Awaken Newsletter: Navigating Startups and Challenges: A Conversation with Webflow’s Bryant Chou

On November 10th, I had the honor of chatting with Bryant Chou. Bryant is the co-founder of Webflow, one of the leading website-building platforms in the world with a valuation of $4 billion. Within startup-land, Webflow is especially notable for being mostly bootstrapped, waiting five years before raising an additional round after their seed round in 2014.

In our conversation, we touched on a variety of topics ranging from being Asian American to working at startups vs. big tech. 

Note: Quotes were lightly edited for brevity and clarity.

EARLY CAREER

I started our conversation by asking Bryant if he had any entrepreneurial endeavors before his first official company. While he never directly started a business, Bryant did display early signs of his scrappiness.

My mom gave me twenty dollars a week for all of my lunches and whatever discretionary income. So, of course I spent most of it on food, but that essentially meant that I had nothing really left over. But I also really wanted to be a normal high school student and go to prom and go to dances and stuff like that. So I made money in high school by entering Counter-Strike tournaments. I would earn, I don’t know, a few hundred bucks in these local LAN parties. And that’s how I paid for dances. So I always kind of adapted and tried to apply myself in different ways, with whatever skill sets I had.

He continued on to talk about his motivation for getting into startups:

To be honest, I don’t know if I would have done startups if I was at Facebook or Google. You know, I didn’t land those jobs coming out of school. I wasn’t smart enough. Didn’t pass those interviews… I think because I was at a mid-tier tech company, it kind of gave me more hunger to do something on my own. I wanted a change and believed software startups were the future. I took the plunge in 2011, driven by the belief that startups would be significant, 

However, he also cautioned about rushing into startups: 

You need to think about the things that really need to be true in order to be a founder and do it successfully. One of those things is working in a space that you really want to affect and make a difference in. You just want to make sure that you’re working on something that’s worthy of 16 hour days, you know?

BRYANT’S ROLE AT WEBFLOW

Although Bryant is perhaps best known as being the co-founder and CTO of Webflow, I saw that Bryant had recently shifted his focus away from technology to growth and marketing for Webflow, so I asked him about that:

Because we were bootstrapped, we never really invested in growth and marketing. So what started as an impatient maneuver on my end, like, ‘hey, I think we need to start doing these things’ turned into, ‘hey, this is actually something that is ROI positive.’ Who would have thunk? I suppose even though I’m an engineer and builder and product person at heart, I’m also a company builder in that sense. So I’ve–for example, started our marketing, started sales, started data, started security, so all these things are just things that are just like, ‘hey, we need to do these things. Let’s figure out how to do it.’ And I think that’s something that most entrepreneurs are going to have to do. I don’t think you’d necessarily have an option to not do it.

Coincidentally, I had talked to the new CTO of Webflow, Allan, a few months prior. Alan was super nice and very sharp–a great backfill for Bryant.

NAVIGATING ASIAN IDENTITY

As the Asian Hustle Network, I naturally had to ask Bryant about how he felt being Asian qualified his experience as a founder, he started out by acknowledging the position of Asian men:

It’s a well-known fact that Asian men in Western societies have a different bar to hurdle than other people. One of the reasons why I was so keen to help produce the 38 in the Garden movie with Jeremy Lin is because he articulated this so well. Have you seen that documentary? 

I had not, in fact, seen the documentary. Oops. I watched it after the interview on his recommendation and it was very, very good. Please give it a watch! Bryant continued:

It’s my one and only film and probably the last one that I’ll ever be involved in. I’m totally okay with this because I believe this cause is important. Part of the reason why I agreed to chat with you is because we obviously have a chip on our shoulder. We are seen differently in society. I’ve dealt with it in various ways myself. I’ve taken a colorblind approach to business interactions and never thought about my race or ethnicity in certain environments. I think that’s ultimately what you have to do. As Asian people in Western society, you’re supposed to be heads down, let your actions speak for themselves. I still very much have that approach. Who knows if it’s the most optimal thing to do.

Despite his colorblind approach, Bryant was clearly very cognizant of the fact that people perceive Asians differently, and had a suggestion for our readers:

To just walk amongst people of the same race and they speak your language, I think that’s like a worthy thing to do and to dive into. I identify as Taiwanese, at least as much as I identify as an American. When I go there, I literally feel different. I feel like I’m one of the same, like I’m among my people, I’m not viewed as a minority, I’m just viewed as a normal person. I think every Asian-American should have that sensation at some point in their life that they feel like they’re seen as someone just like everyone else, and the only place where I felt that has been Taiwan.

I knew Bryant grew up in the Bay where there were a lot of Asians, so I asked him if he felt the same sensation in those areas, he suggested:

The broader construct of society that we live in is still the US, which is still 85% non-Asian. I think Asian Americans make up about 12% of the population, maybe even less. I don’t think it’s so much about not being in the majority. It’s more about the sensation that you get that you are biologically or ethnically more similar to the people that you’re walking around with in Asia.

NAVIGATING ENTREPRENEURIAL CHALLENGES

Moving onto the next topic, I asked Bryant about his emotional experience as I had heard a lot of founders talk about how difficult this aspect of running a startup was:

I thought it would be harder technically than it would be emotionally. But I would say the social emotional components of building a company are 100 times harder than the technology itself.

I followed up by asking if there were any specific experiences that stood out to him:

They’ll come up in different forms. In 2020, there were a lot of social justice issues that made running a company very challenging. Ultimately, when you’re at a company, you need to be hyper-rational. You’re faced with a conundrum between being a good steward of the company’s mission and vision and maybe what people inside your company believe, and sometimes those things clash.

It was clear that this level of situation took an emotional toll on Bryant, so I asked him how he copes with it and prevents it from seeping into his personal life:

You compartmentalize most of it. It helps to have a supporting spouse and partner. It’s great to have kids that can distract you from this.

ADVICE FOR YOUNG PROFESSIONALS

Adding on his comments about entrepreneurial pain, Bryant offered:

I think like if you’re in your 20s, I would actually be chasing that kind of pain. It’s the best time to chase pain and suffering. If it means that will lead to a certain level of intellectual expansion, social emotional awareness. There’s no better time to find the limits of what you’re capable of than when you’ve graduated, when you’ve got a whole life in front of you. Like, it’s time to see what you’re made of. So I’d be a huge proponent of young folks going to startups that are hectic and crazy, working in environments where they can learn, dedicating time and energy to perfecting a craft. Those are things that you don’t learn in school. And those are only things that you can chase on your own accord.

This made me think about how I have a lot of friends who go into Big Tech. A good number of them say that they want to pursue their own company eventually, but want to get their start at a big company to build up their skills. I asked Bryant what he thought about this approach:

There’s two kinds of learning that you can do at a big tech company. One is technology related. So you can go and immerse yourself in a technology, and be surrounded by technologists that can help you. That’s something very valuable for sure, but learning how to do things the way Meta or Google does things is not transferable at all to startups. None of their processes matter. None of their ways of thinking about building products matter. It’s just a whole ‘nother ball game. There are maybe some professional skills that you get to pick up. Communication, the ergonomics around the work–such as just documenting your work, making your work transparent, and just picking up good habits–that’s for sure. But there’s nothing like working in an early stage startup where you’re building something from nothing. You know, you’re almost never doing that at a big company.

I was somewhat surprised that Bryant felt that the Meta or Google way of thinking about products was applicable, so I pressed him to elaborate:

So actually, that’s a great example of something that I did retain. It’s more so the principles at which you approach building a product, right? Developing customer empathy, ensuring you’re not over-engineering things really matters. Facebook and Meta have an abundance of resources. Engineers at large companies are very good at building incredible things that are well-defined in a narrow spectrum. However, in a startup, you’re trying to go as wide as possible with what an engineer could potentially contribute to and build 60 to 80% of it. It doesn’t need to be perfect.

Bryant’s comment about over-resourced companies made me think about the opposite, under-resourced companies, and how I often hear about employees at those companies working weekends and long nights. I asked Bryant if he thought that was necessary in a startup:

There’s a time and place for it. I don’t believe nights and weekends are required. It’s important for people in their 20s to find their limits professionally and personally. This means making time for personal things like dating, hanging out with friends, and attending events. It’s about striking the right balance. For instance, I encourage my team members to take vacations when needed. It’s crucial for startup leaders to have a good pulse on their employees, understanding their strengths and weaknesses, and checking in on their well-being. I don’t believe anyone at SpaceX or elsewhere can stare at a problem for 100 hours a week and feel productive. It’s important to step out of your zone, draw inspiration from different things, and take breaks. To live a balanced life. When I say that people should find their limits professionally and personally, it’s like that limit is different for each person. But you have to feel like you’re able to stretch, build the muscle for your mental and physical strength to stretch when you need it. I think that’s really important to do.

SHOUTOUTS  

Webflow is hiring across multiple functions! Please visit this link to find and apply for open roles, or feel free to get in touch with Bryant at bryant@webflow.com if you would like to reach out personally for opportunities.

38 at the Garden, the short film about Jeremey Lin which Bryant helped produce is available to watch on HBO Max. The film is 38 minutes short and is a must-watch for all Asian Americans.

Thank you Bryant for speaking with us!