#037 | From Spark to Substance – How to Get the Second Date

Yayyyyy!  You did it! You just finished your pitch.

Maybe the investors smiled. Nodded. Even asked a few follow-ups.
And now you’re sitting there wondering:

“Did it land?”
“Should I add more?”
“Do I keep talking?”

This moment - right after the pitch - is where founders lose the second date.

They start to think…

Now what?

This is where most founders panic.
They start talking.
They shift into “convince mode.”
They repeat the pitch.
Or worse… they start overexplaining.

Why Founders Talk Themselves Out of the Second Meeting

You’ve probably seen it - or maybe you have even done it yourself (I know I have🫣)

• The pitch ends… and you just keep going

• You get nervous when there’s a pause

• You fill the room with extra data, caveats, or credentials

• You don’t leave any space for the investor to ask anything
  
  

And I get it! Been there - done that.
We follow our instinct:
Fill the silence. Re-explain. Add more proof....

Most founders think more detail builds confidence.
But here’s what actually happens:

- The energy drops
- The curiosity fades
- The investor gets overwhelmed - or worse, indifferent

Now is not the time to convince.
It’s about building trust.
Not by talking more - but by deepening the relationship.

The way to get the second meeting isn’t by saying more.
It’s by saying less.
It’s time to shut up.

Let them ask. Let curiosity spark.

The Trap: Talking Instead of Listening

Here’s where founders go wrong:

- They try to “re-pitch”
- They over-answer instead of asking questions
- They overwhelm instead of building dialogue

But what investors really want to know is:

• Can I trust this person when things get messy?

• Will I enjoy working with them long-term?

• Do they take feedback well?
  
  

This isn’t about winning a deal.
This is about starting a partnership.

Spark Interest - and Earn the Second Date

Getting the second meeting isn’t about being more impressive.
It’s about being more intriguing. (just like in dating...)

Here’s how to leave them wanting more:

1. Say just enough - then stop

• End your pitch with clarity.

• Then resist the urge to keep talking.

• Let the silence land. Let them lean in.
  
  

This is the magic moment.
Think of it like flirting - don’t try to get to second base.
You’re not asking for a commitment.
You’re inviting interest.

2. Invite curiosity - don’t overload

A great pitch doesn’t answer every question. It creates them.

Phrases that spark curiosity:

• “There’s a whole story behind that - happy to share if you’re curious.”

• “We found something counterintuitive in our early traction - it surprised even us.”

• “It’s a bit different from how most people approach this - but that’s why it works.”
  
  

These nudges give investors a reason to ask.
And when they ask - you’ve got engagement.

When answering:

• Keep it simple.

• Don’t treat it like a test.

• Short, calm answers signal confidence.

• Long-winded defenses signal doubt.

And if you don’t understand the question - ASK! 
Don’t start rabbling about other things…

3. Let them talk

Founders often dominate the room. But real interest shows up in conversation.

Ask back:

• “What’s your initial take?”

• “Is there a particular angle you’d want to explore further?”

• “What kind of signals do you usually look for at this stage?”
  
  

You’ll learn more in three minutes of dialogue than in your whole deck.
And you’ll show you’re not just here to pitch - you’re here to build a relationship.

Remember: you’re evaluating them, too.
Ask:

• “What do you typically look for at this stage?”

• “What would you want to see next if this moved forward?”

• “What’s your preferred cadence with portfolio companies?”
  
  

This shows you care about fit, not just funding.

4. Close the meeting with confidence

You don’t need to sell. You need to signal readiness.

Dare to ask about the next step. It shows professionalism, confidence, and respect for both your timetables.

Examples:

• “Let me know if there’s anything else you’d like to see.”

• If they want a second meeting right away: align calendars directly and ask what they’d like to focus on, so you can prepare the right materials.
  
  

Soft. Respectful. Confident.

5. Follow up fast - and light

If the meeting ends with interest, follow up quickly! Superimportant! I would say within 24h.

Even if they have asked for a lot of extra material, you can just send them an email thanking them for a great meeting and that the requested documents will be sent over within the next few days.

Your follow-up should:

• Be short and personal

• Reference something they reacted to or asked about

• Offer one clear next step (not a menu of options)

• Attach only what’s relevant
  
  

Example:
“Thanks again for the great conversation today. I’ve attached our 1-pager and a bit more context around the early pilot you asked about. Happy to go deeper on anything if helpful.”

That’s it.
Keep it human. Keep it clean. Keep it tailored.

6. Stay in conversation mode - but don’t rush it

It’s normal if investors don’t get back within a week, especially if they need to pitch it internally to the rest of the team. So don't start harassing them after 2 days...

But don’t wait too long to follow up and send them a reminder.
They see thousands of pitches. If you wait too long, they will forget.

Follow up, keep momentum, and if for some reason interest is fading then drop them fast and focus on someone who’s truly engaged.

I see too many founders chase investors who aren’t really interested.
They follow up for months, sending endless documents and decks - only to waste precious time.

This is no longer about “pitching.”
It’s about partnership-building. And if they are not into you - they should not be worth spending time on.

You’re not there to convince. You’re there to find collaboration..

And you’re showing them the version of you they want in tough times: clear, thoughtful, grounded.

Takeaway

You don’t get the second meeting by cramming in more data.
You get it by creating space for curiosity to grow.

So next time, try this:

• Say just enough - then stop

• Invite a question instead of giving more answers

• Follow up fast, with clarity and confidence

• Focus less on “closing” - and more on building a reason to continue
  
  

Your job after the pitch isn’t to push.
It’s to stay interesting.

Because they already saw the spark.
Now show them you can turn that spark into something real.

From here on, it’s not about chemistry.
It’s about credibility.

Show them they were right to say yes the first time.
You don’t need to close fast.
You just need them wanting to keep dating you.