A Blog On Cold Calling

I love cold calling.

In the beginning, I became a cold caller for the noble reason that I was bored and wanted a new challenge. 

For the five preceding years I’d been an Account Manager for a Fortune 500 software company, supporting a dozen-or-so existing clients as they sought to maximize their million dollar investment(s) in my company’s software. I worked a lot of hours, traveled a lot of miles, had a lot of meetings, coordinated a lot of high tech conversations, hosted a lot of expensive meals using a seemingly-limitless expense account, and basically marveled in the fact that I was paid nearly three times the amount of money that I’d made in my previous career as a teacher.

Then boredom reared its ugly head.

I remember loving golf so much as a teen-ager that I golfed three times per week rain or shine all throughout high school into college, then suddenly one day at the age of 20 I was in the middle of a round on a bright Spring day and thought, “You know, I’m bored with this.” I’ve only golfed a handful of times in the three decades since that moment. And so it was with my being an Account Manager. One day I was in a meeting with a terrific Director Of IT talking about his strategic direction over the next year and suddenly thought, “I’m bored with having the same conversations about the same issues about the same products with the same (great) clients over and over again.” About a week later fate intervened in the form of a former colleague who called me out of the blue: “Hey, my friend who’s a VP of Sales called and needs someone who can work with Fortune 500 clients but isn’t afraid to cold call — are you interested?” You bet I was!

Three weeks later — in late 2004 — I was no longer an Account Manager with a F500 company and instead was employed by a tiny company selling software that no one had ever heard of before, armed with only a desk, a laptop and a phone, and expected to drum up more than a million dollars in new business over the next 12 months by way of cold calling. Thankfully, since I had a young family and mortgage, I did it. And, to be honest, I’ve never looked back. 

Even today, 20 years and 30,000 cold calls and more than 50,000,00 in signed (new client) contracts and a new industry (real estate) later, I still cold call. In fact, I have a sick joy in cold calling. Because cold calling is slightly thrilling, not unlike playing sports where I’m hoping to score points or make a steal or have some kind of fleeting momentary success on the field. And because in 2026 it still works despite all the many claims otherwise. And because at the end of the day it restores my faith in humanity, because although there are a few rude or curt people (recently I was lectured about the fruitlessness of cold calling by someone who didn’t like that I was cold calling them) the OVERWHELMING MAJORITY of people not only are polite but actually downright friendly when I reach them. 

There are people I worked with 25 years ago who 25 years later are still having the same conversations with the same handful of clients making >300K per year for large companies (AWS, Microsoft, Oracle etc. etc. etc.). How much I admire their ability to do that. For me, I can’t imagine. I like new challenges, and meeting new people while continuing to embrace my existing connections. In short, I like to cold call. 

What follows are my random thoughts in no particular order as I cold call. Posted here because I enjoy writing and I enjoy posting for no other reason than enjoyment. I retain all rights (e.g. if someone turns this into a movie I want a cut 🙂 ) but accept zero liability (in short, use at your own risk). 

Thank you for humoring me. 

I can be reached at fromthedeskofrob via gmail or LinkedIn (https://www.linkedin.com/in/rob-mathison-43779b/)