10 Lessons as Founding Designer

of a Stealth Startup

A year ago, I wrote a blog post called 6 Lessons from an Unemployed Designer talking about my fling with unemployment. The next day, emails and tweets started pouring in my inbox. People from all over related to those lessons and genuinely appreciated it. Those lessons ended up being a blessing as it gave me the opportunity to meet so many people. One of the people I ended up meeting was Deny Khoung, the founder of Whitespace and Designer-in-Residence at Formation 8.

Not knowing what Deny wanted and why, I met him for coffee at the Creamery down by 4th and King in San Francisco. He started asking me what I wanted to do and what kind of company I was looking for. After learning about me, he then talked about what he was up to at Formation 8 and the Whitespace program.

Whitespace is a 12-weeks design program that pairs designers up with rising startups in the Silicon Valley. Three days a week I would go to the company I am paired up with, and the other two days I would join other designers in the program and participate in workshops, critiques and more.

After meeting Deny that day, we exchange several emails back and forth. He said he had a company in mind for me. It was a peer review app with a solid team of 3 called Zugata. After a few more questions, I joined the program.

To be honest, I didn’t know what I was signing myself up for. I didn’t get the chance to visit the company I was paired up with, I had no idea who I was going to work, and I didn’t get the chance to see the product. There was nothing on internet about this company because it was in stealth.

So I joined Zugata through Whitespace. In those 12-weeks, I’ve learned so many things, but here are 10 things I’ve learned as the first and only designer at a stealth startup.

10. Learn to design all sorts of things

At a larger company, you usually work on one feature on one platform.

At a stealth startup, we don’t have that luxury. But sometimes “luxury” could be too comfortable that it’s uncomfortable and boring. For me, “luxury” isn’t always practical. At Zugata, I get the opportunity to touch all sort of things.

One day, I’m designing for iOS, the next day, it’s the web app. Sometimes, it’s designing email templates. And other days, it’s creating presentation decks and designing swags. Being the lone designer, I’m always designing all sorts of things. Although there is a lot to tackle, my job is never boring; I love the variety.

09. Learn to hustle

“Fail fast, learn faster” is every startup’s motto.

It’s true at Zugata. We’re moving fast; we’re whipping up features, making a lot of updates and iterating quickly. To help me hustle as a designer, I sketch a lot. I generally spend more time on paper than in the Sketch app. I’ll even create a prototype with those sketches in Invision to make sure the idea is in the right direction. Once that is done, I skip the wireframing process and hustle straight to the visuals.

At a stealth startup, you have to adapt to the speed. You learn that shipping quickly is the best thing you can do for your product. You have to get something out and test those big ideas and hypothesis. You hustle to produce, iterate, fail and ultimately, learn.

08. Learn to trust it’s good

At a startup, you need to learn to trust that your work is good enough (for now).

I am hustling so quickly here that sometimes I end up creating something that looks like 💩. Granted, it may not look like that to others, but as a designer, I see all the flaws and imperfections.

As designers, we have all these standards and principles; we are generally pixel officers and consistency polices. Though, it’s difficult to admit “it’s good enough,” you just have to adapt to it. Again, getting something out there is the best thing you can do for your product. You can always go back and clean up those design imperfections as you iterate.

07. Learn to be a swiss army knife

Not only are you designing all sorts of things at a stealth startup, you will be doing all sorts of things outside of your expertise.

At Zugata, not only am I designing, but I’m coding email templates, writing content, conducting user testings, demoing the product, ordering team lunches, watering plants, and much more. You learned to be a swiss army knife.

The things you do will not be listed in your job descriptions. In fact, you will get your hands dirtier than you expected because this company should be your baby.

06. Learn to ask many questions

At a startup, it’s your responsibility prioritize your endless task, because you might not have a product manager. To help you prioritize, you ask a lot of questions.

Here, we ask a lot of questions when we are doing user testing with our prototypes, demoing our product to leads, sending out surveys to our customers and when we are brainstorming amongst our team.

Not only does asking questions help you prioritize, it does a whole lot more. It will help you understand your customers, quickly gather product insight, get the feedback you need to make the smallest change that could make the biggest difference in our product. Questions are free, so ask them.

05. Learn to be flexible

At a stealth startup, plans and ideas change drastically.

One day we decide we are not going to do something, and then the next day we end up doing it. Or you may be planning to work on product one week, then end up working on marketing or recruiting materials. You learn to let go on and carry on.

Startups are known to pivot to help the company grow, so you have to learn to be flexible and adaptable to changes. Don’t get too obsessed over certain ideas or tasks because it may change.

04. Learn to ask for forgiveness

Grace Hopper, a U.S. Naval officer and an early computer programmer once said, “it’s easier to ask for forgiveness than it is to get permission.”

At Zugata, it’s just better to ask for forgiveness than permission. Some days, the front-end engineer and I would whip up new features amongst ourselves. I would quickly mock up a new design and he would implement it. We did this several times, sometimes we don’t nail it; but that’s when we apologize and revert the changes.

Everyone has a lot of responsibility on their plate at an early stage startup, so taking initiative on things without being asked will push the product to the next level. A stealth startup also can’t afford to have people sitting around being told what to do; you just do it. Like Teddy Roosevelt once said, “complaining about a problem without posing a solution is called whining.” Go on, take the initiative and fix it. If you made a mistake, apologize and learn from it.

03. Learn to be transparent

As the only designer at a startup, it gets pretty lonely.

At Zugata, I’m always posting designs and sketches on the board so everyone can see it. When iterating on those design, I end up sending it to everyone on Slack to get everyone on board. To get feedback, I’ll host design sessions inviting everyone.

Being transparent helps you gather feedback quickly, iterate quickly, understand if it is technically feasible early in the process. It will inform your engineers what’s coming up and will create a frictionless process when you hand it to them. Even if your designs aren’t completed, you have to learn to be transparent and share them early and often at a startup.

02. Learn to design beyond tangible things

Not only are you designing products at a stealth startup, you are designing a culture.

At Zugata, I initiated traditions like creating post-its art to add color to a dull office, awarding someone with the “Big Z” for doing something awesome, surprising coworkers on their birthday, and making guests leave a note when they drop by. All of this becomes part of our culture.

Even though, this may not be part of your job description, it’s every early employee’s responsibility. You will be spending many hours at your office, so might as well make it fun and enjoyable. Fill it up with smiles, laughter and delightful experiences. And remember, it’s not the perks that makes your office enjoyable, it’s the people and the culture.

01. Learn to love the uncertainty

At an early stage startup, nothing is set in stone, and it’s scary.

I imagine it like being a parent for the first time. You’re just still trying to figure everything out; you’re still figuring out the product, the company, the team and the culture. We don’t know where we will be next year. We don’t know if we’ll become a sustainable business. We don’t know if we’ll fail and fold. Everything is just uncertain.

But you learn to love it! You learn to love the uncertainty and embrace the unknown of a stealth startup. Because no matter what happens, you will learn something valuable from it.

A few notes:
• This post is based off a talk I did at my Whitespace Finale in Spring 2015
• Zugata came out of stealth in October 2015
• Zugata is hiring