At only 18 years old, Tiger Shen already has a history in software that would make many engineers envious. He’s worked at Caviar, Square and Braintree, and he recently completed Bradfield -- an intensive course designed supplement a traditional three year computer science degree. He began programming at age 14 -- by teaching himself.
His initial motivation? “Honestly, I was really bored in high school,” said Shen, during his recent interview with the popular Breaking Into Startups podcast. His response may have been casual, but his approach to life is anything but. Not content to rest on the cushy rewards of a comfortable job, he continues pushing himself and will be co-founding his own startup this year.
A mere “hobby” with big payoffs.
Shen began teaching himself code at the start of high school. He was on the basketball team and would come home from practice each day with loads of extra energy. Rather than playing video games or binge-watching Netflix like a typical teenager, Shen spent his extra time on code. His older brother, also a computer programmer, recommended Michael Hartl’s Ruby on Rails tutorial as a good place to start.
Shen dove into the book with full enthusiasm -- and found that he didn’t understand most of it. “I was doing a lot of copying and pasting at this point,” he said.
Even though his first pass through Ruby on Rails was a bit beyond him, he absolutely loved seeing the final product. Having a working web app that he could manage on his own computer was inspiring. “Seeing what I could create; it was kind of addicting.”
Shen decided to go through the book again, this time only referring to it when he “felt like he needed to.” Under this stipulation, he still ended up referring to it 90 percent of the time. Instead of giving up, Shen worked through the book another three times, until he was sure he had truly mastered the concepts it contained. By then, and with the help of a few more tutorials, he felt confident as an aspiring web developer.
Be ready to accept new opportunities.
In fact, Shen’s self-described “overconfidence” helped him find success in his career path. He began aggressively applying to internships, most of them at a college level, for which he was not technically qualified. Eventually, after a flurry of emails, he received an offer from Caviar, a food delivery company. Although the internship was unpaid, Shen knew it was an opportunity to get his foot in the door.
Throughout the internship, Shen’s relentless work ethic never let up. He was supposed to start working in the summer, but instead cut deals with his teachers to let him work on his computer during class. “I tended to talk a lot in my high school classes, so it was a good way for them to get me to quiet down,” he said. Eventually, he was upgraded to a paid position. Around the same time, Caviar was acquired by Square, a financial services company founded by Jack Dorsey, who is also the founder and CEO of Twitter. Shen continued to work at the internship, now as a Square employee, until he graduated high school.
But what would he do next? That was the real question -- a question that’s growing more and more popular among the millennial generation. There’s a growing trend nowadays to forgo college and instead embark on a shorter, more specific education experience, like a coding bootcamp, Product School or MissionU, which gives students a fast track course on data analytics. Ryan Craig, managing director of University Ventures, calls this type of disruption “The Great Unbundling.” Rather than shelling out hundreds of thousands on a four-year program, students can choose their education experience a la carte, focusing on the jobs they want to do and the skills they want to learn. It’s the kind of disruption that Breaking Into Startups is keen to discuss, since their podcast is all about alternate career paths to tech. Breaking Into Startups focuses on recognizing and surfacing the stories of people in tech and business from non-traditional backgrounds, people like Tiger Shen.
Related: Do Your Kids Really Need College?
Be aggressive in your approach, but don’t be afraid to change plans.
Up until this point, Shen had always planned on attending college. That was what smart, successful people did, right? However, since he graduated high school at just 16, he had a little time to reconsider his plans. Originally, Shen had wanted to take a gap year before starting school. He hoped to travel the world. However, he realized quickly as he started to make travel plans that this was a difficult undertaking for anyone under 18. There were too many hoops to jump through. Instead, he began looking at more programming internships.
Again, once he had committed to the idea, he took a proactive approach. He emailed more than 500 companies. At first, he tried his best to hide his young age, but this didn’t always turn out well for him. Recruiters would find out during the interview process and explain they were looking for someone older. He found more success after he changed his strategy. Rather than concealing his age, he used it as a branding tool to help him stand out. After all, he had not only graduated high school two years early, but he already had a surprising amount of programming experience.
Being upfront about his age also provided Shen with a self-selective filter. He discovered that companies who were willing to take a chance on someone young were just the kind of forward-thinking, unconventional companies he most wanted to work with.
At one such company, Shen received not an internship offer, but a full-time offer, which led him to rethink his strategy. Maybe he didn’t need to go to college after all. He started applying for full-time positions, leveraging the offer he already had in hand. “In some ways,” Shen told Breaking Into Startups, “it was easier. Companies were less worried that I was going to work for them for a few months and then disappear off to college.”
He settled down with Braintree, a fintech subsidiary of PayPal. Braintree was offering a very persuasive salary, but also a considerable amount of mentorship, which appealed to Shen. They practiced paired programming, which meant he got to work on the exact same lines of code as his senior partner, at the same time. He also loved the discipline of the financial tech environment. The additional regulations kept him on his toes and forced him to never be lazy with his code.
Never stop striving to be more.
After 18 months with Braintree, Shen could have settled down into an excellent job, one with great benefits and coworkers. Since he worked on their payments team, he was producing code used by thousands of companies, from tiny startups to tech giants like Uber. However, true to form, he could not pass up an opportunity to better himself. During his time at Braintree, he met Ozan Onay and Myles Byrne, the founders of Bradfield, a unique programming school. As opposed to a coding bootcamp, Bradfield seeks to educate self-taught developers on computer theory. It’s a great for those don’t have a formal degree in computer science, but want to close that knowledge gap.
Though skeptical at first, Shen eventually decided to quit his job and complete the course in just three months. It was a busy three months. He would finish three classes in three weeks. However, he was grateful for the extensive instruction he was given on everything from networking to database structures. Much of it has proven immediately useful, but Shen also believes the credentials will help him in future leadership roles down the line in his career.
Shen credits his early success to great mentorship, continuing education and hard work. Personally, he hates the child prodigy label. “I devote a lot of time to this," he said. "That’s what it comes down to, not some mysterious genius. When I hear child prodigy, it makes me want to work even harder, just to prove people wrong.”
His best advice for anyone else looking for success in the tech industry? “Don’t cheat yourself. If you don’t understand something, admit you don’t understand it, and keep working on it until you do.” He advises a positive attitude mixed with brutal honesty. Believe you can get better, and acknowledge your current shortcomings.
Now fresh out of Bradfield, Shen is ready for his next big thing. This time, he’s helping to start his own company, together with a couple of trusted cofounders. He’ll be making a move to Denver, where he’ll be developing an app to solve problems around shipping and logistics. One thing is for certain: we can expect to hear a lot more about him in the future, probably sooner than later.
Shen's original interview was recorded on June 2, 2017. Listen to the full episode on the Breaking Into Startups website.