For entrepreneurs to pitch effectively, they must first free themselves of attachment — the root of all suffering.

Which makes 500 Startups Venture Partner, Entrepreneur-in-Residence and pitch coach Andrea Barrica a spiritual guru.

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“I force people to constrain and use the smallest amount of time to explain what’s most interesting about their company,” she explains. It’s rewarding, but like any effective conditioning process, no pain, no gain.

The 120 Second Investor Pitch

Now coaching her fourth batch of founders for 500 Startups, Barrica has continually shaved the amount of time they have to present at Demo Day. Instead of 3.5 minutes, each team now has only 120 seconds to make its case.

Investors are more excited and engaged, Barrica said, and founders have gained a deeper understanding of the value they’re offering.

“I was working with a technical founder who said, ‘I need at least 10 minutes to explain my technology, it’s too complex,'” Barrica recalled. “I told him what Einstein said: ‘if you can’t explain it to me in a minute, you don’t understand it well enough.'”


That upset them “a little bit,” she admits, chuckling. “But by the end of the session, they really understood that what they were doing wasn’t that hard from a market standpoint.”

Googling the right investor deck templates and talking your way through for ten minutes is easy, said Barrica. “Why? Because you don’t have to choose what’s important or exciting,” she explained. “You just put everything in and people pick what they like. It doesn’t take any skill to do that type of presentation.”

“What you need is for the investor to know is that this a great market, and you can do that in 30 seconds.”

“What you need is for the investor to know is that this a great market, and you can do that in 30 seconds.”

Part of Barrica’s value to founders lies in her outsider’s perspective. “People don’t really know what they’re doing, they don’t know what they’re building, or why it’s awesome or differentiated,” she said.

Too many founders start with a sales mindset, building pitches around customer value and delight.

A memorable startup pitch is “an exercise in empathy and storytelling,” not salesmanship, said Barrica.

[In a monotone]…this is my market, this my product, this is the problem.” I’m not about that. I’m about, let’s tell a story.”

Differentiate Your Startup Pitch, Or Don’t Bother

One of the exercises Barrica uses to give founders a better perspective on their own companies is to ask how they’d explain it to “an outsider, like their grandmother or a 10-year-old niece.”

During a 12-week batch, Barrica meets weekly with founders. Each receives highly tailored advice, but all are encouraged to find ways to differentiate their pitch, even from each other.

“People sign up for a pitch session with me and they sit down ready to pitch, but typically, I don’t let them,” said Barrica. “Instead, I’ll ask, what are the three reasons why someone shouldn’t invest in your company?

Most founders reply with negative feedback they’ve already received, such as problems with their team or product.

“Once that’s in their head, you find that they don’t start with the same words the next time,” she said, because they’ve started to anticipate their audience’s needs and wants.

“Once you get people in that mindset, they typically don’t do the super-boring, generic precut pitches I get when I don’t prompt founders with anything,” said Barrica. “So many people don’t understand why they’re going to win. They can’t connect the dots very well.”

She advised adding a single metric to a tagline, or taking the time to identify traction benchmarks that are sector- and product-specific.

“Whose lunch do you eat when you succeed? That’s what most people can’t tell me when they come in,” said Barrica. “If you’re successful, what happens in five years?”

For pre-launch companies, relating current strategy to future outcomes can go a long way toward building credibility with investors, she added. “Be able to talk intelligently about what in your industry will be interesting to investors or customers.

“Whose lunch do you eat when you succeed? That’s what most people can’t tell me when they come in.”

Quiet Power: “A Very Compelling Pitch Style”

Not all entrepreneurs are, as they say in the restaurant industry, “front of house” people, but Barrica said introverts and unlikeable folks can also pitch effectively.

“I tell people that quiet power is a very compelling pitch style,” she said. “Sometimes, founders avoid me like the plague because they think that I’m gaining to make them be really gregarious and loud,” she said, but that’s the opposite of her strategy, which stresses authenticity.

“You don’t have to be something you’re not, but you have to be brilliant, brave, and effective,” said Barrica. Discomfort with public speaking “isn’t an excuse to be boring or verbose,” she offered. “I would say if you don’t like pitching, you have to be even more brief.”

When Pitching Investors, Screen Your Trailer, Not The Movie

Before we wrap up, Barrica refers again to deadly Power Point decks packed with minutiae investors won’t remember after the pitch concludes.

“Those details are better for a Q&A in a one-on-one meeting,” said Barrica, “and if you want to get that one-on-one meeting, you keep it simple.”

“Your pitch is going to hurt you,” she warned. “That’s why coaching is so important, and that’s why my job’s so hard – it’s hard to templatize what I do, when it’s more of an art than a science.”

Barrica admits a bias, but “I hate other [accelerators’] demo days because they’re just robots, one after the other. [In a monotone] this is my market, this my product, this is the problem. I’m not about that. I’m about, let’s tell a story.

Presumably, without opening, “in a galaxy far, far away?”

“I love that example,” said Barrica. “No, we’re just looking for the teaser trailer.”