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Sharing stories of minority entrepreneurship in the tech space


Calendly's Reginald Matthews sat down with Tanya Sam, a tech investor and Founder of the Ambition Fund and Calendly's Founder and CEO, Tope Awotona, for a candid conversation about their personal entrepreneurship journey's and the inequities that exist for underrepresented entrepreneurs in the tech space.

Learn more about Candid Conversations with Calendly and join us for a conversation in the future.

Reginald Matthews (00:05):

Morning, good morning. Good morning to everyone and thank you so much for joining us for our third conversation in our series of Candid Conversations with Calendly. I am Reginald Matthews, your host for today and I am incredibly honored and excited to be kicking off our final Candid Conversation of 2022. So hello, this is the last conversation of the year. I'm excited to say that we'll be bring you more content, more conversations, and even more talent in the new year. Today we have two incredible individuals tapping in the man, the myth, the legend himself Tope Awotona and the phenomenal and magnificent Tanya Sam. Tope And Tanya, how are you doing today?

Tanya Sam (00:44):

I am fantastic. I'm so excited to be here. I love that Calendly is doing this and I'm just revved up for a really good chat.

Tope Awotona (00:52):

Very much the same. So one, Tanya has this very infectious energy, so I'm definitely tapping into that. So I feel very, very, very excited because of that and also because of the topic that we are discussing today. It's great to be here.

Reginald Matthews (01:07):

Absolutely. I think I've said this a hundred times, but I want to say thank you to you both for being here, to being open to having this conversation while providing access, opportunity and exposure to minority entrepreneurs within the tech space. For our viewers that don't know how monumental these two are, Tanya Sam is the founder of the Ambition Fund and the Ambition Fund is focused on funding businesses founded by women and minority entrepreneurs. She is also the director of partnerships for Tech Square Labs, where she has mentored over 60 companies with women in minority founders and has helped invest in over 50 companies that have generated a total of over a hundred million in revenue. Additionally, she co-leads Ascend Atlanta, a program that supports minority female founders and co-founded Built by Women, which is a business accelerator program for women entrepreneurs. We also have Tope Awotona, founder and CEO of Calendly, the modern scheduling platform for high performing teams and individuals accelerating businesses forward.


He founded Calendly in 2013 with a vision of simplifying schedule for scheduling for everyone without the back and forth of emails. With Tope's strategic direction, the platform has grown and evolved to over 10 million users. Before we get started, I want to give the audience a few facts about the venture capitalist funding and entrepreneurial landscape that we've been in for the last two years. According to Crunchbase News, 2% of venture capitalist fund votes women only founded businesses, and those numbers are even smaller for women of color. In 2020, 2.6% of VC funding went to black and Latinx founders and of that 2.6%, just 0.6% went to black founders specifically. In 2021, 1.4% of VC funding went the black and Latinx founders. With that being said, I'm going to kick our first question off to Tanya, but I want to remind everyone to please submit your questions to the Q and A option below and we'll be sure to get to some of them at the end of the conversation. But in traditional Calendly fashion, I wanted to highlight one of our core values of finding a way. As two leaders in the tech space, I want to take a moment to hear about how you both were able to find a way during your journeys that led you to where you are today.

Tanya Sam (03:22):

Oh Reginald, thank you so much. I love this. I love the idea of this mantra being "find a way" because I feel like I've spent so much time working with incredible, incredibly successful entrepreneurs, entrepreneurs that are on their way to success. And the mantra "find a way", embodies so many of the mission statements of so many successful people. Because the thing about entrepreneurship is there are days when you'll be up and there are days when you'll be down. It's just the mindset to keep going to find a way. As I look back through my trajectory through entrepreneurship, I came from an immigrant family. My dad's African, we'll probably touch on this because we both share that lineage and it was very much medical background. Go to school, get a job, and just do that for the rest of your years. It wasn't find a way into entrepreneurship. Just be a professional, you'll make some money and you'll make the rest of the family proud.


I wasn't taught this idea of perseverance and find a way in terms of starting your own business and growth and scale. I just was like, "You are going to be a professional and I will make everybody happy." It was certainly a learned behavior for myself. When I took my first leap into entrepreneurship, I was working as an RN, working in bone marrow transplant and I wanted to start a beverage to make me smarter. I started Limitless Smart Shot literally in the med room on the night shift. I would formulate this beverage, I put everything into a bottle. I had ups and downs. I almost burned my windpipe when I was trying to do formulation. But I found a way through it. I found people who could help support me. I found people who would help me do formulation, marketing, et cetera. It's just the desire and the perseverance to get to the end goal. It is hard. Tope, you can share a little bit more about your story but it is really a one day at a time mantra and mission.

Tope Awotona (05:29):

It is indeed. Well, what an incredible story.

Tanya Sam (05:34):

Well it doesn't stop there. I sort of wanted to pause a little bit, but for me it was, and this is why I love touching on this idea of finding a way. I needed to find people who were way smarter than me and much more experienced at entrepreneurship. I found those very unlikely mentors. My greatest mentor is absolutely Paul Judge who happened to be my partner. He had done several startups beforehand and he was really great at helping me sort of shed, and I think women have this a lot, this idea of imposter syndrome of like "I don't have a tech degree, I don't have a business degree. I had never taken a business course in college at all." I was in pre-med so I didn't know how to work a spreadsheet, I didn't understand finance. He was starting a business and he was like, "You're smart, you'll figure it out." "Uh, me?" And I found the way. I taught myself what I needed to. And if I couldn't excel in that area, I didn't go back to school and do a whole PhD in computer science or business. I found people who could support the business in ways that I could. I think that is the essence of find a way. It doesn't always look like what you think it'll look like, but you continue to find a way.

Tope Awotona (06:40):

And then since then you've gone on to do a lot of amazing things.

Tanya Sam (06:45):

Well yeah, I realized very early on as I was building out my business that I needed a lot of help. I joined an accelerator program here in Atlanta. I joined Startup Checks. It was an early stage accelerator program and it taught me everything I needed to know on how to make a business plan. Then from then we decided and we sat down and we were like, "We need more of this in Atlanta." So we launched Tech Square Labs. Again, I had no idea what I was doing, but I knew we had a building and we were going to fill it. We were going to create a place where people could come and do co-working, could talk about startups. And I realized we need programs. I was like "How can we recreate some of the programs that help to make me successful?" Which is where Built By Women came in and some of the other accelerator programs that I had worked on.


And it was really culminating all these smart people around to help build and grow an ecosystem where people could build scalable technology companies. At Tech Square Labs, we talked about this. Personally, I'd mentored over 60 different companies to help them grow their businesses, help them to get capital. And it was really just constantly, it's about finding a way to find capital, finding a way to scale, finding a way to find customers, revenue, all the things that it takes to build and grow a successful business. And I still am doing it every day. Every day, every business is different, every entrepreneur that I help, every investment that I do, it's always about finding a way.

Tope Awotona (08:14):

Very, very clear from your success that you definitely know how to find a way. But you know what I also hear from a lot of people who are trying to find a way is they struggle with taking that very first step, right? Yeah. I like to say "The most difficult part of any given thing is taking that first step." Any advice on how to take that very, very first step?

Tanya Sam (08:36):

Oh my gosh, this is my favorite question because, I'm just being very personal here. I grew up, like I said, in a medical background where it was you made life or death decisions every day. I carried that through into entrepreneurship. I would get analysis paralysis in being able to make a decision. I remember reading this book once that said, "The best CEOs are really good at making fast decisions and knowing that whatever decision that they were to make on the other side of it, they'll make it happen." And that really stuck with me because I would sit there and be like, "Well what color should the bottle be or what color should this..." And it would take me months to make a decision. Done is better than perfect. You've got to just start. And if you just start it, you'll know that you can fix it, you can iterate a product, you can change, you can pivot, just start it. It doesn't matter how horrible it is, you will learn something from it, but you've got to start.

Tope Awotona (09:31):

Yes, most of us are not in life or death situations with [inaudible 00:09:36]. It's okay if it's not perfect for most of us, that's not going to jeopardize a life or put anyone at risk. I was actually at an event with Reid Hoffman, a founder of LinkedIn yesterday, and one of the things he said is I think just really good advice that is very, very similar to what you're sharing with the audience here is "You should always be in beta mode." If you are waiting till your product is 100% perfect, then you're probably leaving a lot of impact on the table.

Tanya Sam (10:07):

Absolutely. Your product will never be 100% perfect to everyone. This is the thing about customer discovery and understanding the product that you build. Every time you release a product, you will have somebody else out there going, "Well I need this feature, I need this feature." "If only it had this." And if you constantly are on that little rat race of like, "Well we are never good enough.", you won't get it to launch. Just know that you've got to launch it and learn from that.

Tope Awotona (10:34):

Yeah. Also hear people say, "If you're not embarrassed by your first product, you're not doing it right."

Tanya Sam (10:42):

Oh my gosh, I overstand this, I certainly overstand this. For sure. For sure. And it's also not an overnight thing. I love going back to your story too, because if you look back at the first initial days of Calendly, I'm sure the product was so different, it has grown so much more so that you've been able to provide so much extra service for people. But this was also not your first rodeo. You had other companies before that that you had started that didn't work out so great.

Tope Awotona (11:11):

Exactly. Exactly. Yeah, that's an excellent point. You're right. Today Calendly is, as Reggie said, serving tens of millions of people on a monthly basis. But my own journey to start in Calendly was not a very straightforward one and was definitely not an overnight success. Calendly's been in business for nine years now, but even before I started Calendly, I started four different businesses that I had to shut down. They did not go anywhere. Those four businesses combined maybe generated probably less than $10,000 in revenue. I can tell you that I invested a lot more than $10,000 into starting those businesses. But it just goes to show that the journey to doing something that allows you to create a lot of impact and something that you enjoy doing is not a straightforward one and one that if it's any kind of exciting journey, it'll take a lot of starts and stop.


Like I said, I started four different businesses, I shut them down. The first question people ask me all the time is, "How did you keep on going after you started a business, shut it down. And did that three times after that?" And the simple answer is this, "Each time I shut down a business, I was excited to start a no one because I knew all the mistakes that I made with a first one and I felt like I was that much smarter to go attack the next thing." So for me, I actually felt that I was better equipped. Because of the failure that I just went through. Now it turns out that I failed again and I felt even smarter.

Tanya Sam (12:45):

You were very smart at the end of it.

Tope Awotona (12:49):

Exactly. I felt very smart and I felt honestly that I, in some way, maybe you can call it delusional, but in some way I felt like I'd gave this knowledge that if I didn't put this knowledge to work, I would be one, I'd be cheating myself. I felt like the world needed to see what I had to offer. I'd worked for a lot of great people and learned from a lot of great people and a lot of great businesses and lots of different industries and different business models. I just felt like I'd learned so much that I needed to put all that together and create something great for the world. That was the first half of my entrepreneur journey. All the different failures. And then the Calendly story, before I started Calendly actually I had, because I'd been burned by my four failures, I knew that I wanted to do a fifth thing, but I knew that I wanted to be really, really selective with what I did.


I knew that I wasn't going to just jump into something, I was going to wait for the perfect thing in which I felt like I really understood the problem, had a great passion for the problem, and I had a unique view of how the problem should be solved and Calendly fit into all those different boxes. But on the topic of venture capital fund, which is some of the stats that Reggie shared earlier, I knew that raising a lot of institutional capital was probably not going to be a viable option for me, for many different reasons. One, I didn't have a track record as a successful entrepreneur. I came from a background with enterprise software sales, not exactly the background most people think of when they think of tech founders. Also I was based in Atlanta, not in SF or Seattle or Boston, any of the tech hub, the dominant...

Tanya Sam (14:29):

Guys nine years ago, we didn't have this vibrant and thriving ecosystem. This was just at the cusp of Tech Square Labs and Atlanta Tech Village. These were the forerunners and it wasn't the hub where money was just flowing.

Tope Awotona (14:44):

It was not. There was just a few people in Atlanta writing checks for startups and by the time they wanted to open their checkbook, they wanted to see a lot of revenue.

Tanya Sam (14:51):

A lot of revenue, yes.

Tope Awotona (14:52):

Not the luxury I had. So I knew that I had to do something different. What I ended up doing is I did a couple of things. One, I raided my 401k and just emptied all the money. My 401k took it out, I did all the things I tell you not to do. Oh by the way, my story's also similar to yours. My mom was in the medical, she was a pharmacist and my dad was an entrepreneur, he had highs, he had lows. And so my mom in some ways was sort of scarred by the ups and downs that my dad had. She discouraged me from personal risk.

Tanya Sam (15:28):

Risking it all, right?

Tope Awotona (15:31):

She wanted me to go to medical school. That's what she wanted me to do. In which I thought it's great to save lives, but I didn't think I could. I don't like the sight of blood.

Tanya Sam (15:42):

Blood and gore. You got to love blood and gore or at least really helping people. Yeah, its a trip, absolutely.

Tope Awotona (15:48):

Yeah. God bless doctors, but you don't want me to be your doctor because you don't want your doctor passing out when you..

Tanya Sam (15:55):

Definitely report your symptoms.

Tope Awotona (16:00):

Anyway, I knew that I had to fund the company myself and people ask me all the time, "Well how much money did you have that allowed you to fund this company?" And I think it goes back to another piece of advice that I have for aspiring entrepreneurs. The path to growth and success is never a linear one. Whatever it is that you're doing now, whether it's your dream job or not, it is absolutely a step that gets you to what you want to do eventually. It's important that you do that thing really well and excel at it because you're building a personal brand, people are seeing your work, those people, you may want to work with them in the future. You may want to hire them, they may be a reference for you the future.


And by the way, also doing your current thing really well allows you...That's how I funded eventually. the job I had at the time, I made sure I did it really well that I was really successful at it, which allowed me to build a small nest egg, which then later, many, many years later on, allowed me to fund this company. It is very much a journey, now can that journey be cut shorter? It can be. And there are great resources, in the form of venture capital and we'll talk about some of the work that you're doing that can help today. But it is important whatever it is that you're doing at the moment, do it well because it gets you closer to whatever your dream role.

Tanya Sam (17:16):

And I love that you share this because so often you'll have entrepreneurs and Calendly is very successful just for those that you don't know, this story is really impressive because you took your life savings, you bet it all basically, on this company and you're like, "This fifth time is going to be a charm." And I say all that to say, because oftentimes we only see the overnight success or "Okay fine, he worked for nine years, but there was all this growth leading up to it." And I think for young entrepreneurs, I really want to point this out because a lot of the magic is in the years before. Working in organizations so that you can understand how business works, understand corporate infrastructure, finding problems. You worked in business and you found this problem because you're like, listen, scheduling is a pain, but you had jobs that really needed to fix this. Trust in where you are also and trust in the journey that it takes to get there. And I love that you even just said, "You know what? I was really good at doing the job I was doing at the time and it paid the bills and I could then take that to build my company."

Tope Awotona (18:22):

Yes, yes. That's essentially what happened. And just like you, I didn't have the luxury of being able to quit my job and start this business. I had to do I both. And till today, I don't know how I did it. I had a really demanding job. I was traveling all over the country but then nights, I just slept less and I cut out things for my social life so I could dedicate as much time as I could to this and to what is now Calendly. Working nights, working weekends, extra early mornings and all the while doing my job really well in addition to funding the company because I also knew that I probably couldn't count on a lot of institutional capital to grow the business, I also really thought of ways in which I could pick a problem that was big enough to be exciting to create the impact that I wanted to do.

Tanya Sam (19:22):


Tope Awotona (19:23):

And I could find a business model and a growth strategy that would not require a lot of capital.

Tanya Sam (19:29):

I want to say this is your enterprise sales background coming in because that's the mindset. You're like, "Okay, I'm going to build some sort of software that can scale and grow that isn't going to be on the front end hugely." You didn't have a hardware product, so this is part of what that business experience that you had. Those of you that are in your jobs thinking, "Oh man, I'm working at CNN for some other person", understand that this is part of the download of information that you need for your success.

Tope Awotona (19:57):

Absolutely. Also think about if you assess what are all the advantages and disadvantages that I have? What do I know, what do I not know? And looking at all the different constraints, how can I make this Then finding a way with what I have and the resources and the knowhow that I have, how can I package all of that together to go accomplish this goal that I have and what are the resources in my network? You mentioned the point of lots of different mentors and by the way, people are really, really generous with their time if you ask them. Really thinking through who are those people in your network that you can tap on tapping to. But yeah, that's the journey. Boot strap the business and also really thought about a creative way to be able to grow the company without a lot of capital. What that meant for us is from new business model. So we make the product free. Until today, the free version of the product is very generous in terms of the capabilities it offers. What that allowed us to do is grow the company without, through a virality and word of mouth and without a lot of outside capital. It wasn't until the company was close to a hundred or a hundred million in revenue that we ended up raising institutional capital.

Tanya Sam (21:15):

Okay, are you guys listening to this? Because this is gems. He's literally telling you his blueprint and so don't gloss over. He's telling you, "Listen, we got to a hundred million dollars in revenue offering your product for free and then developed a premium paid model on top of it." But this is how people often ask, "How do I win? How do I get investors to pay attention?" Investors pay attention to revenue without question. He isn't giving you all the magic secrets in here. But when everyone's talking about as minority entrepreneurs, we are going to talk about how disparate the statistics are, but there's this really incredible thing here where revenue sort of trumps all of that. I want you to talk a little bit more about, so you knew, you were like if we are not going to get the funding in the typical ways for the reasons that you outlined, you're like, "I didn't have a big VC network. I'm in Atlanta, I didn't go to Stanford, so I might not know all the guys that typically are writing checks right now."


But you created a product that people really needed. You were solving a problem that people really were excited about. I also love problems like this because your other buddy in town, these queries are really similar, not sexy problem. You're not like, "Hey, I'm doing a cool sneaker app or whatever." It's just a pain in the butt problem that everybody needs to solve.

Tope Awotona (22:42):

Very practical, unsexy problem that millions of people around the world have.

Tanya Sam (22:49):

Millions. And that is, I think, also one of the key pieces. Millions of people, not 10,000 people, but millions of people will pay to have a little bit more ease in their scheduling life. No question about it.

Tope Awotona (23:03):

And back to your point around, well what are some of the things we did that allowed us to grow in spite of the fact that didn't have all this VC capital? I think for us, one of the things we did is because we weren't raising all the time, it actually gave us more time to focus on the operations of the business, focus on our customers and really learn their needs in a way that nobody else did. All the time we could have been spending with VCs we spent with customers, which allowed us to build a better product for them. We didn't have all this capital at the time. It allowed us to be really, really focused on what really mattered. There's a saying there that someone who's healthy and alive and they want everything, but a diamond man has one wish, just wants to live. When you have too much can actually be a curse. It allows you to sort spread yourself thin and everything sort of feels important. But when you have just a few things and you just need to get a few things done, it allows you to focus automatically, so this is some of the things that we tapped into to find a creative way to, we creatively found a way to group to grow the company.

Tanya Sam (24:16):

I want to just touch a little bit again on fundraising because I know this is an important topic for the audience out there. People that are listening in. And Reginald also talked a little bit about those crazy statistics and when we were talking about this 1% of funding that goes to minority or underrepresented founders, this is out of 100 billion dollars that was put into the VC markets. Talk a little bit about why you finally decided to go out and raise money and in hindsight when you look at, what are some of the best lessons you had about the fundraising process?

Tope Awotona (24:50):

Yeah, that's a really good question. The reason I decided to eventually raise money was, there are a few. One is our growth in and of itself was not, I guess also sort VC, institutional capital created a legitimacy in a way that our growth in and of itself probably wouldn't do. We have aspirations, we see this as a company that has a life for hundreds of years. We have many big problems that we want to solve. Doing that requires a lot of great talent from not just in Atlanta but all over the country, all over the world, eventually. We want that talent to know that we were putting a stake in the ground and we have very ambitious goals. I think institutional capital validates a business in a way that, I hate to admit it, I hate to admit it, but in a way that the company's growth in and of itself would be able to do so that's ability to drug talent.


The other is also for our customers as well. Our customers, especially for us as we were growing and expanding and moving into mid-market and enterprise companies, those companies also want to know that the company, that company's going to be an enduring concern. So those are some of the reasons. I guess maybe the third one is the networks that VCs have. They've invested in many different companies, they've built great networks along the way. They know all the right moves that company made, the companies have made at different points and their growth journey. And being able to tap into that, those are the reasons that we eventually did it. I can share some of the things that happened for us during the fundraising process, but Calendly is sort of an anomaly because by the time we decided to raise large amounts of institutional capital, we were approaching a hundred million dollars in revenue, we were profitable.


We were just being courted heavily by VCs. It was not really a process in which we were knocking on their doors, they were knocking on our doors. And eventually they made a really compelling case of about how they could help accelerate our growth. But I know some of the things we look for in that process is again, are aligned with our philosophy and the way we see the world and we want to grow. We have very specific values that we adhere to and we want to make sure that they're aligned to those and we want to make sure that they know how to work with company like us. They had a great track record of growing the companies that they work with. Those are some of the criteria that were important to us in our process. And also, I guess maybe the last part is there are people that you want to spend time with because an investor is sort of like a marriage.

Tanya Sam (27:48):

It's a marriage. It is absolutely a marriage of sorts. For sure. You want to make sure, and I even see people in the comments saying "All money isn't good money" and the timing of money is also important. Like you say, you do have a unique story, but there's something to be said for the fact that at this point people were throwing money at you because you'd built such a strong company. You were solving such a big problem in such a big market, they were coming to you. Oftentimes I think when we're really talking about funding and these funding inadequacies for people of color, et cetera, and minority entrepreneurs, this is the message that I really want people to understand. Know the business that you're building, know the target market. Look to build these big monies that can actually attract revenue and customers like this. This is the goal. It might not happen on your first, second, third, fourth, maybe it's the fifth time, but that's part of the learning process.

Tope Awotona (28:50):

I think it's important to talk about the two different ways you can go about building but about building your business. Certainly the Calendly story did a little bit of both. Boot strapped the business initially, raised a small siege round and then later on raise a large round of institutional capital. There are many businesses that don't need institutional capital, right? It's really important to think about, I guess maybe the simple heuristic that I sort share with people is if you're confident that you have a business that can generate billions of dollars of revenue someday, maybe it makes sense for you to pursue an institutional capital. But my belief is there's a lot of success between zero and billions. If you end up building a business that generates, let's even call it six figures. That's a...

Tanya Sam (29:49):

That's amazing.

Tope Awotona (29:50):

A nice outcome you guys.

Tanya Sam (29:52):

And I love that we can start to have these conversations right now because once upon a time it was like, "Ugh, that was a cute little business." I'm like, "Six figures is cute?" Understand that there's so much power in just starting your business, getting revenue, getting customers and just building. Have the vision so that it can be as big as possible. But you've got to start somewhere. And I think there's different types of capital that are available and make sense for very different types of business. There's a lot of buzz around right now about startups and private equity or venture capital. Know your business first and know where it makes sense to start pitching and asking for money.

Tope Awotona (30:35):

Love that, but that crowd who is dead set on building this billion dollar businesses. Can you tell us a little bit more about what you think the biggest opportunities that we have to help bridge the gap between minority entrepreneurs and non-minority entrepreneurs when it comes to funding?

Tanya Sam (30:50):

Oh, I love this. I think one of the biggest things right now is educating the early stage entrepreneur. From my perspective, when I'm working with minority entrepreneurs, early stage entrepreneurs, a lot of them haven't understood, and I see myself in them, what it is to build a business. Understanding just a pitch deck, your target market, all these pieces that will inform the rest of your business, especially as you go out to raise money. It's almost like there's this native language and you're not meeting with these investors or angel investors as philanthropy. They're really about, "I need you to dive into your entire business, lift up all the skirts so that I know that if I give you money, I'm going to get a return on my money." They're not out there to necessarily catch you or make you say the wrong thing.


They just want to know that they're going to get a return on their investment. That means knowing every detail about your business, your competitors, what your customers look like, how you're going to make money in five years, 10 years, what's your roadmap? Every question has to be answered. And I think sometimes it's just about practice, watching other people build businesses, know what it means, understanding your books from day one. I think this is the big biggest piece. It's about education. Education on how to get to that point. Then on top of that it is also again about being able to, like you said, one of your biggest things was I needed the network. I needed the network. When I got to the point where I was comfortable taking my business on the road, being able to pitch and be able to raise money that I could have access to people who could actually make things happen.


Networking is a very long game. It's a marathon, it's a marathon. It's not just, "Hey, here's a cold email, I've got a great business, you better invest in it or else." It's like, "Hey, how's it going? I'm working on this." I bet you still remember people that were like, "Hey Tope, remember that first business that you pitched me? It didn't work out." But on number five, they were in because they knew you. Sometimes I think, especially with the ambition fund, it's about how can I connect you to the right people? How can we start having more of those conversations about what raising capital looks like? How can we do more business education to help get you into some of the fortune 1000 companies that are in town? For pilots, just to get customers. All of these little things I think really contribute to helping move the needle and make success for minority or early stage founders.

Tope Awotona (33:26):

Hope you guys are taking notes out there.

Tanya Sam (33:28):

I hope so. Listen, I'm going to throw back a question for you because we both stare these roots. You're from Nigeria, I'm from Ghana as well, and I'm starting to do more and more business back in Ghana, checking out their startup and technology scene. I want to ask you your thoughts on how it has been having to mentor and as a successful Nigerian American here that's built companies, what are your thoughts on expanding to the diaspora and reaching more of the tech scene in Africa?

Tope Awotona (34:02):

Yeah, I have a lot of thoughts. One thought being, "Man, I feel like the entire nation of Nigeria and the Nigerian diaspora is just rooting for me and Calendly in a way that is just incredibly inspiring and motivating." I guess I want to start off by just thinking the Nigerian community for their just incredible support.

Tanya Sam (34:27):

Isn't that something though?

Tope Awotona (34:29):

Oh my god, it is.

Tanya Sam (34:30):

The community that you build around this. I just want to say there again, because this is, Nigeria loves and loves to support, but even for black people, we want to see people win. They're rooting for black people to win, whether it's through funds and other things. So I love to hear you say that and appreciate it because I really think people of color might, we're rooting for everybody to win and it's a really special thing, so that's awesome.

Tope Awotona (34:57):

It is a special thing and I feel it every single day. Listen, it makes me want to do my best work every single day. It really does. Africa and Nigeria are both really real exciting. There's increasing amounts of VC dollars that's going to Africa. I think last year alone, I think it was 6 billion dollars. I had a small part in that. Going back to how we support entrepreneurs in those countries, I've invested in a few smalls, my funds myself, nothing material, but just want to be in some small way, support what they're doing and also mentored a few entrepreneurs. What I want to do next that I haven't done, and this actually maybe is a segue into what I think is the biggest opportunity to support those entrepreneurs, is I want to spend more time in Nigeria myself. I would love to go to all the different tech clubs in Nigeria, meet the founders of different companies in Nigeria and just learn what it's like to be building at a very, very exciting time. This is just a very exciting moment in which tech is going to become dominant in Nigeria. Not just in Nigeria, but Africa in general, there's just a lot of strong STEM talent in that continent that is going to really help to solve a lot of the problems that are plaguing the continent as well. Export some of that here as well. But the reason I have not been more active or spend more time in Nigeria is candidly, Nigeria worries me.


Rampant corruption, a lot of crime, the lack of infrastructure. I actually think the best way we can help entrepreneurs who are building amazing companies in Africa right now is to help them demand more from their government. I think that we can find a way. For example, there's a entrepreneur that I mentor in which do a lot of business in Africa and all of a sudden one day, some government, we won't name the government, but they just shut down the business.Because they were doing something new and they weren't sort of greasing the wheels and all of a sudden the business got shut down. The private sector alone can't fix all those problems. Long story short, I think there's an opportunity to help them demand more from their government. Exactly how to do that, I don't know, but I know that that would be just a great unlock. I don't know if you have any thoughts.

Tanya Sam (37:31):

I love that you say this because this is a very candid conversation. That is one of the biggest problems probably in detractors, I think going on in Africa right now. There's a lot of corruption and you say this example of, "Hey, this person started a business and it was shut down by the government" and we kind of in the US have this perception of "Can you imagine?" But this is a really common practice, so it's difficult. I appreciate, and in case you don't know, Tope is also dropping gems here. If someone can start that company, I feel like we would all invest. He's giving away free ideas here. That would be a big, massive life changing solution for government and leadership across Africa and the diaspora. But I agree, and I have spent some time back and forth in Ghana for the past, I think 18 months.


I've done a couple small investments as well. Most of them have been in the FinTech space, which I think is helping to make some significant change there as well because it's attaching people to way more opportunities just able to spend money, save money, make money outside of the country. I think there's something like you say about how we can involve government a little bit more in supporting this, How we can bring in more investments from the outside and mentorship. I liken it to a little bit about when we talked about Atlanta. 10, 15 years ago, this wasn't a tech scene. The tech scene was out in the valley, maybe Boston, where we'd seen a lot of successful entrepreneurs make a lot of money, funnel that money into creating more and more companies. Then that butterfly effect happens over and over and over again. I'm hoping to see more of that in Africa in the diaspora where entrepreneurs like yourself who have been successful, are now turning around, they're mentoring more folks, they're putting more money into it, and then we'll start to see a slow butterfly effect. This is all obviously tempered by the fact that there is a lot of government involvement in there. I think it's a meandering road, but one that I'm hopeful for,

Tope Awotona (39:44):

I am as well. We can definitely only go up from here and it's very exciting times.

Tanya Sam (39:52):

Oh, I love it. I love it. Well keep me peeled. Maybe we need to do a trip home, an investor trip back to Ghana and Nigeria, do some education sessions there.

Reginald Matthews (40:04):

As long as I can join on that trip.

Tanya Sam (40:12):

I think we said everyone's like, "Bring me with you."

Reginald Matthews (40:15):

Absolutely. I'm sorry to interrupt this riveting conversation, but we have to get some audience questions in. The first question is from Tim and he says, "Do you think that it's feasible to launch a product even if someone has done it already in the past?"

Tanya Sam (40:31):


Tope Awotona (40:33):

Is this for you? I want this question.

Tanya Sam (40:37):

All right. Absolutely.

Tope Awotona (40:42):

There are actually very few winner ticks. All markets out there, there are few products out, there are few services in which there's just one dominant provider of it. They're greater. I always use the example of restaurants, think about how many restaurants there are out there. Long story short, it is very possible, especially if the addressable market is large. The question I would encourage you to think about is "What makes you better than this company? I, as a consumer or a buyer of your product, why should I choose this? Your company and your product over the competition? Is it because you, do I get better outcomes from your product? Is it because you're cheaper? Is it because your service is better?" It's just really good to think about what makes you differentiated from your competition. But yes, competition is good.

Tanya Sam (41:40):

Competition is good. Great answer. I love that.

Reginald Matthews (41:43):

We have another question from Laurel, and I actually want to kick this one to Tanya first. We had a brief conversation about this earlier. A big struggle is overcoming the need to be perfect all the time, but to be restrictive, if anything. Have either of you experienced this and how do you get over it?

Tanya Sam (42:01):

Well, I feel like I've talked about this a lot because technology was not my background. I had a lot of imposter syndrome. I feel like women in particular, we like to do things right. We like to be perfect. So for me, again, it is honestly taking stock of the little voices in your head that are going to tell you, "You can't do this, you're not good enough. And literally you've just got to kick them away because it's just the negative track in your brain that's trying to protect you from failure. It's trying to protect you from not doing the right thing. But there's a bigger piece of you that you need to tap into to just know that you got this and it seems like this high level woo woo Instagram empowerment chat, but it's real. You've got this. And even Tope will tell you what you're building today, what you're trying to launch it won't look like that one year from now or even six years from now. Just know that you have the skill set to improve, to iterate, to pivot and make it better. And you got this.


The one other thing I will say is make sure you have a team of people around you that are your support people that you can go through. I say this all the time, I have a mastermind group of four women and we meet monthly. It is really about solutions and pouring into. It's not your family that's just going to tell you everything's right, but they're people that are going to tell you on the days that it's like... Have you ever heard that expression? "Entrepreneurship. It's killing it. It, I'm killing it. It's killing me."? Because every day is totally different. You need people that are going to be like "Keep going, get up off the ropes." Those are the things that I think really have helped me to keep focus on the worst of the lowest days of entrepreneurship in whatever you're building.

Reginald Matthews (43:59):

We have... Oh, go ahead Tope.

Tope Awotona (44:01):

No, she's dropped a lot of nuggets. But, Sorry, go ahead Reggie.

Reginald Matthews (44:05):

I'm sorry. Y'all also going to say there was one very, very specific question actually directed to Tanya and Mia asked, "What startup groups would you recommend for women to join or look into?

Tanya Sam (44:15):

What startup groups? Yes. Oh great. Here's the beautiful thing about Covid. Before Covid, I think that we were all geographically based and tied to whatever city you were in. If you were in Idaho, there probably weren't a lot of startup groups around, but now you can do everything virtually. Take the time if you really want to do it, you're going to have to make your list and investigate what it is you're looking for. Number one, I would say do the research and understand what type of business you want to build. If it's a hospitality business, a consumer product, good. Find an accelerator group that suits that. If you just want some basic learning and education parts, honestly go to your city's small business. They have tons of grants and money that are out there and it's just sitting there unclaimed, literally, it's not picking up your lottery ticket.


From the small business in your town to tech stars, there's tech stars that are popping up in every state pretty much right now, Y Combinators, but just do a little bit of research. Even Google has a lot of entrepreneurship programs. My program is not in session right now, but it will come back late 2023 where we'll do another accelerator program. There are so many out there and a lot of them come with small investment grants that is free money. Some of them don't even ask for equity. I feel like, I wish I had a list that I could give you guys, but just honestly Google University accelerator programs for women, accelerator programs for men accelerator programs for people that are starting SaaS based business. They're out there.

Reginald Matthews (45:57):

Tope, angel investors aren't investing as early anymore. Any tips for founders seeking investment at the earliest stage?

Tope Awotona (46:07):

I don't feel like I have great advice for that, but I can give some general advice and maybe similar to sort what worked out for me at Calendly is at the end of the day, what investors care about is traction, right? Do you have product market fit? Have you built something in such a way that it is solving a critical problem for people? And do you have a way of getting it to people in a cost efficient way? And then can you eventually generate profit from it and can you expand this? And so when people aren't investing, and I would take the time I have to go figuring out those things. Who are my customers? What can I do to improve my product?


What can I do to better target my product to the right customers so that you have a compelling story to talk. At the end of the day, every investor is motivated by greed, right? they don't make money sitting on their money. They want to invest in something that's going to grow. I would try to find a way to tell that compelling story. Sometimes when you have all those things, you're just not really good at the story storytelling piece. There are indeed programs out there that help with that as well.

Tanya Sam (47:31):

And I think that's a great point because investors are motivated by greed. This is not philanthropy. I love talking about how we can help more diverse founders, because I think at the end of the day, it actually benefits the perspectives in the world and benefits investors as well. This is a two-way street, but understanding that that's what investors are looking for and spending the time really digging into your business to build that will always prove to be the right answer for sure.

Reginald Matthews (48:05):

Well, I'm officially raising the flag to say that we are at the end of time, but also that we probably need to do a part two of this at some point.

Tanya Sam (48:13):

I feel like we could go on and on.

Reginald Matthews (48:13):

On. Absolutely. We need to do a part two. We need to bring this back at some point in time. But thank you Tope and Tanya, for this incredible conversation today. Our focus and our goal for this series is to educate, uncover challenges across underrepresented communities and ideally drive change. I want to thank you for bringing your knowledge and insight to yet another important topic today. Thank you everyone for attending and we can look forward to hosting you in 2023 for more Candid Conversations with Calendly.

Tanya Sam (48:44):

Thank you so much. It was incredible.

Tope Awotona (48:46):

Tanya, thank you so much.

Tanya Sam (48:48):

Yes. I really had a good time. Thank you so much. Listen, you give us time back with Calendly, so I am not just a host today. I am a staunch user. I appreciate it and I just appreciate you as an entrepreneur in Atlanta that has done so much for the community. Thank you for hosting conversations like this. It's really important.

Tope Awotona (49:11):

Absolutely. Although I want to give all the credit to Reggie and Lucia.

Tanya Sam (49:15):

Yes. This whole team. So thank you all. Thank you so much and continue to just do this great work that you're doing.

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