Navigating Silicon Valley: My Journey from Microsoft and Google to Startups and Beyond
How unexpected turns, tough lessons, and calculated risks shaped my career as a product leader
In a special episode of Fireside PM, I had the tables turned. My friend and longtime subscriber, Wes Woo, took over as interviewer, guiding me through my career journey. It was both fun and humbling to look back on decades of work, from the structured halls of Microsoft to the scrappy world of startups, and then to Google and YouTube and Google Health, where I was challenged to think and work in new ways. Here are some of the lessons I’ve picked up, and the advice I would share with today’s product managers looking to build meaningful, resilient careers.
Beginnings: An Unconventional Path to Product Management
I never had the classic Silicon Valley path. I grew up in New Jersey, the son of Chinese immigrants who had left everything behind after the civil war in China. My parents eventually made their way to the United States in search of opportunity, where I was born. Initially, I wasn’t headed for tech. I studied history and economics at Bowdoin College in Maine, and my first job out of college was actually in management consulting.
When I started in product management, I had neither a CS degree nor coding background. It was a different time, but even today, I think not having that technical training can be an asset. Product managers need to be “multi-lingual,” able to speak with engineers, designers, researchers, and business teams. I discovered that this broad focus on solving problems and communicating effectively would be the foundation of my career.
Microsoft: Finding My Way in Product
My first real foray into product management was at Microsoft, where I started in business development and quickly moved into product planning for MSN. Working at Microsoft taught me the importance of product sense and customer obsession, even if it didn’t always go smoothly. Early on, I was slated to join a project to build a social network leveraging the massive user base of Windows Messenger and MSN Messenger. But my role changed last-minute when Gmail launched, and Microsoft put all hands on deck to save Hotmail. “We had to reinvent Hotmail from the ground up,” I explained.
Through this experience, I learned that product success isn’t just about building what you think is cool. It’s about serving real, urgent customer needs. That project took years and taught me about everything from managing technical constraints to understanding user frustrations.
Stepping into Startups: The Roller Coaster Ride of Product-Market Fit
After my time at Microsoft, I was eager for the faster pace of a startup. My first startup role was with Trumba, a web 2.0 calendar company that was, frankly, way ahead of its time. The platform had some advanced features, like overlaying calendars and subscribing to shared calendars, but when Google Calendar launched for free, we struggled to compete.
The lessons here were some of the hardest and most valuable I’ve ever learned. Startups are like product experiments in real time, and they don’t always go the way you plan. “One thing I learned was that if you’re the product manager, you really have to believe in the product’s mission,” I shared. I tried to rally the team to pivot the company toward a different direction, but ultimately, the company chose another path that didn’t align with my vision. That’s when I realized the importance of conviction in product management. “If you’re a PM, you can’t drive a product without believing in it yourself. Conviction is everything.”
Marchex: Leadership and Learning to Walk Away
My next role took me to Marchex, where I led the product and design teams as the SVP of Product. The environment was totally different from Microsoft and Trumba, and I gained a whole new perspective on product strategy. Marchex was investing heavily in a pay-per-call ad network. But as I dug deeper, I began to question whether this strategy was solving a significant customer problem. “It’s tough to be the head of product when you’re not fully convinced of the product bet,” I shared with Wes.
At the same time, Marchex was a great place to grow as a leader and learn the complexities of managing cross-functional teams. But over time, I knew I wanted to build something new, something closer to my vision. This was a valuable lesson: you need conviction in your product, but you also need to know when to walk away and pursue what drives you.
Poachable: A Startup Roller Coaster
With my entrepreneurial itch growing, I co-founded a new startup called Poachable. The company went through two major pivots, many rounds of fundraising, and an eventual sale of IP, though we never reached full market fit. This was a true entrepreneurial journey, with all the highs and lows you’d expect. It was also a chance to put my product principles to the test, trying to find real product-market fit with limited resources and constant iteration.
“Poachable became a case study on pivots and resilience,” I told Wes. I was incredibly fortunate to have strong investor support, and we did raise several million in capital. But after a few years, I had to face the reality that the product didn’t have the traction we needed. We sold the company’s assets, but it was a humbling experience that reinforced the importance of grit, resilience, and a willingness to iterate even when things are tough.
Joining Google Again, This Time at YouTube
When Google came knocking again, I was ready for the opportunity to join YouTube in Zurich. My wife and I decided it was the right time for an adventure, so we moved our family to Switzerland. This was an entirely different experience from my earlier time at Google—both in terms of location and responsibility. I was part of the team responsible for YouTube’s creator experience, a challenging but deeply rewarding project. One of my proudest moments was working on the YouTube Analytics redesign, where we doubled creator business metrics and built a new set of tools that empowered creators to understand and grow their audiences.
“At YouTube, I learned that product management at scale is about thinking big while not losing sight of individual user needs,” I said. The experience taught me a lot about balancing creativity with data-driven insights, as well as the importance of accessibility in tech. We were developing features that needed to serve a diverse, global audience, and that required a level of adaptability I hadn’t experienced before.
Google Health: Meaningful Impact and Product Complexity
After YouTube, I joined Google Health, where I led clinical product development. Google Health felt like a culmination of everything I’d learned—balancing user needs, adapting to regulatory constraints, and solving for complex workflows. Working on health products meant dealing with incredibly sensitive data and navigating a heavily regulated environment. But it also brought a renewed sense of purpose to my work.
“Healthcare is personal; the stakes are higher,” I explained. “At Google Health, I’m not just focused on optimizing metrics—I’m focused on helping people get better care.” This role forced me to develop new ways of thinking about impact, measurement, and trust. We had to consider patient safety, data privacy, and real-life clinical workflows in every decision we made. The challenge was enormous, but the potential for positive impact made it incredibly fulfilling.
Key Advice for Product Managers
When Wes asked what advice I would give to PMs today, I shared some of the lessons that have shaped my career. Here are a few that stand out:
Focus on Real Problems: “As product managers, we can get caught up in feature-building. But if you’re not solving a real customer pain point, the best-built product won’t matter,” I emphasized. This has been a recurring theme throughout my career, from Hotmail’s redesign to Google Health. Good products start with genuine, urgent customer needs.
Stay Curious and Flexible: I told Wes that “being adaptable is everything.” In product management, things rarely go exactly as planned, and it’s essential to stay open to different paths, even ones that may seem risky. The unexpected shifts often bring the most growth.
Build Meaningful Relationships: I’ve had many opportunities arise from former colleagues or friends who remembered how we worked together. You don’t have to be a “super networker” to succeed in product management. “Just do good work and treat people well, and those connections often come back to support you,” I shared.
Embrace Coaching or Mentorship: I believe in the value of coaching as a safe space to reflect and clarify goals. Whether you have a formal coach or a trusted mentor, taking time to reflect is essential. “It’s easy to get caught up in work, but giving yourself the space to think deeply about where you’re headed can be transformative.”
Measure Success Beyond Titles and Promotions: This is something I’ve only come to appreciate later in my career. A fulfilling career isn’t about the titles on your resume; it’s about the impact you make and the people you support. “Think about the legacy you want to leave, not just the position you want to attain.”
Looking Forward: Still Searching for That Big Win
As I shared with Wes, I’m still looking for my massive win—a product or initiative that fundamentally changes people’s lives in a big way. But over the years, I’ve learned that finding satisfaction in the journey, not just the end goal, is crucial. “I’d love to look back one day and know that I made historic impact, but I’m grateful for everything I’ve learned along the way.”
Reflecting on this journey reminds me that product management, like life, is rarely a straight path. It’s a journey shaped by unexpected turns, the people you meet, and the problems you choose to solve. Fireside PM is my way of sharing these stories, and I hope that they inspire you, whether you’re a PM just starting out or a seasoned product leader seeking your next big challenge.
Thanks for being part of the journey with me.
Join the Backchannel – My Maven Cohort for PMs
As I reflected on my journey with Wes, I realized that so much of my growth has come from learning alongside talented peers, mentors, and colleagues across tech. That’s why I created The Backchannel: Confidential PM Cohort on Maven. This 14-week program is designed for product managers who want to accelerate their careers, gain clarity on their growth path, and tackle real-world product challenges within a small, curated peer group.
In The Backchannel, we go beyond theory. Every week, you’ll work through real product challenges brought by your peers or yourself. We’ll focus on confident decision-making, career clarity, and honing leadership skills in a safe, collaborative environment. You’ll get hands-on practice navigating difficult decisions, managing up and across teams, and leading with influence—essential skills I’ve learned firsthand at companies like Google and through my startup experiences.
If you’re a product manager at the L4 to L7 level and ready to level up your impact, join us. The cohort is filling quickly, and there are only a few days left to apply. You’ll leave with actionable strategies, a network of PMs across diverse tech backgrounds, and the tools to tackle complex product challenges confidently.
Head to The Backchannel: Confidential PM Cohort on Maven to apply.