Insight
Awotona: Scheduling software requires a great recipient UX for mass adoption
“If this would gain mass adoption, you really needed to build for both For all participants, you needed to make it a great experience for every for all the users of the product, whether they were your own registered users or the people who were receiving invita…”
Insight
Awotona: Entrepreneurial engineers prefer building their own ideas over joining yours
“Most engineers that are entrepreneurial, they would rather pursue their own ideas, or if they're going to take their risk, they're rather, you know, like bet on themselves and kind of go after it.”
Assertion Not checkable as stated
Awotona emptied his 401(k) and maxed out credit cards to fund Calendly
“So cobbled together my four one K and my savings and then and then some debt and maxed out all my credit cards and put it all in on on this on this idea that at the time didn't even have a name.”
Insight
Awotona: Coastal VCs prioritize growth, while non-coastal VCs value revenue
“I think that the farther you are away from the coast, the more they the more investors value revenue. Whereas when you're on the coast, I think they care more about growth.”
Disclosure
Awotona: Calendly has raised only $550,000 in total outside venture capital
“On the balance sheet, just the half the 550,000 dollars. That's all the outside money that's gone into the business.”
Disclosure
Awotona: Selling Calendly to an acquirer like Salesforce is not an option
“Absolutely not. I'm very excited about what we're doing, and I feel like we're just getting started, and there's a lot to do, and so that's not remotely on my radar.”
Opinion
Awotona: Being an immigrant's child hindered navigating the corporate world early
“I think being the child of immigrants, I think maybe hurt my understanding of how to be successful in the business world in America. And so I didn't do some of the things that my peers were doing, like internships, I didn't do those things.”
Disclosure
Awotona: Dev shop Railsware rejected equity-only compensation for building Calendly's MVP
“One of the things I tried to propose was, hey, why don't I just give you a cut of the equity and you can work for free but even they weren't willing to take that risk.”
Assertion Not checkable as stated
Awotona: Calendly launched completely free because he ran out of money
“Because I ran out of money, we couldn't build the billing features. And so by default, the product became a hundred percent free.”
Assertion Not checkable as stated
Awotona: Calendly's first 300 to 500 signups heavily came from K-12 educators
“The first, you know, 300 to 500 signups really came heavily from K through 12, but after that initial wave of K through 12, it spread to all kinds of different industries, it spread to people in all kinds of different roles. It was salespeople, it was recruite…”
Disclosure
Awotona convinced Calendly's external development agency to work on credit
“Funded it myself and ran out of money. And then I convinced Railsware to work for, not work for free, but to work with understanding that when I raised money, I would pay them back. So I was able to get them to work on credit.”
Assertion Not checkable as stated
Awotona: Calendly reached approximately 15,000 users by September 2014
“Maybe about 15,000 at the time.”
Assertion Not checkable as stated
Awotona: Calendly currently has about nine million monthly active users
“About nine million people use the product on a monthly basis.”
Disclosure
Awotona: Calendly's roadmap aims to automate the entire meeting lifecycle
“Our overall vision is to take the work out of meetings, right? So we really think about our mission as not just removing the back and forth of scheduling, but how can we really automate the entire meeting experience, right? So, you know, too often, not only ar…”
Insight
Awotona: Door-to-door sales is a predictable game of volume and conversion
“It ultimately gave me the understanding that there's a hit rate, right? So if you knock on X amount of doors, you'll ultimately make X amount of dollars. So to me, it was a very predictable thing, and in between, there's a lot of rejection.”
Assertion Not checkable as stated
Awotona: Small software startups grew monthly what IBM grew annually
“So at the time, you know, IBM was probably growing double digits every single year. And some of the businesses that I was looking at where, you know, probably going, growing double digits every month.”
Assertion Not checkable as stated
Awotona: Perceptive Software took eight years and multiple pivots to find PMF
“It took them eight years to really get to product market fit as we call it today. And the idea pivoted many, many, many different times.”
Disclosure
Awotona invested roughly $20,000 of his savings to launch ProjectorSpot.com
“I put in probably something like, I would say about 20,000 dollars or so. I don't remember all the details, but I would say most of it probably went to the website development.”
Insight
Awotona: E-commerce projector hardware was a loss leader for accessory profits
“Well, one, because electronics in general are just very commoditized, and there are many, many other merchants out there, and so, most of the competitors were actually not making their money On the projectors, like it was a loss leader for them. What they were…”
Assertion Not checkable as stated
Awotona: Calendly's $350,000 seed round provided approximately nine months of runway
“That's right. So it was just me. I was the only employee, and then, you know, Railsware, and so that ended up giving me, I want to say something like nine months of runway.”
Assertion Supported
Awotona: Calendly employed slightly fewer than 200 people by September 2020
“A little shy of 200.”
Tope Awotona