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Jack Dorsey’s #1 rule for pitching your startup: “Show them something that works”

August 20, 2025

Jack Dorsey, Jim McKelvey, and another engineer built the initial prototype for Square in a month. As Jack recalls:

“I could actually swipe a card, generate an electronic receipt via email, and then send it out to a person. I loved this because I would go around to all these angel investors and VCs and charge them $5-50 to show them my new idea.”

This prototype was critical in helping the company raise $10 million in initial funding from Khosla Ventures. And Jack believes it’s a lesson all founders should take to heart:

“The thing that really inspires people is a working product. When you’re pitching someone, the best thing you can do is show them something that works.”

Jack continues:

“We did this with Twitter. We had a great number of users… and we had investors who were coming to us who were already users of the product. Their families were users of the product. So the story became very easy to tell and they could easily see why this was something that was powerful.”