regroup

should you pause your fundraise?

Author

Jorian Hoover
December 15, 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.

The past week I’ve been enjoying some pastel de natas. Do you know where I’m at? Email me your guess and let me know if you have any recommendations for this beautiful city!

Today’s newsletter will cover my nerding out over an AI education product, the latest funding rounds Tier 1 VCs led last week, my recommended VC essays & podcast episodes, and a deep dive on when you should pause your fundraise & regroup.

And 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: I’ve been nerding out over an AI education product…

  2. What funding rounds did Tier 1 VCs lead last week (Dec 6-12, 2025)

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

  4. Today’s deep dive on how to fundraise like a pro: when should you pause your fundraise & regroup?

1. Jorian’s 1min take: I’ve been nerding out over an AI education product…

Over the weekend, I put together the Tier 1 VC deals from last week (Dec 6-12, 2025) and came across Oboe, an AI education product that just scored a $16M Series A from Andreessen Horowitz (a16z).

I’m a bit of an education nerd, so this struck my attention for a couple reasons:

  1. edtech has taken a huge hit in the VC space the past few years, and in 2025 it’s rare to see a Tier 1 VC like a16z making an investment in edtech

  2. ChatGPT has had a tremendous impact on education … but, I’ve been quite disappointed at many of the education-specific AI products I’ve seen out there

So, naturally I had to play around with Oboe. And it is so cool and useful.

You tell it what you want to learn … for example “introduction to v60 coffee brewing” or “introduction to reinforcement learning” … and it creates a course & accompanying series of podcasts for you. As you go through the course, it gives you real-time quizzes to test your knowledge.

And you can even share with Oboe your existing knowledge, so it knows what level to make the course.

My question: is this an anomaly or is Oboe a sign of more exciting AI education products to come?

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

  • Podcast “The $3 Trillion AI Coding Opportunity” (link) by the a16z podcast. Many of the rocket ship AI startups are in the coding space. To get a sense of just how large this opportunity could be, this a16z podcast gave a great overview of the bull case.

  • Podcast: “Do SAFE investors need to be accredited?” (link) by Jason Yeh of Adamant, interviewing Aaron Ginsburg of Fenwick. Jason is a fellow HBS grad and also helps startups with fundraising. His interview with Aaron Ginsburg helped demystify common founder questions on who can and cannot sign SAFEs.

  • Podcast “The Future of Voice AI: Agents, Dubbing, and Real-Time Translation” (link) by Sarah Guo of Conviction, interviewing Mati Staniszewski, co-founder of ElevenLabs. One of the iconic VC-backed startups of this AI era is ElevenLabs, and I thoroughly enjoyed this conversation between Mati, and renowned AI investor Sarah Guo.

  • Newsletter “Nobody “wants” AI” (link) by Rob Snyder. Rob is an expert when it comes to helping startups scale their sales, and his recent newsletter tries to break down what enables AI startups to scale to $20M ARR in record speed.

  • Newsletter “26 Predictions for 2026” (link) by Rex Woodbury of Daybreak. It’s the time of year when we get next year’s predictions, and here was one of many that I enjoyed reading. I find that going through other people’s predictions help me better tune my own perspective on the future.

4. Today's Deep Dive on How to Fundraise Like a Pro: when should you pause your fundraise and regroup?

One piece of fundraising lore you’ll hear from VC-backed founders goes something like this: “it took me 200 meetings before I secured a term sheet”

Statements like these can genuinely help founders understand how much of a grind fundraising can be.

However, I also think founders can infer the wrong takeaways from these kinds of statements. Namely:

  1. that fundraising always requires hundreds of meetings

  2. that if you just keep pushing, you’ll eventually receive funding

  3. that there’s no point at which you should pause your fundraise and regroup

Today’s essay is about statement #3 in particular.

And it’s a question I get asked A LOT by founders: “when should I pause my fundraise and regroup?”

Deciding to pause your fundraise & regroup

So, let’s assume you’ve been fundraising for a couple months. When should you decide to pause your fundraise and regroup?

My first questions to you would be:

  • “how many VC meetings have you had?”

  • “how far along in the process have you made it with VCs?”

  • and “what feedback have you heard from VCs on why they didn’t invest?”

The cases where I would regroup are two-fold:

The first scenario is if you haven’t had that many VC meetings, BUT you are getting consistent negative feedback that you know to be true and can fix. In these cases, it can be worth a quick or longer pause to fix these issues and then reboot your fundraise to come back with strength.

=> this is the “easy” scenario because there’s a relatively obvious fix that you agree with

The second scenario is where you’ve had a lot of VC meetings (let’s say 75 or more) and none of the VCs want to progress past the first or second meeting. VCs are telling you a myriad of reasons they’re not investing (not enough traction, don’t believe in the market, etc.), but you don’t agree with them. The big question is, should you pause and regroup?

=> this is the “hard” scenario … something is not working in your fundraise and you can’t quite figure out what. You know there might be a VC out there who wants to fund you, but you’re also wondering why no VC has progressed you past the second meeting.

In this case, the fact that you’ve talked with so many VCs but none have progressed past the second meeting makes me think you should likely consider other options.

For example, are there other types of capital / investors (such as angels) that could be a better fit for you? Or would changing the amount you’re raising help you get your fundraise done?

Or, do you have enough runway to return to building the product & selling? Additional traction helps to convince many investors, so this might be the path you choose if you have the ability.

At the end of the day, when you’re fundraising, you’re diverting attention from the more important parts of your startup (building & selling), so at some point it is important to return to those.

When should you NOT pause your fundraise?

On the other hand, pausing your fundraise may not be the right answer for you. Here are a couple common scenarios when you should not pause your fundraise:

  1. If you haven’t had THAT many VC meetings. If you’ve heard fewer than 40 no’s from VCs, there’s a good chance you should keep pushing (unless you’ve heard consistent negative feedback that you agree with and is fixable, as mentioned above). I can’t tell you how often founders tell me that their term sheets came from meetings #41 thru #100.

  2. If you’ve spoken with a lot of VCs and made it through to the later stages several times, but just haven’t scored a term sheet yet. In this case you’re likely getting market signal that there’s interest in your deal, but you just haven’t found the right VC. Unless you feel like you’ve met with nearly all the potential VCs who could fund your idea, then it likely makes sense to keep pushing.

Pausing your fundraise is not only a tough decision, but each case is unique. I’ve tried to highlight a few common scenarios above, but these are not rigid rules. There are exceptions all over the place … such as founders who were told their idea was crazy 199 times (never making it past a second meeting) only to finally get funded in the 200th meeting.

So my main message is: let’s not take it as biblical advice that every founder needs to push to 200 VC meetings to get funded. Sometimes it makes sense.

But sometimes it doesn’t.

Trust your gut and don’t believe everything you read on the internet (including here!).

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