the art of VC coffee chats

the two ways founders mess up coffee chats, and what to do about it

Author

Jorian Hoover
December 02, 2025

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. And welcome to the ~50 subscribers who’ve joined since last week’s edition.

Today’s newsletter will cover my take on why taking venture capital can make sense for founders, the latest funding rounds Tier 1 VCs led last week, my recommended VC essays & podcast episodes, and a deep dive on the art of VC coffee chats.

Thank you for being part of this Into the Ring tribe of 1.7K+ 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: why taking venture capital can make sense for founders

  2. What funding rounds did Tier 1 VCs lead last week (Nov 22-28, 2025)

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

  4. Today’s deep dive on how to fundraise like a pro: the art of VC coffee chats

1. Jorian’s 1min take: why taking venture capital CAN make sense for founders

I can’t believe I need to do this, but I need to defend venture capital as an asset class.

Every time I scroll on LinkedIn, I’m bombarded by posts shouting “founders should never take venture capital” or “bootstrapping is the only way” or “only raise once you have millions in ARR.” And often I see fake math that shows how after liquidation preferences, taxes, bla bla bla, bootstrapping always works better than venture capital.

Have we not forgotten the point of venture capital?

Raising venture is about dreaming big.

Yes, if you want to build a $10M business, then taking VC money is not a good choice. But if you are seriously hoping to build a billion dollar plus enterprise, then venture capital can be a great option for you.

There are countless companies core to the fabric of today’s economy that raised venture—Google, PayPal, Meta, Dropbox, Spotify, and Stripe, just to name a few. And there are over a thousand other startups who have become valued at over a billion dollars.

Where I do agree with the naysayers is that if you do plan on taking money from VCs, it’s important to know the game you’re playing. Both of you should be seeking a home run or grand slam. If you’re looking for a double, then venture capital might not be right for you.

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

  • Podcast: “Sunday Robotics: Scaling the Home Robot Revolution with Co-Founders Tony Zhao and Cheng Chi” (link) by Sarah Guo on the No Priors pod. There’s a brewing “GPT” moment in robotics, and I enjoyed this conversation diving deeper into what Zhao and Chi are building in the robotics space.

  • Podcast: “Satya Nadella — How Microsoft is preparing for AGI” (link) by Dylan Patel & Dwarkesh Patel on the Dwarkesh pod. Satya talked through their brand-new AI datacenter, in-house chips, the capex explosion, and more.

  • Newsletter: “Going Bananas” (link) by Rex Woodbury. This past week, the internet went crazy over the new Nano Banana Pro, where you can easily add celebrities to your selfies. After having some fun at the top of the newsletter, Woodbury (who’s Managing Partner at Daybreak) breaks down what this all means for startups.

  • Newsletter: “Axios Pro Rata: Crypto cooldown” (link) by Dan Primack. Dan is a writer at Axios and writes a near-daily newsletter on the latest headlines across VC, PE, etc. He opened up a recent newsletter by sharing how builders in the crypto space may actually appreciate a crypto winter (though we’re not in one yet). Relevant as Bitcoin has lost 30+% of its value in the past two months.

4. Today's Deep Dive on How to Fundraise Like a Pro: the art of VC coffee chats

In my role as a startup fundraising coach (or sparring partner, as I often like to say) I come across at least a dozen new startups each week. One of the most common questions is "Jorian, what steps should I take to run the most ideal fundraise possible?"

My first question back is always "how much time do you have before you need to fundraise?"

Because if a startup needs to kick off their fundraise in one month, then they should ignore everything I say below. But if you're a founder and you have significantly more time, then listen up.

Welcome to the art of the VC coffee chat. This is a conversation with a VC that you have BEFORE you start fundraising. Unfortunately, VC coffee chats often go quite wrong and can harm you during a future fundraise if not done properly. I typically see two categories of how VC coffee chats go wrong:

  • Category 1: founders treat the VC coffee chat too much like a full-on fundraising chat

  • Category 2: founders aren't prepared to talk about vision, and don't come across as having their ducks in a row

Two categories of what can go wrong in a VC coffee chat

The first category is when founders treat their VC coffee chats too much like a full-on fundraising chat. You bring out the pitch deck and share how much you're fundraising, but the problem is you're not actually ready yet.

In this scenario, you haven't tested your message (you're just winging the chat), you haven't lined up other VC conversations, and you haven't prepared your other materials. The issue is that you're not putting your best foot forward, AND you're implicitly asking for a yes/no from the VC (even if you don't realize you are).

If the VC gives you a no, you can't really return to them later.

The second category of VC coffee chat mistakes is on the opposite end of the spectrum—not being prepared to talk about vision, and generally coming across as not having your ducks in a row.

VC coffee chats are like meeting a potential employer before you interview. In that the chat with the VC is not NOT an interview. If the VC gets a bad impression of you, it doesn't matter if you're not fundraising, because when you are they almost certainly won't want to be part of your process.

Remember that VCs are looking for billion dollar plus outcomes, so even in your coffee chat, you need to give them a sense of this potential.

How to have a great VC coffee chat

Before we get into how to have a great VC coffee chat, let's talk about what the intended outcome is. First and foremost, your goal should be to build a strong relationship with the VC. Remember that if they invest in your company down the line, you'll be (stuck) with them for 5-10+ years, so building that relationship early will help you better assess if they're a good partner.

Also, when you do kick off a fundraise process, you want to do so with dozens of VCs. If you've already had coffee chats with lots of VCs months before fundraising, then this will allow you to more easily score kickoff meetings with these VCs down the road. And there are other benefits, too, such as honing in on your messaging/vision.

(PS - yes, you CAN overdo it with VC coffee chats … some founders will do dozens of these instead of building out their product & growing sales. Remember that forgetting to do the latter two items will make fundraising much harder down the road)

So here's what you need to do for a great VC coffee chat:

  • Make sure the conversation is a two-way street. You want to share lots of detail about your background and what you're building, but this is also a great chance to learn about the VC, how they see the world, and if you can trust them.

  • Share not only what you're doing in the short-term, but also have a conversation about what your long-term vision looks like. This is a great back-and-forth discussion topic with the VC—see what they think about the space.

  • Leave a favorable impression with the VC so that you can pick things back up when kicking off a fundraising process. Or equally as important, figure out if this is a no-go area for them, so that you can confidently cross them off your list.

  • Don't disappear after a great VC coffee chat. Make sure you stay in touch and keep them regularly updated (ideally once a month) until you're fundraising, so that you stay top of mind.

VC coffee chats can be a great way to strategically improve your fundraise if you have enough time. Just make sure you do them the right way, so they actually help you.

To the VCs & founders who've made it this far in my newsletter—what's your take on what makes a great VC coffee chat?

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