CEOInterviews.AICalendly: Tope Awotona (2020)

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Narrator0:00

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Guy Raz3:44

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 Calendly was born. It was an episode that first ran back in 2020 and I hope you enjoy it. Oh, and one more thing, just a quick note on this episode. Tope Awotona's name is pronounced top. 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 going to cost you to get this prototype built?

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Tope Awotona4:34

A little over $200,000 is what we thought it would cost.

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Guy Raz4:37

Wow.

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Tope Awotona4:38

So I had to empty every single dollar of 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 Lending Club at a high interest rate. I had 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.

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Guy Raz5:05

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 Tope Awotona turned his frustration with scheduling meetings into Calendly, 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 nos, it comes from practice. Think about previous guests we've had on the show, like Mark Cuban and Sara Blakely. Their earliest jobs were in sales. They had to make the same pitch over and over again and hear hundreds and hundreds of people tell them no over and over again. Same thing with entrepreneurs like Davis Smith who built Cotopaxi and David Neeleman 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, Tope Awotona.

Top 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 nos 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, Top 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 Top 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 7 years after it launched, it's a $60 million 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 Top's earliest years. He's 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 Top's early childhood was pretty great.

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Tope Awotona8:37

Yeah. So lived in a number of different places but where I lived for 12 years, you call it like a lower upper class neighborhood for that part of the world. Knew all of our neighbors, were friends with all the kids in the neighborhood. My parents were very active in the neighborhood. So everyone kind of knew them and they 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 there were always people around is what I remember as a kid.

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Guy Raz9:15

Were you a well-behaved kid?

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Tope Awotona9:18

Depends on who you ask. I knew how to get into enough trouble to really terrorize my siblings but not really face the wrath of my parents.

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Guy Raz9:27

Were your parents strict? My mom was, my dad was not so much. They could not have been more opposite.

So your mom was the kind of the disciplinarian. Your dad was more kind of chilled out.

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Tope Awotona9:38

Yes. So my dad was hey, let's eat 10 ice cream sandwiches for dinner if that's what we want. And my mom's like no ice cream in this house.

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Guy Raz9:48

Were you a pretty good student as a little kid?

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Tope Awotona9:51

I'd say so. Very good.

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Guy Raz9:52

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, 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. And I didn't know what Harvard was, but I know that my mom thought it was important. And when you were little, like 8, 9, 10, 11, would people talk about you as a smart kid? Would they say, 'Oh, there's Top. He's really smart.' Or did you just feel like everyone you knew was pretty good at school?

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Tope Awotona10:32

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 in primary school. And I think that's when I knew and I think my mom was a little worried about what that might mean and how that might play out. So I think that was really the first time I became conscious of it.

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Guy Raz10:59

I guess when you were 12 years old, your father was tragically killed. And I can't imagine what that was like for you, for your brothers and your mom. What do you remember about that time about how you felt?

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Tope Awotona11:18

I remember that it changed everything I thought I knew. So, as a kid, my dad was my hero, right? And because when you're 12 and your dad lets you get away with everything, he's your favorite parent. I would stay up late at night till my dad came home. No matter how late that was. So after he died, I went through 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. I became an insomniac at the age of 12. These are things I now recognize that are signs of trauma, but at the time I didn't really recognize it.

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Guy Raz12:00

You were 12 years old when your father died. And you were there. You saw his death. It was a robbery essentially, a carjacking. I can't imagine how you were able to cope with that as a kid. I mean, it's hard for kids to process emotions easily sometimes. I read that you kind of went back to school and kind of carried on.

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Tope Awotona12:27

I did. I think some of that is the Nigerian way to be honest with you, but I also think within that, my mom was a very strong and resilient person. And one of the things I really appreciate about the Nigerian culture is really everybody's your family, right? Even your family friends essentially think of themselves as your family. So I think she was able to, a lot of people rallied around her and supported her, but she definitely it was a 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, she thought the best thing that we could do is proceed with our lives, that's what would make our dad proud.

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Guy Raz13:21

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

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Tope Awotona13:36

You know, I don't know. I think that's one of the things I really miss actually is when you're 12 years old there are a lot of things you want to 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 incredibly gifted in so many different ways and I think he felt like he hadn't done his best work yet.

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Guy Raz14:00

So from what I understand when you finished high school in Lagos, you had an opportunity to go study in the United States. Is that what happened?

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Tope Awotona14:13

Yes. It was always a given that I was going to go to college in the States, but then what happened was because my mom also retired at the same time, the whole family ended up moving to the States in 1996.

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Guy Raz14:26

You had family already in the US.

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Tope Awotona14:28

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 lived with them.

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Guy Raz14:38

Where did you move to? Marietta, Georgia. And what was the plan? That you would go to university? You'd finished high school, so what was the plan?

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Tope Awotona14:46

So, that was the plan. So, I took the SAT, but then my mom was like, 'You can't go to college at 15. You're too young.' So, I ended up going to high school. I went to Wheeler High School in Marietta. I went there for 2 years.

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Guy Raz14:58

And I'm curious. I mean, what was it like for you? You'd come from Lagos to Marietta, Georgia, and now you were a student there. Was it totally different? Was it a completely different world for you?

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Tope Awotona15:13

Oh, absolutely. I mean, everything from the way classes worked to uniforms, right? So, the very fact that you didn't have to wear uniforms was 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. And that was very different here. You know, just new country, very different culture. And 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 elementary school together, and that was I guess it was tougher socially than academically. For sure.

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Guy Raz15:54

Yeah. I mean, do you remember coming from Lagos where everybody around you was black? The leaders, business leaders, and people were powerful and also the poorest people, everybody around you was black. Coming to America where racial issues are front and center. Was that sort of jarring or something that you didn't expect when you arrived?

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Tope Awotona16:17

Not really. And that's not to say there 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? So even in high school in Nigeria, I was 2 years younger than most of the kids. And so I've been kind of used to being the odd man out and just really being able to connect with all kinds of different people and not really thinking much about the differences. So I probably was blind to some of those things.

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Guy Raz16:50

All right. So here you are and you graduate high school. So presumably at this point, you were going to go to college. You had the opportunity to go when you were 15, but now you're 17 or maybe close to 18. So you decide to go to the University of Georgia initially. Is that right?

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Tope Awotona17:08

Correct.

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Guy Raz17:09

And what did you study when you got there? What was your focus?

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Tope Awotona17:13

Computer science initially, but I graduated with a degree in business.

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Guy Raz17:18

And why computer science?

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Tope Awotona17:19

Yeah. So, I picked computer science for two reasons. So, back in '95, Windows 95 was launched, and that really opened my eyes. I just saw all these grown adults tripping over themselves to buy software. I thought that was really fascinating. I also noticed at the time that the world's richest man was Bill Gates. And so, my little teenage mind, I started to connect the dots around maybe this is where the world is going.

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Guy Raz17:47

So, when you got to the University of Georgia, I mean, this is like 98, I guess. Still early days of the internet. Did you like it? Did you like living in Athens? Did you like being a student at UGA?

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Tope Awotona18:00

I loved it. I loved it. I felt like I actually came into my own and I was developing my own independence.

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Guy Raz18:06

And how were you? Did you work while you were a student as well?

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Tope Awotona18:09

I did. So, I initially worked at CVS as a cashier.

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Guy Raz18:17

Like as a cashier.

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Tope Awotona18:18

Yeah, as a cashier. But then I, 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.

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Guy Raz18:30

So you thought that's what I want to do to make more money.

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Tope Awotona18:33

Yeah. So I got a job selling alarm systems door-to-door.

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Guy Raz18:37

Wow. This is while you were a student like during the summer time.

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Tope Awotona18:40

Yeah. Yes. It was a summer job. Talk about the most difficult job ever. I would knock on people's doors at right before dinner time 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.

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Guy Raz18:55

And were you doing this in Athens, Georgia?

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Tope Awotona18:59

Correct. So in Athens, Georgia. So we would go knock on doors for 3 or 4 hours and try to make a sale. And what would happen was the job was strictly commission, right? So, you could potentially work all week, all month and make nothing.

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Guy Raz19:15

How did you do? Did you make decent cash that summer?

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Tope Awotona19:19

I did. I did. So, what happened was my very first day I sold two alarm systems, which allowed me to make $500, which at age 19, that was a lot of money to me. And interestingly the rest of the week I did not sell anything. So the very fact that I sold two alarm systems the first day, I think if that sequence would have been reversed if I would have gone the first four days without selling any alarm systems, who knows what my career would have changed. But that's what happened.

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Guy Raz19:56

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?

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Tope Awotona20:05

I liked it.

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Guy Raz20:07

Huh.

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Tope Awotona20:08

And I'll tell you why I liked it. Because of those first two days. And I think it ultimately gave me the understanding that there's a hit rate, right? So if you knock on 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 part was tough. But the rejection of people not really wanting to buy that didn't really faze me. The other thing I really liked was it was the first time I could really influence how much money I made. I could work harder. I could improve my skill and not wait 6 months, 12 months to make more money. I could make more money the next day, the next week.

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Guy Raz20:52

So did being a salesperson just come naturally to you? Do you think?

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Tope Awotona20:56

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? So I was used to a different form of intellectual 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 form of fulfillment and satisfaction. You were influencing people's decisions, right? That was fulfilling in a way.

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Guy Raz21:24

So you graduated from college and when you did, did you have a ton of job offers?

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Tope Awotona21:29

No, far from it. I think one of the things I've learned, myself, many years after is I think being the child of immigrants, I think maybe hurt my understanding of how to be successful in the business world in America. And so, I didn't do some of the things that my peers were doing like internships. I didn't do those things. In hindsight, I should have done those things. And my parents would have known to, they would have probably pushed me to do that if they were from here, but they didn't. My mom didn't know that herself. Not to put the blame on her, but I am probably more savvy about how those things work today.

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Guy Raz22:11

But from what I read about you, you did land a couple of pretty good sales jobs out of college. Like I think for a couple years you were working for a luxury travel agency and then you got a job with IBM selling software. What was that like?

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Tope Awotona22:31

It took me a while to adjust. I spent a lot of time selling to consumers in the last few years and so now I was selling to IT managers, to IT people and also selling in some cases to CIOs. So, I got exposed to a much more complicated, a much more sophisticated sales process. But I loved it. I found myself, I enjoyed the work I did, but I've always been a very impatient person. And so, at the time I looked at the CEO of IBM and he was in his 60s and it took him all 40 years to get there and I didn't know that I had that much time to wait. So I wanted to be on an accelerated path and so I started looking for a much smaller software company that was growing at a much faster rate. So at the time, IBM was probably growing double digits every single year. And some of the businesses that I was looking at were probably growing double digits every month. And so really wanted to work for a smaller company with more growth opportunity.

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Guy Raz23:45

So you leave and where did you find?

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Tope Awotona23:48

I went to Kansas City to work for a company called Perceptive Software. It made enterprise content management software. So, think of it as software to manage paper files, right? So, digitalize files and manage the approval workflows around it.

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Guy Raz24:05

So, this is like B2B stuff, right?

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Tope Awotona24:07

Yeah. And so, I really enjoyed working for the company. While I was at the company, part of the onboarding process is you get a chance to meet with the founders and they tell the story of the company's founding story and that story just really opened up my eyes. It was the first time I heard about the founding story of a successful company because before then I thought that most people who started 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, they accept it, they break their backs to pay them money. But what I learned from this founder was it took them eight years to really get to product market fit as we call it today. And the idea pivoted many many many different times. And the reason that business became successful was had more to do with their ability to learn from their customers, their own resilience. So from that point on, I think it made me realize that entrepreneurship was way more attainable than I thought it was before that. So I thought I had to be, I just, yeah, just the story made me realize that I didn't have to have all the answers, but if I saw something that I thought needed to be changed, I just needed to take action and learn and persevere. And so because of that, it rekindled this very latent idea that I had of becoming a tech entrepreneur.

And so from that point on, I started dabbling in a bunch of small businesses.

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Guy Raz25:45

When we come back in just a moment, how Top decides to get into e-commerce and how that leads him to failure after failure. Stay with us. I'm Guy Raz and you're listening to How I Built This.

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Narrator26:05

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Guy Raz30:07

Hey, welcome back to How I Built This. I'm Guy Raz. So, it's 2012 and Tope has decided to start his own company, but news from his family in Atlanta means he has to change his plans.

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Tope Awotona30:20

My mom was really sick and she ended up being in the ICU for about a month, month and a half or so. And she was recovering from a complicated case of malaria. And so because she was recovering from that, I think at the time she, looking back on it now, she had cancer at the time as she was recovering from that and she was just in a tough place and I wanted to be closer to her. I was thinking about going back to Atlanta and then at the same time I got recruited by a company in Atlanta that one of my best friends was working at and so that kind of accelerated the decision to come back to Atlanta.

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Guy Raz31:07

Was it also a software company?

T

Tope Awotona31:09

Yes, it was another software company doing a very similar thing but for a different industry.

G

Guy Raz31:18

So this company that you joined, I think it was called Verafour, is that right?

T

Tope Awotona31:22

That's correct. And I guess while you were there, you meet a business contact who starts giving you ideas for how you can start your own company.

Yeah. So he told me that he'd actually helped a number of different entrepreneurs start a number of different e-commerce businesses. So he said most people start e-commerce businesses because they want to sell something in particular. They want to sell hand sanitizers, they want to sell masks, whatever it may be. It's like, well, that's one way to start a business. But he said a really interesting way to start a high growth e-commerce business is to instead start a business 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 started 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.

G

Guy Raz32:23

Okay, I got you. Okay.

T

Tope Awotona32:24

And so I thought that was fascinating and he showed me some of the businesses that he'd helped start and in hindsight I should have probably interviewed some of those other entrepreneurs. But the idea sounded fascinating and so I paid him to do an analysis for me to find out what are some keywords that people are searching for.

G

Guy Raz32:44

Exactly. And are not and no one's really fulfilling the e-commerce need.

T

Tope Awotona32:49

And what did he come up with?

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Guy Raz32:51

He came back with projectors.

T

Tope Awotona32:53

Projectors.

G

Guy Raz32:55

Like slide projectors.

T

Tope Awotona32:58

Yes. Video projectors. Movie projectors. So projectors. Yeah. There were actually six specific keywords. It was HD projectors. It was movie projectors. I forget what the other four were. So there's a ton of search traffic looking for movie projectors. And then you analyze the sites that are currently ranking high for that keyword. And then you look at how displaceable they are basically. And his instincts were that they were easily replaceable, that you could with 3 to 6 months of work, you could be the highest ranking site for that keyword.

G

Guy Raz33:33

So, did you start a projector company?

T

Tope Awotona33:36

I did. I'd never used a projector in my life, right? Well, maybe seen a few in different meetings, but never really bought one before, set one up before, but the analysis seemed compelling to me. And so we started a projector business and we called it projectorpot.com. And after something like two, three months of work, we set up the website and we were ready to take orders. And I should add that we didn't actually go out and buy projectors and sell them on the website. We established drop shipping relationships with different wholesalers. And in the space of 2 to 3 months or so, we launched the business.

G

Guy Raz34:17

And did you have to put in a lot of money to start this up?

T

Tope Awotona34:21

Yes. I put in probably something like I would say about $20,000 or so. I don't remember all the details, but I would say most of it probably went to the website development.

G

Guy Raz34:32

$20,000 is a lot of money, but you were just saving all the money that you were making from sales over the years?

T

Tope Awotona34:38

I was. So I had some really good years. And I just socked that money away.

G

Guy Raz34:44

And did you like when you told your friends about it or did you tell anybody about it or did you keep it secret?

T

Tope Awotona34:52

I did and they all laughed.

G

Guy Raz34:53

They all laughed. They laughed saying what, you're selling movie projectors or HD projectors like?

T

Tope Awotona34:59

Yeah. They asked me all the smart questions they should have asked me. What do you know about projectors? If it's this easy to start a business, why would this guy just not run the business himself? Right.

G

Guy Raz35:09

Why are you so confident that you're going to rank highly for these keywords?

T

Tope Awotona35:15

Yeah. So there's a lot of laughter when I share the idea for sure.

G

Guy Raz35:18

All right. So you launch this thing and do any orders come in?

T

Tope Awotona35:24

They do. They do. But then I saw very quickly that the margins were razor thin, right? So you end up selling a $500 projector, maybe you make $5, right?

G

Guy Raz35:35

Why are they so thin?

T

Tope Awotona35:36

Well, one because electronics in general is just very commoditized. And 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, they were making money from the accessories or the light bulbs maybe the lens. I don't remember what all the supplies and parts are which explains why I had no business doing this in the first place. But that's really where the bulk of their profits came from.

G

Guy Raz36:07

So how long did the business last? I would say less than six months.

T

Tope Awotona36:12

Yeah.

G

Guy Raz36:13

So, you lost all that $20,000 investment.

T

Tope Awotona36:16

I did. I did. But it didn't faze me though. I mean, it was disappointing in some ways. Because you put a lot of time and effort into getting it up and running. You sacrifice many late nights, many weekends and you do all that and it doesn't really materialize.

G

Guy Raz36:36

How did you know it was time to just give it up?

T

Tope Awotona36:39

Two things. One, I realized that I didn't really care about projectors, right? So, a few things happened. Whenever people would place orders, 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 the business model was just 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.

G

Guy Raz37:17

So all right. So you kind of leave that behind and did you have an immediate idea after that or did you kind of take some time?

T

Tope Awotona37:26

No, I knew exactly what I wanted to do next.

G

Guy Raz37:28

Wow. What was?

T

Tope Awotona37:31

So I wanted to go back to e-commerce but I thought that this time around I would pick a higher margin product and so I turned around and created another e-commerce website and this time around rather than paying the guy $20,000 I built it all myself.

G

Guy Raz37:47

You built a website and what was the product?

T

Tope Awotona37:50

So I called the website yardsteals.com. Yard steals, like steals like cheap deals for the yard.

G

Guy Raz37:57

Exactly.

T

Tope Awotona37:59

And so the idea was, you know, you can get good deals on home and garden equipment. That was the category I was going after. And what I wanted to do was a few of my co-workers at work were crazy about the Big Green Egg. I'm not sure if you've heard of it before. Sure. The grill. The outdoor 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, right? 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 70 miles from Atlanta, you had to drive to a major city to get it. And so I thought that there's an opportunity there. And I started calling the different manufacturers of these grills. I thought I could build 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 yardsteals.com. And eventually I would build my own, you know, Tope's Blue Egg, whatever you want to call it.

G

Guy Raz40:01

And did you sink another 20 grand into this idea?

T

Tope Awotona40:04

Probably a little less, but I forget the exact amount.

G

Guy Raz40:06

All right. So, you put this up and do orders start to come in?

T

Tope Awotona40:08

Orders start coming in and the margins are better this time. So, instead of making $5 for a $500 purchase, you're making a few hundred on a $700 purchase 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 shipper, and then they would ship out of some warehouse. Exactly. I never saw one. It's just order in and order out. And so I think what I found was I did much better than the first business, right? So I probably netted more grills sold. But I found that the same problem kind of repeated itself. When people come to buy any kind of product, they're not looking just to do the transaction. They're also 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 garden. I just didn't feel like that was my calling.

G

Guy Raz40:28

So when I mean so how long did that last ultimately that business? Right. Once you I mean you essentially had two back-to-back failures. Not. This is a good thing because you're gonna need those in the future. You're going to need to start and fail at a couple 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?

T

Tope Awotona40:51

Yeah. So, this entire time I never quit my day job. So, what I end up doing is I'm still working my day job at that time traveling all over the country. But what I realized was that I started all these different businesses not because I was passionate about solving a problem or 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 idea, I thought that I needed to pick a problem that truly existed and I needed to pick something that I was really excited and committed to being a student of it and I decided that I would basically take a break from starting businesses until I found that idea that checked all those boxes.

G

Guy Raz41:43

All right. So you are doing your day job selling enterprise software and I guess one day from what I understand you start to think about scheduling and calendars. Tell me what happens.

T

Tope Awotona42:00

Yeah. So I was a national account manager and so I managed a number of Fortune 500 accounts in the southeast. 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 companies you're selling to are like the Coca-Colas of the world.

G

Guy Raz42:20

They need to bring 10, 15 people to a meeting.

T

Tope Awotona42:22

And then a lot of times for the deals that we sold we needed to also involve 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 20 people across three different companies and it can be very painful.

G

Guy Raz42:44

It's so painful when you've got like five people who want to do a conference call and there's multiple emails and I can do Wednesday. Yeah, but I'm good on Wednesday. I can't do Wednesday. How about Tuesday? It drives me up the wall.

T

Tope Awotona42:55

It's a common problem and I'm thinking it's 2012 because at this time it's 2012. 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 20 people across three different companies to compare their availability. And I do a search and I find a number of different products on the market that are solving bits and pieces of it, but none that really that I thought did it really, really well.

G

Guy Raz43:25

And you didn't know what that looked like. You were just looking for an option.

T

Tope Awotona43:28

Correct. I just knew that as a consumer, as a potential consumer, I didn't feel like any of the products on the market at the time really checked all the boxes of what I would need.

G

Guy Raz43:38

What was it that you thought you needed?

T

Tope Awotona43:40

Yeah. So, a few things I thought I needed at the time. So, one, there were a lot of products on the market that were really tailored to brick-and-mortar businesses that do a lot of appointments, right? So if you are a salon and you do 100 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 five external meetings a day or three or four, there were no really good options for you. The other thing I noticed was that, as a salesperson, one of the things I knew very well was that just because you want to meet with somebody doesn't mean they want to meet with you, right? And so I thought a lot of the products that existed on the market really spent a lot of time designing for the users of the software and 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 all the users of the product whether they were your own registered users or the people who were receiving invitations from your registered users. Those are some of the things that I noticed.

G

Guy Raz44:48

All right. So you think maybe there's something to this?

T

Tope Awotona44:53

Yes. 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 20 to 30 different products. I used the products religiously 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 their customer service. I would pose as a buyer of their software to understand how they were selling it, how they were 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. And then I thought if you took it to a whole different level and you really lowered the barrier of entry, right, and really democratized it and made it simpler for the more casual schedulers, I thought there was an even bigger opportunity and I just knew that this had to be done.

G

Guy Raz46:14

And how long I mean, how many months does it take before you say to yourself, 'Okay, I've done the research. There's nothing like what I want to make. Maybe I got to 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 decision I'd already made. With this, I led with an open mind. So, I was just as happy to not do it as I would have been to do it. So, I just really let the facts kind of guide me. And I was hoping at the end of 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.' But within the 6 months, I couldn't sleep. It's all I thought about.

It's all you thought about.

T

Tope Awotona47:08

Yeah.

G

Guy Raz47:10

When we come back in just a moment.

N

Narrator47:11

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 Raz and you're listening to How I Built This.

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G

Guy Raz49:22

Hey, welcome back to How I Built This. I'm Guy Raz. So, it's around early 2013 and Tope Awotona 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.

T

Tope Awotona49:41

And so I decide that this needs to happen fast. So it's not really something I can code myself. And so I started going to meetups to see if I can meet other technical co-founders. But that didn't prove to be successful. And so my third option became let me see if I can hire a firm to build an initial product.

G

Guy Raz50:00

You could not find a technical co-founder. You looked around.

T

Tope Awotona50:04

I did. So what happens is this. A lot of people have, everyone has an idea for an app they want to build. And so if you're a talented engineer, you get a lot of terrible pitches every single day. And so most engineers that are entrepreneurial, they would rather pursue their own ideas or if they're going to take their risk, they would rather bet on themselves and kind of go after it. So as easy as it sounds that just because you have an idea, it doesn't mean that you can really attract engineers to get excited about it.

G

Guy Raz50:35

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 you can find a good one, there's a good chance that that engineer wants to start their own business on their own. And they would sort of be like, well, why should I do this with you?

T

Tope Awotona50:52

Exactly. And also, they're also probably well paid at what they do. So, risking all of that to start up a business with some random person.

G

Guy Raz51:01

Exactly. So you could not find a technical co-founder which is a common problem.

T

Tope Awotona51:07

Yeah.

G

Guy Raz51:07

So to make this thing you decided to outsource it to some engineering company that does these things for hire.

T

Tope Awotona51:16

Exactly. So there are lots of companies out there that really help 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 few companies in the states. There was one in Atlanta. There was one in Charlotte. There was one in San Francisco and inevitably the 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 going to pay us. Exactly. And so I kept looking and so I didn't rule those people out, but I ended up finding a company in Ukraine. And from the first interaction that we had, their initial response to me was how much money do you have to put into this idea? 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 wanted to pay attention to them.

G

Guy Raz52:20

This company is called Railsware, I think. Right.

T

Tope Awotona52:22

That's correct.

G

Guy Raz52:23

And did you make any of these companies sign non-disclosure agreements or did you just kind of risk it that you would tell them your idea and hope that they wouldn't copy it?

T

Tope Awotona52:35

No, I did not make them sign any kind of NDAs. Not because I did, ultimately what I believed 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 a number of other people before me had the idea, but I was thinking of executing in a very different way. And I thought my own I guess 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.

G

Guy Raz53:03

I mean that this may be an important point again because it is true a lot of people are paranoid about talking about their ideas but ideas are a dime a dozen and 10, 20, 30 hundred other people may have had the idea that you had thousands may have but it's executing the idea well which is something that you have to believe only you can do.

T

Tope Awotona53:26

Absolutely and you know it's interesting you say that because the other thing that happened is as a scrappy entrepreneur one of the things I tried to propose was, hey, why don't I just give you a cut of the equity and you can work for free. But even they weren't willing to take that risk.

G

Guy Raz53:43

Yeah. Because otherwise they'd never get paid. I mean, everyone is going to be calling them up with every idea.

T

Tope Awotona53:49

That's correct. And so they weren't willing to do it and I fully understand and it worked out well, I guess. So, you hired them to build a prototype of what this could look like, like an MVP, a minimally viable product.

Yes. So, before I hired them, I actually flew over to Kiev to meet with them and we spent two days really brainstorming on the idea. They challenged me in a lot of different ways. I learned a lot from them. But I actually came back to the States initially not thinking that I was going to do the idea. I actually came back from the meeting thinking, man, this is much bigger than I thought. Maybe it's too much to do. But I ended up changing my mind.

G

Guy Raz54:32

Why?

T

Tope Awotona54:33

A few things happened. Around the same time, I found out that my mom's cancer was terminal. And I think it gave me a sense of carpe diem a little bit and just really realizing that who knows how much time we all have, here's my mom and she's dying, would she make the same decision? If she was faced with the same decision, knowing her lifespan, what decision would she make? That really changed my thinking around go for it.

G

Guy Raz55:12

You're thinking, 'Who knows what's going to happen to me tomorrow. Better do this.'

T

Tope Awotona55:16

Correct. Now's the time to do it. Nothing's guaranteed. You can try to wait for the perfect moment, the perfect idea, the perfect development sequence, or you can start with this place and start with what you can do and expand from there.

G

Guy Raz55:33

All right. So, you decide to do this. And how much was it going to cost you to get this prototype built?

T

Tope Awotona55:41

A little over $200,000 is what we thought it would cost.

G

Guy Raz55:44

Wow. Did you have that money?

T

Tope Awotona55:47

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 in my 401k and pay the penalty presumably. I had to 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 Lending Club at a very high interest rate. So, cobbled together my 401k and my savings and then some debt 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.

G

Guy Raz56:26

I mean, that's a really big risk. I mean, yeah, you were what, 31, 32, I guess. So, I still could recover if it was a disaster, but I mean, wow, that's a lot of money. You were basically cleaned out, I'm assuming.

T

Tope Awotona56:41

Yes.

G

Guy Raz56:42

Weren't you nervous?

T

Tope Awotona56:43

Not at all. It sounds crazy to say that now, and it could have been really, really, really bad. And it would have set me back many, many years if it didn't work out, but not at all. And here's why. I've learned a lot from my previous failures. This felt like a, as crazy as it sounds, I felt like I had a calling to do this, right? For a number of reasons. I felt like I spent all my life in sales and I think I really understood. I felt like I knew a lot about meetings and meeting etiquette and what works, what doesn't work. I felt like I actually, unlike the e-commerce businesses that I tried to start, I actually knew a lot about software businesses. And I felt like because I spent so much time researching the space, I felt like I knew exactly what needed to be built to build a great business. So it sounds crazy, but I wasn't scared.

G

Guy Raz57:34

So this is 2013. You put all your money into this product to be built by this company Railsware. Most of that money is 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 Microsoft or whatever.'

T

Tope Awotona58:02

Yeah. So, a few things. So, before I ever met Railsware, I'd actually come up with my own requirements document, right? So, which again, something I didn't do with the previous businesses. So I created my own detailed list of requirements and detailed flows that needed to be built and also my own sequence of how the work needed to be done.

G

Guy Raz58:21

So what were your requirements?

T

Tope Awotona58:23

Oh man, you need to be able to integrate your calendar, be able to specify your availability in all these different ways. You need to be able to guard your availability. And so I thought the user experience and design just needed to be front and center, right? It just needed to be appealing functionally and also aesthetically. We had to get really fancy with how we detected time zones to make it really accurate without the user having to intervene at all. So there are a lot of technical small little technical details that really made a difference in the user experience that we had to figure out.

G

Guy Raz58:58

All right. So you get this product. It takes about six or seven months. Meantime, how is your mom doing? This is 2013.

T

Tope Awotona59:06

Yeah. So she died about 2 months into the development. So she died in June 2013.

G

Guy Raz59:14

Did your mom know much about what you were working on?

T

Tope Awotona59:17

Not really. So I kind of downplayed it to her. So I told her that I was, she knew about the previous businesses and she supported my different business ideas but she wanted me to prioritize my day job. But she thought it was, she thought I was doing really good with my job and that 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 to it.

G

Guy Raz59:50

You never told her.

T

Tope Awotona59:51

I did not.

G

Guy Raz59:52

Because she wanted you to have security and health insurance and all that stuff, right?

T

Tope Awotona59:57

Correct. All the things that she felt like she wanted for her son and she wishes that my dad always provided. Right.

G

Guy Raz1:00:07

So after her death, I mean, how were you able to kind of just because you were in the midst of building this thing like this was intense. I mean, soon after you were in Ukraine again. How did you stay focused?

T

Tope Awotona1:00:23

Yeah. So I poured myself into the business, into the product. And so it was a very, very difficult thing for me. Very difficult for me but Calendly became a huge distraction from that and I just worked like a dog so I didn't have to think about that.

G

Guy Raz1:00:47

So by the fall around September of 2013 the first version of this product is available but you had spent all your money on developing it so how were you going to pay for the servers and pay for get the word out about it. I mean how because you had no money left, right?

T

Tope Awotona1:01:09

Yeah. So I got help along the way through Railsware actually. So a few things happened as Railsware was building the product. They got connected to another potential client, a software company in San Francisco that's gone on and done really well. It's a multi-million dollar business now. And that company was looking to engage them to do some work for them. And so Railsware was like, 'Hey, let's show you this product that we're building, right?' So they showed them Calendly. And at the time, Calendly is not quite ready to be in a public beta, but what ends up happening is they love the product. And so somebody from their 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 K through 12 schools. So a customer success person from this company in San Francisco starts scheduling onboarding calls with the K through 12 schools.

G

Guy Raz1:02:18

Yeah. So, the cat's out of the bag at that point because when you send somebody your Calendly link and they see it, they're like, 'Hey, what's this? I want this, too.'

T

Tope Awotona1:02:30

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 12 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 using it to do onboarding calls to these schools start doing parent teacher conferences with it and then 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 the administrative burden of setting them up, the participation rates. We want to roll this out to all of our teachers.

G

Guy Raz1:03:11

And which school? Where's the school?

T

Tope Awotona1:03:12

In Kentucky. And so they come to me and they say they want to sign up 80 teachers and I just, 80 teachers which at the time was a lot of people.

G

Guy Raz1:03:22

Just to interrupt, what was your business model? How would you make money off of this at that point?

T

Tope Awotona1:03:27

Yeah. So I'm glad you raised that because I neglected to mention that. So because I ran out of money, my idea the business model going into it was to have a 14-day trial so you could use the product for free. No credit card, no feature restrictions for free for 14 days. And at the end of those 14 days, you would have to upgrade with a credit card.

G

Guy Raz1:03:49

And then pay like a subscription fee.

T

Tope Awotona1:03:51

Exactly.

G

Guy Raz1:03:52

Mhm.

T

Tope Awotona1:03:52

But because I ran out of money, we couldn't build the billing features and so by default, the product became 100% free.

G

Guy Raz1:04:00

You couldn't build the billing features.

T

Tope Awotona1:04:03

Correct. Because I ran out of money. I had just enough money to build the scheduling capabilities but not enough money to get around to enforce the billing. So no way to capture revenue from potential users.

G

Guy Raz1:04:17

You couldn't just set up QuickBooks, right?

T

Tope Awotona1:04:20

Well, you can set up QuickBooks, but with an online product, you have to find a way to restrict the features if they're not paying. There's some technical complexity there and some work that needs to be done to turn the features off and on based on their trial status, their payment status, collecting the payments. Initially, to give you an idea, that was maybe 2-3 months of work for two engineers to work on that.

G

Guy Raz1:04:45

Wow. Okay. So, you could not do this. So, you were forced to give this away. Now, but then how were you going to pay for it? I mean, you're giving it away, how are you going to make money? I mean, was the plan to just get a bunch of users and then kind of figure it out? Hopefully, you would get investors.

T

Tope Awotona1:05:02

Yeah. That had to become the idea. So, I was faced with this dilemma. Keep in mind, I'm still working my full-time job this whole time.

G

Guy Raz1:05:09

Your day job. Okay.

T

Tope Awotona1:05:10

So, I hadn't left that. So, this is my side hustle. I was still meeting my obligation to the company. I actually had a really good year that year. And so I felt like so long as it was not interfering with my job, I didn't feel like I needed to disclose it. And so I have this dilemma in which the business is growing in the sense that people are signing up for it and every day the signups are growing because of the virality of the product and because people are getting good value from using the product. But I had no money to turn it into a revenue generating business.

G

Guy Raz1:05:47

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.

T

Tope Awotona1:05:58

Exactly. So the first 300 to 500 signups really came heavily from K through 12. But after that initial wave of K through 12, it spread to all kinds of different industries, to people in all kinds of different roles. It was salespeople, it was recruiters, it was freelancers, it was consultants. It just began to spread like a wildfire.

G

Guy Raz1:06:20

When did you know or when did you feel comfortable leaving your job, your day job?

T

Tope Awotona1:06:25

I wouldn't say so. I don't know that I actually felt comfortable, but I knew that a decision had to be made because, seeing the growth of Calendly, I realized that one, this thing was growing in spite of the fact that I was just doing it part-time and two, I owned 100% of this thing that was growing. And so, to me, the choice was very obvious.

G

Guy Raz1:06:47

And during this time, did you tell anybody about your idea or did you keep it a secret? Like, did you tell your friends about it?

T

Tope Awotona1:06:55

I told my close friends. I definitely told my brothers and my siblings.

G

Guy Raz1:07:00

Did people think it was a good idea?

T

Tope Awotona1:07:01

No, they didn't think so. They thought it was a solved problem. I remember when I was leaving and I told my boss I was leaving. He's like, 'You're leaving for that?' He felt like he failed me that I got desperate and I'm pursuing scheduling. That's a solved problem. Like nobody needs that. But yeah, it was definitely not obvious. I didn't quite know how I was going to fund it. But the decision to me was clear. And so I began to put together a pitch deck and start going to different events trying to meet investors.

G

Guy Raz1:07:39

And at that point you still had not, you were fully funded this thing by yourself.

T

Tope Awotona1:07:42

Funded it myself and ran out of money and then I convinced Railsware to work not for free but to work with understanding that when I raise money I would pay them back. So I was able to get them to work on credit.

G

Guy Raz1:07:57

Wow.

There's a quote of yours I read and I want to read it to you. I'm curious to ask you more about it. Because you described the process of trying to raise money. You said everyone said no. Meanwhile, I watched other people who fit a different profile get money thrown at them for shitty ideas. Those VCs were ignorant and short-sighted. The only thing I could attribute it to was that I was black. Can you walk me through your experience trying to raise money?

T

Tope Awotona1:08:30

Yeah. So, I think first of all, I think it is difficult for pre-revenue businesses in general to raise money, especially in the Southeast, right? Because I think that the farther you are away from the coast, the more investors value revenue, whereas when you're on the coast, I think they care more about growth. So I think that process for anybody is challenging, but I'm sure race plays some aspect in it, but it's not really, there's probably more to it than that.

G

Guy Raz1:09:00

But did you, I mean you didn't really, it sounds like you didn't really pitch to investors at this point yet.

T

Tope Awotona1:09:07

No, I definitely pitched to investors and I did.

G

Guy Raz1:09:09

Yeah.

T

Tope Awotona1:09:09

All in all in Atlanta, the Atlanta area.

G

Guy Raz1:09:13

All in the Southeast.

T

Tope Awotona1:09:14

All in the Southeast. So, a few people in Atlanta, few people in the Southeast. I had a guy from a pretty big firm. Not only did he, so 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 2:00 a.m. to meet with this person and then he stands me up, right? So, just a lot of experiences like that that were just, it's one thing to not invest, but it's another thing to treat people like that.

G

Guy Raz1:09:51

Yeah.

T

Tope Awotona1:09:51

How much of that is just the arrogance of somebody who thinks you're an important VC versus race? I know. Who knows? But I do know that many other entrepreneurs who hadn't made as much progress had more offers than I did.

G

Guy Raz1:10:09

So how did you eventually wind up connecting with people who did want to invest?

T

Tope Awotona1:10:17

Yeah. So I started going to different events. I started connecting with people in the startup community and then I ended up signing up for a membership at a place in Atlanta called the Atlanta Tech Village which is a co-working space specifically for tech startups and while I'm connecting with different investors, the owner of the Atlanta Tech Village catches wind of Calendly. David Cummings is his name and he thinks it's really interesting because he at the time was actually using a competitive product and so he knew firsthand that this was a big problem and he was impressed with what we'd done and so we get connected.

G

Guy Raz1:11:02

Huh. So what happens?

T

Tope Awotona1:11:04

So we have a one or two meetings and he follows up with a term sheet and says I love what you're doing. I think that this can be big. I'd love to invest. I read that it was like $350,000 or something like that. Were you nervous about taking that investment because you owned 100% of this thing, but at the same time, you needed the money.

Yeah. So, I was ambivalent about raising money to be honest with you because I felt like I started the business in the most difficult way possible, really putting 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 some of the ownership. But once I met David, that changed in the sense that I felt like I was going to be working with a successful entrepreneur himself and not just a money man. I felt like I could learn a lot from him and so the ambivalence I had went away once I met him.

G

Guy Raz1:12:11

So it's the spring of 2014 and you get this investment in your business of about $350,000. And how much runway does that give you at that time? I mean was that because I'm assuming the business even in April was like just you, right?

T

Tope Awotona1:12:32

That's right. So, it was just me. I was the only employee and then Railsware. And that ended up giving me something like nine months of runway.

G

Guy Raz1:12:40

And do you remember how many people had you signed up by a year into it by September of 2014?

T

Tope Awotona1:12:50

Maybe about 15,000 at the time.

G

Guy Raz1:12:52

Right. So it's pretty good. And I'm assuming that in that first full year, 2014, you really had to figure out a plan to make this profitable, right, to monetize this.

T

Tope Awotona1:13:01

Yes. And so that became priority number one was I raised the $350,000. Because honestly, I didn't enjoy the fundraising experience and I wanted to make sure that I never really had to do that again. And so I prioritized generating revenue. By August 2014, we turned on billing and introduced a premium plan. And so we start generating revenue in August of 2014.

G

Guy Raz1:13:33

And how did the premium plan work?

T

Tope Awotona1:13:35

Yeah, so that actually created some friction at the time and looking back on it would have done it differently.

G

Guy Raz1:13:41

Part of friction with customers.

T

Tope Awotona1:13:42

Yeah, existing users. And so some portion of the existing user base was disappointed that they had now had to pay for a product that was 100% free, right? But really what the premium plan did was we still had a free product but we just limited what you could do on the free plan and so you had to upgrade to the premium plan to get let's call it 60% of the features you used to be able to get for free before.

G

Guy Raz1:14:08

Right. And what were you charging for it?

T

Tope Awotona1:14:10

$10 monthly if you paid monthly or $96 if you paid annually.

G

Guy Raz1:14:17

And was your idea already at that point that hopefully one day big companies like Microsoft or big companies would use your service.

T

Tope Awotona1:14:29

It absolutely was the plan to eventually begin to acquire larger customers but some of that was already happening. So we were getting pockets of a department in those big businesses using our product.

G

Guy Raz1:14:45

And do you at this point do you just kind of continue to seek out outside investors or do you decide to just see if you can make a go at it through cash flow and revenue.

T

Tope Awotona1:14:58

A little bit of both. So, we start to generate revenue and it definitely extends the runway and I forget exactly how much additional time it gave us, but we ended up raising an additional $200,000 in early 2015 as cushion as an insurance policy of sorts. We ended up not needing it.

G

Guy Raz1:15:18

But we did. Were you ever worried that some big company like Microsoft or Google or somebody else would just come in and with a lot more money and just crush you?

T

Tope Awotona1:15:30

I used to. What I found is that when you spend a lot of time with your customers, you find out that there are a lot of things that they want to do that need to be done that maybe those companies don't have the appetite for doing. As you kind of think about the product you offer, and how technology changes so quickly, I mean, are you thinking like four or five steps ahead of what Calendly might be to make sure that it doesn't become obsolete?

I do and I spend a lot of my time thinking about that. Our overall vision is to take the work out of meetings, right? So we really think about our mission as not just removing the back and forth of scheduling but how can we really automate the entire meeting experience. So too often not only are meetings difficult to schedule, people sometimes forget to show up, when they show up they're not prepared, there's no clear memorialization of the key decisions that are made and action items that are open. Those are the things that we're looking to fix and there's a lot there and that will keep us very busy for 5 years.

G

Guy Raz1:16:44

Would you ever sell a company to a Salesforce or a huge player like that?

T

Tope Awotona1:16:48

Absolutely not. I'm very excited about what we're doing and I feel like we're just getting started and there's a lot to do and so that's not remotely on my radar.

G

Guy Raz1:17:03

When you think about your journey and what you've accomplished, you've had some incredible lows in your life, some failures quite a few, and this just unbelievable success. How much of this do you attribute to your hard work and talent and how much do you think it has to do with just being lucky, being at the right place at the right time?

T

Tope Awotona1:17:27

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 same thing for you. The fact that that didn't happen to you, that's luck. And I look at the family I was born into. I think your family really determines your ceiling in life and your floor as well, like how high and how 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, one that's grown like crazy. So, all those things are definitely luck. But I think we're all lucky but I think what amplifies that luck and what makes one successful is hard work, it's skill, it's resilience, it's an appetite for risk-taking. So that's my view. I think it's a combination of both, but I think when you add those four things, it just takes a whole different level.

G

Guy Raz1:18:26

That's Tope Awotona, founder and CEO of Calendly. In 2020, when I first spoke to Tope, 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 of $3 billion. 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 Rumine Arabie. It was edited by Neva Grant with research help from Darth Gales. Our production staff also includes Casey Herman, Carrie Thompson, John Isabella, Alex Chung, Chris Msini, Carla Estz, Sam Pollson, Malia Agadello, and Katherine Cipher. I'm Guy Raz and you've been listening to How I Built This.

Calendly: Tope Awotona (2020)

About Tope Awotona