“I used a hashtag for a campaign that belonged to an activist group.”
We came up with a hashtag for a campaign highlighting how our software could empower entrepreneurs. Our social feeds were suddenly flooded with posts we couldn’t control, and it became impossible to separate our brand from the movement.
“I set up a twitter bot that thanked trolls for insulting our company.”
What we didn’t anticipate was how easily the automation could be exploited. Within hours, trolls caught on and started tagging us with sarcastic or offensive posts: “This company is a scam and a joke!” The bot, unaware of context, chirped back, “Thanks for your support!”
“I wrote a white paper that tanked an entire quarter.”
We were mid-sized, trying to break into the enterprise space, and leadership was obsessed with becoming known as "thought leaders." Naturally, I got stuck leading the charge with a whitepaper that was supposed to be our crown jewel. The topic? AI-driven insights for enterprise growth. Very buzzword-heavy, but at the time, that’s what everyone wanted to hear—or so we thought.
“I hyped up a limited-edition product that wasn’t actually limited.”
We were launching a new “limited edition” lipstick collection designed to create buzz and FOMO. The messaging was clear: “Only available while supplies last!” Our team poured weeks into influencer campaigns, glossy ads, and social media countdowns…
“I launched a billboard campaign with a QR code that didn’t work.”
What we didn’t anticipate was how easily the automation could be exploited. Within hours, trolls caught on and started tagging us with sarcastic or offensive posts: “This company is a scam and a joke!” The bot, unaware of context, chirped back, “Thanks for your support!”
“I hosted a the worst webinar in the history of webinars”
I’m still haunted by the worst webinar I ever organized. It was early in my career, and I was tasked with putting together an “industry-leading” virtual event to showcase our flagship product. The topic was promising…