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.

In today’s newsletter, I’ll share a 1min take on getting your butt on a flight, provide a rundown of the Tier 1 VC deals from the past week, share my recommended VC essays & podcasts, and do a deep dive on the term sheet negotiations dance.

As always, thank you for being part of this Into the Ring tribe of 2.0K+ 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!

In today’s issue:

  1. Jorian’s 1min take: get your butt on a flight

  2. What funding rounds did Tier 1 VCs lead last week? (May 30 - June 5, 2026)

  3. This week’s recommended VC essays & podcast episodes

  4. Today’s deep dive on how to fundraise like a pro: the term sheet negotiations dance

1. Jorian’s 1min take: get your butt on a flight

Sometimes there’s an event or meeting that will really make a difference in your fundraising journey. It could be a founder dinner in New York or meeting a VC-backed founder (and superconnector) in SF.

Of course, there are plenty of events and meetings that waste your time.

But my message to you today is: sometimes you should just get your butt on a flight. If you are a compelling founder, getting to meet other VC-backed founders in person can go a long way in building out your network. If you have opportunities to do so, and it’s easy for you to take a flight, then pull the trigger.

The same applies to meeting VCs - sometimes meeting them in-person can be the difference between moving forward and not moving forward at all.

3. This week’s recommended VC essays & podcast episodes

  • Newsletter: “Software Is Evolving, Not Dead” (link) by Ilya Kirnos, Partner at SignalFire. Kirnos walks us through “4 arguments for the death of software, ranked from worst to best.” I quite enjoyed the read and his view on where there are real moats versus where there are not.

  • Newsletter: “The fund size is only kind of the strategy” (link) by Clayton Petty, Partner at Gradient. I always tell founders that they should deeply understand VCs - how they think about fund size, what they invest in, etc. I recommend this write-up that talks through some of the decisions a fund needs to make.

  • Newsletter: “The AI Skepticism Map” (link) by Tomasz Tunguz, Partner at Theory Ventures. With Michael Burry (of The Big Short fame) placing a big short on AI, Tunguz does a good job of helping us understand how many shorts are on AI currently, and the extent to which that number is increasing over time.

4. Today's Deep Dive on How to Fundraise Like a Pro: the term sheet negotiations dance

Imagine you've been fundraising for months, perhaps even following my advice on how to prepare and run a great process. Now you receive a term sheet from a VC. What do you do?

Many founders have the instinct to get this term sheet signed right away and get rid of the uncertainty. They want to move past fundraising and get back to building.

This is a common instinct that founders have often because negotiating feels uncomfortable and it’s just easier to get it done with and sign the term sheet after a quick negotiation.

Rushing term sheet negotiations loses leverage

I'm here to tell you that rushing negotiations is an instinct that you don't want to follow and that can hurt you when finalizing your term sheet.

This is because rushing gives back leverage to the VC at the exact moment it swung to you. All of the past months that you’ve been prepping & executing on your fundraise, you were trying to get a VC to a “yes".

Now a VC has said “yes” and so the question is no longer “will they invest?” but rather “which version of this deal you’ll accept?” … And that part is yours to shape.

The stakes here are big. I’ve seen founders who’ve rushed term sheet negotiations and lost out on some of these terms:

  • VC voting rights provisions

  • additional board observers

  • higher liquidation preferences

  • very strong anti-dilution provisions

Not only that, but rushing a term sheet means you don’t give time for a competitive term sheet to come in from a different VC. Even if you don’t prefer that other VC, having a competitive term sheet is the single best thing you can do for your term sheet negotiating position.

I saw this firsthand last year. I worked with a founder who received a term sheet on a Tuesday and wanted to sign it by Friday. I suggested he slow things down and get back to the VC with some high-level reactions, do a round of founder reference calls, and really understand which headline terms he wanted to negotiate. The next week, this founder received a competitive term sheet from a second VC which helped him improve the terms on the first term sheet, including a higher valuation and 1x liquidation preference.

Term sheets are rare, and that’s your leverage

So why does leverage move to you when a VC offers you a term sheet?

Well you need to understand that term sheets are rare. A low single-digit percentage of meetings VCs take with founders end in one; VCs just don’t hand them out like candy.

Your champion partner at the VC firm has likely staked internal credibility on winning the deal and they want to be seen as a partner who can win. Plus, there’s now real economic upside on the line for the VC, so they want to get the deal closed. Walking away from a term sheet feels expensive to them now.

How to “throw a jab” and keep the dance alive

Here are some things you can do once you've gotten a term sheet to "throw a jab" and keep the dance alive:

  • When you get the initial term sheet, share some high-level reactions over email which will take the VC a day or two to respond to

  • Ask for founder references (and do your own), which gives you great information and also buys you time

  • Have some back-and-forth over emails and calls so that you can better understand their position and what they're willing to budge on

  • Once you feel like you have enough information and have done your due diligence, then you can really hit hard on your priority terms and work through the rest of the term sheet with your startup lawyer by your side

Remember, keeping the dance alive wins you multiple prizes. It gives space for a competing term sheet to show up (which is the strongest negotiating lever you have) and it also adds a little bit of friction for the VC that often makes them lean in and flex more on terms.

Keep dancing, but don’t ghost the VC

One mistake you can make by trying to dance with the VC is to ghost them. You want to throw a jab, take a jab, keep moving the ball forward. If you freeze or ghost then the VC could read it as you're disinterested or just pure shopping, and I've actually seen VCs pull the term sheet because of that.

Failing in negotiation often lies at both ends of the spectrum: throwing away leverage through rushing too fast and on the other end, having the VC bow out through freezing or ghosting them.

Negotiate everything before you sign the term sheet

One last note. Make sure you get every single term negotiated BEFORE you sign the term sheet. Sometimes VCs will try to get away with sharing a term sheet that only has high-level terms and they'll say, "We'll figure out the rest of the terms after you sign." Don't agree to that.

This is because once you've signed a term sheet, you're pretty much locked in. It's exclusive and you can't shop for a period of time. All the dancing and your ability to throw jabs happens in the pre-signature time frame. So you want to make sure to negotiate, alongside your startup lawyer, while you still have leverage.

Founders, receiving a term sheet is when you’ll have the most leverage with a VC. Don’t be so eager to “get it done with” that you sign away your leverage.

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