Michael McCafferty: Entrepreneur, Sales, and CRM

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Michael McCafferty is the epitome of an entrepreneur. Now, I have to admit I am absolutely bias in that I have known Michael for nearly a decade and he has been a mentor during some very interesting times throughout these years. What I always admired about Michael was his honesty and straight-forwardness. He always challenged me to think about solutions and never sugar coated things.

I was recently thinking about entrepreneurship and some of the people that I considered brilliant sales minds and pioneers in the CRM space. Michael McCafferty is one of the top on this list.

Michael was kind enough to allow me to ask him a few questions regarding a variety of topics around entrepreneurship and technology and this is what he had to say:


Jorge: When did you realize that you were an entrepreneur and how did it happen?

Michael: That’s like asking a fish when he realized he was swimming in water. My father was an entrepreneur. So it may have been genetic. I actually started one of my first businesses, A local bicycle repair service, at the early age of 9 years old.

I think that being an entrepreneur is really an addiction. I mean, imagine this: the ability to create a new life form, starting with only an idea, and build it to the point where it makes money and helps people. That, for me, is a real rush, just as much as racing cars and doing aerobatics.

Jorge: What is your professional background?

Michael: Well, the short story is I’ve been a successful serial entrepreneur, software developer, computer and software sales, and marketing professional.

The long story is that I started a few different businesses in college and one summer sold encyclopedias door to door. It became clear to me that I really liked selling stuff. There was something very magnetic about engaging a complete stranger and then only after an hour or two of conversation, was able to receive a real paycheck from your efforts.

In 1964, nearly fifty years ago, I just barely graduated from college at the bottom of my class – and in a most epic fluke, I got the best job offered to anyone in the graduating class. The job was with IBM and the position was a computer salesman. I was receiving a great salary plus commission. I instantly fell in love with the whole concept of computers and software and how they were the future of everything. Over the next 3 years I sold a lot of computers, then quit to start my own computer services company.

At 25, I talked my way into a job as a programmer for a computer parts manufacturer. I wanted to learn how to program so I could start my own service bureau. I wrote a lot of software for that company (in FORTRAN). The president and I got the board approval to fund my startup idea my way.

At 26 I was the CEO of a new startup subsidiary of the Amex-listed parent. I was driving a Jag XK-E roadster, living large, and having great time. Moving forward I wrote a lot more software (in COBOL), and built a very profitable 3-shift operation doing payrolls for a few thousand companies in the Philadelphia area. After 7 years of building a super company, the president died suddenly, the board would not honor his stock agreement with me, so I left with nothing.

Photo Below: San Diego, CA

MM photoAfter that, I found my way to San Diego and started over from scratch. In 1979, I invented the first “electronic yellow pages”. Which was way ahead of its time. Google re-invented it in 2004 as Ad-Words.

Then I invented TeleMagic, which as it turned out, was the first of a new category of software products that would later be labeled as contact management software​ or CRM (customer relationship management), or sales automation software. I programmed the early versions, built the company over 7 years and performed an exit of happy proportions.


Photo to the Left: A snapshot of Michael’s car collection

This was the start of the “Period of Wretched Excess”, and Fun, including Ferraris, airplanes, fantasy homes, travel, and “stuff”.


MM Bank

Photo to the Left: An old business card from the bank

Then I started a bank, and got back out just before the financial crisis.

And for the last 10 years I’ve been mentoring startup entrepreneurs, and loving it.



Jorge: I have heard you referred to as the Godfather of CRM due to the founding of TeleMagic. What was CRM like back then, what drove you to invent TeleMagic, and how have you seen CRM evolve since then? What is the future of CRM as you see it?

Michael: It was 10 years before the Internet. The software was very primitive compared to what is being done today, and the hardware was not as reliable. TeleMagic was designed to mimic a shoebox full of index cards with customer/prospect data. Of course it was way more powerful because it could dial the phone and send letters and faxes and even interface with other software. It was pretty revolutionary software and helped many sales people sell a lot.

What drove me to invent it? — To me it was an obvious use for a personal computer, but such software didn’t exist and I decided to write it myself.​

CRM hasn’t changed much at all over the years, except recently with integrations into social media sources.

If you view it from the user’s perspective, CRM today is just the same old concept but running on more devices, and the Internet.

As for the future of CRM, I will only predict that if I have anything to do with it, the future will be very interesting!


Jorge: What does “sales” mean to you?

Michael: Sales is doing whatever it takes to get to the point where the customer smiles and the cash is deposited in your bank account. It is telling the story in such a way that the prospect becomes customer.

Recommended read: “The Greatest Sales Stories Ever Told: From the World’s Best Salespeople”


Jorge: You have worked at startups as well as big companies, what would you say are a few of the major differences in their approaches to “sales”?

Big companies play defense. They are slow to act.

Startups must offense. They need to be fast.

Big companies have defined sales processes.

Startups are trying to discover a sales process that works.


Jorge: What are 3 sales or marketing mistakes that you see early stage founders make and how can they avoid making them?

Michael: Only 3? Ha! I think most of the mistakes in sales and marketing can be traced back to inadequate Testing. Most startups have preconceived ideas on product definition as well as price, terms, and other variables. But they don’t adequately test those assumptions, which are almost always sub-optimal and could easily be the difference between success and failure. The solution is to let the data determine the policy. Test many different approaches, headlines, calls to action, prices, colors, terms, packaging, etc. Continuously test innovative ways to improve sales.


Jorge: Please share anything about Michael McCafferty, your current projects, etc — that you want our readers to be aware of.

Michael: I really enjoy working with startup entrepreneurs to help them achieve their vision. Well, that and playing frisbee on the beach…