#079 | The moment I stopped chasing the "wow" and started chasing the second date

Why Clarity Beats Impressive - Every Time
I was sitting in a room full of investors last month, watching back-to-back pitches.
Some founders were polished. Perfect slides. Rehearsed delivery.
Industry jargon stacked neatly on top of more industry jargon.
And they were completely forgettable.
Then one founder walked up. Slightly nervous. No fancy transitions. But he opened his mouth and within 45 seconds, every investor in that room was leaning forward.
Why? Because he made us understand. Instantly.
Not impressed. Not dazzled. Just… clear.
#PerfectPitch
Here's the trap I see founders fall into constantly:
They prepare their pitch like they're writing a business school case study.
They layer in market sizing, technology architecture, competitive moats - all the things that sound serious.
And the result? The more they add, the less the investor remembers.
The faster an investor understands what you do, the more likely they are to want to know more.
That's the whole game. Not a slam dunk. Not a standing ovation. Just: make them curious enough to ask the next question.
When I coach founders, I spend roughly 70% of our session on one thing - stripping the message down until the value is undeniable and impossible to misunderstand.
Three questions I come back to every single time:
- What problem do you actually solve?
- How does your product create real value - for a real person?
- Why should someone care enough to remember this tomorrow?
If you can't answer those three things in under 60 seconds - in plain language - your pitch isn't ready.
The strategy isn't the problem. The clarity is.
So What Does a #PerfectPitch Actually Look Like?
It's not the one with the best deck. It's the one that earns the second meeting.
Here's what I coach founders to focus on:
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Lead with the problem, not the product. Investors invest in the size of the problem, not the elegance of your solution. Make them feel the pain before you offer the cure.
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Kill every buzzword that doesn't earn its place. "AI-powered," "scalable ecosystem," "omnichannel synergies" - if it doesn't add meaning, it only adds noise.
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Use your actual voice. The pitch you've rehearsed to sound "investor-ready" is usually worse than the way you explain it to a friend at dinner. Go back to that version. Be authentic.
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Let your energy do the heavy lifting. Investors back people before they back products. If you're not visibly excited about what you're building, they won't be either.
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End with curiosity, not a close. You're not trying to get a yes in the room. You're trying to make them think "I want to know more." That's the win.
I'm seeing more and more accelerator programs ask me to work specifically on the 1-minute pitch with their cohorts. Not the 10-minute deck. Not the financials. The 60-second version.
Because when you can nail that - when you can hold someone's attention and spark genuine curiosity in under a minute - the longer conversations become easy.
There's no such thing as a pitch without nerves, without imperfections, without moments where you wish you'd said something differently.
That's not what #perfectpitch means.
A #perfectpitch means:
It means clear.
It means real.
It means leaving the room with a follow-up scheduled.
Aim for that. Not the standing ovation.
Thats all for today.
See you next week!
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Whenever you're ready - here is how I can help you.
1. Deep-dive Digital Courses - Self-paced courses teaching you the essential tools and skills you need to create and deliver a fantastic pitch so you can go from “I do not know what to say” to “when can I pitch next?
2. Speaking Engagements - I have done in-person and virtual speaking engagements at a number of companies, conferences, and private events covering a variety of topics.
3. 1:1 Coaching - Due to limited time, I only work with a handful of clients each year. If you're interested, click to apply.