Making the Missed Window of Entrepreneurialism Not Matter (in New York)

by Mike Levin SEO & Datamaster, 08/16/2010

As I approach forty and fatherhood, I find myself contemplating how to keep my professional edge as my world changes around me. It occurs to me that my anchor in life has always been writing, in some form or another, be it hand-written journals, or some electronic format. And I made the determination to always be writing, whenever my attention doesn’t need to be on the real world. That writing keeps me focused and on-task.

This works out quite well in the information age for a knowledge worker. A rarely discussed fact is that it doesn’t matter precisely how you get your work done, so long as you do. If you were hired by a modern company, there is a good chance that no one knows more about your job than you do. The vision that the top-dog knows how to do the job of everyone beneath him or her is, and only needs employees for lack-of-time is dead wrong. You hire people because they know MORE than you do in their area of expertise, and they only need your company, in a sense, to outsource paperwork and payroll. As Drucker would say, they only need you because they can be more productive in your company than on their own.

Of course, fear–or shall I call it, risk aversion, is the other goblin keeping all truly skilled knowledge workers from striking out on their own as an entrepreneur, or at least a contractor. A steady paycheck and healthcare benefits are nice for folks establishing families. If you’re going to jump off a cliff and learn to fly, it’s best not to do it with your family in tow. So the risky entrepreneurial thing is a young man or woman’s game, and you get a new crop of these types from the Bay Area, New York or Boston culture. They’re tuned in and turned on, and the amount you can accomplish at a young age with the Internet, a good idea, and a tiny bit of funding is staggering and intoxicating.

But once you miss that window, your brain is rewired, and your opportunities dry up–right? Wrong! I’m a suburban Philly kid born in 1970, introduced to the mundane Brady Bunch suburban existence. Somehow, I missed the entrepreneurial winner-bug. I suspect it was in part from lack of exposure, and I never really “got” what it was like to be insanely more advanced than those around you, until I got my hands on the Amiga computer in my senior year in high school. By a phenomenal coincidence, Commodore, the company that acquired the Amiga, was in my back yard, and I managed to hook up with them.

I then proceeded to watch it disintegrate from an insider’s perspective–a secret fanboy living my dream, having been beamed up by the mothership, then having my heart broken as I witnessed it all fall apart. I saw how dropping a super-potent chunk of excellence into a vat of undiluted suburbia could dissolve away every last trace of what you loved. You would have thought this was my coming of age, and loss of innocence. But no! I was to stay innocent, but angry and strangely effective through the years–until I finally, with the help of New York, resolved the schism in my self-image this created.

I jumped the Commodore ship along with the rest of the rats during my senior year in college, as I had to take over a family check cashing business when my father died. In the course of running that business, I had to deal with an estranged sister moving back in on me, a mother’s decent into bona fide insanity, and finally an attempted robbery by way of hammer to the back of my head. I dealt with this the way I dealt with everything else in my life–appropriate force. So, I shot the guy.

Uh, yeah, so as you might imagine that my path through life has not followed exactly the entrepreneur-in-training path as others, even from my own very neighborhood that has produced dot-com millionaires. After suburbia dissolved away all that was exciting about Commodore, and I sold the check cashing company, I tried getting myself back on track by hitching my wagon to one of the few Commodore spin-off stars. The Commodore ship-jumpers longing for the Bay Area flocked to Trip Hawkin’s Amiga-like 3DO. The ones left over in Bumblefuck, PA–such as myself–flocked to a certain not-to-be-named software company, where I proceeded to have my heart broken YET again–but this time, by suburban mediocrats who still somehow still believed they were hot shit by association with Commodore.

I did great things, including creating a very Ruby-on-Rails-type joyful agile framework based on VBScript in 1999. With it, I subsequently created blogging software at about the same time as Pyra (now Blogger). I created a search-engine-friendly content management system based on generalized XSLT data transformations before Google’s ascension to fame. I created a manufacturing bill of materials system, a shipping system, an online order management system, and integrated all of them so you could effectively track a customer from their first search-hit. Oh yeah, did I mention I also created a Google Analytics-like tracking gif system.

Against this backdrop, I was actually earning a base salary plus commission–a cut of the gross profits, internationally. This is what motivated to basically rebuild the company’s business systems on my agile framework, for the purpose of “debugging” the company. It sounded like a sweet deal, and actually kept me from my flight to the West Coast and Silicon Valley during those days. Yet somehow, it never payed off. In addition to the income not being there, I was somehow picking up the vibe that I was thought of as a stupid “marketdroid” by my fellow Commodorians who also took verbal jabs at the customer-base through the public support forum of the very startup I worked for. Maybe it was the commission, but it hit me like a rock. This was damn insulting–not just to the customers–but also to me! My brain was re-wired!

Suddenly, it dawned on me. Maybe these Commodore ex-patriots were not merely as good as they made themselves out to be. Maybe all the excellence that I loved in the Amiga was really a result of it’s true inventors: RJ Mical, Jay Miner, Dale Luck and all the others who refused the suburban existence, and were themselves actually screwed by Commodore to the point of embedding the message: “We made the Amiga, they fucked it up” into the very operating system. Maybe I was working with the “they” that the inventors referred to in one of the most notorious Easter Eggs of all time, and that Commodore did not really fail due to poor marketing like the claim that my circle adhered to like a self-image-protecting dogma. Maybe it was this un-derserved ivory tower mentality and customer contempt that killed the Amiga, and the very same fate was destined for for my current gig, and it took the clarity of vision that only comes with commission to let me see.

I decided to investigate.

Interestingly, I had a direct view-port to whether customer sales inquiries were being followed up on at the time, because that aforementioned Ruby-on-Rails-like framework I mentioned was also the basis for a lead generation and customer relationship management system, based on a private continuous discussions that tracked from inquiry to recurring orders. Imagine being able to see the first search hit of interest, then the form being filled out, then an in-bin of inquiries, then subsequent discussions held in a private message-board like system (reminiscent of Facebook’s inbox), and all the communication that goes into solution selling difficult products with long sales cycles, and then seeing the order getting placed, and then all technical support follow-up issues, and then recurring orders being placed, and then their transition into a case study or success story to help with further content production that creates new search hits, and repeats the cycle.

Imagine this all in the year 2000–long before the Facebook/Salesforce connection started to dawn on people–long before anyone recognized Google as the king-maker of our age–long before content management meant anything other than multi-million dollar Documentum and Vignette systems. Within my hand, I had an entire next generation business framework that gave me direct insight to the sales pipeline, and unique understanding of where the bottlenecks were occurring. So, I looked.

Lo-and-behold, almost no prospective customers were receiving a return phone-call, email or post. The nature of the system made it easy to verify. Prospects themselves were posting back into my system questions about where the follow-up was. Solid-looking leads to all appearances were being wholesale ignored with a contempt that could only be equated to what was actually going on with verbal condescension in the public support forum. It was a deadly one-two punch of no follow-up to new customers, and chasing away old ones. It was outright embarrassing, and now thanks to my system, it was transparent and accountable within the company.

It didn’t help that at about this time, the same person responsible for the public condescension of customers in public also tried to disable my system through high tech trickery. By this time, my system was running like a reliable juggernaut of lead-generation, accountability, and condescension censorship–and the board of directors was starting to take notice and asking questions about why sales leads were not being followed-up. Unfortunately, my system was starting to slow down under the load. it was on an incredibly incapable Pentium-III generation computer, and I needed more raw power. I had to fend off uninformed and audits of my work claiming that I was programming inefficiently, and scream bloody murder to get a simple pair of new servers, which proceeded to be taken away from me on arrival. The plan of the mediocrats was to run VMWare Workstation as a virtual host (mind you, not ESX or Server–but WORKSTATION), and put SQL Server and IIS on VMWare sessions, which already proven to be incredibly unreliable under similar circumstances, and give me only a log-in to these sessions.

For anyone familiar with the issues, back in 2004, this amounted to a death-sentence for my reputation for juggernaught-like reliability and unstoppability. With each power-outage, you not only had to wait for the VMWare host to restart, but you manually had to terminal serve into the host, and manually restart each VMWare session. If this happened in the middle of the night, everything stayed down until being discovered in the morning. Yes, automation scripts and monitoring software could mitigate it a bit, but not without race conditions and down-time. It was a pitiful excuse for the company-turning force I was previously applying with just a Pentium-III class computer, and finally promised to exposed the chink in my armor that all the mediocrats were clamoring around looking for.

All the while, I was navigating these treacherous waters with writing. I wrote in my Webmaster Journal–another system written with that aforementioned agile framework. I wrote and I wrote and I wrote. To this day, it’s lurking their in their business systems. I thought out-loud. On my hour-long reverse commute from Philadelphia, out to the boondocks, I listened in my car to Peter Drucker and Sun Tzu on audio cassette to get strategy. I listened to Moby Dick to ensure I wasn’t casting myself into the role of Captain Ahab. I listened to every Sherlock Holmes on audio cassette that my local public liberary offered, to hone my powers of observation and deduction. And I did a bang-up job, effectively steamrolling the mediocrats, and with the help of the board of directors that finally stepped in to take charge, turned the company around to profitability.

I would have probably done quite well for myself financially had I stayed there, enjoying a low cost of living and a percentage of gross revenues as that industry continues to blossom. But I would have gone insane, as the tides of suburbia continued to wash up against my shore, gradually eroding away my character, and giving me the false impression that the whole world is that way, and that it always has to be that difficult. It’s like I trained on Mount Olympus in thin air, and then came down to where the air is richer, and everything suddenly becomes easier.

Peter Drucker’s opinion that a skilled modern knowledge worker only hooks up with a company because he or she can be MORE productive has echoed in my ears through the years. There’s no bemoaning it now, but it certainly would have been wise to go the entrepreneurial route while I was in Philadelphia, my living expenses were low, I had no family to worry about, had piles of ahead-of-its-time technology in my pocket, and could have self-funded. I saw the Google Guys and Mark Zuckerberg ascend. I saw dozens of other smaller players make it and flip–all the while, working for the man, spinning my wheels, never really building anything for myself long-term, and always trying to convince employers to take a risk that I personally wasn’t willing to.

Shame on me, and shame on me for doing it so long that now I have a family on the way, and have even more incentive to go the cautious route. But unlike the thankless, suburban employers of the past, I’m now working for an digital marketing firm in New York City that knows its very health is tied to the sort of inventing in which I specialize and have such a successful track record. Even though it didn’t make me rich, it certainly has left a trail of successes. At the Philly Commodore spin-off, they’re still using my system to this day. From my first job in New York, there’s a Web 2.0 site that continues to make profits while the parent company that incubated it is no longer around.

I basically leave a trail of successful endeavors that aren’t mine, and an even longer trail of writing that never got read by anyone other than myself. And that’s a shame–especially these days where precisely that sort of writing has value in public. With the rare exception, I say to hell with secrecy. Like Seth Godin says, you could write out your business plan and mail it to your compeitor, and it wouldn’t make a bit of difference, because it’s all in the details of day-to-day implementation and your passion and persistence that makes the difference. Its almost never words on a page.

And so it is with that spirit, that I make this blog post as sort of a public commitment to re-engage with online, similar as to I did with HitTail on my first Web 2.0 venture in 2006 when it was just starting to get interesting. But this re-engagement will belong to me, on properties I own and benefit from. It is time to start enjoying the benefits of compound returns over the years. I may be starting a little bit late at forty, and the time-crunch may be on like it never has before, with a little one on the way, but I write anyway.

I started writing in 1988, a year after my discovery of the Amiga computer, and I continue to write today. It’s amazing to me that so much writing has amounted to so little. And so, I shall write publicly now when I can, so at least it can perhaps be read by someone and amount to something, if even a few moments of entertainment. And my subject-matter will be dealing with missing the young man’s entrepreneurial window, and why even that doesn’t have to matter much, when you’re in New York City and you really still “got it”. It’s never too late, and you don’t always have to jump off a cliff to get yourself flying.