Last week, our own Sahil spoke at Cascade SF about going from being a designer to being a (designing) founder. Cascade brings in industry leaders to educate and inspire designers to create better web experiences. We’re excited and honored to be a part of Cascade’s mission, so I thought I’d steal Sahil’s notes and share some of the highlights from his talk.
Sahil talked about how he went from “making pretty pictures” to making websites to making web apps to making iPhone apps etc. etc. He admitted that each time, he didn’t really have any idea what he was doing. However…
Don’t be afraid to bite off what you don’t know you can chew. You’ll learn to chew it.
Before we dive in, here’s a spread of notes doodled by Lisa Aufox, a San Francisco-based UX designer who’d love to bury her head in a Moleskin at your next event. Let this serve as your outline.
Sahil listed and elaborated on seven tips, aimed at designers, for being an effective founder. Here they are.
1. Build the thing.
You can’t build a company without building the thing first. Sahil operates on the model that most interesting things can be built in a weekend. When you think about Twitter or Snapchat or Facebook, the actual essence of any of these companies could have been built in a weekend.
Ah, the infamous pencil that started it all. One Friday night (aww), Sahil spent hours creating a photo-realistic pencil icon, and it occurred to him that other designers and illustrators might find it useful. However, he discovered that there was no easy way to sell a digital file. So he decided to build one. On Monday morning, he had Gumroad’s first iteration.
Yes, building a company means raising money, recruiting a team, going from one to a billion users, but just focus on building the thing first. Forget about everything else until you do that. That’s how you start a company.
2. Show people what you built.
Investors are people. People like your friends. Treat them as such. Don’t pitch them. Have conversations.
When he started working on Gumroad full-time, Sahil pinged some friends and showed them what he was working on and told them what he wanted it to turn into. How the world looked today and how it should look tomorrow. It was probably pretty clear to them that he was excited. Excited that he’d built something that worked, excited about how large it could potentially scale, excited about what the world might look like if he was right.
Those were the conversations we had, and they quickly turned into ‘can I invest in it?’ and ‘you should talk to such and such investor friend.’ I accidentally started raising money.
Design is about closing the gap between what a product does and why it exists. That’s what investors are looking at. Did you build a thing that works?
Being a designer really gives you an edge with stuff like this. When you spend a while figuring out solutions to problems, getting feedback on what works, and being able to communicate with others about why a solution was the right one, hey, it turns out you’ve been researching humans the whole time. You understand how they work, and now you’ve built something that they want.
Investors also look at market opportunity. Again, this is where designers have an advantage. You’re able to look at the entire landscape of a problem and distill it down to a core solution. That’s how you built your awesome product that works and is relevant to the world.
Is there a massive problem, and can you fix it? That’s it.
3. Find your team and trust them.
Designers like to do a good job. Or a great job. Or a perfect job! They have an idea of how things should work, how they should look. That’s normally great, but that makes growing a team and delegating a bit scary. But when you become a founder, you’re going to need to do that. Delegate. Someone else is going to become the designer. And you’re going to have to trust that person 100%.
You have to get comfortable immediately. You cannot slowly relinquish control. Trusting someone only 90% of the time is toxic.
4. Build your company like you’d build your product.
A lot of design is just maximizing function against a resource. Building the internals of a company is similar. Once you start realizing that, you get away from a traditional structure really quickly. Like your code, your teams become more modular. Areas of responsibility become clear and more empowering. You start to design the way your company works internally instead of copying someone else.
We’re a really flat organization with no managers, but that doesn’t mean there’s no structure. Everyone is autonomous within their area. Everyone reports to everyone. We value transparency to a pretty extreme degree.
By the way, our process changes all the time, just like our product does. It likes to change. It’s open to it. The culture of “nothing is sacred” is really important to us.
Design thinking doesn’t just apply to how you approach a product. It can apply to anything.
5. Design thinking is like a super power. Use it.
When I talk about design thinking, I’m not talking about visual design. I’m talking about understanding the architecture of things before executing on them.
At Gumroad, we deal in many different industries. Music, Film, Publishing, Technology, Education, Design. Each one is different. Each one changes all the time. Understanding the nuances of these industries matters. We need to keep our fingers on the pulse of what Taylor Swift says about Spotify and a million other things. It informs us moving forward.
Our approach to product is incredibly simple: We look at all the things creators spend their time doing that’s not making things, and we figure out how to do those things for them.
Understanding the architecture of things before distilling and deciding what to execute on is a designer’s default. It’s a skill that it takes non-designers a really long time to learn. So trust it.
To that end…
6. Rely on your gut.
The process of a CEO is basically identical to the process of a designer. You figure out what needs to happen and why. Then you look at how others have solved it, then solve it yourself based on your needs.
So you have to rely on your gut a bit more. The problem with design is that it’s over-appreciated in the beginning when things look slick, and underappreciated at the end when data wins arguments. Finding the balance often comes down to trusting your gut.
At Gumroad, we’re trying to do something that’s never been done before. There’s not a roadmap. We’re the first ones here. There’s almost a frontier mentality with the amount of unknowns we deal with every day. Yes, there will be mistakes. But that’s okay.
7. Build your life like you build your product.
Being a founder forces you to be at your physical, mental, and productive best. You take the red-eyes, you jump in on customer support when you have a record sales day, you power through the crap with a steady and optimistic attitude when things get rough. You do these things because you know the ROI is there.
For me, it helps to have so many eyes watching me. It’s like having a trainer that’s everywhere at once and just staring at my life. If I sleep well, go to the gym occasionally, take a vacation, then my team knows it’s okay for them to sleep well, go to the gym in the middle of the day, take vacations.
And he means that. The above is a photo Sahil took a few weeks ago by the Perito Moreno Glacier in Argentina. As for the gym, a lot of us are members of the World Gym near the office.
This stuff is important, because if you burn out, you can’t build the company you want. A lot of companies work in a sprint—a rush to cash out. But if our goal is to make it possible for every single creative person—be they filmmakers or musicians, authors or designers—to make a living from selling the things they make, we can’t do it in a sprint.
So what if you don’t have everything figured out yet? Everything is a work in progress. Just get started. Build something.
Gumroad didn’t begin because I wanted to be a founder. It began because I really wanted something to exist and no one else was building it the way that I felt it should be built. So I decided that maybe I was a good person to build it. So I did. Now we’re over 20 folks, but only because we were 19 before that, and 18 before that…
So that’s that. Thanks to Cascade, and thanks to Sahil for letting me swipe his notes. So. Want to join us in our marathon? We’re hiring.