Co-Founder of Shimmer (YC S21)

Jon Wang

Jon Wang, Shimmer's former COO, innovates in mental health with a data-driven focus, leveraging his diverse background and values.

Jon Wang is the co-founder and former COO of Shimmer (YC S21). Shimmer is a seed-funded mental health startup backed by Y-Combinator, Blackstone Launchpad, Techstars, and more. He’s also a founding member of MD++, a network of over 1500 physician-innovators. Jon graduated from Stanford in 2019 with a degree in Biomedical Informatics. After college, he started medical school at UCSF before dropping out to work on Shimmer full-time.

In today’s issue, Jon shares his experience with YC, mental health in the startup world, and defining his values:

✨ What is Shimmer? Shimmer is an online mental health platform offering support groups led by peer coaches. The platform allows members to gratitude journal, mood track, set goals, and engage in video sessions and community events.

🏠 Growing up: I've always been interested in healthcare and technology, in part because my dad was a doctor and my mom was a statistician. My first exposure to entrepreneurship was in high school, where we filled balloons with water and cornstarch and sold them as stressballs. I always knew innovation would be in my career in some way, it was just a matter of how.

🌱 Starting Shimmer: During COVID, two of my close friends developed severe mental health issues. I realized I was learning a lot of information in medical school, but not doing anything with it. As a doctor, I would always be limited by the number of people I could touch. I decided to leave medical school, get two cofounders, and start Shimmer.

📚 Dropping out of med school: I was just chasing what gave me energy. One week, Shimmer took up 20% of my time. The next week, it was 40% of the time. Then eventually, I was spending 95% of my time thinking and working on the startup and 5% cramming everything I could the night before the exam. At that point, I was like, might as well just leave medical school rather than scrape by doing the bare minimum.

⏭ Passing up an opportunity: My first opportunity to go full-time on something was junior year of college. There's a class at Stanford called Lean Launchpad where you come in with an idea and come out a startup. Two people on my team actually left school to work on that full-time and just raised their Series A. It’s called XP Health, which is a tech-enabled vision benefits platform.

I decided not to go. When you work on a startup, it's like a twelve year dedication to one problem space. I wasn’t sure if I was particularly passionate about it. I also felt like I didn't understand enough about healthcare or technology to leave school. Even now, I'm still trying to figure out what brings me passion.

🤕 Startups & mental health: Founder mental health is a huge issue and not talked about enough. We actually almost pivoted and worked on an idea offering mental health support just for founders. But at the end of the day, as a founder, it's really hard not to have large amounts of stress because there's so many important things that you're constantly thinking about. If you don't feel it, then it's really hard to get things done. You have employees who are relying on you. You're the roadblock for every single thing. Being a founder is not for everyone. I even question it for myself sometimes.

At Shimmer, we really tried hard to create a culture around mental health. Every week, we would go through a reflection prompt or a spotlight where everyone shares something about their mental health story. Trying to normalize mental health in the workplace was really effective. People not only can connect more on a personal level, but they felt more comfortable bringing their full selves to work. There's a good book on founder mental health called Burn Rate by Andy Duun (the founder of Bonobos).

💼 On building a team: Hire lines, not dots. It's kind of a weird phrase, but you want to hire the candidate with higher growth potential even if their current state is worse than another candidate’s. Someone who's really hungry and cares about the mission is going to be a much better candidate than someone experienced but only working to make money.

🍊 Y-Combinator’s best takeaway: It teaches you a lot about being in the mindset of a founder. They really ingrain in you the need to move fast, get things done, and run through walls.

👎 Drawbacks of YC: For one, each partner is talking to a ton of companies each, so they don't have the time to fully understand what you're doing. You're kind of on your own still.Second, they have a really strong focus on growth. They're like, grow, grow, grow, or die. I don't think that's necessarily the best approach for companies still looking for product market fit, which we were. YC asked us to track metrics around growth and rigorously follow them when in reality, metrics around product market fit were more important. That really messes up your mentality when you're still iterating to find a product that works.

📝 Tips for the YC application: Get your one liner down, clear and concise. That's a really common early stage startup founder thing. A lot of people like to say stuff like having a “world class algorithm” or “state of the art” technology. No one likes that language. The most boring things can be really great ideas, and YC knows that.

❌ Getting rejected before accepted: We applied to YC twice and got rejected the first time. I think that’s the case for most founders in YC. The feedback we got from our first application was 1) you need to understand your users better, 2) you need to get paying customers and 3) drop out of school. We did all three of those things and got accepted the second time around.

💭 Defining your values: There's this really great Brené Brown exercise where you pick words that you resonate with out of a list. You bucket those words into categories. From there, you create sentences. That was an incredibly valuable exercise for me, even to this day, to make sure I’m on the right path when making decisions. My exact ones are 1) long-lasting & meaningful work that touches the lives of many people in ways that empower and help them that I contributed significantly towards, and 2) being a whole, loving, kind, & intellectual presence in this world.

📖 A must-read: Everyone should read Almanack of Naval Ravikant (founder of AngelList). I’d also recommend this article by Paul Graham called How to Do What You Love.

🛣️ Best advice for choosing a career path: Try orthogonal things and eventually, you'll discover what you're truly passionate about. In my experience, I tried to become a doctor and realized it wasn’t right for me. Arguably, going to medical school was an inefficient use of my time, but I don’t regret it at all. In the early stages of your career, if you're only going down one straight path, then you’ll only ever see that one path. There’s a good framework of spending one to two years heads down working hard, then picking your head back up and doing intense reflection about where you want to go moving forward.

tl;dr 1) Working on a startup is a multi-year dedication to one problem space, so you should be passionate about what you’re building, 2) The best startups are the ones that can clearly and concisely communicate their value proposition, and 3) Being a founder can take up your entire headspace, and it may not be for everyone, and 4) Do things that are different and independent of one another to determine what it is you truly want to do.

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