Startup founders are passionate about their product. They can recite the feature list, technical specifications, and future roadmap backward and forward. Yet, when it comes to early-stage sales, founders often fall into a trap: mistaking product enthusiasm for selling expertise.
If you are a founder scaling up your first sales efforts, it’s time to rethink the fundamental nature of the transaction. You need to understand what selling is truly “all about”.
If you’re a visual learner, watch this video in conversation with Jordan Belfort, the author of ‘Wolf of Wall Street’ about ‘Sell me a pen’:
The Founder’s Sales Playbook: Three Essential Steps to Selling Value (Not Features)
“It is not the answer that enlightens, but the question”
Tony Robbins
As a startup founder, you are the chief visionary, but when it comes to sales, raw product passion is not enough. The “Sell Me This Pen” challenge, popularized by films like The Wolf of Wall Street, isn’t just a quirky interview trick; it’s a fundamental lesson in what selling is truly all about.
For founders transitioning from building a product to scaling revenue, the goal is not to deliver an enthusiastic presentation of features, but to master a structured sales process focused entirely on the buyer’s context.
If you ask someone who is “not a professional salesman” to sell a pen, they will likely start describing features—it “writes upside down,” or it’s the “best value for its money”. Similarly, early-stage founders often fumble through pitches emphasising attributes like, “This is the best pen ever made…” or “This may be the last pen you ever have to buy…”.
Professional selling, however, demands a deliberate, three-part process centred on the prospect’s needs.
Phase 1: Diagnosis – Identifying and Uncovering the Need
The only rational response when presented with a sales challenge is to start asking questions. The core lesson is clear: until a need is recognized, it simply doesn’t matter how great your product or service is.
- Start with Discovery: Instead of listing features, the founder’s first mandate is to lead a discovery session or needs analysis. This approach establishes you as a consultant helping the customer gain an objective view of their situation.
- Ask Probing Questions: This process of consultative selling involves asking probing questions that reveal pain and uncover underlying buyer motivation. You need to know, for example, “how long you’ve been in the market for a pen”.
- Highlight the Discrepancy: Often, the need is not readily apparent to the prospect, or it may be buried under other wants. If your product is new or highly technical, you must establish the need by highlighting the discrepancy between what the customer currently has (e.g., a “work-around” solution) and what they can potentially achieve with your solution.
A powerful, if cinematic, example of this is when a salesman takes the pen and asks the prospect to write their name on a piece of paper. When the prospect looks for something to write with, the salesman replies: “Oh, you don’t have a pen anymore. Supply and demand, bro”. The need (the inability to write) was created before the solution (the pen) was presented.
Phase 2: Prioritisation – Creating Authentic Urgency
Identifying a need is only the first step. For a sale to move forward, that need must have a higher priority than your prospect’s other needs. A presentation that fails to address an urgent need is usually a waste of time.
Urgency in sales must be authentic. This is not the manufactured pressure of “This is the last one in stock!”. Authentic urgency involves addressing needs that the client may have pushed aside or given a lower priority than they deserve.
As product experts, founders have a responsibility to help clients avoid painful experiences by raising the potential consequences of making a poorly informed decision or simply succumbing to indecision.
Phase 3: Execution – Raising the Stakes
To help a client prioritize and reconnect with the urgency of solving their problem, founders can use a technique called Raising the Stakes.
Think of a movie: a film about a character who isn’t convinced they need to solve their problem immediately goes nowhere. Similarly, a prospect who is not convinced that he has to solve his problem quickly, is a sale that goes nowhere.
Raising the Stakes involves making a series of associations to re-prioritize the decision and bring to light the consequences of indecision or a poor decision. By using this effective technique, you help the client understand the wider implications of continuing with their current painful situation.
In your next sales conversation, focus diligently on these three phases. Catch yourself if you start to get the cart (product) before the horse (need). Your ability to shift from talking about your features to deeply understanding and prioritising your customer’s pain is the true measure of sales leadership.
If you want to dive deeper on this, read my post of the importance of storytelling, especially in crowded markets.
I'm a former general partner at google ventures, head of Google for Entrepreneurs in Europe and founding head of Campus London, Google's first physical hub for startups.
I'm also the founder of Techbikers, a non-profit bringing together the startup ecosystem on cycling challenges in support of Room to Read. Since inception in 2012 we've built 11 schools and 50 libraries in the developing world.
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