At Terrain, we can’t get enough of win-win business models.
Which is why we’re so excited to share the entrepreneurial success story behind a product that maximizes wins for entrepreneurs, online professionals, and freelancers all around.
Dotcal, the only design-first scheduling platform, transforms your mundane, run-of-the-mill booking page into a creative, personalized, and brandable experience – ensuring that your first impressions are always on point.
To know more about the story and vision behind Dotcal, we recently sat down with Rylan Blowers, Head of Product and Co-founder at Dotcal. We chatted about his experiences with entrepreneurship, his advice for those just starting out, and got the latest scoop on some exciting new developments at Dotcal.

Why Dotcal isn’t just a scheduling app:
We’ve already gushed about how much Team Terrain loves Dotcal.
But if you need a quick refresher on why you need to hop onto it ASAP, here’s how Dotcal is different from other booking tools, in Rylan’s own words:
“So obviously, the most in-your-face thing, (and I’d say our core value proposition) is that everything we do is design-first. We’re building booking pages to be personalizable, brandable – ones that allow you to represent either yourself or your company in a way that hasn’t been possible before. The end goal is to have everything be completely customizable, and allow you to make the best first impression possible.”

But that’s not all.
Rylan went on to tell us that Dotcal is trying to transform the way we think about scheduling as a whole. The platform doesn’t only want to make scheduling “a delightful experience for both parties involved.” They also want to use it as a method to “democratize time and make scheduling headaches just a thing of the past entirely.”
Shared booking pages, one of Dotcal’s latest features, are the perfect example of how Dotcal implements this. With just one click, you can now sync your calendar with another person’s – eliminating the back and forth of scheduling entirely.
The possibilities for using this feature are endless, starting from personal catch-up calls with loved ones, to onboarding new clients, or holding team meetings. Here’s what Rylan had to say about the new feature:
“There are personal booking pages, which is what you traditionally know and what you use to book [general] meetings. And then there are shared booking pages…which allow people to just create a use case and a page for all these crazy different opportunities in their lives that they need to schedule meetings for.”
And if you’re worried about using booking links for a top-tier client?
That’s where Dotlinks come in: “Dotlinks instantly pull in your availabilities and just present them in a plain text format (as if you went and spent five minutes going back and forth and building it up). This is for the people that sometimes feel a power imbalance when they’re using these links, even though they’re objectively a valuable tool.”

How Dotcal’s Business Model Was Created By “Working Backwards”
While talking about the value of schedulers, Rylan emphasized that at Dotcal, they wanted to take advantage of the “beautiful business models” that scheduling platforms have and the power of the “marketing flywheel effect.”
“…Every one of your customers is also marketing for you, even your free ones, and everyone that they use it with has to interact with your software. So if you’re gonna make really delightful software, you might as well have something where people are going to sell it on your behalf.
…And you know the flywheel effect is super, super powerful…there’s an immense amount of SEO power and SEO juice that’s out there to be captured by all these sites that list your links, in backlinks, so if you know how to harness that, it’s also incredibly powerful.”
Dotcal’s genesis was, what Rylan calls “a little bit formulaic.” There was no “quintessential entrepreneurial, aha moment of, we need to start this thing.”
Instead, he and his co-founders David Matthews and John Donner, started by putting together a team, assembled from all over the world, and decided they wanted to start a tech company.
But not just any tech company. According to Rylan,
“[We wanted to start a company] in a space where there’s room for improvement because…we wanted to build beautiful software in spaces where we think the bar isn’t that high. [So, software that] prioritizes aesthetics, in a space that can benefit from something like that.”
And after six months of having bi-weekly meetings, the team realized that they kept coming back to the idea of scheduling platforms…and realized that there was room for an upgrade in the space.
“We all lived and died by our scheduling links, because they just provide so much value, especially when you’re busy. In my last company, I would have died, if I didn’t have a button to schedule 10 meetings a day like I was having. It’s an incredibly valuable tool.”
Dotcal’s story is a great example of how working backwards in the early stages of building a business can often lead to a clearer vision of one’s business model. The platform stands as an inspiration to budding entrepreneurs who know they want to start their own business but aren’t sure of what they should be creating yet.
Challenges…and achievements
In only six months, with only a small team, Dotcal has been able to reach almost complete feature parity with companies that have been around for a decade or more. But success hasn’t come without its fair share of challenges.
“So our biggest challenge has been geopolitical risk. Our engineering team is in Ukraine. And they’re amazing. They’re just like, the most incredible engineers and designers, and hardworking people ever…And as we’re getting ready to launch with the whole founding team, everything happened with Ukraine. And it was just an incredibly emotional experience for the team. And we felt kind of helpless, especially since we couldn’t get our engineers out.
Our team, [though] they didn’t skip a beat. [And we told them], you need to take whatever time you need, make sure you’re safe. But to be honest, it’s a testament to their hard work and just their character and willpower. And despite it being, one of the most emotionally draining periods of my life…I learned a lot through the process and it just cemented how much I admire all our team members that are out there.”
Rylan’s Entrepreneurial Story (and tips for those just starting out)
While talking about entrepreneurship, Rylan told us that he always knew that he wanted to start his own business:
“I knew since probably the age of eight that my end goal was going to be to run my own thing, which I feel very grateful for — most people don’t have that kind of clarity and I felt like I did. I grew up on a farm. And, you know, we had extra eggs. And boom, there was [my first] side hustle. I’d take my little wagon and go up our dirt road (our nearest neighbor was like a mile away) and trudge up the hill. And then every job I got in high school, I figured out a way to kind of monetize it on the side and figure out a way to make it more efficient. And so I think, in my mind, it became very clear that this was the end destination, I feel very grateful that at 26, I’ve already been able to fully go for it.”
While it’s clear that he loves his job, he agrees that it can also be challenging:
“Everyone talks about how you have to wear a lot of hats [as an entrepreneur]. But every day is truly hectic. The number of context switches I have within a day would be in the dozens. I’m coding one second to [then] getting on a demo, doing a blog post [and then] going back to coding. It’s just…truly mind-melting”
His favourite part about his job, on the other hand, is the very act of creation itself:
“I think the idea of having a vision, especially when it comes to building a product…and then bring[ing] it into fruition and all the considerations that have to go into that [is my favorite part]. And then seeing the outcome, [where] you’ve created real value and made people’s lives easier.”
Rylan also had some solid advice for people who’re starting out as entrepreneurs and are looking to chart their own pathways:
“I’d say the best thing you can do is just approach every day with curiosity. When you’re looking for problems to solve, if you’re curious about everything, and constantly thinking…all the time I’m thinking about what’s a better way to do this. And just giving yourself a sample use case. Like, how would I approach this if I were to solve this issue? I think like, that’s the first step.
At Terrain, we delight in looking at the world sideways, and since curiosity is one of our core values, we couldn’t agree with Rylan more.
(If you’d like to start using Terrain to feed your curiosity, and scale your business sign up for a $1 trial today!)
Rylan also addressed the fears that many beginners have with regard to competition:
“The other thing I would suggest is that don’t be afraid of competition or taking a leap of faith. I think one thing that I thought was that, if someone’s already doing it, there’s no opportunity for me to do it. Because someone else already had the idea. In reality, there are almost 8 billion people on this planet, there are going to be 1000 people trying to do the niche idea you just came up with. What matters is obviously execution. Ideas are useless. There’s just so much opportunity for improvement, even if there is competition, like the bar is generally pretty low. So don’t be crippled by competition.
Rylan goes on to say: “I think when we were starting Dotcal, if we took a look and said, “oh, there are other people already doing this, it’s a crowded space.” We never would have gotten off the ground. But because we kind of approached it, as I mentioned, from a formulaic [point of view] it made sense…. You’re not Elon Musk. There are definitely other people doing everything you want to do. So just be the best at what you do.”
If you’d like to start using Dotcal to make the perfect first impression, head over to this link to get started!
(First booking pages are always free, but Terrain members get 50% off Dotcal Pro when they use the code TERRAIN50!)