Start-up Stories with Cynthia

EPISODE 3: CALENDLY

Now let's talk about Calendly. One of the biggest lessons you will learn from studying Calendly's story is how the founder was able to build a multi billion dollar startup with very little VC funding at the early stage. I think that's one of the emphases of this particular story.?

It wasn’t until after seven years of existence that Calendly was able to raise a 350 million dollars investment valued at 3 billion dollars but prior to this time, in January 2021, they had only raised 350 thousand.?

Having a billion dollar unicorn wasn’t an easy process. A lot happened to the founder - Tope Awotona. So, Tope Awotona is a Nigerian and he is the sole founder of Calendly. I think that's one of the main reasons why I'm attracted to this story, the fact that it was built by a Nigerian. Although he moved to the US? and stayed in the US for a couple of years, he was born in Nigeria. So let's learn about how Tope Awotona moved from 3 failed start-ups into a Three Billion dollar Company called Calendly.

A little background story

Tope Awotona was born in Nigeria, raised in Nigeria but left for the US where he went to High school and College. While in college, he was looking for ways to make extra money, he went into sales, selling electronics like CCTV cameras from door to door, and made a couple of bucks from it.?

After college, he got a job with IBM - this software company and had a great experience there. All of that led him into starting about three companies and failing in all of them. One was a dating site, the second was an e-commerce site based on projectors, that didn't work out well either because the projectors didn't have a lot of profit margin, although he was drop shipping.

He also tried selling grilling machines, and the profit margin was good, about hundred dollars. One of the major similarities with these three companies in terms of why they failed, is because he built these businesses out of a need to just make extra money, and make more income.?

One of the major similarities with these three companies in terms of why they failed, is because he built these businesses out of a need to just make extra money, and make more income.?

However, this was different for Calendly. While these other businesses were about how he could make extra money and not necessarily about how to solve a particular problem or meet a particular customer need. He was just seeing an opportunity and trying to jump on it, there was really no personal connection to them as much as Calendly. So that's pretty much the background.

What I want to focus on in today's article is the building process. From the moment when he realised that he needs to build Calendly, from the moment where he found the problem, how he went about his research to when he started building the company and getting his first and second round of investment which totalled about 350 thousand dollars for six years and just being profitable from their own. Those are the major areas I will want us to focus on today.

The birth of Calendly

Like I mentioned earlier, the difference between Calendly and every other start-up he had founded is that Calendly was born out of a need. At that point, he was the national account manager for IBM South East Asia and being part of the sales team or being an account manager means you're gonna be setting up meetings with different stakeholders to get them to adopt the software and onboard them etc and that will require scheduling a lot of meetings? back to back. What usually happens is that lots and lots of emails are exchanged back and forth all the time to conclude on a time that works for all the parties and he was in the middle of the mess and was just looking for a way out.?

He went online in search of an option that could help him with what he was going through as a consumer. He did find a couple of options but those did not really fit to his need, the options available were suitable to more or less brick and mortar kinds of companies but not for his own kind of Software as a Service company. The brick and mortar types are suitable for saloons or the barber's shop where you can create options for the customers to book.

For what he needed, both of them have to come to that middle point based on their individual schedules. In summary, the options he found were not suitable. So he started to look into the problem to see if there was a way out.

He started to dig deep and spent about two to three months just doing customer research. When you think about the fact that he spent three months doing customer research, I think that's quite profound because many times when we're developing our ideas, we usually just go in. If we think this is a fantastic idea, we just jump straight and start building, but it should require a lot of research and deep insight. You really need to understand what the customer needs and we're gonna see the steps he took.

The first thing he did was that he signed up for all the available options - about twenty plus platforms, he became part of the community forum. He signed up to these platforms just so he could deconstruct everything and break it down and see how it actually works, really understand how these companies were built, see the gaps and just see how the process works.

Secondly, he joined the community forum of these platforms so he can understand what the customer needs, and what they're saying about the companies or platform they're part of. Also, to just really understand the conversations in the community forums. This gave him insight into what people think about the product itself.?

And then the third thing he did was to raise support tickets to the platforms, just to really understand the customer service, how they go about pitching the products and how they're actually selling the product. So he did a lot of deep research and the whole idea was to get insight, to really understand the problem, to understand the people that have the problem and to understand the people that are currently solving the problem. I think that's really profound, and it didn't have to cost him a lot of money. Just joining the platforms, signing up and interacting gave him enough insight.

So he did a lot of deep research and the whole idea was to get insight, to really understand the problem, to understand the people that have the problem and to understand the people that are currently solving the problem.

He spent two/three months doing that and really understanding the space. He then came back after six months and said “no one else is doing this, this is a big problem”. Some of the things he saw was that customers love the product, although they want more but they really appreciate the fact that the platform is doing something about that problem. So there is that tendency for whatever he was going to build to really get into the hearts of the users and then he saw that these companies are solving bits and pieces of the whole puzzle. There was no one platform that just put everything together. So seeing that gap, he definitely saw an opportunity to build.

So now it was time to build this platform.?

There were three options, number one was to build by himself but he obviously didn't have the technical skills for that. Number two was to find a technical co-founder and that was quite difficult because a lot of software engineers didn't want to jump on a project that was still in the idea phase. Then the third option was to outsource.

Now don't forget that he still had his job going on for him. So, he reached out to a couple of software companies, most of the companies kept asking for a budget, but one company actually stood out which was in Ukraine and the company liked the idea and didn't really ask about the budget. They just shared their own thoughts regarding the idea, that actually caught his attention and they created a very awesome partnership and went on to build the fantastic product together.

Now let's talk about the whole building process, he travelled down to Ukraine and had this meeting with them, he came back and realized that this is actually really big. At a point before the meeting, it was just a fantastic idea and by the end of the meeting he realised this is gonna be big and was asking ‘am I even ready for something as massive as this’??

At a point before the meeting, it was just a fantastic idea and by the end of the meeting he realised this is gonna be big and was asking ‘am I even ready for something as massive as this’??

Remember that he still had his job going on for him. But coming back especially at that time when his mother was suffering from stage 4 cancer which was really critical, he just realized how time is really short, so you want to make the most of your time here and he said “I might as well solve this problem, I might as well build this product” because you never know when you'll leave this world.

So he went ahead and said let's do this! Although it was going to cost him a lot of money, a little over 200k dollars and that's a lot of money, especially at that time, this was around 2012/2013. Calendly is quite a young company compared to the other companies I have reviewed.?

So there you have it, over 200k required to build this. He got the money together through a lot of funny channels, credit loans, loans and other sources but you know but the major focus here should be about the fact that he decided to go all in into this particular idea and I think it’s pretty much because of how sometimes, when you look at your life and you look at everything you’ve gone through, and you see how you know everything just brings you to this particular point where you know that this is what I need to be doing with my life and that was the case for him.

He had experience with software as a service because he had worked at IBM as a national account manager, so when it comes to understanding software as a service, he actually has the experience. He also has been in sales for a very long time, so that means he knows a lot about setting up meetings and how tedious that can be, so he has got first hand customer learner experience.

The third thing was his experience in actually building startups, e-commerce startups which is actually very different, and just really seeing that fail and knowing all the gaps. So when he looked at his life? and everything he had been through, he just knew that he had to build Calendy. He had got the experience, he has that first hand customer experience, understanding the product itself which is very different from all the startups he had built in the past.

So he just felt that this was his life mission and his purpose and that was why he was willing to take all the risk to actually do this. It may have seemed very extreme, but you know it’s just knowing that everything that happened in his life brought him to that particular point where he needed to do that particular thing. And this is just in hindsight,

so never neglect your past experiences, never neglect your challenges - both success and failures. It definitely has a great impact in to how you build your business and how you create something that would last and stand the test of time.

So that was how he was able to you know generate enough funds, he had a great partnership with the software company that was going to build it for him so that he would be able to pay them as much as he had with him and just create a very good partnership that would make sure that they built this product for him.