Cambly CEO Sameer Shariff: Why I Raised $60M and Didn't Touch a Dollar | 20VC #914

1. 0:00 – 6:12

   Cambly's Founding Story

   1. HSHarry Stebbings0:00

      (beeping) Three, two, one, zero. You have now arrived at your destination. Samir, this is such a joy to do. I've heard so many great things from Jeremy, from Sarah, even from your wonderful wife. Uh, I really did my research, clearly. But thank you- (laughs) ... so much for joining me today, Samir.

   2. SSSameer Shariff0:20

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

   3. HSHarry Stebbings0:24

      That is very, very kind of you. I'm thrilled that you like the show. But I do wanna 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 realization that this was a core pain point that we had to solve?

   4. SSSameer Shariff0:40

      Yeah, definitely. Um, so Cambly grew out of our own experiences learning languages. And so, um, my co-founder and I both grew up here in the US, uh, and we went to the s- the public school system here, took foreign languages as part of that process. Um, and for me personally, I, I studied Spanish, and I never really felt like I was very good at it. Uh, i- in fact, I, I kind of thought I wasn't really a languages person. Uh, and then independent from that, I, I love to travel. I've been all over the world. And, uh, I've been to many places where, um, 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, um, for a good chunk of it, I was traveling on my own, um, and I kept finding myself in environments where I was surrounded by people that only spoke, uh, Spanish. And it really took, like, a, a, a situation like that for me to really come out of my shell and, and practice speaking. Um, and what I found is I, I got so much better at the language s- uh, so much more quickly than I ever did in a classroom environment. Uh, and not just that, it was also just far more rewarding. Uh, oh, the thing I love about travel is getting to meet people and learn about their lives, and I was getting to do that. And so, uh, you know, my co-founder had a really ... My co-founder, his name is Kevin, he had a really similar experience, um, studying French in school and then going to France. Uh, and we kinda got together on this idea, like, "Why can't, uh, we practice these languages whenever we want?" Like, there's plenty of people that, that speak those languages. Uh, they just don't happen to live near us. And so as, as technologists and the product people, we felt like, hey, this sounds like the kind of problem that technology could solve. A- and what the two of us wanted wasn't necessarily a professional teacher or a formal lesson. Uh, what we wanted was just a friendly person to practice with. Uh, and so that's kinda what we set out to build. Um, and as I mentioned, Kevin wanted to learn French. I wanted to learn Spanish. But as we looked at the market, we, we quickly realized that the world wants to learn English, and so we decided to focus on that.

   5. HSHarry Stebbings2:38

      I, I love that, and I love the focus purely on English. We'll dive into the focus. I do just wanna 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?

   6. SSSameer Shariff2:58

      Yeah, absolutely. Uh, so I, I was really fortunate to get a job at Google straight out of college, and so it was my first job. And, um, I feel really lucky. I think Google's an, is an exceptional company. I think just getting to see how a, how a really exceptional company was run, I think, was, was very formative for me, uh, especially early, that early on in my career. Uh, you know, concretely, I learned things like how, how, you know, how to build great software and to do it at scale, uh, 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. Um, and, uh, I think that helped me understand how to m- how to make j- kind of the importance of, uh, data-driven decision-making, and, uh, that's something that served me super well.

   7. HSHarry Stebbings3:46

      H- h- how does Google ... How does Google approach data, if you were to summarize it? (laughs)

   8. SSSameer Shariff3:49

      Yeah, that's a, that's a good one. It's a big one. Um, uh, I mean, d- Google has immense amounts of data, and I think they really appreciate this, the scale of data and how sometimes scale of data can win. Uh, and, uh, a- and I think they just rely a lot on data for decision-making. Uh, so, you know, you might have an i- intuition, I might have an intuition. Uh, they might both be totally wrong. And, uh, what I ... The team I worked on, we ran A/B tests on everything. Uh, and so, uh, you just learn a ton from actually putting stuff out there and, and running a split test on it and, and measuring what the impact is. Um, and, and that's something that actually works. It works, obviously, really well at a, at a company like Google at, at huge, huge scale. But actually, you can employ a lot of those same strategies at a startup in order to kinda hill climb your way to, to, to a better growth engine.

   9. HSHarry Stebbings4:40

      I, I'm so unfair, going off schedule. 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?

   10. SSSameer Shariff4:50

       Yeah. Uh, i- it's a, it's a really good question. Uh, a- and I think, uh, you know, I mentioned some of these things apply really well to startups. But, uh, the reality is, in the very early days of startups, uh, you don't really have much data. And so, you know, in theory, you might think, "Oh, let me just, like, A/B test everything and A/B test my way to success." Uh, and it doesn't really work because, like, you're tiny, there's no data, and you kinda have to, like, deeply understand the problem and largely go off intuition. Um, uh, as your, as your company kinda starts to scale, you can then start to layer in these, uh, these experiments. Uh, but, but it was ... I remember in the early days of Cambly thinking, "Oh, man, I, I know all, all these strategies and tactics, and they just don't work at all (laughs) because we're just too small." Like, if you're getting, you know ... H- we ran a, we ran a test, I think, in the really early days, where we, like, cut our prices in half. Uh, and I was like, "Let me try to measure, like, the price sensitivity of, of Cambly." And we were getting, like, you know, a purchase a day or something, and it was like, you can't measure anything (laughs) -

   11. HSHarry Stebbings5:53

       (laughs)

   12. SSSameer Shariff5:53

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

   13. HSHarry Stebbings6:04

       That is hilarious. Two purchases in a day, and then you realize one's your wife, and you're like, "Oh, that was not-"

   14. SSSameer Shariff6:08

       (laughs)

   15. HSHarry Stebbings6:09

       "... not as successful as I thought."

   16. SSSameer Shariff6:10

       Exactly, exactly.

   17. HSHarry Stebbings6:11

       Um, I know,

2. 6:12 – 8:38

   Why it was so so hard to fundraise

   1. HSHarry Stebbings6:12

      I, I w-... wanna start on the fundraising. We're gonna go through the different elements of the business. But, you know, 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've got in the world. But it wasn't always smooth sailing in the fundraising markets, I heard. I wanted to ask, like, why do you think, in your mind, you struggled fundraising in the early days?

   2. SSSameer Shariff6:34

      Yeah. I think, I think a, a, a couple reasons. Uh, I think one of the really big ones is, uh, well, well, well for starters, Cambly's a, Cambly's kind of a weird business in a bunch of ways. Uh, and I think one of the ways it's, it's strange is, you know, we were two Americans living in San Francisco, uh, building an English education app that was meant for basically everyone who is not here. (laughs) Uh, we were building, we were not building the product for ourselves, and all of our customers were, like, everywhere else. And so, uh, I think Cambly's inherently a little strange in that regard. And the way that translates to fundraising is you go to talk to an investor, and you're solving a problem that they've never really had bef- they've never had themselves before. They probably haven't thought about that much. And what's interesting is it's, it's this immense problem in the world, but it's not a problem we see every day. Um, you know, there's, there's about 7.58 billion people in the world. Um, 6 billion of them don't know English. And, uh, and by the way, of, of those 6 billion, 1.5 billion are actively trying to learn it right now. And so, this is an enormous problem. But, but you and I, we, we speak English already, and uh, we've always spe- we've always, we've always spoken English. And so, uh, it's just not a problem we've ever faced in our lives. And not just that, uh, but everyone we know speaks English. It's not a coincidence that the people we talk to and, and our friends speak the same language as us. And so, it's this, it's an enormous problem in the world that, that we just don't see, uh, at all. A- and the same is true for investors. And so I think that made it challenging to kinda convince people that, "Hey, this is a really worthwhile and important problem to solve." So, I think that's, that's one reason. I, I think another reason is, uh, there have been a, a handful of companies that have tried to tackle language learning before us a- and struggled. And so, uh, I think the, the net effect, uh, kind of a combo of those two, those two factors meant that we just had to get, we just had to hit bigger milestones than, uh, than sort of an equivalent company in order to get that fundraise done. Um, we had to kind of

3. 8:38 – 10:49

   Why Retention is so Hard with Ed-Tech apps

   1. SSSameer Shariff8:38

      prove, prove, prove more.

   2. HSHarry Stebbings8:40

      Can I be so rude and say, when I hear like, "Language learning and ed tech apps," in this way, and then, y- again, you can hate me for this, but try and-

   3. SSSameer Shariff8:49

      (laughs)

   4. HSHarry Stebbings8:49

      ... delay your hate until after the episode. Um, I'm literally like, "Oh, no." Like, high churn, like, the retention is always brutal. It's low ticket prices. It's just like, "Oh, don't do it. No one's done it." Like, "Don't do it." Like, "Samir, I'll give you money to do something else." Um-

   5. SSSameer Shariff9:06

      That's ex- this is exactly, by the way, why it was hard to fundraise. (laughs) Because you're not, you're not alone in that feeling. (laughs)

   6. HSHarry Stebbings9:11

      Y- But, but why am I wrong? Why... I'm sorry, but, and again, I'm going off course here, every education app has shit retention. (laughs) Why is Cambly different?

   7. SSSameer Shariff9:22

      Yeah. So, uh, yeah, retention I think is, is, yeah, one of the, maybe the most important metric in a business, and so super, super important, uh, to, to look at and pay attention to, and make sure you're optimizing for it. Um, I think, like, if you look at e- education technology, like, a lot of the services that exist are either pure software services, um, where you can kind of quit (laughs) whenever you want and no one really cares, or like, a giant classroom, uh, like a, like a, you know, massive online course, where also you can quit, uh, whenever you want and no one cares. Uh, Cambly's quite different from that. Cambly is, uh, a one-on-one conversation, not too dissimilar to this one. Uh, and I think because of that, it's inherently just like, much more engaging. It's like, this human to human connection. Um, and not just that, there's also, you build relationships. You actually, like, our students get to know our tutors really well. Uh, and, and yeah, there's, there's strong relationships that are built there. And so, in the same way you wouldn't like, uh, you know, set up a dinner with your friend and then just sh- stand them up, uh, you kinda feel (laughs) like you've got some, some obligation to, to, to show up to your, your class in Cambly. And so, uh, I think there's, there's a social component, and I think it's just f- a lot more fun and engaging to, to, to sort of really exercise the skill of speaking English, uh, by practicing in these one-on-one conversations. I think that's a big part of why Cambly looks and feels so different from, from your average education, uh,

4. 10:49 – 11:54

   Negative Incentives

   1. SSSameer Shariff10:49

      technology company.

   2. HSHarry Stebbings10:50

      I, I, I totally get you. Did you ever think of doing negative incentives? I've spent a lot of time studying negatives incentives where you actually penalize people for not doing it, which is where you actually start fining them for not showing up. (laughs) Um, there was a brilliant company that did it years ago for gyms. If you didn't go to the gym, they'd fine you.

   3. SSSameer Shariff11:08

      (laughs)

   4. HSHarry Stebbings11:08

      Um, have you ever looked at negative incentive structures?

   5. SSSameer Shariff11:11

      Uh, I can't say we have. Although we've experimented with a few different models where, uh, I think one thing that's been pretty helpful is w- we, we kind of built right into our, like, business model, it kinda teaches you how to use the product. Like, you have, um, you know, a, a fixed number of minutes per day, uh, and it's use it or lose it. And so, uh, I guess you could, you could say that's a, a mild negative incentive-

   6. HSHarry Stebbings11:35

      Yeah.

   7. SSSameer Shariff11:36

      ... that you lose those minutes if you don't, uh, if you don't use them. And so, but we, what's really important about learning a language is consistency and daily practice. And so, uh, it's kind of baked right into the plan to teach you how to use the product.

   8. HSHarry Stebbings11:47

      I totally get you. A final one and then I promise we'll get back to schedule. Retain, r- like, retention is, is a wonderful, like, focus

5. 11:54 – 13:42

   How do you define a "Retained User"?

   1. HSHarry Stebbings11:54

      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 behavior process that you would consider a retained user for you?

   2. SSSameer Shariff12:06

      Yeah, so our North Star metric from, from, like, the pretty early days was, uh, paid usage, so the nu- the amount of minutes that students spend, uh, actually using the product. And, uh, every minute there is a tutor teaching and a student learning, and so what I love about that metric is it's a, it's a value-delivered metric. Um, and that may seem obvious as I describe it to you, but actually I think a lot of the companies that came before us, um, optimized much more for revenue. They kind of just focused on the, the revenue number. And the, the challenge with that is, uh, you can, you can sell the dream for a product people don't actually use, uh, and, and make a lot of money in the process, uh, and, and actually a lot of those companies would charge a lot of money up front for it. And it's, uh, 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, uh, you're heading down a really bad path. It's, it's totally unsustainable and eventually will catch up to you. And so, uh, 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. And so we, um, w- I think one of the best things we did towards that was picking the right North Star metric. Like, this is all about usage. Uh, we want people to not just pay for the thing, but actually use it, uh, and, and as a result of that, I think we've, we've been able to make a number of really good decisions along the way that has, has helped us drive long-term sustainable growth.

   3. HSHarry Stebbings13:34

      I am totally with you, and I think just having the clarity of knowing exactly why it's the North Star and how you measure that retention is, is crucial

6. 13:42 – 15:40

   The Value of a NOT Being Able to Fundraise

   1. HSHarry Stebbings13:42

      and one that I don't think enough founders think about. Uh, 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 (laughs) of not being able to raise early on, Samir?

   2. SSSameer Shariff13:59

      Yeah, no, totally. Well, don't, don't get me wrong. It's painful at the time, uh, but then when you look back and you look at, at kind of where it led you, uh, I think there's, there's often some really good things that come from it. And so, um, I think, you know, when you don't have a lot of resources, you just have to, uh, you have to work with what you have and, uh, you learn to be really, really scrappy, really efficient. Uh, and, uh, a lot of those decisions you make without a lot of capital, y- you know, I think in our case helped us make, helped us build a, uh, a product and a marketplace that was just, like, uh, highly, highly efficient. And then as we scaled it, we were really, really capital efficient in the process. And so, you know, I, I can give actually a concrete example. Like, we went out to raise our series A and, um, uh, and it, it was, it was a challenge. Like, it did not go as planned. Uh, and, uh, you know, we had to basically pull the team together and say like, "Hey, we were planning on raising an A. It, it's not gonna happen. Uh, we're, we're gonna start executing on plan B." And plan B was actually to get the, the company to cash flow positive. And for sure it was a stressful time in the company, but we made a number of really good decisions in a very short period of time that, that, you know, four months later led to the company getting to cash flow positive. Uh, and, and we've been cash flow positive ever since. And, uh, as you can imagine, that has served us super, super well. Uh, it, it, it, for, for one thing made fundraising a lot easier when we went back, uh, when we went back out, you know, uh, a little time later.

   3. HSHarry Stebbings15:37

      (laughs)

   4. SSSameer Shariff15:37

      Uh, it just, the conversation was, was very, very different.

   5. HSHarry Stebbings15:39

      You're giving

7. 15:40 – 17:22

   Decisions that Led to Becoming Cash Flow Positive

   1. HSHarry Stebbings15:40

      me so much to unpack here. Um, fir- first, what were some of the... You said, like, the decisions you made, three or four that really moved the needle. What were those three or four decisions that really moved the needle?

   2. SSSameer Shariff15:52

      Yeah, so, uh, uh, one, one nice thing about Cambly is we've, you know, it's a, it's a marketplace, it's a two-sided marketplace, students on one side, tutors on the other. We, we, uh, we very... From basically day one, we, we charged for the product because it was just, it would have just been unsustainable not to. And so, um, we had a, you know, we had a business model that made revenue from day one. Um, there's a lot of leverage in pricing, and I'm sure you've heard this from, from other folks before. And so, uh, one of the things we did, uh, in that period was, was, uh, change our pricing basically and, and, and made sure that we, you know, we had all this money flowing through the system, we wanted to make sure we were taking a healthy margin from it, and, and that could... sort of slipped over, over time. And so, uh, pricing was a, was a huge one. Um, uh, we also offer students, like, a, a number of plans and, um, if they want to commit for a longer period of time, then they can pay up front for that. Um, so that has really cash- really healthy cash flow, uh, dynamics for the business. And so, uh, that was another one. Um, I think throughout our history we've just kept a really, really lean team. And so, um, we've, you know, we've done a lot with, like, a really small team. And, and that wasn't necessarily a decision that we, that we made kind of in 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. And including, like, me and my co-founder wearing a lot of different hats and, and serving a lot of different roles for the company, like, we just kind of tried to figure out how we could be as efficient as possible, uh, throughout.

   3. HSHarry Stebbings17:21

      Well, we're gonna talk about

8. 17:22 – 20:22

   Cambly Raised $60 million and Didn't Spend a Dollar

   1. HSHarry Stebbings17:22

      you having every role in the company in a, in a, in a little bit.

   2. SSSameer Shariff17:24

      (laughs)

   3. HSHarry Stebbings17:24

      I do want to ask, um, as a VC, and this sounds ridiculous in 2022, but as a VC today I'd be going, "Cash flow pot," well, not today, last year, "Uh, cash flow positive?"

   4. SSSameer Shariff17:34

      (laughs)

   5. HSHarry Stebbings17:34

      "Cash flow positive?" Like, you've raised all this money now and, uh, you know, I spoke to Jeremy, he told me you haven't touched a dollar of your series A or your series B.

   6. SSSameer Shariff17:42

      (laughs)

   7. HSHarry Stebbings17:42

      Like, bluntly, you're not optimizing for growth, uh, is, is kind of what one would take away from this. Like, how do you feel about that growth versus profitability now? And now you have the leverage, is now not the time to spend?

   8. SSSameer Shariff17:58

      Yeah, so I guess the one thing I'll call out is, uh, just because we haven't touched the series A bu- money and the series B money, it doesn't mean that we...... sort of, um, behaved exactly the same, h- you know, had we not raised that money. Like, having that cash cushion, I think, allows us to be much, much more aggressive, uh, and, and make a very different set of decisions. And so, um, w- I think we've benefited a lot from the cash even if we haven't touched it-

   9. HSHarry Stebbings18:22

      Oh.

   10. SSSameer Shariff18:22

       ... because it's allowed us to, like, plan around that. Uh, not to mention as, you know, Jeremy, Jeremy Levine and Sarah Tavel are, are incredible. Like, they've been so instrumental in, at helping us figure out how to continue to scale the company, how to recruit the right people into the organization. And so, it's not just the money you're getting, you're getting, like, uh, real expertise. And so, I think we've benefited a lot from those raises and I, and I feel really good about it. But, but to come back to your question about, you know, growth versus profitability, um, you know, the way I think about it is, I wanna grow as fast as, (laughs) as humanly possible, uh, but I want to do it in a sustainable and healthy way. And, uh, 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, and I think to, to Jeremy Levine's credit, uh, he's a big believer in that as well, no matter what, you know, which way the tide is going. Uh, and so, you know, I believe you wanna build, uh, you wanna grow as fast as you can, but do it re- really sustainably. And, and I think one way to think about this is, you're not growing, like, just to, like, hit a milestone and then do the next fundraise. Like, that's not how I think about it. How I think about it is, uh, I wanna figure out the mechanisms that will allow me to grow, uh, for a very long time. And so if you think about those early days as, like, I'm experimenting, like, I'm figuring out what are the things that work. And, and if you're kind of blowing through a lot of cash and doing unsustainable things, there's a really good chance you're learning the wrong lessons, uh, and they're not necessarily gonna serve you down the road. And so, uh, we've always tried to grow in, in a really sustainable way, and I think, you know, I think if you look at the right time horizon, you look at like, hey, I wanna, I wanna figure out how I'm gonna scale this company over the next 10 or 20 years, uh, we're in this experimentation stage where we're figuring out the things that will allow us to do that, and we're making those investments. And so, uh, I think that's, like, a framing that I think will make you maybe less inclined to sort of burn a hole in your, in your cash, uh, because you might have the wrong takeaways from that.

   11. HSHarry Stebbings20:21

       I'm sure a lot of founders

9. 20:22 – 22:12

   How do you advise founders when it comes to capital efficiency?

   1. HSHarry Stebbings20:22

      ask you for advice, especially now. Um, how do you advise founders when it comes to capital efficiency, when it comes to fundraising, growth, spend, given your experience and perspective?

   2. SSSameer Shariff20:35

      Yeah, I, I always caveat that with this is my own, my own, uh, take and my own experience, and, you know, your, your mileage may vary. Uh, uh, I, you know, I think y- we've talked a little bit about how people were pretty skeptical about, um, the, the space that we're in, and, uh, so I kinda caveat it with, "Hey, this is, this is my experience." Uh, uh, but, but I'm a big fan of, of being really lean and being really capital efficient in the early days, and, uh, figuring out how to get, uh, just really focusing on the core business, uh, and making it really strong and healthy and getting that early traction, uh, and kind of plotting a path for you to be able to... for the business to be able to stand on its own two feet. Uh, it just gives you so much optionality, uh, and, you know, again, from my personal experience, when I've not done that, uh, it's been hard. (laughs) Uh, and it was alwa- it wasn't always hard to predict. It w- I mean, it wasn't always easy to predict either, right? Like, I thought, hey, the company's doing pretty well. Like, we're a great team. Like, we should be able to g- we should be able to do this next fundraise. And, and then I've regretted, I think, maybe that, uh, unchecked optimism, and so I often try to, try to balance out founders who I think maybe, maybe come in with, uh, similar sort of unbridled optimism, but hey, here's what some of the realities might look like. This might play out this way. Just, like, make sure you're not kinda putting all your eggs in one basket. And so, uh, that, that's kind of often the tone I take when I'm, when I'm advising folks, uh, specifically around, like, an upcoming fundraise.

   3. HSHarry Stebbings22:06

      I think there's a lot of realizations being made and being realized today that, uh, sadly are not the

10. 22:12 – 25:20

    How do you define high performance in business?

    1. HSHarry Stebbings22:12

       same as last year. So I, I totally agree with you. I think that's good advice. You mentioned, like, how you think about growth and sustainable growth. I, I think, you know, I want... (laughs) Coming from the guy with the fedora, I wanna talk about you, uh, and the different hats that you wear within the companies. Because whenever I speak to anyone, they all spoke about your skill here, and to di- dig in here. So I wanted to start on performance. How do you define high performance in business today as a leader?

    2. SSSameer Shariff22:37

       I think about performance as, uh, sort of focus, uh, you know, results, and driving for impact. Uh, and, uh, I think, like, you know, uh, in the early days I used to think of that kind of, I think, very much at the individual level. Like, what are you personally doing to kind of drive an impact in the business? And then obviously as the organization has scaled, I think I've, I've really grown to appreciate, um, what, what great leadership looks like and how... and then the type of leverage that has, uh, o- on the business. And so, how do you create an organization and an environment that, that drives towards impact and, uh... A- and I think one of the things I've, I've been thinking about even more recently is, you know, we've got a much larger company now. Like, how do you get everyone across the company aligned and kind of running in the same direction? Uh, and so, uh, uh, my, my performance, my, my definition of high performance I think has evolved over time, but, but it started off with sort of individually what are you doing? How, how, how much are you driving for results and impact? Uh, and then it's kind of grown and evolved into, um, how you get your organization, or whatever kind of, whatever's under your purview, driving, driving in the right direction, and, and everyone on your team sort of pushing towards impact.

    3. HSHarry Stebbings23:51

       A couple of the things that always strike me when you grow a team quickly like you are, how do you retain speed with increasing team size? So often you get bloat, you get processes. How do you think about retaining speed with scale of team?

    4. SSSameer Shariff24:06

       Yeah, it's a- that's a tough one, uh, and something I've definitely, like, has, has been challenging. I don't know if I have a silver bullet, uh, for it. I think, uh, when you're small, it's really easy to kind of know what everyone is doing, and so you can kind of almost personally, uh, make sure that like, people are focused on the right things and you can g- kind of give feedback in a one-on-one context. Uh, but as you grow, obviously that, that quickly breaks down. And so I, I think you have to introduce like a bit more, um, you know, process and organization around it. Uh, uh, things like planning, things like setting goals, uh, being really deliberate about who owns what and like, uh, giving, giving folks across the or- org ownership over, you know, ownership autonomy over, um, going after certain goals. And so, uh, but, but it's a learning process. I think we're still figuring it out and I think, uh, it's, yeah, it's something that I think has, has been, has been challenging and, and yeah, we're, we're, we're getting better at it every day.

    5. HSHarry Stebbings25:07

       Speaking of learning processes, I always think we learn from, as a leader, from tough times and mistakes that we've made or tough times we've experienced. Um, when you think back through the Cambly journey, and this is a really hard one to throw on you, so forgive

11. 25:20 – 30:48

    What's the most painful experience at Cambly that also was good for you?

    1. HSHarry Stebbings25:20

       me. But, um, I wanna ask, when you think back through that journey, what's the hardest, like wh- what's 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?

    2. SSSameer Shariff25:36

       Yeah. So I'd have to go back to that same one that I kind of touched on, uh, when we went to go out and raise our series A and, uh, it did not go as planned. And so, uh, you know, I, I mentioned Cambly's cashflow positive today and has been for the last five years. Uh, that was not, you know, that did not happen... That was not our choice. We didn't say, "Hey, today we're gonna become cashflow positive." Like, we became cashflow positive bec- uh, you know, out of necessity initially. Uh, and so, you know, we, we had some amount of money in the bank, we were, but we were burning a decent amount and we went out to raise and it didn't happen. And so we kind of had this moment where we're like, "Okay, well this is..." You know, it was the first time, first and only time in our history where we had, um, sort of an existential risk. And, uh, that's stressful, uh, but it also brings a lot of clarity in terms of what you need to focus on. And, uh, what me and my co-founder noticed, I think, you know, as we kind of started executing on plan B and figuring out how we're gonna, how we're gonna, uh, plot a path, uh, to, to cashflow positive for the business, what we noticed is that like the rest of the company was kind of continuing to do the things that they were doing, and they were good things, but they, they, you know, we were, I think, coming in and saying, "Hey, no, stop doing that. Do this other thing instead." And, and I think what we realized is it's probably seemed kind of arbitrary, like, "Why are, why are Kevin and Samir saying, like, stop doing this and, and work on this instead?" And, 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, (laughs) you know, keep the company from running outta cash. And so when we had this realization, wh- wh- what we decided to do, and again, this was, this was very scary at the time, uh, but I think it was a really, it was a really good growth moment for me and something I, I learned a ton from is, we, we decided to pull the whole company together and say, "Here's what happened." Like, "We told them we were raising a series A, it didn't happen. Uh, here's what-"

    3. HSHarry Stebbings27:31

       Were you wor- were you wor- were you worried about them losing faith, losing morale, going, "Oh God, Cambly's not the rocket ship that I thought it was, I'm gonna move." I... that's a dangerous move.

    4. SSSameer Shariff27:41

       Yeah.

    5. HSHarry Stebbings27:41

       Were you worried in that moment?

    6. SSSameer Shariff27:43

       Yeah.

    7. HSHarry Stebbings27:43

       And how do you think you did it?

    8. SSSameer Shariff27:45

       Yeah, I was, I was absolutely worried in that moment. And, uh, I think there's a lot of, you know, it's, it's I think inherently a very scary thing to do. Uh, and I can't say that I was like, "This is definitely the right decision" immediately. Like, I had to kind of like work through it, but, and work up enough courage to do that. Um, but, but ultimately I think we decided like in order for us to figure out how to get out of this, this predicament we're in, uh, we need the team to help us. Like, there's, there's no other way to do it. And so, uh, I think there was a, a fair amount of trust and faith that like, hey, we've got a, we've got a group of people that I think can, uh, can, will pull through for us. And, uh, I, I think what helped was, um, we, we told them, you know, "Here's the update, like, the fundraiser's not happening, here's what we need to do as a company." Uh, and I think it was helpful that we had a plan. (laughs) Uh, we didn't just say, "Okay, things didn't go according to plan. Any ideas, anybody?" Like, we, we came in and we said, "Here's what our plan is." And not just that, we'd actually started executing on it, uh, through some of the things I mentioned, some of the price changes, helping our margin, increasing our margin. And so we didn't just have a plan, but then we showed a graph of like, "And here's what our gross profit was two months ago. Uh, here's what it looks like today. We're actually on the path." And so I think it was helpful to, I think, uh, show that, hey, here's the way out of it and we're on that path, but we need all of your help in order to get there. Uh, and I think that level of transparency was, was yeah, like I said, scary, but I think really, really powerful. And, and we, we entered that room with a team that was, I think pretty, you know, misaligned for, for lack of a better term. Like, we were just prioritizing different things. Uh, and we left that room with a team that was very highly aligned that like, "This is what we have to do as a, as a company." And, and it was incredible. I mean, coming out of that, like everybody across the company started working on all of the most important things to make sure that we could get the company to a, to healthy, sustainable, and in our case, cashflow positive place. And, and I think that was, 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, and draw lessons from that all the time.

    9. HSHarry Stebbings29:52

       Were you a remote team then?

    10. SSSameer Shariff29:54

        We were not, no, we were in person.

    11. HSHarry Stebbings29:56

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

    12. SSSameer Shariff30:00

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

12. 30:48 – 35:54

    Sameer's Learning Process

    1. HSHarry Stebbings30:48

       No, I, I am totally with you. I mean, speaking of kind of the team, eh, no one more important than your co-founder. I spoke to Kevin before the show, um, and he said, uh, "Wonderful, wonderful trait of yours is your ability to learn." Um, he did say there's a downside, which we'll get to later. (laughs)

    2. SSSameer Shariff31:03

       (laughs) .

    3. HSHarry Stebbings31:03

       Um, but, um, he said your learning process, like figure out ... H- he's so smart and he learns so many different things so fast. What is your learning process? How do you deconstruct new subject matter? How do you think through how to learn?

    4. SSSameer Shariff31:18

       Yeah, so, uh, it's maybe not a secret that I, I like immersive, uh, learning. Uh, that's what, what Cambly's all about. Uh, and so I like to really like dive deep into a topic, uh, a- and really kind of try to wrap my, my, my head around it. Um, uh, I also like, uh, I'm very much like a first principles kind of thinker, and so, uh, it's really important for me to not just, um, understand the what, but also the why. Um, like, 'cause, 'cause sometimes, you know, those lessons might not apply very directly, and if you don't understand like where stuff is coming from, you might take away the wrong, you know, you might have the wrong takeaway from that. And so, um, that's, that's really, really, really important for me as well. Um-

    5. HSHarry Stebbings32:02

       So like for me, for me when I think about my learning process is generally ... Actually, I hate reading. Um, I gain no, no interest in reading. It's boring and it's lonely. Um, I just talk to the 10 smartest people I can find on the space-

    6. SSSameer Shariff32:17

       Totally.

    7. HSHarry Stebbings32:17

       ... and then I write three bullet points after each goal and I find the commonalities between what they said and the ones that are the most important. I then look into more, and then I'll actually do some research. That's my-

    8. SSSameer Shariff32:28

       Yeah.

    9. HSHarry Stebbings32:28

       ... process, which is why I did interviewing VCs actually. That's why I started the show 'cause I just wanted to learn that much.

    10. SSSameer Shariff32:34

        That's great.

    11. HSHarry Stebbings32:34

        But, like that's-

    12. SSSameer Shariff32:35

        Yeah.

    13. HSHarry Stebbings32:35

        ... that's mine. Do you see what I mean? A- do you think of your-

    14. SSSameer Shariff32:37

        Yeah.

    15. HSHarry Stebbings32:37

        ... process like that?

    16. SSSameer Shariff32:39

        Yeah, yeah, totally. Uh, so, I think another thing that's like been really valuable and helpful for me is I, I love like applied learning, and so, uh, I love taking knowledge I have and then applying it. I think it's just like much more satisfying and rewarding. And so, and I think I've always felt that way like I, I think back to like, uh, when I was in high school and I was learning calculus, uh, we, you know, I went home and I like told my, a couple of my friends, "Hey, I just learned this new thing." And we were working on building a bike ramp, uh, and I was like, "Oh hey, let's ... I know exactly to how to figure out like what the, what the slope, (laughs) uh, you know, what the slope of the trajectory is on the way out." And kind of applied the calculus I just learned like earlier that day to figuring out how to build this bike ramp. And so, it was like just made it way more fun, and so, I think another, another good example of that is, uh, I learned accounting in, uh, in college, and I, and I felt like, "This is pretty boring." Uh, a- and then when I came back to it at Cambly, and my business really depended on it, uh, all of a sudden it was like this really, really interesting thing that I was like really deeply like, "I gotta figure this out." Uh, and so I, I love applied learning. Um, I think the other thing, yeah, the other thing that comes to mind is, is, you know, one-on-one interactions. I think, you know, when I think about the times when I've learned the fastest, um, they're all like one-on-one interactions with someone who knows way, way more about the subject matter than me. Um, and I think what's really, really powerful about that is, uh, I can, uh, I can kind of, uh, I don't spend any time talking about the things that I already know. Uh, I can kind of stay right on the edge of my learning curve and kind of hang out there, and I think that's, that's when you maximize your rate of learning. And so, um, I'm a huge, huge fan of that, and, you know, that's what Cambly's all about as well. Uh, it's all one-on-one interactions with, with someone who's an expert at speaking English in this case. Um, and I think a, an interesting ... I don't know if you've heard of a study called Bloom's two sigma problem?

    17. HSHarry Stebbings34:39

        No.

    18. SSSameer Shariff34:40

        Uh, but it's this re- it's this really interesting, uh, study that was done decades ago now where, uh, basically they compared, uh, one-on-one tutoring to a traditional classroom environment. Uh, and what they found is that, uh, the traditional, uh, the, the one-on-one tutoring was, was far more effective than a classroom environment, and, and when I say far more effective, I'll quantify it, the two sigma stands for two standard deviations. So it was two standard devia- standard deviations better, and, um, what, uh ... It- it was this like super interesting, uh, study, but it was kind of academic 'cause, 'cause, you know, decades ago like what do you do with that? You're like, "Okay, this is far better, but like how do we actually bring that to market?" And, uh, I think what we're doing at Cambly is we're actually taking that and scaling it to a level it's, it's never really seen before in the world. Uh, uh, we're, we're w- one of the largest, if not the largest, one-on-one tutoring platforms in the world right now. And so we're running this kind of enormous experiment, uh, applying that, uh, applying that study, and, uh, yeah. It's a, it's a highly effective way to learn. I think what's really pow- yeah, what's really pow- uh, powerful about one-on-one is it's,

13. 35:54 – 36:27

    Supply vs. Demand at Cambly

    1. SSSameer Shariff35:54

       um, really personalized for, for you.

    2. HSHarry Stebbings35:57

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

    3. SSSameer Shariff36:03

       Uh, so we've always been a demand-constrained marketplace, so, uh, we can grow the marketplace as fast as we can find demand. Um, you know, as I mentioned, there are, there are billions of people trying to learn English, so there's no shortage of demand at all. There's this enormous problem, uh, in the world. Uh, it's purely a matter of how do you reach those people in a, uh, in a cost-effective way. And, uh, and that's, yeah, that's been

14. 36:27 – 37:43

    How Cambly Acquired its First Teachers

    1. SSSameer Shariff36:27

       the general bottleneck of our business.

    2. HSHarry Stebbings36:29

       Totally get you. How did you acquire the first teachers?

    3. SSSameer Shariff36:33

       So, really early on, yeah, we were just kind of scrappy across the board. We, uh, we posted to job boards and forums, uh, and kind of got our initial tutors that way. Uh, and being a tutor in Cambly is actually, like, a really cool job. You get to, uh, talk to interesting people around the world, uh, learn about their lives, uh, and, um, you can, uh, you get paid for it, and, and you can work, like, whenever you want, uh, and so totally flexible hours. And so, it's a pretty, it's a pretty cool job, and I think as a result of that, uh, uh, there's a lot of, there's a lot of, uh, word of mouth growth. Uh, and so a lot of our tutors come from just, you know, hearing about it from a friend, uh, and we've actually have, we've had, I think for most of the history of the company, a long wait list of tutors that are really excited to join. And, uh, we just onboard them kind of in lockstep with the student side of our, uh, our student side growth.

    4. HSHarry Stebbings37:28

       You mentioned distribution there and just getting to them. I think a lot of distribution is actually consumer resonance and storytelling and kind of product marketing. It was another skill that, that Kevin and Jeremy actually said you were fantastic with. So, how do you think about

15. 37:43 – 39:56

    What makes a great story?

    1. HSHarry Stebbings37:43

       what makes a cruly- (laughs) A cruly? How do you think about what makes a truly great story and really effective product marketing today?

    2. SSSameer Shariff37:52

       Yeah, so see, I, I, I like, I like storytelling. I, I find it fun. And I, I think, like, the way I would dissect that is, I think stories, uh, about people are just much more interesting than, than stories about, you know, numbers, or categories, or, or broader things like that. And so, um, you know, I think it's a lot more compelling to hear about, like, one student on Cambly, uh, and their personal journey. It just, it draws you in a lot more. Um, uh, I, I also love to share, like, small details, I think, that, that, uh, that kind of makes people resonate and, and understand the story. And so th- that's a personal, you know, stylistic, uh, preference of mine. I can give you an example. Like, when I'm, when I'm talking about Cambly, I often, uh, bring up, uh, this, uh, Turkish pilot who started using Cambly. And, and when we heard about him, we were like, "Oh, that's interesting." Like, "Why, why would he use Cambly as a, uh, uh, you know, as a, as a pilot?" And what we learned as we kind of dug in was if you're, um, yeah, if you're a pilot in Turkey, and you, uh, and you only know Turkish, uh, you can fly anywhere you want in Turkey. But if you wanna fly internationally, uh, English is the official language of air traffic control. And so, um, if you could just learn English, uh, then you'll get a promotion, and you can fly anywhere in the world you want. And so, uh, that, you know, it was a very, very clear ROI. There's a very clear demand for wanting to learn that, and I think as a result of that, this Turkish pilot, uh, went on to learn English on Cambly a- a- and was able to, to fly internationally. And, and we actually have a lot of pilots like that. And so, uh, yeah, I think that's a good example of, like, the type of student that's on Cambly and why people are using the service. Uh, but what I, why I mention that here is, um, I tell that story when I'm talking about Cambly, and, you know, weeks, months later, people are still talking about Turkish pilots. And so I think there, th- the level of detail there and kind of the fact that it's about this, this individual's journey, I think, makes it really memorable. And, and I've seen that one, that one resonate with people really well.

    3. HSHarry Stebbings39:54

       I, I, I love that, and I,

16. 39:56 – 41:30

    Leadership: What gets harder/easier over time?

    1. HSHarry Stebbings39:56

       I didn't know that actually in terms of their ability to do that. Um, can I ask you, leadership is ever-changing. What gets harder over time, Samir, and what gets easier?

    2. SSSameer Shariff40:05

       In some ways, running the company can get easier because you hire all these people with, uh, a ton of experience. And, uh, they, they ru- they run, actually, large parts of your org, and so, uh, and, and you can learn from them. And so, uh, you know, as the company has scaled and we've been able to bring on some, some folks like that, we're just, I just don't have to be into details as much anymore. Like, they know far more about their domains than I do. And so, you can kind of hand that off and let them, let them run, run the company, or, or sort of run, run their piece of the company. Um, so I think that gets easier. Um, uh, a lot of stuff gets harder, I think. You know, the, the, the scale of the problems are just bigger. I mean, you've got, uh, a much bigger business. You've got, uh, much more customers. You've got, uh, a bigger team. And so, everything's just a, you know, everything is just higher stakes. Uh, and so I think there, there are a lot of challenges that, that, that come from that. Um, uh, and also culture, I think, uh, g- you know, is, can be... You know, scaling your culture can get challenging. I think when you're really, really early on, you're, you know, you have one-on-one relationships with everyone at the company, and you can influence that very much personally. Uh, but as the organization grows, you have to find ways to kind of, to scale that and, uh, bring on new people and kind of bring them into your culture screen for that.

17. 41:30 – 42:38

    The First Thing to Break in a Scaling Organization

    1. SSSameer Shariff41:30

       Um, and so I think that, that can be challenging as well.

    2. HSHarry Stebbings41:32

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

    3. SSSameer Shariff41:38

       Uh, I think, like, the, the thing you touched on earlier around, like, how do you, how do you keep, uh, how do you increase your velocity as you grow the organization? I think that's a really challenging one that, uh, can be, can be misleading because, uh, it feels like if you add people to your company, of course you'll go faster. But it's not a given th- that, that, that happens. And, and I think Kevin and I, like, had been w- uh, you know, in organizations where we saw, like-... teams grow and then not necessarily move faster as a result of it. And so, uh, I think that's one that, like, is particularly top of mind for me. I don't know if it's the first thing that breaks, but I think it's one that, you know, how do you make sure that as you add people, uh, your, your company actually moves much faster? Uh, and if it moves slower, that's, that's terrible, right? But even if it's moved at the same speed, you've now just become a less efficient company. Uh, and so figuring out how you can still drive that same level of impact, uh, as the organization grows, I think is, is a real challenge, and I think we're getting

18. 42:38 – 44:54

    Cambly's Biggest Hiring Mistakes

    1. SSSameer Shariff42:38

       much better at it, but it's been, it's been a learning curve for me, for sure.

    2. HSHarry Stebbings42:41

       What have been your biggest hiring mistakes? Hiring is always a challenge. What have been the biggest hiring mistakes for you?

    3. SSSameer Shariff42:48

       Yeah. So, uh, we have this really interesting country manager model, and I, I'd love to talk a little bit more about that. But I can, I can zoom into this, this, this, uh, question. Um, you know, when we were hiring country managers, and, uh, again... Actually, maybe I'll take a, a minute to, like, talk about our country manager model.

    4. HSHarry Stebbings43:07

       Sure. Yeah.

    5. SSSameer Shariff43:07

       Um, so we, we've, um... Because of the, how, how unusual Cambly is as a business, uh, we've, uh, we kind of discovered fairly early on that, uh, we, 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. And so, uh, the, literally the first hire that Kevin and I made, we were two sort of former Google software engineers, uh, and employee number one was a Korea country manager. So, pretty odd makeup of our three-person team.

    6. HSHarry Stebbings43:34

       Correct.

    7. SSSameer Shariff43:34

       But when you think about the space we're in, uh, and the, you know, the business we're in, uh, where our customers are, it made total sense. And what we found was if you could hire the right person, uh, it was a massive unlock. I mean, Korea went from being kind of not even really on the map to, to quickly becoming our biggest market shortly after making that hire. And so, obviously, a lot of really interesting lessons there. Um, and, um, I guess we did a good job with that first hire. I think over the process, what, what we learned is, there are certain qualities that, that are really, really important. And so I think one that comes to mind for your question was, uh, you can hire a great, like, marketer, for example, uh, but if they have any level of success, they have to then start to build out a team. And so, uh, you wanna make sure that they're, they can, they can lead as well. They're a manager. And I've made some mistakes there, where we've hired some country managers that, um, either were great individual marketers, but, but had more challenges, uh, running a larger team. Uh, we've hired some, uh, that have, uh, struggled with some of the analytical pieces, which we find, we found to be really, really important in that role. And so, that's probably the first thing to come to mind, in terms of, in terms of hiring mistakes. But hiring's really hard. Like, you're gonna make mistakes, and I think you just sort of have to be comfortable with that and, and, uh, and when you do, you have

19. 44:54 – 46:20

    Signs an Individual Can Become a Leader/Manager

    1. SSSameer Shariff44:54

       to correct it as, as quickly as you can.

    2. HSHarry Stebbings44:56

       When you look back, what are some of the signs that an individual contributor is able to scale into a leader and a manager?

    3. SSSameer Shariff45:04

       Uh, I mean, I think for starters, like, they have to have an interest in it, and they have to want to do it. And so, um, that's really important. Uh, you know, I think, I think you can look for an aptitude and, uh, some, some sort of core skills as well. Uh, uh, you know, I, I think, like, the, sort of the EQ side of things, like, are they, are they not just really smart, but they actually, like, understand people really well? I think that's, uh, what motivates people, um, you know, how people approach, approach things, how people think about, uh, their careers. Uh, these are all the sorts of things that I look for, to, like, see if someone is gonna become a, a, a good manager. I think self-awareness is also really important. Um, uh, and humility is, is one, where, like, uh, I think being a manager, it can be a humbling experience. (laughs) And, uh, I think if you, if... You know, I think a lot of us managers come in thinking like, "Oh, I've already, like, you know, led a team before. Like, I've been a tech lead," or ... I mean, this is for sure how I thought about it. Like, how hard could, could management be? Uh, and then it's a bit of a rude awakening, and I think you have to be really open to that and, and open to learning. And so, uh, I think h- sort of a combo of humility and, and, uh, interest, uh,

20. 46:20 – 47:25

    Do you have a high tolerance for risk?

    1. SSSameer Shariff46:20

       and ability to learn, I think are all, all, all factors that I look for.

    2. HSHarry Stebbings46:23

       Final one. Do you have a high tolerance for risk?

    3. SSSameer Shariff46:27

       Uh, s- in some ways, yes, and in some ways, no. I think, like, uh, I mean, personally, I love to, like... You know, I'm a bit of an adrenaline junkie, and so, uh, I used to skydive when I was in, like, college, and hang glide, and you know, love to ski, and so I, I take a lot of risks. Uh, you know, or, you know, you could say risks in my, in my personal life. And I think starting a company like Cambly was... You know, leaving a cushy job at Google and, and deciding to kind of get into startup world was, was a pretty big risk i- in itself as well. Um, but I also like to think things through really carefully. I like to think decisions through. Uh, and so, um... Yeah, I don't know. Uh, a, a mix of an answer to that. I, I, I'm open to risk, but I want to really, like, understand what I'm, what I'm getting into first before I, before I take the leap.

    4. HSHarry Stebbings47:14

       I, I totally get you. Uh, I, I do want to move into my favorite though, which is a quick fire round. So, you know how this goes.

    5. SSSameer Shariff47:19

       Yeah.

    6. HSHarry Stebbings47:19

       I say a short statement, you give me your immediate thoughts. Does that sound okay?

    7. SSSameer Shariff47:23

       Sounds great. Yeah, let's do it.

21. 47:25 – 48:30

    Sameer's Favourite Book

    1. SSSameer Shariff47:25

    2. HSHarry Stebbings47:25

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

    3. SSSameer Shariff47:31

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

22. 48:30 – 49:57

    Sameer's Biggest Stength/Weakness

    1. SSSameer Shariff48:30

       uh, all about one-on-one interactions and human connection itself. Yeah, I'm a big fan of that one.

    2. HSHarry Stebbings48:34

       What do you think is your biggest strength and your biggest weakness, if you had to do 30 seconds on each?

    3. SSSameer Shariff48:40

       Yeah, uh, I think biggest strength is probably giving people a lot of ownership and autonomy. Like, I like actually handing things off, and I think, you know, the, the, the country manager org that I talked about is... uh, has done really well. I think a big part of that is because I've, uh, I've had, you know... I, I couldn't do the job (laughs) , I, I, I handed off and I gave people these, these high level goals, and, uh, and said, "Okay, like, go figure it out." And, uh, I think I've done a really good job giving people a lot of ownership and autonomy, and, and I think that's, that's helped kind of build, build a really good, um, sort of leadership dynamic within the team. Um, uh, and I think it allows people kind of the space to do their best work as well. Um, and I think the weakness is probably, like, the one I was just touching on. Uh, uh, I like to think things through really carefully, uh, but at a startup, you have to kind of trade that off with, with speed as well, uh, and so, uh, you know, and you have to make decisions with imperfect information, and so this is one where, like, I try to sort of counter that by surrounding myself with the right people. My co-founder, for one, has a very different style than me, and so we complement each other really well. Uh, and then I also like to talk to lots of people that, uh, can help, can h- you know, help me think through a decision, and,

23. 49:57 – 50:38

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

    1. SSSameer Shariff49:57

       and I think it lets me kind of get to a- the right answer faster.

    2. HSHarry Stebbings50:00

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

    3. SSSameer Shariff50:03

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

24. 50:38 – 51:20

    If you could be CEO of any other company, which would you choose?

    1. SSSameer Shariff50:38

       that culture, uh, as the business grows?

    2. HSHarry Stebbings50:40

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

    3. SSSameer Shariff50:47

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

25. 51:20 – 52:26

    What do you know now that you wish you'd known when you started Cambly?

    1. SSSameer Shariff51:20

       run that company if I, if I wasn't working on Cambly.

    2. HSHarry Stebbings51:22

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

    3. SSSameer Shariff51:28

       Um, I think, uh, h- hiring in, like, leaders with a, um, with a really, like, deep expertise, uh, in an area. I think, you know, we, we ran a, a good chunk of the company for a long time without, uh, without hiring... Like, we were kind of a team of people that were learning on the job, and I think only more recently have we hired some, some very senior folks, uh, w- you know, we hired the, the head of finance out of Airbnb Experiences, we hired the, the head of core product, um, out of Pinterest, and, and lots of other great leaders onto the team, and I think, uh, that just allows you to move faster, uh, because, um, uh, folks like that can draw from, from the many lessons they've had in their, in their very successful careers and, and bring... inject those things into Cambly. Uh, and so, uh, I think I... if I could go back, I'd say, "Hey, uh, pull in, pull in, pull in some, some really strong leaders with a lot of experience earlier, and, and you'll be able

26. 52:26 – 53:16

    What would you most like to change about startups?

    1. SSSameer Shariff52:26

       to get, you know, get to where you're going faster."

    2. HSHarry Stebbings52:28

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

    3. SSSameer Shariff52:35

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

27. 53:16 – 55:38

    Where will Cambly be in 5 years?

    1. SSSameer Shariff53:16

       comes to, to starting a company.

    2. HSHarry Stebbings53:17

       Final one, 2027, so five years' time.

    3. SSSameer Shariff53:21

       (laughs)

    4. HSHarry Stebbings53:21

       Where are you and Cambly then? Paint that picture for us.

    5. SSSameer Shariff53:26

       Yeah, so, so our mission as a company is to bring, bring really high-quality English to every English learner in the world, and, uh, and, and we... you know, the company's scaled a ton, the company's doing incredibly well, uh, but, but we are very, very far from, from achieving that mission. We've got much, much more ahead of us than behind us, uh, and, you know, 1.5 billion people trying to learn English, uh, we've got only a very, very tiny fraction of them- those people in Cambly today, and so, uh, you know, 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, and there's very concrete things we have to do there, like, um... Cambly's pretty expensive today. I think we have to find ways to make it more affordable and accessible to, to help more people. Um, you know, I talked a little bit about, like, matching. I think matching you with the right tutor is really, really powerful. Uh, that Turkish pilot I mentioned earlier, uh, he found a tutor that had aviation experience, and so he could learn not just everyday English, but the specific English he needed to, to, to communicate with air traffic control, and we have lots and lots of examples like that. And so, matching you with the right tutor is really important and really, really powerful, and so, uh, I, I think we've gotten much, much better at that over the years, um, just with scale, um, uh, but, but, yeah, I think we... I think there's a lot more we can do there, uh, to get you kind of... not just a friendly native English speaker, but the perfect tutor for you. Um, and then personally, like, uh, I just want to grow and learn to be a, a better leader, and, uh, I think we've got some of our most exciting years ahead, uh, and, uh, I think I'll have to work hard in order to, to keep up with the rapid growth of the business. And so, uh, I, I... this is why I'm here. I love, I love learning, uh, and I love new challenges and, and I, I love that running a startup, like, no day is, is, is ever the same, and so, uh, I'm pretty excited about all the new things that are coming over the next few years, and, uh, a- and trying to, trying to keep up and, and scale with the business.

    6. HSHarry Stebbings55:27

       Samit, listen, I love doing this. I, I, I said to you beforehand, I, I had so many different calls and references, and so I felt like I knew you intimately well, um, but this has been such a joy, so thank you so much.

Episode duration: 55:38