Mattermark Founder on Being Self-Taught in Silicon Valley

By “everything,” we mean engineer, marketer, analyst, salesperson, founder, writer, and investor.

Investing, writing, and engineering might seem like fundamentally different skills, but among the qualities that make Morrill remarkable is the ability to quickly teach herself the skills of any field she enters. At the center of her approach are three basic principles:

1. Push every shiny button

Morrill's curiosity guides her career. If she's interested in a subject, she can't help but pursue it. If she sees a shiny button, she has to press it. In her first job after dropping out of community college, Morrill worked at a shipping company in accounting. She described her first day using its in-house accounting software:

I remember it had a play button, just like a play button on YouTube... I'm the kind of person that if I see a button, I'm gonna click it. I click the button and I got this error message saying that my script had failed to compile. I was like, “What is this? This looks kind of cool.”

Digging deeper, she found the software would let her run her own scripts. The catch was the scripts had to be written in PASCAL—a language so uncommon in production that there are currently no companies hiring for it on AngelList. But she learned enough PASCAL to quickly automate most of her work.

This pattern of pushing every shiny button carried on to her next job, as the first employee at cloud communication platform Twilio. Her role was a do-it-all marketing position—write content, attend conferences, send a metric ton of cold pitches—but Morrill did one thing most early marketing hires might not: She tinkered with the company's code.

She couldn't help playing with the platform, thinking, “What happens if I connect with Twitter? What happens if I touch this part of the API?” She ended up building a door buzzer for her apartment that would automatically connect visitors with the roommate they arrived to see. She built TweetToCall, a service that let people make phone calls using Twitter. Eventually, her experiments brought so much attention to Twilio that she was able to build an entire platform, called Twilio Doers, where other engineers could show off their Twilio-based side projects.

2. Learn just enough to build what you need

When discussing her approach to engineering, Morrill says, “I've always written code to solve a problem... I need to have a goal.”

When she was young, she remembers wanting to spend more time with her father, who was a busy accountant. She learned enough Visual Basic to automate parts of his work and help him get out of the office earlier. Later on, when she demoed the Twilio API at conferences, she would describe herself as a “professional hobbyist" who learned enough to hack together inelegant prototypes. After Mattermark launched and it became clear she could no longer manually update profiles for thousands of startups, she learned enough to build software that could crawl online resources, consume APIs, and populate the information for her.

Slowly, by learning enough to conquer each project she took on, she became a talented full-stack engineer.

You can see this model of self-education in any field Morrill pursues. When she launched marketing at Twilio, she'd never been a marketer. Instead, she started with a key metric and goal—increase the number of developers using Twilio's platform—and found success by working backward from there. She knew she could write stories, so she wrote them for a developer audience. She wrote over 1,000, in fact. She also knew developers attended tech conferences, so she learned about event marketing and presented at events across the nation. She never, however, thought, “What do I need to learn to call myself a marketer?” Rather, she asked herself, “What do I need to learn to get developers to use Twilio?”

The lesson here is simple: Decide what to learn next in your career by working backward from your goal. What do you need to know to build your next project?

3. Take big risks—and don't hide your losses

Morrill summarizes her philosophy on taking risks by saying, “If the risk won't kill you, take it. At the end of your life, you're always going to wish you took more risks.”

You can see evidence of this mindset in the risks she's taken throughout her career:

• Jumping in as the first employee at Twilio
• Quitting Twilio to launch Referly, the startup that would eventually pivot to become Mattermark
• Cutting checks as an angel investor to pre-seed companies

Morrill's career is one all-in bet after another, and not all of them worked out perfectly. Mattermark, for example, started with a strong run. Between 2013 to 2016, it grew from $0 to $300,000 in monthly revenue and raised more than $17,000,000 in funding. But it ultimately sold for less than $1,000,000. In the bets that didn't pay off, you'll see another key to Morrill's high-risk strategy: her transparency.

Morrill is constantly sharing her thoughts without filter. In her project postmortems, in her writing and critiques of popular startups, and in her interviews, she offers a clear window into her thought process. She relies on transparency for two reasons:

1. It saves her time. She doesn't have to invest in a professional persona. She even hired an executive coach to help her be more transparent in business, removing the separation between her “work” and “home” personas.
2. It gives her instant feedback. “I'm wrong all the time, and people love to tell me," she says. "I learn a lot from that, too...It's like they're the internet spellchecker of my logic.”

Being self-taught means you're typically jumping into the deep end of a topic with little background. You need to have the stomach to take that risk, but also be able to commit to it and learn quickly. The easiest way to do that, in Morrill's view, is to live as transparently as possible.

Always bet on the "x-factor"

When Morrill reflects on her career, it's clear a strength lies in her ability to identify potential—be it in ideas, people, or companies. As she says, “There are things that feel intuitively right to do for me, and they're based on a lot of data and patterns that I'm ingesting subconsciously, not fully understanding. I call it the 'X Factor.'”

For example, when she met the founders of InternMatch in 2010—now part of student job marketplace WayUp—she was still working at Twilio. As a marketer, she did not have the funds to invest freely in startups. However, she remembers seeing the “X Factor” in its team and asked if she could invest $5,000—an investment that would later return well for her.

It was her first investment. She didn't work in venture capital; she hadn't founded a company yet, but she saw potential in the founders of InternMatch and jumped in, taking as much risk as she could afford.

Morrill isn't the only self-taught success in Silicon Valley. Like other autodidacts, her abilities to recognize potential, to learn just enough to achieve her goals, and to take risks others won't are what allow her to thrive.

Photo by Danielle Morrill