Talking to the wrong people: Why your marketing isn’t working

Oren Meshoulam is a Canadian-born, Israeli entrepreneur and marketing expert. He started his first business at 16, running Dungeons & Dragons extracurricular programs. After military service, Oren built a career in call centres and management before transitioning to marketing. 

He led a major venture for AWACS, an Israeli car radar company, in the US. Frustrated with the lack of tailored support from marketing agencies, he taught himself digital marketing and founded his own agency focused on practical, business-first strategies for small firms.

Oren is now the co-founder of Tailor Made Marketing (TMM), a boutique agency that focuses on creating personalized strategies for small and medium businesses. TMM helps clients cut through the noise with services like PPC campaigns, social media management, website development, automation, data analytics, Amazon strategy, and training workshops. 

Their mission is to simplify digital marketing and offer transparent, hands-on solutions that actually move the needle. TMM avoids one-size-fits-all approaches and instead focuses on building strategies that are tailored to each client’s context.

This article is part of the Business Insights Series, where I speak with entrepreneurs and decision-makers to understand what’s working, what’s not, and where things are headed in the business world. In this conversation, we get into the reality of customer communication, how agencies fail (and why), and what actually makes a marketing strategy work for a business.

Let’s dive into why so many marketing efforts miss the mark, and what we can do about it.

Many companies hire agencies hoping for a ready-made recipe for growth. They’re presented with impressive dashboards, slick reports, and standardised packages,but often without any genuine engagement with what actually makes their business unique.

This experience shaped Oren’s belief that scaling a marketing agency should not come at the cost of understanding the client. When strategy is templated, it may produce short-term results, but it overlooks long-term fit. The nuance, the edge, the context that makes a business stand out,those can’t be templated.

Rather than risk exposing client details, Oren now uses this past frustration as a reminder to keep digging deeper. Every project starts with curiosity. Not with assumptions. That’s the difference between just running campaigns and actually building market relevance.

Know who you’re really selling to

Understanding your customer means staying engaged with their reality,consistently, deliberately, and without assumptions. In practice, it’s also the part most overlooked. Businesses often default to what they want to say, not what their audience needs to hear. The result? Campaigns that are technically sound but contextually off.

Oren made it clear during our conversation: most marketing efforts fail at the very beginning. They misidentify the audience, or worse, assume that their own perspective mirrors that of the buyer. That false equivalence leads to a cascade of mismatches,between offer and need, between tone and expectation, between product and context.

“The first thing we do, we actually analyse the end user before we even go into the accounts… once we had the profile, we went into the accounts, Google Analytics, Google Ads… and we see that the type of content, creatives, targeting, had nothing to do with the end user.”

When there’s no certainty around who you’re trying to reach, decisions around messaging, platforms, creative, and targeting become guesswork. Businesses end up optimising noise, not relevance. TMM Agency integrates a precise understanding of the target audience right from the beginning and forms the foundation for every strategic decision. Instead of relying on abstract personas built in isolation, the focus is on watching behaviour, asking real questions, and testing assumptions through actual user interactions.

“Usually us as business owners, we are not our own buyers. And it’s very hard to put a different hat and say, all right, then what is my actual buyer looking for?”

This disconnect is common, especially in founder-led businesses. The founder is often deeply invested in the product, emotionally and intellectually, and that passion can blur the perception of what the customer actually values. In this context, empathy plays a strategic role in decision-making and communication.

Knowing your customer means you can frame decisions in their language. It’s how you move from broadcasting features to offering actual solutions. It’s also how trust begins with a pattern of relevance that the customer begins to recognise over time, rather than a one-time pitch.

Thinking like your customer is hard work. It requires intellectual humility, structured observation, and a willingness to change course when the data doesn’t confirm your intuition. But that’s what sets apart campaigns that feel right from those that just fill space.

What today’s customers actually want

As PwC reports, speed and convenience are the most important elements of a good experience for over 80% of consumers. In practice that means customers will quickly abandon any process with too many steps or delays. PwC even found that a single bad experience can drive away about a third of customers.

Oren summed it up neatly: simplicity, speed, and satisfaction. These are the three qualities that define modern loyalty.

“The client comes down to only one thing… they want simple, fast, and seamless.”

He followed the catchphrase with clear, grounded examples. A banking app that freezes or requires too many steps leads people to switch providers, regardless of how reputable the institution might be. 

Fuel stations lose customers when the process of paying for gas takes longer than expected, even if prices or product quality remain competitive. It’s everyday friction that turns routine actions into frustrations. And people will avoid friction every time they can.

“I left two gas stations because it wasn’t convenient. By locking my car, going in, waiting in line… it’s time consuming. So no speed, no convenience, and obviously no personalisation.”

The key here involves more than improving a single point of contact; it requires designing the experience across the entire customer journey. Where can time be saved? Where can confusion be removed? Where can a moment of frustration be turned into a moment of relief? These questions reach beyond UX,they shape core business decisions and directly influence customer loyalty.

When you look at loyalty through this lens, it stops being a vague emotional concept and starts becoming a set of decisions businesses can actually influence. That’s important, especially for small and medium businesses who assume loyalty must be “earned” through branding alone. In truth, most customers stay when the cost of leaving feels higher than the benefit of switching. That cost is often time, energy, or convenience.

This framework,simple, fast, seamless,offers a diagnostic tool. If loyalty is slipping, don’t jump to revamp your logo or launch a new discount. Instead, ask: where are we making things harder than they need to be? Where are we asking too much of our customer’s attention, time, or patience?

Good businesses respect their customers’ time. The better ones obsess over it.

Listening is hard. Adapting is harder.

Even when businesses receive feedback, many fail to act on it. They cling to an imagined market instead of engaging with the one that’s already present and showing signs of loyalty. That reluctance to adapt may come from fear, legacy assumptions, or the lure of a more ‘aspirational’ audience. But chasing an idealised customer while neglecting those who already believe in you is a costly misstep.

“We get that this is my client base, but I want these guys as well. And we’re constantly saying, until we don’t get the ones that actually are accepting you, they’re going to be your biggest advocates.”

This dynamic shows up everywhere,from startup founders targeting early adopters while ignoring existing users, to large brands that prioritise new acquisition at the expense of existing satisfaction. The customers who are already saying yes, already coming back, already sharing your work, those are the people who create sustainable growth.

Listening to them means studying behaviour, patterns, tone of voice in support tickets, or the churn that reveals where you’ve slipped. It means having the humility to say, “What I thought they wanted might not be what they actually need.”

“We do not know how to listen to our end client… we want to share our knowledge… and we’re not capable of just being quiet for a moment to hear what the client or the prospect actually needs.”

Many businesses,and agencies in particular,are built around outbound motion: show, explain, pitch, promote. But there’s a skill in staying still. In letting the customer speak without interruption. In resisting the urge to justify before fully understanding.

Businesses that develop this listening culture gain two unfair advantages: relevance and timing. They spot shifts early, they adapt their offers without losing momentum, and they speak in the customer’s language before the competition catches up.

This takes time to develop,and when done consistently, it becomes a competitive edge that compounds. Patience, self-awareness, and adaptability are cultural. And in business, culture has a longer shelf life than any campaign.

Partners, not clients

At TMM Agency, the client relationship is intentionally reframed as a partnership. This phrase reflects a real, structural principle in how they operate. It shapes how they build strategies, conduct meetings, allocate resources, and measure success. Oren’s philosophy is that mutual accountability drives better outcomes, and that approach has become the cultural backbone of the agency.

“This is also why we call them our partners. Because we actually see them as partners and not our clients… We have one common goal. It’s not me against them. If they win, I win.”

It’s easy to say you want a “partnership” with clients. Many agencies put that word in their decks. But few structure the relationship so that both sides are aligned on incentives and outcomes. 

At TMM, that mindset translates into a higher tolerance for friction,the kind that emerges through critical thinking, honest feedback, and shared accountability. If something isn’t working, it’s addressed. If the client’s assumptions are flawed, they’re challenged. And if there’s a tough decision to make, it’s made together.

What stood out in our conversation was how this approach builds trust over time. When you stop acting like a vendor and start operating as a co-pilot, you build traction that lasts through slow months, bad campaigns, or pivots in strategy. Clients feel it. And they stay.

There’s also a layer of self-discipline that this model requires. You can’t commit to true partnership if you’re guarding your process, avoiding transparency, or hiding behind jargon. You have to open the books, explain your decisions, and work in a way that invites collaboration rather than compliance. That’s a higher bar,but it builds stronger businesses.

Agency relationships are notorious for being fragile. But when both parties share risk, communicate openly, and pursue goals together, fragility gives way to resilience. That’s what TMM is designing for: a structure where growth is built on shared wins, not just deliverables.

Conclusion: Who are you actually talking to?

Marketing only works when it connects. And connection comes from relevance.

But what does relevance really mean? Effective marketing depends on more than keywords, channels, or trendy visuals. It requires context,understanding where your customer is mentally, emotionally, and practically, and offering something that fits that specific moment. Missing that moment often costs trust, which is much harder to win back.

When businesses take time to listen,to truly understand their customers,they start to see where the real demand lies. They pay attention to what’s being said,and what’s left unsaid. Silence, hesitation, workarounds, these are signals too. Real marketing begins when we stop assuming and start observing.

“Our job as marketers is how can we help you create a demand for your product, regardless of where they are in the funnel.”

Oren’s words frame it well: the marketer’s job is to generate demand. That means understanding not only who the customer is, but where they are in their decision-making. It’s a longer game. It requires more listening than pitching. More diagnosing than describing.

If your marketing isn’t landing, maybe the issue isn’t your product or price. Maybe you’re trying to meet someone at a destination they’ve never been to. Maybe you’re answering questions they haven’t asked yet.

Good marketing resonates. And that resonance starts with insight.