Evolution

Looking back to look forward, I think it’s helpful to do recaps of life. To some degree, it helps me better understand my own life story, while leaving behind breadcrumbs about my life that somebody may pick up someday.

I’d like to rewind over a decade back to the day where I graduated from college after taking a nearly 4 year ‘break’ to pursue a few entrepreneurial interests. I can’t quite remember my exact age, but I believe I was around 23 years-old when I graduated from OSU.

Before graduating, I already had first-hand experience in business, legal matters, finance and operations of small to medium-sized businesses. I also had an Ohio Real Estate license and had spent nearly a year working in commercial real estate before the market crashed in 2008 – costing me over $165,000 in lost (and anticipated) commissions during the month of December. As a result, I accrued over $20,000 of credit card debt and had to make a lot of really hard decisions about how I’d make my next move(s).

With the little money I had left, I invested into an online venture with my then-business partner. That inital project turned out to be a dud. However, the founders of the failed company came up with another plan; a pivot, if you will. “Entertainment shopping” was a hot new buzzword in the online community, taking up the European market by storm. Their idea? Built an entertainment shopping here in the states – one of the first of its kind.

It worked.

In a matter of months, the business was making steady revenue and had a growing customer base. Our success was published in newspapers across the state of Ohio, and I felt like we were onto something really big. We were.

A few businessmen read one of the articles and decided to reach out to me; curious to hear what a young tech entrepreneur had to say about their own hopes to enter the entertainment shopping space. Three hours later, they offered me a partnership, 5,500 square feet of Class-A office space, and a blank checkbook to build the business with the money they put together.

Within weeks, I turned the office space into a buzzing company; recruiting over 35 unpaid interns who were looking for Summer experience. There was no promise of pay, but we did manage to give them free lunch every day.

Accounting. Finance. Design. Development. Sales. We had all the makings of a real business – except for one important thing:

Revenue.

As we grew closer to launch day, I remember hiring a personal assistant who had a desk outside of my large corner office. When I say ‘large’ – I mean palatial; it must have been at least 20x45ft, with a conference table, furniture, mahogany desk and hip-to-ceiling windows covering every inch of the walls. One of her responsibilities was ensuring there was always hot coffee in my mug – while also keeping our interns on task.

When I wasn’t working in the office, you could find me at the hottest restaurants and bars in the area; all paid for by the ‘suits’ using their AmEx Black cards. I went to steakhouses more times than I could count, with tabs that could cover most of our interns monthly expenses. It was quite a season.

When the site actually launched, there wasn’t the anticipated wave of sign-ups that the suits (and myself) expected. As a result, I watched the business bleed itself down to a painful death – and my own bank account in the process.

I had hoped to hedge my bet on this new shopping venture with the ownership stake I had in the prior venture – which continued to grow in monthly revenue. However, there was one fatal flaw that I made with the prior company; the partners didn’t keep a close eye on the books/bank account.

As it turned out, the founder of that company had been using the business as his own personal bank account; buying cars, clothes and expensive purses for his wife.

In a flash, it was all gone.

20-something year-old me wasn’t quite sure what to do. So, I stuck my head out looking for opportunities. In less than a month, I found one; a Founder in New York City was on the hunt for a project manager to help him grow his business; an accredited online MBA program with video instruction, taught by Ivy-League teachers.

The kicker? It was only $5,995.

With a promised salary of $4,000 per month (which was high for me at the time) I packed my bags and went to New York City, living for a short time in a 1-bedroom apartment on the Upper West Side of the city, right across from the American Museum of Natural History on West 77th Avenue.

For several months, I worked tirelessly to make that business a success. Like my prior venture, it started to get some traction; students were enrolling, curriculum was being developed and we were starting to get some high-profile enrollees from well-known companies in the .com sector.

During that time, I broke bread with Brad Hargreaves and Matthew Brimer – founders of General Assmbly, as well as Daybreaker. They were both sharing an apartment and doing eveyrthing they could to make it to the next level – which they both did successfully.

As time went by, the founder became more and more distressed; citing we weren’t enrolling enough students. Knowing we had secured a solid round of funding from an investor, I began to wonder what the problem was.

Weren’t we doing things right? From my calculations, we had nearly two years of operating capital in the bank.

On a Tuesday, I got a call that I no longer had a job.

What happened? The founder embezzled the intial round of investment, and when the investor was pressed to make their second half of the promised funds, they asked to see a balance sheet of where the money had gone.

Nearly $127,000 had gone into the founders pocket, expensive dinners, travel and repayment of prior debts. He had been banking on fast enrollment of studnets to cover this fact, and got caught with his pants down.

The NYC dream had turned into a nighmare and I found myself scrambling for a new plan.

By Friday, I was back in Ohio; living in my Mom’s attic and wondering what I’d do next.

I went to her church that Sunday and was stopped by one of the attendees there, who asked me what I was up to ‘these days’ – to which I replied:

“Web design.”

It was partially true, as I had tried my hand at building a few websites during my time in New York.

“Come into my office on Monday. I’ve got two clients for you.” he told me. He was the owner of a successful design/marketing agency.

For months, I worked alongside his team in the office. At that time, they were still building websites from scratch, while my process involved using WordPress – something a bit unconventional during its infancy in the web world. Why? Because it was largely used for blogs, rather than end-to-end websites.

The owner took notice of my process and ability to create sites a lot faster than his in-house developer. He invited me out to a client presentation where I helped him sign a large contract with a nationwide retirement home community – a contract that would have paid me over $30,000 as the lead designer/developer.

Suddenly, I stopped getting invited into the office to work. He stopped sending me questions/updates regarding the project, and I began to smell a rat.

He gave the project to his in-house developer, who I spent months training on how to level-up his work and save countless hours in development. The owner pocketed the $30,000 I was hoping for, and the in-house developer made $18 an hour for his efforts.

Was I bitter? Absolutely. However, I never let the setbacks get my down for very long. Rather, I used them to propel me further down a path that would eventually turn itself into Tripleskinny – my now successful web design/development agency, which has fed me for over a decade.

Why do I share these stories? Because they’re reflective of a season of opportunity that I now see is losing traction – and fast. When I first started my entrepreneural career, there was a sea of opportunity for people that were willing to do the work others didn’t want to do, while also being willing to invest the time (and sleepless nights) leveling up their skills to accomplish these tasks.

My first six-figure year was the result of helping a large dental chain enter the world of Facebook/Google Ads. At that time, they didn’t know how to do so – and neither did I – but I was willing to invest the hours into learning a new skillset and delivering them a ridiculous amount of value for the money they paid me to do so.

Those same sorts of opportunities aren’t as accessible for fresh college graduates, because the ‘knowledge gap’ is now butting up dangerlously close to the ‘AI can do it’ mindset that I see companies now adopting at scale.

As I write this, I’m keenly aware that some of my own clients have begun to use AI for the same deliverables they used to pay me to execute for them, and it’s a bit unsettling to think about the next iteration of my own career and skill sets that have earned me a comfortable living for a considerable amount of time. However, I know that things will pan out in my favor – because I continue to push the cutting-edge of technology and deliver results for clients that deliver enormous amounts of value.

This evening, I rewrote two website plugins using Claude AI; a task that would have taken standard developers several weeks to build, test and deploy. In one instance, I was able to implement a high-level API integration between two payment platforms in less than 90 seconds, with thousands of lines of code being written in the time it took me to make a cup of coffee.

In many ways, I see that the world is changing far faster than many people will be able to keep up with the new technologies.

In a lot of ways, it’s akin to farmers that tireleslly worked their land, with only a few of them realizing their fields sat over oil – a little bit of digging and these farmers went from breaking their backs in the field, to driving Rolls Royces on mudding courses for fun.

With the world changing at a lightning pace now, I can’t help but ask one question:

Will young college graduates have the same types of opportunities that I had? The answer is a hard one, because many of them won’t.

“Entry level” positions are going to be a job type that has already begun to disappear. Why? Because ‘entry level’ work is now something that can be done by an algorithm. And on the flip side, ‘high level’ work is also becoming something that trained people can do with an algorithm.

In the last 24 hours, I performed the equivalent of 8-12 weeks worth of high-level custom web development work – without knowing a single line of code. When I say 8-12 weeks, it’s not a stretch of the imagination, either.

Not every industry is capable of taking advantage of these innovations. For example, a hairstylist can only give one haircut at a time, and a housekeeper can only clean one house at a time. It’s impossible for these types of occupations to ‘level up’ in this new era where work output is no longer measured in hours, but in the 10’s, 100’s and 1000’s of X’s that the same work was done only a year or two prior.

“My engineers now work at 1,000X the output they did five years ago.” a CEO was recently quoted as saying.

In the last 24 hours, I was able to deploy over 10,000 lines of custom coding, all without knowing how to write a single line of it by hand.

Were an engineer to do it by hand, this would have taken nearly 700 hours. Let that sink in.

We are now in a very different day and age than the year where I graduated. The line in the sand betwen hungry graduates and opportunity isn’t getting smaller – rather, it’s growing further apart in exponential measures with every passing day.