20VC: Raising $60M and Not Touching a Dollar of It; The 3 Decisions That Led to a Cash-Flow Positive Business, Why Not Being Able To Fundraise in the Early Days Can Help Build Your Business & What are the First Things To Break in Scaling Orgs with Sameer

Sameer Shariff is the Co-Founder and CEO @ Cambly, the company that allows you to become fluent faster through one-on-one video chat lessons with native English tutors. To date, Sameer has raised over $60M with Cambly from the best including Jeremy Levine @ Bessemer, Sarah Tavel @ Benchmark, Monashees, YC and more. Prior to founding Cambly, Sameer spent close to 5 years at Google on the Search Quality team and became the Tech Lead of the Search experiments team helping make experimentation a core part of the launch process. In Today's Episode with Sameer Sharif We Discuss: 1.) Entry into Startups and Co-Founding Cambly: How did Sameer make his way into the world of tech with his joining Google straight out of college? What were the 1-2 biggest takeaways from his time at Google? How did it shape his mindset? What was the a-ha moment for Sameer with Cambly? 2.) The Trials and Tribulations of Leadership: What does "high performance" mean to Sameer in business? How has it changed over time? What are the first things to break in a scaling company? How do the best companies retain speed and agility with scale? What are the single biggest hiring mistakes Sameer has made? What did he learn? 3.) The Fundraise that Led to Cash Flow Positive: Why does Sameer think it was so hard to fundraise for Cambly in the early days? When they failed to raise their Series A, what 3-4 core decisions did they make to get Cambly to cash flow positive as fast as possible? How did Sameer communicate their failed fundraising to the team? How did he do this in a way that rallied the troops and did not worry or scare them? What was the tipping point for fundraising to become much much easier for the company? Given they have not touched any of their Series A or Series B funds, how does Sameer think about the balance of growth vs profitability? 4.) Marketplace Dynamics 101: How did Cambly acquire the first 100 customers on the demand side? What is the most challenging dynamic of Cambly; demand or supply side? Where does Sameer see most marketplace founders make the biggest mistakes? What does Sameer know now on the intricacies of marketplace dynamics that he wishes he had known at the beginning? Items Mentioned In Today's Episode with Sameer Shariff: Sameer's Favourite Book: The Most Human Human: What Artificial Intelligence Teaches Us about Being Alive

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  Welcome to 20 VC with me, Harry Stebbings. And today we tell an incredible story, the story of a company that has killed it. But unlike the majority, they've not done it in the spotlight. They've raised from the best in the business, but due to their business being so good, they haven't even touched the money that they've raised. It's an exceptional story, and I'm so excited to welcome Samir Sharif, founder and CEO at Cambly, the company that allows you to become fluent faster through one-on-one video chat lessons with native English tutors. To date, Samir has raised over $60 million with Cambly from some of the best, including Jeremy Levine at Bessemer, Sarah Tavel at Benchmark, the team at Monarchies, Y C, and more. Prior to founding Cambly, Samir spent close to five years at Google on the search quality team and became the tech lead of the search experiments team.

• 0:42Harry Stebbings?

  I'd also want to say a huge thank you to Sarah Tavel, Jeremy Levine, Samir's co-founder Kevin, Eric at Monarchies, Gustav at Y C, Samir's wife Heber, for some amazing question suggestions today. Such a team effort there. But before we dive into the show today, I want to talk about an incredible tool that I use every single day, Notion. Now, I am the worst for having 50 tabs open and constantly hopping between an endless array of tools. Do you feel me? Are you with me? Well, then Notion came into my life, providing one tool to do it all, with everything from seamless project management to easily organizing 20 VC's company information. A fascinating standout on Notion usage, more than 70% of companies who start using Notion stop using two plus other tools. And so Notion can even save you money, given how many other tools it can displace.

• 1:26Harry Stebbings?

  Notion has a worldwide network of millions of users, creating templates, tutorials, and new inspiration. The product's getting better and better every single day, and you always have the support you need. Learn more and get started for free at notion.soh. Take the first step toward an organized, happy team today, again at notion.soh. And speaking of foundational infrastructure like Notion there, Angel List has been a key partner for me in managing my investments. I just love using the Angel List platform because it abstracts away all the complexity and operational burden of fund management. Whether you're running SPVs, a traditional venture fund like me, or a rolling fund, Angel List has you covered. I'm also super excited about their new product, Angel List Stack, which is purpose-built for founders. With Angel List Stack, you can create a fundraising-ready Start up in just a few clicks.

• 2:11Harry Stebbings?

  Angel List handles your company's incorporation, banking, cap table and fundraising process all in one single place. And this allows founders to focus on building. If you're a founder, you can launch your company at stack.angellist.com/20vc. Whether you are a founder or a funder, you're in great hands with Angel List. And finally, from websites and online stores to marketing tools and analytics. Squarespace is the all in one platform to build a beautiful online presence and run your business. There are three things for me that I just love about Squarespace. First, mobile optimized websites. All websites are optimized for mobile. Content automatically adjusts, so it just is really beautiful on any device. Second, email campaigns.

• 2:52Harry Stebbings?

  Squarespace makes it super easy to grow and engage your audience with Squarespace email campaigns. Say what, no other provider needed? Amazing news. Finally, SEO tools. Squarespace takes the guesswork out of SEO, so you'll get found in search by more people more often. And if that wasn't good enough, go to Squarespace.com/20vc for a free trial. And when you're ready to launch, use the offer code 20vc to save 10% off your first purchase of a website or a domain. But without further ado, I'm so excited to hand over to Samir Sharif, founder and CEO at Cambly.

• 3:30Speaker 01

  You have now arrived at your destination.

• 3:33Harry Stebbings?

  Samir, this is such a joy to do. I've heard so many great things from Jeremy, from Sarah, even from your wonderful wife. I really did my research clearly, but thank you so much for joining me, Stacey, Samir.

• 3:43Speaker 02

  Thanks for having me. I'm a huge fan of the show, so I'm honoured to be here.

• 3:46Harry Stebbings?

  That is very, very kind of you. I'm thrilled that you like the show. But I do want to start with a little bit on you. We see Cambly today now becoming more and more public. I'd just love to go back to the beginning. What was the founding moment for you with Cambly? And when was that realisation that this was a core pain point that we had to solve?

• 4:01Speaker 02

  Yeah, definitely. So Cambly grew out of our own experiences, learning languages. My co-founder and I both grew up here in the US and we went to the public school system here, took foreign languages as part of that process. And for me personally, I studied Spanish and I never really felt like I was very good at it. Thought I wasn't really a languages person. And then independent from that, I love Love to travel. I've been all over the world and I've been to many places where everyone speaks Spanish. And I found that to just be such a better environment for learning a language. And I took one trip to Argentina in particular that for a good chunk of it, I was traveling on my own. And I kept finding myself in environments where I was surrounded by people that only spoke Spanish. It really took like a situation like that for me to really come out of my shell and and practice speaking.

• 4:43Speaker 02

  And what I found is I got so much better at the language so much more quickly than I ever did in a classroom environment. And not just that, it was also just far more rewarding. Thing I love about travel is getting to meet people and learn about their lives and I was getting to do that. And we kind of got together on this idea like, why can't we practice these languages whenever we want? There's plenty of people that speak those languages. They just don't happen to live near us. We felt like, hey, this sounds like the kind of problem that technology could solve. And what the two of us wanted wasn't necessarily a professional teacher or a formal lesson. What we wanted was a friendly person to practice with. So that's kind of what we set out to build. As we looked at the market, we quickly realized that the world wants to learn English, so we decided to focus on that.

• 5:21Harry Stebbings?

  I love that and I love the focus purely on English. We'll dive into the focus. I do just want to touch on one background element. I always think that we're shaped a lot by our past experiences. And you obviously spent, you know, four years or close to four years at Google. I'm just fascinated. How did seeing the internal mechanics of Google, being there for four years? How did that shape your operating mindset and how you are as a leader today with Cambly?

• 5:41Speaker 02

  So I was really fortunate to get a job at Google straight out of college. Learned things like how to build a great software and to do it at scale, which has served me really well. I was on like kind of a metrics and analytics team. And so I learned a lot about metrics and data. I learned a lot about how Google thinks about and approaches data. I think that helped me understand how to make kind of the importance of data-driven decision-making. Google has immense amounts of data and I think they really appreciate the scale of data and how sometimes scale of data can win. And I think they just rely a lot on data for decision-making. So you might have an intuition, I might have an intuition, they might both be totally wrong. And the team I worked on, we ran A B tests on everything. So you just learn a ton from actually putting stuff out there and running a split test on it and measuring what the impact is.

• 6:24Speaker 02

  And that's something that actually works obviously really well at a company like Google at huge, huge scale. But actually you can employ a lot of Those same strategies at a startup in order to kind of hill climb your way to a better growth engine.

• 6:34Harry Stebbings?

  How do you know when to listen to data and be scientific and rigorous in your approach versus when to go on gut and intuition?

• 6:41Speaker 02

  It's a really good question. I mentioned some of these things apply really well to startups, but the reality is in the very early days of startups, you don't really have much data. In theory, you might think, oh, let me just A B test everything and A B test my way to success. And it doesn't really work because you're tiny, there is no data and you kind of have to deeply understand the problem, largely go off intuition. As your company kind of starts to scale, you can then start to layer in these experiments. I remember in the early days of Cambly thinking, oh, man, I know of all these strategies and tactics and they just don't work at all because we're just too small. We ran a test, I think, in the really early days where we cut our prices in half. And I was like, let me try to measure like the price sensitivity of Cambly. And we were getting like a purchase a day or something. You can't measure anything at that point.

• 7:24Speaker 02

  And so I think I'd have had to sort of tuck away these techniques I knew and understood really well and say, this will serve me at some point down the road, but not now.

• 7:32Harry Stebbings?

  That is hilarious. Two purchases in a day and then you realise one's your wife and you're like, oh, that was not a successful task.

• 7:38Speaker 02

  Exactly, exactly.

• 7:39Harry Stebbings?

  And we're going to go through the different elements of the business. Bluntly, you've got now Basma, who did the A, Benchmark, who did the B, Jeremy and Sarah, amazing investors, some of the best you could have got in the world. But it wasn't always smooth sailing in the fundraising markets, I heard. Why do you think in your mind you struggled fundraising in the early days?

• 7:57Speaker 02

  Yeah, I think a couple of reasons. I think one of the really big ones is, well, for starters, camp is kind of a weird business in a bunch of ways. And I think one of the ways it's strange is we were two Americans living in San Francisco, building an English education app that was meant for basically everyone who was not here. We were not building the product for ourselves and all of our customers were like everywhere else. The way that translates to fundraising is you go to talk to an investor and you're solving a problem that they've never had themselves before. They probably haven't thought about that much. It's this immense problem in the world, but it's not a problem we see every day. There's about seven point five, eight billion people in the world, six billion of them don't know English. Of those six billion, one point five billion are actively trying to learn it right now. This is an.

• 8:40Speaker 02

  Enormous problem, but you and I, we speak English already and We've always spoken English. It's just not a problem we've ever faced in our lives. So it's enormous problem in the world that we just don't see at all. And the same is true for investors. And so I think that made it challenging to kind of convince people that, hey, this is a really worthwhile and important problem to solve. I think another reason is there've been a handful of companies that have tried to tackle language learning before us and struggled. The net effect, kind of the combo of those two factors, meant that we just had to hit bigger milestones than sort of an equivalent company in order to get that fundraise done. We had to kind of prove more.

• 9:13Harry Stebbings?

  Can I be so rude and say, when I hear language learning and ad tech apps in this way, and again, you can hate me for this, but try and delay your hate until after the episode. I'm literally like, oh no. High churn, like the retention is always brutal, is low ticket prices. It's just like, oh, don't do it. No one's done it. Don't do it. That's just Samir. I'll give you money to do something else.

• 9:37Speaker 02

  This is exactly, by the way, why it was hard to fundraise, because you're not alone in that feeling.

• 9:41Harry Stebbings?

  But why am I wrong? Why? I'm sorry, but and again, I'm going off school here. Every education app has shit retention. Why is Cambly different?

• 9:49Speaker 02

  Yeah, retention, I think, is maybe the most important metric in a business. Super, super important to look at and pay attention to and make sure you're optimizing for it. I think if you look at education technology, like a lot of the services that exist are either pure software services, where you can kind of quit whenever you want, or a giant classroom, like massive online course, where also you can quit whenever you want and no one cares. Cambly is quite different from that. Cambly is a one-on-one conversation, not too dissimilar to this one. And I think because of that, it's inherently just like much more engaging. It's like this human-to-human connection. You build relationships. You actually like, our students get to know our tutors really well. And yeah, there's, there's strong relationships that are built there. In the same way, you wouldn't

• 10:32Speaker 02

  set up a dinner with your friend and then just stand them up. You kind of feel like you've got some obligation to show up to your class on Cambly. So I think there's a social component and I think it's just a lot more fun and engaging to sort of really exercise the skill of speaking English by practicing in these one-on-one conversations. I think that's a big part of why Cambly looks And feel so different from your average education technology company.

• 10:53Harry Stebbings?

  Retention is a wonderful focus and north star, but it's so much more nuanced than that. How do you define a retained user? What is the action? What is the behaviour process that would consider a retained user for you?

• 11:06Speaker 02

  Yeah, so our North Star metric from the pretty early days was paid usage. So the amount of minutes that students spend actually using the product. And every minute there is a tutor teaching and a student learning. And what I love about that metric is it's a value delivered metric. That may seem obvious as I describe it to you, but actually I think a lot of the companies that came before us optimize much more for revenue. The challenge with that is you can sell the dream for a product people don't actually use and make a lot of money in the process. A lot of those companies would charge a lot of money upfront for it. And it can be really misleading because you might feel like your business is doing really well. But unless you're actually delivering on the value that your customer wanted, you're heading down a really bad path. Totally unsustainable and eventually will catch up to you.

• 11:48Speaker 02

  And very early on, in the first year of us working, we kind of saw that this was a pattern of language learning companies. And we've sort of vowed not to become one of those companies. One of the best things we did towards that was picking the right North Star metric. Like this is all about usage. We want people to not just pay for the thing, but actually use it. And as a result of that, I think we've been able to make a number of really good decisions along the way. That has helped us drive long-term sustainable growth.

• 12:10Harry Stebbings?

  Can I ask you, we mentioned that like the struggles of fundraising in the early days, but you said actually there is value in tough fundraisers in the early days. And having that experience, what do you think the value is of not being able to raise early on somewhere?

• 12:23Speaker 02

  I think when you don't have a lot of resources, you just have to work with what you have. You learn to be really scrappy, really efficient. A lot of those decisions you make without a lot of capital helped us build a product in a marketplace that was highly, highly efficient. And then as we scaled it, we were really, really capital efficient in the process. So I can give actually a concrete example, like we went out to raise our series A and it was a challenge, like it did not go as planned. We had to basically pull the team together and say like, hey, we were planning on raising an A, it's not going to happen. We're going to start executing on plan B. And plan B was actually to get the company the cash flow. We made a number of really good decisions in a very short period of time that four months later led to the company getting into cash flow positive and we've been cash flow positive

• 13:08Speaker 02

  ever since. As you can imagine, that has served us super, super well. If for one thing, made fundraising a lot easier when we went back out a little time later, the conversation was very, very different.

• 13:18Harry Stebbings?

  First, what were some of the, you said about the decisions you made. What were those three or four decisions that really moved the needle?

• 13:24Speaker 02

  Yeah, so one nice thing about Cambly is it's a marketplace, it's a two-sided marketplace, students on one side, tutors on the other. From basically day one, we charged for the product. We had a business model that made revenue from day one. There's a lot of leverage in pricing. One of the things we did in that period was change our pricing, basically, and made sure that we had all this money flowing through the system. We wanted to make sure we were taking a healthy margin from it and that could sort of slipped over over time. And so pricing was a huge one. We also offer students like a number of plans and if they want to commit for a longer period of time, then they can pay upfront for that. So that has really healthy cash flow dynamics for the business. I think throughout our history, we've just kept a really, really lean team. And so we've done a lot with like a really small team. And that wasn't necessarily a decision that we that we made kind of in

• 14:09Speaker 02

  the moment when we were kind of in that period, trying to figure out how to get the company cash flow positive. But it was a decision that sort of we continually made in the early days, including like me and my co-founder, wearing a lot of different hats and and serving a lot of different roles for the company.

• 14:21Harry Stebbings?

  Do you want to ask, as a VC, and this is sounds ridiculous in 2022, but as a VC today, I'd be going cash flow positive, well, not today, last year, cash flow positive, like you've raised all this money now. And I spoke to Jeremy, he told me you haven't touched a dollar of your series A or your series B. You're not optimizing for growth is kind of what one would take away from this. How do you feel about that growth versus profitability now? And now you have the leverage. Is now not the time to spend?

• 14:46Speaker 02

  Yeah. So I guess the one thing I'll call out is just because we haven't touched the series A money and the series B money, it doesn't mean that we sort of behaved exactly the same had we not raised that money. Having that cash cushion, I think, allows us to be much, much more aggressive and make a very different set of decisions. And so I think we've benefited a lot from the cash, even if we haven't touched it, because it's allowed us to plan around that.

• 15:10Speaker 02

  Is I want to grow as fast as humanly possible, but I want to do it in a sustainable and healthy way. I know that the markets kind of change and sometimes that's a trendy thing to say and sometimes it's not. And right now, maybe it's a little trendy, but but you know, we've been doing it for years and years now. And I think to Jeremy Levine's credit, he's a big believer in that as well, no matter what, which way the tide is going. So I believe you want to grow as fast as you can, but do it really really sustainably. One way to think about this is you're not growing just to like hit a milestone, then do the next fundraise. Like, that's not how I think about it. How I think about it is I want to figure out the mechanisms that will allow me to grow for a very long time. So if you think about those early days, I'm experimenting, like I'm figuring out what are the things that work. And if you're blowing through a lot of cash and doing unsustainable things, there's a really good chance you're learning the wrong lessons.

• 15:55Speaker 02

  And they're not necessarily going to serve you down the road. And so we've always tried to grow in a really sustainable way. And I think if you look at the right time horizon, you look at, hey, I want to figure out how I'm going to scale this company over the next 10 or 20 years. We're in this experimentation stage. We're figuring out the things that will allow us to do that and we're making those investments. So I think that's like a framing that I think will make you maybe less inclined to sort of burn a hole in your cash. Because you might have the wrong takeaways from that.

• 16:22Harry Stebbings?

  How do you advise founders when it comes to capital efficiency? When it comes to fundraising, growth, spend, given your experience and perspective?

• 16:30Speaker 02

  I'm a big fan of being really lean and being really capital efficient in the early days. Figuring out how to get, just really focusing on the core business and making it really strong and healthy and getting that early traction. And plotting a path for the business to be able to stand on its own two feet. It just gives you so much optionality. And again, from my personal experience, when I've not done that, it's been hard. Wasn't always easy to predict either. I thought, hey, the company's doing pretty well, we're a great team, we should be able to do this next fundraise. And then I've regretted, I think, maybe that unchecked optimism. And so I often try to try to balance out founders who I think maybe come in with similar sort of unbridled optimism. But hey, here's what some of the realities might look like. This might play out this way, just make sure you're not putting all your eggs in one basket.

• 17:14Speaker 02

  That's kind of often the tone I take when I'm advising folks, specifically around like an upcoming fundraise.

• 17:20Harry Stebbings?

  Mentioned like how you think about growth and sustainable growth. I want to talk about you and the different hats that you wear within the companies. Because whenever I spoke to anyone, they all spoke about your skill here and to dig in here. And so I wanted to start on performance. How do you define high performance in business today as a leader?

• 17:36Speaker 02

  I think about performance as focus, results and driving for impact. And I think in the early days, I used to think of that kind of, I think, very much at the individual level. What are you personally doing to kind of drive an impact in the business? And then obviously as the organisation has scaled, I think I've, I've really grown to appreciate what great leadership looks like. And then the type of leverage that has on the business. How do you create an organisation and an environment that drives towards impact? And I think one of the things I've been, I've been thinking about even more recently is we've got a much larger company now. Like, how do you get everyone across the company aligned and running in the same direction? So my definition of high performance, I think, has evolved over time. But it started off with sort of individually, what are you doing? How much are you driving for results and impact?

• 18:17Speaker 02

  And then it's kind of grown and evolved into how you get your organisation or whoever's under your purview driving in the right direction. And everyone on your team pushing towards impact.

• 18:25Harry Stebbings?

  I always think we learn as a leader from tough times and mistakes that we've made or tough times we've experienced. When you think back through the Cambly journey, and this is a really hard one to throw on you, so forgive me. But I want to ask, when you think back through that journey, what was the most painful experience that you've had? That's also been very good for you as a leader to have had and you're pleased to have gone through.

• 18:47Speaker 02

  So I'd have to go back to that same one that I kind of touched on when we went to go out and raise our series A. And it did not go as planned. I mentioned Cambly's cash flow positive today and has been for the last five years. That was not our choice. We didn't say, hey, today we're going to become cash flow positive. We became cash flow positive out of necessity initially. We had some amount of money in the bank, but we were burning a decent amount and we went out to raise and it didn't happen. So we had this moment where we're like, okay, this is, it was the first and only time in our history where we had an existential risk. And that's stressful, but it also brings a lot of clarity in terms of what you need to focus on. And what me and my co-founder noticed, I think, as we kind of started executing on plan B and figuring out how are we going to plot a path to cash flow positive for the business. What we noticed is that the rest of the

• 19:30Speaker 02

  Company was kind of continuing to do the things that they were doing and they were good things. But we were, I think, coming in and saying, hey, just stop doing that, do this other thing instead. And I think what we realized is it probably seemed kind of arbitrary. Why are Kevin Smear saying like, stop doing this and work on this instead? And what we realized is they were just missing really, really important context. They were trying to grow the business and thinking years out. And we were trying to stay alive, like we were trying to keep the company from running out of cash. So when we had this realization, what we decided to do, and again, this is very scary at the time. But I think it was a really good growth moment for me and something I learned a ton from is we decided to pull the whole company together and say, here's what happened. We told them we were raising a series A, it didn't happen.

• 20:08Harry Stebbings?

  Were you worried about them losing faith, losing morale, going, oh, God, Cambly is not the rocket ship that I thought it was, I'm gonna move? That's a dangerous move. Were you worried in that moment? And how do you think you did it?

• 20:20Speaker 02

  I was absolutely worried in that moment and I think inherently a very scary thing to do. And I can't say that I was like, this is definitely the right decision immediately. I had to kind of work through it, but and work up enough courage to do that. But ultimately, I think we decided in order for us to figure out how to get out of this predicament. We need the team to help us. There's no other way to do it. I think there was a fair amount of trust and faith that, hey, we've got a group of people that will pull through for us. And I think what helped was we told them, here's the update, the fundraise is not happening. Here's what we need to do as a company. And I think it was helpful that we had a plan. We didn't just say, okay, things didn't go according to plan. Any ideas, anybody? We came in and we said, here's what our plan is. And not just that, we'd actually started executing on it through some of the things I mentioned, some of the price changes, increasing our margin.

• 21:02Speaker 02

  And so we didn't just have a plan, but then we showed a graph of, and here's what our gross profit was two months ago. Here's what it looks like today, we're actually on the path. So I think it was helpful to, I think, show that, hey, here's a way out of it. And we're on that path, but we need all of your help in order to get there. And I think that level of transparency was, like I said, scary, but I think really, really powerful. And we entered that room with a team that was, I think, pretty misaligned, for lack of a better term. We were just prioritizing different things and we left that room with a team that was very highly aligned. This is what we have to do as a company. And it was incredible. I mean, coming out of that, everybody across the company started working on all of the most important. And things to make sure that we could get the company to a healthy, sustainable, in our case, catchable, positive place.

• 21:45Speaker 02

  And again, a very stressful, challenging time for me as a leader, but something I reflect on. I think the company made a ton of progress in those few months, and I think I grew as a leader a lot. And I look back on that and draw lessons from that all the time.

• 21:57Harry Stebbings?

  Were you a remote team then?

• 21:58Speaker 02

  No, we were in person.

• 21:59Harry Stebbings?

  Would it have been different if you were a remote team, do you think?

• 22:01Speaker 02

  I'm a fan of in-person collaboration, so I always bias a little that way. But I think you can do this stuff remote as well. I think another moment when we had a similar kind of conversation with the team, when probably every company across the world was having this conversation was when the pandemic hit. I looked a lot on the conversations we had during that attempted series A process and tried to say, okay, the best thing to do for the company, for the team, is to bring everyone in and say, here's what's happening. So that one we did over video chat, we did remote. I think it went over really well as well, and I got the team aligned, put everyone at ease. I think it's doable at a remote, but it doesn't hurt if you can all be together in a room.

• 22:36Harry Stebbings?

  I can ask, what was harder to acquire, supply or demand, and has that changed over time?

• 22:42Speaker 02

  We've always been a demand constrained marketplace, so we can grow the marketplace as fast as we can find demand. So there's no shortage of demand at all. This is an enormous problem in the world. It's purely a matter of how do you reach those people in a cost-effective way? And that's been the general bottleneck of our business.

• 22:59Harry Stebbings?

  You mentioned distribution there and just getting to them. I think a lot of distribution is actually consumer resonance and storytelling and product marketing. It was another skill that Kevin and Jeremy actually said you were fantastic with. So how do you think about what makes a truly great story and really effective product marketing today?

• 23:18Speaker 02

  I like storytelling. I find it fun. And I think the way I would dissect that is I think stories about people are just much more interesting than stories about numbers or categories or broader things like that. And so I think it's a lot more compelling to hear about one student on Cambly and their personal journey. It just draws you in a lot more. I also love to share like small details, I think, that that kind of makes people resonate and understand the story. And so that's a personal stylistic preference of mine.

• 23:46Harry Stebbings?

  Leadership is ever-changing. Work gets harder over time. And what gets easier?

• 23:51Speaker 02

  Yeah, so I think like in some ways, running the company can get easier because you hire all these people with a ton of experience and they run actually large parts of your org and you can learn from them. And as the company has scaled and we've been able to bring on some folks like that, we're just, I just don't have to be in the details as much anymore. They know far more about their domains than I do, hand that off and let them run their piece of the company. So I think that gets easier. A lot of stuff gets harder. I think the scale of the problems are just bigger. You've got a much bigger business, you've got much more customers, you've got a bigger team. So everything's just a, everything is just higher stakes. So I think there are a lot of challenges that come from that.

• 24:31Speaker 02

  Scaling your culture can get challenging. I think when you're really, really early on, you have one-on-one relationships with everyone at the company and you can influence that very much personally. But as the organization grows, you have to find ways to scale that and bring on new people and kind of bring them into your culture screen for that. So I think that can be challenging as well.

• 24:48Harry Stebbings?

  What is the first thing to break in a scaling organization?

• 24:51Speaker 02

  The thing you touched on earlier around how do you increase your velocity as you grow the organization? I think that's a really challenging one that can be misleading because it feels like if you add people to your company, of course you'll go faster. But it's not a given that that happens. And I think Kevin and I like had been in organizations where we saw teams grow and then not necessarily move faster as a result of it. How do you make sure that as you add people, your company actually moves much faster? And if it moves slower, that's terrible, right? But even if it's moving the same speed, you've now just become a less efficient company. Figuring out how you can still drive that same level of impact as the organization grows, I think is a real challenge. And I think we're getting much better at it, but it's been a learning curve for me for sure.

• 25:30Harry Stebbings?

  What have been your biggest hiring mistakes?

• 25:32Speaker 02

  Because of the, how unusual Campbell is as a business, we kind of discovered fairly early on that we need to market to all these places that we don't know about. We don't know the language, we don't know the culture. Literally the first hire that Kevin and I made, we were two sort of former Google software engineers. And employee number one was a Korea country manager. So pretty odd makeup of a three-person team. But when you think about the space we're in and the business we're in, where our customers are, it made total sense. What we found was if you could hire the right person, it was a massive on Korea went from being not even really on the map to quickly becoming our biggest market shortly after making that hire. And so obviously a lot of really interesting lessons there. I think one that comes to mind for your question was you could hire a great marketer, for example. But if they have any level of success, they have to then start to build out a team.

• 26:16Speaker 02

  So you want to make sure that they can lead as well. They're a manager and I've made some mistakes there where we've hired some country managers that either were great individual marketers, but had more challenges running a larger team. We've hired some that have struggled with some of the analytical pieces, which we found to be really, really important in that role. But hiring is really hard, like you're going to make mistakes. And I think you just sort of have to be comfortable with that. And when you do, you have to correct it as quickly as you can.

• 26:43Harry Stebbings?

  When you look back, do you have a high tolerance for risk?

• 26:45Speaker 02

  In some ways, yes, and in some ways, no. And I think starting a company like Cambly was leaving a cushy job at Google and deciding to kind of get into startup world was a pretty big risk in itself as well. But I also like to think things through really carefully. I like to think decisions through and make some answers there. I'm open to risk, but I want to really understand what I'm getting into first before I take the leap.

• 27:05Harry Stebbings?

  I do want to move into my favorite though, which is a quick fire round. So you know how this goes. I say a short statement, you give me your immediate thoughts. Does that sound okay?

• 27:12Speaker 02

  Sounds great. Yeah, let's do it.

• 27:13Harry Stebbings?

  Given the fact that I hate reading, you can be the intellectual one. What's your favorite book and why?

• 27:18Speaker 02

  So I'd have to go with a book called The Most Human Human by Brian Christian. The book sort of follows the journey of the author participating in something called the Turing test. And basically the setup is there's a panel of judges and they chat over like an instant messenger type interface. What they don't know is whether they're talking to a chatbot, an AI chatbot or an actual human. And they have to try to guess and figure it out. And they give an award for the chatbot that does the best and fools the most people is the most human computer. And they also give this sort of funny award to the human who convinces the most people that they are in fact human, the most human human. And it's just a fascinating read and it's all about human connection. And as you can imagine, there's lots of parallels to Cambly there, which is also all about one on one interaction and human connection.

• 28:03Speaker 02

  So yeah, I'm a big fan of that one.

• 28:05Harry Stebbings?

  What do you think is your biggest strength and your biggest weakness? If you do thirty seconds on each.

• 28:10Speaker 02

  I think biggest strength is probably giving people a lot of ownership and autonomy. I like actually handing things off and I think the country manager org that I talked about has done really well. A big part of that is because I couldn't do the job. I handed off and I gave people these high level goals and said, okay, go figure it out. And I think I've done a really good job giving people a lot of ownership and autonomy. And I think that's helped kind of build a really good sort of leadership dynamic within the team. I think the weakness is probably, I like to think things through really carefully. But at a startup, you have to kind of trade that off with speed as well. So you have to make decisions with imperfect information. And this is one where I try to counter that by surrounding myself with the right people. My co-founder for one has a very different style than me and we complement each other really well.

• 28:52Speaker 02

  And then I also like to talk to lots of people that can help me think through a decision. And I think it lets me get to the right answer faster.

• 28:59Harry Stebbings?

  What's the hardest element of your role with Cambly today?

• 29:02Speaker 02

  I think probably the, one of the most challenging things is we've got a really global business with a really global team. And running this global workforce really effectively and keep everyone connected to the sort of the central team, I think is, has been a challenge. And I think also as we've scaled, like scaling our culture, we had kind of a really strong culture with a small team early on. And figuring out as we grow the team, as we bring on leaders, how do we preserve aspects of that culture? But also evolve that culture as a business grows.

• 29:30Harry Stebbings?

  Tell me, if you could be CEO of any other company, what company would you choose and why?

• 29:34Speaker 02

  I'd have to go with Airbnb. I think that's a company we've looked up to for a long time. I think it's a really cool company and there are a lot of interesting parallels to Cambly. It's a cross-border marketplace, not too dissimilar from Cambly. It's introducing kind of a new behaviour that people didn't have before, also pretty similar to Cambly. And so I think it's a really interesting company. It's also about connecting with people in other places. So I think it'd be a lot of fun to run that company if I wasn't working on Cambly.

• 29:59Harry Stebbings?

  What do you know now that you wish you'd known at the start of your founding of Cambly?

• 30:03Speaker 02

  I think hiring in like leaders with a really deep expertise in an area. We ran a good chunk of the company for a long time without, we were kind of a team of people that were learning on the job. And I think only more recently have we hired some very senior folks. I think that just allows you to move faster. Because folks like that can draw from the many lessons they've had in their in their very successful careers and inject those things into Cambly. So if I could go back, I'd say, hey, pull in some really strong leaders with a lot of experience earlier and you'll be able to get get to where you're going faster.

• 30:33Harry Stebbings?

  Penultimate one, what would you most like to change in the world of startups?

• 30:37Speaker 02

  I think the failure rate is probably the thing that comes to mind. There are so many people working on startups and kind of pouring their hearts into it. And I wish there was better information and better education about how startups work. I was really fortunate in my time at Google. I worked at another startup after Google, then I did Y Combinator. I had a lot of context that I was able to learn from, a lot of people that are working in companies and startups don't really have exposure to that. And I wish there was broader access and more of a level playing field when it comes to starting a company.

• 31:04Harry Stebbings?

  Final one, twenty twenty seven, so five years time, where are you and Cambly then?

• 31:11Speaker 02

  So our mission as a company is to bring really high quality English to every English learner in the world. And the company's scaled a ton, the company's doing incredibly well, but we are very, very far from achieving that mission. We've got much, much more ahead of us than behind us and one point five billion people trying to learn English. We've got only a very tiny fraction of them, those people in Cambly today. So a lot of what we're focused on right now, and I think will be for the next five years, is just figuring out how to bring Cambly to more and more of those people. And there's very concrete things we have to do there, like Cambly's pretty expensive today. I think we have to find ways to make it more affordable and accessible to help more people. Talk a little bit about matching. I think matching you with the right tutor is really, really powerful. So I think we've gotten much, much better at that over the years, just with scale.

• 31:54Speaker 02

  But yeah, I think there's a lot more we can do there to get you kind of the perfect tutor for you. And then personally, like, I just want to grow and learn to be a better leader. And I think we've got some of our most exciting years ahead. And I think I'll have to work hard in order to keep up with the rapid growth of the business. And so this is why I'm here. I love learning and I love new challenges and I love that running a startup like no day is ever the same. And so I'm pretty excited about all the new things that are coming over the next few years and trying to keep up and scale with the business.

• 32:22Harry Stebbings?

  Samir, listen, I've loved doing this. I said to you beforehand, I had so many different calls and references. And so I felt like I knew you intimately well, but this has been such a joy. So thank you so much for joining me today.

• 32:33Speaker 02

  Thanks for having me. This has been a total blast.

• 32:37Harry Stebbings?

  It's just such a fantastic story of capital efficient growth, sustainable growth, especially in a world where headlines and spotlight chasing is so much of our industry. I want to say a huge thank you to Samir for coming on the show and sharing the story. If you'd like to see more from us, you can on 20vc.com. But before we leave you today, I want to talk about an incredible tool that I use every single day, Notion. Now, I am the worst for having 50 tabs open and constantly hopping between an endless array of tools. Do you feel me? Are you with me? Well, then Notion came into my life, providing one tool to do it all, with everything from seamless project management to easily organising 20VC's company information. A fascinating stat on Notion usage, more than 70% of companies who start using Notion stop using two plus other tools.

• 33:20Harry Stebbings?

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• 34:05Harry Stebbings?

  With Angel List Stack, you can create a fundraising-ready startup in just a few clicks. Angel List handles your company's incorporation, banking, cap table and fundraising process all in one single place, and this allows founders to focus on building. If you're a founder, you can launch your company at stack.angellist.com/20vc. Whether you're a founder or a funder, you're in great hands with Angel List. And finally, from websites and online stores to marketing tools and analytics, Squarespace is the all-in-one platform to build a beautiful online presence and run your business. There are three things for me that I just love about Squarespace. First, mobile optimised websites. All websites are optimised for mobile, content automatically adjusts, so it just is Really beautiful on any device. Second, email campaigns.

• 34:49Harry Stebbings?

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• 35:17Harry Stebbings?

  As always, I so appreciate all your support and I cannot wait to bring you an incredible episode with Mo Koyfman at Shine Capital next Monday.