Ten Question Interview Series: Technology – How can Fintech innovation help us create a more sustainable world?

I interviewed Michael Wu, tech entrepreneur and software engineer for Stripe, to understand how his experience in entrepreneurship and software development has shaped his perspective about the world. He discusses some of his reflections, insights, and advice to the aspiring tech entrepreneurs of today. 

Use with permission of Michael Wu

Hello, Michael! 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 start-up background, having helped found my own, Pixelapse, right out of graduate school, which was acquired by Dropbox. Then after a brief stint at Gem, I ended 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 for 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 as 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 fourth 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 was not 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 shape 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 of our lives. It has made our lives more convenient and made access to many previously inaccessible services available to many more people. 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 some dark sides to technology though; one is thinking that tech is the solution to all problems and removing the human element from service. Yes, automate as many tough tasks 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 made better by technology not diminished. Another problem is attempting to massively scale up by racing to the bottom and mistreating your workers as well as squashing local services that weren’t problematic and were actually 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 or that trick their brains for attention and money, such as various social networks or 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 policy regulations and 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.

Michael participating in a charity dinner organized by The Asian Hustle Network and the #Hateisavirus movement to speak out against Asian hate.

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 beside 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 some Asian-American startup founders who struggled and fought their way to the top.

I admire the co-founders of Stripe, Patrick and John Collison, two 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 in 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 master’s student, but a family friend encouraged me to go for a Ph.D. Also, a professor at Stanford, who was impressed by my background, reached out and encouraged me to convert to the Ph.D. program. I figured I could give it an honest try, and, worst case, I would have a master’s paid for. So I converted to the Ph.D. 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, which 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 friends’ startup. My friends had just gotten out of the Y Combinator class of winter 2012 and were looking for additional help with Pixelapse, a version control tool for designers. We were all engineers though one was more business-focused and one was more product or design-focused.

The initial period was great; we released 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,  not that many converted over to paid plans when we tried to get people to pay. We continued with the startup for almost three years with limited financial growth. Nearing the end of that as an employee and not a founder, I was frustrated with our progress and the company’s future potential 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 four years after that.

Being in between jobs while searching for a job in Japan 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 friends’ 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 fundamentally to not work.

If you were to start all over again, would you do 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 actually wanted to move, so I didn’t have to leave wholesale 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-trotted while my investments were growing in the background.

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 and try again at businesses. What you lose is relatively small while you have few assets and don’t have a family to support, and 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 and find out what people’s problems are and sell them on your solutions, even if you haven’t quite built them 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.

And remember, if you are really solving people’s problems, they are way more willing to pay than you think. – Michael Wu

What’s next for Michael?

After I’ve had my fill of living in Japan exclusively, I plan to go, Pan Pacific, to spend time in Korea and Taiwan while traveling to other Asian countries and often to the West Coast of the U.S. I’m close 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.

Links to Michael’s travel blog on “Moving to Japan during a pandemic” are provided here:

Part I
Part II

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