ICYMI: Meet Tope Awotona, Calendly’s Founder and CEO

April 23, 2020

Welcome to the very first edition of In CASEYou Missed It, where I take a brief break from my Weekly Walks to get to know some of the most interesting and innovative personalities behind the greatest startups in the world.

Today we’re talking to Calendly Founder and CEO Tope Awotona to find out the best book he’s read in the last six months, what he’d be doing if the internet didn’t exist, and which actor would play him in a Calendly movie.

How do you explain what you do to parents, friends and kids?

I say, “We make it easy for business professionals to meet.”

Who is your favorite superhero? And what would your superpower be?

Do you know the comic Tintin? It’s not a superhero movie, but he’s this really cool kid detective. So what would my superpower be? I’d just be an awesome detective. I can crack any case. I can crack any code.


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If there were a Calendly movie, who would play you?

I don’t know any actors!

What pop culture trend could Calendly solve?

Imagine you meet somebody online and you’re super-interested in hanging out with them and the feeling is mutual. Maybe Calendly could solve that.

What’s the most useful tool you’ve discovered in the last year?

Right now, I’m loving the reMarkable notebook.

I like taking notes in meetings. I don’t like typing them, because I feel like it takes away from the meeting and you become engrossed in your laptop. So I like handwritten notes, but at the same time I want the benefits of having it digital so that it can go with me wherever I am. And the reMarkable notebook does that. It’s given me the memory of an elephant.

What’s your morning routine?

When I wake up, I stay in bed for the first 15 to 30 minutes to read The Wall Street Journal and The New York Times.

Then I get out of bed, get coffee, get ready for work, and start working. I like to start work as soon as possible in the morning.

Is there something you’ve learned in the past six months that you think everyone should know?

I read The Power of Moments, a book that I think everyone should read.

Here’s what it’s about: When people describe their lives, they usually describe the biggest transitions in their lives. People talk about, “I got married at this time,” “I started high school on this day,” “I started college on this day,” “I graduated,” “My first job was this.” The book is more or less about people who transition to very important times, events, or people in their lives.

The more you know about the anxieties that people feel when they’re about to make these transitions, the more you can help them make those transitions successfully. So when people start a new job, they’re anxious about a lot of different things. They’re concerned about a lot; they’re also excited. And then you want to capitalize on that and make sure that people will navigate that transition successfully.

So the book explains how you can recognize what the important transitions are in people’s lives, and how you can do your part to help them successfully make those transitions.

What are the most important qualities of a leader?

I think a leader needs to be balanced and empathetic.

How do you manage your inbox?

I aspire to be inbox zero, but it’s really more like inbox 100. I filter out irrelevant emails aggressively and unsubscribe ruthlessly. I just read and archive and file email away usually very quickly.

What song gets you pumped?

“Power Show” by Fela Kuti.

Favorite sports team?

I’m a big fan of Georgia football. Go dawgs!

Do you have any unusual skills?

I’m really good with faces. Names, not so much—but I remember faces like no other.

What’s your favorite city to visit?

London. I have a lot of family members there. And it’s nostalgic for me because I grew up going there a lot as a kid—I have a lot of great memories.

And my favorite restaurant in London is Dum Biryani.

What three items do you always have with you?

My phone, wallet and headphones—so I can break out into a dance party.

If the internet didn’t exist, what job would you want?

I’d be a musician—no doubt about it. I’ve never done anything with music, but I love music. I would play the guitar and the piano.

So then who would play me in the Calendly movie? Actually, I figured that out. John Legend would play me.

Listen to clips from Casey’s interview with Tope

Partner at OpenView

Casey leads the end-to-end strategy & programming for OpenView’s network of industry experts, advisors & corporate partners. Her role is focused on creating connections between founders & their teams and the partners, advisors, board members & events they need to reach their goals. Additionally, she manages the OpenView portfolio peer networks and hosts the #WeeklyWalk series.