I run mastermind sessions for founders working on their fundraising narratives. It's one of the services I sell, and it's where some of the best work happens.

A few weeks ago I was on a call with two founders. One of them had a background that was absolutely stacked. PhD from a top university, stint as a VC at a top firm, time at startups. Smart guy overall.

But when he walked me through his pitch, I was confused. And honestly, a bit concerned.

The use case of his technology he shared didn't add up. It didn't sound compelling. It definitely didn't sound like a good enough reason for someone with his background to be spending his time on it.

So I bluntly told him I didn't understand.

I kept asking clarifying questions, trying to grasp why he was going after this specific market. What was I missing? Why this angle?

And that's when something shifted.

As this founder started wandering around verbally, trying to explain himself. Then all of a sudden, he hit a different part of the business.

Words started pouring out of him.

His tone went up. His pacing accelerated. He got more animated, leaning in. He was excited.

The thing he started talking about was a different application of his technology. One that didn't sound as consumer sexy as what he'd been pitching. One that, to some people, was controversial. Maybe even a "bad idea."

But here's a thing I always repeat to founders… VCs don't know markets like founders do. If you're super excited about something in the face of people calling it a bad idea, that can sometimes be one of the best signals.

In this session, he only went for a couple minutes but hit cadence that was rambly. Not a confused rambly or an uncertain rambly…  it was a super excited rambly like he had too much to say and wanted to make sure we heard it all.  

When he finally stopped, I said, "That. That's what we should focus on."

I explained why his energy made me believe. Why it suddenly made sense to me.

He was sort of surprised. And then a bit embarrassed that he hadn't included this before and had listened to other investors who tried to discourage that path.

From there he went back to the refactor his pitch around the thing that lit him up and truly excited him. I only gave him a few days to refactor his story (the short deadlines is sort of the point of these masterminds) so I was a bit nervous as to what he’d come to our next session with.

I shouldn’t have been nervous. When you are truly into the story you tell, it comes out awesome. His next version was great. It made way more sense. He sounded so much more in control.

Here's what happened: the founder had been pitching an application of his technology that other people had planted in his head. It sounded good on paper. It checked boxes. But it wasn't the thing he actually believed in.

That's why his pitch felt flat.

The moment he started talking about the thing he genuinely cared about, everything changed. Not just for me as a listener, but for him as a founder. The energy transferred. The details became more convincing.

I'm constantly looking for these moments when I work with founders on their narratives. It's a massive unlock.

I call it the ramble test.

Look for the thing about the opportunity you're working on that REALLY fires you up. That makes you go off script and ramble excitedly. That pumps up your heart rate like you just won a competition.

Now check your deck and narrative. Does it include that element somewhere?

It must.

Sometimes this comes up naturally when I'm just having a loose discussion with a founder about what they're working on and why. I'm trying to find when they get excited.

But sometimes I have to go in the other direction.

I'll ask them about their favorite things in the world. Hobbies. Things they love. Often it's their kids (or dog!!).

Then I ask them to describe what's great about those things. This is usually the easiest way to uncover someone's excited voice. “She’s just the best! I love how she ….”  It’s the way they talk when they genuinely care.

Then I tell them: That's how you need to sound when you talk about your company.

If it feels awkward to inject that energy when talking about their business, that's usually a red flag. They should either look for a different angle about the company, or maybe a different company altogether.

But if they can turn that excitement on? It's great.

I know that's a tough thing to hear. But I've learned it's better to find that out early than sink years working on something you're not excited about.

I don’t say this sitting in some ivory tower with no context. I know the pain of forcing yourself to work on the wrong thing. I did it to myself.

WIth my last startup, I went out to raise for a business without that fire or excitement.  The problem is, I'm a great fundraiser, so I was able to overcome not having genuine passion and fake it successfully. I pulled it off. I raised the money. I ran the company.

But it wasn't fun.

And here's the kicker: even though I was good at faking it, I wasn’t good enough to win. Because when the hard stuff came (and it always comes), I didn't have that deep well of excitement to pull from. I had a pitch. But I didn't have the fire…and it takes all of that to win.

So yeah, if you can't find the thing that makes you ramble about your business, that's worth paying attention to.

When you do find your ramble, everything gets easier.

The pitch becomes more convincing because you're not performing anymore. You're sharing something you genuinely believe.

Investors feel it. They lean in. They ask better questions. They remember you.

And more importantly, you feel it. You stop second-guessing yourself. You make decisions faster. You recruit better people because they can tell you actually care.

The ramble isn't a bug. It's a feature.

So go find yours.

Here's how to run this for yourself:

And if you can't find a moment where you light up when talking about your company…

That's not a pitch problem. That's a company problem.

Or maybe it's just the wrong angle, and you need to dig deeper to find what you actually care about.

Either way, better to know now. 

Hope that makes sense… till next time.

Be chased,
Jason

P.S. If you want help running the ramble test on your own pitch, that's exactly what my mastermind sessions are for. Hit reply and let me know.

P.P.S. or ask me live during one of my office hours sessions. The next one is tomorrow at 12pm PST! RSVP here!

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