If you’ve only got a couple of minutes, here are our favorite highlights from the interview.

• -    On how to identify a winning founder: “Great, thoughtful design. Great design tells you if the founder is focused, has good taste, understands the simplicity required to connect with the average consumer, and has a strong, specific point of view on what they’re building. It has always been my barometer. Great design is harder to identify than it sounds, though.”
• -    On negotiating a job offer: “Receiving the Snapchat offer was more of a ‘God bless you, this is twice as much as I was making as a reporter,’ type of reaction. There was no negotiation. In hindsight, I think that given the value I was providing, I should’ve asked for more. But that’s the unfortunate thing about media, which is that you have these incredibly savvy and thoughtful people, but because of the economics of online media, they’re paid far less than other professions.”
• -    On deciding to leave Snapchat “I can’t take credit for this, but the stock did start falling through the floor one month after I left. A pretty wild coincidence, but you could argue that there is a through-line: I was feeling a lot less positive about the company internally and where it was heading. I had become one small voice in a very crowded room, and as so many creatives do, I felt like people weren’t listening to my ideas as much anymore.”
• -    On whether startups are worth the risk: “In my view, the benefits of joining a startup outweigh a lot of that risk if you feel that you’re at a high level doing what you do. There are so few ways to build wealth these days on a salary alone, so I think it’s a great idea for people to try at least a few times on some growing companies where they’re able to get equity, especially if you believe in the company and the founder.”

Note: The following is an edited transcription of a live interview with Ellis.

Great, thoughtful design.

That sounds easy to recognize, but I feel like over the years (and even internally), I think so much about why people do what they do. I love design, art, games—I’m thinking deeply about interfaces and the designs of everyday things. Great design tells you if the founder is:

• -     Focused
• -     Has good taste
• -     Understands the simplicity required to connect with the average consumer
• -     Has a strong, specific point of view on what they’re building

Design has always been my barometer. Since I’ve cultivated that set of criteria, it’s often easy for me to tell if a product is going to work or not. But that’s part of what makes my point of view unique, and that’s why it’s hard to tell someone to “Just go look at well-designed products and bet on those”.

I’m not just talking about beautiful products—I’m more of the belief that design is how it works. The product is ultimately a manifestation of a founders’ belief system and their way of thinking. I think that mindset and skillset has given me the ability to pick those winners over the years. There aren’t many companies I’ve been in love with that haven’t been acquired, or done an IPO, or had some kind of good exit.

Is the founder focused on a market opportunity, or a way that they want to change and improve our daily lives? It’s the difference between pitching the tool vs. the benefit. The best founders are always focused on the benefit—they’re putting themselves in the shoes of the consumer, instead of just building something because they can.

My story starts at the University of Michigan. I was an English major—I’d always enjoyed writing—but mostly because I didn’t get into the business school and didn’t know what else to do. I don’t think, at that stage, anyone really knows what an English major goes on to do.

Then I discovered a program called NELP, the New England Literature Program. It was a group of students who went to a summer camp in Maine for 8 weeks, had no electricity, read the Transcendentalists (like Thoreau and Emerson), lived in log cabins, made our own food, and had discussions all day about why we’re all here and what we truly believe.

When I got back, having gone fully hippie, it felt like the right thing to do to continue with writing in some form. And the thing I most enjoyed writing about the time was technology. I was a bigger fan of consumer tech than anyone I knew.

I knew if I wanted to write at one of the tech publications I loved (like Engadget and Gizmodo), I’d need some clips. So I reached out to a women’s leadership newspaper and asked if they wanted a tech blog to grow their blog and get into productivity tools – something every leader needs. Using those clips, I applied to a few sites and I ended up at Business Insider.

Business Insider was the perfect place: they hired 20-somethings straight out of college, paid them 35 grand a year and some dollar pizzas to churn out a bunch of slideshows every single day. I was writing so much at the time that I was able to start finding my voice as a writer, meet lots of founders, and ultimately figure out what I truly wanted to write about, which was software design and startups. That was the impetus of where I am today.

I realized that I was nowhere near as much of a newshound as all my peers. And I didn’t want to be an editor in chief. Maybe, I thought, I could be a columnist, but was that really what I wanted to do for the next 50 years?

What I enjoyed most about being a reporter was getting to know all these incredible founders and helping them tell their story (and even writing their positioning in some ways, which is what a headline is). It was rewarding to hear the love and support from those founders who thought I’d found a really interesting way to bridge the gap between their company and readers.

I cared way more about what those tech founders thought as designers and my idols than what my readers actually thought. I saw that my passion was working with those founders, and I wanted to be earlier in the process than 2 weeks before launch.

Fortunately, I’d got the opportunity to know Evan Spiegel after writing a few Snap exclusive features.

He basically said, “Hey, I think you’re smart, and I want you to be able to do whatever you want to do here,’ and gave me the free reign to try out a bunch of different jobs at Snap: from UX writing to business marketing to PR & comms. Thanks to that flexibility, I kind of became the Snapchat philosophy person and evangelist.

There was this idea at Snapchat that the app was the fastest way to communicate. I would be the one asking, “well, who wants a faster way to communicate? Why? What does it do for you?”

Once the marketing org fully got spun up, I was introduced to some frameworks that made me realize there was actually a precedent for thinking about products that way. So that’s become my passion in my work today and in the past: helping translate powerful technologies to how they actually improve your life every day. That’s something that doesn’t always come easily to most technical founders (and even the consumer-savvy ones like Evan).

This all led to the campaign I’m most proud of working on, called Real Friends, which essentially said Snap was the fastest way to communicate so that you could deepen your relationships with your best friends. And that wasn’t an invention. It was a reflection of how people actually used the app.

I enjoyed (and still enjoy) working on that puzzle of making these products as powerful and interesting as they can be to the end consumer.

I understood almost none of it. Because companies can’t technically give you financial advice about your equity, even when they brought people in to explain this stuff, it left a lot of question marks—and you’re still the one who has to weigh the options and figure out what to do on your own.

I feel like you find out more from friends who may give you recommendations, or a site like Investopedia, or YouTube, which often give you more clarity than you’d get from company leadership.

Receiving the Snapchat offer was more of a “God bless you, this is twice as much as I was making as a reporter,” type of reaction. There was no negotiation.

In hindsight, I think that given the value I was providing, I should’ve asked for more. But that’s the unfortunate thing about media, which is that you have these incredibly savvy and thoughtful people, but because of the economics of online media, they’re paid far less than other professions. Hopefully, as we move towards more newsletter and subscription services, media people will get paid a lot better.

When you join a company that gives you equity, you become an investor (whether you really want to or not). It’s a bittersweet thing, because as privileged as it is, it turns you into a gambler. I’m not a gambler by nature.

In reality, equity is part of your compensation, and you have to think about it that way and you have to be mindful of the risk. When the company goes public, you no longer ask yourself “Do I believe in this company?” but you have to ask yourself “Would my money be better elsewhere?”

That was the thing I didn’t ask myself, because I was such a believer in Snap. It’s easy to be a believer when everything’s going great and you think you understand the company better than almost anyone else. In reality, though, it’s hard to say with certainty why a stock goes up or down—you think you know, but especially with Snap (which was uniquely misunderstood by adults), it ends up being more about public perception than any of the truths or things coming down the road. That gets stressful.

If your company goes public, my advice would be to think about whether your money is actually still best-placed in that company, or if you owe it to yourself to diversify.

Look, I can’t take credit for this, but the stock did start falling through the floor one month after I left. A pretty wild coincidence, but you could argue that there is a through-line: I was feeling a lot less positive about the company internally and where it was heading.

At the end of the day, I just wanted to start writing about new ideas again. I’d been working on Snap for 7 years, and we were public and beholden to Wall Street. I became one small voice in a very crowded room, and as so many creatives do, I felt like people weren’t listening to my ideas anymore and that writing about Snap was getting stale.

I also knew I didn’t want to be a creative strategist for the rest of my career, which was what I was doing at the end of my run at Snapchat. It’s fun, but it’s not an empowered role.

When the opportunity with The Browser Company came up, it felt like the perfect transition to do what I wanted to try next.

People always say that startups are risky jobs to take. But I don’t think they are. Part of being at a startup is committing to deeply understanding the business’s status, where it’s heading, and how much runway there is.

I’ll caveat this next piece by saying the job market today is tough, so this might not fully apply. But my general belief is that, if you think you’re at the level of skills and intelligence that make you a candidate at a top startup, historically it hasn’t been all that hard for people whose startup crashed to find another job—there are always so many new startups being built.

In my view, the benefits of joining a startup outweigh a lot of that risk if you feel that you’re at a high level doing what you do. There are so few ways to build wealth these days on a salary alone, so I think it’s a great idea for people to try at least a few times on some growing companies where they’re able to get equity, especially if you believe in the company and the founder. It’s one of the great opportunities to build wealth. The greater risk to me is to not try things out at one of these startups. There are so few opportunities to save and build wealth without them.