Lisa
Tope! It’s so good to see you. I am so glad that you agreed to Keynote Startup Runway for our 10th showcase. Welcome.
Tope Awotona
Yes. Thanks for having me. I’m just, I guess I would like to say that I’m also honored that you invited me, so I, it means a lot.
Lisa
Well, I’m a huge fan of you and your journey as an entrepreneur and founder. It’s incredibly impressive. I love that long-form interview that NPR recently did with you, but for our focus right here for the startup runway, our audiences, the finalists and finalists are pre-seed first earliest revenue entrepreneurs. They have a lot of doubt and they’re being told, but the big, bad world, all the right things to do, and you can’t do all the right things. Thanks for being willing to focus on how you’ve learned what the right things are. I’d love to start with your first launch of Calendly. You launched it and did you feel that it was the right product?
Tope Awotona
I did. Let me share more why I do so, you referenced the NPR interview. The fact that it’s, by the time I started a Calendly, I started many businesses before that. Now they all went sideways, but I learned a lot from them. One of the things I really learned from those other businesses was that it’s not enough to want to start a business. Like that’s not a strong enough reason to start a business, a strong reason to start a business that you’re passionate about a problem, and that you want to, and that you’re dedicated, to devoting a significant part of your life, really, to solving that problem. Like are you that passionate about that problem? And for me, I was that passionate about education. The reason was, one, it was a problem that I struggled with myself, right? It’s actually what led me to count that I wasn’t looking, I’d had all those failures. I was taking a sabbatical from starting businesses. At the time I decided that I wasn’t going to start a business and start a business. I would, when we started businesses, there was a problem that I felt like I had a unique vantage point on solving. I feel that to say that when I started counting, I spent six months looking for all the reasons not to do it. In spending those six months and finding all the reasons not to do it, what I ended up learning was that it just gave me a really clear idea of exactly what the gaps were in the market and what this product, which I eventually got wasn’t even commonly needed to do that, to be successful. For all those reasons, I had a lot of confidence that I had, that the product that was building the temple was really gonna solve a huge problem for people. That was one part leading up to the decision once we launched the product, that was validated very quickly, what happened was, because of the viral polity, because of the viral nature of the product, the initial users, which again, we haven’t really advertised in any way. We haven’t really promoted the product in any way they caught wind of the product, right? So, the initial users were actually users from, the dev shop that built Calendly for us, or there were also, customers are the same dev shop and they actually caught wind of the part of it for it was getting to be, publicly available, generally available. And so they started using it. As they used it, they introduced other people to it, and those people kept, and then the cycle kind of repeating itself. Some of the signals that I saw very early on was that a lot of, in spite of everything that was so optimal, everyone marketing the product was very, the feature set was very basic initially. Also, people had a lot of really, they had a lot of feedback about the things they would love to see the product do, but in spite of all those things, people were finding other products that were getting value out of it and they continue to use it. To me, it became very clear, and also seeing the versatility of the product, right? So it just started in a specific industry, but very quickly, it spread to many industries and sped too many people in all the different roles. Combination of just watching the patterns around how they spread, and all the things that, and the fact that it was growing in spite of everything that like on the surface was suboptimal that really gave me the confidence that we had a great product.
Lisa
I’m a huge believer in founders. Who’ve experienced the pain personally really believe that creates a vision for the product that you cannot earn in any other way. There are a lot of people who say, Oh, you’d have to actually have experience of the pain, just have passion for the problem. What do you think about that based on your own journey?
Tope Awotona
Yeah, I think there are different types of entrepreneurs out there. Right. I think you have to be true. You have to be treated like the type of entrepreneur you are. I’m the kind of entrepreneur that I know commonly, wasn’t a novel idea, right. There were scheduling products on the market, but I think County did take an existing idea that was on the market and made it better. Right. So, built in a way in which it appealed to a broader audience. Maybe, anyway, so I think kind of, we got all those things, right. Kelly did not create a new category of Dell itself. It just really latched on to an existing category. I feel very confident that I’m that kind of entrepreneur, like, I, my experiences have taught me that I know how to supply things that have been validated by other people and they’ll just make them better. Like, I feel really confident in that, in terms of creating a brand new category, I, I think that’s something that’s things there, but it hasn’t really been proven yet. I think people really just have to ask themselves, like, am I, what kind of entrepreneur and do I have a track record of creating or do I feel like I have the Hastings to create a new category, solve a problem in a completely different way than even want to solve it? Or am I really the person who takes something that’s validated and makes it much bigger. Right. I think both can work. I think you just have to be true to yourself and I, and sorry, I’ll say is that I do think that instincts are incredibly important, in guiding you towards,
Lisa
That another way of saying bet on yourself?
Tope Awotona
Yes. Don’t bet on yourself just because you believe in yourself. I think you should ask yourself, like, what truly ask yourself, what earns me, what burns me the right to solve this problem? Like, what do I know? Do I truly know something that most people don’t?
Lisa
Now, one of the things that I hear several times a day as Valor gets pitched is I have a brilliant idea and I’ve earned the right to have a brilliant perspective, but I need an investor to allow me the opportunity by funding me so that I can go on that journey. What’s your experience with that? Do you think that’s a good way to go? I know you’d had a different path, but you may have reconsidered and thought no, that would have been a better way to go. How do you feel about that situation?
Tope Awotona
So the situation being in, how much do you prove the idea and then bringing in an investor to scale it? Or do you, I guess there’s a question, about bringing investors at scale, the idea or raising money or not.
Lisa
Yeah. I would say that one of the most typical pitches you get as an early-stage investor, like Valor is I have a brilliant idea and they do, generally speaking, there are a lot of brilliant ideas out there. I have an incredible experience and generally, they have a pretty good experience. I can’t afford to start it. So I’m raising money to try it.
Tope Awotona
Yeah. So, it’s easier, it’s easy for me to say this because I was able to prove my idea, and then get fun and to grow the idea and scale the idea. I subscribed to that approach. The reason I do is just, for a couple of reasons, I think there are so many new investors getting pitched the time, right? And so they need alike they need a filter to really figure out like, where are they gonna really put their dollars to work? And if you just look at it from the vantage point of the investor, they want to invest in the opportunities to have the most offside, while at the same time being de-risk as much as possible. Right. Any kind of idea has all kinds of, has all, To do it just makes you that much more attractive in the eyes of an investor. That’s one thing. The other thing that’s true is that, even if you’re going to raise money, the more progress you’ve made and the more progress you’ve made, the stronger position you’re in when you’re raising money, right. You get many better-controlled terms than economic terms. You can, you can be really selective about who you choose to partner with. If you, like, if you take the first that fundraising is inevitable, which I think is there, like, a lot of people take, I think even if you take that approach and it’s still not, I think, is a founder as the best interest to delay that, as much as possible to a point in which they’ve had something, which they’ve proven. I just, because I, I just think it was suddenly a much stronger position, for so many different reasons.
Lisa
Yeah. For early Calendly for the MVP, I heard that you wrote the requirements yourself, you said you are an outsource provider. How did you learn how to write proper requirements?
Tope Awotona
Well, it’s funny you say that cause actually six months ago or so, I forgot about that requirements document, and that company shared it with me and it was great enlightenment. It was like, it was really touching to see it, but they’re really, I guess the interesting thing was at the time, I thought I’d have written through this very thorough requirements document, and maybe had 10% of the information that you would probably need it maybe held 10% of the requirements that ended up getting fleshed out over the next, six months as we built the product. I don’t think that to answer your question. I didn’t, I did not. I didn’t have any kind of professional experience developing a requirements document, but what I did have was I had a lot of professional experience selling large enterprise software applications to large companies and what we would do. Like, take my time that, back when I worked at EMC or IBM, you’re selling these, like you’re selling these deals that are maybe a million dollars in software, but almost inevitably, they almost required as much professional to implement the product and deploy it to the company. Most of our short as a part of selling enterprise software, right. I also learned a lot about, I learned a lot about how you can capture requirements from businesses to really understand how to solve their problem and also translate those requirements in a post-sale to make sure they actually got what they want. That’s really where I learned, in a lot of ways how to write requirements. The requirements are like maybe they didn’t meet all the professional standards, but I did have your experience has been a part of many larger software projects in my professional career.
Lisa
What’s been the most fun for you about building Calendly?
Tope Awotona
There’s not enough time to list all of them. I think I’ll tell you some of the most exciting lessons, some of the most exciting ones are just being, it’s not often you get to build something that, to be a part of building something that solves your own scratches, your own edge, right? So like being able to shape and influence, a product that ultimately I get to also benefit from is incredibly exciting. That’s one thing the other part is, the impact that the product has had on our users, but, fast forward to now hundreds of millions of people have experienced account leads. It’s very difficult for me actually to wear a countless t-shirt and not, and I guess started nasty, like if we, like, what my affiliation is with every time I wear the shirt, the conversation happens and it’s getting to the point where there are fewer people, who’ve never experienced the calendar in some way. Like on a, I think the last time I saw you, I was running to get the donut sham. One of the other times I was at that donut shop. I had a shirt on, and this guy who was accountable because they started asking you questions. Just to see the impact of, what we’ve built and how it’s, helping people, acquire customers, retain customers, grow their businesses, be successful in their role. That is huge, I mean, I’m just honored to be a part of that. That’s two, the third part is just really the Calendly story. It’s commonly a story itself and how it resonates with a lot of underrepresented founders, right? So are the suits, as County is growing as more of that, as the countless stories been told, what I found is that a lot of underrepresented founders just reach out to me and say, your story has been really inspiring and it’s really made entrepreneurship attainable to me. That part, I didn’t anticipate that when I started counseling, but that’s actually been one of them, that’s one of the most exciting things that’s really happened is to see how their work is just impacting the work that I do in the work that we do is impacting so many people in so many different and swimming positive ways. And that’s incredibly motivated.
Lisa
Yeah, I know in the beginning, like every software founder, I’m sure you had not only the viral growth, but some users shared negative feedback because, they had a vision too, and they really, some of your best users actually give negative feedback. How did you learn how to manage the disconnect between baby product back when it was very new and negative feedback, which is just a part of the journey?
Tope Awotona
Yeah. A couple of different ways. One is, I think, understanding, this is just like simple statistics, but really making sure that you actually have a representative sample, right. So on any given day, right. Anybody can feel a certain way about a product or a certain feature. The question you have to ask yourself is that, what percentage of your audience truly feels this way? Is there something, and is it something that a lot of people feel is one and also of all the different things you can do to make the product better for them? What is the relative priority of this, right? Not just like, is it true, or is it important to solve or not, but what is your rank? Like, how can you get us? It’s always helpful to get a sense of where we are and how we stack in terms of, all the things you can do to move the needle for your users. I think the third part is really having a clear sense of who you want to serve. Right. So, if an astronaut is trying to use Calendly to schedule a known time to go to the space shuttle, like, and they complain about this one feature, I clearly knew that’s not our target aud ience. It also allows me to think about it. Now I’ve got somebody who’s fans, five who in a given week spends five, schedules, five or more external meetings. Well, that’s our target audience. We’re going to pay closer attention to that person’s feedback than we would somebody who’s using to do something out of the scope that we were hoping to accomplish. Those are some of the things that have really helped. I guess the final piece is that the most successful companies, and I think when I look at the best things that have happened to Calendly and let’s calm this growth, they’ve 100% come from listening to our users. Like there’s no doubt about that. County, it was a much, it’s a successful company today and, how’s, the chance to continue to be successful because we do a really good job of listening to our users. It starts, it definitely starts and ends with, customer empathy and really understanding what your customers are looking to do.
Lisa
I’m going to key off that word, empathy that you used. I think you definitely have customer empathy. You’ve been really gracious about some of my feedback over the years, too. So your entire team an awesome product. My God. So here’s the thing though. A lot of times, a strong visionary CEO, like you, that really has a vision, has trouble hiring a great team around them. I think you’ve had the success of hiring a great team around you. What would you share with other founders about some of the lessons learned? How do you think about picking great people?
Tope Awotona
Yeah, I’ve learned a lot. I think one of the first things I can learn is it’s the most important thing we simply play. The reason is, if you’re gonna serve your users, well, your customers really want, and you can’t do it all by yourself. One and two. You’re not always going to be in the room when important decisions about how to serve those customers are being made. Right. The way you really make sure that not only argument can do, but I say that to say, like, it’s not important that you just make good decisions, your entire company needs to make really good decisions. For those reasons, it’s the most important thing. I think the second part that I’ve learned is it really starts again with being really clear about what you want out of the role, right. Is, if you can’t answer how you measure that person’s performance in 90 days, you’re not ready to hire if you’re not if you can’t answer to a candidate very clearly what the vision of the company is and what the goals are that accompany the goals of the company is trying to drive in the next six, 12 months. You’re probably not ready to hire. Hiring well really starts with you having a clear idea of what you want and what success looks like. If you can’t answer that in a very objective way, you’re probably not ready to hire. 90% of the, like them, when I look back at the good hires that we’ve made in the bad hires that we’ve made over the eaters, it always starts with this misalignment at the beginning of the journey, right. It’s just like everyone, like everyone has different expectations of the role, and really making sure that it, that nice alignment doesn’t even exist. It greatly improves the chances of success. The second part is, once you have a clear idea of what you want in the role, what are the values that you want to be as a company? What are the values that want people to demonstrate when they’re in the company? What are the goals you want them to hit working backward from that to really, to design a process that helps you, understand all of those things and standardize that process? Well, the number of steps, they’re involved from interview to offer to the questions you ask, and the two who participate in it, the more you can standardize that, and really have a clear process and a clear understanding of what good looks like, what bad looks like, what ugly looks like and how you’re going to make a decision. I found those things to be truly helpful in making good hires. The last part is just, you have to treat it like a product, right? every single hire that you make, every single hire, and make every single time you let somebody go. It was good to take, do a retro and say, what did we get right here? What did we get wrong? so that you can continue to improve your process. I guess the final thing, sorry, I’ll say is that never forget that it’s a two-way street when you’re interviewing people, you’re interviewing them because you want that, you want to bring them to the company, but they’re also looking to learn about you and the best people just have so many options. So, it’s important to make sure that you create a process that actually makes people want to join your company. Right. And be there, indefinitely.
Lisa
How have you learned to talk to yourself differently potentially through this journey from MVP to a highly successful enterprise software business? do you find that you’ve honed in on a certain type of relationship with yourself? Has your relationship with yourself changed at all through this journey?
Tope Awotona
Oh, yeah. That’s a really good question. My relationship with myself has definitely changed. I think you learn different things about yourself, right? I think in this journey to go from nothing to, tens of millions of revenue and also, scaling the company and bringing so many people on board, you learn so many things, you end up learning things about yourself. You didn’t know, some of those things for me, where, I guess, like, we don’t need to get into that, but, long story short, like this process has been very enlightening for me. I’ve learned a lot of things about myself, like areas in which I need to grow and develop. Also, you also come out of it with a, around, what, like you, these are like, these are certain things that have certain strengths that you have, and you should never underestimate those trends. Right? So even as you’re bringing all kinds of people who are much smarter than you, who are more, who are subject matter experts in the different areas that you bring on board, you’re still having a very important role to play. You still have, you still have some strengths that you want to make sure that you’re still bringing to the table, even as you begin to, easily, even as you begin to defer to others on the team. Those are some of the things that I’ve found is, like really doubling down on, truly understanding what my strengths are and doubling down on them and, figuring out where those weaknesses are and working on those.
Lisa
Yeah. That constant self-discovery is one of the most interesting parts. I think of the founder’s journey. I know for a lot of our founders, if not all, and not at all times, but not only do we want to be those resources, but we encourage them to find out where those resources are for them to give them those mirrors and reflections so that they can continue to grow as they lead their company. Because the company is following that growth path in so many ways, intellectually, emotionally on a team, spirit level leadership level. It’s an amazing thing. I think companies are like a Juul, but the light that sets them off as the founder’s fire and got to keep it shining. So it’s interesting. It’s like, it’s a, quite a crucible and I think you’re one of those amazing lights in Atlanta. I really am glad to know you.
Tope Awotona
Thank you.
Lisa
What have I not asked that founders asked you all the time and we could capture here and share with the finalists, just kind of the final question. What do you think that you wish founders, or you wish you had known when you embarked on this incredible adventure?
Tope Awotona
Wow. Lots of different means I didn’t want to, I’ll just rattle a few that kind of come to mind. I think it’s really one if I would’ve thought about the company’s growth mornings in stages and phases, right. Really figuring out like, what is this current stage that we’re in? and what are the things that are important to be good at it at this stage to be bad at this stage? And one of the important investments to make, or I think to put in place for the next stage, that’s one getting the right advisors, right. I wish I would have invested more into it. I was lucky to be at the Atlanta tech village where there were a lot of other entrepreneurs around them. So, it created an informal environment for me to learn from any different peers. As I, as we move out of the tech ledge, I wanted to show it to be more deliberate about seeking out other advisors. That’s one of the things I wish I would’ve done differently, going back to hire, and then people, I mean, could not emphasize the importance of that. I wish. For us, about three, four years, three years ago, or so we defined our values. Right. So, I wish I would have done that sooner. Right. Because he just became, again, I ended up becoming, really, important to make decisions around who you want to add to the team. Also, how do you promote people? How do you reward people, how you give that feedback? Just being really clear about your, again, really good at planning, right? So again, seven years in, at something that we’ve learned to be really good at, but every company can get really good at that base. Like so from your strategy, from your strategic plan, like, what do you want to do, what’s your strategy and what’s your operational plan? What do you want to actually do in this fiscal year or whatever period in which you’re planning, but just getting really good at that? The vision, the mission, the strategy, and of that, and then the planning, those things I wish I would’ve done, I wish I would have learned more about those that even much earlier on. I wish I would have surrounded myself with people who were doing that. Some of those things are some of the things that really come to mind. I guess the final thing is that, just, one of the values that we have at a colony starts with humans, so that means treating ourselves, being tolerant of others. It also means understanding that any decision you make, whether it’s a product, whether it’s about a feature and how it works, or whether you build it or not build it or a pricing change, whatever it may be, or even, a policy around how you, support policy or like the different support channels you offer, whether you offer email chat and who’s eligible for it or not, all those decisions impact the human being on the other. Right. It’s always really good to make sure that we’re not blind to the consequences of our decisions and how they impact actual human beings. Just really putting that front and center, and decisions, right? So your customers, your employees, your team, it’s important to never lose sight of the human aspect.
Lisa
Awesome. Well thank you so much for sharing your wisdom and your time today, we’ll start in a front way. It means a lot. I really appreciate it.
Lisa
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