Hey friends, it’s Jorian—welcome to Into the Ring. I’m a startup fundraising coach and have worked with 60+ founders who’ve raised over $270M (yes, I finally got around to updating this).

Before I dive into today’s newsletter, I wanted to share a cool product I’ve been using this week (I have no relationship with them, just think it’s awesome): nextwork. As someone who’s starting a journey of becoming AI-native (for example, trying out Karpathy’s LLM wiki concept), nextwork has provided some terrific guides for me to walk through. Go check them out if you’re trying to get deeper on using AI.

In today’s newsletter, I’ll share a 1min take on angel groups, provide a rundown of the Tier 1 VC deals from last week, share my recommended VC essays & podcasts, and do a deep dive on startup graveyards and how they impact fundraising.

As always, thank you for being part of this Into the Ring tribe of 1.9K+ startup founders and operators/investors from OpenAI, Anthropic, a16z, Lightspeed, etc. If you think someone else might like this newsletter, they can sign up here.

Now onto today’s newsletter!

A LinkedIn post I wrote this past week struck a nerve with many founders (my DMs went a bit crazy with stories).

And it was a rant about a type of “investor” that’s been getting under my skin.

These are wealthy folks who want to play Mark Cuban for an afternoon without actually cutting any checks. They ask founders tons of questions, keep requesting more info, and then three months later pass.

It riles me up because founders pour their time & energy into these conversations, only to be consistently let down.

The #1 giveaway of these kinds of investors? They belong to an angel investor group.

These groups sound great on paper — instead of pitching 30 angels individually, you get them all in one room. In practice, they pass the buck to each other and nobody decides anything, even after months of weekly meetings. For a $50K check, they'll run a more in-depth process than a Tier 1 VC would run for a $15M check.

Not all angel groups are like this, but most just aren’t worth the squeeze. I recommend putting them dead last on your priority list, and never put your eggs all into one basket. It’s much better to run a thorough process with dozens of VCs & angels than rely on one angel group who leads you on.

Anyone else got an angel group horror story? I’d love to hear it.

Founders, you probably don't want to hear this, but you're almost certainly not the first person to have your idea.

Yes, I know your idea feels new, and you've been thinking about it for a long time. You've talked to customers, you've built out the product, you've even mapped out the competitive landscape. And as far as you know, no one is doing what you're about to do.

But here's the thing. As a founder you're only coming across a few startups, and maybe none in your space. Whereas a VC sees over 1,000 pitches a year, and if they've been at it a decade they've seen well over 10,000. So while you think you might have a new idea, when you walk into a meeting with a VC they're thinking through the dozens of founders who have pitched similar ideas.

And that montage of past founders they've seen is what's playing in their head as you're pitching them.

Try stepping inside the shoes of a VC. You're sitting across from a founder who's pitching some AI tool for legal workflows. As the founder talks, your brain is doing two things. Yes, you're listening to their story, but you're also pattern matching against every previous founder who's pitched you something in this space — what they claimed, how it went, who's still around and who isn't.

If the founder sitting across from you doesn't acknowledge any of that history, you start to wonder — do they even know about company X? They raised $30M doing this in 2022 and quietly wound down last year. And you as the VC probably won't say it out loud — it might even just be a subconscious thought.

So that's the startup graveyard. The VC is always thinking about it, whereas you might not be.

When founders hear "oh there's a startup graveyard in your space," they might think it means the same thing every time. But it doesn't. There are roughly three tiers to a startup graveyard, and each calls for a different response.

1. The structural graveyard: there's a real reason this category hasn't worked, and you didn't know. This is the worst case scenario. If you're not aware of the structural reason why something hasn't worked, you're probably about to hit the same wall the previous founders did. The VC realizes it and you don't. And you really need to fill that gap before you start fundraising, not while you're pitching.

2. The financial graveyard: multiple founders have tried to build this, VCs lost their shirts, but there's no clear structural reason it can't work. Maybe the timing was wrong or the tech wasn't there. Maybe distribution was impossible pre-AI. This is workable, but you need a real answer for what's changed and why now is different.

3. The crowded graveyard: some companies did okay, some didn't, there are even winners in the space. This is less a graveyard and more about strong competition. And so here the question shifts — it's not about why didn't this work, but it's more about why is there room for you?

Understanding which graveyard tier you're in is important in putting together your pitch.

I want to share two examples from my own work that are on opposite ends of the spectrum.

1. An edtech founder who got caught flat-footed. Two weeks ago a founder came to me in the middle of their fundraise. A VC had asked them in a meeting about a different edtech startup that had tried something similar a few years back. The founder hadn't heard of them, so after the VC call the founder looked the company up and it turns out this startup had raised $45M doing pretty much the exact same thing, only to shut down. This made things real awkward because the VC had spent the whole meeting wondering if the founder even knew that the predecessor existed.

2. The cybersecurity founder who walked in well-prepped. A cybersecurity founder I recently met knew every startup player in his space. The active ones, the dead ones, the ones who'd pivoted, and even the buying patterns of enterprise security teams over the past decade. So when VCs asked about the competitors or the market, he had specific answers ready. After meetings with VCs, they weren't just impressed — they actually treated him as someone who'd earned the right to be in the room.

Both of these founders had startup graveyards they were dealing with, but they had prepared differently. And this led to completely different VC reactions.

Now, a quick caveat. I'm not saying you need to be the world's foremost expert on your space to raise. Plenty of founders have done well coming into a space fresh — sometimes a fresh perspective is exactly the thing that's needed.

But even if you're taking a deliberately novel angle, it's still really helpful to know what startups have tried before and why they didn't make it. Because this is the stuff that's in the VC's head when you're pitching them.

Here's one thing you can do that many founders skip: actually reach out to the graveyard founders, the ones whose startups didn't make it. Sure, they might have a bitter view about venture capital and you can't read into everything that they said, but most of these founders will tell you things you genuinely cannot learn any other way. What they tried, what didn't work, what they'd do differently, even whether there's a structural issue with the market itself. It's the kind of shortcut very few founders take, and the ones who do walk into VC meetings much better prepared.

There's no way to change the fact that the VC likely has seen many more startups come across their desk than you have. But the imbalance is fixable . A few days spent on research — competitors, predecessors, dead companies, conversations with founders who've tried in your space — and you'll walk into VC meetings knowing better what they've seen before. So you can pitch with that in mind.

Founders, you've got this. If you do the work and know your graveyard, it'll make it much easier to run a high-quality startup fundraise.

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I’ve helped 60+ founders run high-quality fundraises and raise over $270M. Check out jorianhoover.com to read founder testimonials and learn more about my approach.