Most entrepreneurs would kill for two minutes with Chris Sacca. The guy has an investing record that rivals Warren Buffett's--he's invested in winners such as Twitter, Kickstarter, and Uber--and he can tell within minutes if a startup has potential. (Of course, no one's perfect--he missed getting in on Airbnb.)
Earlier this year, Alex Blumberg, former NPR economics reporter and Planet Money co-founder, tracked down Sacca because he wanted to pitch him on his new venture, a network of podcasts. (His excellent podcast series, StartUp, chronicles the entire experience, warts and all, and you can stream that first episode here.) Needless to say, the meeting does not go well and Sacca ends up schooling Blumberg on how to pitch an investor. The advice is priceless:
Lose the pitch deck.
Before meeting Sacca, Blumberg spends hours refining his pitch deck, which he later admits is a rookie move. Within minutes, Sacca is taking his guest for a walk, and Blumberg fumbles without his crutch. His pitch meanders, he goes off topic, and confusion and boredom flash across Sacca's face. "You've got to tighten up your story," Sacca tells him. While it helps to have an outline, the idea of your company should get you so excited you don't even need to have one. And you should be able to at least tell the basics of your story in two minutes.
Make 'em feel #FOMO.
You know that feeling you get when a friend posts photos of her vacation in Maui? That's called fear of missing out--or FOMO for you non-millennials--and it's what Sacca wants to feel when he's hearing a startup pitch. He doesn't want to miss the next Airbnb. "Once you have FOMO on your side," says Blumberg, "you no longer have to ask people like [Sacca] for money. They're lining up to give it to you."
Another thing Sacca wants to see is that you fiercely believe in what you're saying. As he tells Blumberg, he "looks hard" at the conviction of the people pitching him. It's the reason he backed Instagram. "I sat down thinking photo-sharing had been done millions of times," Sacca recalls in the podcast. But as he listened to co-founder Kevin Systrom, he got the feeling Systrom was looking through him "to some spot five years in the future. What starts as this, 'All right, kid, what have you got,' is just, 'Wow, let me get on this thing.'"
Though Sacca doesn't say it, he clearly wants Blumberg to sell his experience at NPR. That means telling investors who he is and why he's the man to get this podcast thing off the ground: "You probably know me as a producer for This American Life, a top podcast in iTunes," Sacca offers. It makes Blumberg sound believable when he says there's "a hunger for this kind of content." After all, who would know better than him?
...And your knowledge.
Just because your pitch is short doesn't mean it can't be informative. When Sacca gives a sample pitch to Blumberg, he cites trends in the "macro environment" such as "more podcast integrations in cars," the new version of iOS which features a podcast app, and advertisers who want to get involved. Next, still playing the role of Blumberg, he cites specifics on how much money he's after--$1.5 million--who he plans to hire, and how many subscribers he can sign up in less than six months. Those are all questions to which investors are going to want answers.