WeddingWire Founder, Timothy Chi, Reveals Faux Pas While Pitching Martha Stewart

WeddingWire Founder/CEO, Timothy Chi, discusses his great big global chapter.  June, 2015 #Connectpreneur

WeddingWire Founder/CEO, Timothy Chi, discusses his great big global chapter. June, 2015 #Connectpreneur

The idea for Timothy Chi’s second company, WeddingWire, was borne of painful experience: Helping to plan his own wedding.  There were magazines that educated and inspired, but none that made it easier to execute sales, orders, and arrangements online.  Tim would have appreciated not flying so frequently between his U.S. home in Boston and the wedding venue in Toronto, Canada.

He was featured in a chat with @TienWong at #Connectpreneuer, Summer 2015 edition.

Focus: WeddingWire’s early years and what’s next besides a strong leap into 14 additional countries, with recent acquisitions in Spain and Portugal.


  • Faux pas while pitching Martha Stewart for Series A funding.
  • And an instructive accounting of a major mistake Tim recalls from early startup days.
  • Spotlight on 5 recent acquisitions and partnering opportunities that come with global growth.

What is WeddingWire?

WeddingWire is a vertical marketplace that’s focused on the wedding space.  Tim is a Founder.  This technology platform is similar to other successful models (Yelp, Zillow) because it sells subscriptions to connect customers to current, well-recommended wedding event resources, from the planning couple’s perspective.  WeddingWire crowdsources reviews of current wedding industry vendors by city.  The fast-growing startup is now one of the largest site’s in the U.S., and just expanded globally in 14 countries.  Tim says about his model:

We’re primarily an ad-driven business.  Eighty-five percent of our revenue comes from photographers, venues, florists, that are subscribing to our platform in exchange for what they expect – the door swings, the phone rings, orders come in online…

Tim really talks like this.  He grew up in Corona Del Mar, CA.

Tim told us:

  • Weddings are a high-risk, high emotion purchase, average $25,000-$30,000.
  • WeddingWire helps couples make better purchase decisions.
  • The market is tremendous – Here’s an idea how big a portion of it WeddingWire commands: There’s 2 million weddings in the U.S., average spend is $25,000.  Of this $50 billion spend, about half use WeddingWire.
  • The one-shot nature and high referral rate of this dominant business in the space result in vendors choosing to advertise each year.
  • Loyalty in this industry comes in the form of referrals that drive future business.

Built, hire, start

Early in 2007, the path to building WeddingWire began with one critical step:  Asking his wife (who he had followed to Boston for her last two years of grad school) if he and his early team could put their desks in their home living room .)

We started hammering away on our sales and marketing process.  We said we’ll build a minimum viable product (MVP) and launch in DC, weddings get planned locally so city by city expansion makes sense.

1.) First financing round, family & friends, $1/2 million. 2.) One year later, the firm entered the traditional VC landscape while talking with a lot of media companies in the wedding space about a strategic partnership. That’s when Lee, Wedding Wire’s COO at the time, did some business development 101 using an early release of LinkedIn researched potential partnerships online and sent cold call emails.  The company began a commercial agreement to sell through a commercial arrangement with the Martha Stewart brand:

After the deal, when I called for WeddingWire, I said ‘This is Tim Chi calling from Martha Steward Wedding Wire, and they were like ‘Oh, Martha’s calling me, I’ll hang on the phone for this one.’ And this was a great way for us to start as partners growing our brand.

Subsequently, the startup raised $25 million from Spectrum Venture Capital in Boston, a San Francisco-based VC in September 2012.  Total capital raise about $33 million.  “We’re really capital efficient,” Tim says, “We turned capital positive in 2011 so we’re growing really fast and still focused on growth.”  Look for acquisitions and rapid growth ahead.

But first, they had the chance to pitch Martha Stewart.  Tim says what happened that day was embarrassing.  At one point, he was pitching for a commercial relationship to sell through Martha Stewart Wedding  Lunch arrived.  We were at a studio where she shot a show, so we agreed to a working lunch.   As we pitched, Martha got up and started tossing the salad and getting lunch ready to be served.

After the pitch, I kept talking, arms flailing, served myself some lunch.

At one point, Martha Stewart looks over at me and asks, ‘Tim, why did you use your dessert plate for your entree?

He looked down at a plate piled vertically, quiche, salad on top.

On the heels of this mildly self-deprecating story, I asked him what was the worst mistake he’d made — in business.  Tim thought the Martha Stewart plate faux pas could have been the worst if he’d lost the company millions in Series A funding.  But, he hadn’t.  Tim has people skills that contribute to making him adorable.  [He likes reading about what motivates people to do what they do.  He mentioned the book #Nudge, which should definitely seek out his cover review soundbyte for the quality paperback reprint.]

In vertical marketplaces like YELP, winner takes all.  Scale begets more scale.  It’s hard to catch up to four million reviews.  Timothy Chi says:

If you can get scale, you build a moat around your business.

WeddingWire Founder/CEO, Timothy Chi, was a featured guest of Tien Wong (pictured elsewhere.)

WeddingWire Founder/CEO, Timothy Chi, was a featured guest @TienWong #Connectpreneur

Then, the biggest challenge is keeping your feet dry as you step in it from time to time.

Recent growth continues to be opportunistic, building on four or five acquisitions so far, including ones in Spain and Portugal.  The company just acquired Arlington-based Gay

WeddingWire looks for three things in an acquisition:

  1. Technology
  2. Talent,
  3. Target Adjustable Market.

Tim’s top biggest business mistakes

The early Wedding wire launch deployed “a mistake but also an opportunity as well,” Tim explained:

We had a very technology purist view on how people were going to pay us; how other merchants were going to interact with our system. We spent a ton of energy and resources developing this whole pay per lead system for small businesses.  Adwords had just come out, people should not have to buy advertising and not get what they want.  What happens if your lead doesn’t get purchased, recycle it and make the right match.  We called it Smartmatch technology.  We released it and people didn’t understand what we were trying to do — we spent a good amount of energy doing that.

“How do people want to buy?  It’s a really interesting question.”

But, nobody was interested enough to buy what they were selling.

WeddingWire, seems to have no problem attracting subscribers, vendors, and engaged couples and their families and friends who refer future customers to its platform.  At about 400 employees and growing fast, the concern is how to keep the culture  entrepreneurial, fun, and energetic.  Here’s his secret to hiring well:

We look for really talented people and good leaders, we don’t just screen for job-specific functions.  I like to think if I were on a four-hour layover, would I want to talk with him?

Tim’s fun.  He found the right business and model.

Tien Wong creates and maintains a community to connect  local business leaders, startups, investors, and accomplished speakers: #Connectpreneur summer edition, 2015

Tien Wong creates and maintains a community to connect local business leaders, startups, investors, and accomplished speakers: #Connectpreneur summer edition, 2015

About Janice K. Mandel

I'm a storyteller engaged in the evolving voice tech community. Early adopter experience in New York City included: Sr. Editor, EIC/Intelligence, the first online, commercial database (1980s); Communications/Voice of, like Zillow but in 1999; and Reach networks -- like Mosaic, only four years sooner. I've recruited speakers for VOICE Summit ( and contributed regularly to its "flashbriefing" on Alexa leading up to the event.
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