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Pitching 101: How the Challenge Cup Winner Honed and Perfected Their Pitch


challenge cup
Challenge Cup 2018 finals at The Anthem. Image by Sam Sabin

Getting up on a stage of global players and talking about your startup for just two minutes — that's 120 seconds — is no easy feat. But that's what 20 startup founders were expected to do for the final round of 1776's Challenge Cup competition on March 22.

Maxeme Tuchman, co-founder of Miami edtech startup Caribu, walked away with the night's grand prize, a $100,000 investment from Revolution. But what Tuchman presented at The Anthem that night wasn't improvised. Honing and refining the two-minute pitch took many late nights, planning and practice.

"I have insomnia, so that means it's a late night no matter what," Tuchman said on the latest episode of District Download, our podcast with General Assembly. "For me, you have to know what kind of learner you are. I'm a tactile-visual learner, so even though I type it a lot of time, I also handwrite it."

That being said, Tuchman has always had a knack for pitching. At Caribu's first pitch competition for Harvard Business School alumni in Atlanta, Tuchman walked away victorious.

"If I showed you that pitch deck, it would be so embarrassing," Tuchman said. "It's obviously evolved so much since that first pitch, but I think the reason we did so well and we've done so well, I think it comes from a teaching background."

Long before she started her startup journey, Tuchman was a teacher with Teach for America in Miami. She taught high school economics to about 400 12th grade students in two years.

"When you have had to be a high school teacher, you have had to disseminate information to 18 year olds who would rather be anywhere else but in that seat, you very quickly learn how to talk about things and how to create pitch decks, pretty much," she said.

For Tuchman, a good pitch comes down to four essential parts:

  1. Sharing the story of the startup and product.
  2. Talk about your traction or future potential. 
  3. Showcase your team.
  4. Make sure people recognize your competitive advantage.

Tuchman shared more about her process in the latest episode of District Download, which also includes live takes from the Challenge Cup Festival 2018.

Subscribe to District Download on your favorite podcast app: Apple Podcasts, Stitcher and RadioPublic.

All music for this episode comes from Broke For Free, Podington Bear and Komiku under Creative Commons licenses. Our theme song is “Playground Pigeon” by Podington Bear, and other tracks for this episode include “Something Elated,” "Decisive Battle with the Childhood Friend" and "Elephants on Parade." 


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