MindsetCEO Blog: It's Time to Hit the Road Jack.


Heading South on US 101 to Palo Alto

The road is full of possibilities. I am ready to fly again after 15 months of staring at the blueish dull glow of the computer screen talking to people all day in a flat two-dimensional plane. I finally get to punch my ticket for a flight to SFO. It is ironic that the year I finally achieve lifetime gold status on United for a million miles flown, I would be grounded. No longer.



I think the great American author, Jack Kerouac said it best.

“Nothing behind me, everything ahead of me, as is ever so on the road.” Jack Kerouac, On the Road

At the heart of it all, I am a Willy Loman creature. The hustle and grind of the road are both comfortable and familiar. I still love the pursuit. What will be my new challenge? Where will the next deal come from? I can only allow myself to sit on my laurels for a short time to enjoy that last win.


My fate is not tragic. I have chased after my dreams. I have taken risks that have paid off. For sure I have made mistakes and learned from them. But my decisions and choices have never caused me to look back with any real regret.


It’s so easy to be intoxicated by the power of technology. But you can’t see the world from a lifeless web browser. The currency of business and sales is trust. Can you really build lasting human connections that foster trust, respect and safety on a Zoom call? Hell no.


You can call me old school, but I am new wave. I had a desktop PC in ‘82, a laptop in ‘83, and a cell phone by ‘85. I sold the original IBM PC, mainframe software, client-server software, web, and mobile applications. I have reinvented myself and upgraded my skills countless times. It is hard to fathom that I am now entering my fifth decade of selling hardware and software technology. I was an ERP enterprise software expert, then a payments geek and now I am a fintech guy.


Forget all the stereotypes, selling is an honest profession. You get paid according to production. It is the most quantifiable least politicized position in a business. Sales is not about tricks or convincing a prospect to buy a product or solution they don’t need, doesn’t work, or can’t solve a critical problem.


Technology is imperfect and most software companies are pushed to deliver products before they are ready for market. Let’s face it, there is no software working today without bugs. The more visionary your product, the more you will need to evangelize as well as be consultative. It’s come down to trust and safety. Did you really listen to your customer’s problems and needs? Do they believe you have their best interest in mind? Do they have the confidence that you and your company can deliver the goods? Good luck doing all that over Zoom.


Technology has always been a means, not an end. It will not replace us. Technology has the power to make our lives better, but it can’t make us better. It does not make us smarter, more compassionate, or more interesting. It can give us lots of data and information. But not a single idea came from a binary computer chip. Artificial intelligence and machine learning may be the best of computer technology so far. Still, it is nothing more than a technological framework for representing human ideas and learning processes.

So, it is fitting that my first business trip since the pandemic hit takes me back to Silicon Valley. My career as a tech entrepreneur began on a trip from New York to San Francisco back in 1987. My partner and I had a small consulting company. We made a deal to acquire a legacy 4GL development tool from Palo Alto-based software company, Ross Systems. Ross Systems was founded in 1972 by Kenneth Ross a visionary technologist and one of the genuine good guys of Silicon Valley.


This time, I am making my first trip to visit the headquarters of TabaPay. They are a fintech startup based in Mountain View, CA. I have worked there for six months remotely with no in-person contacts.


As I get in my rental car and drive south on the 101 tonight, I recall much more than just my first trip to Silicon Valley. I truly think of every time I landed here from New York late at night, tired and hungry from the long flight. Because as soon as I hit the pavement on the 101, my energy levels spike and my mood fill with endless possibilities.


There is no bad place or time to start a business. Yet, being an entrepreneur in Silicon Valley is still something special. Maybe it’s in the California air. This sublime peninsula stretching from San Jose in the south to San Francisco in the north still has the smell of magic. Is the magic is coming from the original computer chip factory at Fairchild Semi-conductor or Intel? Is the magic from the early hardware innovators like Hewlett Packard or Apple? Does the magic come from the myriad of software companies from Oracle to Google?

The magic comes from the people who live and work here. The people that get on the road or street every day to work, meet and mingle. Human interaction is how sparks are created that generate new ideas and possibilities. That is why it's time to leave our remote workspaces and the comforts of home. Time to get out there. I am going to hit the road, Jack.

This is Alex Cooper. You can find and follow The MindsetCEO on LinkedIn or YouTube. Visit our website and book a call to see how I can help you on your journey from Founder to CEO.

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