Calendly: Tope Awotona (2020)

After emigrating from Nigeria to the US to attend college, Tope Awotona worked as a door-to-door salesman and eventually set out to become a tech entrepreneur. He launched a series of e-commerce businesses that quickly fizzled when he realized he had no passion for them. But then he landed on an idea he was truly excited about: designing software that would minimize the hassle and headache of scheduling meetings. In 2013, he cashed in his 401k and went into debt to build Calendly, a scheduling service reportedly doing over $100 million in revenue. This episode was produced by Rachel Faulkner-White, with music by Ramtin Arablouei Edited by Neva Grant, with research help from Daryth Gayles. You can follow HIBT on Twitter https://twitter.com/HowIBuiltThis & Instagram https://www.instagram.com/howibuiltthis, and email us at [email protected] mailto:[email protected]. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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

• 0:00Guy Raz?

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• 0:46Guy Raz?

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• 1:32Guy Raz?

  Say you're 18 months in. Business is growing. You've got expenses coming from six directions. Gas for the van, office supplies, your phone bill, team lunches that are actually client meetings, and you're putting it all on whatever card you grabbed in year one. You're not thinking about it. Why would you? You've got bigger problems. But here's the thing. Path A, you keep going like that. End of the year, you're sorting through statements, trying to figure out what went where. You've left hundreds, maybe thousands, on the table in rewards you never earned, money that could have gone back into the business. Path B, you pause and get the US Bank Triple Cash Rewards Visa Business Card. Now, you're earning 3% cash back

• 2:16Guy Raz?

  on gas and EV charging, office supply stores, cellphone service, and restaurants. You pick up an extra $750 cash back as a bonus. And you've got a low APR on purchases and balance transfers for 12 months while you're scaling. Same business, same expenses, two completely different outcomes based on one small decision. Visit usbank.com/business to learn more. The creditor and issuer of this card is US Bank National Association, pursuant to a license from Visa USA, Inc. Some restrictions apply. If you travel often, you'll want to hear about this unprecedented offer. For the first time ever,

• 3:00Guy Raz?

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• 3:45Guy Raz?

  or bring a guest to the Delta Sky Club. Make every trip feel more rewarding with the car that upgrades your travel. Apply today at delta.com/cardsocial. Offer ends November 4, 2026. Minimum spending requirements and terms apply. Flights are fulfilled as flight certificates valid for Delta Comfort or Delta Maine to select domestic destinations. Book 21-plus days in advance. Up to $80 per person and taxes and fees apply. Other restrictions apply. When I pull up to a gas pump to fill my car, I'm not thinking about chemistry or engineering. I'm thinking about getting in, filling up, and getting on with my day. And it reminds me a little bit of the founders I talk to on this show, because the best

• 4:27Guy Raz?

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• 5:10Guy Raz?

  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 Owatana's name is pronounced "tope." That's how he pronounces it. And I know some of you from Nigeria think it might be pronounced "tope." Nope, he pronounces it "tope." So, without further ado, here's the show.

• 5:57Guy Raz?

  How much was it going to cost you to get this prototype built?

• 6:00Speaker 01

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

• 6:03Guy Raz?

  Wow.

• 6:04Speaker 01

  So I had to empty every single dollar in my 401K, use every single dollar in my savings account. I had to borrow a little bit on top of that. I ended up borrowing a little bit from Linden Club.

• 6:15Guy Raz?

  At a high interest rate?

• 6:16Speaker 01

  At a very high interest rate and maxed out all my credit cards and put it all in on this idea that at the time didn't even have a name.

• 6:31Guy Raz?

  Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.

• 6:43Guy Raz?

  I'm Guy Raz, and on the show today, how Tope Awotona turned his frustration with scheduling meetings into Calendly, a multimillion-dollar business that makes setting up a meeting quick and simple.

• 7:01Guy Raz?

  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 no's? It comes from practice. Think about previous guests we've had on this 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 hear hundreds and hundreds of people tell them "no" over and over again.

• 7:45Guy Raz?

  Same thing with entrepreneurs like Davis Smith, who built Cotopaxi, and David Neleman 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. Tope also spent his early years as a salesman. First, door to door, selling alarm systems, and later, doing million-dollar

• 8:28Guy Raz?

  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, Tope 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

• 9:11Guy Raz?

  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 $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 Tope's earliest years. He's Nigerian, and he spent his childhood in Africa, growing up in the suburbs of Lagos.

• 9:52Guy Raz?

  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 was pretty great.

• 10:02Speaker 01

  Yeah, so, lived in a number of different places, but where I lived for 12 years, you'd call it like a lower upper-class neighborhood in that part of the world. Knew all of our neighbors, was 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.

• 10:42Guy Raz?

  Were you a well behaved kid?

• 10:44Speaker 01

  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.

• 10:54Guy Raz?

  Were your parents strict?

• 10:55Speaker 01

  Uh, my mom was. My dad was not so much. They could not have been more opposite.

• 11:00Guy Raz?

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

• 11:04Speaker 01

  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.

• 11:14Guy Raz?

  Was, um, were you a pretty good student as a, as a little kid?

• 11:17Speaker 01

  I'd say so. Very good, I'd say.

• 11:19Guy Raz?

  Was that something that your parents stressed at home? Education?

• 11:21Speaker 01

  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. And I didn't know what Harvard was, but I know that my mom thought it was important.

• 11:45Guy Raz?

  And when you were little, like eight, nine, 10, 11, would people talk about you as a, as a smart kid? Or they say, oh, there's Tope, he's really smart. Or, or did you just feel like just everyone you knew was pretty good at school?

• 11:58Speaker 01

  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. You know, like in primary school. And I think that's when I, I knew. 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.

• 12:26Guy Raz?

  I guess when you were 12 years old, um, your father, your father was tragically killed.

• 12:34Guy Raz?

  And I.

• 12:37Guy Raz?

  I can't imagine what that was like for your brothers and your mom. What do you remember about that time, about how you felt?

• 12:45Speaker 01

  I remember that it changed everything I thought I knew. So as a kid, I, you know, my dad was my hero, right?

• 12:56Speaker 01

  And, you know, because when you're 12 and your dad lets you get away with everything, he's your favorite parent.

• 13:02Guy Raz?

  Yeah.

• 13:02Speaker 01

  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. I became an insomniac at the age of 12.

• 13:19Speaker 01

  These are things I now recognize that are, you know, signs of trauma, but at the time I didn't really recognize it.

• 13:26Guy Raz?

  You were 12 years old when your father died.

• 13:31Guy Raz?

  And you were there. You saw his death.

• 13:35Speaker 01

  I did.

• 13:36Guy Raz?

  It was a robbery, essentially.

• 13:38Speaker 01

  A carjacking.

• 13:40Guy Raz?

  I can't imagine how you were 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 kind of went back to school and kind of carried on.

• 13:53Speaker 01

  I did. I did. You know, I think some of that is the Nigerian way, to be honest with you. But I also think within that, my mom had a very, my mom was a very strong and resilient person. And, you know, one of the things I really appreciate about the Nigerian culture is really everybody's your family, right? Even your family, friends are essentially think of themselves as your family.

• 14:20Speaker 01

  So I think she was able to, you know, a lot of people rallied around her and supported her, but she definitely, it was a very, very difficult time for her. But I think she also really wanted us to...

• 14:36Speaker 01

  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 is proceed with our lives. That's what would make our dad proud.

• 14:47Guy Raz?

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

• 15:02Speaker 01

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

• 15:27Guy Raz?

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

• 15:39Speaker 01

  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 at that, in 96.

• 15:52Guy Raz?

  You had family already in the US?

• 15:54Speaker 01

  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.

• 16:04Guy Raz?

  Where did you move to?

• 16:06Speaker 01

  Marietta, Georgia.

• 16:07Guy Raz?

  And what was the plan that you would go to university? I mean, you'd finished high school. So what was that the plan?

• 16:13Speaker 01

  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, Marietta. I went there for two years.

• 16:25Guy Raz?

  And, and I hear, 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 a completely different world for you?

• 16:40Speaker 01

  Oh, absolutely. 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. And that was very different here, you know, 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.

• 17:20Guy Raz?

  Yeah. I mean, do you remember, I mean, 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 a sort of jarring or something that you, you didn't expect when you arrived?

• 17:43Speaker 01

  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 two years younger than most of the kids. And so I'd 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.

• 18:17Guy Raz?

  All right. So here you are and you graduate high school. So presumably this, at this point, you know, you're, 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, you decide to go to the University of Georgia initially, is that right?

• 18:35Speaker 01

  Correct.

• 18:36Guy Raz?

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

• 18:39Speaker 01

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

• 18:44Guy Raz?

  And why, and why computer science?

• 18:46Speaker 01

  Yeah, so I picked computer science for, for two reasons. So back in 95, Windows 95 was launched and that really opened my eyes. I just saw all these grown adults, you know, 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 in my little teenage mind, I started to connect the dots around, maybe this is where the world is going.

• 19:14Guy Raz?

  So when you got to the University of Georgia, I mean, this is like 98, I guess.

• 19:19Speaker 01

  98.

• 19:19Guy Raz?

  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?

• 19:26Speaker 01

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

• 19:33Guy Raz?

  And how were you, did you work while you were a student as well?

• 19:36Speaker 01

  I did. So I initially worked at CVS.

• 19:43Guy Raz?

  Like as a cashier?

• 19:44Speaker 01

  Yeah, as a cashier. But then I, 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.

• 19:56Guy Raz?

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

• 19:59Speaker 01

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

• 20:03Guy Raz?

  Wow. This is while you were a student, like during the summertime?

• 20:06Speaker 01

  Yeah, yes, it was a summer job. Talk about like the most difficult job ever. I would knock on people's doors at, you know, right before dinnertime.

• 20:17Speaker 01

  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.

• 20:22Guy Raz?

  And, and were you doing this in, in Athens, Georgia?

• 20:25Speaker 01

  Correct. So in Athens, Georgia. So we would go knock on doors for three, four hours and try to make a sale. And what would happen was, the job was strictly commissioned, right? So which is, you know, you could potentially work all week, all month.

• 20:40Guy Raz?

  And make nothing?

• 20:41Speaker 01

  Yeah, that's right.

• 20:42Guy Raz?

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

• 20:45Speaker 01

  I did, I did. So what happened was, my very, very first day, I sold two alarm systems, which, you know, allowed me to make $500. Which at age, you know, 19, that's, that was a lot of money to me.

• 21:00Guy Raz?

  Yeah, it's great money.

• 21:01Speaker 01

  It was the most money I'd ever made in a day. And interestingly, the rest of the week, I did not sell anything. And so

• 21:10Speaker 01

  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 I would, you know, how my career would have changed. But that's what happened.

• 21:23Guy Raz?

  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?

• 21:32Speaker 01

  I liked it.

• 21:35Speaker 01

  And I'll tell you why I liked it, because of those first two days.

• 21:37Guy Raz?

  Because you made the money?

• 21:38Speaker 01

  Yeah. 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 weren't happy 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. The other thing I really liked was it was the first time like I could, I could really influence how much money I made. I could work harder, I could improve my skill and not wait six months, 12 months to make more money. I could make more money the next day, the next week.

• 22:19Guy Raz?

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

• 22:23Speaker 01

  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 any electoral 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? That was fulfilling in a way.

• 22:50Guy Raz?

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

• 22:56Speaker 01

  No, far from it. I think one of the things I've learned, you know, myself, you know, many, 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, you know, my parents would have known to, I mean, I, you know, 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 think there's, I am probably more savvy about how those things work today.

• 23:37Guy Raz?

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

• 23:58Speaker 01

  You know, it took me a while to, you know, there was a little bit of an adjustment, right? I'd 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 CIOs. So I got exposed to a much more complicated, a much more sophisticated sales process. But I loved it. I found myself not really, like, I enjoy the work I did, but, you know, I've always been a very, very impatient person. And so, you know, 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 in an accelerated path.

• 24:42Speaker 01

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

• 25:09Guy Raz?

  So you leave and what did you find?

• 25:15Speaker 01

  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 software to manage paper files, right? So digital files and manage the approval workflows around it.

• 25:31Guy Raz?

  So this is like B to B stuff, right?

• 25:33Speaker 01

  Yeah. And so I really enjoyed working for the company. But while I was at the company, part of the onboarding process is you get 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.

• 25:51Guy Raz?

  Why?

• 25:51Speaker 01

  You know, it was the first time I heard about the founding story of a company, of a successful company. Because before then, I thought that most people who started in a 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 their 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.

• 26:24Speaker 01

  And the reason that that business 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 realize that, you know, entrepreneurship was way more attainable than I thought it was before that. So I thought I had to be, you know, I just, yeah, it's 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, I started, it kind of rekindled this very, you know, this latent idea that I had of becoming a tech entrepreneur.

• 27:05Speaker 01

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

• 27:12Guy Raz?

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

• 27:32Guy Raz?

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• 28:59Guy Raz?

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• 29:44Guy Raz?

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• 30:03Speaker 02

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• 31:10Guy Raz?

  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.

• 31:23Speaker 01

  My mom was really 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. 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 she was just in a, 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.

• 32:04Speaker 01

  And so that kind of accelerated the decision to, to come back to Atlanta.

• 32:10Guy Raz?

  Was it also a software company?

• 32:11Speaker 01

  Yes, it was another software company doing a very similar thing, but for a, you know, as in selling enterprise software, but selling it to, to a different industry.

• 32:21Guy Raz?

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

• 32:25Speaker 01

  That's correct.

• 32:26Guy Raz?

  And I guess while you were there, you meet, you meet like this business contact who I know the whole story, but he starts giving you ideas for how you can like start your own company?

• 32:38Speaker 01

  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, 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 started a business selling light bulbs?

• 33:20Speaker 01

  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.

• 33:26Guy Raz?

  Okay, I got you, yeah.

• 33:27Speaker 01

  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.

• 33:45Guy Raz?

  That people are searching for.

• 33:46Speaker 01

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

• 33:52Guy Raz?

  And what did he come up with?

• 33:54Speaker 01

  He came back with projectors.

• 33:56Guy Raz?

  Projectors?

• 33:57Speaker 01

  Projectors, yep.

• 33:58Guy Raz?

  Like, like slide projectors?

• 34:01Speaker 01

  Yes.

• 34:01Guy Raz?

  Or video projectors?

• 34:03Speaker 01

  Movie projectors.

• 34:05Guy Raz?

  Movie projectors.

• 34:05Speaker 01

  Yeah, there were actually six specific keywords. It was HD projectors, it was movie projectors. I forget what the other four were now. So there's, there's a ton of search traffic looking for movie projectors. And then you analyze the sites that are currently ranked high for that keyword. And then you look at how displacable they are, basically. And you know, his instincts were that they were easily replaceable that you could with three, six months of work, you could be, you could be at the highest rank in site for for that keyword.

• 34:36Guy Raz?

  So do you, did you start a projector company?

• 34:39Speaker 01

  I did. I'd never used a projector in my life, right?

• 34:42Guy Raz?

  Yeah.

• 34:43Speaker 01

  Maybe you, maybe seen a few in a different meetings, right? But I never really bought one before, set it one up before, but the analysis seemed compelling to me. And so we started a projector business and we called it projectorspot.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 the, we didn't actually go out and buy projectors and sell them on the website. We established dropshipping relationships with different wholesalers. And in the space of, you know, two to three months or so, we launched the business.

• 35:19Guy Raz?

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

• 35:23Speaker 01

  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.

• 35:35Guy Raz?

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

• 35:41Speaker 01

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

• 35:47Guy Raz?

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

• 35:54Speaker 01

  I did and they all laughed.

• 35:56Guy Raz?

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

• 36:02Speaker 01

  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, why would this guy just not run the business himself? Why are you so confident that you're going to rank highly for these keywords? Yeah. So there's a lot of laughter when I share the idea for sure.

• 36:21Guy Raz?

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

• 36:26Speaker 01

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

• 36:37Guy Raz?

  Why are they so thin?

• 36:38Speaker 01

  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, I forget what, you know, 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.

• 37:09Guy Raz?

  So how long did the business last?

• 37:11Speaker 01

  I would say less than six months.

• 37:14Guy Raz?

  Ooh.

• 37:14Speaker 01

  Yeah.

• 37:15Guy Raz?

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

• 37:19Speaker 01

  I did. I did. But I wasn't, it didn't faze me that many. It was disappointing in some ways.

• 37:25Guy Raz?

  Yeah.

• 37:26Speaker 01

  Because I had, you know, because 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.

• 37:39Guy Raz?

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

• 37:42Speaker 01

  Two things. One, I realized that I didn't, I just didn't really care about projectors. Right? So what I, a few things happened, right? So whenever people would place orders, 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, 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.

• 38:20Guy Raz?

  So, all right, so you, you kind of leave that behind. And did you have an immediate idea after that? Or did you kind of take some time?

• 38:29Speaker 01

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

• 38:31Guy Raz?

  Wow. What was?

• 38:33Speaker 01

  So I wanted to go back to e-commerce.

• 38:37Speaker 01

  And 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.

• 38:50Guy Raz?

  You built a website and and what was the product?

• 38:53Speaker 01

  So I called the website yardsteals.com.

• 38:56Guy Raz?

  Yard steals, like steals, like cheap deals for the yard.

• 38:59Speaker 01

  Egg, exactly.

• 39:00Guy Raz?

  Okay.

• 39:01Speaker 01

  And so the idea was, you know, you can get good deals on home and garden equipment. That was the category that I was going after. And what I wanted to do was I, a few of my coworkers at work were crazy about the big green egg. I'm not sure if you've heard of it before.

• 39:19Guy Raz?

  Sure, the grill, the outdoor grill.

• 39:20Speaker 01

  Yeah, so ceramic grill and people were 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 70 miles from Atlanta, you had to drive to a major city to get it. And so I thought that, I thought there's an opportunity there. And I started calling the different manufacturers of these 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, to yardsteals.com.

• 40:05Speaker 01

  And eventually I would go start my own, I would build my own, you know, Topps Blue Egg, whatever you want to call it.

• 40:14Guy Raz?

  And did you sink another 20 grand into this idea?

• 40:17Speaker 01

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

• 40:21Guy Raz?

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

• 40:24Speaker 01

  Orders start coming in and the margins are better this time. So instead of making, you know, like $5 for a $500 purchase, you're making a few hundred dollars on a $700 purchase or something like that. So much better margins.

• 40:38Guy Raz?

  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.

• 40:45Speaker 01

  Exactly. Yeah, 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, um, you know, probably netted, uh, sold more grills, one. But I think this, 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, 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 had 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.

• 41:30Guy Raz?

  So when, I mean, so how long did that last ultimately, that business?

• 41:35Speaker 01

  Probably about the same, three to six months, I would say.

• 41:37Guy Raz?

  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 gonna need to start and fail a couple of businesses. Did you think, maybe I'll take a break from starting a business for a while and go back and just get a safe job?

• 41:54Speaker 01

  Yeah. So this entire time, I never quit my day job. So what I ended 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 started all these different businesses, not because I was passionate about solving 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 needed to pick 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.

• 42:38Speaker 01

  And I decided that I would basically take a break from starting businesses until I found, until I found that idea that checked all those boxes.

• 42:46Guy Raz?

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

• 43:02Speaker 01

  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, like the kind of companies you're selling to are like the Coca Colas of the world. So they need to bring 10, 15 people to a meeting. And then a lot of times for the deals that we sold, we needed to also involve systems integrators. 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.

• 43:47Guy Raz?

  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, if I'm good on Wednesday, I can't do Wednesday. How about Tuesday? It drives me up the wall.

• 43:58Speaker 01

  It's a common problem. And I'm thinking it's 2012 because at this time is 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.

• 44:28Guy Raz?

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

• 44:31Speaker 01

  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. What I would need.

• 44:40Guy Raz?

  What was it that you thought you needed?

• 44:42Speaker 01

  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. So if you're 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, you know, five external meetings a day or three or four, there are no really good options for you. The other thing I noticed was that, you know, as a salesperson, one of the things I knew very well was that just because you want to meet with somebody, it 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

• 45:26Speaker 01

  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 every, 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, that I noticed.

• 45:51Guy Raz?

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

• 45:56Speaker 01

  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, you know, 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're 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 loved what they did.

• 46:41Speaker 01

  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 lower the barrier of entering, 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.

• 47:16Guy Raz?

  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 want to make. Maybe I gotta, I gotta do this.

• 47:28Speaker 01

  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, to do it. So I just really let the fact kind of 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. But it's been a six months. I, I couldn't sleep. That's all I thought about.

• 48:09Guy Raz?

  It's all you thought about?

• 48:10Speaker 01

  Yeah.

• 48:12Guy Raz?

  When we come back in just a moment, White Oak 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.

• 48:37Speaker 04

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• 49:47Guy Raz?

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

• 50:07Speaker 01

  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.

• 50:26Guy Raz?

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

• 50:29Speaker 01

  I did. So what happens is this, a lot of people have, you know, everyone has an idea for an app they want to build. And so if you're a talented engineer, you get, 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 the risk, they're rather like bet on themselves and kind of go after it. So as, as easy as it sounds, that, you know, just because you have an idea, it doesn't mean that you can really attract, get engineers to get excited about it.

• 51:00Guy Raz?

  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, 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?

• 51:16Speaker 01

  Exactly. And also, you know, they're also probably well-paid at what they do. So, you know, kind of, you know, risk and all of that to...

• 51:24Guy Raz?

  To start up a business with some random person.

• 51:27Speaker 01

  Exactly.

• 51:28Guy Raz?

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

• 51:31Speaker 01

  Yeah.

• 51:32Guy Raz?

  So to make this thing, you decided to like outsource it to like a some, you know, engineering company that does these things for hire?

• 51:41Speaker 01

  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-

• 52:10Guy Raz?

  How much are you going to pay us?

• 52:11Speaker 01

  Exactly.

• 52:13Guy Raz?

  Yeah.

• 52:13Speaker 01

  And so I kept looking, and so I didn't rule those people out. But I ended up getting, finding a company in Ukraine. And from the first interaction that we had, you know, their initial, their initial response to me was, how much budget, how much budget, how much money do you have to put into this company, to this idea? Their first response back was, we think this is a great opportunity to, 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, to them.

• 52:45Guy Raz?

  This company's called Railsware, I think, right?

• 52:47Speaker 01

  That's correct.

• 52:48Guy Raz?

  And, and did you, I mean, did you make any of these companies sign like 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?

• 53:00Speaker 01

  No, I didn't, I did not make them sign any kind of NDAs. Not because I did, you know, ultimately what I believed was, and it's still what I believe today, is I think the key to its success is the execution of it, not so much just the idea. Because, you know, a number of other people before me had had 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.

• 53:29Guy Raz?

  I mean, 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 a dozen. And 10, 20, 30, 100 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.

• 53:51Speaker 01

  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, and you can work for free. But even they weren't willing to take that risk.

• 54:08Guy Raz?

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

• 54:14Speaker 01

  That's correct. And so they weren't, they weren't willing to do it, which I fully understand. And, uh, but it worked out well, I guess.

• 54:21Guy Raz?

  So you hired them to build a prototype of what this could look like, like an MVP, a minimally viable product?

• 54:29Speaker 01

  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, 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, maybe it's too much to do. But I ended up changing my mind.

• 54:58Guy Raz?

  Why?

• 54:59Speaker 01

  A few things happened. Around the same time, I found out that my mom's cancer was terminal.

• 55:07Speaker 01

  And I think it gave me a sense of Carpe Diem a little bit. And just really realizing that, you know, who knows how much time we all have. You know, like, here's my mom and, you know, and that she's dying.

• 55:24Speaker 01

  Would she make the same decision? If she was faced with the same decision, knowing her lifespan, how, what decision would she make?

• 55:32Speaker 01

  That really changed my thinking around.

• 55:36Speaker 01

  Go for it.

• 55:37Guy Raz?

  You're thinking, who knows what's gonna happen to me tomorrow? Better do this.

• 55:41Speaker 01

  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.

• 55:59Guy Raz?

  Alright, so you decide to do this. And how much was it gonna cost you to get this prototype built?

• 56:06Speaker 01

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

• 56:09Guy Raz?

  Wow. Did you have that money?

• 56:12Speaker 01

  I had most of it, but it required doing a lot of things that tell you not to do. So I had to empty every single dollar in my 401K.

• 56:20Guy Raz?

  And pay the penalty presumably?

• 56:22Speaker 01

  Yep. 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 Linden Club.

• 56:32Guy Raz?

  At a high interest rate?

• 56:33Speaker 01

  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.

• 56:51Guy Raz?

  I mean, that's a really big risk. I mean, you were what, 31, 32, I guess? So you 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?

• 57:06Speaker 01

  Yes.

• 57:07Guy Raz?

  Weren't you nervous?

• 57:08Speaker 01

  Not at all. It sounds crazy to say that now. It could've been really, really, really bad. And it would've set me back 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, you know, 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 I, because I spent so much time researching the space,

• 57:51Speaker 01

  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.

• 58:00Guy Raz?

  So this is 2013. You put all your money into this product to be built. This for 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 or Microsoft or whatever.

• 58:26Speaker 01

  Yeah, so a few things. So before I ever met Railsware, I'd actually come up with my own requirements document.

• 58:32Guy Raz?

  Okay.

• 58:33Speaker 01

  So which, again, something I didn't do with the previous businesses. So I had, I created my own detailed 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.

• 58:47Guy Raz?

  So what were your requirements?

• 58:48Speaker 01

  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, you know, 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 with how we detected time zones to make it really, really accurate without the user having to, you know, 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.

• 59:22Guy Raz?

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

• 59:31Speaker 01

  Yeah, so she died about two months into the into the development. So she died in June 2013.

• 59:37Guy Raz?

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

• 59:41Speaker 01

  Not really. So I kind of downplayed it to her. So I told her that I was, you know, she knew about she knew about the previous businesses and she she supported my my different business ideas, but she wanted me to.

• 59:58Speaker 01

  She wanted me to prioritize my, my day job.

• 1:00:02Speaker 01

  But she thought it was, you know, it was, she thought I was doing really good with my job and that she didn't lose, 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.

• 1:00:15Guy Raz?

  You never told her?

• 1:00:16Speaker 01

  I did not.

• 1:00:18Guy Raz?

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

• 1:00:22Speaker 01

  Correct. All the things that she felt like, you know, she wanted for her son and she wishes that, you know, that my dad always provided, right?

• 1:00:30Guy Raz?

  Yeah. 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, you were in Ukraine again. How'd you stay focused?

• 1:00:48Speaker 01

  Yeah, so I, I poured myself into the, into the business, into the product. And so, you know, it was a very, very, very difficult thing for me, very, very difficult thing for me. But Calendly became a huge distraction from that. And I just, I worked

• 1:01:08Speaker 01

  like a dog, just so I didn't have to think about that.

• 1:01:12Guy Raz?

  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, I don't know, pay for the servers and pay for, I mean, get, get the word out about it. I mean, because you had no money left, right?

• 1:01:34Speaker 01

  Yeah, so I got, you know, 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 to a multi hundred million dollar business now. And that company was looking to engage them to do some work for them. And so Railsware was was like, hey, let's show you this product that we're building. Right? So they show them Calendly. And at the time, Calendly is not quite, it's in a, it's not quite ready to be in a public beta. But what it what it ends up happening is they love the product.

• 1:02:18Speaker 01

  And so somebody from their 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

• 1:02:32Speaker 01

  K two, K three, 12 schools. So a customer success person from this company in San Francisco starts scheduling onboarding calls with K three, 12 schools.

• 1:02:43Guy Raz?

  Yep.

• 1:02:44Speaker 01

  So the cat's out of the bag at that point.

• 1:02:46Guy Raz?

  Because when you send somebody your Calendly link and they see it, they're like, hey, what's this? I I want this too.

• 1:02:55Speaker 01

  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 three, 12, 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 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. We want to roll this out to all of our teachers.

• 1:03:36Guy Raz?

  Which school? Where's the school?

• 1:03:37Speaker 01

  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 now.

• 1:03:47Guy Raz?

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

• 1:03:52Speaker 01

  Yeah. So I'm glad you raised that because I neglected to mention that. So because I ran out of money.

• 1:03:58Speaker 01

  No, my, my idea, uh, the business model going into it was to, 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.

• 1:04:14Guy Raz?

  And then pay like a subscription fee.

• 1:04:16Speaker 01

  Exactly. But because I ran out of money, we couldn't build the, the billing, uh, features. And so by default, the product became a hundred percent free.

• 1:04:25Guy Raz?

  You couldn't build the billing features?

• 1:04:28Speaker 01

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

• 1:04:42Guy Raz?

  You couldn't just like set up, I guess you can't really set up QuickBooks, right?

• 1:04:45Speaker 01

  Well, you can set up QuickBooks, but it's within the online product, you have to find a way to restrict the fe- features if they're not paying.

• 1:04:52Guy Raz?

  Yeah.

• 1:04:52Speaker 01

  You know, there's some technical complexity there and some work that needs to be done to, uh, to kind of 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 maybe two, three months of work for two engineers to work on that.

• 1:05:10Guy Raz?

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

• 1:05:27Speaker 01

  Yes, so that, that had to become the idea. So I, I was faced with this dilemma. So keep in mind, I'm still working my, I'm still working my full-time job this whole time.

• 1:05:34Guy Raz?

  Your day job? Okay.

• 1:05:35Speaker 01

  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, I actually had a really good year that year.

• 1:05:45Speaker 01

  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.

• 1:05:53Speaker 01

  And so I had this dilemma in which the business is growing, you know, in the sense that people are signing up for it. And every time, um, every day the signups are growing because of the virality of the product and because people, people are getting good value from using the product. But I had no. I didn't have the money to turn it into a revenue generating business.

• 1:06:13Guy Raz?

  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?

• 1:06:23Speaker 01

  Exactly. So the first, you know, 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. It spread to people in all kinds of different roles. It was salespeople, it was recruiters, it was freelancers, it was consultants.

• 1:06:42Speaker 01

  It just began to spread like a wildfire.

• 1:06:45Guy Raz?

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

• 1:06:50Speaker 01

  I wouldn't say, so I don't know that I actually felt comfortable, but I, I knew that a decision had to be made because I, you know, seen 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.

• 1:07:12Guy Raz?

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

• 1:07:20Speaker 01

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

• 1:07:25Guy Raz?

  Did people think it was a good idea?

• 1:07:26Speaker 01

  No, they didn't think so. They thought it was a solved problem. I remember when I, when I was leaving and I told my boss I was leaving. He's like, you're leaving for that?

• 1:07:38Speaker 01

  He felt like he'd failed me that I, you know, like he felt like I was, like I got desperate and I, you know, and I'm pursuing, you know, scheduling. That's a solved problem. Like, nobody needs that. But yeah, it was not, it was definitely not obvious. I didn't quite know how I was going to fund it, but I, 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.

• 1:08:04Guy Raz?

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

• 1:08:09Speaker 01

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

• 1:08:25Guy Raz?

  There's a quote of yours I read and I want to read it to you.

• 1:08:30Guy Raz?

  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 shortsighted. The only thing I could attribute it to was that I was black. Can you walk me through your experience trying to raise money?

• 1:08:54Speaker 01

  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.

• 1:09:25Guy Raz?

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

• 1:09:32Speaker 01

  No, I definitely pitched to investors.

• 1:09:33Guy Raz?

  You did?

• 1:09:34Speaker 01

  Yeah, and I got...

• 1:09:36Guy Raz?

  All in Atlanta, the Atlanta area?

• 1:09:38Speaker 01

  All in the Southeast. So a few people in Atlanta, a 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 AM 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 kind of treat people like that.

• 1:10:16Guy Raz?

  Yeah.

• 1:10:16Speaker 01

  How much of that is just the arrogance of somebody who thinks they're an important VC versus race? Who knows? But I mean, I do know that many other entrepreneurs who didn't have as much... Who hadn't made as much progress...

• 1:10:32Speaker 01

  Had more offers than I did.

• 1:10:34Guy Raz?

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

• 1:10:42Speaker 01

  Yeah, so I I started going to different events. I got started connecting with people in the startup community. And then I ended up signing up for a membership at a at a place in Atlanta called the Atlanta Tech Village, which is a it's a cool working space specifically for tech startups. And it's while I'm connecting with different investors that the the owner of the Atlanta Tech Village catches wind of Calendly. David Cummins is his name. And he thinks it's really interesting because he, at the time, he 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.

• 1:11:28Guy Raz?

  Huh. So what happens?

• 1:11:30Speaker 01

  So we have a one or two meetings, and he follows up with a term sheet and says, I'm I love what you're doing. I think that this is this can be big. I'd love to invest.

• 1:11:43Guy Raz?

  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?

• 1:11:52Speaker 01

  Yeah, so I was ambivalent about raising money, to be honest with you, because, you know, I felt like I started the business, you know, the most difficult way possible, you know, really, you know, 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, you know, cede, you know, some of the ownership. But once I met David, that changed, in the sense that like, I felt like I was going to have a

• 1:12:21Speaker 01

  when I was going to be, you know, working with a successful entrepreneur himself and not just a a money man, right? I felt like I could learn a lot from from him. And so the ambivalence I had went away once I, once I met him.

• 1:12:36Guy Raz?

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

• 1:12:57Speaker 01

  That's right. So it was just me. I was the only employee and then, you know, where else were, and so that ended up giving me, I want to say something like nine months of runway.

• 1:13:05Guy Raz?

  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 2014?

• 1:13:15Speaker 01

  Maybe about 15,000 at the time.

• 1:13:17Guy Raz?

  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.

• 1:13:26Speaker 01

  Yes. And so that became, you know, priority number one, once I raised the $350,000. Because honestly, I, I didn't enjoy the fundraising, raising experience.

• 1:13:37Guy Raz?

  Yeah.

• 1:13:37Speaker 01

  And I wanted to make sure that I was, I never really had to do that again. And so I prioritized generating revenue. By August 2014, we'd turned on billing and introduced a premium plan. And so we start generating revenue in August of 2014.

• 1:13:58Guy Raz?

  And how did the premium plan work?

• 1:14:00Speaker 01

  Yeah. So that actually created, it created some friction at the time. And, you know, looking back on it, we would have done it differently.

• 1:14:05Guy Raz?

  Create friction with customers?

• 1:14:08Speaker 01

  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 a hundred percent free.

• 1:14:17Guy Raz?

  Right.

• 1:14:18Speaker 01

  But really what the, what the premium plan did was he basically, 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 maybe get for free before.

• 1:14:33Guy Raz?

  Right. And what was, what were you charging for it?

• 1:14:36Speaker 01

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

• 1:14:42Guy Raz?

  And was your idea already at that point that hopefully one day, big companies like Microsoft or, you know, Microsoft, but like, you know, big companies would, would use your, your service?

• 1:14:55Speaker 01

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

• 1:15:10Guy Raz?

  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 go at it, you know, through cash flow and revenue?

• 1:15:23Speaker 01

  A little bit of both. So we started 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. That's cushioned as an insurance policy of sorts. We ended up not needing it.

• 1:15:43Guy Raz?

  Wow.

• 1:15:43Speaker 01

  But we did.

• 1:15:44Guy Raz?

  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, you know, and just crush you?

• 1:15:55Speaker 01

  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 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.

• 1:16:09Guy Raz?

  I mean, as you kind of think about, you know, with a product you offer and how, you know, technology changes so quickly, what, 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?

• 1:16:28Speaker 01

  I do, and I, I spend a lot of my time thinking about that. You know, 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, right? So, you know, 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, you know, 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, very busy for five years.

• 1:17:09Guy Raz?

  Would you ever sell a company to, you know, a sales force or a huge player like that?

• 1:17:14Speaker 01

  Absolutely not. I'm, I'm very excited about what we're doing. And 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 remotely in my radar.

• 1:17:28Guy Raz?

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

• 1:17:53Speaker 01

  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, same thing for you. The fact that that didn't happen to you, that's luck. And, you know, I look at the 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, when that's grown like crazy. So all those things are definitely luck. But I think, so 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.

• 1:18:38Speaker 01

  It's an appetite for risks taken. So that's my view. I think it's a combination of both. But I think when you add those four things, it just ticks like a whole different level.

• 1:18:52Guy Raz?

  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.

• 1:19:13Guy Raz?

  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 Ramtin Arablouei. It was edited by Neva Grant with research help from Daryth Gales. Our production staff also includes Casey Herman, Kerry Thompson, John Isabella, Alex Chung, Chris Messini, Carla Estevez, Sam Paulson, Malia Agudelo, and Catherine Seifer. I'm Guy Raz, and you've been listening to How I Built This.