My first day as a salesman out of the office... Felt like I was playing hookey

At 24, my entire work career, if I could call it that, was centered around a haphazard collection of temporary jobs, and the kinds of work you get when you are trying to find work on the side; waiting tables, catering jobs over the holidays, painting houses and cleaning up yards. I sometimes quit these jobs without notice because they were crummy. I struggled with getting places on time, or remembering when my shift was, and got fired a few times, too. 

I wanted to work in an office, as I had always imagined I would. I had typing skills, after all, from my work as a newspaper editor and writer in high school and college. I was looking for office work, but the jobs that I had gotten through summer work and internships came through connections I didn't want to access again. And no one wanted me; scouring through help-wanted sections and the classifieds didn't yield anything. A friend suggested a temp agency they had success with. I went in, interviewed, and the next day I was working! 

I also had AV Tech skills, and that turned into my first "real job," a great job with great benefits, but I was a chronic grass is greener type of guy, and I soon left that job for a clerical career in the mortgage business, a multifamily lender, then a residential lender as a clerk, and then a manager. There I got firsthand knowledge of the real money in business; sales! These were the guys with fancy cars and nice suits, not like me sweating behind a cubicle desk grinding for hours in a low-level glorified manager's job. 

People told me there was too much risk; I wasn't guaranteed any money in sales. But didn't worry about that. I had already gotten business that I had to turn over to another loan officer, and the sight of the commission check gave me intense inspiration. I was ready to set out. No one wanted to hire people without experience, but I traded a contract helping a company set up their closing department for a position as a loan originator. I never looked back. 1 month into the job I was near the top of production. 

That first day, stepping into the cool autumn air, I kept feeling like I should go back to the office; like I was cutting class. I literally skipped into my first appointment. A year later, headhunters were calling me offering me jobs. I had established myself. "Go ahead, fire me! I've got clients, and I can work anywhere." It wasn't even about the money. 

I'll never choose a job where I have to do exactly what someone else says and control when and how I work ever again. Even though the sky was the limit, I would rather make less money and not subject myself to the office. 

Imperfect Information - First Signs of Entrepreneurship

I can't remember if I told this story before, but in second grade, at my elementary school, I became fascinated with the school store and the supplies they sold. In the morning and at lunch there was always a line for supplies, and I was a frequent visitor because I was absent-minded and lost or forgot my pencils frequently. 

I could buy 10 pencils for $1. But they only had several hundred. I imagined that, if I bought all of the pencils, the students would have to come to me to buy pencils and I could charge a profit. I set about collecting my allowance money, spare change and savings to execute my purchase of all the pencils.

On the morning of the purchase, I expected that I would buy all the pencils and stand by the store to re-sell them to desperate students for 25 cents each. The morning store hours were less popular, so I figured I would purchase all the pencils at the close or the morning hours, that way, when the long line for pencils formed at lunch, I would tell the students that they would have to buy from me, at $0.25. 

The purchase went fine, but during my first period class I was called to the principal's office. He said, "I know what you're trying to do. It won't work. I can buy more pencils." He was kind in offering to buy back all the pencils I had bought. This is an example of imperfect information. I didn't know how easily I could be wiped out. 

The Budding Entrepreneur - Lessons learned and lost

At the age of 10, I embarked on my entrepreneurial journey with a simple, yet captivating hobby: stamp and coin collecting. This early interest was more than just a pastime; it became a foundational lesson in understanding the relative values of things. However, during this initial foray into the world of collecting, I overlooked a crucial principle of capital: the importance of building and preserving it. This vital lesson would only come later, inspired by insights from the book "Rich Dad Poor Dad."

By the time I was 13, my entrepreneurial instincts had evolved. I started visiting the local coin store in my neighborhood, drawn to the challenge of collecting various coins from each U.S. vintage and mint. My collection grew to include pennies, nickels, dimes, quarters, half dollars, and the more expensive and widely collected silver dollars. While these silver dollars were already recognized as valuable commodities, I saw unique worth in the smaller denominations, still in regular circulation, especially the rarer ones.

It was then that I stumbled upon a golden opportunity. I realized that certain coins were particularly hard to find, making them rare and valuable. To acquire these, I came up with a creative solution: I offered to roll coins for my neighbors. This wasn't just a service; it was a strategic exchange. I would do this for free, but with one condition – if I found a coin that was missing from my collection, I could keep it. This innovative approach not only helped me complete my collection but also taught me the art of finding and exploiting market niches, and the value of offering a service in exchange for goods.

My collecting strategy evolved significantly as I accumulated more capital. I began to "buy" rolls of coins from small, local banks, which proved to be a goldmine for my endeavor. Unlike the larger banks that traded coins directly from the mints, these small savings banks handled coinage that had circulated among the local businesses and residents. This meant they often had a variety of interesting and potentially valuable coins.

As I frequented these banks, the tellers began to recognize me. I was the kid who wandered in with a purpose, eyes always searching for that next valuable find. Some of the tellers, realizing what I was up to, even started tipping me off about promising coins in their drawers. This inside knowledge was invaluable and often led me to some of my most prized acquisitions.

My focus wasn't just on collectible coins, which held higher value when uncirculated, but also on finding silver coins, which had a metal value and could be sold as scrap. Up until 1964, most U.S. coins were made with real silver. I developed a skill, almost an ear for silver, which became an integral part of my strategy. I would pour a bowl of coins onto a glass tabletop and listen attentively. The unique, high, sweet notes of silver clinking against the glass were unmistakable. This method became a reliable and almost magical way to identify silver coins amidst a sea of regular coinage.

This period of my life wasn't just about collecting coins; it was a formative time where I honed my skills in identifying opportunities, building relationships, and using every available resource to my advantage. It was a clear demonstration of entrepreneurial instincts, even at a young age. The thrill of the hunt and the satisfaction of finding those rare gems were exhilarating, but more importantly, these experiences were building blocks in my understanding of business, investment, and the value of knowledge and relationships.

I should have continued my coin collecting, steadily building the value of my holdings and becoming systematic about harvesting rare coins from circulation. However, when I turned 14, I made a decision that I now regret. I sold all of my coins to buy something that, in hindsight, held no real value - typical teenage spending money. The author of "Rich Dad Poor Dad" would have been so disappointed in me. By liquidating my capital, I was left without the resources I had built up.

This meant I had to start from scratch, taking on odd jobs like lawn mowing and yard work. These jobs, while honest, were time-consuming and physically demanding, and my earnings were directly limited to the amount of spare time I had. The returns from these jobs couldn't compare to the potential growth of my coin collection.

If I had retained my collection, maintaining discipline in only liquidating small portions when necessary and prioritizing the growth of my capital, things would have been different. I wouldn't have had to resort to manual labor for income. More importantly, I would have had more time to brainstorm and implement new ideas for growing my capital. This early lesson in the significance of preserving and wisely managing capital was a tough one, but it profoundly shaped my understanding of investment and the value of long-term thinking in business.

But, despite this early lesson, I didn’t learn from it. In a pattern that became all too familiar, I repeatedly made the same mistake. Each time I accumulated a bit of capital, whether from odd jobs or small ventures, I found myself spending it impulsively on things that offered immediate gratification but no lasting value. This cycle of building and then diminishing my resources became a frustrating theme in my entrepreneurial journey.

If I had had a mentor, someone to coach me and guide my financial decisions, my journey might have been vastly different. This mentor could have been a person with whom I could honestly share my earnings and progress. They would have emphasized the importance of retaining and growing capital, steering me towards activities that generated wealth instead of spending it. Unfortunately, I navigated these formative years alone, making decisions without the benefit of experienced guidance.

This pattern of self-reliance, of keeping only my own counsel, is something that has repeated itself throughout my life. In "Rich Dad Poor Dad," the author discusses the pivotal role his mentor played in his life. His mentor didn't just offer advice; he actively involved him in meetings, guided his investments, and kept him on track. That level of engagement and practical guidance was something I sorely missed.

I realize now the significance of having entrepreneurial role models. While I did see a few other kids engaging in similar ventures, there was no structure, no guiding force to show us the way. The absence of a mentor, someone who could have offered real-world wisdom and practical advice, left a gap in my learning. It meant that I had to learn everything through trial and error, a path that was often inefficient and filled with missed opportunities.

Indeed, this is the paradox at the heart of entrepreneurship. Initially, there's a sense that the entrepreneurial journey is about rugged individualism, about having a unique idea and pursuing it in solitude, separate from the rest of the world. This perspective is particularly strong when those around you don't recognize or understand the value of what you're doing. It fosters a belief that success is a solo endeavor, driven by personal vision and effort alone.

However, over time, my understanding of what it means to be an entrepreneur has evolved dramatically. I've come to realize that the essence of successful entrepreneurship is quite the opposite of solitary endeavor. It's not about going it alone; it's about the power of networking, seeking constant feedback, asking for advice, and, most importantly, being receptive to that advice.

The most successful entrepreneurs are those who understand the value of collaboration and mentorship. They surround themselves with knowledgeable people, learn from others' experiences, and are not afraid to share their ideas and seek guidance. This networking is not just about making business connections; it's about building a support system that can offer diverse perspectives and advice.

In my own journey, the shift from seeing entrepreneurship as a lone pursuit to understanding it as a collaborative process is transformative. It highlights the importance of community, mentorship, and the continuous exchange of ideas. This realization that entrepreneurship thrives in an environment of shared knowledge and mutual supports is crucial.