Full Transcript for Advice Line with Tope Awotona of Calendly

Our presenting sponsor today is Anthropic, the team behind Claude. Every founder on this show started with a hard question, not the marketing plan, the 2 a.m. kind. Is this idea any good? Am I the one to build it? Should I quit my job? Anthropic got built the same way. A public benefit corporation founded on one hard question. How do we make sure AI goes well for people? So they asked over 100,000 people their hopes and their fears and are publishing what they find, even the uncomfortable parts.

Me? I've got my own hard question about AI. Here it is. If everyone has access to something that can help them write the business plan, build the prototype, analyze the market, maybe even come up with the idea, What separates the people who actually build something from everyone else? I don't have a clean answer yet, so I've been sitting with it with Claude.

There's hope in hard questions. Ask yours at claude.ai.

If you travel often, you'll want to hear about this unprecedented offer. For the first time ever, new Delta SkyMiles Reserve American Express card members can earn two Delta Comfort round-trip flights for travel within the 48 contiguous U.S. states, Puerto Rico, or the U.S. Virgin Islands. Plus, you can earn 50,000 bonus miles towards your next getaway.

And who doesn't appreciate an elevated airport experience? Delta SkyMiles Reserve card members get access to the Delta SkyClub, your pre-flight oasis to recharge, with 15 visits and four one-time guest passes each medallion year when flying Delta together. That's up to $950 in annual value. Value estimate based on $50 per visit rate to purchase additional visits or bring a guest to the Delta SkyClub.

Thank you. Thank you. Hello, and welcome to the advice line on how I built this lab. I'm Guy Raz. This is the place where we help try to solve your business challenges. Each week, I'm joined by a legendary founder, a former guest on the show who will help me try to help you. Joining me this week is Tope Owatonna, the founder of the scheduling platform Calendly.

Tope, great to have you back on the show. Guy, it's great to be here. Thanks for having me. So you were first on the show back in 2020 and you told the story of Calendly. And I have referred to this story so many times because it was basically you started out selling, I think, alarm systems door to door. I remember you said, you know, basically I'd go to 100 doors and if I had a hit rate of one that was successful, I'd make 100.

A commission on that. And I love that story. It's a story of perseverance and persistence and also learning how to deal with people saying no and slamming the door in your face. And that eventually led you to try out different e-commerce businesses and startups that fizzled. But you came upon this idea to launch what became known as Calendly, a scheduling platform that now has, I think, over 20 million users worldwide.

It was, you know, multi-billion dollar valuation. Amazing success. story. And of course, you grew up, you're an immigrant to America. You only came to the U.S. when you were 12 or 13 years old, I think, right? 15. 15, yeah. Before we get into questions for you, Tope, when your episode aired, and I don't know if you know this, but I got mountains of comments on social media, not only on how the story was great, but do you know what the number one comment I got from people was? No, I do not.

It was Nigerians writing and saying, why are you calling him Tope? That is a mispronunciation. His name is not Tope. Can you clarify this for everybody, please? You know, I'm a fan of efficiency and productivity. They are right. Tope is not the proper Nigerian pronunciation. But, you know, I do live in America and most people do not speak Yoruba, my native language.

And so I have anglicized the pronunciation of my name for efficiency's sake. But I'm a chill guy. If I know you're talking to me, I'll respond. So if a Nigerian American or Nigerian meets you, they might call you Tope or not Tope. They might indeed, yes. Okay. I got so much grief. People were saying, this Roz doesn't know how to pronounce a name.

And I said, that's his name. That's what he told us. We always ask for pronunciation. So thank you for clarifying it. I appreciate it. Super funny. Anyway, before we dive into our call, I just want to kind of get an update on your life. I mean, when we last met you, you had not yet done that significant raise that brought the valuation of Calendly up to several billion dollars.

You're still the CEO of Calendly. Tell me a little bit about what's going on in your life, in your world. Yes. You know, almost nothing is the same. Literally almost nothing is the same. So starting with the personal side, at the time, my then-girlfriend is now my wife. Nice. Congrats. And we've been blessed with two beautiful kids that we love and adore.

That's been a massive life-changing event. And then on the business side, almost nothing is the same in tech, right? And that disrupting event being AI. And so just last month, actually, we announced a major launch and a repositioning of Calendly, not just as a scheduling platform, but as a meeting assistant platform. And we're so, so excited about that.

You know, so we popularized this idea of online scheduling, right? That is still a huge part of the business and will be for a very, very long time. It serves a great purpose. But what we've added on top of that is an AI assistant that we are calling Kali. Kali has a lot of different skills, but one of the skills that Kali has is that it can be your scheduling assistant, right? So guy, you send me an email, you say, hey, Tope, let's meet, let's grab coffee.

I can introduce Kali to that email thread and Kali can respond like a human being with my availability. And just like a human assistant, it is really privy to your preferences. It has context on who you're meeting with and what availability you might want to offer them and even the preferences around that. So while the legacy and the classic Kali experience still remains, we are augmenting it with this AI system that's very intelligent and flexible like a human being.

That's cool. It's really cool. You know, I'm sure you get a version of this question and we get it a lot and mainly around building products, you know, not necessarily software. But a lot of founders will say, I don't have access to easy money or to any money. I don't know how to do this thing. I don't know where to go. And of course, you know, they're different pieces of advice you can give somebody.

In your case, I mean, you really finance this business for many years. on savings you had from being an alarm system salesman. I think you emptied your 401k. You worked with a developer in Ukraine, I think, to save money for some time. I mean, you got Calendly to a certain level with really not a whole lot of money. And so when people say to you, these kinds of things can be done without raising millions and millions of dollars, do you think that's true? Or do you think the way you did it is still applicable? It can still be done that way? Yeah.

So I think the punchline is, I think it is possible in certain categories. If you're looking to build a frontier lab, you're going to need billions of dollars, right? But if you're looking to build application software, I would actually argue that the barrier to building software and building technology has never been lower because of AI.

You look at tools like Lovable, Replit, et cetera, et cetera. Anybody with who can write, you know, like, can you produce words? Can you articulate what your requirements are? They can pick any one of these tools and create a product. Yes. Is it going to be the product that skills to millions of users on day one? No, it's not going to be, but you can get your first version out there without a lot of money.

So yeah, The most critical part of building and launching a product is getting to product market fit, creating something that is solving a real problem for people. And I think once you have that validation, the ability to get capital to scale it and recruit people exists. Yeah. How do you think about protecting your business, staying ahead of competition and maintaining momentum as you grow and as you get bigger and the expenses become bigger and the competitors become more fiercer? I think that's one of the things people don't talk enough about business is actually the longer you're in business, it actually gets harder.

And it gets harder because, you know, when you start, you're the challenger, right? And your only goal is to add more and more revenue. There's more to gain. than to protect. And I think we're at a moment in 2026 where the intensity of competition in tech has never been greater. And so those are the reasons why I've, last time we met, my title was just CEO.

Fast forward to now, my title is CEO and CPO, Chief Product Officer. Because innovation is the key to staying ahead in 2026. It's a very, very disruptive time. And I think that the founders have maybe a little bit of a capital within the organization that they can leverage to take bigger bets and move a lot faster and break through some of the bureaucracy.

I hate to use that word. We're a small company. But even then, there are elements of bureaucracy in any time you get people together. Yeah. All right. Tope, are you ready to take our first call? Let's do it. Okay. Welcome to The Advice Line. You are on with Tope Owatonna, the founder of Calendly. Please tell us your name. We're calling from just one brief line about your business, please.

Thank you, guys. Yeah, great to be here. My name's Dom. I'm calling from London in the UK. I'm the co-founder of a business called New Lane, and we make a patented safety-certified folding helmet for the growing number of city cyclists all over the world. Welcome to the show. Thank you for calling in, New Lane. It's a foldable bike helmet, which is a great idea because you could just slip it in your bag, right? And I think probably there are versions of this out there, but tell me a little bit about what is the design? How does it work? Well, I know this is an audio show, but basically it's a clamp at the back.

You raise the crown, you turn over 180 degrees and you fold it and there you have a bike helmet. Oh, so the crown folds back over into the helmet. So it's like thinner. It's like a frisbee. It goes from being a helmet to being a frisbee. And absolutely, as you said, the idea is that much is the same way on a cloudy day, you might put a folding umbrella into your bag in case it rains.

You have a folding bike helmet in there in case you jump onto your own bike, but actually you jump onto one of the numerous hire bike schemes. That's really what we designed it for. That's cool. Yeah. And are you the designer? Well, I'm the chief product officer, but we've used professional designers because my background wasn't in making things.

I was a journalist myself back in the day for the BBC for 12 years, worked as a sports broadcaster, and then moved into nonprofits. And then my co-founder nearly got knocked off a hire bike in central London, didn't have a helmet on his head. He was meeting me and I had my rucksack on the back with my helmet hanging off the back. And he said, can we create a product that will solve both my problem and his problem? So that was 2018.

It took us six years to refine the design and pass the safety standards before we started selling it. So we had six years of, well... It's been persistence. Yeah, it's been grit. And how, tell me a little bit about how sales are going so far. So we launched the product into the market in 24, almost exactly two years ago. We did about, I'm doing the talk in dollars.

We did $650,000 in year one revenue. We're approaching a million dollars in revenue of this year. So we're getting somewhere. The honest truth is profitability is very challenging. And we make it here in the UK, which is unusual. Most of these kinds of products get made in the Far East. So we're making it here, which you could argue is we're making it difficult for ourselves.

But we want to have line of sight. We want to control the quality of it. Is most of your sales are direct to consumer or through bike shops? Most of them are direct to consumer. We have a pretty good Shopify site, which we use and we go through social media advertising. We are about to sign a distribution deal with a pretty significant UK and European distributor.

truth be told, this is really why I wanted to speak to you guys, is that we've got to a really, really strong inflection point where we're in a really good position. But scale and growth is challenging because paid media is really expensive and becoming more so, it seems to me, for whatever reason, all sorts of reasons. And distribution is challenging because of the margins you have to give away to the distribution network and to the retailers.

So we're trying to work out how we scale as we try to become more profitable and try to grow. And it's a really tough challenge. All right, Dom, I want to bring in Tope here. Tope Owatonna, please meet Dom. Thoughts, questions, ideas for Dom? Dom, nice to meet you and congrats on building a great product. Thank you. Just a few questions for you.

So who are your customers? Who's buying the product? And you mentioned that the primary channels are digital and direct to consumer, but can you give us a sense of margins? Because that seems to be one of the constraints you have in terms of being able to scale your customer acquisition methods. Yeah. So customers, essentially city riders who either commute into London from outside of London, predominantly our market is London because London is huge and cycling has really kicked off over here in the last three or five years.

Line bikes and regular bikes, they're all here and it's gone. So we're talking about Londoners, we're talking about people who use bikes to go from A to B rather than sports cyclists. We're talking about transport cyclists or the functional cyclists. And the demographic of those people is pretty broad, to be honest, men, women, young and old.

Margins, well, I mean, the gross margins are pretty healthy. So we sell it for £100 and we have an upgraded version, which we sell for more. But when you pay a distributor... We pay a retailer 40%, and we pay a distributor somewhere near 35%, 40% of what's left, and then we have to see what we can make out of that. But margins, we can make them better by increasing the price or trying to drive our prices down, but that's challenging.

I'm looking at this. First of all, your prices, at least in dollars, I'm sure it's the same in pounds, are great. I mean, I'm a cyclist. I've got a bunch of helmets. You've got a MIPS helmet, which is an extra layer of safety for $176. We're the only folding helmet to have that on the planet. I mean, that's a really good price for a high-quality helmet.

The thing that is kind of amazing to me that you mentioned and that is not clear, at least on your website, this is a UK-made product. And I feel like if that's a selling point, you should push that. Mm-hmm. Or you should make it abroad and you should cut your costs. Sure. Yeah. We've thought about that. We have discussed taking it to the Far East.

The problem is we've gone so far down the line. We have a great manufacturer here. The cost of moving all our tools is pretty heavy. And with the world being what it is, the geopolitical landscape is also slightly challenging here. Well, maybe you should lean into the made in the UK for now. I mean, I feel like that's worth a lot. I mean, that's a premium right there and then.

You're paying for really high quality product, probably very skilled manufacturers. So that's one thing. Tope, I have a question for you because... You came up with an idea for people who you knew who you were going after. It was like people who just didn't have the money to have a full-time assistant or even a part-time assistant. To me, this seems like a product really made for commuters, right? For everyday cyclists.

Obviously, neither of us are experts in this particular lane, but how would you even think about, if you should think about, really reaching that specific type of consumer? Yeah. So I have a lot of different thoughts on this. So I have a few bikes. I have two bikes and I have one helmet, but I only have the helmet because my wife is, my wife really loves me.

And my wife insisted that I needed to get a helmet just this past, I hadn't worn the helmet in many years, actually. So just this past one day, biking with my kids, they didn't want to wear their helmets. And so I had to wear a helmet to set a good example for my kids. Yes. And so maybe what I'm trying to get at is like, there's the writer, but there's maybe like the actual maybe buyer or the person who's influencing the writer to buy that helmet.

And I wonder if there's an opportunity for you to, is there like a gift and flow on your website so that, you know, my wife gets, you know, an ad for New Lane and then she goes on the website and she can easily like, you know, buy for- Protect your kids. Are they wearing a helmet? Right, exactly. Yeah. And, you know, there's just more, you know, generally more opportunities to market directly to those people.

So that's one thought. The other thought is when I go on your website, I see that you're sort of like your main pitch is this is the helmet that works around your life, which I think is great. But I wonder if there's an even bigger objection that you are facing that is maybe not a physical one, but maybe a behavioral one, which is that. Many people are buying helmets, but they're not using them.

Or many people are not buying helmets in the first place because they don't think they're going to wear them because they're a pain in the neck, right? And so is there a higher level thing you can appeal to around this is the helmet you're actually going to use? It's an interesting thought. I mean, it's fantastic points. I mean, and to be honest, the conversation we're having here makes me realize we've got to lean into both those points very strongly.

Gifting is really important because people on line bikes The mothers of the riders or the husbands of the riders are the ones. Exactly. You know, and 20% of our sales in gifting season last year were not, they were bought by people for other people. To the people you're going to use them. Super interesting. It was very significant for us.

Yeah. Calendly. The way we grew, just like you, I didn't really have the ability to pay a lot for customer acquisition. And so what really we created instead was this virality, right? Every time you use the product, you introduce other people to it.

Obviously, in software, we did it through virality. I don't know what the physical equivalent of that is. But is there a moment in which, sorry, at the risk of talking about myself too much, but I own this classic Defender. It's a 97, Defender 90. I love it. It's one of my favorite material positions. And I can't drive that car without people asking me about it.

And you have this very, very interesting product, right? Is there an opportunity to think about when I use this product, when it's folded, it creates this conversation and people want to know where I got it and they're also interested in it. I don't know what it is, but I wonder if there's an angle for you there. Because it's such a unique product.

Yeah. It's awesome. Well, the product is called New Lane, the only foldable helmet made in the UK. It's really cool. Dom Cotton, thank you so much for calling in and good luck. Thank you.

This is the Dyson of bike helmets. It's so cool. It's so, so cool. You know, we do huge brands on the show, like multi-million, multi-billion dollar companies on how I built this. And then we do the device line. You know, we're talking to smaller companies that are doing some $10,000 a year, $200,000, if they're lucky, a million. And here you go.

You know, it's like a reminder that there's so many cool products out there that we just don't know about yet. This may be a controversial thing to say, but...

I think this is also a good deal flow pipeline for a potential investor. I agree. Like I'm thinking about reaching out to Dom. I mean, I don't do it. I don't make the investments. I'm just here putting it out there. Maybe I should get paid like a commission from listeners. Maybe you should. I think I'm going to reach out to Dom and yeah, I really am.

Absolutely, you should. And by the way, anyone who does that, if you want to send me like a commission check, happy to take whatever the going rate is. Do I get one in turn as the one who suggested the idea as well? Yeah, absolutely.

Okay, next up after the break, another caller with another business challenge. I'm Guy Raz, and we're answering your business questions right here on The Advice Line on How I Built This Lab.

Stripe is built for whatever comes next because the pace of change has never been faster than it is right now. New business models, new currencies, and new expectations for speed, reliability, and scale. Stripe builds financial infrastructure that helps businesses start, grow, and operate globally. From payments and billing to fraud protection and cross-border payouts, Stripe is built to support the new pace of commerce.

They're trusted by the companies building at the frontier, from 86% of the Forbes AI50 to global leaders like Salesforce and OpenAI. In fact, more than 1.6% of global GDP flows through Stripe, with Stripe's users processing a combined $1.9 trillion last year. So if you're already thinking about what's next for your business, see what's possible at Stripe.com.

Hi, it's Phoebe Judge, host of Criminal. I'm going on tour. If you like hearing me tell stories about people, well, I've decided to tell stories about my life and the people I love. A letter was left carelessly around, so I was sort of caught red-handed. It's a show about secrets and forgiveness. I hope you'll come see it. Find all our tour dates and get tickets at thisiscriminal.com live.

Welcome back to The Advice Line right here on How I Built This Lab. I'm Guy Raz, and my guest today is Tope Owatonna, founder of Calendly. And Tope, you ready to take our next call? Yes, I am. All right, let's bring in our next caller. Please tell us your name, where you're calling from, and just one brief line about your business. Hi, Guy and Taupe.

I'm Ivana. I'm dialing in from Vancouver, Canada, and I'm the founder of Playfield. We make human-centric products for pet lovers. Awesome. Welcome to the show, Ivana, and thanks for listening in Vancouver. Human-centric products for—I'm a pet lover and a human. I'm a human who loves pets. Tell me what you make. Yeah, so our hero product is the Bailey Kit, and it's a modular, multifunctional dog walking bag and treat pouch combo.

Nice. So I have one that's ugly, and I'm like, I don't even know what the brand is, where I put like, I got dog treats in there, and I got poop bags in there, and I've got a ball in there for my dog, you know, to distract her sometimes if another dog comes and they want to just go at it. What is, describe what it looks like and how it fits.

Yeah. Yeah. So it's designed to look really sleek, right? So sometimes it's very unassuming, but we have a built-in poo bag dispenser in the back panel. We have, what's unique about our product is this hidden retractable water bottle pocket. It's actually helped us go viral on social media a few times. People love being able to just expand it so they can carry water with them without bringing a backpack.

You can attach your leash to the D-ring on the bag. We have compartments for your keys, credit cards. It's a design I came up with because, like you, I had a different... bag before that I was kind of using to carry all my things, taking my dog out for walks. But I'm just with her so much throughout the day that I, you know, why would I trade in the dog walking bag for my everyday bag and back and forth if I could just have everything in one well-designed product that I could also use when she wasn't with me.

Awesome. Okay. And tell me a little bit about how the business is doing. You've launched when? And tell me a little bit about your sales so far. Yeah. So we launched in April 2024. In our first full year, we did a little over 200,000 in sales. Fantastic. And then this year, we're probably on track, might come a little under that for reasons I'll get into.

Yeah. Tell me why. I mean, I'm assuming it's mostly direct to consumer, but why are the sales flat? Yeah, so we are primarily direct-to-consumer. We're also in Chewy and a few independent pet boutiques. We're also launching in a nationwide retailer in October. But the reason why it hasn't been a growth year for us is because... I'm actually eight months pregnant right now.

So that was something that sort of knocked me off my feet. As a solo founder that's bootstrapped the business, I think it was certainly a catalyst for me to think about what needs to change. I've been doing everything myself. We do have, for context, we have a fulfillment center in Arizona. I've just recently brought on a social media agency about a month ago to help us with content.

So I'm starting to outsource things, but I think this leads well into my question, which is really around knowing that I'm about a month away from giving birth to my first child. What are some systems I should really think about building so that The business can still continue without me doing everything. And, you know, what should I be delegating or how do I think about this longer term? I love that question.

Thank you for it. Topo, I want to bring you in here. I mean, sorry, I just broke my mic, but I'm just going to hold it. I think.

Ivana, congratulations on your first child. Big, big, big, excited moment. Just maybe just a few questions for you. So you mentioned the Fulfillment Center and you mentioned the social media agency that you just brought on. But do you have any other people helping you in the business today? The only other person who I also have just brought on as of this week is a freelancer to help us run our ambassador program.

But besides that, that's pretty much it. I do all product design, customer service, all the logistics with our manufacturer overseas. So pretty much like everything still falls in my lap. Got it. Do you have any thoughts on who runs the business while you're out? Or is it you pushing out a baby and then responding to customer emails? I know it's not ideal, but I'm like, I think I'm bringing my laptop to the hospital.

Oh, no. I know. I do want to be present too, right? When the baby comes. And I know this is such a beautiful chapter in our lives, but it's also the start of Q4. So it's just a crazy, crazy timing. The Christmas time. First thing I just want to say is I, you know, people are going to interpret this in different ways and people have their own views on this.

There is nothing, nothing I've done in my career, 30 years of my career, nothing that is remotely as fulfilling or important or meaningful as being a dad. And even when my kids are teenagers now, they don't want to talk to me. You know, the door is closed. You know, they're doing their own thing. It's everything to me. And so that's just– I'm just going to leave it there.

But now I want to say something else, which is we had an episode on the show a couple weeks ago. You should listen to it, Bog Bags. Kim Vaccarella started this brand. It is now– they're doing over $250 million in sales a year. She started it on her own, bootstrapped it. It's basically a bag that's made out of the material that makes Croc shoes.

It's a beach bag. And she started it in like 2010, 2011 and got some momentum, you know, probably got it to about where you got your brand. And then there was just a disaster with her manufacturer and she lost like $30,000, $40,000. So she stopped. She just shut down the business for two years. And what happened was people started to ask her what happened to these bags.

And that inspired her to restart it in like 2013. Wow.

And she reconstituted it and went back full force, and it is what it is today. So I just want to use that as an example of a brand that put things on pause. I'm not saying that's what you do, but if you have to, it's okay. It doesn't go away. It's still there, and you can still come back to it if you take three months or six months or whatever you decide to do.

That is also okay. Thank you for saying that. But Tope, let's just do some nuts and bolts stuff here. Let's say, okay, Ivana's got a limited budget. If she was going to allocate some of her resources, right, let's say even a part-time person, what should she think about? What kind of person should she potentially look for? Yeah. I have one more question before I answer that.

What do you think is the most important job while you're out? Is it keeping the lights on? Is it, you know, you have this major retail partnership that's about to kick off. Is it really nailing that and making that as successful as possible? Assuming you could only pick one of the two, right? Just like, which would you pick? I think the good news is most of the things are in motion already with the retail launch.

So I do think it's primarily just keeping the lights on. As an ambitious person, it's hard to say that where you're like, I really want to grow this year. But yeah, I think just keeping the lights on, moving inventory, any like future product development I've kind of punted to next year. But even then, right, like I'm not sure. just how much free time I'm going to have once the baby's here.

So I think even some advice from two fathers, you can give me a glimpse into what my future, early future might look like. Well, this might be blasphemous to say, but...

You know, having your first child is brutal, especially as the mother. But then also, I think one of the things parents always struggle with is, you know, losing sort of like their own individual identity as they become a parent. And so you might actually find that, yes, you want to be a great mother and you want to make sure your child is taken care of.

But, you know, I can tell you from personal experience that Being able to maintain your individual identity, I suspect is going to be really, really important to you after the baby. And you may find that going right back into play field at whatever level you want to is going to be a huge part of that. I kind of think so, too. I get that inkling.

Yeah. I'm just going to offer a flip side, which is I didn't care about my identity. I was happy to be called dad for it. Like, I don't care how I built this house. It doesn't matter. But no, but I hear you. Here's another. I know now this is turning into like a parenting, a marital advice show. And maybe maybe we should do that. I should start it.

I'm down. The point Tope made is really critical. It's going to be an amazing time to see this little human. It's just so special. It's really hard. And there's, you know, you're not going to get a lot of sleep and you're going to be tired and overwhelmed. And somehow then a lot of people just forget it and have another kid. But it is, you know, the challenge is, of course, worth it.

And so, again, I would say that, you know, Give yourself grace. And if you don't, and you said another thing, which I think is really important. You said it's hard for an ambitious person not to expand the business right now. You are ambitious. This is going to succeed because you are motivated to make it succeed and to make it grow. And so it may mean that you put the brakes on for a couple of months.

And it may mean that this quarter, it might not be what you want it to be, even though it's a Christmas quarter. Yes. But that's sort of like, That's what fate handed you. The baby is going to be born in the quarter before Christmas. And OK, you've got next year to ramp up once you've had some time to get all your home systems in place. Totally fair.

Yeah, I'll throw in a few, you know, maybe more pointed advice then. So I think the most important thing is keeping the business afloat. If the business is afloat, you live to fight for another day. And I think you've already identified kind of like the skills that are most important, the person that you need. It's operational excellence.

There's a lot of, you know, things that happen on a day-to-day basis and the trains need to keep on running. And I think the fact that you've identified that I think is also telling. And actually also mirrors my experience with Calendly. So Calendly, When I started Calendly, my first employee was an engineer. And the next hire that I made was a marketing person because I thought the thing we needed to do was grow the top line and increase demand.

But what happened in our case is that the virality in the product took off so much that marketing was not the bottleneck. It was servicing all these customers that were coming into our product. And so this marketing person that I hired quickly, you know, pivoted to a customer success person because we needed these customers to be successful.

And maybe like what I'm trying to say is like a lot of times as a business owner, you have all these ideas of I need to scale this next. I need to scale that. I think what you're going to find is like something is clearly going to be broken and it's going to be so obvious the next thing you need to go automate. And I think in your case, it sounds like it's the operations part of it.

And I think that would also give you a lot of relief once you come back and you can focus your I know your energy and your intellect on thinking big and on product and growing revenue and all these different things. I think you're totally spot on because like, you know, with the pregnancy being this catalyst to force me to think about things, I also did a bit of like a delegate, elevate, you know, just kind of figuring out the whole quadrant system of where I want to spend my time.

And I was realizing so much of my time was being sucked into the operations that I haven't been designing new products and I haven't been able to do the brand building, the bigger strategic partnerships that really get me excited. So it was sort of this like, okay, I'm faced with a very real reality of I'm not going to have a lot of bandwidth in this short period of time.

But when I do come back, it's making sure I do have the right people in place or the systems in place or to your point, automating things so I can have more time back to do the things I really enjoy. For sure. Like those are things that like, I think it's much easier to find somebody who can make the operations run smooth than it is to find somebody who can think about brand, who can think about products and the intersection of all that.

And that's you, like that's you. You're the only person who can really do that. Ivana, before I forget, do you know the baby's gender? I do. We're having a boy. Congratulations. Boys, really easy. Harder than girls as babies, but you will be so happy when that boy's a teenager, as are we. Much easier than girl teenagers, from what I understand.

I always tell my parents, I'm like, I was a good daughter, though. I was easy. You know, I was an easy girl. Yeah. Well, congratulations. I'm so happy for you. The brand is called Playfield. Ivana Tay is the founder in Vancouver. Good luck. Ivana, best of luck. Thank you, guys. It means the world. Um... Yeah, it's like, you know, things just happen when they're meant to happen.

And sometimes the timing is tricky and that's OK. You know, if you live long enough, you're going to have challenging moments. And at the time when you're dealing with something, because it feels daunting, it feels impossible. But with the benefit of hindsight, that thing seems so trivial. I can think of many things that at that time I was like, man, how am I how are you going to get through this? How are you how do you ever go on? But then you look back at that thing, you know, many years after the fact, and it just it seems trivial in the grand scheme of things.

All right, we're going to take another quick break, but we'll be right back with another caller. Stay with us. I'm Guy Raz, and you're listening to The Advice Line right here on How I Built This Lab.

Welcome back to The Advice Line right here on How I Built This Lab. I'm Guy Raz, and my guest today is Tope Awotana, founder of Calendly, and we are taking your calls, and let's bring in our next caller. Hello. Hey, Guy. Hey, Tope. Thanks so much for having me on. I'm super grateful to get to chat with you guys today. My name is Dani, and I'm the owner of a boutique-style nail salon in Greer, South Carolina, called The Nail Room, where we are trying to end the cycle of women being made to choose between Healthy natural nails and a beautiful long-lasting manicure using our signature techniques and a product called Builder Gel.

All right. Welcome to the show, Dani. The nail room. Okay. I'll admit, I have had, never had my nails done, but I've had a pedicure before. Okay. It was an amazing experience. So what happens when you go to the nail salon, normally the choice is between like what and what? So kind of the way it's typically done now is you go into the nail salon and they'll glue on artificial tips to your nails and they're just not natural.

And when you come back in, they have to soak them off using chemicals like acetone, continually thinning and damaging your nails. So our approach is we use a product called builder gel, which is just a clear thick gel that you apply to the nail and it strengthens it. You paint it. And when the client comes back in and wants them redone, You just remove the color, fill in the new growth and paint them again.

So you never have to soak off. Okay, cool. That's awesome. All right. So you've got this different way of doing nails so your nails don't just disintegrate and fall off. And by the way, where is Greer, South Carolina? It's in Greenville, South Carolina. It's in the upstate of South Carolina. I got it. Okay. And tell me a little bit about the business.

When did you launch it and how is the business going? So we opened four months ago. Oh, new, brand new. Yes. And our gross sales to date, we just hit $100,000. Congrats. That's awesome. Thank you. And had you worked in this field before? Because this is your business. Were you a

manicurist before and decided to start your own? Yeah, tell me a little bit. So I was a stay-at-home mom for five years. I have three little ones. And after we had our third baby and we knew we were done, Well, I had started many businesses from home and then stopped them. And I think I always just, um, had the entrepreneurial spirit. And so after we had our third, I told my husband, I was ready to really hunker in and do something.

And I had been doing my own nails at home and I've always been artistic. And he actually encouraged me and said, I think you should attend nail school. And cool. Yeah. So I looked into it and it was simple enough and I went and I started doing nails out of my room in my grandma's home actually. And just based off of the signature technique I was using and the product I was using, I had to close my books within a couple months working out of a studio at my grandma's house.

So my husband and I kind of thought, is this something we could just duplicate in more girls and start a salon? And we did. And the demand was there and it's taken off since. And do you have other, do you call them stylists? Nail technicians. Do you have others working at the salon? Yes, there are six of us. So are you even doing nails anymore yourself? I do nails.

I see six clients a week only so that I can spend time with my kids otherwise. And the business, running the business a lot. Yeah. Yes. All right. Before we dive in further, what is your question for us? So naturally, like everyone else, I do want to know how I can take the success we've seen on a small scale and translate it to a big scale.

But however, maybe even more so as a wife and a mother of three kids, I also wonder, even if you know you can and the market's there, how do you know if you should and if it's right for you, your family and your marriage? to grow, to scale? Like, what would you like this to be in your dream house world? I would love... Honestly, I'm very inspired by Allie Webb of Drybar and what she's done with Drybar.

I would love to see the nail room be comparable to that and see many locations and see it be a new accessible nail salon, high quality nail salon. That's cool. I love that. Okay. You should reach out to Allie Webb, who's, as you probably know, was on the show several years ago. Tope, I want to bring you in. Please say hello to Dani, the nail room.

Hi, Dani. Hey, Tope. Hi. I don't know. Have you had a manicure or pedicure before? I have. Everyone's going to hear this, right? Everyone's going to hear it. I've had one. I've had a pedicure. I love it. I have. I do it with my wife. It's the best. Yeah, yeah, it is. Yeah. That's great. We have a lot of men that come in. We actually offer a pedicure called the manly pedi.

And it helps that they have alcohol. Yes. Oh, nice. Yeah. I mean, so, all right. So, I mean, there's this vision, a dream, a sort of a dry bar of nail salons. I think there are a couple of sort of national chains, if I'm not mistaken, like Regal Nails is one that I can think of. So, Tope, what do you think? I mean, how should somebody like Dani think about her next move? Yeah.

So congratulations. I mean, the growth that you've had in a short amount of time is really, really impressive. I think maybe the things I'm trying to understand is the business that you have today, how full are you, right? So if you have six technicians, assume you are open 40 hours a week, and that's roughly 240 shift hours. How full are you within those full hours, within those 240 hours? We are extremely, extremely booked and we're constantly getting complaints that we don't have more openings.

So it has, the demand is far surpassing what we can meet at this point. That's fantastic. And you are, you're profitable? Yes. And does this business scale without you? When you look at the business today, like what do you feel like you have to be involved in versus, you know, what do you feel like happens automatically whether you're there or not? I feel like at this point, We've definitely started, I feel like, doing a good job of we have a manager in play, we have an assistant in play, and that helps a lot.

I would say, honestly, probably a lot of the numbers and making sure that our costs aren't too high and, yeah, making sure that, you know, the times are short enough for services that we can fit enough people in in the day to, you know, make it profitable and everything. So really, I think the numbers is where I think I'm feeling like I have to spend a lot of time watching and making sure it's all going correctly.

Okay, a couple of thoughts here. I love that you're thinking of AliWeb and Drybar because that is a really interesting model to think about. And in this space, again, I'm not super familiar with it, but it seems to me that there's an opportunity to do something elevated, almost like a luxury. Now I know where you are. You're in an interesting part of the country because...

even though people might not know a whole lot about Greenville, there is a huge BMW manufacturing facility there. And also a lot of international people who are BMW executives in that area. So I'm thinking, I love the idea of dreaming big and imagining what it could be like. And you've got a technique. And yes, you can replicate it. But I don't think the technique is enough to get people into the door because I'm sure there are a lot of nail salons around the country that do this technique.

And that's not the differentiating factor to me. What is going to make this business different– and I think you really need to hone in and perfect it at this salon– is to focus on experience, not just how your nails are gonna look and how beautiful they're gonna be and healthy. That's great, but how are you gonna feel when you're there? Are you gonna get a glass of champagne? Are you gonna invest in a little espresso maker and offer a little espresso? Or even something like, can you bring your kid in And somebody will watch your kid.

I know I'm not saying just interesting, innovative ideas that create an experience for people like, oh, the nail room. That's what Drybar did. Yeah, I love that. And we do actually offer craft lattes when they come in and they change with the season and. People genuinely come in inside and they're like, I've been looking forward to this latte all day.

So, yes, we are. We're tapping into the luxury experience experience. And because the gel technique like not everyone's doing that, I agree. But that's replicable. You can't replicate a feeling. It's not easy. And if you really make people feel like they're getting more value than what they paid for, that's a game changer. I think you're absolutely right.

So, I mean, let's take my wife, for example. My wife actually has all this equipment. She does her nails and she does it so well that one time she went to a salon and they wanted to hire her. Wow. Which is kind of similar to your story. But at the end of the day, when she has all the equipment, why did she go to the salon? I think that ultimately has to do with experience.

So, Guy, I think you're absolutely right. I think the other part of your question, Dani, is should I expand and how do I go about it? And I feel like it's ultimately a personal question. Only you can kind of answer that question about how big it should be. I think you're going to be successful regardless of which path you're already successful and you remain successful regardless of what you do.

But I think it comes with a lot of sacrifices, right? I don't get to hang out with my friends as much as I would like to. I'm not a great cousin or brother at times. Those are sacrifices that I've made. But on the flip side, the financial sort of rewards of Calendly have allowed me to impact a lot of people in a lot of different ways. And that's something that I'm proud of.

Absolutely. I think you just have to look at the pros and the cons and make that decision ultimately for yourself. And as you're thinking about expansion, given that you're already full today, I'd be more inclined to think about how do you get a bigger location and get more revenue out of each individual location first, maximizing revenue per store before you think about even the second store.

Yes. Yeah, exactly. And once once you've got things down at the first store, then you start with one store and you do that for a year before you go to store three and you go to Greenville, downtown Greenville. Right. You go from. Yeah. And then maybe then you go to Charlotte, you know, only. But you really start really local. That's such great advice.

Danny Sarkella, Nail Room. Thanks for calling in. Good luck. Thank you so much. Thank you. Yeah, I have not had a pedicure in a long, long time. I need to go back. It was a nice bonding experience with my wife. We're sitting in those chairs and, you know, your feet are in the bath and it's nice. It's very nice. I'm due for one with my wife.

It's a great day date. Yeah, maybe we should. I'll go to Atlanta. We should do like a double date. Just sit in four chairs and get pedicures. Let's do it.

We're going to take a quick break, but when we come back, another caller, another question, and another round of advice. I'm Guy Raz. Stick around. You're listening to The Advice Line on How I Built This.

Welcome back to the advice line on how I built this lab. I'm Guy Raz. All right, let's bring in our final caller. Welcome to the advice line. You're on with Topo Watana, founder of Calendly. Please tell us your name, where you're calling from, and just a line or two about your business. Sure. Hey, Guy. Hey, Topo. My name is Justin Kittredge from Boston, Massachusetts.

I am the founder of iSlide. We are a premium customized footwear company focusing on slide sandals, slippers, and socks. Awesome. Welcome to the show. Okay. Slide sandals, slippers, and socks. And what, tell me a little bit about what, are they designed differently? What makes them unusual? So the biggest thing about them, the slides themselves are customized.

So almost no one does customized slide sandals. So it's the slides that you think of like kind of going to and from a basketball court or football field, baseball field. I don't want to say like some of these bigger brands, but like they're very similar looking. But our biggest thing is it's all customized one period of time. Customized meaning what? There's what, like a branding or a corporate customization or what? You can do anything.

So we have licensing. So we have NBA, MLB, NHL. We do local teams. We have over 100 colleges. We do brands. We do companies. We do, you know, anything that you want, we actually will customize the logo on it. So I could do like how I built this slides or slippers. You just upload the logo and you print them out. 100%. Tell me a little bit about the business.

When did you start it and how is it doing now? Sure. So we started the company 13 years ago. Okay. We've grown 12 out of 13 years. However, we've experienced only slight growth these last few years as we've really just focused much more on profit. But as we look into the next few years in higher growth mode, we're struggling of where to focus, mainly because we sell into so many different channels.

And we have so many different types of target consumers that we actually that will buy our product. So as we kind of get back into growth mode, it's really just trying to figure out, you know, instead of trying to do a little bit of everything, are there some certain channels that we really should be focusing on? All right. That's your question.

Just for context, roughly what are your annual sales? About five and a half million. And this is all direct-to-consumer? No. We actually don't focus on our website sales a lot. We really focus on four different channels. So our e-com is our just sole direct-to-consumer. We do have traditional wholesale. So we will sell into brick and mortar and even some other e-commerce sites that will take our product and then resell it just on their own site.

um we do direct to like teams that's like that bulk ordering that and that could be for a team that could be a company outing that could be for a brand that is going you know that just wants to buy a lot at one time and then lastly which kind of falls in between this wholesale direct-to-consumer is we do a lot um and we're growing our business within the dropship model so basically a company like fanatics They might have a thousand of our different teams of our slides on their platform.

And we'll bring all those sales in to go right into our kind of printing process center. And then within a couple of days, we'll print them and ship them to those all these different consumers. Got it. OK. And so you're doing about five million sales and you're looking, I'm assuming, to expand to get to sort of maybe break through to 10 or even more.

Yeah. I mean, I think for us, 10 is that next kind of plateau that, you know, kind of goal to strive for. How many employees do you guys have? Today we have 10. Okay. 10 employees. All right. I want to bring Tope in here. You've been there. You were, you had a business that was doing a few hundred thousand or, you know, less than that. And then you had to grow it.

And then 10 million is a, it is a really significant milestone to reach that number. It's hard. How do you break through? How do you get to that point? Yeah, Justin, congratulations on the business you've built. I started Calendly 13 years ago, so we have that in common.

In general, I'm a fan of the Apple model, which is like the fewest products you can have that generate the most amount of revenue. So I'm a huge fan of focus and getting leverage through that. But as you think about the different channels and different products, are there some that have stronger metrics on repeat orders, on average revenue? Are there parts of the business that you're more excited and more passionate about than others, for example? Yeah, I love our licensed business for sure.

But I really do love our directed team model, right? And again, we will sell to pro teams, college, high school and youth. So they have the hat, they have the jersey, they have everything with their logo on it. But they've always just worn like a regular Nike or Adidas type of product. Now they can have the full head to toe. So I really do love that.

those two elements i think the part for us it's funny that like i would love to focus more but then you look at things that have happened in our in our career like covid where our e-commerce businesses if we didn't have them there was direct-to-consumer and dropship models like absolutely took off and was amazing where wholesale and brick and mortar was dead and And then the following year, you see some of that econ business kind of take a fall and the other parts of our business actually like thrived.

And I think the thought of getting rid of one or two was just kind of like the scary part of like, well, if I did and something else happens, I mean, we could have been out of business, right? Like during COVID or maybe even the year after, depending on the channels we had. Yeah, I think you're absolutely right. I do think that, again, generally speaking, right, within every business, there's going to be an inflection point.

The things that got you from zero to one are going to be different for the things that got you from one to $5 million in revenue. And I think likewise, going from five to $10 million in revenue will probably require some fundamental, will probably require some trade-offs, right? There's this guy, Naval. He's a sort of philosopher. Naval Ravikant, right? Yeah, exactly.

Of Angel's List, or what it's called. He had this really profound quote. And what he said was, a happy man has a million wishes, but a dying man has one wish, which is to live. And you know, your business is not in any way dying, but if you, and it's not gonna die, it's doing great. It's been around for 13 years. But if you were to kind of approach the problem from that standpoint of like, I have one goal and that goal is to get from five to $10 million, it might force you to make some trade-offs.

Because I think right now you both want the diversification. I think you can have diversification while also looking to grow the business. Maybe you have four different products, an X number of channels. Maybe you don't scale all of them down, but can you gradually begin to bet on one or two of them and put 80% of your time and effort in those? You as the CEO and founder don't even spend your time on the channels that are deprioritized.

Yeah, I mean, I think that, you know, it's a big question and it's a very hard question to answer. And there are many, many different ways to answer it. I mean, you know, part of that can be answered by efficiencies, right? And how you source. But some of those things you may not want to change, right? And so I'm not sure whether it's selling into too many channels.

I mean, to me, selling into lots of different channels is a good thing to be doing. But of course, you want to be more efficient about the order sizes, right? But better to sell into... 20 channels with big orders than, you know, 300 channels with tiny orders. Right. Fair enough. Right. And I'm assuming that's what you're looking for. You're looking for bigger partnerships.

Absolutely. I mean, some of our, you know, we talk about the drop ship model, even some of the wholesale, you know, that we have, those are great partners that are consistent sales coming in every single day. And it's like, okay, yeah. How do we find more like that in our target demographic group? Yeah. you know, we are trying to lean more into AI.

And I think, you know, by doing that, that might, you know, from a sales outreach and kind of communication back and forth, it could go, you know, a really long way. Just kind of a little bit what Tope was saying in the beginning about, you know, he can have his AI assistant just all of a sudden now come on board and set, you know, and set these meetings.

Exactly. We are trying to lean into that a lot more. And We have great sales reps now, but imagine if those sales reps that we have could almost be doing 10X what they're doing now because of how much easier we can make their life through AI. Yeah. Awesome. Justin Kittredge, the brand is called iSlide. Thank you for calling in. Good luck.

All right. Thanks, guys. Thanks, Tope. All right. Thank you. Take care. All right. Bye-bye. Taupe, Taupe, Taupe, you have been very wise. Your advice is incredibly helpful. But before I let you go, I do want to ask you a question about you, which is, you know, when you started out, there are a lot of things you know that you now know running a huge business.

If you could go back to you when you were starting Calendly, you know, that guy in Ukraine or whatever, what advice do you think you could pass on to him, to the younger Taupe now that might have been helpful? I think what I've learned 13 years in is you build a business around a customer and not a product. I think that entrepreneurs, first-time entrepreneurs who are still kind of learning, they have a tendency to think product first.

But I think, I now think customer first and it's really what's sort of guiding us in this moment when we are expanding our product. So once you acquire a customer and you're servicing them really well and you've created a brand for them, it is a lot easier to expand with that existing customer type than it is to go try to expand the different types of customers you serve.

And ultimately over time, you need to do both. But maybe that's the biggest thing I think about differently 13 years on. That's awesome. Tope, thank you so much for coming back onto the show. Thanks for having me. That is Tope Awotana, founder of Calendly. And it is pronounced Tope. It is pronounced Tope. It's pronounced Tope. And by the way, if you haven't heard Tope's original How I Built This episode, please go back and check it out.

Really, it's so good. It's such a good episode. There's so much to learn from it. You can find a link to it in the podcast description. And here's one of my favorite moments from that episode.

How much was it going to cost you to get this prototype built? A little over $200,000 is what we thought it would cost. Wow. So I had to empty every single dollar in my 401k, use every single dollar in my savings account. I had to borrow a little bit on top of that. I ended up borrowing a little bit from Linden Club. At a high interest rate? At a very high interest rate and maxed out all my credit cards and put it all in on this idea that at the time didn't even have a name.

Hey, thanks so much for listening to the show this week. And by the way, please make sure to check out my newsletter. You can sign up for it for free at GuyRoz.com or on Substack. This episode was produced by Alex Chung with music composed by Ramtina Rablui. It was edited by John Isabella. Our engineer was Anli Huang. Our production staff also includes Carrie Thompson, Carla Estevez, Casey Herman, JC Howard, Sam Paulson, Chris Messini, Catherine Seifer, Neva Grant, and Elaine Coates.

I'm Guy Roz, and you've been listening to How I Built This.