Image: Twilio

To many founders, entrepreneurship is more of a personality trait than an acquired skill. For Twilio founder and CEO Jeff Lawson, that path in life started when he learned how to code.

“I pretty much immediately started doing entrepreneurial things with that skill,” Lawson said.

After leaving his undergraduate computer science program at the University of Michigan, Lawson founded his first company,, which provided academic content such as lecture notes for college courses during the dot-com era. After a few years, the founding team sold it to a competitor.

Then, two of his friends were starting a company that would become StubHub, and asked him if he wanted to join. Lawson became the founding CTO at StubHub, helping to launch the site and build the company. Eventually, he realized that he wasn’t excited by the product category.

One of the previous investors in his first company approached Lawson to brainstorm ideas for a new company. A group of them met at the investor’s summer home in the Hamptons for nine months, coming up with close to 1000 ideas, 100 of which were decent, and 20 of which became business plans. The business they agreed on was a brick and mortar retailer for extreme sports called Nine Star, which sold products for sports like skateboarding, BMX, and snowboarding, among others.

Although he was building out unique tech tools for Nine Star, he came to the same problem of having no real passion for the business. So, after a few years in, he took a leave from the startup world to go work for a bigger tech company.

“I said ‘I’d like to see the other side of that picture, I’d like to understand how a well-run company operates,'” he said.

In 2004, Lawson took a job at AWS in Seattle. After a few years spent working on the core AWS products and learning as much as he could about working for a bigger company, he left to start another company.

Among the three companies he had started, Lawson had noticed two threads: The agility of software allowed for a differentiated customer experience, and deeply integrated communications were also necessary for a great customer experience. The problem was that traditional legacy communications systems took too long and cost way too much.

“The notion that you would spend multiple years and multiple millions of dollars to build anything is contrary to the whole ethos of software,” he said.

So, his team started Twilio to bring communications into the age of software. They approached the issue in a developer-centric fashion, thinking about how they could solve the problem for other companies. Twilio is a cloud communications company that provides APIs for text messaging, VOIP, and other modes of communication.

“Software is now moving from the backoffice to the business model,” he said. “Every company needs software to build a differentiated offering.”

And this emphasis on software is changing the way the companies can grow and innovate. By building quickly and iterating, the barrier to innovation has been lowered and, Lawson said, that experimentation is fundamental to the innovation we are seeing today.

Although the high valuations of today’s startup ecosystem continue to grab headlines, Lawson said there is real economic benefit to many of the products that these companies are building today.

As someone who has been in leadership at multiple tech companies, Lawson has had his fair share of learning opportunities when it comes to working with a team. To him, the two most important things as a leader are listening and communicating, which he works out through a meeting he calls the CEO roundtable.

The idea is getting feedback directly from people in the company, without going through the hierarchy to get it. He usually holds a roundtable every week with 18 employees in the company and asks them those two questions: What’s working well, and what do we need to work on?

It’s these thoughts and practices that have led Twilio to its current success. The company recently reached a billion dollar valuation and continues to grow.

In his own words…

What do you do to unplug?

“The most time I spend unplugging is time spent with family. I have two young kids, I have a three year old and a one year old. So, spending time with them and unplugging, putting away the phone, putting away the computer is tremendously fulfilling. Just giving my attention to them is one good way to unplug.

“The other one that I’d say is interesting, which is something I’ve done a little bit of lately is to go to actually the race track and drive a car on the racetrack. You can rent these old Mazda Miatas from the 90s, that are all beaten up and decked out for the track, and race them on the track. The thing that’s really therapeutic about this, almost, is that driving a car on the racetrack requires your complete and utter concentration. You don’t want to screw up and drive the car off the track or get into an accident or anything like that. And, there’s so few times in life today when you actually concentrate, use your whole brain devoted to one task. In the age of smartphones and Twitter and social media and multi-tasking everything, it is actually very refreshing (and actually tiring) to focus so intensely on one task, that I find it really therapeutic to do that.”

What’s the best thing you’ve read lately?

“First of all, on the fiction side of things, I read The Martian and that book–I loved it. It’s a very geeky, scientifically accurate, story about what would happen if an astronaut were stranded on Mars and had to survive there all alone, 30 million miles away from the closest human being. It’s a fascinating story and a great read.

“On the nonfiction side, one of my favorite books is a book called Made to Stick. It’s a book about how to communicate ideas so that people remember them. It’s such a simple concept, but the way they articulate the aspects of human communication–why some ideas stick and resonate and get retold, and other ones nobody ever adopts, is such a fundamental human concept. As somebody building a company, and needed to communicate ideas very frequently, I found that book and some of the ideas in it are just very impactful in how I spend my time and how I focus on communicating ideas…”