Then and Now: 5 Years of Being an Entrepreneur

It’s been nearly 5 years since I left the comforts of a guaranteed paycheck and ventured out to make money on my own.

It’s been a roller-coaster of emotions; ups and downs that make you feel alive and sometimes wish you were dead.

I’ve made a lot of bad decisions, most of which I like to think I’ve learned from, and I’ve gotten lucky a couple of times.

More than anything, I’ve learned that the people you choose to work with, whether it be partners, employees, advisers, vendors, or clients, have such a profound impact on your success – that I decided to write this post.

If you’ve already taken the plunge and gone out on your own, you already know how terrifying it is to scale your client base, make payroll, pay rent (both for your home and work space), and the uneasy feeling when you know it’s time to fire a client.

Nothing really gets easier over time, you just get better at predicting outcomes, and hence not making as many poor decisions.

Where It All Started

It was the summer of 2008 and I was running web operations at a wonderful little non-profit.

The husband of the lady I was working for was someone I looked up to and came to consider one of my first mentors, his name is Will Bast and he had been running his own successful businesses for over a decade.

Over the course of the year or so I was at the NFCA, Will and I became friends and I began to do some SEO consulting for his company. As the volume of consulting work continued to grow, I had some tough decisions to make…

I was 23 years old, had a great job with great people, and my biggest financial risk was some credit card debt (and I’m proud to say, not very much).

After some frank discussions over a series of lunches with Will (and some arduous conversations with my father), I decided I would tap a couple of my friends for input on starting a company.

Through mutual friends I found a PHP developer and a very talented Software Engineer. After weeks of conversations and a 5 day off-site for planning, we decided to start a web marketing agency.

We formed the LLC, got business cards printed, and took office space in Ambler, PA in the same building as Will’s company.

The Evolution of an Agency

One year in we were not the same company we started out as. Our customers had shifted to be far more design-centric and our digital marketing engagements ballooned to require my full attention.

On top of all of this we had grown from 3 to 5 people, and were starting to land more clients in the Philadelphia area, which at the time was roughly 40 minutes away from our office.

We rode out our lease in Ambler and in the spring of 2010 bit the bullet for some shiny new space over-looking City Hall.

We were pretty excited.

Revenues continued to double and triple and we were landing bigger and bigger clients, and started to bring in some top tier talent.

By the beginning of 2011 we had a solid design, development, and marketing team, and were the agency of record for a handful of large companies.

Then something changed.

An Opportunity Arose

I was getting burned out on client work.

The thrill of working on new projects and landing new clients was all well and good, but I had an itch to build something of my own – something that would put my skills to the test and allow me to reap the benefits; I wanted to sell products.

It wasn’t about being selfish, it was about recognizing opportunity and a need for change.

I’m of the mind that if you don’t like doing something anymore, you shouldn’t do it. Call me cold, but this is why I don’t feel bad for people when they whine about not liking their job… get another one.

And really, I just fucking hate excuses.

So I met a guy with an idea.

It was an idea I very much liked and thought would be the perfect opportunity for me to put both my marketing and management skills to a real test, and take the biggest risk I had faced in my professional career.

I was terrified… I had never built something like this before, let alone had a large sum of someone else’s money to do it with.

This was to be my first funded venture, where I was the technical founder and the CEO, and so Factor Media was born.

The Road to Product Development

Project planning commenced in July 2011 and we launched the project January 1st 2012.

By the beginning of Q2 I had to begin scaling a content team and we quickly grew to 32 employees.

We saw massive growth and within 12 months managed to break the 500,000 visitors per month threshold, capturing over 2 million visitors in 2012.

During a board meeting late in the 2nd quarter our monthly burn rate came up in discussion, after all scaling to a team of 30+ people is not cheap, and this wasn’t my money

Taking a close look at how our traffic was growing, I was forced to take a hard look at our production, and make some rough decisions.

It seems that not many people really talk about the dark sides of being an entrepreneur, which seems to be even darker when the project is funded by outside sources.

I had to slow the burn. I had to fire people.

For anyone reading this who has ever had to fire anyone (especially a friend or someone who has become a friend) it sucks. It really, really sucks.

We had designed and built a very popular website that was continuing to grow in the double digits month over month, so why were we scaling back?

Analysis showed that the site’s architecture and content support system didn’t require all of the resources we had. We had, to some extent, built a system that could sustain and thrive on it’s own… where in some backwards vacuum the bigger and better the website did, the less people it required to run it.

Not Skynet… but close.

Even I became a line-item that was no longer necessary.

In June 2012 we re-structured the company and by July I was no longer the CEO, taking a board role and overseeing operations via emails and meetings.

Leaving Something You Started

The real kicker here is neither of my 2 founding projects resulted in an exit, well not yet. So it’s pretty weird to talk about jumping ship when it’s not based on the 2 most common outcomes:

  1. An exit, or
  2. The Ship is Sinking

But that’s what I did.

Leaving my first company was a decision of passion and validation, but leaving my second company was out of entrepreneurial responsibility; the company outgrew it’s need for me.

Ultimately, the latter situation has been going very well – which if you had asked me about in July of last year, I would have been explained differently.

It’s humbling to realize your child has out-grown you.

The Progression Over Time

I’m freaking lucky.

I was presented an opportunity to become a partner at a company doing some big things and working with people that I am continually learning from.

Furthermore, I’ve found that being part of a community is something very important to me, and the joy that comes from working in the company of brilliant people adds more quality to my life than anything I could hope for.

Here’s to the next 5 years!