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Tope Awotona

Impatiently Scheduling Our Calendars, One Meeting at a Time

By Atlanta Ventures

May 31^st, 2018

It’s Monday. Wednesday is our scheduled time (via Calendly) to dive into the entrepreneurial journey of Tope Awotona, CEO of Calendly. I send him a text making sure we’re still good this Wednesday afternoon.

“I got you” he says in a disarming and endearing way. That’s what you get with Tope. He is impatient, smart, charming, with a good ol’ fashioned chip (block)-on-his-shoulder, and is out to prove to the world that Calendly is more than “just a feature” or “something that can be copied overnight” as he’s been told before.

“Birdsong, we’ve got quarterly goals to hit. How long is this going to take? Can we keep this to 30 minutes?”

I understand.

I meet Tope on Wednesday in his spacious, glass-glazed office he leased from a premiere Atlanta architecture firm. This April afternoon in Georgia is reminiscent to an overcast day at The Masters. The sun struggles between the clouds, but the temperature couldn’t be more perfect, and the trees couldn’t be greener. Those same trees partially obscure the overlook to the High Museum across Peachtree Street. From Calendly’s office, it’s almost as if the flyover shot of the “London Museum” in Marvel’s Black Panther was filmed from their break room. When you look around, Calendly employees are relentlessly focused in their office in the trees.

We grab a beer or two and sit down for our interview.

“Okay, let’s rock.” Tope says with excitement.

Tope Awotona

Odds are good Tope Awotona and his team of 60 employees at Calendly have somehow touched your calendar within the last 5 years. This year alone, Calendly will serve over 30 million people. What many outsiders thought to believe was a simple feature at first, Tope has turned into a viral, SaaS sensation.

To understand Tope and his matter of fact nature, it’s important to know his story. Our friends at Atlanta Tech Village dove deep around his upbringing and family story here. His story moving to the States could have started with him going directly to college at age 15, but his mom wouldn’t allow it.

And that’s where we’ll start...

Tope Awotona

Jon Birdsong: You’re 15. You could go to college, but your mom said “no.” So what did you do from 15 to freshman year?

Tope Awotona: I ended up taking more classes at Wheeler. I went there for two years and then from there I went to The University of Georgia where I started off as a Computer Science major.

JB: Did you want to go to college at 15?

TA: Absolutely I wanted to go. I’ve always been crazy impatient since I was a kid. In my mind, I was thinking I could done with college sooner, and you know, start a business, do whatever, start my career earlier.

JB: Did you start a business in high school?

TA: No. I thought about starting a business but I didn’t.

JB: Why not?

TA: Just being a kid. I guess another big reason was the fear of failure and I also thought the ideas I had just weren’t that good. So I’ll give you an example. One idea I had was charge my friends to come play video games at my place, so basically create an arcade in my mom’s basement.

JB: Hah!

TA: I mean it was just an idea and I never did it. The confidence in my instincts wasn’t there.

Looking back on it, the first attempt of starting any business was my freshman year at college.

JB: You’re at UGA. Did you look at any other schools?

TA: I applied to Georgia and I think I applied to Georgia Tech but I missed the deadline. So that’s another thing. Being the child of foreign parents who didn’t really grow up in the system, I didn’t fully understand the college application process. I just knew I needed to take my SAT’s and then applied. I also applied to Kennesaw State.

JB: So you weren’t leaving the state.

TA: Correct, I was not leaving the state. I thought about going to Stanford, but I didn’t think I could afford it. The cost of travel, the tuition was ten times higher than Georgia, I’m away from family. I just didn’t think I could afford it. Which I was right.

So I end up going to University of Georgia on HOPE scholarship and the very first idea that I actually took any action on was -- in high school and in college, I worked at CVS. I had a number of jobs there. I was a cashier. I worked in the photo lab, but inevitably what would happen was at the end of every night, the manager on duty would have to reconcile the cash register: count the money, look at what the computer says, review the total number of transactions each register did and make sure there was the same amount of money in the registers that there should be.

That process is like an hour for the manager every single night and I thought to myself wait a minute, what if you had a register, where instead of having the register open to the cashier, what if you had some machine where the customer actually feeds money into the machine, so the money never passes the hand into the cashier and therefore they never touch the money. This would prevent what managers called “leaking” and reduce the opportunities for cashiers to steal or make mathematical mistakes and also create a quicker closing process at the end of the night.

So that was my idea, to retrofit existing registers in this manner.

JB: Did you take any action on it?

TA: I did. I found a patent lawyer. I found some guy in Cumming, Georgia.

You know, where all the good patent lawyers come out of.

(We both start laughing)

Tope Awotona

And so I gave this guy a few thousand dollars and he was like, “You have a great idea but to really file a patent you’re going to need thirty thousand dollars”, and I didn’t have it, so what I ended up doing instead was filing a provisional patent, which was a placeholder saying I was going to get the patent.

So then what I did, was I called NCR, and I said “Hey, I have this invention for you.”

JB: This is still freshman year of college?

TA: Still freshman year. So I call NCR up and I’m like “You guys are the king of registers. I have this invention that’s going to revolutionize how cash registers work, and I’d like to tell you guys about it and see if you’re interested in going to market with me”. Somehow—I forget how the series of events went— I got connected to a lawyer in their IP practice and Corporate Dev. Department. I had a conversation with him and said I already had a provisional patent filed—which is partly more than I should have shared at the time, but anyway—he ended up telling me, “Well, why don’t you fly up to Dayton?” They were headquartered in Dayton at the time. I was like “Actually, I can’t do that, you know, I’m just a 17 year old kid,” and he’s like “Wait, what?”

Laughs from all

So I actually got discouraged after that and didn’t make anything out of it.

JB: So you spent two or three grand on it?

TA: Yeah, something like that. But looking back on it, knowing what I know now, I could have developed the idea a little bit further and I could have monetized it in some kind of way. I think I could have sold it to them, because they would have bought it for defensive reasons.

That was my first actual idea that I took considerable action on.

JB: That’s freshman year in college, what’s sophomore?

TA: Nothing after that.

JB: So typical college experience after that?

TA: For most of my life, school came to me naturally. But over time, as I began to take more difficult subjects, I realized that not exercising the study muscle definitely affected me, so I started doing discrete math, which you couldn’t just show up and be good at. I started to go from consistently getting A’s, to getting some B’s, and getting some C’s.

Towards the end of college I started to realize, no matter how gifted one is, you can be gifted and get away with a lot of stuff, but if you’re going to be in the elite group of people, you also have to supplement that with crazy work ethic.

JB: When did you start applying that work ethic?

TA: Towards the end of college and at the start of my professional career.

Tope Awotona

Tope Awotona

JB: Let’s start about the transition to the professional career. I saw on LinkedIn you started at IBM. How did you get there?

TA: I actually started working at an Internet Travel Agency. By the nature of the small business, I helped with a lot of different things, but essentially what I did was I sold trips to people.

JB: Why did you go into sales post Management Information Systems (MIS) degree?

TA: Ah, that’s a really good question too. Let me backup a little bit. So I started in Computer Science.

JB: Does UGA have a Computer Science program?

TA: It absolutely does. Laughs

JB: It is MIS?

TA: No, it’s got a legit Computer Science program in the school of Art and Sciences, not in the business school.

JB: So are you an engineer?

TA: Our engineers definitely wouldn’t call me one. I wouldn’t get a second interview at Calendly for an engineering position, but I’d definitely get the first interview.

JB: You’re a product guy?

TA: Haha, I know enough to call BS on engineers and enough to tell the business people, “Hey, what you’re looking for is going to take 10 years to build.”

But, I was in the Computer Science program and I loved it. It was so fulfilling for me to be to write code that was able to take your instructions and turn that into cool stuff.

JB: What do you have to say to all the Georgia Tech folks reading this who are still laughing at the idea of UGA having a legit Comp Sci program?

TA: I’d rather keep that to myself.

Laughs

JB: But long story short, the program was good?

TA: The program was good, I enjoyed it. What I didn’t like was, by year two, it started to wear down on me in that, I didn’t feel like I had a lot in common with the people I was in class with. Their interests were very different from mine. I was a bit more outgoing than the average Comp. Sci. student. But what also happened, was as we were taking more projects, they required really long nights and really long weekends, and I didn’t mind that, but I didn’t like being behind a computer that long.

Sitting behind a computer and debugging this code didn’t completely engage me. So I started having second thoughts thinking, “Yes I can do this, but is this really what I want to do with my life.” And then fast forward in the summer, I took a job selling alarm systems door-to-door for ADT.

Tope Awotona

JB: Why?

TA: Because I thought it could be a decent paying job and I thought I’d like the challenge of sales. So the first day I started, I made $500 in one day, and for a college student, that is a lot of money and I enjoyed it.

I enjoyed the hustle, I liked the immediacy of the reward and I also liked interacting with people. I liked learning the skill of persuasion.

So with that, just between sophomore and junior year, I looked at how happy I was with that job—you know, selling people—versus how happy I was sitting behind a computer cranking out code, and I knew I couldn’t code for a living. But I still decided I wanted to be in technology, because I love the problems and I also felt like that was what the world was being powered by—software and code. I instinctively knew that’s where the world was going to be and where it was moving to.

From there, I landed on MIS as a compromise for interfacing between business people and technical people. I thought I could be an effective go-between between those two people. That was why the MIS degree was great for me and when I graduated, it was during the dot com bust, so technical jobs were tough to find. Looking back on it, maybe I was similar to many young people that I interview today. There are a lot people who are incredibly smart and are incredibly driven but maybe don’t know how to package their skills and sell themselves effectively.

So with that I went with the travel agency out of college.

JB: Did you meet them at a job fair or was it a cold call?

TA: I found it on the internet, likely through Monster.com or CareerBuilder.com. I applied, got the job, and I thought it was cool. I got to go to all these fancy resorts that I would have never been able to afford myself. I made great money for a kid coming out of college.

JB: How long were you there?

TA: I was there for 4 years.

JB: Selling?

TA: Selling.

JB: Straight Selling?

TA: Straight Selling.

JB: Were you building anything?

TA: No. No business ideas.

Tope Awotona

JB: What type of deals were you closing?

TA: I was selling travel packages. Luxury travel experiences. They were $5,000 trips and you were selling to consumers.

JB: Did you have a list or daily call number?

TA: Most of them were warm leads. My boss had some very strong keywords and was able to build significant inbound traffic. I didn’t connect the dots to Calendly’s go-to-market—obviously at the time—but at the end of the day, I was converting people.

I enjoyed the job, but I knew I wanted to go down the path of getting back into technology.

JB: Were you #1?

TA: Number 2 (out of 10) but mostly because the other person had been there for a very long time. And I’m still good friends with my old boss.

JB: Why did you spend 4 years there? That’s a long time.

TA: It was a fun job and I was making good money and I enjoyed being able to see the world. Most importantly though, I knew there was larger vision but being 24, I wasn’t sure exactly what I wanted to do so I passively interviewed in year 4.

At the time I considered pharmaceutical sales. Being the son of a pharmacist, I flirted with the idea of pharmaceutical sales, but ultimately decided to go into software sales at IBM.

JB: Then you went to the biggest technology company in the world.

TA: I did. I literally applied off the website and got the call from the recruiter and progressed through the interview process.

So I go to IBM and I’m essentially a hybrid SDR and I’m just dialing for dollars. For me, I waited a long time to get this opportunity and I wasn’t going to take it for granted. So I was just dialing for dollars.

JB: When you say dialing for dollars, explain what that means to you.

TA: I always had the top call volume—I forget the number specifically—I also picked up the phone a lot faster than most other people did. I also learned and understood the different operating systems. The product we sold was really technical. We were selling backup storage software, so most people had a tough time getting comfortable with it.

JB: You spent a year and half there. Why did you leave?

TA: I wanted to be an Account Executive and it would have taken me 10 years at IBM, but I was going to be less patient, because I had been really patient in my first 4 years.

JB: But you’re an entrepreneur, why didn’t you start something while you were at IBM?

TA: I didn’t think about that. I didn’t think about that at all.

I always knew I wanted to be an entrepreneur, but I didn’t have a timeline. I didn’t really spend a large amount of time thinking specifically how I wanted to do it. I knew I generally wanted to do it.

My mindset at the time was probably not that different from a lot of people my age at that time.

JB: But in the back of your mind, you were like “One day I’m going to start my own business?”

TA: I forgot that I even wanted that for a long time.

JB: What was the state of your entrepreneurial muscle?

TA: It was definitely weak. I was too focused on the day-to-day and I also didn’t feel like I was incredibly good at anything yet.

I didn’t feel like I was ready. I didn’t feel like I knew what I needed to know to help me be successful. I didn’t have convictions around what a great product would be, what a great service would be, how do you have a great model for distribution, for customer acquisition, for customer retention. I didn’t feel knowledgeable about any of those topics. Long story short, I didn’t feel like I knew anything.

Tope Awotona

JB: What did you know at 25 (knowing that you started Calendly at 32)?

TA: I knew I could sell. I also felt like I could understand what I was selling better than most sales reps. I never thought about how those would translate into starting a business.

JB: So a year and half at IBM, your call volume is out the wazoo, and then you were like, “I need to go be an AE.” Was there something that clicked that said that?

TA: So going back, I’ve never been a patient person. I was patient during my 4 years at the travel agency, but that was because I was very selective with my next move. Now I had IBM on my resume and I wasn’t going to wait around 10 years to become an AE. I still have lots to accomplish.

JB: Is that sense of urgency innate?

TA: Yes, I think so. It became more acute in my mid 20’s.

JB: Where did you get it from?

TA: My mother. When she talked about getting something done, it was expected to be done right then. She was like, “If it needs to be done, it needs to be done now, or not at all.”

JB: What were you impatient for?

TA: Challenge. I wasn’t solving anymore problems.

Tope Awotona

Tope Awotona

Tope Awotona

Tope Awotona

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Solving problems is a recurring theme for many entrepreneurs we talked to, including Craig Hyde. In the midst of our interview, the irony dawns on me. Here is this entrepreneur who has self-identified himself as extremely impatient, yet the problem he’s solving today brings calendars structure and order — an impatient person’s last priority.

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Tope Awotona

JB: So you started to look around?

TA: Correct, I began networking.

JB: You don’t seem like a “networker.”

TA: I’m an efficient networker. I met people who could hire me that I could add value to. I tried to make as many of those connections as possible. Soon, many of those people started recruiting me. They would say stuff like, “Hey, we think you’re one of the good guys over there. If you’re ever interested in coming over here, I think we could make that happen.” Just hinting at it and stuff. So I tried to create as many of those conversations as possible.

Interestingly enough, my girlfriend at the time lived in Kansas City and she would tell me about this company called Perceptive Software, she always explained it as the Google of Kansas City. She was like, “You should apply to this company in Kansas City.” I applied and started hunting down the hiring manager and was like, “Hey, I just applied and I also have a lead for you.” They just loved my hustle and they hired me.

Tope Awotona

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Perceptive Software changed Tope’s life. He attributes Calendly's success directly all the way back to Perceptive (4 years before Calendly was started). A number of things happened at Perceptive that changed and put him on the path to start Calendly.

When he interviewed there, the culture attracted him most. The culture was one where you worked with a lot of smart people who are the best and brightest from different fields and different functions. He knew he’d be working with top people and learn from them. The environment was fun but difficult. The goals were aggressive. The pace of growth aligned with his ambitions.
During his time, the founder of the company did a founder talk where he sat down to tell the story of the company. As he shares the genesis of company, it dawned on Tope: there are many ups and downs around the story of the company, and in the end, as long as you have enough perseverance, you can make it.

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Tope Awotona

JB: What other takeaways did that talk provide?

TA: It opened my eyes that people who start great companies are very human and very ordinary in most ways. What is extraordinary about them is they take action. They see something and they grab it rather than wait for someone else to come fix it. And then of course, there is a lot of uncertainty along the way and they learn fast and they adjust and they just figure it out. That was an aha moment for me. That was the first time where I was like, you know what, entrepreneurship is attainable for me. These people are smart and I think I’m just as smart as they are and I can do it as well.

I didn’t do it while I was there, but I started to play around with some ideas in my head. I played around with an idea for a dating website. I never actually started the dating website, but I certainly thought about it.

I ended up leaving that company and coming back to Atlanta.

JB: Were you closing stuff?

TA: Oh yeah, I was crushing it. All together there were maybe 40 Account Executives and my second year there, I was one of the top 3 reps in terms of dollars closed.

JB: Do you like sales?

TA: Yes.

JB: Do you have to sell today?

TA: All the time. You’re selling to candidates. You’re selling to customers. You’re selling to employees. I sell in different ways.

As I moved back to Atlanta I started working for Vertafore. Vertafore is the parent company of ImageRight, a company in Conyers. About that time, I really started thinking, okay I’ve got some money saved up, I think I’m ready to do this. By then, I felt like I learned enough skills to get started. I had seen small companies, I’d seen massive companies, I’d seen mid-size companies. For example, at Perceptive when I closed deals, I had to work with legal to get contracts amended. Most people would take a passive approach to legal and just be g- betweens. I would actually work on the amendments myself and present it to legal team. Through this process, I got very comfortable negotiating very complicated agreements. Same thing which accounting. I became a student of accounting and how revenue was recognized so I could structure deals appropriately.

JB: Was there some big, grand vision you had as you were packaging up these skills?

TA: When I was at Perceptive, no.

JB: But you still weren’t patient, and had massive ambition... towards what?

TA: What I always had was insane curiosity. I wasn’t scared to learn new things.

So, before I moved to Vertafore, I tried a few things. Starts laughing

Tope Awotona

JB: Oh boy, here it is. Tell me more.

TA: I had an e-commerce website called ProjectorSpot.com.

JB: Can we talk through the thought process on this?

TA: Yes. So ProjectorSpot.com. Let me tell you how I got to this company. So I decided that I’m going to start a business. Well, first I decided I’m going to buy a business. So I go to Bizbuysell.com, where you can buy businesses for sale that people list online. So I find a couple businesses that I’m interested in. One of the businesses I’m interested in, I get connected to this business broker and we’re negotiating for this business and we just can’t come to terms. It was some e-commerce business, but not ProjectorSpot.com. Between the back and forth, the business broker was like, “Hey, I can see you’re not comfortable buying one of these businesses at this price. I’ve built multiple successful e-commerce businesses. Why don’t you just start your own.” He was like, “I can help you start it, I’ve done it before.” He said, “Here’s the process I go through.” He proceeded to share how the best businesses rank highly for keywords related to the products they are selling. He said, “When most people start a business, they say, ‘I’m going to sell X!’ That is the worst way to start a business. The right way is to first find keywords that you can rank highly for, and then try and find a collection of keywords, and then think about something you can sell into those keywords.”

He did all the analysis and came back with six keywords. This is in 2010.

He was like, “Projectors are the business. Margins won’t be good starting out, but as you get more traction, it will.”

JB: How many hours a week are you spending on this?

TA: Not much, like 10 hours a week. He did a lot of the groundwork. With my current job, there was no way I could spend 60 hours a week on this.

So we launch it. A few sales trickle in. This is the beauty of the internet that I realized. I started this thing ProjectorSpot.com, nobody knew who was behind it, people would go online and then purchase projectors from it. So that was amazing.

What I realized quickly, was that people who wanted to buy projectors wanted to be educated. People were going to ProjectorSpot.com to learn about projectors before they buy. I realized, for me to get good at that, I needed now to create educational content and I needed to learn about all different projectors. Long story short, I realized for me to get good at that, I needed to learn a lot more about projectors, and said to myself, this is not going to be a passive thing. It’s going to take work to grow this and it’s going to take a long time to grow this and, by the way, the margins suck because you’re selling someone else’s stuff.

JB: All in all, how long did you spend on this?

TA: 6 months. Very quickly, I realize that I didn’t think through how I would consistently get customers. Most people who start business, me included, think that once they build it, people will just show up and buy. Until you have your first failure, you don’t realize what customer discovery truly is and there is big difference between doing it right versus doing it in a superficial way.

So I decided to shut it down.

I’m still selling at Vertafore and making good money.

Tope Awotona

JB: Are you making 6 figures?

TA: Yes, at Perceptive I was making 6 figures and made even more selling at Vertafore.

After my time at Vertafore, I actually did start one more business called YardSteals. It was just like ProjectorSpot but slightly better. It was home and garden yard equipment, but I ran into the same problems at ProjectorSpot.

Any of these could have worked, but they required a lot more work than I anticipated.

What I learned most from the whole process is there is no way to passively build a successful business. You’re either all in or you’re not. There is no in between.

JB: After two years at Vertafore, you go and sell at EMC. When did you move from e-commerce (ProjectorSpot / YardSteals) to SaaS (Calendly)?

TA: This is where it starts to get interesting. So I’m selling at EMC and trying to coordinate calendars. All of a sudden, I’m like “this whole experience is awful! I’m trying to schedule with this guy and it’s taking forever.” So I was like, “I’m going to sign up for this app to help me coordinate times.” I tried one and it didn’t satisfy my needs. I tried like 10 others and none of them worked the way I wanted them to. The more I dove in, the more I was unsatisfied.

JB: Was this 2 weeks into EMC or a year into EMC?

TA: Let me take a step back. I paused all of these businesses and said to myself, I had started a business for all the wrong reasons. I started a business because I said I wanted to start a business. Instead, I should have started a business because there was big problem that I saw and had the desire to fix and was passionate about. It was a huge learning moment. So I decided I was going to go on a hiatus indefinitely until something big came to up.

JB: So you put it out to the world, “Hey, I’m ready to solve some serious problems?”

TA: Yes, I was going to be on the lookout, but I was going to be a lot more selective in the problems to solve. I run into the scheduling problem. At the time, I’m not immediately looking to start a business. It’s just something I’m looking to solve for my job so I can be more productive. Overtime, as I see the market taking shape, I’m still not satisfied with what’s out there and yet many of them have lots of customers. People are paying for their products. I know they are because I see their support portals and see them say, “I’m paying all this money and you’re not doing this, you’re not doing that.”

JB: Was there a moment where you were like, “Damn, I can go do this a lot better?”

TA: Yes. Unlike a lot of the other businesses I started, I didn’t know a lot about e-commerce, but software... I’ve sold it, I supported it, I’ve written contracts for it, I’ve learned how it was made at UGA. I was like, “This industry is something I actually know a lot about.” And just like that, I said, “Let’s do it.” The idea was clear.

Tope Awotona

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A year after Tope had shut down his e-commerce stores, he moved to more sales at EMC. The entrepreneurial muscle is beginning to strengthen after being weakened through his e-commerce attempts. The problem of simple scheduling comes to him as he’s doing too much back and forth in his most recent role at EMC. He feels teed up perfectly to solve the scheduling problem. The moment to make the full time jump to Calendly is nearing…

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Tope Awotona

JB: How did you start Calendly?

TA: I didn’t start off with a position that a business needed to be started. I started off with the position that this problem needed to be researched. I needed to understand the depths of the problem and understand where there was an opening in the market.

JB: Where was the opening in the market, besides better support?

TA: I thought the existing products did not look good. Keep mind this was early 2013. At the time, Apple was kicking ass and everyone was beginning to pay a premium for design. I felt like a lot of the existing tools at the time looked and felt like they were built in the 80’s. I thought users in 2013, wanted better usability, better user experience, and things to look good, and I thought I had a good eye for that. During my time at Perceptive, I demoed the software hundreds upon hundreds of time. In demoing a lot, I learned how to tell the story of a product and how people came to understand software. And, by the way, I think that is a great skill for anyone to have, but that’s how I learned a lot about usability. In demoing software, you can show them all the features, you have to be able to roll it out to the customer in a way that makes sense their business process and workflow, and that, by the way, is why I felt like I had good instincts around usability and user experience.

JB: So was the first step? You making designs?

TA: It was not. I was not committed to making the designs yet. I was committed to do as much research as possible. The more I did the research, the more I became convinced there was a huge gap in the market. After I drew conclusions, I decided I needed a technical co-founder so I could build this.

Oh, let me step back. Before I made the decision to get a technical co-founder, I sketched out and made a very detailed list of product requirements. From all the observations of my research, here’s what the winning set of features would be, and then I began to seek out a co-founder.

JB: Everything is spec’d out, now you’re looking for a technical co-founder. So many entrepreneurs are looking for technical co-founders. How did you start that process?

TA: First thing I did was reach out to my network. There was an old co-worker who was one of the lead engineers and we’re friends and he’s a brilliant guy. And I was like, “Hey, we should do this together.” I liked him, but it never panned out.

JB: Why didn’t you build it? You do have a Comp Sci background.

TA: I could have built it, or at least some of it, but I didn’t have the time. I needed someone else to build it and to hire someone to do it.

JB: So how much do you have in the bank at the time? $100k?

TA: More like $200k.

JB: Were you ready to put it all in to the idea?

TA: Definitely. I was ready to put all of it into it. All of the other ones, I was trying not to lose money, and this one, I was ready to put all the money in, and borrow some to get this off the ground. I was ready to go.

Looking back on it now, it could have been so bad.

Laughs fill the room from both of us.

And also with the past failures, I knew what failure felt like.

I couldn’t find a technical co-founder.

JB: Why couldn’t you find a technical co-founder?

TA: Well I couldn’t find a technical co-founder because all of the best engineers are making a lot of money, and from my experience, most of them have a lower tolerance for risk than business people do and the ones that don’t have a low tolerance for risk, just feel like they can build it themselves and they don’t need to share ownership with someone else. Also, I think a lot of people approach them. I think that is why it’s difficult.

Now, I also think if you’ve done it before, it’s less difficult for those people. I think that is one thing that could put you head and shoulders above everybody else.

JB: But not finding a technical co-founder didn’t stop you?

TA: That’s right. I was going to get this built. So I start researching, looking for different people. I talk to local dev shops. Got it spec’d out. Many shops just immediately want to know if you have money. Many of the dev shops were motivated by the amount of money they would get from the project and they were more concerned about whether I could pay them or not, than they were excited about bringing this idea to life, and launching it, and serving customers, and changing the industry.

The company I did find was a partner from day one. Obviously they want to get paid, but they were more excited about what we could build together.

JB: And how did you find them?

TA: Internet research. Basic Google Searches for Ruby dev shops.

JB: What made you pick them?

TA: Every time I got on the phone with them, I learned a bit more about the process. They were excited about the work and very knowledgeable. Eventually, I flew to Kiev to meet them. We had an intense 2-day planning session where we scoped out the entire project. It was intense because we had to make a lot of decisions about which calendars do we integrate with and when and much more.

JB: Initial quote?

TA: They didn’t give me a specific quote. They provided a rate and then clear process of the order we should build stuff.

Tope Awotona

JB: Did you think you’d ever raise money?

TA: I did not.

JB: How long did the MVP take?

TA: We start building in early 2013 and we launched the product in September 2013.

JB: When did you move into Atlanta Tech Village?

TA: November 2013.

JB: So 9 months to build the MVP?

TA: A little less. I was very involved in the design, so that took some time and then, I’ll say this, the designer who worked on the MVP, well, well, how do I say this...he’ll never forget me. It doesn’t matter what he goes on to do, he’ll never forget me.

Laughs

JB: Product takes 6ish months. When did you get your first user?

TA: I would have to go into the database but it was probably August or so.

JB: You thought about Calendly’s go-to-market in the designing of the product. How did you get your first customer?

TA: Well, we recognized, if we built the product right, that if you scheduled a meeting through Calendly and enjoyed the experience, then that person is more likely to use it too. So people were connecting the dots themselves, but our next question was “How can we make that happen even more?”

Regarding the first couple customers, what happened was, the first users were also clients of the dev shop. So the product was not generally available. It was public, we just didn’t hide it. No one knew about it. Somebody else was in the dev shop and telling a client about it and that client was like, “Oh! Our customer success team needs that.”

JB: This was the ultimate field of dreams, “If you build it they will come?”

TA: Yes. But it took decades of learnings and observations to get to this moment. So the first person signs up and of course there are issues with the product. It’s not ready yet.

JB: And at this time you’ve put $100k into this?

TA: Close to $200k.

JB: At what point were you like, “I need to go raise money?”

TA: When I ran out of money.

So the first customer signs up. And they used it and had no idea it was super early. This customer was selling educational software, as they would schedule time with teachers or instructors and those people would turn around and use us for parent-teacher conferences and other things.

Tope Awotona

Tope Awotona

JB: It seems like the first few customers were out of left field. Did you build this to scratch you own itch through your sales experience?

TA: This brings up a really good question. At the time I was building, I didn’t think about who I was building it for. I thought about the functional requirements, but I didn’t pigeon hole myself just for sales reps.

JB: Why?

TA: I focused on simplicity. We needed to make it simple for people to sign up and share links.

I knew it was a massive market and I also knew people were still being introduced to automated scheduling. If you put too much work on it, they would drop out of the funnel and they wouldn’t want to engage with it. By the way, these are the same concerns salespeople have. Inadvertently we built it for salespeople and customer success people and anyone in customer facing roles.

JB: So now you’re at the point with the business where funds are getting low, but the product usage is growing and customers are increasing. You’ve just moved into Atlanta Tech Village. Do you have paying customers or no paying customers?

TA: No paying customers. I was letting everyone use it for free.

JB: How long were you going to let them use it for free?

TA: Until I raised money. Laughs.

JB: Why did you move into the Village?

TA: As it began to grow, I knew I was on to something big. Somehow I heard about Startup Chowdown and I just went to it. In going to Chowdown, I saw the Village and it reminded me a lot of my days at Perceptive and I knew I needed to be there.

JB: This was before the renovation?

TA: Exactly. Once I went to Chowdown, I just wanted to be in the Tech Village. In the back of my mind, I was also thinking about, how can I be around people who I can bring on the team who get SaaS and also help me build the company into something big.

Once I got there and I saw the energy and vibe and the kind of people who are building real SaaS businesses, I was immediately attracted to the idea of setting up shop.

JB: The users are growing fast now, it’s early 2014, you’re running out of money, and you’re still not charging. When did you decide to start charging?

TA: I wasn’t initially concerned about charging.

JB: That sounds nuts.

TA: I was worried about charging but, I kept feeling like, I needed to get to a point where I needed to build more before I could charge. I wanted to charge people, but just didn’t feel like we were ready.

JB: So you’re telling me you should have charged users earlier?

TA: I think we charged people at the right time but we could have charged earlier. Both laughing.

Tope Awotona

Let’s talk fundraising.

Tope Awotona

JB: You raised money from DC (David Cummings)?

TA: The Great DC.

JB: How did you approach that conversation? Did you cold email him?

TA: No. Here’s what I know what I did. I learned about the Accelerator in ATV at the time, and I began to fill out the application and during the process, I had a change of heart.

JB: Why the change of heart?

TA: Because I was on the fence. I felt like I had come so far with my own money that I didn’t want to get diluted. I felt like I had come so far, put so much into it, and done so much of the hard work. So I filled out the application, I did not complete it. I was just on the fence.

But, someone in the building was using Calendly and tweeted about it. David saw the tweet and we connected after that.

After getting connected, we had many meetings afterwards and I enjoyed meeting him and learning from his insights. I also felt like his brand was good for Calendly and I also felt like I could learn a lot from him and I would enjoy working with him as well.

JB: Has his investment in your company been worth it?

TA: Times a million. If I could do it all over again, there is nothing I would change. Let me put it in another way. If I had the money to fund the business myself and did it myself, the business would not be at the level it is today.

JB: How so?

TA: I think the business would have grown. I think it would be a profitable business and still be in existence today, there’s no doubt about that. I do think having someone who has a positive way to apply accountability is key and there’s a perspective aspect. There are times in which entrepreneurs are thinking too small and there are times when entrepreneurs are trying to take on too much and there are times when you’re not looking around the corner at what’s next. I think there are times in which you need to recruit people, and you’re in this tiny business and no one knows who you are, it’s helpful for other people to see that successful people believe in you and the future of the business.

-----

Today, Calendly has an 8 figure run rate and is growing 100% year-over-year.

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JB: What’s ahead?

TA: We’ve done a lot that we’re proud of, but we feel like there is a lot more we’d like to do.

JB: Before we go, what’s the biggest sacrifice entrepreneurs have to make?

TA: Stability and certainty.

JB: Do you have a chip on your shoulder as an entrepreneurs?

TA: Absolutely.

JB: What are you trying to prove?

TA: A lot of people didn’t think the world needed another scheduling tool. A lot of people still see what we do is a simple feature or a simple concept.

JB: What do you have to say to a lot of those people?

TA: I’d like to invite them to our website and see the stories of growth we facilitate and all the lives we effect daily.

Tope Awotona

JB: Last question, you’ve been impatient at each stage and step of your life. What are you impatient about today?

TA: I’m still impatient about the company’s growth. The best entrepreneurs always feel like things can get better. I don’t feel like I’ve made it. I don’t feel like the company has made it. There is still significant room for advancement and growth. That is what I’m impatient about.

Tope Awotona

------

We’re over two hours into the interview. A full hour and a half longer than Tope wanted. It’s around 8:00 p.m. Those quarterly goals he was elaborating about two hours prior, momentarily seemed to take a back seat as we spent time reminiscing about his journey. In a world dictated by calendars, it seems like the moments where most of the magic is made doesn’t have a time slot.

The impatient CEO will never schedule time to pull an all nighter. The moments of relentless proactive action never seem to have a meeting invite.

Perhaps that’s the secret of building a great company that Tope truly has discovered: true innovation happens between the meetings. The game of inches every entrepreneur plays is won or lost outside of the regular playing field. Regardless of any single takeaway, one thing will remain certain, Tope Awotona and his passionate team will remain impatiently focused on continuing to build Calendly’s Kingdom, up in the office in the trees, right across the from the High Museum.

Tope Awotona

Footnotes

Story by Jon Birdsong | Photos by Luke Beard

FootNotes

Story by Jon Birdsong | Photos by Luke Beard

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