I’ve always said that marketing is “iterative failure.”

The unique nature of marketing makes strategies and campaigns an ongoing exercise to build business, and not a series of individual races.

Every piece of learning pushes forward to the next phase of learnings. Those lessons include a few wins and lots of misses. Turns out red is no longer in season and green has replaced it; colorful images lose out to retro black & whites for six months then b&w is no longer in favor; polished videos are replaced with homemade, and new targeting emerges. The list goes on and on. Every once in awhile, however, we move from the realm of expected defeats into the domain of the true faux pas.

I would like to say, in looking back at what has been a solid career, that I have had more wins than losses. And that none of those losses were of epic proportions . . . except perhaps for one which was literally 10 feet tall.

I was hired by an international parent team to come into a rural winery to direct the marketing after an extensive rebuild and branding. There had been a LOT of cooks in the kitchen and many of the marketing projects were stalled in multiple committees.

One task that immediately fell to me was to get new creative on a billboard purchase. What seemed like a small and easy project was hampered at every turn by unexpected hurdles. When I approached the graphics vendor to sit down and design the billboard, they brushed me off saying I didn’t have the proper permissions to create the artwork.

I shrugged this off as a recalcitrant vendor and hired a small independent graphic artist and started looking for assets. I came across a file full of opening day party guests for the new tasting room and ascertained (in multiple) that I had the authorization to use those images.

In the pictures of people with half-eaten hors d’oeuvre plates,  poor lighting, and jumbled crowd scenes was an absolute winner: a 30-year-old man sitting at the elegant firepit, leaning forward with a glass of cabernet sauvignon in his hand, a pensive look on his face lit by the flickering flames, and wearing clothes that just stepped from a vineyard. His flannel was folded up to the elbows, and there was a trace of vineyard dust on his boots. The crowd melted into the background behind him.

He was the perfect blend of the unique rural environment and the new, hip tasting room. The style of which destined to soon replace the mom-and-pop outfits that currently dominate the appellation.

He said everything I wanted to say. The image was placed, the text crafted, the hashtags removed by a micromanager, upper executives fast-tracked approvals so we wouldn’t have an empty billboard, and the huge graphics were printed.

I metaphorically brushed the dust off my hands and moved with alacrity onto the next stalled task.

While I was happily slaying other dragons, the small town (population 1,034) first gasped, then held their breath, then fell on the ground rolling in hilarity at what they saw.

And what they saw was the 10-foot-tall image of a well-known local vintner – who owned the neighboring vineyard and winery – being used to advertise a winery that was not his own.

My winemaker was apoplectic, my out-of-town marketing team in disarray, and I was met with sardonic applause at the next meeting of the local community marketing association.

Needless-to-say, the image was replaced lickety-split and I sent a case of wine over to the vintner for “modeling fees.” In the end, it didn’t damage the company’s reputation with the town, and it did break the ice with a group of people who don’t always ken to strangers.

It may seem like the obvious moral of the story is “haste makes waste,” but we turn-and-burn in marketing all the time. What I did learn is that penetrating the wall of a skeptical local team is a top-priority, first-steps requirement. Without having a vested team behind you – very quickly – you could be a newbie with a 10 foot tall mistake.