The best investment pitch I've ever seen

5 lessons to help you raise tens of millions of dollars

January 16, 2023
min read

Hey y'all.

I spent some time in Boulder this week working with the Antler VC team (where I'm a Venture Partner) and now I'm off to SF to speak at Stanford this week.

2023 is going to be a wild ride and if you're planning to fundraise, or just want to become ridiculously persuasive then today's deep dive is for you.


DEEP DIVE: Investing with the Joker

I recently had dinner with a partner at a major tier 1 VC firm. “It’s tough out there,” she told me, “and only the best founders will get the capital they need.”

Her message is simple: For those of you gearing up to fundraise in 2023, you’ll have to be at the top of your game.

That means getting your pitch in order, and as usual, I don’t mean just making sure your data is organized or your slide deck is in the proper font. I’m talking about mentally preparing yourself to walk into your pitch meeting and give VCs no other choice but to invest in you.

How, you ask? By implementing some pitch tools that come from a rather unlikely place.

A couple of weeks ago, I shared a breakdown of a scene from the TV show Mad Men, and I explained why I think it’s one of the most masterful advertising pitches of all time.

This week, I provide a breakdown of another fictional investment pitch of sorts. This one comes from the 2008 Christopher Nolan film, The Dark Knight.

You’ve probably seen this movie dozens of times, and rightfully so—the cinematography is captivating, and Heath Ledger’s performance is right up there with the all time great performances. And while you likely know the scene I’m about to share with you, I bet you’ve never realized how instructive it can be for your own quest for investment.

The scene in question comes about 40 minutes into the film, when the mob bosses of Gotham are trying to figure out how to rid themselves of the Batman. The caped crusader has put a wrench in their nefarious works, and they are in need of some help.

Enter Ledger as the Joker, who sells them on the idea of teaming up with him.

It may not seem like it, but the Joker’s offer to join forces is absolutely an investment pitch, and there are five main lessons you can take away from it.

You can watch the full scene here.

Now, let’s break it down.

Lesson 1: Lead With a Compelling Hook

Attention is critical.

You may be selling the cure to cancer, but unless you have your audience’s attention from the jump, it won’t matter.

In this scene, the Joker needs the mob’s attention. How he shows up will frame the rest of his pitch.

He starts with a diabolical laugh. The whole room turns to see where such an insane noise is coming from.

I’m not suggesting that YOU start by laughing like a cartoon villain, but rather to find that real world analog. How could you begin that would be so compelling that you would immediately have the entire room’s attention?

Lesson 2: Establish Your Persona

Very early in the pitch, you need to establish your persona. Who are you as a founder?

In Socractic terms, this rhetorical appeal is called ethos—establishing your credibility and authority. In real world terms, this might look like speaking to your experience or demonstrating the characteristics that make you appealing: your work ethic, your passion, your intelligence and creativity. You want to SHOW, not tell your audience these things through verbal and nonverbal cues.

How does the Joker establish his persona? His appearance, for one. You can tell this guy is not your average villain. You’re not at all surprised when, at the end of the scene, he opens his coat to reveal an arsenal of hand grenades.

He also conveys his tenacity and ability to think on his feet. When one of the goons comes after him, he deftly dispatches him with a clever “magic trick.” It’s at once compelling, creative, and confident.

The Joker is twice accused of being crazy, which he flat out denies. He doesn’t belong in Arkham Asylum, no. He exudes what I call “delusional confidence,” the type of calculated crazy that geniuses are made of. The investors think, huh, he’s just crazy enough to pull this off.

The Joker also conveys his confidence in his ask.

He wants HALF of the mob’s spoils—a price that seems absurd at first. But not in the context of the way he frames his pitch. Let’s take a look at how he does that.

Lesson 3: Present Your Audience’s Problem

One of the best ways to pitch your idea is to set up a classic problem/solution framework. Your customer has a pain that only you can solve. Your audience, the investor, needs to feel that pain of the customer. They also need to feel their own pain of potentially missing out on a once in a lifetime opportunity.

In this scene, the Joker establishes the problem the mobsters are all dealing with. They’re scared that Batman has destroyed their business and they can no longer operate as they always have. He does this by pointing out the mob’s FEAR.

This is brilliant, because not only is fear one of the most visceral emotions, but it also carries additional negative emotions. For these mobsters, it also brings shame and self doubt. They’re the MOB! They’re supposed to RUN Gotham! And some guy dressed in tights and a cape is shutting down their business? How embarrassing.

By identifying the problem, Joker sets his audience up perfectly to hear what he has to say next.

Lesson 4: Offer a Solution

Of course providing the solution naturally follows identifying a problem. But it’s a lot trickier than it seems. This is typically when I see founders trot out their service. It’s the slide in the pitch deck that showcases the product, how great it is, and how it’s going to solve the problem.


The product isn’t the solution. YOU are the solution. Remember, investors aren’t investing in your product. They’re experienced enough to know the product might pivot a dozen times before you find the right PMF. They’re buying YOU as the antidote. So sell it to them.

In this scene, the Joker introduces his solution: Kill Batman.

Duh, you’re thinking. But the brilliance is in the simplicity. Up to this point, the mob has been unable to do that. It seems like something that can’t be done. Even though his solution is obvious, the persona he’s established has created enough confidence that the mob believes he can do it.

The Joker act’s like it’s inevitable.

That’s why I always talk about the inevitable mindset that a founder must have when walking in to a meeting. In this case, the Joker believes with 100 percent certainty that he can kill Batman.  

I want you to notice something, though. At no point in this scene does the Joker explain HOW he’ll kill Batman. In other words, the features and specs of the service he’s selling is immaterial. HE is the solution they’re looking for.

Lesson 5: Close with Confidence

When you’re speaking, there are two things that always stand out to your audience: the first thing you say, and the last thing you say. In human psychology, it’s called primacy and recency.

I’ve already talked about the importance of a solid hook to engage your audience. Now, let’s look at wrapping things up.

Closing out initial conversations with confidence is one of the things I see founders struggle with the most. You nail your pitch and end with a fumbling, “um, so, yeah. I guess let me know.”

To do it right, you need to be in the mindset that the INVESTOR is the one who is going to miss out. You’re the one with the solution to their burning problem, and if they don’t get on board with you, no one else is going to help.

That’s exactly what the Joker does in this scene. He stays in control until the end. He doesn’t ask for a yes or a no, he doesn’t say “please give me your money.” He says “give me a call when you want to start taking things a little more seriously. Here’s my card.”

He does it in a way that comes from a position of strength. He knows he holds the upper hand. The mob bosses aren’t successful right now, and they’ve got a problem—a problem only the Joker can solve.

That’s what you as a founder want to do as well.

When you finish a meeting, you want to lead with that level of confidence and control that makes an investor feel that IT factor. They want to know you’re not someone desperate for money, but someone who has absolute conviction in what they’re going to pull off in the future. The investor can either get on the train or get left at the station.

When you go into a pitch asking for an investment, think about these five things. How are you hooking your audience? How are you establishing your persona? How can you dig at the problem in such a deep way that they feel pain, and how can you show you have the solution?

2023 is going to be a great year for you—but only if you’re ready with the right tools. You need to get a little more clear, a little more crazy, a little more confident.

A little more like the Joker.


I finished up the second season of The White Lotus this past week. Worth watching if you want to see some amazing storytelling, character development, and beautiful cinematography.

Raising venture capital is all about understanding the rules of the game, investor psychology, and storytelling.

We work with founders raising a Series A or later who want to dial in their strategy and storytelling to raise the right round in less time. It's what's helped founders raise $330,000,000 in the past 18 months.

If you'd like to apply, you can fill out this form to potentially set up a call.

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