How to deliver a pitch that will win over top investors

Gary Vaynerchuk, Kirsten Green, and other Creator judges advise founders to think two (or three) steps ahead

If you ask the judges of WeWork’s second annual Creator Global Finals how they ended up picking the winners of the international entrepreneurship competition, they have two words: “Adam and Ashton.”

Gary Vaynerchuk—entrepreneur, investor, and chairman of media company VaynerX—says actor and investor Ashton Kutcher and WeWork CEO Adam Neumann approached him on the same day. “They said, ‘We need you.’ And I said, ‘I’m in.’”

Kirsten Green, founder of Forerunner Ventures, came onboard in a similar way. “Ashton told me how passionate he is about the work he’s doing with Adam and WeWork, and how he thought this show was special,” she says. “The companies have ambitions and goals in terms of big business but are also about having impact. It’s an honor to come be involved for a few hours.”

Vaynerchuk, Green, and Kutcher were joined on the Microsoft Theater stage in Los Angeles on January 9 by fellow investor (and rapper) Sean Combs to hand out prizes of over $1.7 million to three mission-driven business ventures and one nonprofit in the Global Finals. They explained what they were looking for in the winners.

Know your unique perspective. “The very basic criteria is, how differentiated is the business?” says Green, an early investor in retail brands like Glossier, Outdoor Voices, Dollar Shave Club, and Bonobos. “Are they really playing into a new space in the market? Are they offering an opportunity for business to get done better, both more efficiently and in terms of delivering a better experience?”

“The very basic criteria is, how differentiated is the business?” says Kirsten Green, an early investor in retail brands like Glossier, Outdoor Voices, Dollar Shave Club, and Bonobos.

When she listens to a pitch, she says, she wants to hear an entrepreneur tick off five items: “Define your business; say how it’s different; say what it is today, what it’s going to be in the future, and why you’re the right leader for it.”

Her dream pitch? “If you could figure out how to touch on each of those five things in a way that’s cohesive storytelling in a quick minute, that’s ideal,” she says. “But it’s really hard to do that.”

Think two (or three) steps ahead. The judges took their jobs seriously, looking for flaws that haven’t been considered or opportunities that haven’t been pursued during the Q&A. “That’s when I start poking a little bit,” Vaynerchuk explains of his investment strategy. “What are their reactions? Do they have a grasp of the second move of their business, not just the first?”

But be honest. While Vaynerchuk values leaders who have ready answers, he can easily suss out spin. “Don’t exaggerate something you don’t understand,” he says.

Chloe Alpert, whose medical-technology-resale startup Medinas Health took home $1 million in funding at the awards, had a ready—and honest—answer when Vaynerchuk asked her about hurdles her company had overcome. She told the panel that a subscription fee for hospitals to use their technology hadn’t worked because cash-strapped institutions weren’t interested in laying out an upfront payment for an untested product. When Medinas decided to charge a fee for each transaction performed on their platform, all 12 of the hospitals they’ve approached said yes.

Keep the consumer top of mind. There was an important human element to the winning pitches. Combs asked Rachel Corson, co-founder of London-based Afrocenchix—an affordable, all-natural hair-care line made for black women—why someone should use their products. Corson answered by pointing out the health risks posed by ingredients in many competitors’ lines. “Every single ingredient [in Afrocenchix’s products] does something for the customers,” she explained. Her products don’t add artificial fragrance on the misguided theory that “all black women want to smell like coconut.”

Take your pitch seriously. Talking to these industry giants was nerve-wracking for competitors—especially considering they were doing it on stage in front of 6,000 people. “Gary V. is an absolute marketing god. Kirsten Green, she knows brands,” Alpert says. “Sean Combs, that dude’s a business dude. My co-founder was like, ‘Oh, yeah, music is secondary. That guy knows business.’”

In the moment, standing in front of them, Alpert remembers thinking, “I need them to know the economics. Every time Gary asks a question, it’s a laser. When Green asks a question, that’s like a bomb.”

The judges clearly enjoyed having a crowd witness the kind of conversations that usually happen behind closed doors. After one exchange with Alpert earned her a round of applause, Vaynerchuk leaned back in his chair and looked out into the theater. “It’s more fun to do this with an audience,” he observed.

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