thorny

what questions will VCs ask you?

Author

Jorian Hoover
February 03, 2026

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.

(PS - my mom asked me yesterday — “hey, you’ve been saying this $190M number for a while, has it increased?” to which I said, “yes, multiple founders I’ve worked with have raised since then, but I’m too lazy to update these numbers in 9 different places.”

…alas, at least my mom is reading this newsletter — hi mom!)

Great to have you here and I’m looking forward to my SF trip later week + getting to meet the VCs & founders who reached out!

For today’s newsletter, I’ll give my quick take on AI mega round concentration, review the latest fundraising rounds Tier 1 VCs led last week, share my recommended VC essays & podcast episodes, and give a deep dive on what questions VCs will ask you.

And thank you for being part of this Into the Ring tribe of 1.8K+ 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: AI mega round concentration

  2. What funding rounds did Tier 1 VCs lead last week (Jan 24-30, 2026)

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

  4. Today’s deep dive on how to fundraise like a pro: what questions will VCs ask you?

1. Jorian’s 1min take: AI mega round concentration

One takeaway from compiling each week’s Tier 1 VC deals is just how many mega deals ($30-50M at the early stage, $50-500M+ at the later stages) are happening in AI.

But one revelation is that so many of these deals are concentrated in just a few areas — such as AI for legal and AI for customer support.

This makes me wonder: what will the winners in this space look like 5-15 years from now? Will we see a: (1) winner-takes-all endgame, (2) a few big winners, or (3) a dozen+ winners?

I’m beginning to wonder if we might end up in scenario (3) for areas like legal and maybe even for customer support. As AI companies start to build in areas traditionally dominated by services companies (for example, legal firms and consultancies), the end states may mimic the current market dynamics.

Because in the services space, there is so much customization for each customer and lots of different workflows. In the law firm space, for example, you have tons of winners —dozens of large law firms who are quite successful and have different specializations.

If the underlying AI technology becomes (relatively) commoditized, I could see dozens of AI company winners (and many VC firms who do well on these mega rounds), as value would accrue to the specialization for each customer. But if one AI legal firm ends up with a superior technology to all the rest, perhaps we end up in a winner-take-all market and many of these VC mega rounds end up going to $0.

What do you think? I’m still working on this hypothesis so am very curious what your two cents are on how you see AI in legal and customer support playing out in terms of market dynamics.

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

  • Newsletter: “Leaders, gainers and unexpected winners in the Enterprise AI arms race” (link) by Sarah Wang, Justin Kahl, and Shangda Xu of Andreessen Horowitz (a16z). The a16z team commissioned IT surveys on the usage of OpenAI, Anthropic, and Google AI in the enterprise and found that while OpenAI remains dominant, the latter two are growing quite rapidly in the enterprise.

  • Newsletter: “Reality Doesn’t Negotiate” (link) by Mike Maples, General Partner at Floodgate. Anytime Maples writes something, I immediately want to read it as he’s one of the most prolific seed investors of the past two decades. He theorizes that just because you were right in the past, doesn’t mean your business is certain to make it in the future.

  • Newsletter: “The Fundability Trap” (link) by the team at Euclid Ventures. I appreciated this overview of how VCs may all be chasing the same “fundability”-ness across startups, which can lead to reversion to the mean. One thing that’s uncertain? Is AI really presenting such a huge opportunity for a high-enough % of these mega rounds to work out?

  • Podcast (and also newsletter): “TSMC Risk” (link) by Ben Thompson of Stratechery. This past week, Microsoft stock took a massive beating, dropping 10+% due to lower-than-expected AI/cloud growth. Thompson shares that tech companies are hamstrung by supply (i.e. not enough chips), and with TSMC committing to relatively conservative capex numbers, big AI & tech companies could be losing billions in potential revenue over the coming years.

4. Today's Deep Dive on How to Fundraise Like a Pro: what questions will VCs ask you?

One of my core theories about prepping for VC conversations is that founders should spend a lot more time preparing for questions from VCs.

If you get a term sheet from a VC, you’ll almost certainly have 3-5+ meetings (and more at the later stage) with that VC before you receive terms.

So at minimum, you’re spending a few hours with the VC. If you were to divide up all these minutes between delivering your pitch & answering questions, what would the percentage breakdown be?

That’s right. Answering questions from the VCs (and asking them your questions) would take up 90+% of the airspace.

Don’t overlook prepping for VC questions

A common scenario I hear about from founders is that they spent a couple dozen hours perfecting their pitch deck & delivery, but then once the VC asked the first zinger of a question, they were knocked back into reality.

The problem is that a pitch is just your talk track of your story that puts you in the best light. It might hit the core points (and cover some of the primary weaknesses), but it can’t answer every question a VC might have. So you need to prepare for these questions.

However, preparing for VC questions is not easy.

In fact, one of the primary challenges is understanding what questions will VCs even ask? It’s one of the reasons why I recommend doing 5 practice conversations with VCs before you kick off with dozens of VC conversations.

But before you even have those practice conversations, there are steps you can take to prepare for potential VC questions.

Building a list of potential VC questions

There are two types of VC questions I recommend preparing for:

  1. run-of-the-mill questions that VCs might ask you

  2. the thorniest questions that VCs can ask you

It’s a mistake to not prepare for both type 1 and 2 questions.

To build a list of potential questions, I recommend pulling up your pitch deck and going slide-by-slide. For each slide, I want you to brainstorm & jot down all the potential questions a VC could ask about that topic. And to gather even more potential questions, you can do this exercise with a colleague or a friend who’s a VC.

Write down these questions in a google sheet — you’ll likely have dozens of questions spread across areas such as your problem space, how your product works, go-to-market, and so on.

This will give you many Type 1 questions. You might have even unsurfaced some Type 2 questions.

To try and get the remaining Type 2 questions, you want to ask yourself, “what questions do I not want to be asked by VCs?”, “which questions will be hardest for me to answer?”, and “what are the biggest reasons a VC might say ‘no’ to me?” You can supplant your Type 2 question bank by asking others what they see as the biggest risk areas.

How to prepare for the questions VCs will ask

Once you have your list of questions, now the exciting part begins. You’ll get to write up what your main talking points are to each of these questions. Through this process you’ll figure out where your strengths and weaknesses are.

For the questions where you think you have a weak answer, ask yourself if there’s a better answer that could assuage investors, or if it’s a true weakness of the business/fundraise.

If it’s the former, then go find that better answer. But if it’s the latter and it’s a true weakness, this isn’t something you want to necessarily fix (as every startup will have its issues, and VCs should invest despite your weaknesses).

However, with a true weakness, you can decide if you want to play offense or defense on the issue. And this is quite an important distinction. If this weakness will be an elephant-in-the-room (for example, every VC who encounters you will likely have the notion that your market is too small), then you want to play offense on this weakness and bring it up proactively. Otherwise, VCs could have these weaknesses swirling around in their head while speaking with you.

If the weakness is not an elephant-in-the-room type issue, then you likely want to play defense on it — i.e. address it only when a VC brings it up. The reason defense can work better is because you don’t want to share a ton of additional worries with a VC if it wasn’t something they were already thinking about.

Okay, now let’s get back to tactics and how to get game-ready for answering Type 1 & 2 questions.

Beyond just writing out how you want to approach your answers, it can also be helpful to have practice sessions with a cofounder or mentor (or fundraising coach!) to practice answering these questions. Increasingly, I’m spending more time with founders battle-testing them on questions VCs might ask so they can be ready for VCs grilling them.

If you’re a founder, make sure you get game-ready for questions VCs might ask you. Otherwise you’ll have a great 8 minute pitch, but then get scared once VCs start asking you tough questions.

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