Tim Chi on Lessons from Entrepreneurship

Tim Chi is the Chief Executive Officer of The Knot Worldwide. After getting married in 2005, Tim set out to make wedding planning less stressful and frustrating. Together with his co-founders Jeff, Lee and Sonny, they threw four desks into his empty living room in Chevy Chase, Maryland and created WeddingWire, which became a leading global vendor marketplace serving the wedding industry, helping millions of engaged couples plan, execute and celebrate the most important day of their lives. WeddingWire grew to 1,000 employees worldwide and owned leading wedding brands in North America, Europe, South America and India. In 2019, Tim became CEO of The Knot Worldwide following the merger of XO Group Inc. (parent company of The Knot) and WeddingWire Inc. Previously, Tim co-founded Blackboard Inc. in 1998. While at Blackboard, Tim pioneered many of Blackboard’s flagship products and strategic initiatives, bringing technology into the classrooms of colleges, universities and school districts across the world. During his tenure, the company raised over $100 million in capital and was taken public on the Nasdaq in 2004.

Tim holds a B.S. in operations research and industrial engineering from Cornell University and an M.S. in engineering management from Tufts University. He resides in Maryland with his family and is based out of The Knot Worldwide’s Chevy Chase headquarters.

 

Tim had a number of amazing insights during our conversation. Some of them include:

“I actually do try to separate the idea of video game time from screen time” (7:20).

“Video gaming time [for my kids] is generally done with me” (7:30).

“We’re trying to create an intentional balance around exposing [our kids] to different things” (10:35).

“A lot of dedicated athletes do really well in any occupation I think because of that discipline and because of the team winning mentality” (12:10).

“I just know I’m not good at a lot of things” (13:25).

“In order to really excel, you need to have complementary skillsets at the table” (13:35).

“My chance of success is much improved if I’m working with partners” (14:05).

“Everything starts with relationships because that’s where trust gets built” (14:35).

“I tend not to take up as much headspace thinking about things that I’m not an expert in or I can’t connect with” (21:20).

“Disruption is natural” (22:15).

“Everybody has really good ideas, the difference is entrepreneurs do something about it; they’re willing to take a risk” (22:25).

“I like to think of myself as a realist with slightly rose-colored glasses on everything” (35:20).

“Video gaming is one of my escapes” (36:05)

“Everybody is entitled to make mistakes. It really is what did you learn from it?” (37:30).

“We know people are going to move on [from our company] and that life circumstances change. But what would be great is if people that left here said ‘I learned something, I took something away that helped me move to that next thing…’ That to me is success” (42:30).

“The how and when you implement it, those tend to have to get pessimized a lot” (47:30).

“I’m sort of just generally bullish on the idea that access to information and knowledge is a good thing for the world” (52:30).

“Start with a problem statement. What are we trying to solve here?” (56:00).

“Culture sits there as a broad-based thing, norms are how it shows up daily” (59:10).

“I do try to be very self-reflective about things and just in my own mental model always learning” (1:01:05).

“My personal development has really come from other people who I trust who I’ve built relationships with pushing me forward” (1:02:30).

 

Additionally, you can connect with Tim himself on LinkedIn here, and also follow The Knot Worldwide on LinkedIn here.

Thank you so much to Tim for coming on the podcast!

I wrote a book called “Shift Your Mind” that was released in October of 2020, and you can order it on Amazon and Barnes and Noble. Additionally, I have launched a company called Strong Skills, and I encourage you to check out our new website https://www.strongskills.co/. If you liked this episode and/or any others, please follow me on Twitter: @brianlevenson or Instagram: @Intentional_Performers.

Thanks for listening.