Timothy Chi on Creating the Largest Wedding Marketplace


DC couples – and singles – are no strangers to the cool blue branding of The Wedding Wire, but how many of you know the founder Timothy Chi? That’s right, a groom, not a bride, that was so taken by the wedding planning process he decided to start a technology company to disrupt wedding planning and making it one of the world's largest wedding marketplaces. In fact, The Wedding Wire was started by not one, but four guys together in Timothy’s Chevy Chase living room. The Wedding Wire is now valued at over $750 million, and Startup Grind DC couldn’t wait to chat with Timothy.


Like many other Startup Grind guests, Timothy was raised by immigrants. Both of his parents were entreprenuers; His father an architect, his mother a real estate broker. His own first business was far less glamorous: A car wash. It wasn’t until college, as a student at Cornell University, where he found his calling in software engineering.


Growing the Blackboard, LLC Beast


Way before Wedding Wire, Timothy was a known success for cofounding Blackboard. Back at Cornell, he had been working with six other founders, skipping classes to hack out the code that would be the backbone of the education software monolith. But how did his startup end up in DC under the Michael Chasen brand “Blackboard”?


Apparently the seven students didn’t need much convincing to ditch Ithaca, New York for Washington, DC, where the city’s twenty-something fueled intellectual renaissance and northern Virginia’s tech boom, was making it the area the place to be. “They [Blackboard] brought to the table a very valuable and defined set of skills and funding that they had lined up,” Timothy explained more practically. “We on the other hand, were graduating, had a product and a couple customers, and it just kind of made sense that together we completed the whole pie.”


Startups: Built to Last, or Built to Sell?


“We went public in ‘O4, and I left in 2005,” said Chi, before cracking a smile. “That leads to my next question,” responded Brian our Startup Grind host. “For entrepreneurs, is that a good mentality, ‘I want to build the next Fortune 500 company’, or ‘I just want the lower hanging fruit’…getting it to a point I can sell it.”


“I don’t know I have a strong viewpoint on what’s ‘better’,” said Timothy. “I know for me, history for me, I’m much more interested in building a businesses that there’s a reason behind it, it’s not a quick flip. But that’s for me. I’m sure you can point to plenty of examples of people who have been very successful doing it the other way. So I don’t know if it’s a question of ‘better’, just what you’re designed to do.


On to the Next One: Building Wedding Wire


Wedding Wire’s main business is serving as a marketplace for “SMBs”, small businesses. The site serves 144,000 vendors in addition to all the bridal customers. “Groupon, Living Social, they’re all trying to figure out how to crack the nut with the SMBs,” said Brian. “If you look at popular, what I call vertical marketplaces in the industry,” began Timothy. “So this would be Trip Advisor, Angie’s List, you even throw Uber, AirBnB  - particularly the verticals, real estate, healthcare, any marketplace business – what they did really well is they didn’t try to sign up every SMB in the domestic market.”


“They purpose built a solution for their vertical.” Timothy got excited here, “One of the things we think we do really well, is we hope we’re a great revenue generator for all wedding merchants across the U.S., where we’re sending brides to their websites, and you know ‘door swings and phone rings’. We’ve also deployed a whole platform of SaaS tools: CRM, bill payment collection, client extranets, social media monitoring. Not just the off-the-shelf stuff you would get: Take Salesforce and repurpose it. It is all purpose built for the direct for the direct needs of our SMBs.”