On being laid off & unplanned entrepreneurship

〰️ it’s weird to look back; I sometimes get confused on how I got here 〰️

Whiteside Mountain in Highlands NC
Whiteside Mountain in Highlands NC

Most folks dream of being entrepreneur; “a path that seemed inevitable“, they say. None of that shit applies to me. I’m only here cause I kept getting laid off and that nonsense infuriated me.

I treated my first layoff as a joke, as I’d seen them in movies & TV; “now they’re happening to me – how funny“. My second felt like a whispered “fuck-you”, as the company had been acquired and I was deemed useless. The third and fourth scrambled my brain and forced me down a path I never intended to travel.

I’m only here cause I had to save myself.

I remember thinking:

I can’t trust them anymore; I gotta figure out a way to generate revenue myself; from my own business; that I control. Online preferably.

That’s where I started. Daunting for someone with a History degree. I had no other choice.

So, I took stock of my background at that moment. Web analytics, Paid Search, and pittance of SEO.

Ok, I’ll start there. I’ll skip coding for now.

I’d recently been exposed to a new online ad network, that paid by lead and/or click. I had previously implemented it on a company’s website & it generated around $30-$50 a day for them.

Sounds good to me, let’s try something like that.

Since I couldn’t code, I couldn’t launch a website. So the gears of my dusty cobweb cranium began to turn. What can I do that doesn’t require coding? Eventually, a thought bubbled up:

Well, what’s stopping me from signing up for one of those ad networks, and then going to a search engine, typing a popular search term, digging through the organic results, searching for sites WITHOUT advertising, emailing them to request ad rates, and implementing //my own// ad pixel there.

There wasn’t a damn thing stopping me. So I started doing that (with the hopes the website owner never found out about said ad network, as I could be cut out of loop). This was late 2003.

I needed a topic. Alot of people seemed to search for tourism information online, so I leaned into that corner. Began searching broad terms & phrases in any search engine. My thought was, if site is in top ten results for major keyword, then it’s safe to say they’re receiving a significant (enough) amount of traffic.

CaribbeanI’d search ‘Aruba’, and would email every site that fit the bill. “Do you accept advertising? If so, what are your rates?” I’d search ‘Bahamas’ & repeat process. Then ‘Key West’. And on and on.

I’d get a nibble occasionally. I’d reply asking their traffic levels & monthly ad rates. Then I’d napkin math whether I’d be able to cover *their* ad expense & (possibly) generate profit with my own ad revenue from the network (which was guesstimated, on my part). Oftentimes, the numbers wouldn’t work.

Until the owner of a Cancun travel website replied. His rate was $50/month to advertise. His site ranked well for several Cancun related terms & received significant traffic. I estimated my ad unit, if placed in a certain section on the page, would receive 2% CTR. Then I multiplied that number by his daily traffic levels, and guesstimated $5-$8 of revenue per day. I remember thinking I was going to get hosed on the deal, but me being me, I kept going.

He asked what type of ads I’d run. I didn’t know, as they were dynamically generated based on the content of the site/page. I told him “several travel & tourism promotions targeted to Cancun“. ¯\_(ツ)_/¯

That worked for him, so I began paying $50 a month, and shot him my ad pixel to implement. Off-the-bat, the darn thing began generating $300-$350 a month.

The ads were perfectly targeted. Cancun hotels. Swim with dolphins. Paragliding. Cruises. Most months I was clearing $300/month profit (after ad expenses to the website owner). I couldn’t fukkin believe it. It was my mini-watershed moment; exposing me to the fact that, yes, dolt-brain me could do this. If I could generate revenue from this disgustingly duct-taped business model, I could do it in other fashions online. I just didn’t know what those fashions were yet. One thing I did know:

I gotta learn how to code

This was the avenue hanging me up & intimidating me. I was currently advertising on other folks websites. That they built. They hosted. They managed. I had to mimic that same position. And that meant coding, launching, & managing my own sites.

Outside of its complexities, coding tripped me up cause it required a basic tenet that I typically veered away from: basic reading.

Alfred E NeumannI don’t mind reading, I just don’t like doing it, I find it difficult to focus (I’m more of a distinguished MAD Magazine type of reader). I’d rather watch a video tutorial, listen to an audiobook, or have someone side-by-side explaining things. Those avenues didn’t quite exist back then; so I had to get creative.

Instead of lamenting & bemoaning my position, I decided to throw out all the rules and just start building a website although I didn’t know how. I’d figure out the rest once I started.

Someone told me ‘hosting’ was required, so I bought a cheap package and began to poke around. Once I skipped the documentation, I discovered they had a ‘ticket’ system where they allowed customers to submit support questions. Huhmm.

~ ~ ~ ~ ~
Ticket #1:
from: Peter
message: please help me get a website online
(╯˘ -˘ )╯
~ ~ ~ ~ ~

… and – God bless them – they replied. That’s where I learned about the “index.html” file. They became my unpaid tutors. Volleying countless questions on how all this stuff works. What the hell a domain name was. How to update my DNS. File transfer protocol. They pushed me far enough where I became comfortable researching myself. Googling questions. Forum questions. Twitter. Asking friends. All of it. Hell, my friend Charles Lumpkin educated me on the wonders of a < div > tag.

From there, I got a basic one-page website online. Hand-coded. I felt like trashcan-Superman.

Then I channeled my advertising/marketing background. “What’s a website I can build that might generate ad revenue & serve small businesses?”

Yellow PagesMy father’s friend worked in the Yellow Pages industry, and always remarked how profitable that business model was. We were still in early internet days (2004’ish), so I mused how I could mimic that industry online. In other words, create a central directory bringing buyers & sellers together. Buyers searching for services; businesses providing those services. I liked this simple model, so I swung that way.

I grabbed a Yellow Pages book in my apartment, opened it up, and began to flip through. In those days, basic listing were free, but businesses could advertise large rectangle ads in their category. As I fanned through the pages, I’d keep an eye out for sections with heavy ad promotion (as it indicated an industry that understood the value of advertising). I found a few. Windshield repair. Limos. Carpet cleaning. Self storage. Pest control. And on and on. Then, I’d buy an ugly domain & create an online directory of that category (ie. pest control), mixed in with geography based terms for seo, like ‘atlanta pest control’. And on that page, I’d curate several atlanta pest control operators, and list all their contact info. About as basic & boring of a site as you can get. But simple to navigate, and no hoops to jump through.

View sourceThen, as I further began to code, I discovered the wonders of “view page source”. I could right-click, copy & paste another website’s syntax into my editor; monkey with that updated design; then upload it to my server. Tables & rows, mainly. I’d swap out the logo; change the background color; the width of the container; manually add new pages. My trashcan-Superman aura was morphing into trashcan-Zeus. It felt like walking through a deep fog treasure-chest where I could only touch & feel what was directly in front of me, and each outcome was bizarrely fascinating. An ape could have designed better, yes, but I was proud.

Then traffic began trickling in. From outreach; from sponsorships I placed; from seo stuff; from all kinds of marketing endeavors.  I began offering premium listings; businesses began signing up; I’d charge them through Paypal (no Stripe back then). Then I began adding those ad networks (I mentioned above). And more revenue began to appear. A somewhat consistent monthly recurring revenue stream.

I was still working 9-5, but an escape hatch was coming into focus. A path to avoid someone else’s bonehead business decision which kneecaps a company & executes my career. The glitter of fancy salaries had already grown dim – that hook they’d dangle to entrap me. I yearned for my own {mini} golden goose that provided the independence I was blindly searching for. The Rage Against The Machine lyric often came to mind:  “Fuck the G-ride, I want the machines that are makin’ ’em”. [src]

WordpressMy development path accelerated when I discovered WordPress. Most hosts had one-click installation. WP had recently added the ability to create ‘Pages’, so I moved my development focus inside that petri dish. The pre-built themes (free & paid) were a boon to my design inadequacies.

I built more sites ~ nights & weekends ~ thanks to WordPress. But that became time consuming, so I began *buying* fully developed websites, direct from mom & pop operators via cold email. Usually informational sites. Then I could expand the content based on search volume trends and incorporate small bits of advertising.

Appalachian Trail
AppalachianTrail.com circa 2008’ish (now sold)
AppalachianTrail.com was a good example. I cold emailed the owner a $3,000 offer for the site & domain. I received no reply, which was normal. Until I did receive a reply; 30 days later; accepting the offer. I further built the site out & it began generating around $500/month for me.

What I kept noticing, though, when I’d transfer a site under my wing, I’d {immediately} focus on domain transfer, as control of that asset dictated ownership of the site.

These domain ‘things’ seemed intriguing, so I dug deeper. I discovered the expiring domain name market. A universe where 50k-100k domains expire & auction every day. There, I discovered the impact of a blue chip, descriptive .com domain name ~ especially in development. An unfair advantage that allows small players to punch up.

I remember sitting in a pizza joint with my friend Allen Graber, grabbing lunch one day. At some point, he stepped away from the table and my mind was wandering. Dissecting my path to that point, and trying to stitch together what it all meant, and if there was a next step. And a thought surfaced: Why not just wait. Sit and wait. And watch the expiry lists. For a premium .com domain to expire, that has development potential. I was in no rush. That seemed to jive with my inner-nature. I’d already witnessed a few gorilla .com’s go up, so I understood others could as well. I’d just need to empty my mind and wait for the pull to arrive.

boots and ropeThe pull came in 2009. The domain was marvelous. A group in NY state abandoned ‘DudeRanch.com’, and I acquired at auction for $17,949. It provided the backbone for me to build a vacation marketplace for that historic industry. An environment where I could shepherd vacationers towards dude ranches that met their needs. And monetize the asset through premium (highlighted) listings that paid me a flat-fee per year.

The mild success I achieved there allowed me to quit the 9-5. It opened me to more projects. More domains. And opened me to empty myself into these endeavors.

I didn’t raise any money for these projects. I funded them with my 9-5 salary. Solo. And the reason for that was simple – why on earth would I vehemently abandon boneheaded micro-managing layoff kings in the 9-5 world only to raise money & adopt a board of boneheaded micro-managing layoff kings in the startup world. If I’m gonna build, I’m gonna have free-rein decision making to pursue any and all ludicrous business models, with no oversight. If I fail, fine. That’s on me. If it works, son-of-a-gun, my job will feel like play.

I still to this day, over 20 years later, experience the sting from those layoffs. The check-mate move that I couldn’t counter. I had no plan, but I started. I had no goal; I just got going. I guess I’m still going; I don’t quite know where. But I’m quite content. And thankful. It appears peace of mind is the prize I’m pursuing.

it’s weird to look back.

[ Some images from first projects of mine circa 2004-2008’ish; plus early & current views of DudeRanch.com. ]

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