3 Keys From A Pitch Coaching Session + Fundraising Fieldnotes 02.25.25

I helped a founder with their pitch, here were 3 keys from my coaching session with them about important “details"…

When I work directly with a founder, I will usually start by covering the greatest hits of my fundraising coaching, but depending on the exact situation, more nuanced guidance often comes out.

My last coaching session was with a founder whose fundraising kickoff was just around the corner. The anxiety about what happens when the rubber meets the road teased out a few key insights that I’m happy to share with you all.

Overall, here was my message:

Founders often overthink their pitch. They overthink the situation. They make things feel scarier than they need to be (I do this too).

If you think that could be you, you’re not alone. A great pitch isn’t about checking every box; it’s about making investors excited enough to take the next meeting -that can be a relatively simple effort if you think about what to include, what to leave out, and how to stay in control of the conversation.

My 3 messages to the founder below…

Message 1: What makes a great pitch deck? Keep it short.

I’ll start with an obvious one. I needed to highlight this one because even though we had spoken about the importance of brevity, the anxiety of upcoming pitches made this founder question their deck.

The tendency is for founders to treat their pitch deck like a full company report. They cram in every detail, thinking that if they explain everything perfectly, investors will be convinced. Even when coached away from this, fear of rejection can get you to fall into old habits.

Just remember…

If your deck is too detailed, investors will glaze over or miss the main point of your story. Keep it tight, clear, and exciting. Another good rule of thumb: if you wouldn’t say something in your verbal pitch, it probably doesn’t need to be in your deck (the appendix is another story).

At the end of the day, a great deck isn’t about overloading investors with information; it’s about making them want to learn more. Outline a compelling story, focus on what truly matters, and keep your deck sharp and to the point. If you can do that, you’ll set yourself up for the only thing that really matters in a pitch: getting to the next step.

Final Deck Thought: Keeping a deck short and to the point doesn’t mean everyone will like it. That’s ok -it’s part of the process. Better than a stuffed deck with a little something for everyone that no one hates but no one loves as well…

Message 2: How do I balance storytelling with data in my pitch? You don’t.

Following VC and fundraising, Twitter really got this founder confused. Some people talk about the importance of metrics in fundraising. Others said it’s all about storytelling. “How do I balance the two?”

Here’s my answer: you don’t.

If a metric helps explain why your company is exciting and why it’s going to be massive, include it. If there’s data you’re considering including because you think investors expect to see numbers, leave it out. Your job isn’t to overwhelm them with data; it’s to tell a compelling, believable story about why your company is worth betting on.

And if certain numbers aren’t great? Don’t include them. There’s no rule that says you have to show every single piece of data. The goal is to highlight what makes your business strong while staying honest about where you are.

Final Storytelling / Metrics Thought (tough love): the situation you’re running into of not being sure what numbers to include and how to tell a good story might have more to do with you simply not having a good story to tell investors at the moment. Be honest with yourself and listen to smart feedback that might hint at this.  I’m not saying your company will never have a good story, but more so it’s a better use of time to work on your company and investor relationships first before pulling together the story you want to tell to raise capital.

Message 3: How do I handle “tough” investor questions in my pitch? There are no tough questions.

Knowing that live pitch meetings with actual investors were coming up was freaking out this founder.

I get it - the spectre of scary investors trying to beat them up during a live pitch can be harrowing if you’ve never done it before. But when this founder and every other founder ask what are some of the hardest questions they need to be ready for, I kinda have an annoying answer…

If you know your company well… if you are excited about what you’re working on and think about the different ways you’re going to win, the products you want to launch, the problems you want to fix… If your favorite thing to talk about is your company (which it should be if you’re raising), then no question should be difficult.

Most of the time, what trips founders up isn’t a hard question; it’s a question they don’t have a specific answer to or one that’s asked in a way they don’t immediately understand.

The key is to remember that investors aren’t trying to trip you up; they just want to understand your business.

A founder I once advised thought he had completely botched a pitch. He ran an e-commerce brand, and during the pitch, the investor asked for his monthly net revenue. Because he didn’t know what that meant, he just said, “I don’t know.” 

“I don’t know” and nothing else wasn’t a good look.

It was such a shame because it’s not that the founder didn’t know detailed information about his sales numbers… it is that he literally didn’t know the term “net revenue.” The investor wanted to hear more about how often customers were returning his products, something the founder absolutely knew. If he had just asked, “Can you tell me what goes into your definition of net revenue?” he could have spoken at length about the topic with confidence.

So next time you get hit with a question you don’t understand, don’t guess… just ask. You probably already know the answer; you just need to figure out what they’re really looking for.

Final “tough questions” thought: One other thing is that sometimes you won’t know the answer, and saying you don’t know is ok. If you truly don’t know the answer but you have other information around the topic to share, saying you can get the answer for them quickly after is ok. As long as you can discuss tangential topics, you won’t be penalized for not knowing specifics.

Alright, hope this helps some of you get past some of that pre-pitch anxiety. Till next time!

Be chased,
Jason 

Even though our risk appetite has been dampened over the last year... we're still the best at this. USA! USA!

Yes - i was debating whether to use a no code solution or build with AI-code.. the latter is faster AND feels more flexible / durable...

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