Tope Awotona - Calendly

Calendly’s Founder: Building a $30M SaaS After 3 Failed Startups – with Tope Awotona [213]

Calendly's Founder: Building a $30M SaaS After 3 Failed Startups

Tope Awotona is the founder and CEO of Calendly, a simple and beautiful scheduling tool that helps you schedule meetings without all the back and forth emails.

Tope grew up in Nigeria and moved to the US when he was a teenager. After graduating from the University of Georgia, he landed a job at IBM as a sales rep.

He spent the next seven years working in sales, but deep down he always wanted to become a successful entrepreneur. So he spent his evenings and weekends trying to build a business.

First, he decided to build a dating site after reading an article about But he quickly realized he didn't have the resources or skills, so he never launched the business.

His second startup was an e-commerce site selling projectors. But he didn't sell many and the margins were terrible. He also had no interest in projectors.

His third startup was another e-commerce site selling grills. But he found himself dealing with the same problems. And he just had no passion for that business either.

Tope realized that he was just focused on ways to make money. He told himself that he wasn't going to succeed unless he focused on a problem that he was passionate about solving.

It took another year before he found that problem. He'd spent a day wasting a lot of time going back and forth over email to schedule meetings. So he started searching for a scheduling tool.

But all the products he found were slow and clunky. After months of research, he decided to go all in with this idea. He put every single dollar he had made into this new business.

This time, his bet paid off. Today, Tope's company does around $30 million in annual revenue.

In this interview you're going to learn how he took that idea, overcame the challenges of 3 failed startups and successfully grew a SaaS business that has over 4 million users.

I hope you enjoy it.


Click to view transcript

Omer Khan 0:15
Welcome to another episode of this SaaS podcast. I'm your host Omer Khan and this is a show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business. In this episode, I talked to Tope Awotona, the founder and CEO of Calendly, a simple and beautiful scheduling tool that helps you schedule meetings, without all the back and forth emails. Tope grew up in Nigeria and moved to the US when he was a teenager. After graduating from the University of Georgia, he landed a job at IBM as a sales rep. And he spent the next seven years with me in sales, but deep down, he always wanted to become a successful entrepreneur. So he spent his weekends evenings trying to build that business. First, he decided to build a dating site after reading an article about the founder of But he quickly realized he didn't have the resources or skills. So he never launched that business. His second business was an ecommerce site selling projectors. But he didn't sell many and the margins were terrible. He also had no interest in projectors. And his third startup was another ecommerce site selling grills this time, but he found himself dealing with the same problems. He just had no passion for that business either. And took realized that he was just focused on ways to make money. He told himself that he wasn't going to succeed unless he focused on a problem that he was passionate about solving. And it took another year before he found that problem. It's spent a day wasting a lot of time going back and forth over email to schedule meetings. So he started searching for a scheduling tool. But all the products he found was slow, and clunky. And after months of research, he decided to go all in with his idea. He believed he could build a better product, and he put every single dollar he hadn't made so far into his new business. And this time, his bet paid off. Today Tope's company does around $13 million in annual recurring revenue. In this interview, you're going to learn how he took that idea overcame the challenges of three failed startups, and successfully grew a SaaS business that has over 4 million users. Hope you enjoy it. Real quick before we get started. Firstly, have you grabbed a free copy of the SaaS toolkit? If you haven't, then you can get it by going to The tool kit will tell you about the 21 essential tools that every SaaS business needs. Secondly, enrolled for SaaS Club Plus is now open. Plus is our online membership and community for new and early-stage SaaS founders. So if you need help launching and growing your SaaS business, and you want to connect with other founders around the world, and you want to build recurring revenue faster than plus will help you do that. Just go to to learn more. Okay, let's get to the interview. Tope, welcome to the show.

Tope Awotona 3:25
Thanks for having me.

Omer Khan 3:27
So do you have a favorite quote something that you can tell us that something that inspires and motivates you or just gets you out of bed?

Tope Awotona 3:33
Absolutely. So when I was a kid, and really for a long part of my life, my mom would say this thing that at the time you start knowing me, but man, I've just come to love it my adult life. And the quote is do things the way they should be done. So they can turn out the way they should turn out. And essentially, what she's saying is that something is do or don't write somebody easy they're worth doing or isn't worth doing. And if you're going to do it, don't take any shortcuts, just do it the way it should be done. And you're bound to see great results. And so that's been very instructive for me.

Omer Khan 4:05
Love it. Love it. Total wisdom there. So for people who aren't familiar with Calendly, I'm not sure there are a lot of people who are not familiar with Calendly, but yeah, just tell us like, you know, what the product does? what problem are you trying to solve for who?

Tope Awotona 4:19
Yeah, absolutely. So Calendly is a scheduling platform, that it makes it very easy to schedule meetings across companies, right. So people who don't use calendar, usually they find themselves trading four to five emails to lock a time down for a meeting. Whereas if you're using Calendly, you set it up, you tell me your availability preferences, you connect with your calendar, so it knows when you're free or when you're not free, and what immediate request comes up, you just share the link with them. And rather than this four to five emails, you can schedule that you need in one interaction. We've been doing this for six years now we launched in 2013. And fast forward to now close to 4 million people use the product on a monthly basis. And they range from individual too small teams to large enterprise customers like Zendesk and Marketo, Zillow, and so many others. That's what the product does. And for the people who use calendar, which they're typically people in customer facing roles, not only does it save them time, even get into meetings, it's actually helping them in the case of salespeople help them sell more, by allowing them to connect with their customers at the height of their interests so that new conversations are dropped customer success, people are using accounting to improve retention of their customers, because what they find is that by being able to schedule meetings with their customers, when they're newly acquired, those customers end up having a really good experience with their product. And they turn out to be customers for life, a lot of cases. So those are the ways in which people are using our product cool. based out of Atlanta, and we have just a little bit shy of 100 employees.

Omer Khan 5:46
Awesome. And you you launched about six years ago, right? That is correct. So before we start talking about, like, you know how you came up with the idea for Calendly. I want to talk about you, kind of your childhood, and sort of the journey you've taken to get to even starting Calendly. So you were born and grew up in Nigeria, right? That's correct. So tell me a little bit about like, what that was like?

Tope Awotona 6:11
Yeah, so I was born in Nigeria in the year 1981. Getting old now. But I was born to, you know, both my parents were scientists, my dad was a microbiologist, and my mom was a pharmacist and my dad ended up you know, he was an entrepreneur from us, at least in the time that I known, he was an entrepreneur, my mom worked for the Central Bank of Nigeria. And so I had really interesting parents, they were, you know, both very ambitious and hardworking themselves, but from a very early age, they inspired me to, to dream big. And also, I saw some of the ups and downs of my dad as an entrepreneur. And I think all those things motivated me to want to be an entrepreneur someday. But I didn't have a timeline or a plan to get there to do exactly that. We moved to the states at when I was 15. And in 1996, and I finished high school here. And then I went to college at the University of Georgia.

Omer Khan 7:03
And you moved to the US because you're a super smart student, right?

Tope Awotona 7:07
Something like I was like, I don't feel so smart these days. But I was. So you're right, though. In middle school, I skipped a couple of grades because I was part of the like the gifted equivalent of the gifted kids program. And my mom always wanted kids to go to college in the States. Because primary and secondary school is great in Nigeria, but the college education is not great. And so my mom wanted me to have that opportunity. And so that's why we we moved here. And for me, I've been here a lot before I moved here. But coming here was a very exciting experience. And it took me a little bit of time to fully assimilate. But once I got here I was I was eager to get going.

Omer Khan 7:47
Yeah. So you, you went to college in Georgia?

Tope Awotona 7:52

Omer Khan 7:53
And then what was your first job?

Tope Awotona 7:55
What my first job was actually in high school before college, and I worked at a fast food place for like two weeks, and then from there went to CBS. But my first job in college was, I worked for a call center. And it just cold calling people requesting donations, which is one of the most difficult things that you can do. After you get the initial shock of people saying no to you, you actually fall in love with you fall in love with being able to persuade people to give you their money. And so I ended up working on my sales jobs in college. So I did the call center. And then after that I worked for att selling alarm systems door to door. Those were some interesting days. And at the time, I didn't know it but like the experience working those jobs completely changed my career.

Omer Khan 8:38
Well, you are kind of pretty resilient person. But that age or if not, I'm sure going through those types of jobs must have made you more resilient.

Tope Awotona 8:48
Yeah. So we when I did a call center job I was I became more resilient over time, I don't know that I started off being incredibly resilient. Part of what happened is this. So when I worked at a team alarm systems door to door, it was the first job I ever had, that was strictly that was all commission, right. So there is no hourly wage or anything to like, either sold and you ate or you start. Luckily for me, though, the first day I started, I did really well. So I ended up making $500 my first day, which is not a lot of money to most people. But as a 17, 18 year old college kid, there was a lot of money to me. And to make that in a day was really exciting to me. And that was my first day was a Monday, the rest of the week, I didn't make any additional money. And so if the order of the of my success would have been reversed. So like if I would have went the first four days without making any money, I don't know that would have come back on the fifth day. But the fact that I saw what success could look like on the first day actually really motivated me to stick with it. And I think it began to give me resilience because I knew you know what the success rate was, I know that I could go up to four or five days, I'm not doing really well. And I just needed one really good day to change all that around. And that's when I became comfortable with betting on my myself, and also taking risk.

Omer Khan 10:02
And then for you sort of landed in a few different jobs, including at IBM, and they were all sales jobs?

Tope Awotona 10:09
Correct. All my professional career up until I started dabbling into entrepreneurship. There were all sales jobs. But there were, there were sales jobs in which I was selling to, you know, I'll sell enterprise software to large company. So on the low end, you're selling, you know, deals that are in, you know, the six figures on the high end, you're doing some deals that are in the seven figures. And so it's a very kind of strategic and I know complex sale.

Omer Khan 10:33
Yeah. Okay, so I want to kind of get on Calendly, but there's kind of an important kind of part that we need to cover, which is you had like three failed startups before you started currently. So can you kind of just quickly run through what those three were? And why what's sort of the takeaway that why you think they didn't work out?

Tope Awotona 10:57
Yeah, so I'll run through it quickly. But I'll also give you a quick story and how I started my first business, the very first business actually. So in around around the 20, it was like the 2009-2010 kind of time frame, I was not crazy happy with the company I was working with at the time, and I wasn't, I wanted to change. And I thought given some of my experiences at some, you know, very successful startups, I thought and also kind of learning the stories of those companies, I felt like I had what it took to start a business. And so I started looking for businesses to buy it at the time, I got connected with this guy who was a broker representing one of the businesses that I want to buy, we can not agree on a price. So this guy is like, Okay, this business you're looking tp buy is more than you're looking to spend. But I can actually help you build a business like this for a lot less than what this person is looking to sell this business for. And that was my very first business. And so this guy told me that there was an opportunity to start an ecommerce business, specifically an ecommerce business selling projectors. So he done some kind of analysis and figured out that if I built an ecommerce website for projectors, I could ring I stood I had the opportunity to rank really highly for some heavily searched terms. And that's how I got into selling projectors.

Omer Khan 12:14
But the reality is, he didn't he didn't sell many though.

Tope Awotona 12:17
I didn't, I didn't. I didn't sell many. But the beauty of the internet is, if you launch something, you put it up there, it takes a lot to not sell anything. Right. And so that was like that was in some ways. Well, it was, you know, the success that I had is not what I was looking for. It was also inspiring in the sense that like, if you do something really well, you put it out there, you'll get people who will, who will find it by and then over time, you can make it better. Ultimately, what doing that business was one, I realized that to make it a really successful business, I one needed to actually care about projectors. And I did not care about projectors, I'd never bought a projector myself, I'd operated a few projectors from you know, price sessions that I gave. But montage, I knew very little about the problem, I didn't know. And I didn't care to learn more about it. So kind of the moral I took away from that is like one L and also by the way, the margins of the product were really thin. So we're talking, you know, just very thin margin with electronics. And so I decided that whatever I did Next, I wanted the margins to be better, I needed to spend more time thinking about, you know, exactly how I would acquire customers in a repeatable and cost effective way. And it was going to be something that I felt like I cared about. Ultimately, I started a second business that was a yet another ecommerce business, this time selling Home and Garden equipment, the margins were better, I put more thought into, you know, customer acquisition. But again, it wasn't really something I was passionate about. And so as I realized that, it to scale the business and make it all in a very successful, I couldn't just be a mercenary, I truly needed to care about the problem, and be motivated to solve it. So that's why I don't want to feel it, too. So

Omer Khan 14:05
it didn't you also start a dating site after reading about what how much money Plenty of Fish was making?

Tope Awotona 14:12
Correct, I didn't actually start that I never launched the actual dating website. But that was the first one that I would say that was the first idea that actually acted off, I bought some domains, I created a holding company for it. And I bought some books on coding, because I hadn't put it into a few years. And I bought this dating software package. And I was going to customize it to make it work for this website. But I just never got around to really do it, cut it, I spent the money to spend some money on the idea, but I never just never followed through.

Omer Khan 14:43
And then at some point you you kind of were like, Okay, I'm kind of trying to build these businesses, and they're not really going anywhere. And you sort of decided that you're going to sort of take a step back, and sort of wait for the right idea to come along.

Tope Awotona 15:01
That's correct.

Omer Khan 15:03
So tell me about like, Calendly, like, how did that idea come about?

Tope Awotona 15:06
Yeah, so after a number of failed ecommerce websites, after, you know, I would say week attempt to start the dating website, I realized I was just burning money left and right. And that was just going to take a little sabbatical from starting businesses. And I decided that my next business was not going to be something in which I was, you know, so that the businesses that I started before that I started them, because I wanted to start a business, the businesses were not started because there was a big unmet need that needed to be served. And so I said that I was going to take my time and not a forcing ideas, I will let the ideas come to me. And this time around, I would make sure that it was something that I was passionate about. It also needed to be something that would be fully committed to and not something that was just doing as a as a side business. Right. Most of the other businesses that I started, there were part time, you know, endeavors. And there were never really things in which I, I envisioned myself quitting my job. And doing full time I thought, whatever. So I take this sabbatical from starting businesses. And yeah, Calendly comes up. And the way it comes up is I'm looking to schedule a meeting. And I forget exactly who I'm trying to schedule a meeting with at the time. But I was trying to maybe coordinate a meeting across maybe three different companies with about 10 to 20 people, I forget exactly how many. And it was just so painful. And so the problem that I had was I was just trying to, you know, corral all those people. And my solution to it was I was just going to sign up, there had to be some commercially available product that could just go sign up for a buy that would solve this. And so I wasn't looking to start a business, I was just looking to buy something, I began to investigate the different options out there. And there was just really nothing on the market that did it. And it got me thinking, but because I had all this phase filled businesses, I was a little gun shy, right. And so I spent many months trying to find reasons not to do it. Right, I looked at all the different products on the market and I these people are closed. Initially, I was telling myself like these people are close, and it's only a matter of time before they solve this problem. You know, this doesn't have to be something I solve. But the more I spent time I you know, initially that was my position. But as I did more research, my mind began to change. I thought that unlike all the other businesses that I started to start, I actually thought I had a unique, I was uniquely qualified to do this. And the reasons were, or this one, as somebody who was in sales on my lap, I spent literally my whole entire professional career scheduling externally, I really understood the problem. One, too, I was a you know, before I went to enterprise software sales, I was a computer science major. And so I felt like I had the and one of the things that really helped in my career is just like a good combination of technical and business acumen. And I felt like I also had that and that would, you know, somebody with that kind of mindset would be, you know, very well positioned to build something here. The other thing I thought I had was having worked at a lot of successful software companies, I actually knew what a success was cover company and look like unlike all the other ecommerce businesses I tried to start I didn't know anything about ecommerce was I knew a lot about software. And I spent, and at that time, about seven years working for enterprise software companies. And I also felt like what was missing from the market at the time was usability. I thought a lot of the scheduling products that existed on the market at the time, we're not we're clunky to us, they're difficult to use. And I thought I had a good eye for usability and design, folks. So for all those reason, I thought I could actually I was well positioned to create something unique and differentiated. And so I empty my bank account to pull the trigger.

Omer Khan 18:34
Yeah, I really liked the fact that you said I spent some months trying to talk myself out of doing the idea. And I've heard this many times before that, in many ways when you come up with an idea, and it's easy to fall in love with it. And it's easy to come up with all the reasons why you should pursue that idea. But many times, if you try to not validate the idea was invalidate it or talk yourself out of it. And you can't do that, then there's probably something that's worth putting your heart and soul into.

Tope Awotona 19:03
Absolutely, absolutely. And I think that's what I did differently this time, is I think you have to go into the idea with, you know, really like, I think most people I know I was in my with some of my earlier ventures. First I started with the idea I was going to solve this problem, I was going to launch this thing. This is regardless of what the research said. Whereas in this case, I was very open minded I was being open to being I was open to being swayed in either direction. But the more I tried to dismiss the idea, I I became obsessed with it, it was obvious that there was a glaring gap in the market.

Omer Khan 19:36
And did you sort of try to validate it by going out and talking to people or, which is based on your own research and your own experience? You felt like okay, I feel kind of good about moving to the next step.

Tope Awotona 19:49
Yeah, so I don't think there's any book that any expert that recommends that approach I took, but I did not talk to one single person. So I didn't know validation. But to me, the idea was like, so I have a unique approach to you know, to validating things. And that is I pay more attention to what people have already done or are doing than what they see. In other words, I care less about interviewing people and asking them, do you want any scheduling tool? Or, you know, would you if I built these features? would you use it, what I pay more attention to is the fact that one there were products on the market, right. And that told me that that's the best validation like people are today, regardless of what I thought of those products. The fact that people were paying for this products, and there were a number of them. And while they were there were relatively small businesses, I saw thought in spite of what I thought was not great execution, the fact that they had built decent businesses, I thought that was a lot of validation. And so what I spent most of my time thinking about was, you know, the fact that people were paying for it, that's all the validation that I needed. I spent most of my time thinking about what would I do differently to again, you know, have a unique and differentiated product. So I spent most of my time doing that, more so than validate the idea.

Omer Khan 21:04
And then you you really went all in and you you kind of put everything you had into this business. And so this was very different to the other startups that you'd worked on. That's correct, right. I mean, there was there was no, it kind of, you know, when you and I were talking about before we started recording, and you were talking about like, okay, I had to make this thing work. It kind of reminded me of this. I can't remember exactly, but it was a Will Smith quote where he talks about, like, why you shouldn't have a plan B. Like, you have to dig that out. But yeah, I mean, it kind of reminded me of anyways of that. So how did you start building the product? Like, did you start coding yourself? Did you spend that money to hire some developers? Like, what did you do?

Tope Awotona 21:47
Yeah, so I hire developers. But before that, what I did was, so I had the idea I looked at, you know, I looked on the market, and I saw the different options. And so this is what I did for validation and discoveries, I spent a lot, I'm using all of those products. Right. And not only reading them, but also reading through their, their idea portals and in their communities and their forums, you see what their users were saying. So a lot of times when people go to create a product, you know, they think there's an idea for they have a product or service that they want to launch. They don't respect their competition enough. And so they think that I can do it better, which I certainly feel the same way. But I, I don't think you can discount the fact that these people have some customers. And so I believe that whether you like your competition or not, there are things that are doing really, really well. And it's important for you to understand what those things are. And so I spent a lot of time trying to understand what did people like about the existing tools on the market. And I also use them myself to really figure out what worked out really well, what did the existing tools figure out so that I could replicate to the things that he did really well. And so I spent six months, that's part of what I did in the six months. And that's what gave me a lot of confidence to go all in on the idea. So because I've done it, I've done a ton of research. And I didn't just kind of do it in a in a way in which I was looking to come from all my own hunches. Because I've done that idea had really strong conviction at that point. And so I raided my bank account, and I still hire engineers out of the engineers I initially hired, were in Ukraine, so I actually had a fly there to meet with these people. And it turned out to be a really good working relationship from the start. And I committed to it.

Omer Khan 23:28
And so you looked at these other products, I think that's smart to spend time, like understanding what your kind of future competitors do well. And in terms of the gaps you talked about, kind of okay, they will kind of be the slow, difficult to use. And so you kind of put a big emphasis on, okay, I'm going to really focus on usability and the user interface and ease of use and those kinds of things was that like, the main thing that kind of drove you in terms of saying, Okay, this is if I get this right, this is how I can differentiate this product and win customers.

Tope Awotona 24:08
So I thought of few things so, some of the things I noticed were one and this goes back to me saying because I scheduled a lot of meetings, I knew what was important to as a salesperson, I thought of meetings a little bit differently in the sense that like, sales, people understand that when you're inviting people to meet with you, it's not granted that they'll meet with you. Right. And so in some ways, I you still have to, you have to convince them to meet with you. And so it's that realization, one of the things I realized, as I look, as I looked at all the different tools on the market was they paid a lot of attention to the experience of the person that was a user of their product, their registered users, user their product, ensuring their availability, they did not pay enough attention to the user experience of the recipient. In other words, if I want to get you to schedule with me, my chances of getting you to follow through on my request are greatly increased it by make the experience really, really easy for you. And that's one of the things currently got right initially, right. So I paid a lot of attention to the existing tools on the market, I looked at how many clicks and how many page refreshes. And the number of steps a user had to go through to book a meeting. And I was maniacally focused on reducing those steps. And some of the things that we did to reduce those steps is we just detected time zones in a much better and cleaner way for the user. So that again, reduce the number of things they needed to do. But that was one of the unique advantages that Calendly had initially is just like the experience for the invitee, the person you're inviting to schedule with you what just a lot better and a lot seamless. And it got more people excited about using people who hadn't used a scheduling tool before, a lot more open to it because of user experience was just really good. So that was one thing that we bet on. The other thing was designed. So the time I wanted as a launch calendar was 2013. At the time, and, you know, this is around the time in which Apple was becoming one of the most valuable companies in the world. And it really got there on the back of it on design in a both from an aesthetic standpoint, and also from a functional standpoint. And so one of the other things that I think only got right was it looked like a mother tool. Again, it was much more inviting and, you know, repeated a lot of invitations to design. So the experience for the invites he design in And the third thing was integrations right. So a lot of the tools on the market didn't really integrate with as many of the of the most important business applications that that users care about. And so I thought that if you if you did all three of those things very well, you have a very differentiated product.

Omer Khan 26:39
How long did it take you to launch the product?

Tope Awotona 26:41
The MVP from it was about six months.

Omer Khan 26:44
Okay, so you get the product launched. And you know, I've seen this a lot. I've seen founders who see an opportunity, they think they can build a better product. They get it launched. And then it's just crickets, right? I mean, just trying to find that first 10 customers, people you don't know, to come and use and sort of pay for your product. So what was that experience like for you?

Tope Awotona 27:11
Yeah, so when we launched the product, it was free. And it was free. You know, because we actually ran out of money, the plan was to make it a paid product. But we didn't get around to build into billing features and doing the billing integration. So as a result of that the product was free, which is turned out to be actually one of the best decisions that I didn't make. So the fact that it was free helped a lot. And then the other thing with the product is that it's viral. So some of the very first users of the product were actually. So if you recall, I said I work with these engineers in Ukraine to get started. It was a dev shop. And they were also working with another company in this in the Bay Area, a company called Bright Bytes, actually. And so that company was a client of theirs. And so there was a conversation between the engineers who we're working on our product. And some of the engineers are working on a Bright Bytes product. Long story short, people from Bright Bytes, find out that these engineers are working on this scheduling product, they're like, Oh, we have a need for that. We'll check it out. The product of the time is not generally available, right. So you can go up to the counter, you could go to and sign up for it. But it wasn't we weren't, you know, I wasn't telling people about it. But long story short, they signed up for the product before we were ready to talk about it publicly. And they were the some of the first users of the product. And it was their customer success people and they were selling to people in the education space. So patient A is the customer or the customer success of Bright Bytes their scheduling with people on in K through 12, those K through 12. People pick it up. And they start using it for parent teacher conferences. So it goes from Customer Success calls to spread virally to some schools, and they begin to use of a parent teacher conferences. And then it just continues to grow that way. So that's how we got our first thousand users. And total today, still, the primary channel through which we grow is the virality of the product. So the combination of the fact that the product is free, so reduces the barriers to entry to get into the product. And when people use the product to introduce other people to it, and then look at the versatility of the product and serve a lot of different needs. All those things combined is essentially how we got to how we were able to grow, as we began to grow, we then started paying attention to their request or coming in and trying to understand why they were coming in and what they were looking to do. And those led us to so you know, those led us to really understand where the segments in which were more successful than others. And then we just began to double down on those.

Omer Khan 29:40
So in many ways, the freemium model for you, for Calendly has has turned out to be one of the best decisions, as you said you didn't make. Yes. And initially it was it was just pure accident, because you didn't have enough money to get sort of the billing piece done. And obviously, the virality is is a huge piece, because you know, really super easy to get somebody to use a free product. And if it's, it's intuitive and easy to use, they're going to start using it. And then every time they're scheduling a meeting, they're effectively promoting the product, as well. At what point did you start charging?

Tope Awotona 30:21
Yeah, so this actually goes to let you wrap this up. And this is actually one of the first mistakes that I made, we launched a product in like late 2013, let's say like September, October, if I would have known how big what I was working on was at the time, I would have paid more attention to it. But did that go. But there's just so much going on. We start charging in August of 2014. So about a year after we launched the MVP, and we made a mistake there. And one of the mistakes that we made was we didn't give it a long enough notice about the about the decision that we would start charging. And then turn hindsight we should have grandfathered some of the early users. But we didn't do that.

Omer Khan 31:01
But they could still keep using the free plan, though. Right?

Tope Awotona 31:03
Correct. But what was included the features, including the free plan change, once we started charging, we package the free plan and remove some functionality from it. And then introduced a paid plan that had some of the features that were previously in the free plan, in addition to as well as some new completely new feature features. And hindsight, well, what I think we should have done was maybe just grandfathered everybody that was in the free plan and let them keep that plan, just as a gesture of, you know, I guess appreciation for using the product in the early days.

Omer Khan 31:36
Yeah. And so kind of what was the impact of of doing that?

Tope Awotona 31:40
Well, the impact of doing this way?

Omer Khan 31:46
Yeah, you said it was a mistake. So like, why did you feel like it was a mistake? Is it just because you feel bad about not grandfather's people? Or did it lead to like a lot of complaints or kind of, you know,

Tope Awotona 31:57
yeah, so that really the silent majority just I was happy that we were generating, and that they were grateful for the time in which they were able to use the product for free. And once you start charging, started charging, they just paid for it. And then they were happy that by having a business model that wouldn't be in business for a long time, because they didn't want to lose the product. But nonetheless, there are some people that were unhappy that we changed the free plan. Now, for every person that complained, the complainers are variable before every one of those complaints, or maybe 20 other people who upgraded and didn't say a word. But nonetheless, I think that, you know, hindsight 20, and in the grand scheme of things like what the revenue we gained from grandfathering, those people is probably was probably not worth some of the chaos I created.

Omer Khan 32:45
Yeah, and I think it's interesting, you said that, you know, if I had known how big this thing was that I was working on, I would have, you know, done things differently here and there. And, like, when you start to look at me, you go, okay, scheduling product, there's a bunch of them out there, how much of an impact can I really have? But, you know, you've you've gone to a point where you mentioned like, you know, 4 million people using this product every month? And like ballpark, like how much revenue are you doing each year?

Tope Awotona 33:21
About 30 million, and growing, you know, 100% year over year.

Omer Khan 33:26
Wow. And to kind of make that even more impressive is like, you literally bootstrapped this business. And even now, like you haven't raised a lot of money, have you? That's correct. So I think this is really good lesson there in terms of like, sometimes, like, we don't think big enough. You know, it's like, you sort of start out and you sort of have this idea. And I'll be like, Oh, I I'd be happy if I got like, you know, thousand customers? Yeah. Look where you can end up?

Tope Awotona 34:00
Yeah. So it's interesting, you say that I actually think it is good not to think too much about how big what you're working on it. Because I think that in and of itself can also, you know, kind of lead to a state of paralysis, right? If you truly know the impact of what you're working on. And I think that pressure also overwhelm some people.

Omer Khan 34:19

Tope Awotona 34:20
So I think there's a happy medium there.

Omer Khan 34:24
Yeah, totally. So, you know, I think it's a really interesting story. You know, like many, many entrepreneurs, you went through kind of the journey of trying to build several startups and kind of failing, until you kind of eventually landed on the right idea for you. And at that point, it seems like, you know, everything sort of clicked into place, right? Even the mistakes that you were making, like not having a billing system in place. So you had to push the product up for free, actually turned out to be a really smart thing, because that it's been so important to the growth of of calland Lee, but I also know that you've talked about it being an emotional kind of roller coaster for you. And, and I think any founder and entrepreneur can relate to this, well, you know, one day you feel like on top of the world, and the next day, you don't want to get out of bed. So you've been there too. And interestingly enough, like you told me, like, like, a lot of those moments were like, after you had launched currently,

Tope Awotona 35:31
yes, and so like, for me, the most difficult part, the ups and downs, we really come as we scale the business. The reason is, I think that in the early days, you don't have much to lose, right? You know, like, you have a lot less to lose, as you have more to lose the impact of the, you know, the weight of every decision is a lot bigger. And you know, you have more customers, right? And so like your ability, you're not working, I'm a clean slate anymore. And your customers have certain expectations, and you know, they all want different things. And you hired people, and you make promises to them, at least they, you know, they left their jobs to come work for you, because they believe that you're doing something really special. And so, for me, I think the the challenging part was I had all these responsibilities, all these different people. And in some ways, I felt like they handcuffed me in the business from, you know, some of the other things that that business you do. So that was really rough. And there were times in which you know, as you're growing, you think, you know, what a role should do and how in a what kind of person you needed in the role, but because you've never hired it before, you know, you do a poor job of filling the role. And then to compound that maybe you hire five of the same people in that role that you're still learning. And two months later, you find out that man, I hired all the wrong skills for this role. How do I fix it with these people? How do I put these people into other jobs that are important for the company and part of the company's growth and that they're still interested in. So kind of juggling all those mistakes around or design around hiring too fast, hiring too slow, not bringing in senior leadership enough? Soon enough, those are some of the mistakes that I made that really crushed me. But over time, I recognize them and I surrounded myself with really good advisors that helped me see it. And I started to build a team out in the right way. Invest in our culture, and values. And all those things have just made a difference to kind of put us back on the right track for for growth and also having a fun and exciting work environment.

Omer Khan 37:32
Yeah, I'm glad you you mentioned that, because we often hear about, you know, I hired the right people or senior people too late. And you know, often we think, hey, if I had the money, I would hire more people faster. Right. And you did that. And it was like we talked about the five people that was like five product managers you hired almost at once, right? So there's a downside to hiring too fast as well. So

Tope Awotona 38:01
Yeah, yeah, absolutely. Especially when you've never heard of that role before. Right. So like, when you're hiring a new role, what I've learned is just to do it slow, maybe hire one or two, so you have a point of comparison. And then once you figure out what success looks like in the role, and what types of people can be successful in the room, what types of skills can be successful in the role? Like truly prove it out? I think then you can hire fast and hire super fast. But never, you know, for me, I don't, I never want to hire super fast. And once I've proven that I know what it takes for those roles to be successful in our business. Yeah.

Omer Khan 38:34
Okay, so we need to wrap up and I want to move on to the lightning round. But before I do that, I found a picture of you with Ashton Kutcher visiting you at the academy offices. So what is the story behind that dude?

Tope Awotona 38:46
So the story behind, finally , you found out I forgot about that myself. So the story is, I was interviewing a product manager, and I'm assuming the interview and in walks Ashton Kutcher, like, it was not a planning meeting. So I guess the background behind the story, which I didn't know at the time was, he was coming to the tech village. He was, you know, at the time, we were the tech village. And he wanted to come meet with the promising startups in the in the building. And, you know, the director of the technologies told him told him to check us out. But all this happened short notice. So I I got no advance notice of it. I think they actually sent me an email, email. But because I was in the interview, I didn't see it. Long story short, I'm in this interview, and human comes Ashton Kutcher. And so I tell my, the guy that I'm interviewing who's still with us who I went, I went on to hire he's still with us today. That this is not you've been punched. This is Ashton Kutcher just randomly showing up in our interview. So yeah, that was a that was interesting. I love it.

Omer Khan 39:43
Alright, cool. So I'm gonna ask you seven quickfire questions. Just try to answer them as quickly as you can. You're ready. Yeah. Okay. What's the best piece of business advice you've ever received?

Tope Awotona 39:55
I mean, I've gotten a lot, but I still go back to my mom's advice. That's my favorite one.

Omer Khan 40:00
What book would you recommend to our audience? And why?

Tope Awotona 40:02
Oh, one of the books that I really like is Outliers by Malcolm Gladwell. What I like about it is just it tells a success story of the success stories of people like, like Steve Jobs and Bill Gates, it just won't surprise just describes, what are the attributes that you know, hyper successful people have at the finery?

Omer Khan 40:22
Cool. So what's one attribute or characteristic in your mind of a successful founder?

Tope Awotona 40:28

Omer Khan 40:30
What's your favorite personal productivity tool or habit, apart from Calendly.

Tope Awotona 40:35
Yeah, well, so Calendly, is number one, obviously. But another tool that I really like is this tool called Monosnap, very obscure product. But what it what it does is it allows you to just do a screenshot and easily share the link and easy share link that can take people to that screenshot that you know you took. So I like it a lot, because a picture's worth 1000 words, if I'm describing something to our product people. And I can just share a screenshot or record a quick video and share it with them.

Omer Khan 40:59
Cool. I'll include a link in the show notes to that I use a product I'll give it give it a shout out never mentioned it before. But I use a product called Cloud App, which does something very similar. And so like literally, like I can just like on my Mac, just take a screenshot, like I was just, you know, whatever the short key is for taking a screenshot, and it automatically uploads the image to the cloud and copies the link. So literally, I could just go into an email and paste and there's a link there that I can share right away. So it sounds like it's pretty similar to that.

Tope Awotona 41:27
Exactly. Same exact name. And I don't know what I've heard from Monosnap. But if they came tomorrow and said, it's now gone up to $30 a month, I would pay maybe I shouldn't say that I'm exactly that. But yes, it's a very simple thing. But it just creates so much. So much joy for me every day.

Omer Khan 41:46
All right, you're focused, you're founder, you're growing super fast, hundred percent a year. But what's in your crazy business idea that you'd love to pursue? If you have the time.

Tope Awotona 41:58
I have a lot of different ideas. And by the way, I'm not going to pursue any of them. Because Calendly keeps me pretty busy. But I think there's an opportunity for a new product in the fitness industry that maybe a combination of some across fitter when I work out. I think it's a combination of CrossFit and let's put it this way, a much more accessible CrossFit less intimidating to the to the general population. But I think the workout itself as a great product, but I think you modify a little bit for the masses. And I think if you did that really well, there's a really good business there. Right.

Omer Khan 42:35
But what's an interesting or fun fact about you that most people don't know?

Tope Awotona 42:38
Yeah, so when I was 17, or 18, I, I filed a provisional patent for an invention that I had for cash registers to retrofit cash registers to automatically count cash. I never did follow through on it, but it was a pretty good idea, I think.

Omer Khan 43:01
Did you get the patent?

Tope Awotona 43:02
on the show, there's no approval process for a provisional patent. It's just really provisional. Okay, yeah, it's a way for you to bookmark the idea, but I didn't follow the actual patent, but yeah.

Omer Khan 43:13
Finally, what's one of your most important passions outside of your work?

Tope Awotona 43:17
You know, I'm a very curious person. So I like traveling, you know, to chance to help me satisfy my curiosity. And other issue that I'm passionate about is just improving diversity and inclusion in the tech space. That's not something that I've spent enough time. I haven't acted as much as I'd like to help that, but it's a topic that I'm passionate about.

Omer Khan 43:37
Cool. All right. So if people want to find out more about Calendly, go to And if people want to get in touch with you Tope, what's the best way for them to do that?

Tope Awotona 43:46

Omer Khan 43:47
Okay, cool. So I'll include a link to your LinkedIn profile in the show notes just to make it easy for people there. Great. Thanks, man. It's been a pleasure. I really enjoyed this conversation.

Tope Awotona 43:56
I did as well. Thank you so much for having me.

Omer Khan 43:58
Yeah. And as you know, as I mentioned that I'm a I'm a Calendly customer, a big fan. I love what you guys are doing. And I'm excited to see how the product keeps evolving.

Tope Awotona 44:08
Thank you very much. We'll keep it that4 cranking for you.

Omer Khan 44:11
For sure that Yeah, make sure everyone's busy.

Omer Khan 44:15
Just took all the best. Thanks for listening. I really hope you enjoyed the interview, you can get to the show notes as usual by going to, where you'll find a summary of this episode and a link to all the resources we discussed. If you enjoyed this episode, then head over to iTunes and subscribe to the podcast. And if you're in a good mood, consider leaving a rating and review to show your support. Today I want to give a shout out to John Bai that's J-O-N-B-A-I who left the following iTunes review.

Omer Khan 44:46
“Plenty of insights on running a SaaS company owners podcast is incredibly helpful and full of actionable takeaways that you can use in your own software as a service business. If you go through the entire series, you'll find many nuggets of gold with hundreds of entrepreneurs having shared their advice and experience of success and failure.”

Omer Khan 45:07
Thank you, John. I really appreciate you taking the time to write that review. And it always pumps me up when I hear how the podcast is helping SaaS founders like you so thanks again. Alright, so thanks for listening. Until next time, take care.

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