10 Questions with Michael - How can Fintech innovation help us create a more sustainable world?
Use with permission of Michael Wu
I interviewed tech entrepreneur and software engineer of Stripe, Michael Wu, to understand how his experience in entrepreneurship and software development has shaped his perspective about the world. He discusses some of his self-reflections, insights, and what are the advice he can give aspiring tech entrepreneurs of today.
Hello Michael! And thank you for accepting this week’s interview! To start, could you share with our readers a little bit about who you are, and the kinds of work you do for Stripe?
I’m a software engineer at Stripe, based out of Tokyo. I’m originally from the San Francisco Bay Area, California, but moved last year to Tokyo, right as COVID was happening. I have a startup background, having helped found my own, Pixelapse, right out of graduate school, which was acquired by Dropbox, then a brief stint at Gem, before ending up in Tokyo.
For Stripe, I’m part of the Japan product team, meaning we own the whole customer experience here in Japan, which is mainly developing payment method integrations. Other than work, I am a moderator and co-host of the Facebook community and podcast Badass Asian Dudes, a co-blogger at DEM Flyers, am involved heavily with the Asian-American community, an avid traveler, cook, and fitness lover.
What inspired you to pursue this position?
My mom was a software engineer at HP and then at Cisco, while my dad was a VP of Engineering at Xilinx. So I grew up in a fairly technical environment, and had a lot of educational resources such as encyclopedias as well access to the internet and computers at an early age. Seeing the role models of my parents as well as playing around with creating my own programs starting in 4th grade developed my love of creating useful programs for people. I helped run a widely used high school website in high school and was a website builder at a student agency in college.
When I started college in 2006 at Princeton, I already knew I wanted to be a programmer, though I didn't know how impactful software would be on the wider world yet. I grew up through the tech bubble and crash of the 90s, and even as I went through high school and college in the 2000s, tech as a career was still in recovery. Biotech was the other hot career path for people my age, though that turned out to not be as hot. But I was good at programming and enjoyed it, so I thought I would try to make that a career.
How did the ideas of software engineering shaped your current perspectives of social development?
I don’t know how to answer this question. It’s clear that technology has had and will continue to have a massive impact on all our lives. It has made our lives more convenient and made access to many previously inaccessible services available to many more people for cheap. It has created markets and positive economic benefits where none existed before. Working in fintech, it’s amazing how the seemingly simple act of providing incrementally better financial services is both extremely lucrative as well as extremely beneficial to wide swaths of people.
There are a few dark sides to technology though - one is thinking that tech is the solution to all problems, removing the human element from service. Yes, automate as many tough tasks away as you can, but strive to maintain human empathy. This is seen by how many companies make it impossible for you to contact a human for service. Service should be augmented to be better by technology, not diminished. Another problem - attempting to massively scale by racing to the bottom and mistreating your workers as well as squashing local services that weren’t problematic and were a part of healthy communities - see Amazon, Uber, etc.
The last one I will name is developing products that are unhealthy for consumers in various ways, that trick their brains for attention and money such as various social networks, addictive games with microtransactions. Despite all the connections that social media has enabled - I run or participate in several online communities that I have found immensely valuable, it also can rewire brains to crave novelty and attention in unhealthy ways. Not everyone has the mental fortitude to have a healthy relationship with technology - this is why regulations, and the technology companies have to step in to ensure the health of their users.
Are there any personality traits or habits you think every leader should have?
Proactiveness and ownership. Trusting others. Empathy. Good listening skills.
Whose career inspires you, and why? Who do you admire?
I have to think about this one. I often don’t remember what the career paths of others are besides the super famous ones.
I admire the old school programmers that made an impact on the world, such as Brian Kernighan, the author of a very famous C programming language book, and one of my computer science professors at Princeton. I admire several Asian American start-up founders who struggled and fought their way to the top. I admire the co-founders of Stripe, Patrick and John Collison, some very brilliant brothers making a huge impact in the tech world.
What are some of the major challenges you face in your career? And what keeps you motivated to solve them instead of quitting?
I graduated from Princeton in 2010, and at that point I felt like I wanted to continue the college environment. I was an Electrical Engineering major with a certificate in Computer Science, and I felt like I was missing out on several advanced level Computer Science classes that I could make up in graduate school. At that point as well, the world was still recovering from the Great Recession, and I figured a year or two at graduate school would be nice while waiting for the job market in tech to recover.
I applied everywhere as a masters student, but a family friend encouraged me to go for a PhD, and also a professor at Stanford reached out who was impressed by my background and encouraged me to convert over to the PhD program. I figured I could give it an honest try, and worst case I would have a Master’s paid for. So I converted over to the PhD program and started working in that professor’s lab. I even studied for and passed the qualifying exams, which is really difficult in the Electrical Engineering program there.
Unfortunately I quickly found out I did not like the world of academic software, which was focused on publishing papers. This resulted in very unusable software that was mainly written to prove some point for publishing. I was very frustrated with this and eventually decided to leave with a Master’s and join my friend’s start-up. My friends had just gotten out of YCombinator class of Winter 2012, and were looking for additional help on Pixelapse, a version control tool for designers. We were all engineers, though one was more business focused and one was more product / design focused.
The initial period was great, we released to some fanfare and had plenty of free users signed up. However, we were terrible at sales and marketing, so even if people loved our product, when we tried to get people to pay, not that many converted over to paid plans. We continued with the start-up for almost 3 years with limited financial growth. Nearing the end of that, as an employee and not a founder, I was frustrated with our progress and future potential of the company, and almost quit before finding out we were in the middle of an acquisition process with Dropbox. Obviously at that point I stayed and then was at Dropbox for almost 4 years after that!
Being in between jobs while searching for a job in Japan. That was one of the toughest moments of my life, and there were points where I lost all confidence in myself. I found stability in a temporary gig at my friend’s start-up, stayed in Japan for a month to reassure myself that it was the correct decision, and went 100% in on interviewing.
I don’t think quitting is necessarily bad though, if you gave things a good shot to see what the potential was. They say the best entrepreneurs iterate fast - they drop bad ideas quickly if they prove to fundamentally not work.
If you were to start all over again, would you have done anything differently?
My path ended up turning out great, but if I could do it again, I would have tried to get more varied experiences at fast growing companies at the beginning of my career. I would also make sure to keep myself from getting too comfortable and stagnant at whatever position I’m in. I would have also repositioned myself at a company that had a Japan office a few years before I wanted to move so I didn’t have to wholesale leave and find a new one.
If you weren’t working for Stripe, what career would you like to explore?
I would be running pop-up restaurants as I globe-trot the world, while my investments grow in the background.
“If you are really solving people’s problems, they are way more willing to pay than you think.”
What advice do you have for youths who also aspire to work in the field of tech entrepreneurship and software engineering?
Find projects that you are passionate about doing. This could be websites or apps you are writing for yourself or others. This could be getting involved in open-source projects. This builds up your own passion while giving you valuable experience and skills. For entrepreneurship, while you are still young is the best time to try, fail, try again at businesses. What you lose is relatively small while you have few assets and don’t have a family to support, while what you could gain is huge.
Leverage something that you have experience in and go out and talk to potential customers to see what their problems are and if you can solve them with your skills. Don’t just build products in a bubble and hope people will use them. Go out and find out what people’s problems are and sell them on your solution, even if you haven’t quite built one yet. This is one of the best ways to find product market fit. And remember, if you are really solving people’s problems, they are way more willing to pay than you think.
What’s next for Michael?
After I’ve had my fill of living in Japan exclusively, I plan to go Pan-Pacific: spend time in Korea, Taiwan, while traveling to other Asian countries and the West Coast USA often. I’m closed to becoming work-optional or at least being very selective in the work I want to do, and I’m still figuring out the path that will let me do that. Likely it will be a combination of doing my own thing and investing.
I’ve already started going down the angel investing path - We’ll see where that goes