Avoid this “detailed” mistake - Live tape from a coaching session

Jason Yeh
March 18, 2022

A couple weeks ago, an old friend reached out and asked if I’d do him a favor. We used to play in a basketball league together so we shared some good memories. More importantly though, this was a talented friend who helped me when I was building my last company. I never forget people who have helped me in the past so I was excited to return the favor. 

He wanted me to review a company’s pitch and see if I could help refine it. He knew it wasn’t clicking but didn’t know exactly what was wrong.

The company is developing a deep science-based technology and using it to solve an urgent problem for a massively growing industry. 

Awesome, right?

Yes… but the issue is, that wasn’t my takeaway after hearing the 15-minute pitch. I needed to dig in afterwards and ask a series of questions to uncover the gems.

The pitch lost me just 2 minutes in. Without industry expertise or context, I couldn’t get excited by the content in the pitch. But as my quick one-sentence summary above shows, there is something very compelling that would excite even the least technical investor.

Learning from this

Much of what I write about regarding fundraising can sound theoretical. I often worry that founders may think it’s written for clicks or SEO. It’s not. Everything I write is based on the approach I use in real-life engagements with founders.

Instead of writing about the frameworks I would have used to help the company above, I’m sharing a recording from my session with just my coaching segments (with no identifying information included). Listen and see how it applies to your pitch:



Awesome man. I will say this. The story is very interesting. What you walked me through to me, would be... when you've caught someone's interest and you want to walk them through details of exactly why all this happens.

I think you buried the lead. Your very last slide, you talk about high PE multiples and strong moats. Everything we've done for 10 years, makes it really hard to do all this stuff. There are going to be a limited number of VCs that know this cold.

There are some, and when you go through all this, this will be like porn to them. But if you want to run a great fundraise, your challenge is: you want to be able to convince people a little bit further outside of expertise, to get excited enough to go do diligence with experts who then confirm the interest.

So when I say that, I would put myself squarely in that camp. Maybe I'd be interested in this. But as I'm walking through the story, I'm like, "Maybe?" I don't have enough background to understand.

And that's what you should be aware of when it comes to the first pass of the storytelling. What you want to be able to do is hit on a few things that get people to go, “This is interesting enough for me to spin up the diligence engine.”

You don't need to get them to be experts in thermodynamics and how the mechanics work.

You just need to be able to say enough things quick enough and keep them nodding along, to lean in, asking you questions and then go, there's enough here that's interesting. Pattern-match wise, means that you are in the right direction. I need to go to my network and find the experts to say whether or not what they're saying is true or not.

That's how I would take another pass at this. The things that stood out to me are, 10 or 15 slides in you talk about the contracts, the people working with you. That’s lead-in enough to go, there's a really quick story to tell here:

Expert scientists spending time in a field, break through in a space that is this going to really need this.

I'm a big fan of this idea of addition by subtraction. I think you're taking much too long to tell the important parts of the stories. The first four or five slides could be done in half a slide.

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