The one benefit of having a long career that you love is that you can look back in hindsight at the highs & lows, the unexpected twists & turns, the roads not taken & the greener grass, the successes & the missteps, and still appreciate it all for the experiences it gave you, while letting those experiences fuel your ambitions for your next act.

I’ll be the first to admit I didn’t necessarily plan out my career post-college (spent at the flagship University of Massachusetts at Amherst – where I majored in Marketing & minored in Economics). I’d ended up there after realizing my top two choices, Syracuse & Duke, just weren’t financially feasible; it was enough of a stretch to afford out of state tuition, even with scholarships, grants & other financial aid. I didn’t want to be in more college debt than I had to.

Now recognized as one of the Top 25 public business schools, I can definitely say I got the most bang for the buck with my UMass education. Attending a large, recognized business school like that could easily put you on the corporate track, heading to NYC or Boston to work in one of the Fortune 1000 companies that often recruited graduates.

At the time I was there, the sports management, tourism & hospitality schools at UMass were separate from the Isenberg School of Business, but of course you could take electives in those other areas, which I did. Now, those two sub-specialties of management are part of the Isenberg offerings. And UMass’ sports programs have gained more momentum ever since that ill-fated Final Four appearance against Syracuse during my time there.

Knowing what I know now, and realizing the industries I’m most passionate about, if I could do my career all over again, I might have tried to jump directly into sports / entertainment marketing after graduating college or at least an earlier point in my digital career.

But then again, I don’t know that I’d trade the experiences I have had, and the lifelong friends I’ve made in the process, especially since I can bring all of those years of expertise and relationships into digital & experiential marketing for sports, entertainment & lifestyle brands now.

The Beginning of the Digital Marketing Age

Given the timing of when I was a college student, taking the first ever e-commerce class taught at UMass, where we studied the early days of Amazon’s founding book business and Yahoo’s then booming search portal, I didn’t know exactly what was ahead for my marketing career, but I was up for the ride.

Rather than head to a big city such as NYC, Boston or Los Angeles (which in hindsight, is probably where I should have gone following my large campus education in the middle of the Berkshires and farm fields), I retreated back to my small-town life in Maine, where I’d grown up after my parents fled Long Island, NY in the late 80’s.

In any event, like most fresh college grads, by night, I was bartending to pay off my school loans and for my day job, I ended up taking an entry level role as an account manager, working for a small ‘new media’ public relations agency spearheaded by Anne Kennedy, who turned out to be an amazing first mentor and longtime industry friend. With her significant experience in traditional PR, the first wave of websites as a communications vehicle, and my obligatory young professionals’ embrace of new tech, we were inventing what ‘new media’ meant every day.

My on-the-job learning consisted of seeking out social media pre-cursors to Reddit & Facebook, finding old-school bulletin boards and message forums similar to what I’d been exposed to in school, joining ‘listservs’ & early versions of email newsletters which allowed two-way discussions, and submitting client website URLs to the Yahoo! directory & DMOZ, probably on the advice I’d read in one of those forums, from Link Moses himself — the man who acquired the very first inbound links for — and who later became a good industry friend and colleague, the late Eric Ward.

This was the beginning of search engine optimization a.k.a. the “first generation” of SEO’s and the birth of the search marketing industry as later defined by Danny Sullivan, then editor-in-chief of a little website called Search Engine Watch, which he’d founded 3 years earlier (April 17, 1996) while I was a sophomore studying those early dot-com days.

WebmasterWorld, founded in 1998 by Brett Tabke, is another one I likely lurked on for awhile, before officially joining and posting in April 2001 as “skiguide“. I’d taken on that moniker in growing my online presence, when I joined as the Skiing editor or ‘guide’ as they called them back then, writing content about all things skiing from 2000 to 2003.

By then, my hustle was in full force to pay down my accrued college debt. was a great web-based income stream — while I was still slinging cocktails, I was also earning a portion of proceeds from affiliate links and banner ads all over my product reviews, event coverage and summaries of all-expense paid press trips to ski resorts in Vermont, Colorado, Utah, Canada and Europe that came as perks of the job.

One of the core listservs I relied on in those years to not only serve my marketing & PR clients, but to grow my audience of ski enthusiasts — in addition to reading SEW regularly, was the I-Search email newsletter, created by John Audette of MMG, and later moderated by Detlef Johnson.

Regular contributors and question-askers probably included names many search aficionados would potentially recognize — Bruce Clay, Marshall Simmonds, Jill Whalen, Heather Lloyd-Martin, and various website owners / entrepreneurs, including two guys out in Utah, Jim Holland & John Bresee (RIP), who were early to the game, trying to use the Internet to grow their little backwoods, outdoor adventure gear & outfitter shop on the outskirts of Park City.

You might have heard of it. That early start in SEO (& later, PPC) made into the behemoth online retailer it became. Later, in 2004, I moved to Utah — a decision that might have possibly been influenced by Jim & John’s selling of the outdoor lifestyle — which totally fit with my experience growing up in the Maine woods. Plus, the adventure travel bug had hit me by then, bolstered by my first ski trip to SLC after the 2002 Olympics.

Within a few weeks of landing in Park City, I finally had the chance to meet John in person, where he offered me a job from my online reputation and relationship we’d built over the I-Search list.

I probably should have taken that job. In those days, Backcountry was very much a great place to work and the growing sophistication of their marketing technology over the next decade defined online retail in many ways.

They eventually sold out in 2015 for $350 million, cementing Backcountry’s place in #SiliconSlopes history. Over the years, I have had many close friends and industry acquaintances go through the revolving door there, so I’ve heard the good, the bad, and some very ugly stories.

So maybe I dodged a bullet, but maybe I also missed out on a great career opportunity to work alongside some brilliant people and build my brand marketing skillset in the online retail world. But by then, I was already living the work-life balance dream, without the ‘corporate’ BS.

The Search Marketing Conference Circuit Starts

By 2001, due to my participation in various forums and discussion lists, I was becoming more visible, and internally at – where Chris Sherman was also the “Web Search” guide, and Marshall Simmonds had taken an in-house SEO job. We had our own little circle of search talk.

That turned into my first invitation from Chris Sherman and Danny Sullivan to speak at Search Engine Strategies in Dallas, Texas in November 2001, where I’m pretty sure I was on a link building panel with Link Moses. Over the next few years, I also made speaking appearances at several other SES events and Pubcons, raising the profile of our small new media agency and bringing clients in as a result.

Clients at that point we were mostly working with were local and regional (Boston area), but my work in digital content creation, SEO & link building / PR efforts at that point included some interesting CPG & lifestyle brands like Eastland Shoes,, Braun / Oral-B and Gillette, a Maine Lobster shipping service, among others that I can’t recall at the moment.

One of those speaking gigs at SES though, turned into a friendship and working relationship with the webmaster for the lone client that I took along with me when I decided it was time to leave the agency and go out on my own as a web marketing consultant, and that gave me the freedom to leave New England.

Live Where You Want, Remote Work Was a Thing in the Early 2000’s

Of course I’d left Anne and the agency on good terms; it was just something I had to do for personal growth at the time. I wasn’t actively trying to take clients with me, but the single client had only ever worked with me, and we had created a fantastic working relationship by then.

It also made sense, because the client was a luxury ranch and adventure resort in Moab, Utah — at the time owned and operated by a 70’s rockstar who toured as Rick Springfield’s bassist. And that’s the least interesting part of his story as a self made millionaire.

It was also just under 4 hours away from Salt Lake City and Park City, where I’d decided to move to by that point. So I could easily go down to the ranch whenever I needed to, because by then my role had expanded to include more traditional PR, and I’d be hosting FAM trips of my own there for travel agents, journalists and influencers. The ranch also hosted movie crews, corporate retreats and press launches for off-road vehicles, so something was always happening that I could push for digital attention.

(A few years later, I’d get married at that ranch on the Colorado River just before it changed ownership, and both my former boss, Anne Kennedy and Danny Sullivan, whom I was working with full time by then, made the trek from England to be in attendance.)

Utah does have a funny way of calling people here.

And that’s how the next phase of my career happened accidentally. I started living the dream as a skiing and mountain biking “bum”; also hustling as bartender to meet new people in my new town.

I was also under contract working as a community editor at Search Engine Watch, and picking up more search marketing consulting clients – many of whom were in the adventure travel & tourism space. I also continued freelance travel writing. So in 2005, I picked up this domain, Adventures in Search.

It’s had many iterations over the years, and I’ve stopped and started it a number of times, killing off old archives and rebooting as I’ve reinvented my career in search, live events & digital / brand marketing.

And even though being an in-the-trenches SEO is no longer a focus of mine, one thing is true about SEOs — old school habits die hard– and I can’t just let a domain with this kind of age sit around collecting dust.

Categories: Career