Me and My Son While We Lived in Miami

Isaac Schultz was a character. Jewish guy from Ohio that had worked his way up the ranks to be the head of publisher sales for Miami New Times. 

I worked for him while beginning my sales career in Miami, and working for him was hard. I spent almost three years cold-calling businesses door to door in the South Florida heat trying to get them to place ads in the magazine and website. The worst months were July and August. A lot of the small businesses closed, and Isaac was ruthless about performance.

But, I was learning. I was learning how to build value into my pitch. I started just asking clients for money, but soon I was coming to prospective clients with ideas of how their brand’s message could fit into our publication. I started to understand which businesses would place ads, so I wasn’t wasting my time with the wrong customers. 

Isaac was a tough boss. Everything was about the numbers. Sales reps were let go on a bi-weekly basis for not performing. He was also one of the most charismatic salespeople I’ve ever met. He loved his job. He was a hard-core conservative working amongst the most liberal paper in the city. 

I tried to leave the job for another job, but Isaac said he’d offer me more money. I told him if he mentored me, I’d stay. There was so much I could learn from him about the craft of selling. 


He terrified me in some ways. He was ruthless with customers. I saw him demand money from small businesses that were going out of business. He was selfish. At our events, I saw him make out with the younger sales reps that were starting their careers. The girls had no hope of resisting him since he was so high up in the organization. He was dangerous. 

The newspaper and magazine industries were dying, and I knew I had to make a move to digital media. At this point, it wasn’t about money. It was about learning. The market was changing and the majority of ad spend was now headed to Google. I knew I had to get into a position to learn about Google if I was going to have a strong future career, and I finally found an opportunity. 

The problem was the job would pay me less than I was currently making. It was a payout.

I went to Isaac to tell him I was leaving for the digital job. He offered me another pay increase. But, it was time for me to go. At this point, I had learned all I could from Isaac and the Miami New Times. 

I knew my career didn’t need more money, it needed more learning. If I wanted true control of my career, I needed autonomous skills that were unique in the marketplace. The skills of placing print ads were limited compared to what the digital advertising industry could teach me.

This was the first time I took a job for less than I was making, but it wouldn’t be the last. To me, learning trumps money in the short term.

Eventually, the learning will attract the money, especially if I’m learning a unique set of skills that are difficult to replicate. For me, the job for the digital advertising company eventually led me to a job where I make 10x what I made while working for Isaac because of the unique skills I developed. I think its important to take the long view when thinking about money and building a skillset. 

A career is about skillset, not about money. I believe its important to make myself useful to the market with a unique set of skills to really help people. Money will follow the unique set of skills, and I’ve seen that be true over and over in my career. 

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