questions

level the playing field with VCs?

Author

Jorian Hoover
December 23, 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.

Although it’s the holiday season, many VCs & founders are telling me their calendars are still relatively full with fundraising meetings. Speaking of the holidays, I want to wish you a Merry Christmas & Happy New Year. No matter what you celebrate, I hope you get to spend some quality time with friends & family over the coming week (and hopefully not have too many meetings!).

For today’s newsletter, I’ll give my quick take on the issues with inbound interest from VCs, review the latest fundraising rounds Tier 1 VCs led last week, share my recommended VC essays & podcast episodes, and give a deep dive on the importance of asking VCs questions.

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: the problem with VC inbound

  2. What funding rounds did Tier 1 VCs lead last week (Dec 13-19, 2025)

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

  4. Today’s deep dive on how to fundraise like a pro: why you should ask VCs questions

1. Jorian’s 1min take: the problem with VC inbound

Y Combinator (YC) demo day was a few weeks ago and with that came hundreds of YC startups entering the fundraising market. One of the pieces of advice YC startups are often given is to rely on inbound interest in their fundraise.

The setup at YC is perfect for inbound — hundreds, if not thousands, of investors have their eyes on YC demo day and these startups are a hot commodity. Almost every YC startup receives dozens of inbound investor inquiries; some even receive hundreds.

But one of the problems I see again and again with YC (and also non-YC) startups is that relying on inbound can be a bit of a curse. On the one hand, if you get enough inbound interest, then you can run a strong fundraise process amongst just the VCs who've reached out to you. However, what if you don't get enough inbound interest to result in a VC leading your round?

…well, you can get a bit screwed.

You see, by relying solely on inbound interest you're leaving aside hundreds of VCs who could be interested in leading your round. And what if the VCs you'd want to partner with most don't happen to be the ones sending you inbound interest?

So while inbound interest is great, it shouldn't be your sole source of VC conversations when fundraising. You should also cultivate a well-researched list of VCs that you admire and that you want to get warm intros to.

By combining inbound interest with your own VC list, you can better control your fundraising process and ensure you're speaking with enough VCs to have a high likelihood of getting a term sheet.

Otherwise, you're just leaving your fundraise process up to luck.

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

  • Newsletter: “The End of Interchange” (link) by Fred Wilson, GP at Union Square Ventures (USV). Fred is one of the pre-eminent early-stage investors in the US and he recently shared USV’s thesis that lots of startup opportunity will be created if interchange fees come to an end.

  • Newsletter: “State of Consumer AI 2025” (link) by Olivia Moore and Justin Moore of a16z. Andreessen Horowitz (a16z) has been at the forefront of consumer investments in past years, and I’d recommend their breakdown of what happened in Consumer AI in 2025.

  • Newsletter: “5 GTM Shifts We Saw Founders Get Right in 2025” (link) by Mandy Cole, Partner at Stage 2 Capital. Stage 2 is a GTM-focused VC firm, and so they have one of the best perspectives on the latest and greatest in GTM for startups.

  • Podcast: “The 2026 AI Forecast” (link) by Sarah Guo (GP at Conviction) and Elad Gil (prolific solo GP). Rounding up what’s mostly a set of essays & podcasts focused on the new year transition, you have to check out Elad & Sarah jam on where they see AI progressing in 2026. Both are among the most respected AI investors currently.

4. Today's Deep Dive on How to Fundraise Like a Pro: why you should ask VCs questions

Successfully raising venture capital can feel damn near impossible.

Even the best founders typically receive "no’s" from VCs far more often than they receive a "yes."

And because the odds are stacked against you, this can lead to bad tendencies in calls with VCs. In particular: not asking VCs any questions.

Let's step inside the shoes of a venture capitalist to understand why this is a problem.

You as a VC might meet with 15 new founders in any given week. In these meetings, you are looking for a startup that's got the right stuff, sure, but you are also looking for a leader that has potential.

And imagine there's a founder who has great answers to all of your questions, but he or she has no questions for you.

You might think: "this founder is asking us for $4M, but has no questions for us? They don't want to know what kind of partner we'll be in the business?" … and you might even wonder, "maybe they're desperate, and don't really have any other VCs who are interested"

Of course, these are cognitive biases on the VC’s part, but these biases are very real.

Create a more level-playing field with a VC by asking them questions

It can be really tempting to be deferential to a VC, but be careful. Not only does this lead to cognitive biases for the VC, decreasing the chances you'll get a term sheet, but it also makes your life harder in assessing if you want to take the VC's money.

One simple way you can make great strides in this realm is by asking a VC questions when you meet them.

However, there's a right and a wrong way to ask questions to a VC.

Every month I listen to dozens of founder meetings with VCs, and here's the common mistake I see:

  • Founders will spend 90% of the call pitching & answering questions, and then in the final 10% they jam in a couple questions to the VC

  • Not only does this lead to almost no questions being asked to the VC, but the questions themselves don't give much information

  • Usually, founders will ask questions like: "what's your typical check size?", "what investments have you made recently?", "how do you help founders?", etc.

The problem here is that the answers to these questions are either easily google-able or are such softball questions that they don’t give the founder new information. And the VC doesn't feel like they're being tested.

Asking the right questions to VCs

So, what are the right questions to ask venture capitalists? To answer this, let's take a step back and think through what an ideal founder / VC meeting looks like.

In an ideal world, a founder's meeting with a VC goes something like this:

  1. The founder and the VC dream together about what the future of the startup could look like

  2. The founder leaves the conversation with increasing excitement that they want to partner with this VC

  3. The VC leaves the conversation with more conviction that they want to bet on this founder

  4. There are clear next steps on how the deal moves forward for the founder and VC

The questions I believe work best influence points #1, 2, and 4.

On point 1, one good category of questions to ask is about the startup you're building. For example, asking how the VC thinks about the space, how they see the competitive dynamics playing out, and what routes they see for you becoming a billion-dollar-plus outcome.

On point 2, think through what info will actually help you decide if this is the right VC for you (i.e. don’t ask softball questions or stuff that’s easily available online). For example, maybe you want to ask about specific examples of how they’ve helped portfolio companies or dig into their reserve strategy.

On point 4, you want to get clarity on what their process as a VC firm is, and also share how that aligns with your timeline. It’s helpful to ask the right questions so you leave the call with clear next steps so you can march towards a term sheet.

The above examples are just the tip of the iceberg. If you take money from a lead VC, and your startup does well, you’ll likely be working together for 5-10 years, if not longer. You wouldn’t want to enter into a partnership like that without asking a number of questions, right?

Plus the VC will appreciate that you’re doing your homework, and will receive the (real) impression that you’re a more in-demand founder who cares about who they take money from.

to the 1K+ founders and VCs subscribed to this newsletter — what are some of your favorite & most helpful questions founders can ask in calls with VCs?

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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.