I know firsthand that building companies is hard—really hard—and I love talking to other folks who’ve done it. I had a chance to speak with three other founders at Zapier’s first-ever user conference,
ZapConnect: Tope Awotona, founder of Calendly; Mathilde Collin, founder of Front; and Vlad Magdalin, founder of Webflow. Each of them faced a lot of adversity in building their companies, and I was excited to learn about some of the unexpected challenges that they overcame.
One of the main reasons I love these conversations is that, in sharing stories, we’re able to offer insights to folks who are just starting their entrepreneurial journeys. So with that, here are the five things that stood out to me most from our chat, and I hope they help you as you build and grow your business.
If you’re interested in learning even more about these founders’ journeys, you can watch a recording of the conversation here.
1. Care about the problem you’re solving
This is business 101: if you don’t care about the problem you’re solving, you’re not going to get very far. But what came through in this conversation is that it almost goes beyond caring. It needs to be kind of an obsession.
Tope shared Calendly’s origin story: “[I was] trying to arrange these meetings with what felt like twenty people across three different companies. And it must have taken forty, fifty emails over a week or two,” he said. “I was hoping I could stop thinking about the problem, but the more I tried to stop thinking about it, the more obsessed I became. And I wasn’t happy until I raided my 401(k) to start what is now Calendly.”
It’s that kind of obsession that will keep you going when things don’t go exactly as planned—which they never do.
Vlad framed this obsession as an “irrational confidence” combined with “a sense of purpose behind the work that you do.” He knew the idea behind Webflow—to give non-coders a way to create—was valuable. “I needed to make this real,” he said, “and I didn’t feel that about anything else.”
2. Take care of yourself
The problem with being obsessed with something is that it’s really easy to go down a rabbit hole and rarely emerge. And that’s something that all three founders I spoke to learned the hard way.
Mathilde worked herself so hard that she was physically incapable of continuing: “I worked a ton, and it was unsustainable,” she said. “The main reason why I felt like Front could fail was because I would fail as a human being—I would stop being able to work just because I would push the limits of what my body could do.”
It’s possible to get to this point in any job, but Tope pointed out why it’s such a risk for founders: “If you create a business and if you do it well enough, it will become your primary identity.” And like Mathilde, Tope’s work became his life, and he ended up putting all his energy into the company. “I wish I would have invested more in those other things like my personal relationships, my hobbies, little things that just give me the energy and the fuel to really embark on this life-long journey.”
Having external help with this can be huge. I have a coach myself, and Vlad pointed out that there are founder support groups and other entrepreneur communities you can join. I’m lucky to have two other co-founders, but if you’re doing it on your own, you may need to go out of your way to avoid the isolation.
Mathilde started taking care of herself through things like meditation, not having work apps on her phone, and taking more time off. And now she tries to lead by example so that her employees feel empowered to take care of themselves too. She put it plainly: “The best thing we can do for the company is to take care of ourselves.”
I couldn’t agree more. I regularly try to encourage the folks on my team to take care of themselves, and I know the best way to do that is to take care of myself. I take time off and am vocal about doing so. I unplugged during my parental leave. Things like that.
3. Recognize your impostor syndrome
Mathilde has been pretty open about the early struggles she faced when starting Front. And in our conversation, she pointed to one realization that helped her through them: “you can’t really fake it.”
Almost every founder is going to run into impostor syndrome, especially given the skepticism we all face. This skepticism comes at us from all sides. Tope’s ex-employer actually thought Tope was so desperate to leave his job that he decided to solve a problem that didn’t exist. But honestly, the hardest skeptic to overcome is ourselves.
Mathilde told us the story of how a partner at YCombinator, a startup accelerator, told her that Front was a great idea. Her impostor syndrome ran so deep that she was sure he must have been talking about another company. “That was my level of confidence in what we were making,” she said. It was only after meeting other founders and CEOs who said they experience those same feelings every day that she was able to start getting over what she refers to as her “paranoia.”
Vlad agreed. He talked about how everyone thinks they’re the only company that’s not nailing it and that everyone else is doing things better: “Other companies look at you and secretly think the same thing, but nobody’s talking to each other and giving each other permission to just be human,” he said.
So find other people to give you that permission—and then give it to yourself.
4. You need luck, but you can’t rely on it
Every founder relies on luck. Meeting the right person at the right time, having the right idea at the right time, or just being born into some sort of privilege that led you to where you are. But an equally important element is discipline.
“I prefer talking about the things that are in my control,” Mathilde said. And discipline is what Mathilde could control: managing her time well, laser focusing on certain metrics, saying no when she needed to.
This resonates with me. Zapier has always been an all-remote company, and remote work requires so much discipline. You have to make sure that you’re documenting your work, you have to commit to writing things down. And a lot of humans are just a little lazy about that stuff. We like being able to informally tap someone on the shoulder; we like the casualness of it. But in a remote workplace, you have to commit to that discipline, otherwise it doesn’t work. And really, as any company gets to a certain size, you have to do this anyway. So starting early—and with yourself—will pay dividends down the line.
5. Think of the journey as a brisk walk
Early in the conversation with these three, I referred to starting a business as a marathon, not a sprint. But later on, Vlad offered a different way to look at it, giving us a great update on a classic metaphor:
A marathon you have to train forever for. You run like a maniac, and then you basically pass out and throw up and have to go in an ice bath afterwards.
I think of it more like a brisk walk or a hike that you can go on every day with friends. You’re challenging yourself, getting more fit, incrementally improving while enjoying the journey and pushing yourself.
I love that. Now go take your brisk walk.