#036 | What to Say on the First Date (and What to Leave Out)
Last week, I wrote about how your pitch is pretty much like a first real date.
Just like a first date - you’re not there to prove your worth.
You’re there to spark curiosity. Create a connection.
Leave them wanting to see you again.
But now you might be wondering…
What do I actually say on that first “date”?
And more importantly:
What should I leave out?
Most founders overshare.
They try to explain - the tech stack, the roadmap, the metrics, the team.
They walk in thinking the more they say, the more impressive they’ll seem.
And they know that they only have one shot - so they throw in everything just to be safe.
But just like in dating, it has the opposite effect.
If you talk the whole time, you don’t sound confident.
You sound insecure.
And worse… boring.
And I can promise you that there will be no second date.
Too Much Information Kills the Spark
I get it.
You’ve worked so hard to build this.
You finally get in the room and are about to get your one shot.
You know it inside out and your brain says: “Let’s tell them all the amazing things.”
And there you go…
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“Our tech is 4x more efficient than the competition.”
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“We’re targeting a $47B market with 3 ICP segments.”
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“Our CAC:LTV ratio is 1:7, and we’re cash-flow positive in Year 2.”
Sure, It’s all… fine.
The investor nod politely… but the spark is gone.
And just like that you are forgettable.
Because people don’t connect to data. They connect to people.
You’re trying to sound smart.
But what investors really want is clarity.
You’re trying to impress.
But what investors crave is connection.
Don’t forget - investors invest in YOU.
So how do you speak like a human — not a pitchbot?
Connection Beats Perfection — Every Time
If you’re wondering what to say - and how to say it - here’s how I coach founders to stop flooding and start connecting.
1. Start with a moment - not a metric
Don’t lead with, “The market is $47B and growing.”
Lead with a moment that made it personal. Start with a story. And be specific.
“2 years ago when I walked into my forest to check out the latest harvest - I was shocked. The machines had totally destroyed the soil, hurt surrounding trees and worst of all - they had messed up the biodiversity. This was a forest that had been with us for 7 generations. I was devastated. I couldn’t stop thinking about how to solve this problem.”
That’s when people lean in. Because that’s when they feel you.
Humans connect through stories - not spreadsheets.
Stories build emotional context. They show why you care.
That’s the opening scene, the hook, the part they’ll remember after 20 other pitches.
2. Show your face before your features
Before you talk about what you’ve built, share why you built it.
Let them feel your frustration, your conviction, your reason for showing up.
A lot of founders hide behind their product.
But the best pitches start with you. And your passion.
Investors fund people they believe in - not just ideas they understand.
3. Lead with clarity, not complexity
You don’t have to prove how smart you are.
In fact, trying too hard to impress usually makes things harder to follow.
Say it simply. Skip the jargon. Use simple, confident language.
Use words you’d actually use over a coffee with a friend.
If they understand you fast, they trust you faster.
Clarity shows confidence. Complexity is camouflage.
4. Speak like a person - not a pitchbot
Ditch the buzzwords. Kill the acronyms.
Speak in full sentences. Let your energy show.
If you’re excited, let it through. (Passion is contagious…)
If you’re unsure, own that too.
If you fumble a line, smile and keep going.
Founders think they have to perform.
But investors are just trying to figure out if they’d enjoy talking to you again.
5. Don’t aim to impress - aim to connect
Let your personality come through. Let your weirdness, your edge, your truth show.
Don’t polish the personality out of your pitch
If you’re quirky, own it.
If you’re intense, channel it.
If you’ve got a weird metaphor that somehow makes it all click - go for it.
What makes you different makes you memorable.
That’s what makes people lean in.
The best pitches feel like real conversations with real people.
Why This Works
Because investors aren’t just sitting there with a spreadsheet in their head.
They’re imagining what it would feel like to work with you - for the next 5 to 7 years.
They’re asking themselves:
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Would I trust this person when things go sideways?
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Would I want to call them when everything breaks?
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Do I trust their instincts - not just their strategy?
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Would I enjoy the journey - or dread it?
And just like on a first date…
They’re not looking for perfection.
They’re looking for something real.
The Bottom Line
This isn’t about dumbing things down.
It’s about letting people in.
Because when you stop trying to impress - and start trying to connect - everything shifts.
You stop presenting.
You start resonating.
And suddenly, you're not pitching to a stranger.
You're talking to a future partner.
So next time you pitch, try this:
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Tell one great story instead of five stats
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Say less - with more clarity
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Show up as the version of you someone would actually want to work with
You don’t have to say everything.
You just have to spark their interest, wanting more.
Make them feel something.
Because people don’t invest in ideas.
They invest in you.
You’ve got this!
That's all for today.
I hope you enjoyed it.
See you next Thursday where I will go deeper into the last part.
Part 3 From Spark to Substance - How to Get the Second Date.