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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 it's a really hard thing to do. And from that, calendar 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 Oatana'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.
How much was it going to cost you to get this prototype built? A little over $200,000 is what we thought it would cost. Wow. So I had to empty every single dollar in my 401k. Use every single dollar in my savings account. I had to borrow a little bit in 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.
Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built. I'm Guy Ross, and on the show today, how Tope Oatana 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 phase them. But for most people, rejection is hard. And overcoming the fear of it, building the resilience it takes to withstand the endless knows.
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.
Same thing with entrepreneurs like Davis Smith, who built Codopaxi, and David Nealeman 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 Oatana.
Tope also spent his early years as a salesman, first door to door selling alarm systems, and later doing million dollar software deals with major companies. And all of the knows he heard along the way?
Serve 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 in 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, in a much better sense of the steps he needed to take in order to succeed. And what Tope wound up building was, calendar, 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 calendar, a little about Tope's earliest years. He's Nigerian and he spent his childhood in Africa growing up in the suburbs of Legos.
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. Yeah, so living in a number of different places, but where I lived for 12 years, you'll call it like a lower upper class neighborhood for, you know, in that part of the world. All of our neighbors were friends with all the kids in the neighborhood. My parents were, you know, very active in the neighborhood.
So everyone kind of knew them and they, they were people who were really kind of very magnetic. And so they just really attracted a lot of people, very generous people, very given people and people just, there were always people around. This is what I remember as a kid where you a well behaved kid, depends on who you ask. I knew how to get into enough trouble to really terrorize my siblings, but not really faced a wrath of my parents. Were your parents strict?
My mom was, my dad was not so much. They could not have been more opposite. Your mom was the kind of disciplinarian. Your dad was more kind of chilled out. Yes. So my dad was, hey, you know, let's eat 10 ice cream sandwiches for dinner. That's what we want. And my mom's like, no ice cream in this house. Was, were you a pretty good student as a, as a little kid? I'd say so. Very good, I'd say. Was that something that your parents stressed at home, education?
They did, but not, you know, I don't remember having a lot of conversations with my parents about my grades. There was just an expectation that you performed well in school because they did. I remember as a kid, you know, probably eight or seven. My mom would argue with my dad about how she really thought it was important for us to go to Harvard. And I didn't know what Harvard was, but I know that my mom thought it was important.
And when you were little, like eight, nine, 10, 11, when people talk about you as a smart kid or they say, oh, there's Topey's really smart. Or did you just feel like just everyone you knew was pretty good at school? 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 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. I guess when you were 12 years old, your father was tragically killed. And 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? I remember that it changed everything I thought I knew. So as a kid, my dad was my hero. And because when you're 12, then your dad lets you get away with everything. He's your favorite parent.
Yeah. I would stay up late at night until my dad came home no matter how late that was. So after he died, I went through, you know, it appeared at a 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. You were 12 years old when your father died. And you were there. You saw his death.
I did. It was a robbery, essentially. A car checker. 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. 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, or essentially, think of themselves as your family. 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...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. Your dad at the time of his death had...he kind of had gone through starting several businesses. Some of them were kind of...did okay. But I guess he never kind of fulfilled his dreams really making it big, right?
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 gifted in so many different ways. And I think he felt like he hadn't done his best work yet.
So from what I understand when you finish high school in Legos, you had an opportunity...an opportunity came to you to go study in the United States. Is that what happened? 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 96. You had family already in the U.S.?
Correct. So my older siblings were here, till 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. Where did you move to? Marietta, Georgia. And what was the plan that you would go to university? I mean, you'd finished high school, so what was that the plan? So that was the plan, so I took the 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 two years. And I'm curious, what was it like for you? You would come from Legos to Marietta, Georgia. And now you're a student there. Was it totally different? Was it a completely different world for you? 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, Nigeria, I was a very popular kid. That was very different here. Just a 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 maybe one to elementary school together. And that was, I guess it was tougher socially than academically for sure.
Yeah, do you remember? I mean, coming from Legos 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 jarring or something that you didn't expect when you arrived? 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 and everything I've ever done. So even in high school in Nigeria, I was two 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.
All right, so here you are and you graduate high school. So presumably at this point, you're going to be able to college. You had the opportunity to go in your 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? Correct. And what did you study when you got there? What was your focus? Computer science initially. But I graduated with a degree in business. And why computer science?
Yes, so I picked computer science for two reasons. So back in 1995, Windows 95 was launched. And that really opened my eyes. I just saw all these grown adults tripping over themselves by software. I thought that was really fascinating. I also noticed at the time that their 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. So when you got to the University of Georgia, I mean, this is like 98, I guess.
98. I'm still early days of the internet. Did you like it? Did you like living in Athens? Did you like being a student at UGA? I loved it. I loved it. I felt like I actually came into my own and I was, you know, developing my own independence. And how were you? Did you work? Why are you a student as well? I did. So I initially worked at CVS. Like as a cashier? 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. So you thought that's what I want to do to make more money? Yeah. So I got a job selling alarm systems door to door. Wow. This is why you were a student like during the summertime? 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 dinner time.
And so I'm pretty sure half the people who bought from a bought from this just so they could get back to their dinner. And were you doing this in in Athens, Georgia? Correct. So in Athens, Georgia, so we would go knock on doors for 34 hours and try to make a sale. And what would happen was the job was strictly commission, right? So which is, you know, you could potentially work all week, all month. And make nothing. Yeah, that's right. How did you do? Did you make decent cash that summer?
I did. I did. So what happened was I 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. Yeah, that's great money. 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 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. Did you like going door to door selling things that's really hard? I mean, because people slam doors in your face and they're not interested and they say, no, soliciting. Did you like that?
I liked it. Huh. And I'll tell you why I liked it because of those first two days. Because you made the money. Yeah. And I think it ultimately gave me the understanding that there's a hit rate, right? So if you knock on next 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 wanted to buy that didn't really phase 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. The next day, the next week. So did being a salesperson just come naturally to you? Do you think? I guess you could say so.
I did feel like it was stretching me in new ways that I had never been stretched before. So keep in mind at the time, I'm still a computer science major. Right? So I was used to a different form of any electoral stimulation. I'm coding, you write coding, 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.
And you could, you were influencing people's decisions, right? That was fulfilling in a way. So you graduated from college and when you did, did you have like a ton of job offers? No, far from it. I think one of the things I've learned in myself, you know, many, many years after it, 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. And 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 then my mom didn't know that herself. Not to put the blame on her, but I think there's, I'm probably more savvy about how those things work today.
But from what I read about you, I mean, you did land a couple of pretty good sales jobs out of college. I think for a couple of years you were working for like a luxury travel agency and then, and then you got a job with IBM selling software. What, what was that like? You know, it took me a while to, you know, there was a little bit of an adjustment, right? I 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, to CIOs. So I got exposed to a much more complicated and much more sophisticated sales process. But I loved it. I found myself not really, like I, I enjoy the work I did. But, you know, I've always been a very, very impatient person. 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 accelerator path.
And so I started looking for a much smaller software company that was growing and 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 were probably growing double digits every month. And so I really wanted to work for a smaller company with, you know, more growth opportunity. So you really even, what, where did you find? I went to Kansas City to work for a company called Perceptive Software.
It made enterprise content management software. So I think of it as software to manage paper files, right? So digitalist files and manage approval workflows around it. So this is like B2B stuff, right? 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 meet with the founders. And, you know, they tell the story, the company's found in story. And that story just really opened up my eyes. Why?
You know, it was the first time I heard about the founding story of 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 accepted. 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. And the reason that that business became successful was I 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, 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, 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. And so from that point on, I started dabbling in a bunch of small businesses.
When we come back in just a moment, how to decide to get into e-commerce and how that leads him to failure after failure. Stay with us. I'm Guy Ross and you're listening to how I built this. Welcome to Duncan. With Amax Gold, you can get up to $84 back annually at Duncan locations so you're morning picking me up. Can I have a medium iced coffee with one taste even better? That's the powerful backing of American Express and Roman Required terms apply.
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Get $1,000 off Vanta when you go to Vanta.com slash built. That's Vanta.com slash built for $1,000 off. Hey, welcome back to How I Built This. I'm Guy Razz. 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. 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 the complicated case of malaria.
And so because she was recovering from that, I think of 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 out. And so that kind of accelerated the decision to come back to Atlanta. Was it also a software company?
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 a different industry. So this company that you joined, I think it's called Verde4, is that right? That's correct. And I guess why you were there, you meet like this business contact to, I don't know the whole story, but he 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 an interest in 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 because it turns out that there's a lot of traffic for light bulbs and no one's really satisfying that need very well. I'm just throwing that as an idea. Okay, I got you again. And so I thought that was fascinated and he showed me some of the businesses that he'd help start.
And, you know, 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 they were searching for. Exactly. And are not and no one's really fulfilling the e-commerce need. And what did he come up with? He came back with projectors. Projectors. Projectors, yep. Like slide projectors. Yes. Video projectors.
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 a turn 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.
And you could, with three, six months of work, you could be at the highest rank in site for that keyword. So did you start a projector company? I did. I never used a projector in my life. Right. Well, maybe seen a few in a different meetings. I've never really bought one before. I said 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 have I've had the, we didn't actually go out and buy projectors and sell them on the website. We established dropship and relationships with different wholesalers. And in this space of, you know, two to three months or so, we launched the business. And did you have to put in a lot of money to start this up? 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. That's not a lot of money, but you were just saving all the money that you were making from sales over the years? I was. So I had some really good deers. And I just socked that money away. And did you, like when you told your friends about it, or did you, did you tell anybody about it? Or do you keep it secret? I did, and they all laughed. They laughed. They laughed saying, what?
You selling movie projectors or HD projectors? Yeah, they asked me all the, all the smart questions that you'd 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. 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. All right. So you launch this thing and do any orders come in? They do. They do.
But then I saw very, very quickly that the margins were razor, razor, thin. So you end up selling a $500 projector, maybe you make $5. Why are they so thin? Well, one because electronics in general, it's just very commoditized. And there are many, many other merchants out there. So most of the competitors were actually not making their money on the projectors. 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.
So the light bulbs, maybe the lens, I don't, I forget 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. So how long did the business last? I would say less than six months. Ooh. Yeah. So you lost all that, that $20,000 investment. I did. I did. But I wasn't, it didn't face me. I mean, it was disappointing in some ways.
Yeah. Because I had, you know, because you put a lot of time and effort into getting it up and running, you sacrifice many late nights, many weekends in, and you do all that, and it doesn't really materialize. How did you know it was time to just give it up? Two things, one I realized that I didn't, I just didn't really care about projectors. Right. So what I, 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. 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? No, I knew exactly what I wanted to do next. Wow. What was it? So I wanted to go back to e-commerce, 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. You built a website, and what was the product? So I called the website YardSteels.com. Yard Steels, like, Steels, like cheap deals for the Yard. Exactly. 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, I, I, I, I, 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. Sure, the grill, yeah, the grill. Yeah. So ceramic grill, and people are fanatic about it. People who love it just love it and they're 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 a 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, um, crills. I thought I could be able to 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 yardsteels.com. And eventually I would go start my own, I would build my own, you know, Tobs Blue Egg, whatever you would call it. And did you sink another 20 grand into this idea? Probably a little less, but I forget the exact amount. All right, so you put this up and do orders start to come in? Or to start coming in. And the margins are better this time.
So instead of making, you know, like $5 for $500 purchase, you're making a few hundred dollars on a, on a $700 purchase or something like that. So much better margins. But you never saw a big remake. You would just get the order, you would contact the, the shipper, and then they would ship out of some warehouse. Exactly. Yeah, I never saw one. It's just, you know, order in and order out. And so I think what I found was I did much better than the first business. Right.
So, you know, probably netted 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 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. So when, I mean, so how long did that last? Ultimately that business. Probably about the same three to six months I would say. Right. Once you, I mean, you essentially had two back-to-back failures. Not, this is a good thing because you can need those in the future. You're going to 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? Yeah, so this entire time I never quit my day job. So what I end up doing is 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. 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 idea, I thought that I needed to pick a problem that truly existed. And I needed to pick something that I was, you know, 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, until I found that idea that checked all those boxes.
All right, so you are doing your day job, selling enterprise software. And I guess one day, I'm from what I understand. You like start to think about scheduling and calendars. Tell me what happens. Yeah, so that 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 the kind of companies you're selling to are like the Coca-Cola's 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. Very often you are trying to arrange meetings with 20 people across three different companies.
And it can be very painful. It's so painful when you've got like five people who want to see a conference call and there's multiple emails. And I can do Wednesday. Yeah, but I'm going to Wednesday. I can't do Wednesday. How about Tuesday? It drives me up the wall. 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 going to do an internet search and see what I can come up with.
I 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. And you didn't know what that looked like. You were just looking for an option.
Correct. I just knew that as a consumer, as a potential consumer, I didn't feel like any of the products on the market at the time really checked all the boxes of what I would need. What was it that you thought you needed? Yeah, so a 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. They do a lot of appointments.
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 sales person, 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?
So I thought a lot of the products that existed in 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 game 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 noticed. So you think maybe there's something to this. 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're selling it, how they're pitching it. And what I learned was that it's part of the fact that I thought there were gaps in what they did.
Their customers left 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 I thought if you took it to a whole different level and you really lower the barrier of entry and really democratize it and make 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. And how long? 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 look 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 fact 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 six months, I couldn't sleep. It's all I thought about. It's all you thought about.
When we come back in just a moment, white hope 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 Ross and you're listening to how I built this. As a B2B marketer, you know how noisy the ad space can be. If your message isn't targeted to the right audience, it just disappears into the noise.
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But if it doesn't work with their existing tech stack, they may miss out on its true potential. When your AI works wherever you need it, you can take your business wherever it needs to go. Learn how Watson X can help you scale AI anywhere at IBM.com slash Watson X. Hey, welcome back to how I built this. I'm Guy Razz. So it's around early 2013 and Tope, Oatana has this idea to make software to help people's schedule meetings in the most seamless and efficient way possible.
And the first thing he needs is for someone to do the coding. And so I decide that this needs to happen fast. So it's not really something I can code myself. And so I started going to meetups to see if I can meet other technical co-founders, but that improved to be successful. And so my third option became, let me see if I can hire firm to build this or product. You could not find a technical co-founder. You looked around.
So what happens is that a lot of people have, you know, everyone has an idea for an app they want to build. And so if you're 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 risks, they're going to like better themselves and kind of go after it.
But 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. 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 sort of be like, well, why should I do this with you? Exactly. And also, you know, they're also probably well paid at what they do. So, you know, kind of, you know, risking all that to start up a business with some random person. Exactly. So you could not find a technical co-founder, which is a common problem.
Yeah. So to make this thing, you decided to like outsource it to like some, you know, engineering company that does these things for hire. Exactly. So there are lots of companies out there that really help whether they're large corporations or entrepreneurs bring their products in 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 all they really cared about was. How much you're going to pay us? Exactly. Yeah. 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 on 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 it's a great opportunity too. As a matter of fact, here are three ideas that we have. And so I knew that I wanted to pay attention to them. This company is called Railsware, I think, right? That's correct.
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? No, I didn't, I did not make them sign any kind of a NDAs. Not because I didn't, you know, ultimately what I believe was, and it's still what I believe today is, I think the key to success is the execution of it, not so much this idea.
Because, you know, a number of other people will form it. I had the idea. But I was thinking of executing it in 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 of what needed to be done would be good enough to protect the idea. I mean, that this, 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 or dozen.
And 10, 20, 30, a 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. Absolutely. And, you know, it's interesting you said that because the other thing that happened is I said scrap you entrepreneur one of the things I tried to propose was, hey, why didn'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.
Yeah, because otherwise they'd never get paid. I mean, everyone is going to be calling them up with every idea. That's correct. And so they weren't willing to do it, in which I fully understand and what 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, maybe it's too much to do. But I ended up changing my mind. Why? A few things happened around the same time I found that my mom's cancer was terminal.
And I think it gave me a sense of carpet DM a little bit and just really realizing that, you know, who knows how much time we all have. You know, like, here's my mom and, you know, she's dying. What she make the same decision, if she was fixed with the same decision, knowing her lifespan, how would what decision would she make? Had really changed my thinking around, go for it. You're thinking who knows what's going to happen to me tomorrow? Better do this. Correct.
Now, as 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 it with what you can do and expand from there. All right. So you decided to do this. And how much was it going to cost you to get this prototype built? A little over $200,000 is what we thought it would cost. Wow. Did you have that money?
I had most of it, but it required doing a lot of things to tell you not to do. So I had to empty every single dollar in my 401k. And pay the penalty, presumably. 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 a lending club. At a high interest rate. 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 knee. I mean, that's a really big risk. I mean, you know, you were at 31, 32, I guess. So it 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. Yes. Aren't you nervous? Not at all. It sounds crazy to say that now. 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. 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. 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, 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. So this is 2013. You put all your money into this product to be built. For this company, Railsware, most of them when he's going to them. What did you tell them? You said, okay, I want this to be like a calendar that somebody can just say,
hey, here's a link to my calendar. You pick a time when you want to meet me and that calendar would be integrated with whatever they used, whether it was Google or Microsoft or whatever. Yeah, so a few things. So before I ever met Railsware, I'd actually come up with my own requirements document. Okay. So which, again, something I didn't do with the previous businesses.
So I had, I 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. So what were your requirements? Oh, man, you need to be able to integrate your calendar, be able to specify your availability in all these different ways. 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.
I could just need to be appealing functionally and also aesthetically. We had to get really fancy with how we detected time zones to make it really, 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. All right. So you get this product, it takes about six or seven months.
A meantime, how is your mom doing? This is 2013. Yeah. So she died about two months into the incident about me. So she died in June 2013. Did your mom know much about what you were working on? Not really. So I kind of downplayed it to her. So I told her that I was, you know, she knew about the, she knew about the previous businesses and she supported my, my different business ideas.
But she wanted me to, she wanted me to prioritize my, my day job. 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 done to her, but I really committed a few hundred thousand dollars to it. You never told her. I did not.
Because she wanted you to have security and health insurance and all that stuff, right? Correct. All the things that she felt like, you know, she wanted for her son and she wishes that, you know, that my dad always provided, right? Yeah. So after her death, I mean, how were you able to 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?
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, Calum became a huge distraction for me. And I just, I worked like a dog, just so I didn't have to think about that.
So by the fall, around September of 2013, the first version of this product is available, but you would spend 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 the word out about it. I mean, because you had no money left, right?
Yeah. So, I got, I know, help along the way through a reals were actually. So a few things happened. As reals were was built in the product, they got connected to another potential client, a software company in San Francisco that's gone on and done really well to multi 100 million dollar business now. And that company was looking to engage them to do some work for them. And so, reals were was, was like, hey, let's show you this product that we're built in, right? So they show them, countily.
And at the time, countily 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. And so, somebody from there, from their customer success team, signs up for the product and starts using it to schedule.
So, onboarding calls with their customers, which those customers happen to be K through 12 schools. So, customer success person from this company in San Francisco starts scheduling onboarding calls with the, the K through 12 schools. Yeah. So, the cats out of the bag at that point, because when you send somebody your calendar link and they see it, they're like, hey, what's this? I, I want this too.
Exactly. They say, I scheduled a lot of meetings. That was easy. I would love to use this to simplify my meetings. And so, the K through 12 school start adopted 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 school start doing parent teacher conferences with it. And then, you know, a few weeks in, as 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 struggled with. Wow. You know, how, you know, the administrative burden of setting them up, the participation rates. We want to roll this out to all of our teachers.
And what school wears a school 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. Just to interrupt. What was your business model? How would you make money out of this at that point? Yeah. So, I'm glad you raised that because I think like they dimension that. So, because I ran out of money.
Now, my idea, 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 this 14 days, you would have to upgrade with the credit card. Well, and then pay like a subscription fee. Exactly. But because I ran out of money, we couldn't build the billing features. And so, by default, the product became 100% free. You couldn't build the billing features?
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. You couldn't just like set up quite, as you can't really set up QuickBooks, right? Well, you can set up QuickBooks, but it's within an online product. You have to find a way to restrict the features that they're not paying.
Yeah. You know, there's some technical complexity there. Some work that needs to be done to, to kind of turn the features off and on based on their trial status, their payment status, collecting the payments. Initially, I mean, just to give you an idea. Initially, that was maybe two, three months of work for two engineers to work on that. Well, okay. So, you could not do this. 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, and was the plan to just get a bunch of users and then kind of figure it out? Hopefully, you would get investors. Yes. So, that has to become the idea. So, I was faced with a dilemma. So, keeping mine. I'm still working my full-time job this whole time. Your day job?
Yeah. So, I hadn't left that. So, this is my side hustle. I was still, you know, I was meeting my obligation to the company. I actually had a really good year that year. And so, I felt like so long as I was, you know, it was not interfering with my job. I didn't really, I didn't feel like I needed to disclose it. And so, I have a dilemma in which the business is growing, you know, in the sense that people will sign it up for it.
And every time, 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, I didn't have the money to turn it into a revenue-generating business. And just to clarify, it really started with this one software company in San Francisco and then went to teachers. And then from there, it just organically grew. Exactly. So, the first, you know, 300 or 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. I just began to spread like a wildfire. When did you know, or when did you feel comfortable leaving your job, your day job?
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 I, you know, seeing the growth of, of countly, 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, that choice was very obvious.
And during this time, did you tell anybody about, about your idea or, or did you keep it a secret? Like, did you tell your friends about it? I told my close friends, I definitely told my, my, my brothers and my siblings. Did people think it was a good idea? No, they didn't think so. They thought it was a solid 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?
He felt like he'd filled me that, you know, like, he felt like I was, like, I got, get desperate. I, you know, I'm not pursuing, you know, scheduling. That's a solid 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.
And at that point, you still had not, you were fully, you'd funded this thing by yourself. I funded it myself and ran out of money. And then I convinced Rillsware to work for, not work for free, but to work with understanding that when I raised money, I would pay them back. So, wow. I was able to get them to work on credit. There's a quote of yours I read and I want to read it to you. 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 did a different profile get money through an attempt for shitty ideas. Those VCs were ignorant and shortsighted. The only thing I could attribute it to was that I was black. Can you, can you walk me through your experience trying to raise money? Yeah. So I think, first of all, I think it is difficult for 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 they're raised to play some aspect in it, but it's not really, there's probably more to it than that. But did you, but I mean, you didn't really, it sounds like you didn't really kind of pitch to investors at this point yet.
No, I definitely didn't pitch to investors. Yeah, and I got all in Atlanta, the Atlanta area. All in the southeast. So if you people in Atlanta, if you people in the southeast, I had, you know, a guy from a pretty big firm, not only did he, you know, 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 a.m. to meet with this person. And then he stands me up, right? So just a lot of like a lot of experiences like that, though, just, you know, it's one thing to not invest, but it's another thing to kind of treat people like that.
Yeah, how much is that is just the arrogance of, you know, somebody who thinks they're an important VC versus race. I know, I know 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. How do more of us than I did. So how did you eventually wind up connecting with people who, who did want to invest?
Yeah, so 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 place in Atlanta called the Atlanta Tech Village, which is a, it's a core work in space, specifically for tech startups.
And it's while I'm connected with different investors that the owner of the Atlanta Tech Village catches wind of, calendar 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 is a big problem. And he was impressed with what we done. And so we get connected.
So what happens? So we have a one or two meetings and it falls over the term sheet and says, I love what you're doing. I think that this is, this can be big. I'd left a vest. I read that it's like $350,000 or something like that.
Where do you nervous about taking that investment? Because you won't 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. And 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 seed some of the ownership. But once I met David, that changed.
In the sense that I felt like I was going to have a, when I was going to be, you know, working with a successful entrepreneur himself and not just 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 met him.
So it's, it's a 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 that time? I mean, was that, because I mean, I'm assuming the business even in April was, like, was just you, right. That's right. So it was just me. I was the only employee and then, you know, Railsware. And so that ended up giving me. I wanted to say something like nine months of runway.
I 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. Maybe about 15,000 at the time. 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. Yes. And so that became, you know, priority number one was I raised the $350,000. Because honestly, I, I didn't enjoy the fund raising experience. And, you know, it's not.
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 turned on billing and introduced a premium plan. And so we start generating revenue in August of 2014. And how did the premium plan work? Yeah. So that actually created a, it created some fiction at the time. And, you know, looking back on your work, I've done it differently. But part of friction with customers.
Yeah, existing users. And so some portion of the existing user base was disappointed that they had now had a pay for a product that was 100% free. Right. 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 used to maybe get for free before. Right. And what was, what were you charging for it?
$10 monthly. If you pay, if you paid monthly or $96, if you paid annually. 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 use your, your service. It absolutely was 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 those big, big businesses using our product.
And do you, I mean, do you, at this point, do you just kind of do you continue to seek out outside investors or do you decide to just see if you can make a go at it, you know, through cash flow revenue. 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 is an insurance policy of sorts. We ended up not needing it.
Wow. But we did. Were you ever worried that some big company like, you know, like Microsoft or Google or somebody else would just come in and with a lot more money, you know, and just got to crush you. I used to. What I found is that, you know, when you spend a lot of time with your customers, I think you, you find that there's a lot of things that they wanted to do. That need to be done that maybe those companies don't have the appetite for doing.
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 calendar might be to make sure that it doesn't become obsolete. I do. And I spent a lot of my time thinking about that, you know, our overall vision is to take the workout 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 a meeting is difficult to schedule people sometimes forget to show up when the show up. They're not prepared. There's no clear memorabilization 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. Would you ever sell a company to, you know, a sales force or a huge player like that? 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, there's a lot to do. And so that's not the remotely in my radar. When you think about your journey and what you've accomplished, you know, we've had some incredible lows in your life.
And 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? 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 in the 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 ceiling and life and your, and your floor as well, like how high both, how high or low, whether 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 are 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 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 takes luck to a whole different level.
That's Tope O'otana, 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 evaluation 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 apps so you never miss a new episode of the show. And of course, it's free.
This episode was produced by Rachel Falkner with Music Composed by Rhyme Teen Arablewy. It was edited by Niva Grant with research help from Derrath Gales. Our production staff also includes Casey Herman, Carrie Thompson, John Isabella, Alex Chung, Chris Bacini, Carla Estevez, Sam Paulson, Malia Aguadello, and Catherine Cipher. I'm Guy Ross, and you've been listening to How I Built This.
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