NEW YORK (TheStreet) -- Jack Dorsey is a year younger than me. That fact alone makes me want to drown myself in a tub of Jack Daniels.Jack Dorsey founded Twitter in 2006. Of course, he conceived the concept several years earlier. Jack Dorsey had the inspiration for Square in 2009. By 2010, he rolled out the application. Just a few weeks ago, Square signed a landmark mobile payments deal with Starbucks ( SBUX). I was fortunate enough to appear on CNBC's Squawk on the Street Wednesday morning. I discussed the future of brick and mortar retail with Stacey Widlitz, president of S. W. Retail Advisors. As you watch the video, it becomes clear that Stacey and I run in different worlds. But, that's good. It makes for varied conversation. Surprisingly, the CNBC host I was most frightened of going into the interview -- Simon Hobbs -- caught my drift more than the others. That became evident before I even spoke. Hobbs says what I pretty much had planned on saying to open the segment. While I can't say I blame retailers for closing stores and shrinking square footage, there's a contradiction inherent in Widlitz's notion that "Retailers need to embrace
Everybody involved in this argument -- the retailers, the media, guys likes me, folks like Stacey. We all could use a shot of Jack Dorsey. Dorsey created Twitter before most of us could have even imagined such a thing. Now that we're all -- finally -- on the same page, he has moved on. When we were just catching wind of Twitter as a sustainable phenomenon, Dorsey had Square in the works. Once he gets that to a certain point, he'll likely scale back his involvement and move on to the next thing that never even hit you and I. He's a special dude. While very few people reach Dorsey's level, there are others out there like him -- Steve Jobs, Jeff Bezos, Tim Westergren. Folks who dictate the future. Others exist who are like Dorsey, but we're not sure who they are. These people themselves might not know. They may never know. Lots of stuff has to happen for a capable person to turn into Dorsey, Jobs, Bezos, Westergren. To have ideas, see them through and change the world. Much of it comes from within. External things such as luck, right place/right time, nepotism, who you know and who you . . . . All of that stuff can play a role. Simply put, it's difficult to cut through. The reason why Starbucks, Lululemon, Apple and Amazon expand, while so many brick and mortar dogs feel the need to contract, might have something to do with iPads and iPhones, but in general, it has less to do with gadgets, coffee and yoga pants than our intuition tells us. Product -- or "content" as Simon called it -- matters. Absolutely. But, you cannot halt your analysis there. And you definitely cannot stop at the all-too-easy conclusion that X (online and mobile sales) are growing faster than Y (brick and mortar transactions) so physical retailers must do Z (close stores). Instead, focus on the core reasons why so much of brick-and-mortar retail experiences distress. Pay attention to how they react. Pretty much all they do is react . . . feebly and way after the fact.
For example, while Amazon fashioned e-commerce as retail's future, big boxes got bigger. Now, when it's abundantly clear that that was a horrendous choice, these same retailers defensively reverse course. Unimaginative old guard retail is always chasing. First online, now mobile. They chase. They operate within the frameworks more innovative individuals and companies create. And then, they take the same old tired tools of retail and try to fit them into this tech-oriented paradigm. They don't get it. It's not about bringing technology into the store. Virtual checkouts. Even mobile payments. These things cannot bring success, let alone drag you out of the abyss, in and of themselves. It's about thinking like a tech company, from conceptual and philosophical standpoints. You cannot think like a tech company, conceptually and philosophically, without the right people. That means people like Dorsey, Jobs, Bezos and Westergren. But it also means people who truly understand why those four and others like them are different, why they lead so well. And how the DNA of a perpetual startup looks nothing like the DNA of a retail shop. Best Buy took a step in the right direction when it hired former Starbucks executive Stephen Gillett as a president and put him in charge of an increasing number of areas. Gillett is young and a tech guy through and through. Radio Shack now has the opportunity to do likewise. I don't think it will, but, at the very least, it would be nice to see the company stay away from people with failure and mediocrity ( Sears, K-Mart or Toys R Us) lining their resumes. At the time of publication, the author held no positions in any of the stocks mentioned in this article. Follow @RoccoPendola This article is commentary by an independent contributor, separate from TheStreet's regular news coverage.