Equip Yourselves
The Gates Open
Dedicated to my mentor, Chris Dube — Chief of Innovation & Strategy at Prepare 4 VC.
At the heart of every successful startup, pitch, or customer interaction lies a simple but profound formula:
1. Trust: The Foundation of Every Interaction
Trust is the hardest thing to earn and the easiest thing to lose. In the context of startups—especially those led by technical founders—trust is not built through code, technology, or even product capabilities. Trust is human.
A founder who leads with features instead of trust will find that:
Customers hesitate to commit.
Investors hesitate to fund.
Partners hesitate to collaborate.
How does a technical founder build trust?
Listen before you speak. Before you pitch, before you sell, before you showcase your tech—seek to understand your audience. What keeps them up at night? What are they frustrated by? What have they already tried?
Have real conversations. Not product demos. Not decks. Not sales pitches. Conversations. If you can't sit down and engage with customers or investors without your slides or code, you don't fully understand your business.
Tech must take a backseat. Your product is not the hero of the story—your customer is. Tech is just the tool that enables their success. If your entire identity as a founder is wrapped up in what you've built instead of who you're helping, you’ve already lost the trust battle.
The Technical Founder’s Common Mistakes in Trust-Building:
❌ Over-explaining instead of engaging.❌ Talking at people instead of with them.❌ Assuming trust should be given instead of earned.❌ Relying on credentials or technology to "speak for itself."
The correction:✅ Make your audience feel seen, heard, and valued first.✅ Focus on clarity, not complexity.✅ Be real—if you don’t know something, admit it.✅ Show that you're solving their problem, not chasing your vision.
2. Anticipation: The Ability to Hold Attention
Earning trust is the first step, but keeping someone engaged is where most founders stumble. Attention spans today are mechanical bulls—they will throw you off if you’re not prepared.
The moment you capture someone’s interest, the real challenge begins.
A poorly structured conversation, pitch, or user experience can lead to:
A brilliant but disengaged investor walking away.
A confused but polite customer nodding but never converting.
A partnership meeting that “went well” but leads nowhere.
How do you sustain anticipation?
Read the room. Are people leaning in or checking their watches? Are they asking questions or just waiting for you to stop talking? Your ability to adjust based on live feedback is more important than any script.
Speak in escalating value, not technical depth. Every additional piece of information you share should make the listener more interested, not less. If their eyes glaze over, you've gone too deep too fast.
Be dynamic. Flat, predictable, and robotic founders kill momentum. Bring energy, make them curious about what’s next, and let silence do its job—anticipation thrives in the right pauses.
The Technical Founder’s Common Mistakes in Anticipation:
❌ Talking too much, too fast.❌ Failing to ask if the audience is following.❌ Overloading with technical depth before interest is solidified.❌ Assuming the listener cares as much as they do.
The correction:✅ Break information into digestible, engaging chunks.✅ Ask questions instead of dumping data.✅ Let the other person talk (and actually listen).✅ Simplify at every step, making it easier—not harder—to stay engaged.
3. Joy: The Ultimate Result of Your Work
At the end of the day, people don’t buy features, technology, or even innovation.
They buy relief.They buy solutions.They buy ease.
This is the most brutal lesson many technical founders never learn:
🚨 Your excitement for your product is irrelevant.🚨 Your family's praise is irrelevant.🚨 Your accelerator mentor's approval is irrelevant.🚨 Your investor’s polite nods are irrelevant.
The only thing that matters is whether your customer gets real relief, and whether your investors see real ROI.
What does "joy" look like in real-world startup success?
A stressed-out manager who was drowning in logistics now has time to breathe because of your tool.
A frustrated enterprise executive who had three shitty SaaS products now only needs yours.
A founder struggling to get meetings now has VCs calling them back because your software proves traction.
An investor who took a bet on you sees real revenue growth and can tell their partners, “I made the right call.”
Joy is not about your wonderment at what you've built.Joy is their wonderment that their problem is gone.
The Technical Founder’s Common Mistakes in Delivering Joy:
❌ Thinking a great product is enough—it isn’t.❌ Prioritizing internal validation over external reality.❌ Taking feedback personally instead of using it as data.❌ Treating customers or investors poorly out of frustration or arrogance.
The correction:✅ Focus obsessively on making life better for customers.✅ Keep refining until joy happens without explanation.✅ Accept feedback with maturity—you work for them, not the other way around.✅ Remember: People don’t want a product. They want a better life.
1.) A Failure to Present Is Most Often a Failure to Understand
At its core, communication is a test of self-awareness. If we struggle to articulate our ideas effectively, it is not simply a “messaging” problem—it is a deeper failure of comprehension. This failure is best examined through the lens of self-efficacy, the belief in one’s ability to navigate challenges and achieve goals. When founders stumble in their presentations, it often reflects three fundamental breakdowns in self-efficacy:
1.1. Forgetting Core Strengths
Many founders spend so much time refining their product that they lose sight of the deeper reason why they are building it. A startup’s core strength is not its technology—it is its impact.
A founder who truly understands their company’s strengths will:
Anchor their pitch in value, not features ("We help businesses cut cloud costs by 40%" instead of "We use a proprietary Kubernetes optimization framework").
Distill what makes them special without the temptation to over-explain.
Speak with confidence and conviction, rather than leaning on dense technical jargon to sound impressive.
When a founder struggles to present their idea in clear, compelling terms, it’s often because they haven’t deeply internalized their own strengths.
1.2. Ignoring Key Deficiencies
Conversely, founders also fail to improve their biggest weaknesses—especially their blind spots in communication. Technical minds, in particular, can fall into the trap of overvaluing logic while undervaluing persuasion.
They assume “If my product is great, people will just ‘get it’.”
They underestimate the importance of storytelling and simplicity in selling an idea.
They default to an “educate-first” approach, drowning investors/customers in details instead of making them feel something.
1.3. Lacking Empathy for the Listener
Perhaps the most dangerous failure is a lack of perspective on the audience. When founders present, they are essentially asking for attention and trust. Yet, many fail to walk a mile in their audience’s shoes:
Investors are not product engineers. They are looking for a market opportunity and a path to scale.
Customers do not care about AI/ML algorithms. They care about outcomes.
Partners do not need to understand every line of code. They need to see strategic alignment.
A presentation is a moment of forced attention—you have taken people hostage for a brief window of time. If they struggle to understand or care, that is a failure of the presenter, not the listener.
2.) A Complex Idea Is Not Therefore a Good Idea
There is a common misconception in startup culture that complexity equals intelligence, and intelligence equals value. This is a dangerous fallacy. A startup does not earn respect by being difficult to understand—it earns respect by making a complicated world easier for its users, customers, and investors.
2.1. Complexity Without Utility Is Noise
Just because something is difficult to build does not mean it is worth building. Many technical founders get trapped in the "because we can" fallacy—pursuing ideas that are intellectually stimulating but commercially irrelevant.
A founder spends years developing a hyper-efficient, decentralized database architecture—but fails to prove why anyone needs it.
A team builds a blockchain solution for supply chain tracking—when a simple spreadsheet would have sufficed.
A startup claims to "revolutionize" an industry but delivers a convoluted product that frustrates customers instead of helping them.
Good ideas are not complex for complexity’s sake. Good ideas remove friction, solve real problems, and create clarity where confusion previously existed.
2.2. Being Busy Is Not the Same as Making Progress
Technical founders often fall into the activity trap—equating effort with forward momentum. They mistake:
Feature-building for customer validation (“We’re adding 10 new features this sprint!” instead of “Customers love X feature; we’re doubling down on it.”)
Working harder for working smarter (“We pulled an all-nighter fixing infrastructure” instead of “Did we need this infrastructure in the first place?”)
Raising money for building a business (“We raised $5M” instead of “We proved our unit economics”).
Great startups do not thrive on complexity—they thrive on clarity.
Stripe simplified payments.
Dropbox simplified file storage.
Uber simplified transportation.
Every world-changing company turned something complex into something intuitive.
3.) The Parity Between Capability and Empathy
3.1. The Technical Founder’s Dilemma
Technical founders are often too focused on what they can build rather than what people actually need. The ability to write great code, design algorithms, and architect systems is invaluable—but without empathy for the customer, it is not enough.
Many founders think that just because they have built something powerful, customers will naturally see its value. This is rarely true. The act of simplifying and explaining things well is an act of empathy.
If you can describe your product in ten words instead of fifty, you respect the listener’s time.
If you show a simple use case before diving into features, you respect how people learn.
If you craft a pitch that investors can repeat to others, you respect their need for clarity.
3.2. Customers Sense When You’re Building for the Wrong Reasons
There are two types of startups:
Those built to solve real problems.
Those built to chase status and money.
Customers can tell the difference. A product built with genuine care feels different from one that was cobbled together for a quick cash grab. Companies that scale sustainably have founders who:
Deeply understand their users and their pain points.
Are obsessed with solving problems—not just making money.
Listen, iterate, and communicate effectively.
3.3. Investors May Be Impressed at First, But Revenue Will Expose You
For many startups, early fundraising is easier than long-term survival. Investors are often willing to take bets on potential—but MOM (Month-over-Month growth) and ARR (Annual Recurring Revenue) will reveal the truth.
If a startup was built without true product-market fit, no amount of initial funding will save it. Investors may nod along during your AI/ML pitch, but when traction stalls and churn rates rise, the market delivers its verdict.
Final Takeaways: Building for Understanding, Not Just Complexity
If you struggle to explain your product, you probably don’t understand it well enough.
Being complex does not make your idea good—simplifying complexity for others does.
Technical founders must work hard to translate capability into empathy. The simplest explanation is often the most powerful.
Customers can sense when you are truly solving a problem versus chasing money.
Investors might be impressed by complexity, but retention, revenue, and user adoption will ultimately determine success.
The best founders balance intelligence with clarity, expertise with humility, and technical brilliance with human connection.
View the full Watercooler series by Steve Vilkas and pledge your support here: https://thewatercooler.substack.com/p/the-three-step-formula-trust-anticipation
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