I'm working with a founder right now on an enterprise software company addressing AI risk. Smart team, solid product, real traction.

We recently shared their core fundraising deck with a handful of investors. Just the main narrative slides, no appendix.

Within a day, I got feedback from one of the VCs: "Great story, but it's a little high level. I'd like to see more detail. Can you send the appendix slides on the technical differentiation?"

The founder immediately panicked. "Oh crap, there's something wrong with the deck."

I told him to relax. This is actually good news.

Here's what a lot of founders don't understand: the goal of your initial story isn't to answer every question. It's to make the investor want to learn more.

Learning more could mean:

When an investor says "this is too high level, I want to see more," that's a hook. They're interested. They want to dive deeper.

If the story was actually bad, they wouldn't ask for more. They'd just say "not for us" and move on.

So when this VC came back asking for the appendix, my response to the founder was: "Perfect. They're hooked."

But here's where it gets interesting…

I told the founder we'd send the appendix, but I also told him something he found surprising:

"This investor very much wants to see the deep dives... but also doesn't have the technical depth to accurately assess the viability, defensibility, or scalability of what you're building."

And I'm very aware of this element of VC diligence. But I'm always so surprised when I see it play out.

Even when investors go a level deeper into technical content, they're still using pattern matching and broad strokes evaluation. They're looking for signals that feel right, not actually validating the underlying technology.

This is true whether you're talking to a generalist investor or even an industry-specific one who probably has more context than most. The reality is they're probably not as specialized as is needed to fully diligence the underlying product, technology, or market dynamics.

But they still want to see it. And they should.

Because even if they can't evaluate it at a technical level, they're looking for other signals. Team pedigree. Revenue growth. Logos. The shape of the story. Whether it passes the sniff test.

You might be wondering: if investors don't fully understand the tech, why don't they just say so?

Two reasons.

First, it doesn't feel good to feel stupid. Investors don't love that feeling any more than anyone else does.

Second, and more importantly, part of a great company choosing an investor to join the cap table is wanting someone who actually understands the business and can provide value. If an investor is trying to evaluate a company and admits they're completely clueless on the core technology, that's not a great look. So they'll at least nod along.

When the initial story and numbers show that it's a great company, investors will often fake understanding of the technical ideas just to stay in the conversation.

This isn't dishonesty… it's just how the game works.

Because of this dynamic, founders need to understand that content has levels. And you need to manage those levels strategically.

Here's how I coach founders to think about it:

This is for everyone to consume quickly and get excited to learn more.

Simple. Clean. Fast.

No technical jargon. No deep dives. Just the broad strokes of the opportunity, the problem, and why your team is the one to solve it.

This is what gets the meeting. This is what gets the "I want to learn more."

The mistake founders make is thinking that when an investor asks for more, they should go fully technical right away.

Don't.

Layer 2 is what I call "simple depth." It's enough detail for someone with pattern recognition ability to go slightly deeper without getting lost.

Here's an example to illustrate the difference between simple depth and technical depth:

Simple depth: "Aging dogs' lifespan can be extended by up to 50% with the right treatment."

Technical depth: "The DNA construct of an aging dog is being mutated on a daily basis from input elements in their surrounding environment, including food, air quality, supplements, and psychological interaction."

See the difference?

Simple depth gives investors something meaty to sink their teeth into. It feels substantive. But it's still accessible.

This is the layer that lets investors use pattern matching. They can compare it to other companies they've seen. They can evaluate whether the approach feels differentiated without needing a PhD.

This is the real deep dive. The stuff that requires actual expertise to evaluate properly.

Sometimes Layer 2 and Layer 3 can be the same. But not always.

Layer 3 is what you send when an investor brings in their technical diligence partner. Or when they have someone on the team with actual domain expertise who can smell bullshit.

This is where you get into the weeds. This is where you show your work.

But you don't lead with this. You earn your way to this layer by nailing Layers 1 and 2 first.

Here's the playbook:

Layer 1 (core deck) is for the initial pitch. Everyone gets this. Use it to hook them.

Layer 2 (simple depth) is for when they ask for more. This is your appendix. This is what you send when they say "I want to see the technical differentiation slides."

Layer 3 (actual technical depth) is for when they show real interest and bring in experts. Don't send this preemptively. Wait for them to earn it.

And here's a thing I always repeat to founders: use this as a gating factor.

When an investor says "send me the full deck, send me your data room," you have agency. You can push back. You can say, "Of course. Just want to confirm this is a space you're excited to spend time in before I send over all the details."

If they're serious, they'll confirm. If they're just fishing for information or doing competitive intelligence, that question will make them uncomfortable.

There's a great essay by Mark Suster called "Data Rooms Are Where Fundraisers Go to Die" that I reference in a lot of my workshops.

The headline sounds absolute: "Never have a data room."

But if you actually read it, he's not saying don't have one. He's talking about when you should share it.

This is a good reminder that fundraising advice requires nuanced understanding. The headlines are often clickbaity and don't show the full picture.

The principle applies here: don't just hand over everything because an investor asked. Make them show real interest first. Qualify them.

Data rooms, appendices, technical deep dives... all of this should be shared strategically, not reflexively.

Back to the founder I'm working with.

When the investor said "I want to see more," the founder wanted to immediately send the full appendix.

I told him to hold off. Instead, we sent a note saying we appreciated the interest and would be happy to share the appendix, but wanted to confirm they were excited to dig deeper into this space first.

The response came back within an hour:

"Send the appendix!!!"

Three exclamation points.

That's when we knew they were serious. So we sent it.

And here's what I know: they probably won't fully understand all the technical depth in those slides. But they'll pattern match. They'll look for signals. They'll evaluate whether it feels defensible, whether the team seems credible, whether the approach makes sense at a high level.

And that's enough.

Because at the end of the day, investors aren't buying perfect understanding. They're buying conviction. And conviction comes from a story that hooks them, depth that reassures them, and signals that tell them this could be the one.

If you're raising capital, remember:

1. "Too high level" is often good news. If they want more, it means you hooked them.

2. Don't panic and dump everything. Use the three-layer framework. Give them what they need at each stage, not everything at once.

3. Investors will fake understanding. That's not a knock on them. It's just reality. Design your content for pattern matching, not deep expertise.

4. Qualify investors before sending depth. Make them show real interest. Don't just hand over your data room because they asked.

5. Simple depth beats technical depth in round one. Save the PhD-level content for when they've earned it.

The game isn't about making investors fully understand your technology. It's about giving them enough to believe in you, your team, and the opportunity.

Layer your content. Control the flow. And make them chase you for more.

Be chased,
Jason

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