Career Spotlight: Jason Shen, Product Manager at Facebook, Serial Entrepreneur, NCAA Gymnast, Angel Philanthropist

Lessons from founding multiple companies, qualifying for the US Junior National Gymnastics team, and setting two Guinness world records.

Every month, I feature a high performer on a ‘Career Spotlight’ and interview them on their journey, mindset, and habits.

Last month, I interviewed Luke Niu, MBA Candidate, Product Manager at Lalamove, D1 Track Athlete, and TEDx Speaker — to discuss the importance of setting values, reframing the idea of resilience, and his approach to performance.

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This month’s spotlight will be with Jason Shen — Product Manager at Facebook, Techstars and Y Combinator backed entrepreneur, angel philanthropist, NCAA gymnast, and resilience writer, speaker, and coach.

At a first glance, you probably had a similar reaction to me: Jason’s accomplished a lot. 

He’s got an incredibly diverse set of experiences across academia, startups, tech business, communication, and philanthropy. It’s rare for any individual to get to this level of achievement across one of these disciplines, let alone multiple.

Jason and I both work at Facebook — though in different roles and teams. I first came across Jason’s profile on Linkedin and noticed his experience with building and selling startups, writing online, and performance coaching.

Immediately, I thought: “I have to meet this guy”.

I routinely reach out to new folks (about ~3 weekly) and sent Jason a message via Twitter, and from there we set up a chat. Now, Jason and I regularly talk about tech, business, performance, and growth. I consider him a mentor and role model. The power of cold outreach!

Through this interview, Jason shares his personal experiences, mindset, and philosophy that has enabled him to reach a level of breadth and depth across a variety of subject areas.

This interview is a gold mine of insights, learning, and wisdom. If you want to learn about how Jason built three tech companies, coaches and mentors executives, and excels as a product manager, keep reading.

Also, if you’re the kind of person who likes to get ahead of themselves, you can subscribe to Jason’s newsletter Cultivating Resilience.

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Let’s start at the beginning. Where does your story begin?

Jason:

I was born in Suzhou, which is sometimes called “the Venice of China” because there are many canals and waterways. It’s a beautiful place. When I was two, my dad got a scholarship to attend Boston University for grad school. A year later, he sent for my mom and me.

I was a hyperactive kid. If I had stayed in China, I would have had a lot of problems. Even as it was, my kindergarten teacher Mrs Ward wrote my parents a letter at the start of the year, cc’d to the principal, that was angling to put me into special ed.

I was described as “very impulsive” in my physical movement, was easily distracted and an “exhausting child to work with”. My parents had to really intervene to keep me in regular classes and had me see a psychologist who diagnosed me with ADHD. I’m not sure exactly what changed but by the end of the year Mrs. Ward wrote another letter that captured something about me that I feel even today: 

“Jason has a wonderful curiosity and wants to explore everything. He especially enjoys computer work, games and making things.”

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Given your background, her observation seems accurate. What happened next?

Jason:

The narrative I’ve written for myself has always been that I “grew out of” being ADHD thanks in large part to gymnastics, which I started when I was 6. My mom was herself previously a gymnast and worked as a gymnastics coach at a local facility and so starting classes was like subsidized daycare. We were pretty strapped for money at the time, and that was a big plus.

But now looking back, I’ve been slowly embracing the idea that I’ve continued to be on the ADHD spectrum, maybe not so severe as to have problems keeping a job or having lasting relationships, but my restlessness, need for novelty, desire to do things “my way”, extremely broad sense of curiosity, and disinterest in bureaucracy and rules have shaped many of my life choices.

After a few uneventful years of training, I actually started getting good at gymnastics. I competed in my first national competition when I was 11 and qualified onto the US junior national team at 15. Gymnastics taught me how to face fear, learn new skills through deliberate practice, and perform under pressure.

I was also doing well in school and had a knack for standardized tests. So while I was maybe in the top quintile of my class GPA-wise, I earned a 1580 on the SATs, which helped me get an athletic scholarship to Stanford.

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What was university like for you?

Jason:

I was so excited to get out of the house. Living on the West Coast was a great adventure for me. I studied biology at Stanford because I liked science, but I struggled with actually solving hard problems (so chemistry, physics, and computer science). To round it out, I minored in philosophy, writing a thesis paper on a more ethical allocation of liver transplants.

Biology taught me how to think empirically and experimentally.

Philosophy taught me how to break down ideas and make good arguments.

I spent most of my time with my teammates as we were training 20+ hours a week together, but I also took the opportunity to participate in clubs and develop skills in marketing and design.

My junior year, I dislocated my left knee on a double twisting Yurchenko vault and had to have multiple reconstructive surgeries (I wrote about that experience here). It took me over a year to return to competition.

During my year away from gymnastics, I got involved in a student effort to raise money for microfinance loans to developing world entrepreneurs and members of the working poor. We ended up starting a nonprofit, raising tens of thousands of dollars through student run programs on college campuses across the country. We brought a great group of people together for that work and I’m still close friends with many of them today (three of them were in my wedding party).

In my 5th year at Stanford, I did a coterm, which meant getting a one-year masters (again in biology) and finished out my athletic eligibility. After narrowly losing the championship in 2008, we took home the title in 2009, Stanford’s first win since 1995. The university has gone on to win three more titles in the last 12 years, so I feel like we started something.

The microfinance nonprofit got me interested in business and startups. Despite my struggle with computer science, I had always loved technology and would build websites on Geocities and make my muscles look bigger with pirated copies of Photoshop back when it was shrink wrapped software.

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You graduated with a masters and an NCAA title. What was your next move?

Jason:

My first job actually kept me on campus one more year, where I ran the business side of the Stanford Daily newspaper. It was a rough time, immediately after the Great Recession and I basically cut costs to the bone, laying off people and reducing staff salaries, including my own, to try to keep the organization solvent.

I then got a job doing sales and marketing at an ad tech startup. I quit after less than a year to found a company with my two roommates in San Francisco, one a classmate from Stanford, the other an engineer from UC Berkeley. By a ton of luck and (probably some pattern matching), we got into Y Combinator with a pitch that was so flimsy, we decided to change it the moment we started the program. They actually wrote a book about our class called Launch Pad. Our story is featured heavily in the first and second chapters.

We eventually decided to build a ride-sharing company called Ridejoy.

The “sharing economy”, the warm-and-fuzzy predecessor to the “gig economy” was big at the time, with Airbnb being the hot media / VC darling.

We positioned ourselves as the next big hit and raised $1.2M in seed capital. I know that’s barely a pre-seed round these days but this was back in 2011 ok?

We used our site to share rides to Burning Man and even found a pilot to fly ours out of the desert. (See my video on the trip here). 

We worked on the company for two years but couldn’t build the critical mass necessary to scale the platform. Supply and demand matching was very hard. We even scrapped our entire team and spent six months trying to pivot into completely different directions and couldn’t figure it out.

I was the first to break, tired of feeling trapped in our apartment (we stayed roommates the entire time), and applied for this new program called the Presidential Innovation Fellowship, which was being run by the CTO of the United States, Todd Park, under the Obama administration. I spent six very intense months learning about what it means to build inside the government and helped the Smithsonian launch a crowdsourced transcription website (which is still up today).

After PIF, I didn't want to move back to San Francisco. I decided to move to New York City. It was somewhere I always loved visiting but wanted to see if I could make it as a resident. Plus the dating scene in the Bay Area was notoriously difficult, and I felt like I had better odds in NYC.

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So you moved to New York City. Did you have a job waiting for you?

Jason:

No. I hadn’t lined anything up, as PIF was quite short and there wasn’t time to figure out my next step.

I slept on friends’ couches for almost 3 months while having a ton of coffee dates with first and second degree connections of people who might help me figure out what was next.

One of those conversations with a CEO turned into an “insta-interview” and led me to a role content marketing for a Sequoia-backed enterprise software company called Percolate.

It was my first and only taste of the kind of occasionally toxic bro / sales culture that B2B companies can have. I got great experience writing “professional” on their blog, publishing white papers and leading webinars, but I really wanted to get into product management. Despite having founded a YC company, my management chain wasn’t willing to give me anything other than the bare minimum, lateral move that kept me in the marketing team. So finally, I wrote my own ticket.

I had previously interviewed the director of design at Etsy for my blog, and he had intro’d me to a PM at Etsy, all before Percolate. I replied back to the thread, and, as it turned out, she had just been promoted and needed to backfill her role and was just starting to interview. It was perfect timing.

Percolate wasn’t all bad though. I worked with a designer there named Amanda, who was pretty dope. We both left the company around the same time, started a side project, then started dating, and a few years later got married.

Etsy was my first official PM experience, though I had been doing it in my own way at Ridejoy and PIF for years. I was on a seller focused team (Etsy is a global marketplace) and we built marketing and inventory management tools on desktop web and on iOS and Android apps.  I knew this would be fertile ground for finding a cofounder, and one of the engineers on my team, Wayne Gerard, fit the bill. He had started a company previously, could code on web and iOS, was funny, well-respected by the team, and intellectually curious.

I convinced him to explore some ideas with me, and we got really interested in improving the hiring process (something I often found to be a barrier in my own career). We eventually founded Headlight, a better hiring platform focusing on rigorous yet candidate-friendly take-home tech assessments.

We raised a pre seed round of $650k and landed a dozen customers in NYC and SF. We started by selling software, then services, and eventually transformed into a series of tournaments where we’d give out prizes like an international trip for two or a massive 4k monitor.

Eventually we realized that we were turning into a hiring agency, something that didn’t scale. So we did what I couldn’t pull off with Ridejoy and did a hard pivot. After evaluating a bunch of industries and opportunities, we decided to enter the esports industry.

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That feels like a big change! What happened with the pivot?

Jason:

We definitely had a number of people raise their eyebrows when we told them what our new business was in. But for me and Wayne, it sat at the intersection of a bunch of overlapping interests and experiences: team competition, analytics, gaming, and emerging interfaces.

The new company was called Midgame, and we participated in the Amazon Alexa x Techstars accelerator in Seattle, and the Betaworks Audio Camp.

I got the former head of Cortana at Microsoft to angel invest off a cold email, which I’m very proud of.

We built voice analytics tools and got them in the hands of top collegiate and pro esports teams, and later experimented with a Discord bot that could answer questions and help you while you played games. It was a lot of fun trying all these things but nothing quite stuck, and when the pandemic hit, we were in a tough spot.

We either needed to raise another round to chase a brand new idea or try to get acquired. With very little runway left (we actually dipped below $0 temporarily at one point), we set up conversations with Twitch, Coinbase, and Facebook. 

Ultimately the best deal and the only option that would keep the team together (me, Wayne, and our lone engineer Lilly Chen) was Facebook.

It was bittersweet to say goodbye to all our users. Unlike Headlight where our customers were engineering or HR leaders who were paying for a tool, Midgame was used by individual people who we had closer relationships with and that made announcing our acquisition (and shutdown) that much harder.

We joined directly onto a team called Knowledge Products, which built productivity tools for internal Facebookers, a huge group of about 100,000 people when you include full-time and contract workers. I have been at FB for 16 months (almost 3 “halves”) and already I’m more tenured than 40% of the company (we are still hiring like crazy!).

It’s been an intense whirlwind given we’ve been remote this whole time, but I’ve learned a ton about how to operate inside a big tech co and drive larger products / lead more engineers.

It’s also been interesting to find myself now working with people over 10 years younger than me. I used to be the “younger one,” and all of a sudden that’s changed.

And it was a bit into Facebook that I met you, Andrew!

We haven’t met in person yet but I’ll be going into the office soon and I look forward to connecting there. I’ve appreciated your hustle, curiosity, and discipline as your own career gets started.

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Can you talk about your side ventures, hobbies, and extracurriculars?

Jason:

As someone with a lot of curiosity, I have pursued many side projects. These endeavors have been critical for building skills, meeting new people, having a public body of work, and just keeping me engaged with life.

Overall, it helps develop a sense of personal initiative — knowing you can create something from nothing (doesn’t have to be a startup) just by creating things.

A few that are notable include:

• Writing — I’ve been writing publicly online since 2009, first on my personal site, then Medium, and even Fast Company and TechCrunch. Running my own site taught me a ton about marketing and building things in a “low code” way. Writing for publications builds further credibility and teaches you how to “add to the narrative”.

• AAPI Advocate — I have published surveys of over 1000 Asian men and write op-eds about AAPI issues. This is an important issue for me personally because it is helping (slowly) change the narrative about Asian Americans and AAPI men. It’s made me a better ally for Asian American women and other marginalized groups in general.

• Speaking — I’ve given a TED talk on the future of hiring (minor promo for Headlight) that has 4M views and have spoken at conferences and events in China, Malaysia, Portugal, Amsterdam, Australia, and all over the country on topics including gaming, product management, startups, and Asian American identity. I love the rush of speaking for an audience and performing, which I think comes from my time as a gymnast.

• Fitness Challenges — I have set two Guinness World Records - in Aztec Push-ups (2014) and Burpee Pull-ups (2018), run the SF Marathon, and was named one of the fittest guys in tech by Men’s Journal. I’ve come to realize that working out is critical for my mental health, as it massively reduces my stress and helps me get out of my head. And I love taking on interesting new challenges.

• Philanthropy — In 2020, I started a philanthropic initiative with my good friend Bilal Mahmood (we worked together at that microfinance nonprofit) called 13 Fund. We make grants to local SF and NYC based nonprofits tackling important issues. Our twist is two-fold: 1. We start with a pretty in-depth research paper on the issue (see: the pandemic’s impact on the food industry & stopping anti-AAPI hate); and 2. We recruit others into a giving “syndicate” so we can raise more: our first grant totaled $100k with 17 partners.

• Cultivating Resilience — For the last few years, I’ve been building a body of expertise around resilience and adapting to change. I publish my learnings and explorations on a weekly newsletter called Cultivating Resilience that I’m working into a full-length book. You should definitely subscribe if you’re into any of my work / mentality!

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What are your key principles of success? What habits, mindsets, and behaviors would you attribute your career success to?

Jason:

Try shit, repeatedly

My number one strategy in life is to repeatedly try shit.

When you look at my career path, I usually had very little experience doing what I was doing before I started and I switched directions / locations / industries a lot.

At the same time, I’ve been willing to experiment, fail, and get rejected repeatedly in my ambitions: multiple startups, been trying to land a book deal for 4+ years. I think that keeping this approach has helped me do what I’ve done.

Build meaningful connections

No one ever achieves anything alone.

If you focus too much on just completing your to-do list, you’re missing the bigger picture.

It’s really important to find time to make friends and connect with people in different industries. Because of my varied career path, I’ve gotten to know a lot of people in a variety of domains and this weatherproofs my life because of the diversity of connections.

This also means making time to build friendships that might not have any direct benefit, because you want people in your life who don’t “need something” from you besides your company.

Take time to date.

Dating looks like one of the most “wasteful” things you can do as a young person, but dating for the sake of understanding yourself and finding a life partner is one of the highest leverage activities you can pursue.

Don’t worry about feeling “not ready” or that you “haven’t figured out who you are yet”. The right partner is someone you should grow together, don’t be afraid to let the right person change you.

My life is infinitely better as a married man, even though I have less freedom and time than when I was single. I expect the same will be true should I become a parent in the future.

Reflect regularly

Too many ambitious people are just “go, go, go” and don’t take the time to reflect on a regular basis.

Reflection helps you learn from mistakes, reframe your life, understand what you value at the moment and gives you space to deliberately initiate changes in your life.

It’s worth blocking out time, weekly, monthly, quarterly, or yearly to reflect. Pandemic times has thrown this for a loop for me. but I’ve never missed an annual reflection over the holiday break since graduating college. Here’s the system I use.

There’s a great book by Howard Gardner, the Harvard educator who invented the concept of “multiple intelligences,” entitled Extraordinary Minds.

Gardner writes that:

“Extraordinary individuals stand out in the extent to which they reflect—often explicitly—on the events of their lives, large as well as small.”  

Invest in your strengths

Understanding that I am a certain way — deeply curious, a multitasker, trusting and trustworthy, a voracious reader and strong communicator, disinterested in details or debugging code, endowed with fast twitch muscles, etc — set me up in a certain way.

And it’s my job to foster those strengths, patch up / negate weaknesses, and put myself in situations where my strengths will allow me to succeed. By the way, it’s hard to do that without reflection (unless you’re like an insanely intuitive person, but even then you’ll have blind spots).

Back to Gardner:

“Extraordinary individuals are distinguished less by their impressive ‘raw powers’ than by their ability to identify their strengths and then to exploit them.”

That’s the meta lesson here.

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Thank you, Jason!

Jason has been kind enough to put an exceptional amount of effort, detail, and reflection into this post. 

Connect with Jason: If you enjoyed this and found it helpful, please feel free to Tweet at him (and thank him), or subscribe to his newsletter, it’s quite fascinating. 

Twitter: @jasonshen 

Sign up for Cultivating Resilience and reply to a newsletter!

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