Ian Cinnamon

The son of two Hollywood sitcom writers, Ian Cinnamon learned to value creative freedom from an early age.

Growing up in Los Angeles, he took his parents’ creativity to heart, but then surprised them with his passion for science and math — and especially computers — over art. Cinnamon started programming in Java at age 7. At age 9, he posted a game he made — Tic Tac Toe — online. When someone bought it for $2.50, Cinnamon realized his programming skills were worth something.

He was 15 when he wrote Programming Video Games for the Evil Genius, an award-winning textbook for teenagers published by McGraw-Hill. Later, he developed several best-selling iPhone apps. Cinnamon graduated early from MIT with a degree in brain and cognitive science, then took off for Silicon Valley to advise the executive team of a public billion-dollar technology firm. Before starting at Stanford, Cinnamon founded Synapse, a startup that uses artificial intelligence to help security screening systems at courthouses, schools, office buildings, and airports automatically detect weapons. The technology has been piloted at venues around the world.

What was it like growing up as the son of two television writers, and how did your parents help develop your interest in technology?

My parents work together writing sitcoms — Who’s the Boss? and a lot of foreign TV shows. It was a very entertaining childhood. My parents are really funny and creative and they have great people skills. I used to be their technical support as a kid. I’d help them fix the printer. I taught myself to program computers when I was 7 years old. I’d also play videogames, but I got bored with them. I wanted to modify them and make my own. One of the things my parents always instilled in me was be your own boss. You want to be able to have creative freedom. Then, anything you create is truly your own. I was lucky that got stuck in my head from a very early age.

How did you come to write a best-selling book at age 15?

In high school, one the things I felt was really missing at the time was an intro to programming for young people. There were a lot of college textbooks on the market, but I wanted something for people like me. So, I emailed the editor of this McGraw-Hill series I’d read. I asked her if they have any books on programming for younger people. She misread my note. She said, are you interested in writing this for us? That was pure luck. Not until she sent over the contract did she know how old I was. Then my parents had to get involved. But, she ran with it and the book actually did quite well. Years later, in 2016, I noticed drones were getting really popular, so I got back in touch with the editor. She told me, if you think you should do it, just go write it. Writing a book is really fun. It lets you tackle problems in a different way.

Your iPhone app “Car Finder” was at one point ranked #22 in the iPhone app store. How did that app come to be?

During high school I was at the mall with my parents and sister in one of those giant Los Angeles parking lots where it’s easy to lose your car. That night at home I thought, this would be a fun app to make. It was one of the first 200 apps to be released for the iPhone. My timing just happened to be very good. I set a price of 99 cents. I thought I’d make a couple bucks, but in the first couple weeks a thousand people downloaded it. That was one of the first moments I thought to myself, I could be my own boss and make money doing it. I don’t need to follow that traditional path, I can carve my own. It was a big wakeup call.

Why the detour into cognitive science at MIT?

It’s great to build things for people, like apps. But in order to really understand what people will use and want to use and what’s useful for them, you have to have a deep understanding of human psychology. One area of research I worked on, funded by the Department of Homeland Security, had to do with how effective are X-ray security operators. A lot of these operators are in situations where, if they mess up, hundreds of people could die. So, how do you help keep these operators alert? One of my big realizations was that the human brain is fundamentally limited in its ability to assess images. That got stuck in my head.

You had a stint working in Silicon Valley, then after a few years of that you decided to attend Stanford GSB. Why?

There was a lot more I wanted to learn — how do I take everything I’ve absorbed about building software programs and applications and add something that helps me build an incredible organization? I deferred for four years because I started seeing a rapid rise in AI and deep learning. I had a realization that AI could truly automate the security X-ray machine. So, in 2016 I raised money for Synapse, just $10,000 at first. Then over the next three years we raised $6 million. It’s been a wild ride. Eventually, Stanford told me either you come now or you have to reapply. That was a good reality check. Raising money was a big accomplishment, but it was by no means the be-all end-all. I wanted to learn how to build a real company, how to assess market potential, and how to make sure the money I raised would go toward building the best possible organization. I wanted to learn how to better manage relationships with direct reports, peers, and bosses. Even at a startup, as the founder you have to answer to your investors. I wanted to better learn how to take an idea and turn it into a sustainable business model that could grow for years to come. And, most important, I wanted to be surrounded by like-minded ambitious, but diverse, people who I could learn from.

Any specific experiences you had at Stanford GSB that proved particularly useful?

Quite a few. One that stands out is the Entrepreneurial Finance class I took. We’ve raised a decent amount of money for Synapse through venture capitalists. But I would always have a feeling they knew things I didn’t — more about what our company was worth, how to come up with a price. The negotiations felt uneven. As we prepare to go raise another large round of funding, having the knowledge and skills from that class makes me feel like it’s an even playing ground.

What are your hopes for Synapse and your career?

This company is my baby. Synapse has grown at a much faster pace than I ever could have imagined. We’ve deployed all over the world, from Stockholm to Tokyo. Osaka Kansai Airport has bought our system, and we’re in a five-year deal with them. We’re in the San Jose, California, airport as a demonstration with TSA. We’re about to install at several courthouses and federal buildings throughout the U.S. in the near future. If we can help make things even a little bit safer, it’s a big win in my book.

Do you think AI is really going to take over people’s jobs?

We have to be honest with ourselves — machines will absolutely replace jobs. The core question is, what kinds of jobs are they going to replace? You could interview 100 security officers, and I guarantee not a single one will say staring at security X-ray machines is their favorite part of the job. It’s about getting rid of jobs humans don’t want to do and relocating resources.

Photos by Allison Felt