Did you intend to become an entrepreneur when you started at Cornell?

No. In fact, I thought I wanted to become a doctor until I scrubbed in for an open-heart surgery. So, I turned to Engineering because…well, candidly, I’m not sure. So, how did I end up as an entrepreneur?

Reflecting back, my parents emigrated from Taiwan in the 1970s and were entrepreneurs and small business owners. My dad was an architect and mom was a real estate broker. At a very young age, I got to see firsthand how hard it was to grow a small business. Sometimes, we’d go into the office on weekends to clean. I spent my afternoons after school at their office, drawing on my father’s drafting board while waiting for the work day to end before we could go home. I was their first IT person in high school, trying to figure out how to use AppleTalk to get their Macintoshes to see each other on the local network and share the same printer. 

Following their footsteps, I started my first business, a car wash, when I was still in high school – but it failed. We bought all the equipment, and no one showed up. I learned a valuable lesson early on – just because you’re good at something doesn’t mean it’s a good business, or that the rest of the world will believe in it. Attention to marketing, sales and customer targeting matters.

I brought this learning with me to Cornell. I had the great fortune of meeting a bunch of my closest friends during freshman orientation at Cornell. We spent the next four years together and started a business while on campus called CourseInfo (one of the earliest versions of online/virtual learning platforms). Looking back on that experience, what is remarkable to me was just how fortunate we were to have a bunch of like-minded Cornellians, from different disciplines, who loved to work together—but more importantly, hang out together.  For me, this was the embodiment of why culture in companies is important today. Among Dan Cane ’98, Stephen Gilfus ’97, Lee Wang ’97, Stephano Kim ’98, John Yang ’98 and John Knight ’98, we had product, engineering, finance, sales and marketing and it was an exhilarating time to be on campus, building something special.

When we graduated from Cornell, we moved down to Washington D.C. and formally launched Blackboard after merging with another local education company, and ultimately, had a great run building a leading global educational technology company which we took public in June 2004.

Credit: Provided

Entrepreneurship is all about taking calculated risks. What’s the most pivotal risk you’ve taken, and how did it change your path?

A pivotal moment for me was when I left Blackboard to start WeddingWire. It was a big risk, surrendering security for possibility. Part of what improved my ability to take a risk was that my wife, Tracey, could be the breadwinner for our newlywed life and provide financial stability as I took a leap of faith on this idea called WeddingWire. Furthermore, I didn’t ask my co-founders to commit 100% to WeddingWire at the time, because I didn’t know if it was going to work. We agreed that they could keep their day jobs, and we grinded together on nights and weekends from my living room. It was not until we secured our initial funding round that everyone came over full time. The benefit of this approach was that it enabled everyone to bear more risk early on. The reason that it worked was that each of my co-founders showed up every night and weekend with the passion and commitment of a founder. We were hustling. None of us took a salary for over a year. I chose the name WeddingWire because it was the only domain I could afford! Eventually, the risk paid off. We were able to secure funding, turn cash flow positive early on in our life cycle and continue to scale the company from there.  

How has your experience at Cornell impacted how you approach business?

The cold winters of Ithaca and sludging through whatever muddy, icy sidewalks to get to class at 8 a.m. with frozen hair reminds me that grit and determination are non-negotiables in building a business. We all know that there are ups and downs in business. For me, how you show up when things are down tells you a lot about yourself. Yes, it’s easier to stay in bed and do stuff online, but that doesn’t mean you should.

Was there a particular faculty member or class that influenced you the most? If so, how?

I really wish I had paid more attention in my psychology classes. Today, with over 2,000 team members split across multiple countries and time zones, I find that my job has really shifted to creating alignment, clarity, accountability and motivation throughout the organization to ensure that the company is moving fast in service of our couples and wedding professionals. One of the best ways to accomplish this is to have a leadership team that is constantly drawing out the best in each of our team members. They do this by being great mentors, coaches, and helping each of our team members realize the potential that we hired them for.  

What has been your proudest moment as an entrepreneur? Why?

One of my most proud moments is partnering with the hundreds of thousands of small businesses that are the fabric of the wedding industry. They help millions of engaged couples around the world find the “magic in the mayhem.” It is extremely rewarding to see our wedding professionals grow their businesses, expand their offerings and be successful in innovating and creating once-in-a-lifetime experiences for their customers. I’m grateful that we get to play a role in helping these bold and passionate entrepreneurs, who are dedicated to their craft, be more successful businesses while doing what they were born to do. I saw firsthand how difficult it can be to be a small business, and we at The Knot Worldwide will continue to invest behind all of our wedding professionals to help them grow.

If you had one piece of advice for someone just starting out, what would it be?

Someone once said, “The bottleneck is always at the top of the bottle.” One of the things I think is how to not be the bottleneck in growing our business. Sometimes this shows up at making fast decisions. Most of the time, this shows up by having a great team surrounding you that is highly aligned, high on trust and fully empowered to run fast. I was so fortunate to have this experience in both Blackboard and WeddingWire, with a larger co-founding team where we had that special dynamic. It amplified our creativity, velocity, speed to market and ultimately, growth prospects. Today, I’m exceedingly lucky to work with an incredibly talented team of leaders, which also includes many Cornellians (CFO Andy Ivanovich ’08, CPO Zohar Yardeni ’95, SVP Product Nikita Miller ’09 and many more!) My advice—always be thinking about how to drive alignment, empowerment, accountability, and don’t be that bottleneck.  

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