20 Lessons from 20 Years: People are Hacking Your Retargeting Offers

My wife did a happy dance in the kitchen one morning that felt slightly out of proportion to the moment. It wasn’t a birthday or even particularly good news. It was an email. I must have looked confused, because she turned her phone toward me and said, “They sent it.” What they had sent was a coupon code, but the important part wasn’t the discount itself. It was the timing. She had been waiting for it and expecting it.

As someone who has spent most of his adult life in advertising and marketing, I like to think I’m hard to surprise. I dropped out of university, but I’ve made a career out of understanding systems, incentives, and where money leaks out when no one is paying attention. Still, every now and then, I’m reminded that there are people on the other side of our funnels who are far more aware than we give them credit for. My wife is one of them.

She explained that she had put a few items into her cart on an ecommerce site she already intended to buy from. Then she purposefully closed the browser, and waited. No checkout. No purchase. Just patiently waited. She knew what would come next. Maybe in hours, or days, or weeks, but it would come. Eventually, an email would arrive reminding her she’d “forgotten something,” often with a gentle nudge in the form of a coupon. Sometimes it was ten percent. Sometimes more. Sometimes there were multiple codes, each slightly more generous than the last.

This wasn’t new behavior on her part. She had learned it from being marketed to, over and over again. Retargeting has become so pervasive that it no longer feels invisible. It feels obvious. A little creepy, maybe, but predictable. People know the playbook now. They know that if they hesitate, if they linger, if they abandon, the system interprets that as friction that needs lubrication. And lubrication usually comes out of margin.

What struck me wasn’t her cleverness, though I’ve now done her move several times after learning it. The depressing part (if you owned the ecommerce company) was that the company had just paid to discount a sale that didn’t need to be discounted. She had already decided to buy. The coupon didn’t create demand. It simply reduced profits.

If you’ve been in this game long enough you see there’s always some new gimmick or buzzword or some new thing that works so well, until everyone starts to do it. Retargeting is already broken. Its already being hacked by shoppers. It already retargets your devices (and your family’s devices). Retargeting gives away your secrets in the form of showing you ads you’ve already seen before, and tells the people you live with what you’ve bought them for their birthday, or that you secretly have been researching divorce lawyers (hopefully not). Or, that one legendary story of Target’s retargeting campaign exposing that a father’s daughter was pregnant before she told them.

Each evolution has brought new tools and new efficiencies, but also new blind spots. Retargeting, especially when paired with email and first-party data, felt like a breakthrough when it first became widespread. Suddenly, we could follow intent. We could chase the almost-buyer. We could “recover” lost sales. But recovery implies something was actually lost.

In my consulting work, one of the things I fight to explain to people is that sales don’t generate revenue. At least not long-term. Revenue dips a little, panic sets in, and the fastest lever within reach is a promotion. It works, at least at first. Numbers go up. The dashboard looks healthier. Everyone exhales. And then the hangover comes. The next month is softer. So another sale is introduced. And another. Before long, the business isn’t really selling at full price anymore. It’s training its customers to wait. That’s what retargeting with discounts is. Its a trap.

You can see this behavior clearly in certain retail brands that are perpetually “on sale.” The discount becomes the real price, and the list price is just theater. The moment they try to pull back, conversions drop off a cliff. The business has conditioned its audience, and now it’s addicted to its own tactic.

Retargeting discounts operate on the same psychological plane, but with a veneer of sophistication. They feel targeted, controlled, data-driven. And to be fair, most consumers don’t exploit them intentionally. The percentage of people who will deliberately abandon carts just to trigger an offer is small. The same amount of people who take advantage of coupons (its around 3%) and the people who will actually keep their receipt and follow-up on that one-year guarantee when something breaks. But those percentages add up, especially at scale, and especially when the behavior is learned and reinforced.

There’s a false confidence generated from these systems inside companies. When a retargeted offer converts, the dashboard tells a comforting story. The campaign worked. The sale was saved. The attribution looks clean. Rarely does anyone stop to ask whether the sale would have happened anyway, or whether the incentive quietly eroded long-term pricing power.

None of this is an argument against retargeting itself. Used carefully, it can remind distracted buyers, reintroduce value, and close genuine gaps in intent. The problem starts when it’s treated as a blunt instrument rather than a scalpel, or worse, as a default setting. When every abandoned cart is assumed to be a lost sale, the system is designed to give something up even when nothing is required.

Not all growth is healthy. Not all conversions are incremental. Sometimes the smartest move is to let a sale walk, to trust that your product and pricing stand on their own, and to accept that short-term volatility is the cost of long-term stability.

I think back to that morning with my wife, as a reminder of how transparent our tactics have become. The audience isn’t passive anymore. They’re observant. They’re learning. In some cases, they’re gaming the very systems designed to influence them.

After twenty years in this industry, I’ve come to believe that the real edge isn’t in ever more clever targeting or increasingly complex funnels. The longer you’re in the game, the more you realize that sustainable business profits come less from hacking behavior and more from understanding it.