⚡️ Today’s level up ⚡️

Today’s edition continues the breakdown of my complete journey from childhood, through my time in sales, to today as a one-person business operator with over a $5M net worth and the freedom to follow my ambitions on my terms. My goal is to illustrate how being highly purposeful throughout this journey has yielded financial independence, solid relationships, improved health, and memorable experiences.

Let’s go!

Read time: <15 minutes

If you missed last week, read it here.

“When you expand your focus and zoom out to see the bigger picture, you can become aware of the ideas, or options, available to you.” – Dan Koe

Disclaimer

As I mentioned in Part I, this is another in-depth edition, similar to this one and this one.

However, I feel the depth is important in order for you, as the reader, to zoom out and ponder the bigger picture. Don’t be afraid to step away from the noise and chaos of modern life to ask yourself the big, hard questions:

– “What am I doing?

– “Why am I doing it?”

– “Where am I going?”

– “Who really matters to me?”

 – “How do I feel about my progress?”

– “When am I at my most confident and why?”

My hope is that by openly sharing my (humble-ish) beginnings, my struggles, my failures, my learnings, my accomplishments, my habits, my systems, my thoughts, and my beliefs it can help reframe and energize your own approach – especially if you associate with being different, ambitious, weird, anxious, traumatized, sensitive, curious, quiet, introspective, intentional or frankly any label that helps you feel like you’re discovering yourself but still aware of the fact that there’s still a long journey ahead.

“If you don’t choose where to place your focus, it will be chosen for you.” – Dan Koe

This edition will pick up where I left off last week (as a young adult). I’ll share my journey once I entered the professional sales arena, and ultimately, chart where that career path has landed me today. I have attempted to simplify this path into three distinct phases, or as I like to think of them, Levels.

Within each Level, I will describe what they mean to me and deconstruct the key concepts, principles, and missions accomplished within each one. I will also try my best at explaining how it all ties together in being more purposeful with your performance so that you have the power to take control of your career in sales and use it as a vehicle to architect the life you’re fully capable of living.

For practical purposes, let’s divide the business world into two simple categories:

1. Labor workers

2. Knowledge workers

Labor workers have an important role in the economy. They keep you fed, cut your hair, keep the lights on, deliver your packages, make the things you’re wearing right now. However, the tradeoff of working in this category is that earnings (and eventual financial freedom) is restricted to trading time for money. Miss a week at the salon? That means potentially missing out on dinner next week. That’s the harsh reality for billions of people on this planet.

Knowledge workers, however, use their brains more than their bodies to produce outcomes. Sometimes, those outcomes can be on a scale that delivers outsized earnings. Meaning there isn’t a direct correlation between time spent and income earned. Being in the knowledge category is incredibly precious.

Chances are you’re in the knowledge worker category.

The most ubiquitous tool every knowledge professional uses is the calendar. It can efficiently determine what you have to do, when you have to do it, where it needs to be done, who it needs to be done with, how it needs to be done, and even why it needs to be done.

I’ll use calendar ownership to inform our path across the three levels. I hesitate to use specific numbers for each level, but directionally it looks something like this:

– Level I calendar: Mostly others controlling it (~80% others / 20% you)

– Level II calendar: A combo of you and others controlling it (aim for at least 60% you / 40% others)

– Level III calendar: Mostly you controlling it (start above 80% and eventually get to 100%)

Let’s continue with the journey I took through these stages, starting at Level I.

Level I: The LEARN Stage

“In a practical sense, you do not understand your potential because you have not sought to learn by your own desire.” – Dan Koe

In the spring of 2006, I had been at Coastal Soccer for over three years.

I was one of the first employees (when we were a company of just four), and by that stage, we had grown to over 50. I was 26. Being a pro soccer player was long in my rearview mirror, and I even felt soccer training and education was coming to its end.

I was still living in Jamaica, Queens at the time. I felt like I was living two lives – because in many ways I was. In the morning, I would drive a reverse commute from Queens to Nassau County on the Long Island Expressway (or Grand Central Parkway, depending on which one had less traffic) to work in a small office we had in Hicksville.

Then around 2:30 PM, we would all head out across Long Island to get set up for training our first team. We’d often have three to four teams to train each evening, and in my case, I’d also do 1:1 or small-group training sessions on top of team training.

I’d get back to my apartment between 8 or 9 PM, shower, have a quick bite to eat, and then hop on the F train for about 45 minutes to get into lower Manhattan or Brooklyn. Sometimes it would be for fun, meet up with friends, have too many drinks, and get home way too late. Most times however, it was to work my second job as a budding DJ.

I took whatever gig I could take.

But the cool thing, and downside of New York City, is it never (well, maybe barely) sleeps. Most bars or lounges I spun at closed at 4 AM. That meant I was averaging less than 3 – 4 hours of sleep each night.

It was a true grind.

It’s hard to be fully conscious when you’re that chronically sleep deprived, but I was desiring entrepreneurship. Working for a few years at Coastal Soccer and being a part of building out a brand identity, a distinct training methodology, and ambitions to create a repeatable model were valuable skills to learn.

I even learned valuable sales skills, even though I wasn’t in a specific sales role.

But the cracks were starting to emerge. Burning the wick at both ends and the constant fatigue meant my performance for the company and on the field was taking a drastic dip. I was let go as a Manager, but given the option to continue to train a handful of teams.

As you may remember from the last edition, I was also racking up significant personal debt. My parents helped out at times, but it was getting untenable, and I didn’t disclose just how much personal debt I had been accumulating.

I didn’t have a plan. I just had some half-baked ideas.

By that time, I was good enough on the turntables to get regular gigs, and then parlay those gigs into higher-paying ones (like weddings and parties for people who didn’t want the typical YMCA-slinging DJ and MC). I thought I could start my own DJ business and carve out a niche for myself.

As I discovered in my soccer endeavor, it was easier said than done.

The pressures to pay rent and bills and keep up in NYC was just too much to handle for a budding business in a crowded market without a solid business plan. I had to do something, and quick.

While I was practicing at Scratch DJ Academy, I learned of a job opening in their office. It was basically setting up the equipment for more experienced DJs at stores and venues across the city. I spent a couple of months in that role. Being in the office more, meant exposure to the founder, Rob Principe, and other executives, like Mike Cannady.

They could see I was a little more “different” than the other equipment techs – different style, hyper-organized, a little more educated. They asked me if I had any interest in becoming an Account Manager for a growing segment – which was using DJ talent to program background music for marquee brands. They had just won Gucci as an account and the old AM had flown the coop.

Timing is not everything, but it’s damn helpful!

So in August of 2006, I got my first official role in sales, and it changed everything for me. Part of my role was managing and growing existing accounts (come on, you can’t ask for much better than Gucci as your first account) while also pushing into new accounts.

I didn’t know the first thing about business development – at least from a hard skills perspective. Mind you, I was still several thousands of dollars in debt, so I was also DJing on my own at night to pay the rent. At least I finally had a decent paycheck I could rely on and some health benefits to boot.

So after work and before my gigs, I’d end up at a bookstore on Sixth Avenue in the West Village or the Barnes and Noble in Union Square to read up on sales books (I felt too broke to buy them), but I did end up buying two from Jeffrey Gitomer – Little Red Book of Selling and Little Green Book of Getting Your Way.

I couldn’t tell you anything specific as it relates to specialized sales skills from those books. However, the one thing that stood out to me (odd at the time, but makes perfect sense now) is Gitomer recommending that you purchase your name as a domain. In 2006, that was a pretty novel concept to be teaching salespeople.

I didn’t follow that advice until much later.

I had to cold call. I had to cold email. I had to be persistent. All while keeping the standards high for our current clients – which had grown for me: Gucci, Royal Caribbean, CRUNCH Fitness, Sandals & Beaches Resorts, and brands I was able to win, Wet Seal and Arden B.

At this point, I was at least paying my rent on time, but I was still working hard in the office and DJing late into the early morning at least three nights a week. It came to a head in the spring of 2007 when Angelo D’Agostino, then Creative Director of Arden B, swung by our office for a quick meeting.

I ended up having a panic attack in that meeting. When it came time for me to present, I froze. I had a rush of blood to the head. I was dizzy, confused, my chest was tight, drenched in sweat, and I couldn’t form words. I didn’t know what the hell that was. I just thought it was me getting nervous (when I didn’t have a real reason to).

The constant hustling and grinding was taking its toll.

Fortunately for me, there was light at the end of the tunnel. Later that spring, I started chatting with a cute girl on MySpace. We had a mutual contact, Cornelius (he went by Conor). Conor and Lisi went to Syracuse together, while he was also a friend of an ex-girlfriend of mine. He also happened to be a part-time DJ, and that’s where we had formed a bit of a bond.

Lisi and I finally met up one hot and rainy evening in late June.

We started dating. I knew there was something special there, but was stubborn and almost walked away a couple of times in the early months. Luckily, she saw something in our future together, and slowly but surely, I started opening up to the possibility of a life together.

A fun night out in NYC in the early days with Lisi

When we met, Lisi was finishing up nursing school. She had been a former fashion designer, but like many industries popular in NYC, the grind and competition was tough. She decided to pursue something more stable.

After about six months of dating, we started to get serious.

I left my apartment in Queens, as by that point, my life was in Manhattan – Lisi, work (Scratch), more work (DJing), and some play. I was doing okay in my role, but there wasn’t a clear future for me there. In fact, with mounting debt, a desire to settle down, and Lisi starting a new career as a nurse, we were wondering if we even had a clear future in New York.

During Lisi’s spring break in 2008, we went to visit her hometown of Sarasota, Florida.

It was late March, the weather was perfect, and as we were sitting on the beach toasting to a gorgeous sunset as dolphins were literally swimming by in the Gulf of Mexico, we both asked ourselves out loud: “What are we doing in New York?”

As luck would have it, Lisi’s grandmother’s condo on the beach had been recently vacated for her to move into a senior community. It was owned by Lisi’s dad, and we proposed the idea of moving in, freshening things up a bit, but more so, to get settled and gain a head start on our next chapter together.

I moved down first in late August of 2008, and once Lisi passed her NCLEX exam to get her R.N. license, she joined me. We got engaged in September, married by law in November, and then had our celebratory wedding ceremony with friends and family in April, three days before my 30th birthday.

We missed NYC, especially our core group of friends, but life was infinitely easier in a small, more affordable town. By that point, I had declared Chapter 11 bankruptcy. My credit was shot – for the following seven years at least.

I no longer had any credit cards, just a card I could preload with funds to use as a credit card so I could begin building my credit worthiness back up. Everything major – from getting our first car, a Toyota Yaris, to flying on planes to see my family was all done on Lisi’s credit cards.

On the job front, I had to try to secure something before moving down. It was as an Advertising Account Executive with Creative Loafing, a regional free paper that highlighted weekly activities and local businesses.

I was back on rung one on so many levels.

At Scratch, it wasn’t an enterprise motion to selling, but it was a slower method – akin to how ad agencies win businesses to manage their creative or ad budgets (or both). At Creative Loafing, it was eat what you kill, and the only way to kill was to go knock on doors (literally).

It was painful, but I did it. However, I was trying to be too strategic for my boss’s liking. In three months, I had only sold two small ads. I saw the writing on the wall. Either I go find something new, or I’m going to get fired.

I ended up moving over to the larger newspaper in town, The Sarasota Herald-Tribune before I got the axe.

It felt like a better fit. It was selling digital solutions through a joint partnership between Monster.com and The New York Times (who was the Herald-Tribune’s owner). It meant pursuing slightly larger businesses (those who had a sizable workforce). More importantly, I had a manager in Denise, who was as eager to sharpen my skills as I was eager to learn and start making a nice income for Lisi and me.

I did well there and word got out in the building.

At the time, The Herald-Tribune owned the local 24-hour news station (think a smaller NY1 for anyone who is familiar with New York’s local news source station). But a group of investors had taken it over. They operated on the third floor – one above where I worked. During the transition, they poached a leader from the Herald-Tribune, and he needed to build out a salesforce to complement the handful of sellers already on their small team.

Apparently I was on their target list.

I didn’t need a whole lot of persuading. The station had a lot going for it and it seemed exciting to learn a new industry. I joined in April 2009, shortly before Lisi and I had our wedding ceremony.

I got a hang of things pretty quickly.

We were on a draw commission, so it meant I had to produce. I wore a tie everyday to work. I took it seriously. Although there was a rotation of sales leaders, I was always supported. I worked on the biggest accounts. I broke through the 6-figure annual earnings mark for the first time in 2011. I was there for a total of three years.

But sadly, not before I had an idiopathic stroke.

In May, 2011, shortly after turning 32, I woke up on a Saturday morning blind in one eye and with a pounding migraine headache, causing me to vomit violently and often. Lisi and I had gone out the night before and had a couple of drinks, but I thought it was weird to have that kind of hangover after only a couple of drinks.

A night in the hospital after my stroke

Turns out it wasn’t a hangover. There was no known cause for the stroke. Here’s my best guess as to why it happened. I was too focused on serving my clients and not making enough space for my own well-being. Sadly, I didn’t learn the error of my ways until about a decade later.

Fast forward a year, 2012 was a tumultuous time for the station (and the advertising space as a whole). With the advancement of smartphones and the explosion of social media, everything was going digital and I didn’t want to be left behind. I saw the writing on the wall and made a move into SaaS after recruiters for ReachLocal (now LocaliQ) started pushing hard into the local media space for sellers. Many were recruited from the YellowPages, but a handful of us came from local stations.

Although The Herald-Tribune was owned by The New York Times, this was my first time working at a public company.

The company (over) hired on a huge salesforce. Tons of money was being thrown at SaaS companies, particularly those who catered to small, local businesses in an effort to shift them from analog presences to digital ones. For me, it made sense, because I already had a strong network of local businesses I could tap into immediately, while showing them a path to a higher ROI on their marketing spend.

It was a bit of a Wolf of Wall Street style culture. The work hard, play hard type. Tons of cold calling. Hard pressure tactics. The one-call close! If you’ve been in sales long enough, you know exactly what I mean.

I joined the Tampa office, which unfortunately was a nearly hour and a half driving commute for me (without traffic). Luckily, it was a lot of field-based sales, so I was able to convince the Regional Manager that I should work in Sarasota two days a week as that’s where the majority of my network existed.

We had about twelve of us in the office. I was surpassed by sellers who started at the same time as me who used hard-nosed tactics to get deals done fast. It frustrated me, especially since it was a culture nurtured down from the top, but I kept to myself and stayed focused on leveraging my network.

By the end of the first calendar year I was a top 5 producer for a first-year IMC (Internet Marketing Consultant).

Things were solid for about 8-10 months. But office drama, politics, and the commute were starting to take their toll. After about two years, I made a move to go higher (bigger deal opportunities) but do it closer to home (an IT Outsourcing and Consulting firm in Sarasota).

I wore a tailored Zara suit and a skinny tie to my interview, and apparently made an impression.

I later learned that it was more than the sharp dressing that got their attention. The mixture of my New York City experience managing high-caliber accounts and my exuberant nerdiness around explaining the tech powering my small business clients at ReachLocal got the CEO, Tom, excited about taking me under his wings.

Tom had made a name for himself in Hawaii after selling copiers and moving over to help Roy Yamaguchi figure out his IT headaches with his first restaurant. Tom went from helping Roy figure out his BlackBerry to using technology to improve operations.

After helping open the Roy’s in Sarasota, he and his wife decided to move there.

By the time I joined them in 2014, he was running his own company, Datum, with an impressive roster of local and regional brands, mostly in the restaurant and retail space. Tom is a smooth talker. He reminds me a lot of Lance Armstrong – for better and worse.

I knew barely anything about restaurant technology and operations, but I was hired to run the MURS division (Multi-Unit Restaurants). Despite being uncomfortable with not having expertise, let alone experience, I jumped in and treated it more like an apprenticeship.

The year there proved to be extremely valuable.

I accelerated my learning in restaurant tech and operations. I got pretty good at understanding how to package up technology + services and present it as a path to transforming the business. That gave me the confidence to explore options with some of the bigger SaaS players in the restaurant tech space I had been exposed to while at Datum.

That role was literally my bridge from Level I to Level II.

My key learnings from Level I

“It’s not that we don’t have options, it’s that we forget we have them.” – Dan Koe

Selling happens all around us.

In my teenage years, I sold my parents on why I should finish high school early to pursue getting better at soccer. I convinced my Romanian coach that playing in real games was worth the gamble of a big fine. I was selling myself every time I wanted to earn a spot DJing a party or at a lounge in NYC.

That was all before I had an official sales title in 2006.

The point being is you were already in sales before you got your first sales job. Every role I took on in Level I was in a space where I had no specialized knowledge. Unlike law, consulting, or medicine, there is no barrier to entry to success in the business world via sales.

It’s very akin to entrepreneurship.

And right there is the first main lesson: Sellers should start with an entrepreneur’s heart. Chances are you have one, so you need to lead with it if you’re in Level I. Yet, too many are seeking the entrepreneur’s brain. They want the skills, tactics, playbooks, and hacks that get things done fast and pay out the most $$$.

The entrepreneur’s brain will come in time. With experience.

In Level I, use your entrepreneurial spirit to try new things, take risks, be willing to be comfortable being uncomfortable. Saying “yes” more often than “no” is a great ally here (although that will have to shift in future levels as you gain more ownership of your calendar).

The most useful assets during this phase for me were not hard skills (effective cold calling scripts, persuasive emails, specific sales methodologies, or powerful presentations), they were instead the soft ones that served me the most to build a solid foundation (eagerness to learn, staying organized, timing my moves appropriately, and a strong work ethic).

These soft skills opened the door for me to absorb more valuable long-term business skills that would be extremely beneficial in Levels II and III.

By the time I would get comfortable with my cold calling script at ReachLocal, I felt it was time to move on. That cold call script would no longer serve any purpose while at Datum. It would have been out of place. But my eagerness to learn (and obsessing about learning faster), staying organized (and obsessing about getting more done in less time), timing the next leap (and obsessing about the macro trends happening in business), and working hard (but obsessing about impact over hours) were all the major assets I carried in every single role.

Think about your early sales roles. What hard skills do you really carry over from those early days? Are you still using the same outreach sequences from a decade ago? I hope not. But you are likely eager to learn new ways to get creative with the help of Gen AI. You likely have seen the benefits of being organized. You likely understand the importance of cycles and getting “lucky” by putting yourself in the right spot at the right time. And undoubtedly, you understand that to get better at anything, it takes effort, practice, and refinement.

Beware of the certificate life. It may feel good and helpful now, but certifications are really just designed to help the certifier. How is your college degree helping you in your current sales role? Being certified in this or that may get you some level of status, but remember friends, we’re not playing status games, we’re playing infinite ones.

Tap into the attributes you’ve used in every single role. Is it MEDDICC, or something else? Chances are you didn’t wow your last five clients using a certification. It was a combination of things that leveraged your human innovation. Don’t lose sight of those. In fact, double down on them.

That’s your path to graduating from Level I.

Are we done yet?

“Those that have the ability to think for themselves quickly realize that they are being manipulated.” – Dan Koe

I lied to you last week.

I said I would wrap this series up over two parts. As you can see, that’s becoming too challenging and it seems like this is a natural break.

I will deliver two more parts over the coming weeks. Next week I’ll dive deep on Level II’s journey and learnings, where I get even more tactical on what happened to get my earnings to balloon and the key things I did once that happened. Then, I’ll wrap up Level III and the connections between all levels in two weeks from now (where I promise, I’ll share a compelling offer that will be well worth the extra reading).

Hopefully that feels fair, but more so, I hope you’ve gained an insight or two over these past two editions?

By the way, did you like the quotes sprinkled throughout this edition? I’m currently reading The Art of Focus by Dan Koe. I just started, so if you want to join me, I recommend grabbing a copy. We can discuss and share the insights over the final two editions.

That’s a wrap! See you next week.

 

Here’s how I can help you right now (big changes coming- get these while you can):

1 | Unlock the 7 Figure Seller OS

Learn how to use design and systems thinking to become a 7 figure seller. There are 3 options to allow you to customize your learning journey.

2 | Download The 7 Figure Open Letter

Get the creative strategic selling strategy that landed a $5.9M deal with a top 4 major global airline. Bonus inside!

3 | Book a 1:1 coaching session right now

You can book a 60-minute coaching session with me (although the Pro above option provides access to 1:1 coaching with me at a 70% discount).