Omer (00:16.000)
Welcome to another episode of the 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 Awatana, 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 he landed a job at IBM as a sales rep and he spent the next seven years working in sales.
But deep down, he always wanted to become a successful entrepreneur.
So he spent his weekends and evenings trying to build that business.
First, he decided to build a dating site after reading an article about the founder of plenty of fish.com but he quickly realized he didn't have the resources or skills, so he never launched that business.
His second business 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 and his third startup was another e commerce site selling grills this time.
But he found himself dealing with the same problems.
He just had no passion for that business either.
And 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.
And 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 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 had made so far into into his new business.
And this time, his bet paid off.
Today, Tope's company does around $30 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.
Tope, welcome to the show.
Tope Awotona (02:46.320)
Thanks for having me.
Omer (02:48.320)
So do you have a favorite quote, something that you can tell us that's something that inspires or motivates you or just gets you out of bed?
Tope Awotona (02:54.800)
Absolutely.
So when I was a kid and really for a long part of my life, my mom would say this then that at the time used to annoy me.
But man, I've just come to love it in 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.
Right?
Something is either 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 (03:26.260)
Love it, love it.
A lot of 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 just tell us like, you know, what the product does, what problem are you trying to solve for who?
Tope Awotona (03:40.500)
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 Calendly are 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 Calendly your availability preferences, you connect to your calendar so it knows when you're free and what you're not free.
And when a meeting request comes up, you just share the link with them.
And rather than those four to five emails, you can schedule that meeting 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 individuals to 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 in getting the 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 interest so that new conversations are dropped.
Customer success.
People are using Calendly 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 in a lot of cases.
So those are the ways in which people are using our product.
Omer (05:02.400)
Cool.
Tope Awotona (05:02.960)
Yeah.
We're based out of Atlanta and We have just a little bit shy of 100 employees.
Omer (05:07.760)
Awesome.
And you launched about six years ago, right?
Tope Awotona (05:11.700)
That is correct.
Omer (05:13.140)
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?
Tope Awotona (05:29.060)
That's correct.
Omer (05:30.340)
So tell me a little bit about like, what that was like.
Tope Awotona (05:32.980)
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.
For most, at least in the time that I know him, 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 dream big.
And also I saw some of the ups and downs of my dad as an entrepreneur.
And I think all of those things motivated me to want to be an entrepreneur entrepreneur someday.
But I didn't have a timeline or a plan to get there to do exactly that.
We moved to the States when I was 15 in 1996, and I finished high school here and then I went to college at the University of Georgia.
Omer (06:24.850)
And you moved to the US because you're a super smart student, right?
Tope Awotona (06:28.770)
Something like I was.
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, the equivalent of the gifted kids program.
And my mom always wanted her 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 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 (07:08.410)
Yeah.
So you, you went to college in Georgia?
Tope Awotona (07:13.850)
Correct.
Omer (07:14.330)
And then what was your first job?
Tope Awotona (07:16.650)
Well, 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 I went to cvs.
But my first job in college was I worked for a call center.
You know, 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 a bunch of sales jobs in college.
So I did the call center and then after that I worked for adt, cellular alarm systems, door to door.
Those were, those are some interesting days.
And at the time I didn't know it, but like the experience working those jobs completely changed my career.
Omer (07:59.790)
Were you a kind of pretty resilient person at that age?
Or if not, I'm sure going through those types of jobs must have made you a lot more resilient.
Tope Awotona (08:09.790)
Yeah, so when I did a call center job, I would say 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 for ADT and sort of alarm systems door to door, it was the first job I ever had that was strictly, that was all commission.
Right.
So there was no hourly wage or anything.
So like you either sold and you ate or you starved.
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, it 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 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 I would have come back on the fifth day.
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 what the success rate was.
I knew that I could go up to four or five days and not do 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 myself and also taking risk.
Omer (09:23.840)
And then for you sort of landed in a few different jobs, including at IBM.
And they were all sales jobs.
Tope Awotona (09:30.240)
Correct.
So all of my professional career up until I started dabbling into entrepreneurship, they were all sales jobs.
But there were, there were sales jobs in which I was selling to, you know, selling Enterprise software to large companies.
So on the low end you're selling, you know, deals that are in, you know, the six figures.
On the high end, you were doing some deals that are in the seven figures.
And so it's a very kind of strategic.
And your complex sale.
Omer (09:54.630)
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 Calendly.
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 (10:19.200)
Yeah, so I'll run through them very quickly.
But I'll also give you a quick story on how I started my first business.
The very first business I, at least 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.
At the time I got connected with this guy who was a broker representing one of the businesses that I wanted to buy.
We cannot agree on a price.
So this guy is like, okay, this business you're looking to 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 E commerce business, specifically an E commerce business selling projectors.
So he'd done some kind of analysis and figured out that if I built an e commerce 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.
But the reality is you didn't, you
Omer (11:37.690)
didn't sell many though, right?
Tope Awotona (11:38.930)
I didn't.
I didn't.
I did not sell.
I didn't sell many.
But the beauty of the Internet is if you launch something, you put it out there.
It takes a lot to not sell anything.
Right.
And so that was like, that was in some ways while 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 and you put it out there, you will get people who will, who will find it buy, and then over time you can make it better.
Ultimately, what doomed 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 presentations that I gave.
But long story short, 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.
And also, by the way, the margins of the product were really thin.
So we're talking 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 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 yet another e commerce business, this time selling home and garden equipment.
The margins were better.
I put more thought into customer acquisition.
But again, it wasn't really something I was passionate about.
And so as I realized that to scale the business and make it 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 that one failed too.
Omer (13:27.000)
Didn't you also start a dating site after reading about how much money plenty of fish was making?
Tope Awotona (13:33.480)
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 I actually acted on.
I bought some domains.
Yeah.
I created a holding company for it and I bought some books on coding because I hadn't coded in 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 doing it.
Omer (13:57.700)
Got it.
Tope Awotona (13:58.420)
I spent the money to, I spent some money on the idea, but never, just never followed through.
Omer (14:04.350)
And then at some point 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 were going to sort of take a step back and sort of wait for the right idea to come along.
Tope Awotona (14:23.070)
That's correct.
Omer (14:24.350)
So tell me about like calendly, like how did that idea come about?
Yeah.
Tope Awotona (14:28.470)
So After a number of failed e commerce websites, after I would say a week attempt to start the dating website, I realized I was just burning money left and right and I 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 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 force any ideas.
I would let the ideas come to me and this time around I would make sure that it was something that I was pass passionate about.
It also needed to be something I would be fully committed to and not something that I was just doing as a, as a side business.
Right.
Most of the other businesses that I started, they were part time endeavors and there were never really things in which I envisioned myself quitting my job and doing full time.
I thought, whatever.
So I take this sabbatical from starting businesses and the idea of 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 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 those failed 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 said these people are close.
Initially I was telling myself that these people were 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, 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 are this One, as somebody who was in sales all my life, I spent literally my whole entire professional career scheduling external meeting.
I really understood the problem.
One, two, I was, you know, before I went into 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 that I thought I had was having worked at a lot of successful software companies, I actually knew what a successful software company looked like.
Unlike all the other E commerce businesses I tried to start, I didn't know anything about E commerce, whereas I knew a lot about software because I spent 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 were not.
They were clunky to use, they were difficult to use.
And I thought I had a good eye for usability and design.
So for all those reasons I thought I could actually I was well positioned to create something unique and differentiated.
And so I emptied my bank account to pull the trigger.
Omer (17:55.420)
Yeah, I really like 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, almost invalidate it or talk yourself out of it and you can't do that, then there's probably something there that's worth putting your heart and soul into.
Tope Awotona (18:24.310)
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 and 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 business 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 became obsessed with it.
And it was obvious that there was a glaring gap in the market.
Omer (18:57.440)
And did you sort of try to validate it by going out and talking to people or just 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 (19:10.680)
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 did no validation.
But to me, the idea was, 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 say.
In other words, I care less about interviewing people and asking them, do you want a new scheduling tool?
Or 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, and that told me that that's the best validation, like people are today.
Regardless of what I thought of those products, the fact is people were paying for those products, and there were a number of them.
And while they were relatively small businesses, I still thought, in spite of what I thought was not great execution, the fact that 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.
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 validating the idea.
Omer (20:25.310)
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.
Tope Awotona (20:35.200)
That's correct.
Omer (20:35.720)
Right?
I mean, there was.
There was no.
It kind of.
You know, when you and I were talking, like, 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 talked about, like, why you shouldn't have a plan B.
Like, you know, I have to dig that out.
But, yeah, I mean, it kind of reminded me of many ways of that.
So how do you start building the product?
Like, did you start coding yourself?
Did you spend that money to hire some developers?
What did you do?
Tope Awotona (21:08.280)
Yeah, so I hired developers.
But before that, what I did was I had the idea.
I looked on the market, and I saw all the different options.
This is what I did for Validation and discoveries.
I spent a lot of time using all of those products and not only reading them, but also reading through their idea portals and their communities and their forums.
You see what their users are saying.
So a lot of times when people go to create a product 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 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 you're 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 used it myself to really figure out what worked out really well, what did the existing tools figure out so that I could replicate the things that they did really well?
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 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 way in which I was looking to confirm all my own hunches, because I'd done that idea.
I had a really strong conviction at that point.
And so I raided my bank account and I to hire engineers.
The engineers that I initially hired were in Ukraine.
So I actually had to 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 (22:50.030)
And so you looked at these other products, and I think that's smart to spend time understanding what your kind of future competitors do.
Well.
And in terms of the gaps you talked about, kind of, okay, they were kind of either slow or 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 (23:29.840)
So I thought a few things.
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.
So as a salesperson, I thought of meetings a little bit differently in the sense that, like, salespeople understand that when you're inviting people to meet with you, it's not a granted that they'll meet with you.
Right.
And so in some ways, like you still have to come, you have to convince them to meet with you.
And so it's that realization.
One of the things I realized as I looked, 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, a registered user, user of 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 if I make the experience really, really easy for you.
And that's one of the things Calendly got right initially.
So I paid a lot attention to the existing tools on the market.
I looked at how many clicks and how many, you know, 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 users.
So that again, reduced 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 were inviting to schedule with you was just a lot better and a lot seamless, and it got more people excited about using.
People who hadn't used that scheduling tool before were a lot more open to it because the user experience was just really good.
So that was one thing that we bet on.
The other thing was design.
So the time I launched this, we launched calendly was 2013 at the time.
This was 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 its design, both from an aesthetic standpoint and also from a functional standpoint.
And so one of the other things that I think Calendly got right was it looked like a modern tool.
Again, it was more inviting and we paid a lot of attention to design.
So the experience for the invitee design, and then the third thing was integrations, right?
So a lot of the existing tools on the market didn't really integrate with as many of the, of the most important business applications that users care about.
And so I thought that if you, if you did all three of those things very well.
You would have a very differentiated product.
Omer (26:00.230)
How long did it take you to launch the product?
Tope Awotona (26:02.390)
The MVP from it was about six months.
Omer (26:05.270)
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 this 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 (26:32.140)
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 building the 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 Bites, actually.
And so that company was a client of theirs.
And so there was a conversation between the engineers that were working on our product and some of the engineers that were working on the Byte Brights product.
Long story short, people from Brightbytes find out that these engineers are working on this scheduling product and they're like, oh, we have a need for that.
We'll check it out.
The product at the time is not generally available.
Right.
So you can go up to the.
You could go to calendar.com 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 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.
Are the customer success move of Bright Bites.
They're scheduling with people 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 spreads virally to some schools, and they're beginning to use it for parent teacher conferences.
And then it just Continues to grow that way.
So that's how we got our first thousand users until 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 it reduces the barriers to entry to get into the product, and when people use the product, they introduce other people to it, and then you look at the versatility of the product, it can 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 the requests that were coming in and trying to understand why they were coming in and what they were looking to do.
And those led us to.
So those led us to really understand where the segments in which we're more successful than others, and then we just began to double down on those.
Omer (29:01.860)
So in many ways, the freemium model for you, for calendly, has turned out to be one of the best decisions, as you said, you didn't make, Right?
Tope Awotona (29:16.510)
Yes.
Omer (29:17.150)
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 (29:42.990)
Yeah, so this actually goes to.
I'm glad you brought this up.
And this is actually one of the first mistakes that I made.
We launched the 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 to the actual day.
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 two, in hindsight, we should have grandfathered some of the early users, but we didn't do that.
Omer (30:22.160)
But they could still keep using the free plan, though, right?
Tope Awotona (30:24.880)
Correct.
But what was included, the features included in the free plan changed once we started charging.
We repackaged the free plan and removed 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 features.
In hindsight, 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, I guess, appreciation for using the product in the early days.
Omer (30:57.960)
Yeah.
And so kind of, what was the impact of.
Of doing that?
Tope Awotona (31:01.640)
Well, the impact of doing specifically.
Omer (31:07.560)
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 grandfathering those people or did it lead to, like, a lot of complaints or kind of, you know.
Yeah.
Tope Awotona (31:19.280)
So really, the silent majority just was happy that we were generating.
They were grateful for the time in which they were able to use the product for free.
And once we started charging, they just paid for it.
And they were happy that by having a business model that we would 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 very vocal.
But for every one of those that complained, there were maybe 20 other people who upgraded and didn't say a word.
But nonetheless, I think that hindsight swings.
20.
And in the grand scheme of things, like, what, the revenue we gain from not grandfathering those people was probably not worth some of the chaos it created.
Omer (32:06.250)
Yeah.
And I think it's interesting you said that if I had known how big this thing was that I was working on, I would have done things differently here and there.
And, like, when you start to look and 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 (32:42.750)
About 30 million and growing, you know, 100% year over year.
Omer (32:48.030)
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?
Tope Awotona (32:59.470)
That's correct.
Omer (33:01.070)
So I think there's a 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 it'll be like, oh, I'd be happy if I got, like, you know, a thousand customers.
Tope Awotona (33:17.570)
Yep.
Omer (33:20.130)
And then look where you can end Up.
Tope Awotona (33:21.890)
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 is, because I think that in and of itself can also 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 overwhelms some people.
Omer (33:40.880)
Yeah.
Tope Awotona (33:41.920)
So it's an.
There's a.
There's a happy medium there.
Omer (33:45.200)
Yeah, totally.
So, you know, I think it's a.
As I said, 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's been so important to the growth of Calendly.
But I also know that you've talked about it being an emotional kind of roller coaster for you, and I think any founder or an entrepreneur can relate to this where, 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, a lot of those moments were like, after you had launched Calendly.
Tope Awotona (34:52.929)
Yes.
And so, like, for me, the most difficult part, the ups and downs, we really come as we scale of 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, 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 from a clean slate anymore.
Your customers have certain expectations and, you know, they all want different things.
And you hired people and you've made promises to them.
At least they, you know, they've 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 challenging part was I had all these, you know, responsibilities to 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 the business should do.
So all 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 you know what kind of person you needed in the role.
But because you've never hired it before, you, 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, 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 Org 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 recognized them and surrounded myself with really good advisors that helped me see it, and I started to build the team out in the right way, invest in our culture and values, and all those things have just made a difference to kind of putting us back on the right track for.
For growth and also having a fun and exciting work environment.
Omer (36:54.010)
Yeah, I'm glad 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, when you talk about the five people, that was like, five product managers you hired almost at once.
Right.
And so there's a downside to hiring too fast as well, so.
Tope Awotona (37:21.790)
Yes, yeah, absolutely.
Especially when you've never hired 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 role and what kind of 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 unless I've proven that I know what it takes for those rules to be successful in our business.
Omer (37:54.750)
Yeah.
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 calendar offices.
So what is the story behind that, dude?
Tope Awotona (38:07.870)
So the Story behind.
I can't believe you found that.
I forgot about that myself.
So the story is I was interviewing a product manager, and I'm sitting in the interview and in walks Ashton Kutcher.
Like it was not a planned 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.
At the time we were at the Tech Village, and he wanted to come meet with the promising startups in the building.
And, you know, the director of the Tech Village told them.
Told him to check us out.
But all this happened short notice, so I got no advance notice of it.
I think they actually sent me an email.
But because I was in the interview, I didn't see it.
Long story short, I'm in this interview and in comes Ashton Kutcher.
And so I tell my.
The guy that I'm interviewing, who's still with us, who I went on to hire and still with us today, that this is not you being punked.
This is Action Kutcher just randomly showing up in our interview.
So, yeah, that was.
That was interesting.
Omer (39:04.360)
Love it.
All right, cool.
So I'm going to ask you seven quick fire questions just to try to answer them as quickly as you can.
You ready?
Tope Awotona (39:11.960)
Yeah.
Omer (39:12.520)
Okay.
What's the best piece of business advice you've ever received?
Tope Awotona (39:16.600)
I mean, I've gotten a lot, but I still go back to my mom's advice.
That's my favorite one.
Omer (39:21.160)
What book would you recommend to our audience and why?
Tope Awotona (39:23.800)
Oh, one of the books that I really like is Outliers by Malcolm Gladwell.
What I like about it is just it tells the success story of the success stories of people like Steve Jobs and Bill Gates.
Just, long story short, just describes what are the attributes that hyper successful people have.
And it's a fun read.
Omer (39:43.480)
Cool.
So what's one attribute or characteristic in your mind of a successful founder?
Tope Awotona (39:49.480)
Great.
Omer (39:51.400)
What's your favorite personal productivity tool or habit, apart from Calendly?
Tope Awotona (39:56.560)
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 does is it allows you to just do a screenshot and easily share the link and easily share a link that can take people to that screenshot that you took.
So I like it a lot because a picture is worth a thousand words.
If I'm describing something to our product people, I can just share a screenshot or record a quick video and share it with them.
Omer (40:20.690)
Cool.
I'll include a link in the show Notes to that.
I use a product.
I'll give it a shout out.
I've 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 can 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 (40:48.740)
Exactly.
It's the same exact thing.
And I don't know what I pay for monosnap, but if they came tomorrow and said it's now gone up to $30 a month, I would pay it.
Maybe I shouldn't say that on this.
Exactly that.
But yeah, it's a very simple thing, but it just creates so much joy for me every day.
Omer (41:07.640)
All right, you're focused, you're a founder, you're growing super fast, 100% a year.
But what's a new or crazy business idea you'd love to pursue if you had the time?
Tope Awotona (41:19.960)
I have a lot of different ideas, and by the way, I'm not going to pursue any of them because Calendar keeps me pretty busy.
But I think there's an opportunity for a new product in the fitness industry that may be a combination of.
So I'm a crossfitter 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 is a great product, but I think you modify a little bit for the masses, and I think if you do that really well, there's a really good business there.
Omer (41:55.830)
All right, what's an interesting or fun fact about you that most people don't know?
Tope Awotona (42:00.230)
Yeah, so When I was 17 or 18, 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 (42:22.300)
Did you get the patent?
Tope Awotona (42:23.900)
Well, so there's no approval process for a provisional patent.
It's just really provisional.
Omer (42:28.500)
Okay.
Tope Awotona (42:28.740)
Yeah.
It's a way for you to bookmark the idea.
But I didn't follow through actual patent.
But, yeah, I did that.
Omer (42:35.140)
Finally, what's one of your most important passions outside of your work?
Tope Awotona (42:38.220)
You know, I'm a very curious person and so I like traveling.
You know, it's a chance to help me satisfy my curiosity.
Another issue that I'm passionate about is just improving diversity and inclusion in the tech space.
That's not something 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 (42:58.660)
Cool.
All right, so if people want to find out more about calendly, go to calendly.com and if people want to get in touch with you, Tope, what's the best way for them to do that?
Tope Awotona (43:07.860)
LinkedIn.
Omer (43:08.500)
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 (43:17.490)
I did as well.
Thank you so much for having me.
Omer (43:19.490)
Yeah.
And as you know, as I mentioned, I'm a calendar customer and a big fan.
I love what you guys are doing, and, yeah, I'm excited to see how the product keeps evolving.
Tope Awotona (43:29.010)
Thank you very much.
We'll keep it cranking for you.
Omer (43:31.890)
I appreciate that.
Yeah, make sure everyone's busy.
Cheers to all the best.
Tope Awotona (43:37.970)
Take care.
