He Scored $175,000 By Saying the One Phrase This Investor Wanted to Hear

Matt Williamson, founder of second home co-ownership platform Plum, describes his strategy for winning big on 'Elevator Pitch.'

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By Entrepreneur Staff

Matt Williamson

Entrepreneur Elevator Pitch is the show where contestants get into an elevator and have just 60 seconds to pitch their business to a video camera. Our board of investors is watching, and if they like what they hear they open the doors and the entrepreneur steps into the boardroom to try to seal the deal. If they don't like what they hear, the entrepreneur gets sent back down.

In this ongoing article series, we're celebrating the entrepreneurs who walked into the boardroom and came out with a win and sharing their tips for pitching success.

Who are you and what is your business?

I'm Matt Williamson, a serial entrepreneur, husband of 22 years, father to two great teens and snuggler of a lovable pit-Weiler rescue pup named Pete. My company Plum makes it easy for people to form groups to buy vacation homes together. By sharing the upfront costs and the ongoing maintenance, millions more people can enjoy the wealth-building and convenience of a second home.

How did you prepare for the show?

I feel like pitch contests like these are binary. You're either all-in to win it, or you shouldn't bother. There's no middle ground.

First thing is to identify what winning looks like. Watch the prior videos. Take notes on the following sections: winners, losers, judges, format and observations.

I watched every video from the first seven seasons, letting them run while I was doing other work. When something intrigued me, I'd capture notes in one of those five categories. For example, many of the folks who didn't make it out of the elevator failed to make an "ask," and the investors always dinged them for it. So I noted, "Must have a clear ask." Also, find the judges' "tells." If they have a certain phrase they use all of the time or a bias towards a particular type of business, you can choose who to tailor your pitch to. Marc Randolph repeatedly commented on "two-sided marketplaces" (which describes Plum), so I made sure to emphasize that in my 60-second pitch.

Related: Watch Williamson's Winning Pitch

Once you've identified the patterns, storyboard your pitch to fit them. It'll invariably be too long. Start pitching with a stopwatch, and use the lap feature to capture each paragraph or section. You'll start seeing where it's too long, and you can choose what to cut. You should always aim for 90% of the allotted time because running out of time is a cardinal sin, and finishing early, in full control and with poise, is seen as highly confident and inspiring.

The only way to do that is to say it 100+ times. I literally did that. I said it on the airplane from Raleigh-Durham to Miami. I said it as I drove from Miami to Ft. Lauderdale. I said it as I went through Macy's to buy my blazer (because I left mine at home… oops!) I said it 10 more times before I went to sleep and again in the morning when I took my shower. I said it as I drove to the competition. And then I said it in every quiet moment I had while waiting to compete. Sounds like overkill, but it worked for me in the elevator, and it also worked in 2014 when I won Google Demo Day with my first company, Windsor Circle.

What did you think was going to happen? What was different from your expectations?

I was pretty sure I'd make it out of the elevator, but most of the winning companies in the past episodes had significantly more traction than we did (we're earlier than most contestants), so I wasn't sure if we'd get an investment.

Related: What Do You Do When an Investor Suddenly Changes the Terms Mid-Deal?

Why do you think they opened the doors?

I think they opened the doors because I emphasized the things that successful contestants in the past had, and I delivered the pitch well. (I better have — I practiced it enough times!)

How did the negotiations go? Would you do anything differently?

I very much wanted to avoid negotiating live. No one does that well. So, I anchored my ask to terms that I'd already raised money on and gave just a little sweetener that was undeniably a good deal. It had the exact effect I hoped for. Two of the three investors agreed to invest and didn't touch the terms. In fact, if you watch the episode, it flipped around and they started pitching me on which investor to go with.

What do you plan to do with your investment?

We serve people who want to own vacation property and see co-ownership as a viable way to make that happen financially. We also serve real estate agents. This investment will be used to extend our runway specifically to test engagement with real estate agents.

What did it mean to you personally to get in the doors and walk out with a win?

I'm human. I like validation and success just as much as any of us do. The people who I most want to succeed for are my family, and to have my kids and my wife see me perform well and pull off the win was tremendously meaningful. Every dad wants to be a hero to his kids, and every husband seeks the respect and love of his wife. So winning in such a public way feels good, for sure.

Related: Here's the Difference Between a Pitch That Nets a $100,000 Investment and One That Nets $0

What is your advice for anyone thinking of applying to be on a future episode?

Be realistic about the amount of work and time it takes. Not everyone will get out of the elevator, and not everyone will get an investment, but you definitely won't if you don't treat it like a massive priority. If you aren't willing to commit to that, then don't do it. If you're in it, you are in it to win it.

Season 8 of Entrepreneur Elevator Pitch is brought to you by Amazon Business with support from State Farm and Canon. New episodes stream Wednesdays on entrepreneur.com. Follow Entrepreneur Elevator Pitch on Facebook, YouTube and IGTV.

Entrepreneur Staff

Entrepreneur Staff


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