tequila. And I actually would say that if you take what we work on at zip and procurement, I mean, there's eleven times as much money that moves hands between businesses than moves hands between consumer and a 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, I mean, this, of course, takes many steps, but that does carry over to consumers. My second question to you is, I spoke to Adi Rao Ghani, and he said to me to double click on what you just said there, which is the lessons learned from Airbnb.

Harry Stebbings
What were some of 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, CEO of 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 spacing is off just on our mobile app or just like, really, really focus on detail. And what that does is, of course, do those extra, you know, I don't know, ten pixels of white space in and of themselves matter.

Rujul Zaparde
No, but they matter a ton in terms of what that says to the company, you know, and where the bar is for quality of the product. Just like speed. Right. I think, I mean, product quality, design bar, like, all of that. Also, I think, ultimately is a cultural thing and it comes from the founders.

Harry Stebbings
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. 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. That 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 deliberately not selective in what you micromanage? 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.

Rujul Zaparde
Everything from gong call, listening to, 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? Like, can we take something that they're doing really double clicking on that and not, not trying to manage the go to market organization by metrics at long, because it's, it's so hard to, like, actually affect change that way. That's probably the number one. And which one are you?

Harry Stebbings
Like, fuck it. I'm happy to not micromanage that. I can clearly delegate that. And it's not a, it's not a problem. You know, my job, I think, in many ways, is to focus on what's not working.

Rujul Zaparde
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 it's, there's some smoke there. You kind of let it, let it go. What's not working right now?

Oh, I mean, there are always things not 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 cold call people, to email them, to send the messages on LinkedIn, get interest. And how do you sort of scale that team, maintain productivity and allow that team to have a great career path into the AE wall, which is something we're really proud of. How much of net new client acquisition is from that team.

Harry Stebbings
Today we're largely an outbound business, largely in outbound 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 is, given how topped out it is, is actually quite, quite outbound. And it will shift over time for us too. And I can already inbound this at a larger percentage than it's ever been in the history of the company, but the majority is still out, especially after we go after different industries into the enterprise, so forth.

Rujul Zaparde
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 clean data. I find on titles within companies, what is one thing in one company is another thing in another company.

Harry Stebbings
And actually, buyers are very differently placed according to different companies. Do you see what I mean? It's not like great them. No, completely agree. And especially when you sort of add to that different geos, different countries, it just gets even more complicated.

Rujul Zaparde
Very hard to tell. We may be getting too into weeds, but I'm just interested scaling the outbound side. I am just like, I think AI will actually destroy outbound in many cases because it would 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, although look, maybe in 20 years, like, who the hell those? But I do think there's an opportunity to increase the leverage of the team and we're trying out a bunch of stuff using chat GPT, I mean, there's just so much manual work that goes on that you can actually start to automate even. I mean, we'll see. I'll probably have a better read in six months or a year in terms. Of, like, giving the team that trajectory you mentioned from, like, BD and outbound to AE's and, you know, other parts of the sales function, it's really hard to motivate teams when they're not together physically.

Harry Stebbings
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. It's such a tough thing, especially for companies like ours that were born right in the heart of the pandemic.

Rujul Zaparde
And it's challenging because it varies by function. And one of the things we do is for engineering, product and design, we mandate two days a week, specific days, Mondays and Thursdays in the office. That actually was born from. You know, what we found was that it was actually. I mean, a lot of engineering is like, a maker's job, right, at 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 folks is 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. And we decided.

And then they were drowning in meetings, of course. And so what we decided to do is prioritize the in office days and then try to push all the meetings to happen at the 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, actually. I still have mine.

It's right there. And we would keep a Zoom meeting going the entire day because we're in different locations during the pandemic. So for 1214 hours, 16 hours a day, we just had just a Zoom meeting. Then 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. And 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 was just me doing sales. And so whenever I was doing sales, any sales call, I would leave myself unmuted.

So even if you were an engineer at Zip really early. You would be listening to every single sales call. There's only one happening at one time because it was just one of me. And so you'd 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. Can ask what been your biggest hiring mistakes? You learned 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? The number one thing is, like, over indexing on someone that's done it before at like, a similar level of scale.

Right? Like, I think, I think for, even for a lot of investors, I think it's like, people love the, like, press release hire, oh, this person did it. You know, they took them. They did this and they took it from, you know, 100 to 250 of ARR, whatever it is. And so, like, we should just get them and plug them in here and, like, it would be perfect fit and, like, similar, you know, sales cycle or whatever.

Like, I'm not saying that can't work. It totally can. But you incur a lot of risk because it also, I mean, every business is very different. Every situation is extremely different. Like, the same playbook certainly won't work.

It's just like, 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 they have a lot of potential to just get. Get one level above and you have an honest conversation about, look, you're going to 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 much more often than people realize. And you never get recognized for it.

Harry Stebbings
How quickly do you know about hire? Oh, that's a tough question. We've been slow in the past, or you always feel like you could have been faster? Look, I think the way I see it, like, 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.

Rujul Zaparde
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 I trust, that I know are great, and trying to maintain a close dialogue with people like that so that they can temperature check right. It doesn't mean that they're always right. Certainly not the case.

There's always, like, gray areas and a lot of nuance. 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, like, give you just better signal earlier? I always remember Matt Slavechin 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.

Harry Stebbings
I don't know if that's true. I think that's probably true eight out of ten times. And the challenge is that it's probably not true two out of ten 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 review too late or the performance plan. I assume that's what you meant.

Rujul Zaparde
Too late. You're not giving the person an opportunity to, like, like, you haven't, like, detected it early enough, I guess, and given them an opportunity to course correct earlier. Did you worry about raising too much money too quickly? So if this were my first company, I 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 hire too much too early before they, like. No, without that doubt that they have, like, clear product market fit. I think that's so important, though. Like, to really keep a small team, because at that point in time, because, say, the thing isn't 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.

We 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 know the other 19 of you and you just sold them. You were like, oh, this is awesome company.

Like, it's great, and like, blah, blah, blah. You know, if you're at that point in time, you can't be like, actually, I was. I was just wrong. Even though that was two weeks ago. Right?

Because, of course, you have that in your head. Like, yeah, maybe this isn't the right one. We'll figure it out, but maybe it's not the right one early on. And so, you know, we certainly raised a lot of money then. And then later, obviously, well, past we past that point, but we were very disciplined.

Like, no matter what money we had in the bank, we were not going to hire more. I mean, there was a point where we were a small company and cash flow positive because we had just held back hiring so much. And then we really unlocked the gates when we felt like we had confidence. Price wise, investors will pay up for assets that are great with great founders like you and Lou. Were you worried about the price bluntly, just being very, very high in such a short space of time?

Harry Stebbings
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, we were just so. Confident that there's so much market need and the growth rate that we had and have, it was more just an opportunity to do something that we maybe would have done a little bit later and just do it now.

Rujul Zaparde
That's how I thought about it. We had that confidence, and we have the confidence now. Raju, you're constantly speaking to people, investors, employees, customers. What question do you not get asked that you should get asked more, huh? That's a really.

That's a tough question. Do you see yourself running zip in 20 years time? Yeah, absolutely. We wanted to start a company that was going to be a generational company at the time. This was 2020.

When we started the 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 know, so many of the best, and this is their life's work. This is the only thing they focus on.

Harry Stebbings
And that is such a big sign for me. I mean, not once have I ever thought of something after, like, there is no after, like, there's no. Listen, I want to dive into a quick fire round. So I say a short statement, you give me your immediate thoughts. Does that sound okay?

Rujul Zaparde
Okay. Okay. So what have you changed your mind on most in the last twelve months? I think it's probably my, like how I manage my day to day. So there was a, there was a point early on when we had like a huge spreadsheet and every single person in the company would just literally write out their todos for the day in each tab in the spreadsheet.

Obviously that broke after like 1015 people. My current thing is I have a note card and I actually write out what I'm going to do for the day on the note card goes in my pocket and I cross it out and then I throw it out and then I have a fresh one tomorrow. What are you most concerned about in the world today? Well, this might be trite. I mean, we've got, you know, a lot of tracks of work obviously going on around generative AI, and I'm not going to open up a whole can of worms, but you just read such concerning headlines in the news about things that can happen, things that we're now going to be able to do, that you sort of wonder, where does that leave us even just a handful of.

Harry Stebbings
Years, does that worry? I take the view that bluntly, we always overestimate adoption in a year and underestimate it in ten years. And I think it's like, oh, everyone's going to have no jobs. And all of the gross over dramatizations, like 94% of european corporates don't know what notion is. No, no, I actually, I agree with you.

Rujul Zaparde
Like I think adoption in the enterprise, all of that will be slow. No, I think what actually concerns me, just like adoption for like malicious intent, like can 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 pretty quick. What do you think of the biggest ways VC's and founders are misaligned?

It's like the time horizon, maybe how much the outcome matters. Ultimately for an investor, this is one of whatever number of portfolio companies they have. Of course, the dynamics are such that only one, maybe multiple, if they're lucky, will return the fund or whatever, and they don't need every single one to work. And as a founder, this is your life. Just fundamentally there's got to be some level of misalignment again, it's not like an incorrect intention.

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 Slupman.

I'm a huge Frank Slipman fan. And read amp it 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?

I think hiring to solve problems. So many companies like, oh, you have this problem, great hire. And it's like, whoa, 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 impacted 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 it can be. When Lou and I 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 in the 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 alone.

I mean, it can just be so complicated. Why do you wish you'd known that? Because when you think about though, I wish I'd known this because then I would have done this differently. So if we start, if I give a minor, 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 then 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, we have a platform today, but to build out more of a platform without having to expend a lot more resources that we've had to, to, as of the last six, eight months. To be fair. To be fair, maybe the answer is actually no, we wouldn't have done that because it would have just taken more time and we wouldn't, like, have put in the engineering sources because it wasn't the right thing to do at the time. I could see the alternative, too.

Harry Stebbings
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? Yeah, yeah. You have limited information. You do the best that you can with it.

Okay, so we're 2040 through 420, 44. What is zip then? And where are you in 2044? Well, I sure as hell I'm still here thinking about procurement at Zip. You know where I think, where I think we can be as a product, if you think about it, right, think about the notion of an approval significantly over 90%, even over 95% of the time, people are approving things.

Rujul Zaparde
Like, if there's an approval they're approving, you bet they're approving it. 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, you know, 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 that process, can you just not need to do approvals because the software can do it for you?

We're not there today, but there's definitely a world, I mean, and hopefully a lot sooner than 2044, where you can say no, actually, like, right? Like, you don't need to have a human go in there, review the thing, and then approve it in 20 years. I think people would be like, really? You had humans, like, reading these documents, like, thinking about them and then approving them? That seems dumb.

Harry Stebbings
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 serve zero point. Thank you so much for joining me, Russell. This has been such a fascinating and varying discussion, but you've been fantastic. No, thank you so much for having me.

I just love shows like that. I always started 20 VC 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 Rajul 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 20 VC.

Thats 20 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 VC's, they help VC's 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.

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Well, Navan is so confident youll move to their game changing all in one travel, corporate card and expense super app that they'll give you $250 in personal travel credit just for taking a quick demo. Check them out now@navan.com. 20 VC 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.

What's blown me away is the Squarespace blueprint AI and SEO tools. Its 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 customers needs, making transactions smooth and hassle free. And the squarespace AI? Its a content wizard helping you whip up text that truly resonates with your brand voice.

So if youre ready to get started, head to squarespace.com for a free trial. And when youre ready to launch, go to squarespace.com 20 Vc and use the code Twentyvc to save 10% off your first purchase of a website or domain. As always, I so appreciate all your support and stay tuned for an incredible episode of 20 growth on Friday with the one and only atom growth, one of the masters of growth from Heroku, from Salesforce, from Dropbox. That one is not to be missed.

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

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1: Introduction to Rujul Zaparde and Zip

2: Importance of Speed and Innovative Hiring

3: Lessons from Scaling

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