My Story – A Meandering Path to a Career in Sales

I was not born a “natural salesman”.  Instead, I followed a meandering path that eventually led me to a career in Sales.

This is my story.

A Blissful Childhood, me at age 3 or 4


I spent my early childhood years in Tamaqua, a declining coal mining town in eastern Pennsylvania. Multiple generations of my close knit relatives lived within a few blocks of each other. I had Grandparents, Aunts, Uncles, Great Aunts and Uncles and cousins all looking out for me all the time.

In this small town (population 9000), everyone knew everyone else. My Grandmother was a former switchboard operator, my Aunt taught elementary school for 30 years, my grandfather had either worked beside or drank at the bar with all the men.

We were mostly lower class, blue collar families plus a few farmers who lived on the outskirts of town.

I loved living there. I had lots of friends, family, security and stability. It was a great place to be a kid. My career objective at the time was to become a truck driver so I could drive big rigs and blow loud air horns.

My parents divorced when I was 5, remarried each other a year later, and then divorced again for good when I was in 2nd grade.

Prior to this, nobody I knew in had ever been divorced. After their 2nd divorce, my father moved to another state and disappearing from my life except for the occasional birthday card.

My mother uprooted our family and moved us to the big city (Pittsburgh – population 500,000) at the opposite end of the state. I had to enter a new school system, make all new friends, and adapt to a completely different life.

Over the next decade, we moved 7 times and I changed schools 5 times.

Grade School and Chaos

Following the move to Pittsburgh, my childhood descended into chaos.

My mother quickly remarried after we’d relocated to Pittsburgh. This was an interracial marriage in the mid 1970’s- a first for my family and quite possibly for my entire neighborhood. Over the next decade, my stepfather moved 16 of his other children, 3 of his ex-wives, and several of his friends into our home for extended periods of time ranging from a few months to a few years.  Sometimes these boarders would overlap. Other times, it seemed like we had a constant stream of strangers moving in and out.

My stepfather was also a bully and a psychopath. Looking back on it now, I’m sure he was mentally ill.  He made our lives a living hell at times.

I entered the 3rd grade in a Catholic School as the “new kid”. This was a miserable experience. The nuns were so focused on order and control, I think they forgot we were kids and that school could be fun.

Luckily we ran out of tuition money after two years (a side benefit of being poor!) and I was able to transfer to the local public elementary school. I was put into the gifted program and thrived there for two years.

Not my house, but very similar

Middle School and the Ghetto

In the middle of my 6th grade school year, we moved again – this time to a dilapidated brownstone house in the ghetto that my parents wanted to rehab. We were the only white kids on the block and one of three white families in the neighborhood.

I was pretty oblivious to racial differences at the time. To me, the biggest differences between us and the neighbors was that I lived with 2 parents, we had a car, owned nicer clothes and I did well in school.

My friends had much less. Some lived with their Grandmothers or Aunts because their parents weren’t around. Some lived in the Projects. Many had been “held back ” in school.

Living in the ghetto wasn’t that bad – just different. Everyone was really poor in a way I hadn’t seen before.

  • We had a few neighborhood drunks who were kind of scary, but they mostly stumbled around or sat on the corner and mumbled at us while drinking out of paper bags.
  • Across the street was a house where they sold liquor from the side porch. Upstairs lived their demented grandmother who sit in the window and alternatively yelled obscenities at us or yelled “Hi Sweetie!” at us when we played in the street.
  • My next door neighbor was a weed dealer. He was one of the nicest (and mellowest) people I ever met. He was always cool to all of us kids and he kept drugs away from us.

The kids, for the most part, were just like any other kids. We rode bikes, played curb ball, roller skated and were outside a lot. We were fairly independent when it came to entertaining ourselves so we’d walk long distances to go to the pool, the park or downtown. We were broke but creative when it came to entertaining ourselves.

I lived next door to a community center. This place was an oasis for us. It was staffed by people on a mission to help poor kids. It was here that I played basketball, was taught how to play the drums, was bused to pools in the summer to swim, and learned to roller skate.

I have a few strong memories of adversity while living in the ghetto:

  • I started a new school in the middle of my 6th grade year. My mother told me that she had set everything up for us in advance. But when my sister and I arrived at school, the office had no idea who we were, had none of our records and wasn’t sure what to do with us. I had to register us, tell the principal what classes to put us in and help them obtain our records from our former schools.
  • When my school bus drove through the dark Corliss Street tunnels each day, pandemonium would erupt as kids jumped up to beat the crap out of each other because the driver couldn’t see what was happening. This happened every single day. I hated riding the bus.
  • I learned the verb “bricked”.  As in, “He called me a name, so I bricked him”.  The first time I saw one of my new friends throwing a brick at another kid, I was stunned. By the second time, I had learned that running away quickly was the best action to take anytime someone picked up a loose brick. 

The dreaded Corliss Tunnel

In the 3 years I lived in the ghetto, we were never robbed, seriously threatened or harmed in any way. I never heard any gunshots and rarely felt scared (other than on the school bus).

In fact, it was the exact opposite. Our neighbors cared for us and each other. Everyone looked out for one another and tried to do the right thing.

I have fond memories of many of my neighbors from the ghetto, who acted like surrogate parents for a whole bunch of us kids.

The only dangers and craziness I was ever exposed to came from within my home.

At some point, my mother had taken enough abuse and left my stepfather. We moved across town to a tiny apartment. Two months later, they reconciled.

When we moved back, my mother promised my sister and I that “things would be different this time”.  I knew things wouldn’t be different.We moved back and after a brief respite, the chaos began again.

It was at this point that I decided I needed to take care of myself.

I was in 7th grade.

My Escape Plan

I always knew I was smart. I started reading when I was 4. I was at the top of my class in school in any subject. I loved math and science. I aced every test – usually earning 100%.

I took every honor’s class and gifted program available at the different at the different schools I attended growing up.

Although my family life was chaotic, school was my anchor.

After we moved back in with my stepfather, I made a plan to graduate #1 in my High School Class. Then I would go to college on a Scholarship, graduate summa cum laude and become a successful Doctor or Lawyer. I knew Doctors and Lawyers made a lot of money. If I made a lot of money, I would be able take care of myself and provide security for my family.

Oliver High School – my home for 4 years

High School and Making Progress

We moved from the ghetto after 8th grade.  Once again, I left my home, my friends and my school. I started high school in yet another part of town as the “new kid”.

But by now I was used to this. I knew what to do. I got myself into the “gifted program”, excelled at all of my academic courses, and made new friends.

Home was still pretty unstable. My stepfather remained as crazy as ever. He had now moved 3 of his younger kids into our home semi-permanantly while fighting for custody with one of his crazy ex-wives who was in and of mental institutions.

But just like starting over in a new school, I was used to this too. I stayed away from home as much as possible, focused on doing well at school, and worked odd jobs to earn money to pay for clothes, books, and the occasional movie.

My high school sucked. I was fortunate to have had a few excellent teachers in the gifted program who really tried to educate us. But other than these teachers in this program, my high school was more like a zoo or a prison system. Perhaps others had a better experience there than I did. Mostly I felt like I was wasting my time there waiting for others to catch up. I always carried a novel to class with me so I could read something interesting whenever I finished work earlier than others. I was able to read a lot of books.

I’d rate my high school a 1 out of 10 for preparing me for college, for working, or for life.

When I was 16, my life changed dramatically. First, I received my class rankings and was #1 out of about 1000 students. Second, by now I had firmly established my reputation as the smart kid at school and with that came respect and recognition. Third, I met my first girlfriend.

And physically, I had grown from being a fat little kid into a man.

Day of Reckoning

In the late spring of that year, my stepfather once again was in one of his week-long abusive phases. He must have said something awful to my mother because my sister told him to “lay off of her”. He lost it and went after my sister. She ran to get away, my mother stepped in, and a fight began.

I was at a friend’s house at the time watching TV and being a part of his “normal family” when my sister pounded on the door yelling that my stepfather was going to kill my mother.

I ran down the street to my house. My friend and his older brother were close behind me. The front door was wide open, all the lights were on and we could hear from shouting inside the house.

My friend’s brother said, “Do we you want me to come in with you?”

(I will never forget that. His name was Guy Parsons. He was probably about 20 years old but he was right there ready to back me up. Thank you Guy. And thank you to the entire Parsons clan who treated me like a member of your family for many years. I’ll never forget your kindness.) 

I asked him to wait outside. I figured if he came in with me, my stepfather might go ballistic.

I ran into the house and got between my stepfather and mother who were having a shoving match. I looked at my stepfather and said, “Get out. You need to leave right now.”

Inside I was still just a kid. But outside, I was now nearly his size. Maybe it was something in my voice, maybe it was the rage that had been simmering inside me for years, maybe he just didn’t want to hurt me. Whatever it was, he stepped back and left with my mother screaming and throwing things at him in his wake.

I don’t really remember much about what happened over the next few weeks. I’m sure he came back home, everybody pretended nothing had happened, and things calmed down eventually.

What I do recall with clarity is that we left him for good a few months later. We moved into a crappy apartment a few blocks away and finally had peace at home.My mother divorced him and I didn’t see him again for many years.

Let the daily beatings commence

High School Graduation and College Failure

In 1986, five years after I conceiving my Escape Plan, I graduated as Valedictorian of Oliver High School.

It had never occurred to me to even consider any career path other than Doctor or Lawyer. Business was definitely something I had no interest in. I didn’t even know any businessmen. And Sales? No way! I hated selling candy for fundraisers and was terrible at it.

I chose Medicine because I was more interested in Science classes than English classes.  I also heard on TV that Law students had to memorize many cases and argue them in front of teachers.

I wasn’t good at public speaking and despised rote memorization,  so I chose PreMed with the goal of becoming a neurosurgeon. I took a heavy load of advanced math, chemistry and science courses.

I was totally unprepared for college. I had no guidance counselor, parents, or mentors to help me select my school, my major, or my classes. Instead I decided to attend the University of Pittsburgh because I wanted to stay close to my girlfriend and I heard it had a good Med School. And I joined Pitt’s  Division 1 Wrestling Team as a walk-on because I always wanted to wrestle and never had the opportunity to do so because my high school didn’t offer it.

At Pitt, I was no longer the “smart kid”.  I was one of 10,000+ students taking classes with up to 300 other freshmen. We were taught by professors who didn’t care whether we showed up or not. I was a commuter student, had lost my identity as a “genius”, and really struggled to find my way.

Wrestling was brutal and humbling. I’d arrive at 6AM for morning practice, go to class all day and then return for afternoon practice until 7PM. I rank this as one of best educational experiences of my life. I got my butt kicked every day for the entire season and was the worst wrestler on the team (by far). It was extremely tough, but one of the best learning experiences of my life. (Thanks to Coach Stottlemyer for giving me a shot here. When I asked to tryout he told me,  “We have no tryouts for the team. If you come to practice and work hard everyday, you’re on the team. But this won’t be easy.”  The lessons I learned on this team I still use today.)

Two years later, with 60 credits of advanced Math and Science courses under my belt, I found out that my student loans were being reduced and wouldn’t cover next year’s tuition (thank you Ronald Reagan). I hadn’t won any scholarships to help and couldn’t see how I was going to pay for college. I also no longer wanted to become a Doctor because I couldn’t fathom staying in school for 8 more years.

I had run out of money, enthusiasm, and direction.

I dropped out that summer.


In order to buy sneakers, clothes, and have money for going out, I started working when I was in high school.

I saved half my earnings. Between this and my student loans, I was able to not work (much) during my first 2 years of college until I dropped out.

Before and after dropping out, I worked a bunch of “McJobs”.

  • Mowing Lawns
  • Washing Cars
  • Industrial Cleaning of Giant Washers & Dryers for soiled Hospital Linens (truly disgusting)
  • Pizza Delivery and Short Order Cook. This is where I was taught the basics of customer service, sales, and being accountable.  It was here that I had my first taste of “variable income”. When we had a good night, I’d work really hard and my tips were higher.
  • Math Teaching Assistant  for underprivileged high schoolers taking Saturday classes. I was a college sophomore and hungover every day I worked there.
  • Lifeguard. This was a blast in the summer. I was like a babysitter for 100+ kids and worked with fun people my own age. I liked the money, the prestige, and the tan. It sucked in the winter when I was lucky to get 10 hours a week at an indoor pool.
  • Roofer, cement laborer and brick pointer – Brutal work with above average pay. My coworkers who were career laborers who urged me to go back to school before I ruined my “surgeon’s hands” and became a lifer like them.
  • Mail Boxes Etc. Assistant Manager – Essentially I was a retail clerk and box packer, but called a Manager so the owner could avoid paying overtime. To this day, I can pack anything and make the box nearly uncrushable (aka UPS proof).
  • Warehouse Manager/Shipper for a carnival supply and candy fundraising company. No job I’ve ever done since compares to the exhaustion and frustration of unloading an entire tractor trailer full of M&Ms only to have another trailer pull up to the dock 10 minutes later with a full load. No matter how bad work is today, it still beats unloading M&Ms.
  • New York TImes Newspaper Delivery –  As an independent contractor, I worked 7 days a week, 365 days a year, from 1AM to 4AM delivering the New York Times to rich people. What initially looked like a cake job paying me twice what I was earning as a warehouse manager ended up paying me less after self-employment taxes and vehicle maintenance were factored in. Not to mention, this job destroyed my sleep cycle, my social life and my digestion for the entire year I did it.
  • Plumbing Supply worker- My brother-in-law took pity on me and offered me my first opportunity for a real career. He offered a good salary, a company van, health benefits, vacation pay, a career path, coaching, and treated me like a valued employee. I couldn’t handle it. By this time I had been a college dropout for several years, was nowhere near my dream of becoming a Doctor and considered myself a complete failure. I was so ashamed of myself and envious of my brother-in-law’s success that I couldn’t seem to do anything right at his shop. I quit after 6 months.

Community College of Allegheny County

Night School

Shortly after leaving Pitt, I met my future wife. We fell hard for each other and created an instant family with me, her and her two kids. You’ll hear lots about them in other posts.



While working my McJobs and learning how to be a father to two kids, I attended night school taking transferrable requirement courses like History, Composition, Anthropology and Economics, while trying to figure out what I was supposed to do with my life.

(Thank you Community College of Allegheny County for offering fully accredited courses at a price that was affordable when I was making just above minimum wage. The teachers were excellent and attentive. The class sizes were small.  Attending night school with other working adults really helped me find my way out of a life of poverty.)

At about this time, PCs were becoming affordable for the average person. I was broke but thought, “I need to learn how to type on a computer so I can submit my college papers”. I took a non-credit course on WordPerfect. By the 3rd class, I had blown past all of my classmates and was creating my papers easily. I spent the rest of the classes teaching myself how to use more advanced capabilities of Word Perfect while my classmates struggled with the basics.

Then I heard about a program called Lotus notes, which was used to create tables and spreadsheets. I was told that everyone needed to know how to use it. So I signed up for another non-credit course. As soon as I started creating two dimensional tables and manipulating rows, columns and functions, I was hooked. Once again, I blew past my classmates and was using Lotus notes to create tables and charts that I used for home and work projects.

Around this time, it occurred to me that I was pretty good with computers. I took one final noncredit course on dBase to learn about databases. I had a similar experience, and had an epiphany.

My New Escape Plan

I decided I had a knack for this computer stuff and would become a computer programmer.

I refocused my night school classes toward a BS in Computer Science. I also decided to quit my brother-in-laws plumbing business and get a job as a Bike Messenger in downtown Pittsburgh.

My family thought I was nuts. My secret plan was that I could use this job to get introduced to a lot of business in downtown Pittsburgh and talk one of them into hiring me for some computer related position. This way, I would gain work experience “in the industry” while I attended night school and got my degree in computer programming.

Luckily I hadn’t run this plan by anyone wiser than me. Otherwise, I would have been told how unrealistic it was.

Believe it or not, it worked.

Into Sales

Four months after becoming a Bike Messenger, the Pittsburgh Computer Store ran an ad for a warehouse manager.

I responded to the ad in person with a copy of my resume. I was still in full messenger gear. I had an impromptu interview with the manager and sold myself really hard.

That night I returned home excited to tell my wife that the manager really liked me and I really felt good about the interview. She broke the bad news. The manager had already left a message saying he had to give the job to another employee’s son.

I was disappointed but figured I’d keep biking and find another job. A few days later, the manager called me . He said the other guy didn’t work out and if I wanted the job, it was mine!

This was when my career trajectory turned around. As warehouse manager, I was taken under the wings of our technicians who taught me how to repair Mac computers and set up networks. I worked all day, attended night school taking programming courses and learned how to fix and install computers.

A year later I asked the manager if I could move into one of the open Sales positions. I had given 150% proving myself to be a hard working and enthusiastic worker. He gave me a chance and became my first mentor.

With lots of help and coaching from my manager and the more experienced sales reps, my income doubled in a year.

  • I started a side consulting business doing installations at night.
  • 3 years later, I moved to IT and Tech Sales for an Advertising Agency.
  • Then I joined a startup ISP as an Account Exec.
  • From there I was promoted to team lead, Manager & Director
  • I worked for several more startups, a Fortune 1000 and today run my own business.

Lessons Learned

Looking back, I realize that I learned something from every failure, every adversity and from many people. Here are a few people I want to mention:

  • My teachers, friends and neighbors. They’ll never know how their encouragement and support kept me going when times were tough at home.
  • The pizza shop owner who taught me to answer the phone like I was glad the customer was calling, instead of my feigned “I’m so cool, I don’t give a shit attitude”.  I did care. I was just an idiot.
  • The roofing laborers who taught me that my fantasies of earning “big bucks” as a laborer and quitting the college thing was stupid and that I needed to do something else for a career.
  • The computer store manager who gave me exactly the mix of trust, confidence and challenges I needed, at exactly the right time.
  • My wife, who stuck by me when I was an unemployed, broke, college dropout and who remains my biggest supporter, my best friend, and the love of my life.
  • My mother, who surprised me by giving me her car when my transmission was shot and I needed a vehicle to deliver the NY Times. She had almost nothing, but she gave me her car so I could earn a living.

There’s a lot written about effort and hard work. “Pull yourself up from your bootstraps” is a common phrase. We admire self-made men and stories of overnight successes.

Well that’s not how success came to me.

It came as a result of hard work. It came from lots of failures. It came from being in the right place at the right time. It came from getting a hand up from many people along the way. It came from a loving wife and supporting family who stood by me through a decade of struggle. It came from recognizing opportunities and pushing through my fears to go after them.

It’s our job as sales managers to help our Reps build their skills, work through challenges, and develop their abilities to give sustained, effort. Then it’s our job to help them recognize opportunities and act on them.

Perhaps, it’s our job to do the same thing for everyone we encounter. You never know who might turn out to be a future Sales Rep.

I’m grateful to the people in my life who did this for me.


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