choosing

7 questions to choose your VC

Author

Jorian Hoover
March 23, 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.

One exciting development on my end is I’m dipping my toes into video — in April I’ll be sharing short-form videos across TikTok, Instagram, and YouTube shorts. I have a lot of fundraising insights I’m excited to share with the world. If you have any tips or words of wisdom for me as I get started, please do let me know!

For today’s newsletter, I’ll discuss AI training gyms, review the latest fundraising rounds Tier 1 VCs led last week, share my recommended VC newsletters/podcasts, and give a deep dive on choosing which VC to take money from.

Last, 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 training gyms

  2. What funding rounds did Tier 1 VCs lead last week (Mar 14-20, 2026)

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

  4. Today’s deep dive on how to fundraise like a pro: 7 questions to choose your VC

1. Jorian’s 1min take: AI training gyms

One new category I’m tracking in the AI landscape is AI training gyms. One example of this is Deeptune, which just announced a sweet $43M in funding from Andreessen Horowitz (a16z). Just as it doesn’t make sense to rely on real planes to initially train pilots, it often doesn’t make sense for AI to train on actual software, because this is slow, expensive, and risky.

And so companies like Deeptune have created a sort of “training gym” for AI — gyms that mimic the likes of Slack and Salesforce to unlock even better AI reinforcement learning. This allows AI training to go beyond human annotation and training on stale data, and hopefully unlocks a new layer in AI model improvements.

If you have any favorite AI training gym startups you’re tracking, please share them as I’d love to learn more about the category.

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

  • Newsletter: “Your Data Agents Need Context” (link) by Jason Cui and Jennifer Li, Partners at Andreessen Horowitz (a16z). I’ve now worked with multiple founders building in the context space, and it’s a hot area of investment for VCs. Without enterprise context, many AI agents simply won’t work.

  • Newsletter: “Corporate Venture Capital: A user guide” (link) by Amias Gerety, Partner at QED Investors. Corporate Venture Capital (or CVC for short) often befuddles founders and this guide by Gerety is a strong read to better understand this type of VC (or non-VC!).

  • Newsletter: “Conference marketing for startups: How to drive real ROI on a lean budget” (link) by Mitchell Yee, Head of Events at SignalFire. Among all the startups I come across, conferences are often a key component in the marketing stack. However, many startups throw endless funds at conferences, and Mitchell Yee talks through how to avoid this.

  • Newsletter: “The 12x Bet on AI” (link) by Tomasz Tunguz, Partner at Theory Ventures. Tomasz talks through what levels of return are required by today’s incredible capex investments into AI. Although, in the LinkedIn version of the newsletter, Mustafa Neemuchwala, Partner at NEA, disagreed on the math.

4. Today's Deep Dive on How to Fundraise Like a Pro: choosing your VC

Are you just raising money and don’t care where it comes from? Or are you choosing a partner for the next 5-10+ years?

If you fall into the second camp, then buckle up because today’s newsletter is about choosing your VC.

Too often, founders end up regretting the VCs they chose to take funding from. And they wishes they had asked many of these questions before signing the term sheet or SAFE. So here are my 7 recommended questions to ask yourself before choosing a VC.

1) How much does this VC actually show up to help?

If you were looking for help from your VC, but they end up ghosting you a few months after the term sheet’s signed, then you’re out of luck. I’ve seen this happen most often with taking money from multi-stage firms (because they have bigger fish to fry) but it also happens at the earlier-stage. Do your diligence on how much the VC will actually help.

2) How good is the help when they do show up?

We all have that family member who gives us advice that goes in one ear and out the other. You don’t want a VC where you’re having to always ignore their advice. Or worse, if they start demanding or strongly requesting you to take a strategic path you don’t want to. Ask portfolio founders what they thought about the VC’s help.

3) How do they behave when things aren’t going well?

When everything is going up-and-to-the-right, usually founders and VCs tend to get along well. But even the best startups have their dark days, and you don’t want a VC that turns on founders when times are tough. VCs often have control and economic provisions that give them power, so make sure you find a founder-friendly VC.

4) What are they like to have on your cap table day-to-day?

While you want your VC to be available for help (if that’s what you’re looking for), you also don’t want a VC that is annoying you constantly. Try to get a sense of what the VCs style is — are they someone you can work well with or is it going to be a constant challenge?

5) What signal does their name send to the market?

There are thousands of exciting startups in the US, and only a small percentage of them can make it. Having backing from a Tier 1 VC can help — but you need to figure out just how much it will help YOU. In some markets, it matters a lot more than others. And it can also provide an important signal for raising your next round.

(though buyer beware — sometimes going with too strong of a VC can raise the stakes too much; and also if you’re stuck with a junior partner at a top VC, it might not be quite the help you’re looking for)

6) Do they actually understand your company and market?

It’s really hard to get good help from the VC if they can’t dream together with you on your company’s future and really understand what you’re building & the market. I’ve seen too many AI-tourist VCs invest into the space and be completely handicapped at providing advice to their portfolio company. Or even worse — they give advice that made sense in 2009, but doesn’t today.

7) Will they follow on for future rounds?

This one is simple — try to figure out what the VC’s track record is (and what they say) about following on for future rounds. There’s not necessarily a right-or-wrong answer here, but you do want to be informed.

Make a VC choice you’re proud of

Fundraising is tough, and sometimes it can feel like you only have one option to take money from. But if you’re getting a bad spidey sense from a VC ahead of signing a term sheet, really think through these questions I’ve laid out. No one is forcing you to take money from this VC, and if you think they’re going to be a bad partner to work with, then you almost certainly shouldn’t take the deal.

Too many founders are miserable with the VC they took money from for you to choose a bad option. It just isn’t worth it.

But I also know many founders who are very happy (or at least moderately happy) with their VCs. Sometimes they got lucky, but often they did the right level of due diligence through other founders before signing the term sheet.

If you have any questions or thoughts on how to choose your VC, feel free to reply — I’d love to hear what you think.

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