3 Lessons While Preparing for a Pitch Contest
Entrepreneur Office Hours - Issue #325
This week I had the chance to coach ten student founders preparing for a startup pitch competition. Call me crazy but I love the nervous energy of a pitch competition — ideas bouncing around, founders rehearsing under their breath, wondering how their story “lands”, trying to get the story out of their heads and into the hearts of others.
Out of the ten, nine signed up. (Good luck to the one who didn’t — I truly hope they nail it!) But for the nine who were brave enough to walk through the open door, something interesting happened. As we worked through their very different pitches one by one, three themes started to surface.
The first was authenticity. Not the empty buzzword kind. The “tell the story only you can tell” kind. Why this? Why now? And most importantly for an early-stage founder, why you? Judges aren’t only evaluating your idea — they’re evaluating whether you are the person closest to the pain point, the person who has earned the right to solve this problem through your lived experience, the person with the obsession to keep this going long after the shiny pitch competition is over.
Again and again I see founders bury their own stories. A healthcare founder didn’t mention the years spent navigating the very problem they solve. A product designer left out the true aha! moments from their customer discovery that gave them conviction to move forward with this idea. When those details finally surface, the story starts to click. The pitch shifts from a list of features (truly, who cares? no one....) to a personal mission. We see you care. So we mirror that and start to care as well. Our brains light up. Authenticity becomes the foundation of the trust you’re building with the audience.
The second theme was empathy. Not sympathy (although I have sat through plenty of pitches in my life that deserved a handwritten apology after). Empathy means getting out of your head, and putting yourself in the judges’ seats for five minutes. They will be listening to pitch after pitch, brains overloaded. Your job is to make it easy for their heads to start nodding, for their eyes to light up. That means avoiding jargon, insider language, acronyms, and anything that creates distance.
One founder had a slide with abbreviations only a specialist would understand. They aren’t being unclear — they’re suffering from the curse of knowledge. It’s impossible for our brains to remember what it was like before we knew the thing we now know. When we marinate in the juice of our own startup ideas all day long, we forget how to rewind the tape. But speak simply, and suddenly the pitch becomes accessible, relatable, memorable. Simplicity is respect. Clarity is a gift (as is feedback, but that’s a story for another day...)
And finally: precision. The difference between those who practiced and those who memorized or improvised could not be more obvious. The founders who treat their pitch like a craft — who put in the reps, test and tweak, scratch what’s not working, iterate — those founders have a fluidity and ease that you simply cannot fake.
Design thinking isn’t just for product development; it’s for storytelling. Try, fail, try again. Practice your story so much that the words don’t sound rehearsed. Confidence doesn’t come from perfection; it comes from familiarity. Founders who practice become nimble, and that nimbleness makes them believable (see: authenticity).
Founders who embrace authenticity, empathy, and precision craft better stories. Stories that are rooted in who they are, designed for an audience whose humanity they respect, and delivered with the kind of clarity and confidence that only comes from putting in those reps.
-Amy
Worth Your Time
At first glance, 1929 might look like a history book. But for entrepreneurs, it’s more like a case study in human behavior under extreme optimism and sudden uncertainty.
Sorkin’s account of the 1929 crash goes well beyond markets. It’s confidence, leverage, storytelling, and decision-making when momentum replaces discipline. Those dynamics feel uncomfortably familiar today. Sure, the technologies are different. So is the speed. But the psychology of building, betting, and believing is the same.
Here’s why this book matters for founders now:
Leverage hides fragility.
In 1929, leverage amplified gains until it exposed structural weakness overnight. For modern entrepreneurs, leverage shows up as aggressive burn rates, dependence on future funding rounds, overhiring, and assumptions that capital will always be available. The book is a reminder to ask a simple but powerful question: What breaks if conditions change?
Narratives can outrun fundamentals.
Sorkin shows how optimism and storytelling drove behavior long before the data justified it. Entrepreneurs today operate in similar narrative-driven cycles around technology, growth, and scale. The founders who endure learn to build businesses that work even when the story cools.
Cash creates optionality.
One of the clearest lessons of 1929 is that survival often came down to liquidity. For startups, revenue, cash discipline, and operational flexibility matter more than valuation when sentiment shifts.
Resilience matters more than prediction.
Few saw the crash coming with precision. Many ignored warning signs. The entrepreneurs who last aren’t the ones who time cycles perfectly; they’re the ones who design companies that can withstand volatility. It’s a good reminder that the real entrepreneurial superpower is humility.
In an era defined by AI acceleration, compressed decision-making, and rapid change, 1929 reminds entrepreneurs that while the tools evolve, the risks rhyme. Because of that, understanding history is what makes you prepared.
And in entrepreneurship, preparation is a competitive advantage.
Tools We’re Tinkering With
Editor’s note: All resources suggested in this section are based on our opinions. These aren’t affiliate promotions and we don’t generate commissions.
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