How on earth I became an entrepreneur - Peter Askew w/ Peter Askew X’ed out : )
The email landed in my inbox around 10:05/am, alerting us of an all-hands meeting in 15 minutes. “Guess we got acquired”, we all thought. 16 minutes later, we were all laid off. This was February of 2001.

I was first alerted of my uselessness in 1995, when ~ fresh out of college ~ I worked as an intern at the Mayor’s Office of Film, Theatre & Broadcasting in New York City. I fell in love with the opportunity, and began cutting hours at my salary-generating retail occupation just to spend more time there (I was sleeping on a futon at my roommates apt, so I could justify the revenue shortfall). The MOFTB recognized my spunk, and attempted to create a paid position for me. City Hall caught wind of this new role, though; they stepped in, and filled the slot with their own person. I didn’t quite understand what occurred; but do remember several co-workers hurling expletives in frustration. I also remember bewilderment staking claim to my outlook on life. “Wait a sec”, I remember thinking… “they created the position for me, but I’m not even qualified for it.” I wound up interning there 2 more months cause I still enjoyed it.

What Color is your ParachuteI kept wandering though. I wound up back in my hometown of Atlanta, as my spidey-sense indicated I might need couches to reside on as I continued to litmus test my life path. I was randomly introduced to the book “What Color is Your Parachute”, and was mildly intrigued by the the ‘Advertising Career’ section, so I decided to shuffle in that direction. My first job (an ad agency representing Dreamworks), laid me off after 9 months due to company acquisition. I was already familiar with the feeling.

I then became enamored with the web, and was able to convince a local Atlanta startup to hire me as an ‘Advertising Traffic Coordinator’. I didn’t quite realize how immensely fulfilling the role would become. Part of my day was self-education (coding, graphic design, database, UI, UX, etc). The other part was designing & managing our revenue generating ad platform. eTour.comI remember, several times, coming home dizzy with info they’d crammed into my feeble brain. It was a euphoric experience. Those puzzle pieces began to fall into place, though. When they settled, I noticed an opportunity for revenue growth. We implemented it, and were able to generate an additional $1M in gross profit. I was promoted to Product Manager, and trained my replacement. Then 2001 rolled around. Ad revenue dried up. The ‘executive team’ had originally hired 300 folks in hopes of company acquisition – but that didn’t happen, & now they couldn’t support salaries. Then that email I mentioned at the outset landed in my inbox.

It was a gut punch face slap. My replacement, who’d only been there a few months, avoided the hatchet (cheaper salary, I presume). I would have stayed and worked for free if they would have asked. They didn’t.

I laughed it off initially, as that recurring theme had become comical. But the months of unemployment that followed (eleven in total) had me question everything, including my self-worth, my identity, and purpose.


Rat fink CEOs had shown their cards, and I refused to drink their hooch any longer. I was fed up being the brunt of poor business decision making, of being a cog in a wheel, of being impacted by no fault of my own. As I swept up the pieces of my mangled psyche, I didn’t quite realize my identity had begun to slowly morph into an entrepreneur, without my permission. Self-preservation was my primary goal. I’d figure out the rest from there.

So I sold my house to stay afloat – unloading a $130,000 mortgage that I was fortunate to break even on; my brother lived nearby, so I moved into his 2nd bedroom.

The first 6 months of job searching were fruitless; the web had imploded – most folks felt it was a fad. I didn’t agree, so I kept looking.

I found a way to attend my own 30th birthday during this time. At Benihana. Happy Birthday to me, I’m “going places”.

Months 6-9 resulted in a few nibbles, and meetings. While interviewing for a Project Manager role, the hiring individual began to mock my college degree in Southern History. I didn’t know how to respond, so I just sat there and took it.

Looking back, I could have simply immersed myself in coding education; but my brain didn’t work that way yet. It was in temporary survival mode. I was drowning and my instincts instructed me to tread water.

At ten months in, I received 2 nibbles: one from a new’ish search engine called ‘Google’; and the other from an established offline business moving online (AutoTrader). They were both searching for Advertising Analyst roles.

At eleven months, oddly, they both offered me a role on the same day; when it rains, it pours I suppose. I declined Google – I needed some level of stability I thought. I accepted AutoTrader, and rebooted my online career. “Simply Outrageous Support” Award I won
And I began to excel. But, instead of companies laying me off, I ~ strangely ~ began to lay them off.

I’d stay on-board, use the privilege of employment and study every aspect of their operation. Paid, ‘free education’ sorta. And when new opportunities popped up elsewhere, I’d jump ship without a thought. My lizard brain would subtly whisper “got you first”; but I realized that was petty. These were the rules they created; I just began playing along.

At one job, a public records company, I implemented a new service named ‘AdSense‘. It began generating an additional $50-$100/day of revenue for the company. “Huh“, my contracted brain mused, “what’s stopping me from building my own site & adding this ?…“. I then suggested a Google Adwords test, a recommendation which received heavy pushback. “We tried it before, Peter, it doesn’t work.” But I kept pushing. After a test implementation, and proof of revenue, I fully setup our accounts & generated in excess of $1M+ of additional profit. Contracted brain jumped in again, “You can simply build your own site & generate this cash, you realize?” At my yearly review, I requested a raise on my $35k/yr salary. They told me to slow down; that those things were complicated. So I quit (and accidentally left behind a coveted Google bean bag chair the search engine gifted me due to our enormous ad budget).

But the experiences began making sense; I oddly felt a direction forming from the fog of wandering.

I wound up consulting for a multinational shipping & receiving company in their corporate headquarters on a 6 month stint. I pitched in on all avenues of marketing, branding & lead generation. Billboards in Shenzhen (Guangdong), China. NASCAR driver sponsorships. $500k month-long paid search budgets. When my consulting contract expired, they extended a $100k+ offer of full-time employment. Without pause – I rejected it. I vividly remember 5 or 6 work friends assembling in my cubicle, scratching their heads in stunned, inquisitive disbelief. I didn’t even have anything lined up after that. The company had served its purpose, and I’d saved cash, so I was ready to move on.

By that time, I’d been able to assemble a rough skill-stack, comprised of web development, ad operations, graphic design, sales, analytics, seo & ppc, domain names, email management; essentially web basics 101. It didn’t seem overwhelming; it felt like I’d uncovered a cheat code.

So the urge to build arose. On nights & weekends, I’d churn out small web projects, hand coded in HTML. The first was a crude directory of bed & breakfast establishments across the globe. The topic didn’t make any sense, but it didn’t matter. I simply wanted to establish a rhythm of building.

I began to understand the importance a great .com domain had on development. So to limit my scope and narrow my field, I began digging around the adventure travel niche. Why that? Well, it didn’t seem like work to me; and that seemed to jive with my inner-nature. So I kept going. I’d search for destination & tourism related landmarks, and attempt to identify underutilized web properties. The site popped up, & seemed underdeveloped to me, so I sent the owner a $3,000 offer to purchase it. A month later he accepted. I was still learning HTML in those days, so I simply expanded the site from 4 pages to 20 pages. Folks would then email me questions about the Trail, so I’d find answers. I experienced a vague hue of usefulness, and became hooked. It began generating $500/mo for me (via AdSense). That made me happy. So I kept going. booth conference booth at Tanque Verde Ranch in Arizona
I began digging deeper into the domain expiration world. The nuances of Pending Delete & Pre-Release. Of exclusive inventory, and private sellers. 2 years later, the domain ‘’ expired (pending delete), and I acquired it for $17,949. I created a marketplace/directory of dude ranch vacations. I partnered with a friendly competitor ( We’d embark on thousand-mile road trips to visit ranches, and share that knowledge with travel-seekers. We made ad deals through hand shakes. We’d forward partners valuable leads. The revenue generated from that project allowed me to quit the 9-5 world permanently.

These small, painstakingly patient steps are what lead me here, to this essay. It felt so unusual at the time, but feels so natural now. That path then lead me to onions. To ranch employment. To domain investing. To independence.

Sure, I felt useless at the outset; that was their opinion, though. I ultimately found a way to be useful, because that’s what I decided.

I didn’t want to be an entrepreneur – I was content being a 9-5 employee. The employment Gods had other plans. When I reflect, I can’t imagine going back. I’m so fortunate all this garbage happened.

So I think it’s safe to say, to every motherfucker that laid me off, thank you.

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