Calendly: Tope Awotona (2020)

Hey, it's Guy here, and I hope your new year is off to a great start. On today's show, we have an episode from the Archives. It's about a founder who could not come up with a compelling business idea until one day He tried to set up a meeting for 15 people, and he realized that is a really hard thing to do. And from that Callanley was born.

It was an episode that first ran back in twenty twenty. And I hope you enjoy it. Oh and one more thing, just a quick note on this episode. Tope Owatana's name is pronounced Taupe. That's how he pronounces it, and I know some of you from Nigeria think it might be pronounced Tope. Nope, he pronounces it taupe. So Without further ado.

Here's the show. How much was it gonna cost you to get this? Prototype built. A little over two hundred thousand dollars is what we thought it would cost. Wow. So I had to empty every single dollar my four one K. 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 uh On this idea that at the time didn't even have a name.

Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements. They built. I'm Guy Raz, and on the show today. how Tobawatana turned his frustration with scheduling meetings into calendarly.

A multi-million dollar business that makes setting up a meeting Quick. And simple. One of the things we talk about a lot on this show, and a thing that is such a crucial part of building anything. is rejection.

Hearing the words. No. For some people It's easy, it doesn't faze them. But for most people

Rejection. is hard. And overcoming the fear of it? Building the resilience it takes to withstand the endless nose? It comes from practice.

Think about previous guests we've had on the show like Mark Cuban and Sarah Blakely. Their earliest jobs were in sales. They had to make the same pitch over and over again. And here hundreds and hundreds of people tell them no over and over again. Same thing with entrepreneurs like Davis Smith who built Cotopaxi and David Neelman of JetBlue.

As young men, they had to do what is probably the most difficult form of salesmanship. Going door to door as missionaries. Most of the time, the doors slammed in their faces. But like anything else? Eventually.

You get used to it, and it helps build up a thick skin, which of course served all of these entrepreneurs very well later on. As it did for today's guest. Taupe Awatana. Tope also spent his early years as a salesman, First, door to door selling alarm systems and later doing million dollar software deals with major companies. And all of the no's he heard along the way?

served him especially well when he eventually went on to launch and then fail at his first two businesses, losing tens of thousands of dollars along the way. But like other people you've heard on the show, Taupe was able to take all of that disappointment, all of the slammed doors, and all the meetings that went nowhere, and all of the failed aspirations. And to think of it. More like research. So that when he finally set out to start a business that did and is doing really, really well.

He had a better idea of what he wasn't supposed to do, and a much better sense of the steps he needed to take. In order to succeed. And what Tope wound up building was Calendly. It's a meeting scheduling platform that he started because he got so frustrated trying to schedule his own meetings and couldn't stand the endless back and forth emails. And today.

Just seven years after it launched? It's a sixty million dollar a year business, and as you'll hear. It reached that point? With just a small amount of outside investment. But before we get to Calendly, a little about Taupe's earliest years. He is Nigerian and he spent his childhood in Africa, growing up in the suburbs of Lagos.

His mom was a pharmacist and his dad was a microbiologist who was also pretty entrepreneurial. He sold chemicals to different businesses. And Tope's early childhood? What Pretty great. Yeah, so Lived in a number of different places, but where I lived, um

For twelve years. You call it like um lower upper class neighborhood for Yeah, in that part of the The world.

knew all of our neighbors were s friends with all the kids in the neighborhood. Um, my parents were, you know, very I'm active in the neighborhood. So everyone kinda knew them and they There were people who were

really kind of very magnetic. And so they just really attracted a lot of people. very generous people, very giving people and people just uh There were always people around. Is what I remember as a kid. Were you a a well behaved kid? Depends on who you ask. I knew how to get into

Enough trouble to really terrorized my siblings. But not really uh face the wrath of my parents. Were your parents strict? Um my mom was my dad was not so much. They could not have been more opposite. So your mom was the kind of disciplinarian.

Your dad was more kinda chilled out. Yes. So my dad was hey, you know, let's eat. Ten ice cream sandwiches for dinner if that's what we want. And my mom's like No ice cream in this house. Was um were you a pretty good student as a as a little kid? I'd say so. Very good, I'd say. Was that something that your parents stressed at home? Education? They did. But not

You know, I don't remember having a lot of conversations with my parents about my grades. There was just an expectation that you performed well in school because they did. I remember as a kid, you know. Probably eight or seven, my mom would

argue with my dad about how she really thought it was important for us to go to Harvard. I didn't know what Harvard was, but I know that uh my mom thought it was important. And when when you were little, like eight, nine, ten, eleven Would people talk about you as a as a smart kid? Would they say, Oh, there's Tope, he's really smart or or did you Just feel like Just everyone he knew was pretty good at school.

Um, I don't know if people did. I think the first time it occurred to me was So I ended up skipping a few grades. Um Yeah. You know, like uh in primary school.

And I think that's when I I knew Mm. And I think my mom was a little Worried about What

That might mean And how How that might play out. So I think that was really the first time I became conscious of it. I guess when you were

Twelve years old, um your father Your father was tragically killed. Um And I I can't imagine um

What that was like for your for your brothers and your mom. What do you remember about that time about how you felt? I remember that it changed everything I thought I knew, so As a kid, I you know My dad was my hero.

Right. Um And you know Because when you're when you're twelve and your dad lets you get away with everything, he's your favorite parent. Yeah. I would stay up late at night till my dad came home, no matter how late that was.

So after he died, you know, I went through You know. A period of time in which I lost a lot of weight. I didn't really have an appetite for many, many months after that. Um I became an insomniac at the age of twelve. Uh These are things I now recognize that are, you know

Um signs of uh Trauma but at the time I didn't really recognize it. You were twelve years old. Um Mm.

Um And And you were there, you s you you saw his death. I did. was a it was a robbery essentially. Um A car checking.

I can't imagine how you We're able to Cope with that as a kid. I mean I mean It's hard for kids to process emotions.

Easily sometimes. I read that you kinda went back to school and I did. I did. Um, I think Some of that is the Nigerian wing. To be honest with you.

But I also think within that my mom had a very My mom was a very Strong person. And You know one of the

Things I really appreciate about the Nigerian culture. It's really everybody's your family, right? Even your your family friends are essentially Think of themselves as your family. Uh so I think she was able to, you know, a lot of people rallied around her. And supported her.

But Uh she definitely It was very, very difficult. Time for her. But I think she also

really wanted us to I don't want to say move on with our lives, but I think she wanted us to You know. She thought the best thing that we could do was Is proceed with our lives, that's what would make our dad uh proud.

Your dad at the time of his death had um He kind of had gone through starting Several businesses and Um some of them were s were kinda did okay and Um but I guess he never kind of fulfilled his dream of really making it big, right?

Yeah. You wanna ask your parents that you don't get to. So I don't really know what his dreams were. I do feel As I think about it. as an adult now is I think he knew that he was uh incredibly he was incredibly gifted in so many different ways.

And I think he felt like uh he hadn't done his best work yet. Mm So from from what I understand, when you finish high school in Legos. you had an opportun an opportunity came to you to go study

In the United States is Is that what happened? Yes. it was always a given that I was gonna go to college in the States. But then what happened was because my mom also retired at the same time. whole family ended up moving.

To the States at that in ninety six. You had family already in the US? Correct. So my older siblings were here, two of my older siblings were here, as well as my aunt. And her husband and her kids. And as a matter of fact, when we first came to the States, we live with them. Where did you move to? Marietta, Georgia.

And what was the plan that you would go to university? I mean you'd finished high school, so what was that the plan? So that was the plan. So I took the S A T. But then my mom was like You can't go to college at fifteen.

You're too young. So I ended up going to high school. I went to Wheeler High School, Marietta. I went there for two years. And and I here I mean I'm curious, I mean what did it what was it like for you? I mean, you'd come from from Lagos To Marietta, Georgia.

And now you were a student there. Was it Totally different. Was it completely different world for you? Oh, absolutely. Hm. I mean everything from the way

The way classes worked. To uniforms, right? So The very fact that you didn't have to wear uniforms was very, very different from what I was used to. One other thing that was very different for me was in high school in Nigeria I was a very popular kid.

But that was very different here, and just New country. Very different culture. And you know, most of the people in the high school they've known each other for many, many years because they went to middle school together. They went to maybe went to elementary school together.

And That was I guess it was Tougher socially than Academically for sure. Yeah. I mean do you remember I mean c coming from Lagos where everybody around you

was black, right? I mean the leaders business leaders and people were powerful and also the poorest people, everybody around you was black and coming to America where Racial issues are Front and center was that. Uh jarring or something that you

Yeah. Expect when you arrived? Not really. And that's not to say they weren't issues, but I think I was probably blind to them. And I think part of the reason why is in a lot of ways I've always kind of been the odd man out.

In everything I've ever done, right. Even in high school Nigeria, I was two years younger than most of the kids. And so I've been kinda used to

Be able to connect with them. All kinds of different people. And not really thinking much about the differences. Um So I probably was

Blind to some of those things. Alright, so here you are. And you graduate high school, so presumably this at this point, you know, you're you you were gonna go to college. You w you had the opportunity to go when you were fifteen, but now you're

Seventeen. Or maybe close to eighteen. So um you you decide to go to the University of Georgia initially, is that right? Correct. And what did you what did you study when you got there? What was your what was your focus?

Computer science. Initially. But I graduated with a a business sorry, a degree in business. And why and why computer science? Yeah, so I picked computer science for um for two reasons. So back in ninety five Windows ninety five was launched. And that really opened my eyes.

I just saw all these uh grown adults, you know. tripping over themselves to buy software. I thought that was really fascinating. I also Notice at the time that the world's richest man was Bill Gates.

And so in my little teenage mind, I started to connect the dots around maybe this is where the world is going. So when you got to the University of Georgia, I mean this is like ninety eight, I guess. I'm still early days of the internet. Did you like it? Did you like living in Athens? Did you like Being a student at UGA? I loved it. I loved it.

I felt like I actually came into my own And I was, you know, developing my own independent. And how were you did you work while you were a student as well? I did. I initially worked at

Uh C V S. Um like as a cashier. Yeah, as a cashier. But then I um you know, like most college kids, I wanted more money. And somehow, I think through a classmate or a friend. I learned about door to door sales. So you thought that's what I wanna do to make more money? Yeah, so I got a job selling alarm systems door to door.

Wow. This is while you were a student, like during the summertime? Yeah, yes, it was a summer job. Uh talk about like the most difficult job ever. I would knock on people's doors at you know right before dinner time. I'm just going to

And so I'm pretty sure half the people who bought from me bought from me just so they could get back to their dinner. And and were you doing this in in Athens, Georgia? Correct. So in Athens, Georgia, so we would um go knock on doors for Three, four hours. and try to make a sale. And what would happen was the job was strictly commission, right? So which is, you know, you could potentially work Uh all week, all month. Yeah, that's right.

How did you do? Did you make decent cash that summer? I did, I did. So what happened was um my very, very first day I sold two alarm systems, which you know allowed me to make five hundred dollars. Which at age, you know. Nineteen. That's that was a lot of money to me. Yeah, it's great money.

It was the most money I've ever made in a day. And uh interestingly, the rest of the week I did not sell anything. And so The very fact that I sold two alarm systems the first day, I think if that sequence would have been reverse, if I would have gone the first four days without selling any alarm systems, um, who knows what I would you know, how my career would have changed. Um but uh that's what happened. Did you like going door to door selling things? That's really hard. I mean, because people slam doors in your face and they're not interested and they say no soliciting.

Did you like that? I liked it. Ha. And I'll tell you why I liked it because of those first two days. Because you made the money.

Yeah, and I think it ultimately gave me the understanding that there's a hit rate, right? So If you knock on the X amount of doors. You will ultimately make X amount of dollars. So to me it was a very predictable thing and in between there's a lot of rejection You know.

People Were unhappy that I interrupted their dinner. That that part was tough. But the rejection of people not really wanting to buy That didn't really faze me. Um, the other thing I really liked was it was the first time like I could

uh I could really influence how much money I made. I could work harder, I could improve my skill And not wait six months, twelve months to make more money. I can make more money the next day, the next week. So did did being a salesperson just come naturally to you, do you think? I guess you could say so. I did feel like it was stretching me in new ways that I had never been stretched before. So keep in mind at the time I'm still a computer science major.

Right. I was used to a different form of any electrical stimulation. I'm coding, you write code and you instruct the computer to do these things for you and you see what you create that was fulfilling. But then this was a whole different A whole different form of fulfillment and satisfaction you could You were influencing people's decisions, right? And that was fulfilling in a way. So he graduated from college and and

When you did did you have a like a ton of job offers? No, far from it. I think one of the things I've learned in myself, you know, uh many, many years after is I think being the Child of immigrants, I think maybe hurt my understanding about to

How to be successful in the business world in America. And so I didn't do some of the things that uh my peers were doing like internships. I didn't do those things. In hindsight, I should have done those things and Yeah, my parents would have known

to I I mean I you know there would have probably push me to do that if they were fr from here. My mom didn't know that herself. Not to put the blame on her, but I think there's I am probably more savvy about how those things work today.

But uh from from what I I read about you, I mean you did Land good sales jobs out of college. Like I think for a couple of years you were working f for for a like a luxury travel agency and then Uh, and then you got a job with IBM. Selling software, um what

What was that like? You know, it took me a while to uh you know, there's a little bit of an adjustment, right? I just spent a lot of time selling to consumers in the last few years and so now I was selling to IT managers, right, to IT people, and also selling in some cases to um to CIOs. So I got exposed to a much more complicated and much more sophisticated sales process. Um but I loved it. Um I found myself not really Like I I enjoy the work I did, but you know, I've always been a very, very impatient person.

Um and so You know, at the time I looked at the CEO of IBM and he was in his uh sixties. And it took'em all forty years to get there and I didn't know that I had that much time to wait. So I want it to be in an accelerator path. And so

I started looking for a much smaller uh software company. that was growing at a much faster rate. So at the time, you know, IBM was probably gro growing double digits every single year. And some of the businesses that I was looking at were, you know, probably going growing double digits every month. And so really wanted to Uh You know, a smaller company with uh

No. More growth opportunity. So you You leave and w where'd you find? I went to Kansas City.

to work for a company called Perceptive Software. It made enterprise content management software, so I think of it as um Software to manage, um Paper files, right? So digitalized files and Manage the approval workflows around it. So this is like the B to B stuff, right?

Yeah. And so I really enjoyed working for the company. W while I was at the company, part of the onboarding process is you get a a chance to to meet with the founders and you know, they they tell the story, the company's founding story. And that story just really opened up my eyes.

Why? You know, it was the first time I heard about the founding story of uh of a company of a successful company. Because before then I thought that most people who started you know very successful companies, they just hit the ground running on day one. They knew exactly what product they want to deliver to the market. customers receive it, accept it, they break their backs to pay their money. But what I learned from this founder was It took them eight years to really uh get to product market fit.

As we call it today. And idea pivoted many, many, many different times. Um And the reason that that business uh became successful was had more to do with their

ability to learn from their customers, their Their own resilience. So from that point on, I think it made me realise that You know, entrepreneurship. So I thought I had to be

No, I just yeah, it's just the story made me realize that I I didn't have to have all the answers, but if I saw something that I thought needed to be changed I just needed it. Take action and uh And so because of that, I started

It kinda rekindle this very, you know. This one. Latent idea that I had. Uh becoming a tech entrepreneur. And so from that point on

I start dabbling in A bunch of small businesses. When we come back in just a moment, how Tope decides to get into e-commerce and how that leads him to failure after failure. Stay with us, I'm Guy Roz, and you're listening to how I built this. Hey, welcome back to How I Built This. I'm Guy Raz.

So it's twenty twelve and Tope has decided to start his own company. But news from his family in Atlanta means He has to change his plans. My mom was really s uh sick, and she ended up being in the ICU for For about a month, month and a half, or so.

And She was recovering from the Complicated case of malaria. Uh. And so because she was recovering from that.

I think at the time she Looking back on it now, she She had cancer at the time. As she was recovering from that. And um

She was just in a In a tough place. And I wanted to be um Closer to her. Um, I was thinking about going back to Atlanta and then at the same time I got recruited by a company in Atlanta that uh

uh one of my best friends was working at And so that kind of accelerated the decision to uh Was it also a uh software company? Yes, it was another software company doing a very similar thing, but for a uh you know, as in selling enterprise software but selling it to in uh So so this company that you joined, I think it was called Vertefor, is it is that right? That's correct. And I guess while you were there, um you meet You meet like this.

business contact to Um, I I don't know the whole story, but but like he starts giving you ideas for how you can Like start your own company? He told me that he'd actually helped a number of different um entrepreneurs. Start a number of different um

E commerce businesses. So he said most people start e commerce businesses Um, because they wanna sell something in particular. They wanna sell hand sanitizers, they wanna sell masks, whatever it may be. It's like well, that's one way to start a business, but he said an an interesting a really interesting way to start a high growth. E commerce business.

is to instead start a business around Around keywords that have a lot of traffic. That you can optimize for. So instead of starting a business to sell hand sanitizers because you want to sell hand sanitizers, what if you start a business selling light bulbs because it turns out that there's a lot of traffic for light bulbs and no one's really satisfying that need very well.

I'm just throwing that as an idea. Okay, I got you, okay. And so I thought that was fascinating, and he showed me some of the businesses that he'd helped start. And uh you know, in hindsight, I should have probably interviewed some of those uh other entrepreneurs. Um But the idea sounded fascinating and so I paid him. to do an analysis for me to find out What are some keywords um

That people are searching for. Exactly. And are not uh and no one's really fulfilling the e commerce uh need. And what did he come up with? He came back with projectors. Projectors. Projectors, yep. Like like slide projectors? Yes. Video projectors. movie projectors so yeah there were actually six specific keywords. It was H D projectors, it was movie projectors. I forget what the other four were were now. So there's it there's a ton of search traffic looking for movie movie projectors and then you analyze the sites that are currently ranked and high for that keyword.

And then you look at how Displaceable they are, basically. And you know, his instincts were that they were easily replaceable, that you could Uh with three, six months of work you could be Um you could be at the the highest ranking site for the for that keyword.

So do you did you start a projector company? I did. I'd never used a projector in my life, right? Well maybe use maybe seen a few in a different meetings, right? But I never really bought one before, set it one up before, but The analysis, you know, seemed compelling to me. And so we started a projector business and we called it ProjectorSpot.com. And uh after Something like two, three months of work, we set up the website.

And uh we're ready to to take orders. And I should add that the We didn't actually go out and buy projectors and sell them on the website. We established dropship and relationships with different wholesalers. And in a space of

Two to three months or so, we launched the business. And did you have to put in a lot of money to to to start this up? Yes. Um I put in probably something like I would say about twenty. thousand dollars or so. I don't remember all the details, but I would say most of it probably went to the website development. Twenty thousand dollars a lot of money, but you were you just saving all the money that you were making from sales?

Over the years. I was, so I had some really good years. Um And I just sucked that money away. And did you Do like when you told your friends about it, d or did you did you tell anybody about it or did you keep it secret? I did and they all laughed.

They'll laugh. They laughed saying What? You're selling movie projectors or h H D projectors like Yeah, they asked me all the all the smart questions they should have asked me. What do you know about projectors? If it's this easy to start a business.

Um, why would this guy just not run the business himself? Why are you so confident that you're gonna rank highly for these keywords? Yeah, so There's a lot of laughter when I uh Sure the idea, for sure.

Alright, so You launch this thing and and Do any orders come in? They do. They do. But then I saw very, very quickly that the margins were

Razor Razor Thin. You end up selling a five hundred dollar projector, maybe you make five dollars, right? Well why are they so thin? Well, one because the electronics in general are just very commoditized. And uh There are many, many other merchants out there and so Most of the competitors were actually not making their money

on the projectors like it was a loss leader for them. what they were really doing was they were creating their own uh they were making money from the accessories or the light bulbs Maybe the lens, I don't I forget what all you know, what all the supplies and parts are which explains why I had no business uh doing this in the first place. But that's really where uh the bulk of their profits came from. So how long did the business last?

I would say less than six months. Mm. Yeah. So you lost all that That twenty thousand dollar investment. I did. I did.

But I wasn't It didn't phase me though I mean it was disappointing in some ways. Yeah um because I had you know,'cause you put a lot of time and effort into getting it to up and running, you sacrifice Many late nights, many weekends in And you do all that and

It doesn't really materialize. How did you know it was time to just give it up? Two things. One I realized that I didn't I just didn't really care about projectors. Right. So what I l A few things happen, right? So whenever people would place orders, uh so some people would place orders without really asking any questions, but then a lot of people really came to projectorspot.com not just looking to buy a projector, but they wanted to be educated about projectors. And so I realized that for me to be successful in this business, one, um, the business model was just really, really tough.

And two. I needed to become passionate and knowledgeable about projectors. And I just didn't really want to spend my life doing that. So

All right, so you you you kinda leave that behind. And did you have an immediate Idea after that? Or did you kinda take some time? No. I knew exactly what I wanted to do next. Wow.

W what I wanted to go back to e commerce. Um And but I thought that this time around I would pick h a higher margin product. And so I turned around and created another e commerce website. And this time around rather than paying the guy

twenty thousand dollars. I built it all myself. You built a a website and and and what was the product? So I call the website yardsteals.com. Yard Steels. Like steals, like cheap deals for the yard. Exactly. Okay. And so the idea was, you know, you can get good deals on home and garden equipment. That was the category that I was uh I go and after and What I wanted to do was I um

A few of my co workers at work were uh Crazy about the big green egg. I'm not sure if you've heard of it before. Sure, the grill, the A to Grill. Yeah. So Ceramic grill and people are fanatic about it. People who love it just love it and they rave about it. But what I spotted was that as fanatical as people were about the big green egg It was actually really difficult to get it if you didn't live in a major city. So if you lived in a city like Atlanta, it was easy for you to get. If you lived in a city like Athens, which is

You know let's call it seventy miles from Atlanta. You had to drive to a major city to get it. And so I thought that um I thought there's an opportunity there. And I started calling the different manufacturers of these um Grills.

I thought I could build a better A better e commerce business than they could. And my larger vision was I would do a better job of driving traffic and driving demand. To

That's two yardstills.com. And eventually I would go start my own. I would Build my own Yeah. Tubes.

Blue egg, whatever you want to call it. And did you sink another twenty grand into this idea? Probably a little less. But I f I forget the exact amount. All right, so you put this up and do orders start to come in? Or just start. Coming in. And the margins are better this time. So instead of making, you know, like five dollars for five hundred dollar purchase, you're making

A few hundred dollars on a I don't know, seven hundred dollar purchases or something like that. So much better margins. But you never saw a big green egg. You would just get the order, you would contact the the shipper and then they would ship out of some warehouse. Exactly. Yeah, I never saw one. It's just

Yeah, order in and order out. And so I think what I found was I did. Much better than the first business, right? So Um probably netted uh sold more grills, one.

But I think this I found that the same problem kinda repeated itself. when people come to buy any kind of product, they're not looking just to just to do the transaction, they're also they're looking to be educated. And so I thought to build a real successful business around this, you have to invest time and effort. into building a brand, into educating people and creating content and doing all these different things. And I just wasn't excited about that work.

I didn't feel like home and gardening I I just didn't feel like that was my calling. So when I mean, so how long did that last? Ultimately that business. Probably about the same three to six months, I would say. Right.

Once you I mean you essentially have two back to back failures. Not this is a good thing, because you're gonna need those in the future. gonna need to start and fail at a couple of businesses. Um, did you think maybe I'll take a break from starting up a business for a while and go back and just get a safe job. Yeah, so this entire time I never quit my day job. So what I end up Doing is uh I'm still working my

You know, my day job at that time, traveling all over the country. But what I realized was that I was I start all these different businesses. Not because I was passionate about solving up A problem?

Or and not because a problem necessarily existed. I was doing all these things because I wanted to start a business. And so I thought that I wanted to take a break. And rather than forcing a business, uh Idea. I thought that

I need to pick a a a problem that truly existed. And I needed to pick something that I was uh you know really excited and committed to being a A student of it. And

I decided that I would basically take a break from starting businesses until I found Until I found that idea that Check all those boxes. Alright, so you are doing your day job selling uh enterprise software. And I guess Uh one day

Um W I I from what from what I understand, you like start to think about scheduling And Calendars Tell me what happens. Yeah, so

I was a national account manager. So I uh managed the A number of um Fortune five hundred accounts in the south east. So companies doing over a billion dollars in revenue. And also selling complex enterprise software to them. So what that meant was The types of the the kind of companies you're selling to are like the Coca Cola's of the world. So they need to bring ten, fifteen people to a meeting. And then a lot of times for the deals that we sold, we needed to also involve uh systems integrators, or so these are the firms that would actually go in and

Deploy the software. And so they would bring another three people. So very often you are trying to arrange meetings with twenty people across three different companies. And it can be very painful.

It's so painful when you've got like five people and want to do a conference call and there's multiple emails and I can do Wednesday. Yeah, but I'm gonna Wednesday, I can't do Wednesday. How about Tuesday? Uh it drives me up the wall. It's a common problem and I'm thinking it's twenty twelve,'cause th at this time it's twenty twelve. Surely this is a solved problem. I'm gonna do an internet search. and see what I can come up with that can really make it easy for

Yeah, twenty people across three different companies to compare their availability. Mm-hmm. And I do a search and I find A number of Different products in the market.

That are solving bits and pieces of it. But none that really that I thought did it really, really well. And you didn't know what that looked like, you were just looking for an option. Correct. I just knew that as a consumer as a potential consumer I didn't feel like any of the Product on the market at the time really checked all the boxes of

What I would need. What was it that you thought you needed? Yeah, so a a few things I thought I needed at the time, so One. There were a lot of products on the market. That we're really

Um Tailored to Brick and mortar businesses, they do a lot of appointments. So if you're a salon and you do hundred appointments a day, there's a lot of great software for you. But if you are an enterprise software sales rep that really does maybe

Yeah. Five external meetings a day or three or four. There were no really good options for you. The other thing I noticed was that Yeah, as a salesperson, one of the things I knew

um very well was that just because you want to meet with somebody doesn't mean they wanna meet with you, right? And so I thought a lot of the products that exist under the market really Spent a lot of time designing for the users of the software, not so much the recipients of the invitation. And so I thought that if this would gain mass adoption, you really needed to build for both For all participants, you needed to make it a great experience for

Every um for all the users of the product, whether they were Your own registered users or the people who are receiving invitations? from your registered users. Those are some of the things that I uh That I noticed. Alright, so you

You think Maybe There's something to this. And so I spent Two, three months.

Signing up for every single product that existed on the market. And really deconstructing them. Tearing them apart. I must have signed up for what felt like probably Yeah.

twenty to thirty different products. I use the products religiously. Um to really understand how they worked. I spent a lot of time in their community forums to really figure out what their customers were saying. I would submit support tickets to really understand. Um

I would pose as a buyer of their software. To understand how they were selling it. Other than pitching it. And what I learned was that

In spite of the fact that I thought there were gaps in what they did, their customers love what they did. In spite of the fact that their customers wanted a lot more. They Thought what they did was incredibly valuable. And so That was interesting to me.

And it told me that If at a minimum you do as much as what they're doing There's a decent business to be had out there. Um and then I thought if you took it to a whole different level. and you really lower the barrier of entry, right? And really democratize it and make it made it simpler for

You know, the more casual schedulers. I thought there was an even bigger opportunity. And I I just knew that this had to be done. And and how long? I mean how how many months does it take before

You say to yourself. Okay. I've done the research. There's nothing like what I wanna make. Maybe may I I g I gotta do this. It takes me six months.

So With the other businesses that I started. I basically had made a decision to start the business and I looked for all the evidence to support the j decision I'd already made. Um with this I led with an open mind. So I was just as happy to not do it as I would have been to to do it. So I just really let the facts kinda guide me. And I was hoping at the end of

You know, my my exploration I would come back and say This is just like the other business ideas that I've had. Someone's already done it and they're doing it really well. Go do something else.

Um, but it's been the six months, um I I couldn't sleep. That's all I thought about. That's all you thought about. Yeah.

When we come back in just a moment. Why Tope put every penny he had into his new project. And why when he finally built it? He was forced to give it away. For free. Stay with us, I'm Guy Roz, and you're listening.

How I built this. Hey, welcome back to how I built this. I'm Guy Roz. So It's around early twenty thirteen and Tope Awatana has this idea. to make software to help people schedule meetings in the most seamless and efficient way possible. And the first thing he needs.

Is for someone to do the coding. And so I decide that this needs to happen fast, so it's not really something I can code myself. And so I start going to meetups. To see if I can uh meet other technical, but That didn't prove to be successful, huh?

And so my third option became Let me see if I can hire a firm. to build the initial product. I did. So what happens is this, a lot of people have uh And everyone has an idea for an app they want to build. And so if you're a talented engineer

You get you get a A lot of terrible pictures every single day. And so most Engineers that are entrepreneurial. They would rather pursue their own ideas, or if they're gonna take their risk, they'd rather you know, like bet on themselves and kinda go after it. So

As uh as easy as it sounds that you know Just because you have an idea doesn't mean that uh you can really attract uh get engineers to get excited about it. This is an important point, right? Because you're right. Everybody has an app idea. But if you're not a software engineer you can't make it, you need one. To help you, but if if you can f if you find a good one, there's a good chance that that engineer wants to start their own business on their own and they would they would sort of be like, Well why should I do this with you? Exactly. And also, you know

They're also probably well paid at what they do, so Yeah, kinda. You know, risking all that to start up a business with some random person. Exactly. So you could not find a technical co founder, which is a common problem.

So to make this thing You decided to like outsource it to like uh Some uh you know, engineering company that does these things for hire. Exactly. So there are lots of companies out there that really help um whether they're large corporations or entrepreneurs bring their products to life. And so what I ended up doing was

I started talking to a c a few companies in the States. There was one in Atlanta, there was one in Charlotte, there was one in San Francisco. Mm. And inevitably The f very first question they would ask me was, What's your budget? And

I get that it's an important question, but I just felt like they all they really cared about was How much you gonna pay us? Exactly. Yeah. Uh And so I kept looking and so I didn't rule those people out, but I ended up getting finding a company in uh Ukraine. And from the first interaction that we had

Yeah. Their initial. Their initial response to me was not how much budget. How much but how much money do you have to put into this, uh

Their first response back was we think this is a great opportunity too. As a matter of fact, here are three ideas that we have. And so I knew I knew that I wanted to pay attention to uh to them. This company's call Railsware, I think, right? Uh I mean, did you make any of these companies sign like non disclosure agreements or or did you just kinda risk it that you would tell them your idea and hope that they wouldn't

Copy it. No, I didn't I did not make them sign any kind of uh N D A's. N because I didn't know. Ultimately what I believe was and it's still what I believe today is I think the key to success is the execution of it, not so much just the idea.

Because you know, a number of other people before me that have the idea. But I was thinking of executing it a very different way, and I thought my own I guess I you know, maybe I was full of myself. I thought my own unique perspective on what needed to be done would be good enough to protect the idea. I mean th this may this is an important point again because

It is true a lot of people are paranoid about talking about their ideas, but ideas Ideas are a dime of a dozen. I and and and ten, twenty, thirty, a hundred other people may have had the idea. That you had. Thousands may have, but it's it's executing the idea well.

Which is Something that you have to believe only you can do. Absolutely. And you know, it's interesting you say that because the other thing that happened in Is As a scrappy entrepreneur, one of the things I try to propose

was hey, why don't I just give you a cut of the equity Uh and you and you can work for free. Um but even they weren't willing to take that risk. Yeah, because otherwise they'd never get paid. I mean Everyone is gonna be

That's correct. And so they weren't uh they weren't willing to do it, and which I I I fully understand and um but it worked out well, I guess. So you hired them To build A a prototype of what this could look like, like an like an M V P a minimally viable product? Yes. Um so before I hired him, I actually flew over to Kiev to meet with them. And we spent two days really brainstorming on the idea.

The They challenged me in a lot of different ways. I learned a lot from them. Um but I actually came back to the States Initially not thinking that I was gonna do the idea. I actually came back from the meeting thinking Man, this is

Much bigger than I thought. Maybe Maybe it's too much to do. But I uh ended up changing my mind. Why? Um a few things happened.

Around the same time I found out that my mom's uh cancer was terminal. Yeah. Uh And I think it gave me a sense of

Carpet DM a little bit. And just really realizing that You know. Who knows how much Time we all have

Yeah, like Here's my mom and Yeah. Yeah, she's dying. Yeah. Would she make the same decision?

If she was faced with the same decision knowing her lifespan, how what decision would she make? Uh That really changed my thinking around Go for it. You're thinking, Who knows what's gonna happen to me tomorrow?

Better do this. Correct. Now's the time to do it. Nothing's guaranteed. You can try to wait for the perfect moment, the perfect idea. Um the perfect the perfect development sequence. Or you can start with uh this place in

Start it with what you can do. And expand from there. Alright, so you decide to do this. And How much was it gonna cost you to get this?

prototype built. A little over two hundred thousand dollars is what we thought it would cost. Wow. Did you have that money? I had most of it. But it required.

Doing a lot of things they tell you not to do. So I had to empty every single dollar my four one K. And pay the pay the penalty, presumably. Yep. Um I had to um Use every single dollar in my savings account. I had to borrow a little bit on top of that. Um I ended up borrowing a little bit from Linden Club. At a high interest rate. At a very high interest rate. So cobble together.

My four one K and uh my savings and then uh and then some debt and maxed out all my credit cards. And uh put it all in on uh On this f uh on this idea that at the time didn't even have a name. I mean that's um

really big risk. I mean y yeah, you know, you were what thirty one, thirty two I guess. So still could recover if it if it was a disaster. But I mean wow, that's a lot of money. You were basically cleaned out. I'm assuming. Yes.

Aren't you nervous? Not at all. It sounds crazy to say that now and it could have gone it could have been really really really bad and I it would have set me back uh many many years if it didn't work out. But not at all. Here's why. I've learned a lot from my previous failures. This felt like uh you know, as crazy as it sounds, I felt like I had a call in to do this.

Alright. For a number of reasons. I felt like I spent all my life In sales and I think I really understood. I feel like I knew a lot about meetings and median etiquette and What works, what doesn't work.

I felt like I actually And unlike the e commerce businesses that I tried to start, I actually knew a lot about software businesses. And I feel like I Because I spent so much time researching the air the space I felt like I knew exactly what needed to be built to build a great business.

Uh so it sounds crazy, but I wasn't I wasn't scared. So this is twenty thirteen, you put all your money into this product. this f for this company Railsware, most of that money's going to them. What did you tell them? You said okay, I want this to be

Like A calendar. That somebody can just say Hey, here's a link to my calendar, you pick a time. When you want to meet me.

And that calendar would be integrated with Whatever they used, whether it was Google or or Microsoft or whatever. Yeah, so a few things. So before I ever met Railsware, I'd actually come up with my own requirements document. Okay. So which again, something I didn't do with the previous businesses. So I had I create my own detailed

um list of requirements and detailed flows that need to happen that needed to be built and also My own sequence of how the work needed to be done. So what were your requirements? Oh man, you need to be able to integrate your calendar, be able to specify your availability in all these different ways. Uh, you need to be regarded your availability. And so

You know, I I thought the user experience and design Just needed to be front and center. Like it just needed to be appealing functionally and also aesthetically. We had to get really fancy with um With how we detect the time zones to make it

really, really accurate without the user having to uh So there are a lot of technical small little technical details that really made a difference in the U ex user experience that we had to figure out. Alright, so you get this product. It takes about Um, six or seven months.

Uh meantime, how is your mom doing? This is twenty thirteen. Yeah. She died about two months into the into the development. So she died in June twenty thirteen. Mm. Did your mom know much about what you were working on?

Not really. So I kinda downplayed it to her, so I told her that I was um Ex you know, she knew that about the she knew about the previous businesses and she She supported my uh my different business ideas, but She wanted me to She wanted me to prioritize my my day job.

Ha ha But she thought it was you know it was She thought I was doing really good, um, with my job and that she didn't lose Uh. She didn't want me to lose focus of that. So in some ways I downplayed what I'd done to her, but I'd really committed a few hundred thousand dollars to it.

He never told her. I did not. because she wanted you to have security and health insurance and all that stuff, right? Correct. All the things that she felt like um you know. She wanted for her son and she wishes that you know

That my dad always provided, right? Yeah. So After her death, I mean

How were you able to kinda just'cause you were in the midst of Building this thing. Like this was intense. I mean Soon after you were you were in Ukraine again. How do you stay focused?

Yeah, so I I poured myself into the into the business, into the product. And so And it was a very, very, very difficult thing for me. Very, very difficult.

But Calma became a huge distraction from it. And I just Award. Like a dog.

So I didn't have to think about that. So by the Fall around September of twenty thirteen. The first version of this product is available, but you had spent all your money on developing it, so

How are you going to I don't know, pay for the servers and pay for I mean get the word out about it. I mean H'cause you had no money left, right? Yeah, so

Okay. Yeah. I know help along the way. Um Through Railway actually. So a few things happened. Yeah.

As Ralesware was building the product. They Got connected to Another potential client. A software company in San Francisco that's

Yeah, gone on and Done really well to a multi hundred million dollar business. Yeah. And If that company was looking to engage them to do some work for them. And so Railsware was

Yeah. was like hey, let's show you this product that we're building. Right. So they show them calendarly. And at the time Cal is not quite it's in a it's not quite ready.

To be in a public beta? But what what ends up happening is they love the product. And so somebody from there From their s customer success team. signs up for the product and starts using it to schedule

Onboarding calls. With their customers. Which those customers happen to be Um K two K through twelve schools.

So a customer success person from this company in San Francisco starts scheduling Onboarding calls with uh K through to our schools. Yeah. So the cat's out of the back at that point.

Because when you send somebody your calendarly link and they see it. They're like, Hey, what's this? I I want this too. Exactly. They say I schedule a lot of meetings. That was easy.

I would love to use this to simplify my meetings. And so The K through twelve twelve schools start adopting it and then they turn around and start using it for parent teacher conferences. Right. So the use case goes from We're doing using it to do onboarding calls to these schools start doing parent teacher conferences with it.

And then you know, a few weeks in A school comes to us and says This is the best thing that's ever happened to us. We've been struggling with parent teacher conferences. We struggle with you know how you know You know, the administrative burden of setting them up, the participation rates. Um we wanna roll this out to all of our teachers.

Hm. Yeah. Where's the school? In Kentucky. And so they come to me and they say they want to sign up eighty teachers and I just Eighty teachers.

Which at the time was a lot of people and I've been a little bit more just to interrupt, Tope, what was your business model? How would you make money off of this at that point? Yeah, so I'm glad you raised that because I neglected to mention that. So because I ran out of money No my my idea, um the business model going into it was to to have a fourteen day trial. So you could use the product for free, no credit card, no uh feature restrictions for free for fourteen days.

And at the end of those fourteen days you would have to Upgrade with a credit card. Well, and then pay like a subscription fee. Exactly. Mm-hmm. Um but because I ran out of money, we couldn't build a

the billing uh features and so by default the product became hundred percent free. You couldn't build the billing features? Correct, because I ran out of m I I had just enough money to bill the Uh the scheduling capabilities. Mm. But not enough money to get around to

To enforce the billing. So no way to capture revenue from you know, potential users. You couldn't just like set up qu I guess you can't really set up quick books, right? Well you can set up quick books, but it's with an online product you have to find a way to restrict the f features if they're not paying. Yeah. There's some technical complexity there and some work that needs to be done to uh to kinda turn the features off and on based on their trial status, their payment status, collecting the payments. Initially, I mean to just to give you an idea, initially that's

That was pr maybe. Two three months of work for two engineers to work on that? Well. Okay, so you could not do this. So you so you were forced to give this away Now, but then how were you gonna pay for it? I mean You're giving it away, how are you gonna make money? Wha I mean was the plan to just

get a bunch of users and then kind of figure it out. Hopefully you would get investment. Yeah, so that that has to become the idea. So I I was faced with this dilemma. Uh so keep in mind I'm still working my I'm still working my full time job this whole time. Your day job. Yeah. So I hadn't left that. So this is you know, this is my side hustle. I was still you know, I was meeting my obligation to the company. I was actually had a really good year that year. Um And so I felt like so long as I was you know, it was not interfering with my job, it didn't really I didn't I didn't feel like I needed to disclose it. Um And so I have this dilemma in which the business is growing, you know, in the sense that people sign up for it and every time

Um every day the signs are growing because of the virality of the product and because people people are are getting good value from using the product. Um but I had no I didn't have the money to To turn it into a revenue generating business. And and just to clarify It really started with this one.

software company in San Francisco and then went to teachers And then from there it just organically grew? Exactly. So the first you know Three hundred to five hundred sign ups really came heavily from K three twelve. But after that initial wave of K through twelve It spread to all kinds of different industries, it spread to to people in all kinds of different roles. It was salespeople, it was recruiters, it was freelancers, it was consultants. Um

I just began to spread like a wildfire. When when did you know or when did you feel comf comfortable leaving your job? Your day job. I wouldn't say so I don't know that I actually felt comfortable, but I I um I knew that a decision had to be made'cause I

Yeah. Of Calonley, I realize that. One, this thing was growing, in spite of the fact that I was just doing it part time. And two, I owned a hundred percent of this thing that was growing and so Uh to me the choice was very obvious. And during this time, did you tell anybody about about your idea or or did you keep it a secret? Like did you did you tell your friends about it? I told my close friends. I definitely told my my my brothers and my siblings

Did people think it was a good idea? No, they didn't think so. They thought it was a solved problem. I remember when I uh when I was leaving and I told my boss I was leaving. He's like you're leaving for that? He felt like he'd filled me that I f you know, like he felt like I was uh I g g get desperate and I you know and I'm pursuing You know, scheduling? That's a salt problem. Like nobody needs that. But yeah, it was not it was definitely not obvious. I didn't quite know how I was gonna fund it.

Um, but I the the decision to me was clear. And so I began to um put together a pitch deck and start going to different um events trying to meet investors. And at that point you still had not you were fully you'd funded this thing by yourself. Funded it myself. Um And Ran out of money. And then I convinced Railsware. To work for not to work for free, but to w work with the understanding that when I raise money I would pay them back.

So I was able to get them to work on credit. There's a quote of yours I read, and I want to read it to you. Um I'm curious to ask you. More about it. Um

'C you described the process of trying to raise money. Um you said everyone said no. Meanwhile, I watched other people who fit a different profile. those VCs were ignorant and short sighted. The only thing I could attribute it to was that I was black.

Um can you Can you walk me through your experience trying to raise money? Yeah, so I think First of all, I think it is difficult for Um

Pre revenue businesses in general to raise money. Especially in the south east, right? Because I think that The farther you wait you are away from the coast, the more the Ah, the more investors value. Revenue?

Whereas when you're on the coast, I think they care more about growth. Um so I think that process for anybody's is challenging, but I'm sure race pa plays some aspect in it, but it's not really There's probably more to it than that. But did you but I mean you didn't really it it sounds like you didn't really

kind of pitch to investors at this point yet? No I definitely pitch to investors. Yeah, and I I got um All in all in Atlanta, the Atlanta area. All in the south east. So a few people in Atlanta, few f few people in the south east. I had, you know, um A guy from a A pretty big firm. Not only did he Yeah.

I mean I'll tell you I had a very What I thought was a very condescending kind of experience. So At the time I was actually in Kiev. Right, so

I'd flown to Kiev to work with Railsware. And I stayed up till two AM to meet with this person. And then he stands me up. Right.

So just a lot of like a a lot of experiences like that that were just Yeah, it's one thing to not invest, but it's another thing to to kinda treat people like that. Yeah. How much is that just the arrogance of, you know somebody who thinks are an important V C versus race. I I know I I who knows, but I mean I do know that uh

many other entrepreneurs who didn't have as much, uh who hadn't made as much progress, um had more of it than I did. So how did you Eventually wind up. Connecting with people who

who did want to invest. Yeah. So I um I started going to different events. I got started connecting with people in the startup community. And then I

I ended up signing up for um A membership at a uh At a place in Atlanta called the Atlanta Tech Village, which is a Um it's a co working space specifically for tech startups. And it's while I'm connecting with different investors that the f the owner of the Atlanta Tech Village catches wind.

Um of Calendly. David Cummins is his name. And he thinks it's really interesting. Uh because he At the time he was actually using a competitive product.

And so he knew firsthand. No, this is a a big problem. Any Was impressed with what we'd done. And so we get connected. Huh. So what happens?

So we have a one or two meetings and um he follows up with a term sheet and says I'm I love what you're doing. I think that this is the this can be big. I'd love to invest. I read that it was like three hundred fifty thousand dollars or something like that.

Were you nervous about taking that investment?'Cause you owned a hundred percent of this thing, but but at the same time you needed the money. Yeah. I was ambivalent about raising money, to be honest with you,'cause you know, I feel like I started the business, you know, in the most difficult way possible. You know, really, you know, put in everything I had, risking everything I had to start the business and so In some ways it felt like a step backwards to have to seed Yeah.

ownership. But once I met David Um that changed. Um In the sense that like I felt like I was gonna have a uh When I was gonna be you know. working with a successful entrepreneur th himself and not just a

A money man? Right. Um I felt like um I could learn a lot from From him. And so

the ambivalence I had went away once I uh once I met him. So It's uh it's the spring of twenty fourteen. And um you get this Disinvestment.

in your business of about three hundred and fifty thousand dollars. And how much runway does that give you at At that time. Because I I mean I'm I'm assuming the business even in April was It was just you, right? That's right. So

Um it was just me. I was the only employee and then you know real swear. And so that ended up giving me I wanna say something like nine months of runway. And do you remember how many I don't know How many People had you signed up by You know.

a year into it by September of twenty fourteen. Maybe about fifteen thousand at the time. Right. So it's pretty good. And I I'm assuming that in that first full year, twenty fourteen, you really had to figure out a plan to make this profitable, right? To monetize this. Yes, and so that became, you know, priority number one was how you raise the three hundred and fifty thousand dollars. Um Because honestly I

I didn't enjoy the find raising experience and I wanted to make sure that I was uh I never really had to do that again. And so I Prioritized um Generating revenue.

By August twenty fourteen, we turned on Billing and introduced uh A premium plan. And so we start generating revenue and August of twenty fourteen. And how did the premium plan work?

Yeah, so that actually created It created some fiction at the time and you know, looking back on it would have done it differently. But part of friction with Customers. Um and so some portion of the existing user base um was disappointed that they had now had to pay for a product that was hundred percent free. Right.

But really what the what the premium plan did was he basically Um We still had a free product, but we just limited um what you could do on the free plan. And so you had to upgrade to the premium plan to get

P let's call it sixty percent of the features you used to be able to get for free before. Right. And what was what were you charging for it? Ten dollars monthly. Um if you pay if you paid monthly or ninety six dollars if you paid annually. And and was your idea already at that point that hopefully one day big companies like Microsoft or you know Microsoft but like Yeah, big companies.

would would use your Your service? It absolutely was the the plan to eventually um begin to acquire larger customers. But some of that was already happening, right? So we were getting No pockets of you know a department in

In those big big businesses using our product. And do you I mean, do you at this point do you just kind of do you continue to seek out outside investors or or do you decide to just see if you can make a a a go at it. You know, through cash flow and revenue. A little bit of both. So

We start to generate revenue. And It definitely extends the runway and I forget exactly how much uh additional time it gave us, but we ended up raising an additional two hundred thousand dollars in early twenty fifteen. That's cushion is an insurance uh policy of sorts. We ended up not needing it. Wow. But we did Were you ever worried that some big company like you know, like Microsoft or Google or somebody else would just come in and with a lot more money uh you know, and just

Uh crush you? I used to. What I found is that, you know, when you spend a lot of time with your customers, I think you You find out that there's a there are a lot of things that they wanna do. Um that need to be done that maybe those companies don't have the appetite for doing.

I mean. It as you kind of think about, you know With a product you offer. Um and how you know Technology changes so quickly.

What w I mean, are you thinking like four or five steps ahead of what Callendly might be to make sure that it doesn't become Obsolete? I do, and I s I spent a lot of my time thinking about that. Yeah. Our overall vision is to take the work out of mediums, right? So

We really think about our mission as not just removing the back and forth of scheduling, but how can we really Um automate the entire meeting experience, right? So Yeah, too often Not only are meet meetings difficult to schedule, people sometimes forget to show up. When they show up, they're not prepared.

Um There's no clear memorialization of the key decisions that are made. Um And you know, action items that are open. Those are the things that we're looking to fix. And there's a lot there.

And uh that will keep us very, very busy for five years. Would you ever sell a company to, you know? A sales force or a huge player like that? Absolutely not. I'm I'm very excited about what we're doing and uh I feel like we're just getting started and there's a lot to there's a lot to do.

And so That's not uh remotely on my radar. Mm. When you think about your journey. Um and and what you've

accomplished. Um Yeah, we've had some Incredible lows in your life? Um Some

Mm. Um in this just unbelievable success. H how much of this do you tribute to to your hard work and talent and how much do you think it it has to do with just being lucky?

Oh that's a Great question. So I think everybody's lucky, right? I think the very fact that I didn't get hit by a bus today, that's luck, right? And we're and same thing for you. The fact that that didn't happen to you, that's luck. Um And you know. I look at the f family I was born into, I think your family really determines your

Your ceiling in life and your And your floor as well, like how high both how high or low both of those things are. And I had no say in the family that I was born into, so I feel incredibly lucky there. I picked the right industry, you know, one that's grown like crazy. So Well, those things are definitely luck. Uh but I think

So I think we're all lucky, but I think what amplifies that luck And what makes one successful It's hard work, it's skill. It's resilience. Uh it's an appetite for risk taken.

So that's my view. I think it's a combination of both, but I think when you Add Those four things, uh it just uh takes locked a whole different level. That's Tope Awatana, founder and CEO of Calendly.

In 2020, when I first spoke to Taupe, the company was doing around$70 million in annual revenue, and since that interview the company took on a huge chunk of outside investment with a valuation Three billion dollars. Hey, thanks so much for listening to the show this week. Please make sure to click the follow button on your podcast app so you never miss a new episode of the show, and of course, it's free. This episode was produced by Rachel Faulkner with music composed by Ramteen Arablui.

It was edited by Neva Grant with research help from Dereth Gales. Our production staff also includes Casey Herman, Carrie Thompson, John Isabella, Alex Chung, Chris Massini, Carla Esteves, Sam Paulson, Malia Agadello, and Catherine Seifer. I'm Guy Raz, and you've been listening to How I Built This.

What you see above is a preview of the first minutes. One unlock costs 3 credits and covers this episode forever: full segment and word-level timestamps on this page, plus .txt, .srt, .vtt and word-level JSON downloads, as many times as you like.