Hey friends, it’s Jorian—welcome to Into the Ring. I’m a startup fundraising coach and have worked with 50+ founders who’ve raised over $190M.

The past two weeks I’ve been on the road. First I was in New York meeting with over a dozen founders & VCs, and then I traveled to a few other cities to meet founders I’m coaching. Thank you to everyone who made time to meet me — it’s always more fun to do IRL!

One thing I’m getting inspired by recently is just how AI-native many of the founders I’m working with are becoming. And it’s making me roll up my sleeves, review the likes of Andrej Karpathy & others’ Claude Code setups, and figure out how I can streamline my own operations. If you have any favorite Claude Code setups and/or YouTube videos, please send them my way.

In today’s newsletter, I’ll share a 1min take on why you should spend time on VC Twitter, provide a rundown of the Tier 1 VC deals from the past two weeks, share my recommended VC essays & podcasts, and do a deep dive on determining if your startup is VC-backable.

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!

One of the biggest problems I see with founders fundraising? Not being able to step into the shoes of a VC.

This happens not only with first-time founders, but also founders who previously built a non-VC-backed business.

If you can't step into the shoes of a VC and understand how they talk & what they care about, then it's going to be much harder to pitch them.

I see this quite often — I'll listen to recordings of a founder's conversation with a VC, and watch the VC's eyes glaze over mid-pitch.

One solution: spend some time on VC Twitter. Pretty much every VC is on there, and it's a great way to pick up on how they talk, which areas they're getting excited about, and the inside baseball you'd otherwise miss.

At minimum, you'll have better small talk material going into VC meetings. But ideally, you'll start navigating these conversations in a way that actually gets you funded.

You’re asking the wrong question.

Every few weeks I have a conversation with a founder who's been told, by someone they respect, that VCs aren't for them. They're not building a $10B+ company, the logic goes, so they should stay away.

Most of the time, I think this advice is wrong. Or at least, it's answering the wrong question.

"Is my startup VC-backable?" gets treated as a yes-or-no test on the business. But it isn't. And founders who treat it that way end up either passing on VC money they could have safely taken, or — much worse — taking VC money in a setup that traps them years down the road.

The "$10B-or-stay-away" framing is pitched as protecting founders from a bad fit. But it misses the real mechanism.

VC-backability isn't really about your business in isolation. It's about the fit between your business and a specific fund. The same startup, with the same founder and the same numbers, can be a great deal for one VC and a disaster waiting to happen for another.

Step into the shoes of a VC for a moment. A $200M exit on a $5M check is a really good outcome at a smaller, stage-focused fund — they're happy. That same $200M exit on that same $5M check, but written by a multi-stage fund managing billions, is a write-off they would have rather avoided. The startup did the exact same thing in both cases, but one VC is celebrating and the other is frustrated.

So if it's not the check size that determines whether you're going to regret this deal in five years, what is it?

Two things:

The lock-in scales with what you sign and who you sign with, not with the dollar amount on the wire.

Let me make this more concrete with a side-by-side.

Imagine two founders, both raising a $5M seed round. Three years later, both get an acquisition offer in the $200M range — same business performance, same exit on the table. The only difference is who's on their cap table.

The above is stylized, but I've seen versions of both play out in real life.

A founder friend of mine has raised about $45M across three rounds for his fintech startup. He's now sitting on an acquisition offer in the low 9-figures, but his Series B VCs aren't on board — they want him to keep going and swing for a billion-dollar-plus outcome. The contract piled up rights across three rounds, and the counterparty's economics need a much bigger outcome than what's on offer. Both halves working against him.

On the other side, I came across a founder in cybersecurity who raised $5M and never needed to raise again. He's now got opportunities to exit in the low 9-figures, and while the VCs would love a bigger outcome, a 9-figure exit is genuinely a good return for them — and they don't have the control or economic rights to block it anyway. Completely different position than my fintech friend.

So when you're sitting across from a VC, deciding whether to take their money, the question isn't "am I VC-backable?" It's two questions:

The first one is what most founders pay attention to, and even then often only at the surface level (focusing on valuation and ignoring the rest of the term sheet). The second one is the one most founders skip entirely — and it's often the bigger driver of how the next 5-10 years play out.

If you're going for a low 9-figure outcome, a small seed-stage fund writing a $3M check might be a fantastic partner. That same low 9-figure outcome with a multi-stage fund on your cap table after three rounds? Recipe for the kind of conflict my fintech friend is living through right now.

So stop asking if your startup is VC-backable. Ask if this specific deal — what you're signing, and who you're signing with — sets you up for the outcome you're actually going for.

Enjoyed this newsletter? Forward it to a friend and have them sign up here.

Are you a founder and want to run a high-quality fundraise? Apply to work with me.

I’ve helped 50+ founders run high-quality fundraises and raise over $190M. Check out jorianhoover.com to read founder testimonials and learn more about my approach.