Hi Gary,

There’s a wave of capital flooding the market—and many of my CEOs are riding it.

Six of my clients raised Series A–C rounds in the past 30 days alone—including one with a $1Bn valuation.

So today, let’s talk about the first investor meeting.

Most founders focus on the pitch. But pitching isn’t the same as selling.

Pitching is one-way. Sales is a two-way process. It’s about asking the right questions, qualifying the prospect, and guiding the conversation with intent.

Top fundraisers don’t wing the first meeting. They engineer it.

So here are seven sales techniques you can use in your next investor pitch.

1. Script Your Pitch

Stop the waffle and start iterating.

Most founders underestimate how much they improvise.

We believe we’re being conversational, but without a structure, we default to rambling. And we rarely notice—we’re too in the moment to reflect. It’s only after the call that we realise we forgot to mention our revenue trajectory or that killer customer story.

A pitch script isn’t about sounding rehearsed. It’s about consistency under pressure. It lets you:

Say things in a tight, compelling way—every time.

Catch where things land and where they fall flat.

Iterate quickly, like a product you’re refining.

Pushback: “I don’t want to sound robotic.”

The truth is scripts become natural with lots of repetition. And ironically, it’s when you don’t need to think about your words that you can be most present in the conversation.

2. Ask Power Questions

Whoever asks the questions, holds the power.

Most founders walk into investor calls trying to impress. We talk, explain, and over-justify.

But great sellers know that the one asking the questions is in control.

Founders forget that they’re also choosing the investor. You’re not just selling equity—you’re deciding who gets to be on your cap table. Your questions should reflect that.

Try these:

“What do you already know about our space?”

“What research did you do before this call?”

“What makes you think there’s an opportunity here?”

“Are you the ultimate decision maker? If not, what’s your conversion rate with your investment committee?”

“What do your best-performing investments have in common?”

And when they ask you something? Don’t always jump to your answer. Instead, try:

“What's the question behind your question? Do you have experience you can share?”

“Before I answer, what’s your hypothesis?”

“If you were in my shoes, how would you answer?”

Pushback: “Won’t I sound aggressive?”

Not if your tone is curious. In fact, you often find that the question behind their questions is the real issue, and without asking questions, you’d never find it out.

3. Sketch a Framework Live

Sketching a model is 10X more intimate than presenting a slide.

This one’s subtle but powerful. Investors don’t just want to see the answer. They want to arrive to it themselves.

Slides don't create insights because they give everything away. The investor focuses on deciphering the slide instead of following your thinking.

Insight isn’t about information—it’s about choreography .

When you draw a model live—a timeline, a 2x2, concentric circles—you take the investor on a thinking journey. An incomplete sketch sparks curiosity. The build creates tension. Done well, it feels like you’re drawing it just for them.

Pushback: “But what if the call is online?”

No problem. Connect an iPad or tablet and sketch in a notes app. Live drawing holds attention and turns the moment into co-creation—not passive consumption.

4. Check In at Regular Intervals

Feelings come first, then logic backs them up.

One of the most common mistakes is to wait until the end of your pitch to check in and ask for questions.

By then, it’s too late.

Investors don’t usually think, “Something feels off,” and they just quietly lose conviction. Then, when you ask, they find a logical excuse to back out:

“The market’s not right”

“You’re a little too early”

“I’ll have to run this by my partner”

However, you can't really be sure where you lost them—and they may not even know either. It was a feeling that grew. That’s why you need to check in regularly.

When I check in, I ask two questions, in sequence, to get them to check both their head and their gut:

“Does this make sense to you?” (the head)

“Are you 100% comfortable so far?” (the gut)

Pushback: “Won’t I seem unsure of myself?”

Not if you own the moment. Checking in signals awareness and it encourages them to be honest. And the earlier you know something’s off, the greater your chance to adjust before they rationalise their way out.

Pro tip: If the pitch is online, record it locally in 'gallery view' and watch it back, paying attention to their facial expressions. The misalignments are often invisible in real time—but obvious on replay.

5. Discuss Concerns on The Call

Don’t let them leave with doubts you never hear.

Too many founders run out the clock. The pitch ends, time’s up—and the investor walks away with unspoken concerns.

That’s why I recommend this simple structure for a first pitch meeting:

First third: Ask questions

Second third: Share your pitch

Final third: Discuss conviction and concerns

It shows maturity to invite doubts, not avoid them. Ask for both the positives and the hesitations:

“What’s the reason this could be a yes for you?”

“What are your biggest questions at this point?”

“What would help you feel comfortable moving forward?”

When objections arise, most founders jump straight to logic. Instead, try the classic Feel–Felt–Found technique:

“I know how you feel. I felt the same way. What I found was...”

This lets you connect emotionally before responding intellectually.

If they mention needing to speak with partners, go deeper:

“How would you pitch it to them?”

“What do you expect them to say?”

“If they push back, what happens?”

Pushback: “Won’t discussing concerns talk them out of it?”

Maybe. But tension is where truth lives. And if you don’t surface it in the room, it will surface later as a long 'no'.

6. Build Emotional Resonance

All decisions happen in a resonant state.

Resonance is the coaching term for emotional alignment—and it’s essential in sales.

Founders often try to remove the “no,” but forget to build the “yes.” You can remove objections all day long, but action only happens when someone feels moved.

Ask questions that open emotional doors:

“What were your favourite investments?”

“Who are your favourite CEOs to work with?”

“What are you most passionate about in life?”

When you notice energy—lightness, animation, excitement— double down.

Pushback: “Isn’t that a distraction from the pitch?”

More often than not, the investor who says yes is the one who feels a personal connection with you. Making them feel understood helps create safety.

7. Book a Meeting From a Meeting (BAMFAM)

Lose momentum, lose the deal.

A great meeting that ends with, “We’ll follow up,” doesn’t mean the deal is lost... but the momentum might be. And when momentum fades, doubt fills the gap.

Always aim to lock in the next step before the call ends.

“Let’s put 20 minutes in the diary for next week—how’s Tuesday?”

Pushback: “They said they couldn't find a time.”

If you miss the opportunity to book a call in the meeting, follow up with a hand-raiser email or message:

“I’m meeting with interested funds next week. Are you interested in joining?”

If they say yes, you move forward. If they say no, you move on.

Final Thoughts

Fundraising is a numbers game and most investors will say no. It’s part of the process.

The real mistake is treating every meeting like a standalone performance, rather than a chance to get better. The more you treat it like a skill, the faster you improve.

Keep going, stay curious and take what you learn from one call into the next.

Because you don’t need every investor to say yes. You just need the right one to.

Warmly,

How to Engineer the Perfect Investor Meeting ⭐️