The World of Money Lore is Wild Right Now

Currencies are being invented by Tik Tokkers, pokémon cards are a type of retirement strategy and stock options are a video game. This world of digital money innovation is a blast, and that’s why I threw myself into it. And if you dive right smack dab in the middle of this digital money evolution revolution: One thing you’ll find is the fintech battle for glory. There are many fighting the good fight amidst the fintech war, but one of the most rapidly rising, unstoppable champions is Jack Dorsey’s financial wonder.. The one-product underdog, turned multi-billon-dollar financial & crypto beast!

This is… The Square Story!  

Click Here To Watch The Immersive Video Version of This Story!
Click Here To Watch The Immersive Video Version of This Story!

What is Jack Dorsey’s Square Incorporated?

Square Inc. is… in the simplest possible terms: a financial services company based in America, co-founded by Mr. Jack Dorsey and Jim McKelvey..

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

But in more complicated terms…

Square is a future-first, financial technology brand focused on innovation in and around the world of digital payment & money: From credit card processing, to point of sale infrastructure, to business management digitization, to e-commerce management, peer-to-per payments, to investment brokerage, to crypto player, to digital rewards system, and soon-to-be, modern bank.

Square is, or is planning to be, an everything financial innovative giant. Square is a beast, with a 2021 market cap of over $120 billion dollars. Square is a great many things, folks. But here’s the thing about that. To become a thing that is a great many things, one must first be one thing, and early on in the running, Square was a seemingly silly idea. At a time when PayPal was the “internet money” company of the space, and payment processing was not exactly an inviting world for competition: this untapped fintech war was ridiculous. Ludicrous. Madness! To want to be a part of. But the young, ambitious and oh-so-bold Jack Dorsey was in the game of ludicrous business competition in the world of technology. For this was the year following Dorsey’s other passionate tech innovation. You may have heard of it, that one would be Twitter.

Well folks, if you will…. Immersive Yourself!

The Origins of Square – Where Did Square Come From?

The year is 2009.. Jack Dorsey is a young, fresh, fly and spry tech millionaire that has just been.. replaced as CEO of Twitter. Word on the street is he was booted from the big position for too-often leaving work early to take up yoga and fashion design.

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

Whatever the case, Dorsey’s credibility was proven by this point, as Twitter was a rapidly growing success story already. Dorsey was a silicon valley hotshot. So in 2009 when Jack’s buddy ol’ pal Jim McKelvey was having a dreadful little time in the need of innovation: He remembered his buddy JackyD.

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

Jim was struggling, trying to efficiently complete a $2,000 sale for new glass faucets and fittings because he had no way to accept credit cards easily. More specifically, Jimmy McKelvey was a man of glass. Not made of glass, but he owned a glass blowing studio small business in the St. Louis area. At this time, it was a struggle: the choice of whether to have a credit card machine with an intense system behind it, that took all cards but charged a big fat, varying fee, or maybe a simpler card processing option that only accepted a few cards, forcing him to bid farewell to many sightings of potential cash money. Well Mr. Jim McKelvey reached out to his old friend Jacky D, to tell him about this classic small biz struggle.

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

The Opportunity in Payment Processing

Dorsey saw new opportunity before his eyes. Jack decided, he needed to invent cheaper glass Faucets, to solve this issue once and for all!

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

No, it was the money thing.. not faucets.. I did a joke there. That was just a joke.

Jack Dorsey put 2 and 2 together: It equaled 4! And then he started working on something even cooler than that basic math. He realized that most folks those days were starting to purchase Apple’s brand spankin’ new “iPhone”. And looking at it broadly: this was a product that had all the elements plus many more of a traditional credit card payment processor. A screen, access to transaction history, the ability to sign with touch: plus, it was sleek.

Square’s First Product: The Square Reader

So these two wild boys formed a little team to create what became the infamous, the original: Square Reader.

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

A teensy little device that pops into the headphone jack on an iPhone. This sucker connected with the Square app and all of a sudden made the credit card magic happen easier and sleeker than ever before. PLUS; the real kicker: was Square’s sexy, minimal payment fee structure.

Remember The Time: No FinTech Yet

Beforehand, these high end, bulky card readers were expensive, ugly, plus the fee structures were complicated, varying and generally high: all filled with hidden fees and whatnot.

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

But Square was here to keep it simple: the square reader would be shipped out for free, to whoever ordered it. Then as a fee structure: It was a flat 2.75% + $0.15 per transaction. No hidden fees, no variation depending on card, cost, etc. Just that simplicity. And with that, they even shortly after decided to drop the $0.15 portion of the fun. So Square payment fees evolved to be just a smooth, simple 2.75% – no need to get fancy with it.

Square Officially Launched In 2009

Jack Dorsey & Jim McKelvey launch this juicy new company officially in early 2009, amidst the great recession.

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

They rapidly develop a workable product and start on the path to funding.
And.. Well.. If you can imagine this.. They… did not have a difficult time funding at all!

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

Within days of creating the initial product, they establish deals and relationships with payment processors and banks so that Square will be able to act as an intermediary: sorta like PayPal but also not really.

Announcing Square To The World

Across the next few months, Jack and Jim harnessed those juicy friendships, raised a total of $10 million in Series A funding and continued along the path of evolution. In December of 2009, it was time to chat with the world a bit. So Jack Dorsey set up a conventional press conference to announce the specifics about the anticipated Square launch…… Oh, well actually: Jack UNCONVENTIONALLY announces the OFFICIAL LAUNCH of their new company in a 99-character tweet on December 1st, 2009.

Smooth Sailing!

From there, sailing was smooth, fast and intense, baby. Let’s hit some “quick n slick timeline moments to dive n thrive to” (riff it a bit)

Dorsey announces the official Square website in December, 2009 to showcase Square’s first official product: the Square Reader. You know the one, it’s square-shaped.

Square goes into a sexy, exclusive little “private pilot run” limited to just 50,000 folks.. Until November of 2010: when the door is officially opened for the regulars of the world.

Square’s Rapid Growth Began

May of 2011 comes along and Square drops 2 new technological bangers: the release of their new apps; Square Card Case (eventually to become Square Wallet) and Square Register, their state of the art point of sale register system.

Square’s growth is so intense, Jack Dorsey buys himself a new house!

But also, by 2011.. 50,000 readers are shipped across the US amounting to a vast 66 million dollars processed.

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

The hype is real. Square is spreading and folks, we’re changing the game for small businesses. Do you understand this? I mean, 2021 is a technological dreamscape, but picture it like this. In fact, immerse yourself and imagine the impact Square is having on the world at this moment in history.

An Example: Why Square Was So Great

Meet Jon Velez.

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

Jon opened up a little towing company called Norwalk Towing, over in south-west Connecticut in 2008. The name of the game for Jon is dealing with folks that had no intention of dealing with Jon that given day. You don’t get in your car expecting to have to do business with a tow truck upon your trip. No, no. So upon experimentation, Jon tried accepting cash only, as that was the only thing one could do. But oftentimes, folks didn’t have the cash. Checks were another idea. But even then, who in the heck has their check book on them casually?

So to stand out from competition, Jon started accepting credit card payments. A rare thing in the game of tow trucks at this point in time. In the early days of this move, Jon would have to write down credit card numbers on a piece of paper then process them later once he got back to his office. And of course, things can go wrong at the point. As Jon puts it, sometimes fives looked like threes, or cards were declined. Fixing these issues often took weeks upon weeks. Well in time, Jon found Square. The sleek, one inch little credit card reader that just pops into his phone to process the payments on the fly. This was a goddamn game changer for Jon Velez, as it was for a great many small businesses in similar situations.

Big Business Moves In For Square

But here’s the real kicker. In 2011 and beyond, word got pushed past small businesses. Big name brands were switching over to Square options because it was becoming the cooler, modern way of doing business: between the Square readers and the hot new Square Registers, I mean come on. People wanna live in the future, man. Don’t let em get held back at the checkout counter.

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

Though smooth sailing often leads to rough waters… And that’s just what came in March of 2012..

Square Vs. PayPal – Square’s First Real Competition

PayPal saw this sector within this thriving fintech space that it once formulated and founded upon. PayPal didn’t like what they were seeing one bit. So in March, here comes PayPal with their latest and greatest innovation: “PayPal Here” – An attachment for your mobile device to process credit card payments.

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

In the shape of… wait for it…

A triangle!

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

And in response to Square’s beloved, simplified 2.75% processing fee: PayPal Here announced a simplified, 2.7% processing fee on their triangle dongle.

This right here is the cruel world of the free market, folks. Or the cool world of the flea market, depending on your perspective of course.

The Pressure of Competition

Well the heat was on now. Square has competition in the water and it just so happens to be the biggest fintech player in the world.

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

Different businesses are going in different directions here in our 2012 world. These two options are becoming the leading players, but it’s definitely a cutthroat battle for business. That is, until the table is turned in August of 2012.

The announcement comes upon us, that Starbucks is investing $25 million dollars in Square’s business and that Square will in fact be their exclusive processor of debit and credit card payments from this point forward. BOOOOOM, BABY. EAT THAT, PAYPAL. PUT THAT IN YOUR GODDAMN MACHIATO AND CHOKE ON IT.

…Sorry, sorry. We’re getting excited here.

Starbucks Partnership With Square Changes Everything

Well this deal definitely brought the light of glory right on back to Square. And the fun continued…

In early 2013 Square drops the reveal of Square Stand, the fancy little device that turns the iPad into a complete point of sale system quick and easy

In late May of 2013, Square drops another banger on the world: The reveal of Square Cash, which would eventually rebrand itself as simply “CashApp” – A real deal, simple peer-to-peer money sending app

A month later Square launches Square Market, which lets sellers of the world create a free online storefront with online payment processing connected through to their brick and mortar set-up.

These new innovation drops are rocking us back and forth, this square company is wild, man. Wild!

How Much Money Was Square Processing at This Time?

And the numbers within this wild time, you ask? By 2013, Square was processing $15 billion dollars per year. That’s billion with a “B” – B as in “Bob” – Bob as in “Robert” – Am I making myself clear here?

A few short months later, Square had YET ANOTHER big boom to drop on the fintech world. In March of 2014, they announce that they’ll start allowing sellers to accept bitcoin on their own digital stores through Square Market, if they so desire.

Square’s Bitcoin Move in 2014

A big bitcoin move in 2014. I mean, in case you don’t realize it, that’s a big, bold move for a massive growth company at this point to do. Bitcoin was not even close to what it is today, but they saw the potential.

Then in May of 2014, Square launches a legendary under-appreciated aspect of their business: Square Capital – An option that offers financing to merchants using Square!

Square is Going For The Horizontals and The Verticals

I mean, do you see this rapidly expanding road that Square is on? This is a game of owning the verticals and the horizontals in this fintech-developing world.

This is what a thriver of a growth company looks like, folks. The competition made the waters scary briefly, but Square overcame and thrived because of it. There were a lot of smiling faces at this point in time, and a lot of cartoon dollar signs within their eyes. This is what happens when business goes well. It’s basic science.

And do you know what happens when your tech startup hits massive growth and the dollar signs grow larger and larger within the eyes?

Well, of course, you take that thriver to Wall Street and you launch that sucker on the public market immediately! And on November 19th, 2015. That day came.

Square Goes Public – The Square IPO

Jack Dorsey welcomed a celebratory morning alongside his mother, as Square officially went public on the New York Stock Exchange. How precious.

Square IPO’d at $9 bucks a share, hit $11 by opening bell, peaked at about $15 midday and settled things off at about $13.

After all the madness. All the hype. The brief struggle, and a preliminary large span of doubt prior to it, the Square IPO was a glowing success: and Jack Dorsey’s Mom was in fact proud!

But, while this may seem like the happily ever after moment in our tale, it is not so exactly that…

Square Starts To Underperform

IPO day was an uplifting turn of events, but in the days, weeks and months to follow. The smiles soured. The happiness began to wane.

It took about 60 days, but at that point Square’s stock price fell below IPO pricing, disappointing investors heavily. The stock price continued on a dismal, downward path for about a year. Earnings were disappointing analysts, harsh news was coming out left and right: fear-mongering.. If you can imagine that.. Folks talking up how the world was wrong to be hyped over this fintech potential, etc, etc.

When passion starts to wane at signs of weakness, those that feed off of negativity thrive.

Shoutout to my fellow Tesla investors out there.

Dorsey Turns Things Around

Well in due time, Square started to turn things around towards the later half of 2016.

Squares EBITDA turned positive for the last 3 quarters of of 2016, with strong profit margin growth going down in the fourth quarter especially.


But press is still very mixed at this point. The nay-sayers were certainly saying nay, and boy were they enjoying it.

And as it turns out.. in 2017... These nay-sayers, well.. They got the chance to take a nice, long look in the mirror because Square was back, baby!

They expanded rapidly in 2017, growing with incredible earnings, massive moves by the company, continued evolution and huge user growth. Square Capital in particular was an explosion of success and Square was finally making moves in the UK and beyond.

Square went on to have a couple of cute little hiccups, mostly following the tech broader market, but for the most part: these suckers were killing it from 2017 onward and onward..

The Chart Speaks For Itself

I mean, let the charts speak for me on that one!

Square’s 2020 Crash in March

Like most things in the world, Square had its biggest and darkest fall at the forefront of the Pandemic, jumping from about $83 bucks a share in February to about $38 bucks in the valleys of march. But the beautiful thing about Square, is they took up the opportunity to make massive moves in 2020 following the chaos.

They had already had juicy things going on in the world of e-com, but friends, they were a brand that thrived in this environment of brick and mortar stores needing to quickly adapt to the online world. They made massive moves in their verticals sector of e-com, and that, along with the continuous rising popularity of CashApp amounted to absolutely ferocious growth across this last year and a half.

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story

That, and well.. Of course.. The beautiful, brave move many of us know Square made in October of 2020…

Square Buys Bitcoin

Square Inc. decides to buy 4,700 bitcoin with the cash on their balance sheet! By the end of 2020, Square held about 5% of their total assets in Bitcoin, and this year they bought even more.

So suffice to say, it’s been a very profitable year beyond the core business as well.

And as for our forward-looking perspective, in terms of this crypto interest Square has going on: They bought Tidal earlier this year. You know, Jay-Z’s music streaming platform that no one cares about.

The Rapid Growth of Jack Dorsey's Square Inc. - The Square FinTech Story
Well, the talk of the town says that the idea of implementing NFT’s with Tidal, along these lines of passionate music fans buying unique ownership of albums through the Ethereum blockchain. And well, that certainly sounds like the future-forward Square we’ve seen exist over these last 12 years.

Square Is Unstoppable

Ladies and gentlemen, Square is a beast. They were once threatened by and often belittled in the media about the classic behemoths of the financial world:
But it seems Square has itself become a behemoth in the financial technology world, and as a fan of innovation in any form: I very much enjoy this tale.

TLDR; Jack Dorsey’s Square Inc.

Jack Dorsey’s friend sold glass but some glass was too hard to sell because credit card processors sucked and Jack’s problem-solving, tech-first outlook on life amounted itself well to establishing a game-changing financial play that would go onto to evolve itself into all sorts of juicy forms to change and improve the world of finance, sales and commerce in general.

And that there is my take on the story of Square..

The Rapid Growth of Jack Dorsey’s Square Inc. – The Square FinTech Story

If you’re interested in seeing more stories like this, I do these “Money Lore” things on all sorts of fun stories in the world of money: Scandals, scams, business tales, crypto madness, short squeezes, wild moments in money history, etc, etc. Go check em out!

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Thank you so much for reading my take on Jack Dorsey’s Square Inc. – I’ll see ya real soon… Be safe out there..