Yesterday I had the opportunity to hear from & meet Jack Dorsey, Creator of Twitter & Founder & CEO of Square. He came to discuss Square & making payments better for everyone. What became clear is that Square is not just the shape of their product, not just the name of their company, not just a shape, not just about a payment mechanism. Square symbolizes a vision. A vision about the entire experience around payments & the transaction of value.
I remember discovering Square when it first hit the public eye. The timing was perfect because it lined up with the opening of our newest Iorio’s Gelateria in downtown Ann Arbor. From this point on, I knew that as long as Square became available soon enough we would not have to purchase an antiquated POS system (there’s a reason they’re called POS). This was game changing for our business. After examining a few other new POS systems (tablet based, cloud infrastructure, etc) we ultimately decided to go with Square. Why? Great design, simple to use, every function we needed at the time, & fabulous support (via Twitter of course) from the Square team. Plus, it was cheap & easy! Roughly $500 for an iPad, a complimentary Square reader, & only 2.75% on each transaction.
Jack started off last night’s discussion with the story of Square. He described an anecdote about his friend who made beautiful glass art, but was unable to sell a $2,000 piece of art to a lady interested in purchasing it, because he didn’t accept credit cards. The lady ensured she would return with a check, but never did.

“The future has already arrived, it just hasn’t been distributed yet” – Jack shares a quote by science fiction writer William Gibson
This story is the same for many individuals & businesses around the world. I have experienced it personally…when I first started Iorio’s we didn’t accept credit cards. Cash only. So many people asked if they could pay with credit card. Imagine a 15 year old’s disappointment to lose out on a sale because of a inability to accept a form of payment. Seems criminal. Where is “Freedom to Pay” in the Constitution?!
A month later Jack & his friend had built software & hardware to accept mobile payments. A great demonstration of Jack’s advice “write it down”. Whether on paper, typed up, in code, somewhere…write it down. Otherwise, nothing happens, except excuses. Take action. Do something. That’s how Square started.
Jack also went into some impressive stats that support Square’s vision…
- Only 6% of commerce is online
- Credit card companies accept 10% of applicants, Square accepts 95%
- Pricing of credit card fees hasn’t changed in 62 years
- Starbucks touches 70 million unique Americans per month (considering Square’s recent partnership with Starbucks, this is big news!) And to give some perspective on that 70 million unique visitors…the New York Times unique visitor count is around 25 million per month.
One of my favorite parts of Jack’s wisdoms shared was his bridge analogy. He popped up a picture of the Golden Gate Bridge & asked the audience how many have traveled across this majestic structure. What do bridges do? They provide utility. They help move something from point A to point B. They result from the intersection of design & engineering. What does Square do? Provides utility. Move money from point A to point B. Jack is designing & engineering a company to design & engineer a product. It’s not about “putting ourselves in front of our users” according to Jack, “that’s selfish”. If there’s conflict in the company, that materializes in the product. This clearly demonstrated Jack’s attention to company culture, of significant importance, but often under valued in growing companies.
Speaking of culture, Jack mentioned that his job is to keep Square focused. It’s clear that Square works hard. They couldn’t get where they are today without working hard. I spoke with several people who work there, all who were friendly, engaging, & genuinely enjoying working at Square. That was inspiring to see. Jack also seems to be a very thoughtful entrepreneur, seemingly down to earth, clearly driven, & introspective. He talked a bit about his time management style, which was applaudable & well thought out. Themed days. He’s deliberate about planning his time. Obviously stuff comes up that disrupts with plans, but setting his cadence for each week seems like a well thought out way to organize his responsibilities. Well done Jack!
After telling a bit more about his story & Square, Jack posed this question to the audience: What can Square do to make payments better for everyone?
Questions, answers, discussion ensued.
Then the after party began at the Computer Science building on campus. Jack couldn’t even get in the door before a line of students, wantrepreneurs, & others formed a line to get to talk with & snap photos with the visionary entrepreneur. It was encouraging to see so much interest & respect for Jack & what he’s doing. I did notice that there were maybe 10-15 females in the audience during the event. Clearly outnumbered. There’s no debate that guys outnumber girls in the tech world. And it’s probably a good thing this event didn’t get promoted all across the University, because I’m sure every sorority would send a troupe of its members to the event & to meet Jack. After all, let’s be real, he’s far more attractive than Bill Gates.
Before he left campus, Jack enjoyed Raspberry dairy free sorbetto from Iorio’s gelato cart (which we moved outside the Computer Science building to make it easier for Jack to get some). He suggested a team photo, so the Square team posed around the cart & then Nick & I jumped in for a Square/Iorio’s photo!

Official endorsement?! Grazie! Gelato does go well with tea & alcohol (for Square’s Friday Tea Time!)
Throughout my journey using Square for my business I have been challenged by banks, by customers, by team members. But it’s very clear that Square is here to stay & as long as they’re around & continue to innovate, I’ll be a strong supporter!
Venture on,
Mel, the venture gal






