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Tope Awotona

lines on the record: 107
first: 2024-01-08
most recent: 2024-01-08
sittings or episodes: 1
sources: podcast

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“So, I think we are all lucky, but I think what amplifies that luck and what makes one successful is hard work, it's skill, it's resilience, it's an appetite for risk taken. So that's my view. I think it's a combination of both, but I think when you add those four things, it just takes a whole different level.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Oh, that's a great question. So, I think everybody's lucky, right? I think the very fact that I didn't get hit by a bus today, that's luck, right? And we're same thing for you. The fact that that didn't happen to you, that's luck. And, you know, I look at the family I was born into. I think your family really determines your ceiling in life and your floor as well, like how high or low both of those things are. And I had no say in the family that I was born into, so I feel incredibly lucky there. I picked the right industry, you know, one that's grown, like crazy. So those things are definitely luck. But I think”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Absolutely not. I'm very excited about what we're doing. And I feel like we're just getting started. There's a lot to do. And so that's not remotely on my radar.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Do and I spend a lot of my time thinking about that. 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 too often not only are meetings difficult to schedule, people sometimes forget to show up when they show up. They're not prepared. There's no clear memorialization of the key decisions that are made and action items that are open. Those are the things that we're looking to fix. And there's a lot there. And that will keep us very, very busy for five years.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“I used to. I found is that when you spend a lot of time with your customers, I think you find out that there are a lot of things that they want to do that need to be done that maybe those companies don't have the appetite for doing.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“A little bit of both. So start to generate revenue, and it definitely extends the runway, and I forget exactly how much. Additional time it gave us, but we ended up raising an additional $200,000 in early 2015, as Cushion is an insurance policy of sorts. We ended up not needing it. But we did”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Absolutely was the plan to eventually begin to acquire larger customers. But some of that was already happening, right? So we were getting pockets of department in those big businesses using our product.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Access and users. And so some portion of the existing user base was disappointed that they had now had to pay for a product that was 100% free. Really, what the premium plan did was he basically still had a free product, but we just limited what you could do in the free plan. And so you had to upgrade to the premium plan to get, let's call it 60% of the features you used to be able to get for free before.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Yes, and so that became priority number one raised the $350,000. Because honestly, I didn't enjoy the funder raising experience. And I wanted to make sure that I never really had to do that again. And so I prioritized generating revenue. By August 2014, we'd turned on billing and introduced a premium plan. And so we start generating revenue in August of 2014.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Right, so it was just me. I was the only employee, and then Rails were it. And so that ended up giving me, I want to say something like nine months of runway.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, so I was ambivalent about raising money, to be honest with you, because I felt like I started the business in the most difficult way possible, really, you know, putting everything I had, risking everything I had to start the business. And so in some ways it felt like a step backwards to have to cede some of the ownership. But once I met David, that changed in the sense that I felt like I was going to have a I was going to be working with a successful entrepreneur himself and not just a money man. I felt like I could learn a lot from him. And so the ambivalence I had went away once I met him.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“So we have one or two meetings and he follows up with a term sheet and says I love what you're doing. I think that this can be big. I'd love to invest.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, so I started going to different events. I started connecting with people in the startup community. And then I ended up signing up for a membership at a place in Atlanta called the Atlanta Tech Village, which is a cool working space specifically for tech startups. And it's while I'm connecting with different investors that the owner of the Atlantic Village catches wind off calendly. David Cummins is his name and he thinks it's really interesting because he at the time he was actually using a competitive product. And so he knew firsthand that this was a big problem and he was impressed with what we'd done. And so we get connected.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“In the southeast. So, a few people in Atlanta, a few people in the southeast. I had, you know. Guy from a pretty big firm. Not only did he, so I mean, I'll tell you, I had a very... I thought was a very condescending kind of experience. So at the time, I was actually in Kiev, right? So I'd flunk to Kiev to work with Railsware and I stayed up till 2 a.m. to meet with this person. And then he stands me up, right? So, just a lot of experiences like that were just, you know, it's one thing to not invest, but it's another thing to kind of treat people like that. How much is that just the arrogance of somebody who thinks you're an important VC versus race? I know who knows, but I mean, I do know that many other entrepreneurs who didn't have as much, who hadn't made as much progress. Had more offers than I did.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, so I think, first of all, I think it is difficult for pre-revenue businesses in general to raise money, especially in the Southeast, right? Because I think that the farther you are away from the coast, the more investors value revenue. Whereas when you're on the coast, I think they care more about growth. So I think that process for anybody is challenging. But I'm sure race plays some aspect in it, but it's not really There's probably more to it than that.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“A quote of yours I read, and I want to read it to you. I'm curious to ask you more about it because you described the process of trying to raise money. You said everyone said no. Meanwhile, I watched other people who fit a different profile get money thrown at them for shitty ideas. Those VCs were ignorant and short sighted. The only thing I could attribute it to was that I was black. Can you walk me through your experience trying to raise money?”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Funded in 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. Was able to get them to work on credit.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“No, they didn't think so. They thought it was a solved problem. I remember when I was leaguing and I told my boss I was leaving. He's like, you're leaving for that He felt like he'd filled me that I, you know, like he felt like I was get desperate and I, you know, and I'm pursuing scheduling. That's a solved problem. Like, nobody needs that. But yeah, it was not definitely not obvious. I didn't quite know how I was going to fund it. But the decision to me was clear. And so I began to put together a pitch deck and start going to different events trying to meet investors.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“I don't know that I actually felt comfortable, but I knew that a decision had to be made because I seen the growth of Calonley, I realized that, one, this thing was growing in spite of the fact that I was just doing it part-time. And two, I owned 100% of this thing I was growing. And so to me, the choice was very obvious.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Exactly. So the first 300 to 500 signups really came heavily from K through 12. But after that initial wave of K through twelve, it spread to all kinds of different industries, it spread to people in all kinds of different roles. It was salespeople, it was recruiters, it was freelancers, it was consultants I just began to spread like a wild”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“So I hadn't left that. So this is, you know, this is my side hull. So I was still, you know, I was meeting my obligation to the company. I actually had a really good year that year. And so I felt like so long as I was, you know, it was not interfering with my job. It didn't really, I didn't feel like I needed to disclose it. And so I have this dilemma in which the business is growing in the sense that people signing up for it and every time every day the signups are growing because of the virality of the product and because people are getting good value from using the product. But I had no I didn't have the money to turn it into a revenue generating business.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“That had to become the idea. So I was faced with this dilemma. So keep in mind, I'm still working my full-time job this whole time.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“You can set up Quick Hooks, but it's within an online product, you have to find a way to restrict the features that they're not paying. There's some technical complexity there, some work that needs to be done to kind of turn the features off and on based on their trial status, their payment status, collecting the payments. Initially, I mean, just to give you an idea, initially, that was maybe two, three months of work for two engineers to work on that.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Correct because I ran out of, I had just enough money to build the scheduling capabilities. But not enough money to get around to enforce the billing. So no way to capture revenue from potential users.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Exactly But because I ran out of money, we couldn't build the billing features. And so by default, the product became 100% free.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, so I'm glad you raised that because I neglected to mention that. So, because I ran out of money, my idea, the business model going into it was to have a 14-day trial so you could use the product for free, no credit card, no feature restrictions for free for 14 days. And at the end of those 14 days, you would have to upgrade with a credit card.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“In Kentucky And so they come to me and they say they want to sign up 80 teachers, and I just 80 teachers, which at the time was a lot of people.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Exactly. They say, I schedule a lot of meetings. That was easy. I would love to use this to simplify my meetings. And so the K-312 school start adopting it. And then they turn around and start using it for parent-teacher conferences. So the use case goes from we're using it to do onboarding calls to these schools start doing parent teacher conferences with it. And then a few weeks in a school comes to us and says, This is the best thing that's ever happened to us. We've been struggling with parent teacher conferences. We struggle with how the administrative burden of setting them up, the participation rates. We want to roll this out to all of our teachers.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“And so Railsware was like, hey, let's show you this product that we're built in, right? So they show them calently. And at the time, Calently is not quite, it's not quite ready to be in a public beta, but what ends up happening is they love the product. And so somebody from their customer success team signs up for the product and starts using it to schedule onboarding calls with their customers, which those customers happen to be K through 12 schools. So customer success person from this company in San Francisco starts scheduling onboarding calls with the K through 12 schools. So, the cat's out of the back at that point”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, so I got help along the way through Railsware actually. So a few things happened. As Railsware was building the product, they got connected to another potential client, a software company in San Francisco that's gone on and done really well to a multi-100 million dollar business now. And that company was looking to engage them to do some work for them.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, so I poured myself into the business, into the product. And so, you know, it was a very, very, very difficult thing for me, very, very difficult thing for me. But Calendly became a huge distraction from that. And I just, I worked. Like a dog, just so I didn't have to think about that.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Not really, so I kind of downplayed it to her, so I told her that I was, you know, she knew about the previous businesses and she supported my... Different business ideas, but she wanted me to. She wanted me to prioritize my day job, but she thought it Thought I was doing really good with my job and that I shouldn't lose, she didn't want me to lose focus of that. So in some ways I downplayed what I'd done to her, but I'd really committed a few hundred thousand dollars to it.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Man, you need to be able to integrate your calendar, be able to specify your availability in all these different ways. You need to be able to guard your availability. And so I thought the user experience and design just needed to be front and center. It just needed to be appealing functionally and also aesthetically. We had to get really fancy with how we detected time zones to make it really, really accurate without the user having to, you know, intervene at all. So there are a lot of technical, small technical details that really made a difference in the user experience that we had to figure out.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, so a few things. So, before I ever met Railsware, I'd actually come up with my own requirements document. Okay. Which again, something I didn't do with the previous businesses. So I had, I created my own detailed list of requirements and detailed flows I needed to happen that needed to be built. And also my own sequence of how the work needed to be done.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“So, this is 2013. You put all your money into this product to be built for this company RailsWare. Most of that money is going to them. What did you tell them you said okay, I want this to be like a calendar that somebody can just say, hey, here's a link to my calendar, you pick a time when you want to meet me, and that calendar would be integrated with whatever they used, whether it was Google or Microsoft or whatever.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Not at all. It sounds crazy to say that now, and it could have been really, really, really bad, and it would have set me back many, many years if it didn't work out. But not at all. Here's why. I've learned a lot from my previous failures. This felt like, you know, as crazy as it sounds, I felt like I had a call in to do this for a number of reasons. I felt like I spent all my life in sales and I think I really understood. I felt like I knew a lot about meetings and meeting etiquette and what works, what doesn't work. I felt like I actually unlike the e-commerce businesses that I tried to start I actually knew a lot about software businesses and I felt like I, because I spent so much time researching the space I felt like I knew exactly what needed to be built to build a great business. So it sounds crazy, but I wasn't scared.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“A very high interest rate, so cobbled together my 401K and my savings and then some debt and maxed out all my credit cards. Put it all in On this idea that at the time it didn't even have a name.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Yep. I had to use every single dollar my savings account. I had to borrow a little bit on top of that. I ended up borrowing a little bit from Linden Club.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Had most of it, but it required doing a lot of things to tell you not to do. So I had to empty every single dollar my 401k.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Correct. Now's the time to do it, nothing's guaranteed. You can try to wait for the perfect moment, the perfect idea, the perfect development sequence, or you can start with this place and start it with what you can do and expand from there.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Yes. So before I hired him, I actually flew over to Kiev to meet with them and we spent two days really brainstorming on the idea. They challenged me in a lot of different ways. I learned a lot from them. But I actually came back to the States initially not thinking that I was going to do the idea. I actually came back from the meeting thinking, man, this is... Much bigger than I thought. Maybe it's too much to do. But I ended up changing my mind. A few things happened. Around the same time, I found out that my mom's cancer was terminal. And I think it gave me a sense of carpe diem a little bit and just really realizing that who knows how much time we all have, you know, like here's my mom and she's dying She make the same decision if she was faced with the same decision knowing her lifespan, what decision would she make?”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Absolutely. And it's interesting you say that because the other thing that happened is as a scrappy entrepreneur, one of the things I try 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.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“No, I didn't make them sign Not because ultimately what I believed was, and it's still what I believe today is I think the key to success is the execution of it, not so much just the idea because, you know, a number of other people before me that had the idea, but I was thinking of executing it a very different way. And I thought my own... Guess maybe I was full of myself. I thought my own unique perspective on what needed to be done would be good enough to protect the idea.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Exactly And so I kept looking, and so I didn't roll those people out, but I ended up finding a company in Ukraine. And from the first interaction that we had, their initial response to me was on how much money do you have to put into this. To this idea, their first response back was we think this is a great opportunity to. As a matter of fact, here are three ideas that we have. And so I knew. Knew that I wanted to pay attention to them”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Exactly. So there are lots of companies out there that really help whether they're large corporations or entrepreneurs bring their products to life. And so what I ended up doing was I started talking to a few companies in the States. There was one in Atlanta. There was one in Charlotte. There was one in San Francisco. And inevitably, the very first question they would ask me was, what's your budget? I get that it's an important question, but I just felt like all they really cared about was...”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“Exactly. And also, you know, they're also probably well paid at what they do. So, you know, kind of risking all of that to...”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“So, what happens is this a lot of people have, you know, everyone has an idea for an app they want to build. And so if you're a talented engineer, you get a lot of terrible pitches every single day. And so most engineers that are entrepreneurial, they would rather pursue their own ideas or if they're going to take their risks, they'd rather like bet on themselves and kind of go after it. as easy as it sounds that you know just because you have an idea it doesn't mean that you can really attract get engineers to get excited about it”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“And so I decide that this needs to happen fast, so it's not really something I can code myself. And so I start going to meetups to see if I can meet other technical co-founders, but that didn't prove to be successful. And so my third option became, let me see if I can hire a firm to build an initial product.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“It takes me six months. So with the other businesses that I started, I basically had made a decision to start the business and I look for all the evidence to support a decision I'd already made. With this, I led with an open mind. So I was just as happy to not do it as I would have been to do it. So I just really let the fact kind of guide me. And I was hoping at the end of my exploration, I would come back and say this is just like the other business ideas that I've had. Someone's already done it and they're doing it really well. Go do something else. But within the six months I couldn't sleep until I thought about.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT
“And what I learned was that in spite of the fact that I thought there were gaps in what they did, their customers loved what they did, in spite of the fact that their customers wanted a lot more. thought what they did was incredibly valuable. And so that was interesting to me. And it told me that if at a minimum you do as much as what they're doing, there's a decent business to be had out there. And then I thought if you took it to a whole different level and you really lowered the barrier of entry and really democratized it and make it made it simpler for the more casual schedulers, I thought there was an even bigger opportunity. And I just knew that this had to be done.”
2024-01-08 · How I Built This with Guy Raz · Calendly: Tope Awotona (2020) · IDENTIFIED FROM THE TRANSCRIPT