Common Misunderstandings Founders Have About Customers

Hot Take Friday 🌶 Had a conversation this week that brought back a familiar pattern - especially with the most technically gifted founders: They build powerful technology… and then struggle to sell it. Not because they lack ambition. But because they confuse broad capability with market leverage.They build elegant, extensible platforms designed to do many things. And then hesitate to narrow in on one use case, fearing it would “underutilize” their technology. But here's the paradox: In the early days, the broader your platform, the harder it is to move. 🪨 Customers don’t want to buy technology. They want to buy a solution to their very specific, very annoying problem. Preferably one that doesn’t involve them thinking too hard. If your go-to-market strategy requires the customer to (a) understand their own workflow, (b) imagine a better version of it, and (c) map your ambiguous platform to that imagined workflow… well, that’s a lot of cognitive load for someone just trying to hit their Q2 OKRs. You have to sell outcomes, not infra. What founders often miss is that focus isn’t a constraint - it’s a forcing function. It sharpens the product, tightens the feedback loop, and accelerates distribution. The companies that break out - the ones that become verbs, categories, defaults - they all start the same way: with a sharp point of entry. Slack? Team chat. Zoom? Video conferencing. Wiz? Cloud security. Figma? Design tool. Even if they’ve grown far beyond that, the origin story sticks. And so does the brand. One clear use case, one buyer, one line of messaging. The uncomfortable truth is: Technical teams often want the product to speak for itself. But markets are noisy and buyers are busy. Clarity is the unlock. So if your pitch still starts with “we’re a horizontal AI platform”… It might be time to ask: 👉 What’s the one painful, valuable, obvious problem we solve better than anyone else? Start there. Repeatability precedes scalability. The path to becoming a category-defining platform is to solve one narrow problem, at scale, for a long time.

Just re-watched Wolf of Wall Street and it’s crazy how so many people still don’t get this scene. We’ve all heard of the “sell me this pen” challenge—a classic test of sales skills that pushes candidates to identify needs, highlight value, and close a deal, even with something as simple as a pen. This was gospel to me when I was in consulting. But here’s the thing: the exercise isn’t about the pen. It’s about the mindset. And too often, people miss the mark entirely. It’s pretty obvious: Don’t force someone to buy what you’re selling if they hadn’t even THOUGHT of buying it. Last week, one of our recruiters sat in an interview for a brand management role. The candidate was asked to sell a product. Their opening line? “Do you want to buy some chocolate milk?” Before the recruiter could even respond, the candidate launched into a prepared spiel about why their chocolate milk was the best. No questions.  No curiosity.  No attempt to understand the “customer.” It was immediately clear they weren’t the right fit. Why? Because they didn’t bother to ask:     🔹 What do they usually reach for when they’re thirsty?     🔹 Does the customer even drink milk? Are they lactose intolerant?     🔹 Do they like chocolate? Instead, they assumed. They pushed so hard and the “customer” lost all interest. When you don’t take the time to understand the person in front of you, you’re not selling—you’re talking AT them. And no one buys into that. The same principle applies when pitching your product or business as an entrepreneur. Too often, founders fall into the trap of focusing on what they love about their idea, rather than what people actually need. They pitch features instead of solutions, assumptions instead of insights. Great entrepreneurs don’t just sell—they listen. They ask questions. They uncover the real problems their customers face. And they position their product as the answer. Because at the end of the day, no one wants to be sold a pen they don’t need—or to sit through a pitch that doesn’t actually solve the real problem. #startups #entrepreneurship #leadership #founders #careertips #pitching (Video Credits: The Wolf of Wall Street | Paramount Pictures)

In 2001, Tim Ferriss launched a supplement brand. But sales struggled due to one error. The supplements boosted mental performance. So, he thought his target customers were students and overworked executives. Until Tim Ferriss discovered that NCAA athletes were buying BrainQUICKEN to improve their sports performance—not for studying. By pivoting to focus on athletic performance, Ferriss found his real audience, changed the name to BodyQUICK, grew the business, and eventually sold it to a private equity firm. This is a common trap. Even successful brands often miss what their customers value because they work with assumptions instead of realities. These assumptions lead to wasted ad spend, stalled growth, and messages that don't stick. I’ve seen it firsthand. Once, I was working on a project for a company doing about $100M at the time. They were trying out a lot of different things but struggled to grow revenue. I ran a survey with a high level of statistical confidence. But they didn’t believe the results. “There’s no way our customers think that way.” I reran the survey. It cost another $25,000. Guess what? Same results. They had fallen into a common trap: believing their customers were the customers they wanted. It happens all the time when companies create Ideal Customer Profiles (ICPs). Companies fall in love with some idea of their customer. And they end up ignoring the customers who are spending money with them. As with the $100M client, an ICP can get you far. It gives you some direction. And any consistent direction will often be better than no direction. It’s like running with a pair of frayed shoes: Frayed shoes are better than nothing. But you’ll make out what you can achieve in them. Growth eventually stalls when you don’t have a complete picture of your real customer. And it resumes when you do. Aligning what you think about the customers with who the customers really are is critical for continued growth. Here are 7 tips to help you stay focused on your customers so you can win market share: 1. Ask open-ended questions 2. Analyze behavior, not just words 3. Understand their why, not yours 4. Segment according to the problem\ 5. Talk to passionate fans 6. Test, test, test 7. Plan scenarios Using these strategies will ensure that you focus on your real customers instead of who you imagine them to be. And, of course, drive growth. Watch the video below for a deeper dive into each of these tips. 👇

One thing so many founders misunderstand: leading a company isn't about being right all the time. It's about knowing when you're wrong. This kind of brutal honesty about what’s working and what’s not is hard, but it's the only way forward. When I started Traceable by Harness, we got almost all of our assumptions wrong — and this was my third company. The What: We assumed companies wanted API protection. Turns out, they first needed API discovery. The Who: We targeted mid-size companies. But enterprise customers felt the real pain — and urgency. The How: We started with a PLG model. Turns out, classic enterprise sales was the right path. We pivoted hard. And often. Eventually, we were able to make Traceable a success and years later, many assumptions proved true — but there’s no prize for being “eventually right.” My advice to founders: don’t be afraid to pivot and don't cling onto assumptions you can't validate.