Looking Back on the First Days of Entrepreneurship


entrepreneur cycle1

The 2009 Summer is drawing to a close already, and in the midst of all those sunny days of beaches, BBQs and baseball, I’ve managed to take my first steps toward building my first business.

So what have I learned so far? Let’s see.

Don’t quit your day job …

In an ideal world, I would have walked into a VC’s office, presented my business plan and walked out with $500k in funding. Not so. I live over here –> in the real world. I value my current job and like the people I work with a great deal. They treat me well, pay me a salary I’m proud to have earned and respect the career I’ve been building and pursuing for the past decade. I’ll continue working there for years to come until the day this new business stretches me too thin.

My Dad asked me the other day about a conflict of interest between my budding business and my long-standing career. My reply, “Today, there is none because I respect the boundaries of each”. From “9 to 5” (typically longer, but let’s pretend) I’m a hard-working, faithful employee. When those duties for the day end, I spend time with my family and then from around 8:00 PM to “post-midnight”, I plow through goals and deliverables to build and market my new enterprise. It’s as exhausting as it is exhilarating, but I’ve been diligent not to spend hours at my day job, working on my personal business … morally and ethically, that just isn’t fair to the company or the people I work with. So finding time at night and on the weekends is the balancing act I, like many entrepreneurs before me, am learning to endure.

And for my next trick …

For some, following a career path is their end game — enough to keep them satisfied with their life’s work, and that’s great. Others, like me, love to complicate their lives — trying to balance not only a career, family life and hobbies, but then they’ll throw “becoming an entrepreneur” on the pile, just to keep things spicy.

Prior to 2009, I was in the former category. I’ve had an extremely rewarding, challenging career. I have a beautiful family: wife, son and dog with  more to come (kids and dogs, not wives). I watch or play sports whenever I have a half minute to spare. And I have one of the most amazing circle of friends and family a person can ask for who gets whatever spare time is left over. Then one day on my way home from work, while reading one of the dozens of entrepreneurial blogs I’m a devotee of, I had an idea for a business. My concept of “work” has not been, and never will be, the same.

I’ve spent the last couple months working and molding my unborn business plan to be a competitor out of the gates. I’m that guy that wakes up with an idea in the middle of the night and emails himself a solution which stands to resolve the payment collection struggles that plague my industry. The trick is to make (read: invent) time for all of the other important parts of your life. Some things have had to take a back seat. My wife and son are my world and I’m lucky that they understand that this is one of my dreams. But we’ll still go to the park on Sunday and sit in the sun, we’ll still go on vacations and we’ll still have breakfast and dinner together on as many days of the week as possible. I may lose out on some sleep for the next couple years, but it will all be worth it. We hope.

If you want something done right …

One of the biggest struggles so far has been learning my limits. I’ve been a perfectionist and pseudo-obsessive compulsive type A’er for as long as I can remember. So if you want something done right, do it yourself, right? Nope. If you want to get it done this year, find a good supporting staff. That said, not every rookie entrepreneur will be able to reach into their pockets and start peeling off hundreds to pay for every last thing on their To-Do lists, nor should they. You need to find the right balance between knowing your business inside and out, but outsourcing the pieces where your time would be better served elsewhere. The master of outsourcing your life to make time for the good stuff is, of course, Timothy Ferris. He articulates this philosophy in his best selling novel, The 4-hour Work Week.

To give you a brief background, my business will be an online eCommerce site targeting do-it-yourselfers and professional contractors. It will beBuilding Your Team

a technologically-intense undertaking, to say the least. And while my background is in IT, coding the entire site would probably not be the best use of my time.

So what roles have I kept to myself?

  1. CEO/COO: All aspects of building the business is my core job. This includes writing the business plan and seeing to it that everything written within those pages is put to action. Sometime later, I’ll also need to hire a staff to fill in the gaps with domain experts.
  2. Controller/CFO: Dollars are constantly flowing into and out of my business (mostly out of for now). It’s my responsibility to not only write the checks, but to make sure all items I intend on selling are priced appropriately so that my business can be profitable.
  3. Marketing Director: I’ve read enough marketing material to write my own book, particularly John Jantsch’s Duct Tape Marketing (book and blog), and will continue to be my company’s “marketing department” for the foreseeable future. A sub-domain to general marketing, is social or internet marketing. This includes following sound SEO practices to get and keep my site on the search engines’ radars; writing blogs; creating and maintaining interaction on Twitter, Facebook, MySpace, LinkedIn, Technorati , Reddit, etc; following click-throughs and sessions via Clicky’s web analytics tools; working with search engines to maximize keyword usage and create online marketing campaigns (read more about Google’s AdSense here), and the list goes on.
  4. Vendor Integration Department: I’m the point of contact when it comes to talking to IT shops, distributors/suppliers, shippers and other vendors who will eventually supply me with not only a website, but the products I intend to offer.
  5. VP of Sales: Eventually I’ll want people to buy what I’m selling. So we already know (#2) that I’m pricing my products, and (#3) I’m marketing my services up and down, left and right. Being our sales staff means being the company’s voice out there talking to leads, figuring out what customer really need; i.e. what makes them click the “Buy Now” button.
  6. CIO/Chief Architect: Do I build my site in the cloud or purchase a cheap web server to get me up and running? Which CMS package makes the most sense. Windows or Linux OS? Asp.net or PHP? These are the kinds of decisions and technical vision I charter.
  7. Project Manager: What does a PM do, anyway? In general, you track anything and everything and help others do their jobs better, inspiring them to push the business forward. Making sure the website is built to spec also falls within the PM’s reign, as well writing the specs from the ground up (typically a Business Analyst, but in my case, I’m both anyway). This is the easy part for me. After all, project management is what I do for a living.

That little list there keeps me busy, to say the least. If it sound like a lot, it is.

So what have I outsourced? In a nutshell: anything related to the actual design and development of my website. This function will be handed to a team I pay out of pocket. I had originally considered partnering with a developer, but things didn’t work out and I’m off to plan B.

As the website and the technology under the covers are the basis for my business’ existence, this “IT piece” is obviously critical. I’ve tentatively partnered with a firm I found over at eLance, a novel tool for any entrepreneur swimming in checklists and deliverables they can’t manage on their own. From writing PR press release to writing code, you can find help at eLance. And the process is simple. You write up a proposal of your job, people/firms bid on the word, you review their portfolios and feedback from past clients, select your vendor of choice, pay them based on certain milestones through the eLance Escrow system, and then submit feedback of your own. No pricey headhunters, nor relying on a handful of shaky references. This is a legit service. I’ll be sure to provide an update as the relationship progresses.

Eventually, I’ll also bring on a professional SEO group as my subject matter expertise will cap out at a novice level. I have a few firms earmarked for now.

Summary …

This experience has been life changing. I’ve already grown, professionally, more during these last few months than the rest of my career. Every day is a new hurdle; whether it’s reading and researching completely foreign topics, figuring out what to do next, staying the course until I have results or just making time for everything. Every task I sign up for is a challenge, but rewarding beyond comprehension.

No matter what the outcome is at my first stab of entrepreneurship, I have a long list of lessons learned and the experience and courage to do it again and again until it’s near-perfect. So this first venture, regardless if in a year from now it’s sailing along or under water, can only prove successful.

Thanks to everyone who have supported and encouraged me to make the leap. I wouldn’t be at this point without you, and you can rest assured that when that first PayPal payment confirmation gets emailed to me, I’m going to print it out, write all of your names on it and frame it. OK, fine, I’m a nerd, but a grateful one, at that.


2 thoughts on “Looking Back on the First Days of Entrepreneurship

    • Sorry for not replying sooner .. your comment got trapped by WordPress’ spam filter.

      Thanks for the well wishes and best of luck to you, too!

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