Welcome to the latest edition of “Into the Ring” — my biweekly newsletter on how to successfully plan & execute on your startup fundraise. As a reminder, I’m Jorian Hoover and I’m a Startup Fundraising Sparring Partner. I guide Pre-Seed thru Series A founders through their fundraising processes (helping them to raise over $160M)—you can check out how to work with me here. And a warm welcome to the new subscribers for this edition! If you were forwarded this newsletter, you can subscribe here.

Before diving into today’s essay, I’d like to share some recent data from Peter Walker of Carta busting the myth that you can’t raise from VCs in the summer.

Carta has some of the most pristine data around venture deals in the US. For this analysis, Peter analyzed over 42K primary rounds signed by US startups on Carta. What he found is that VCs are still closing many term sheets in the summer, when they are supposedly all on yachts on the Amalfi Coast.

To me, it was a sigh of relief and also affirming to see this data. I often hear from founders “oh, I can only go out to fundraise in September/October or January thru April.” They believe that if you fundraise outside of these windows, then you’ll run into a brick wall. Now, would I recommend KICKING OFF your fundraise in the middle of August or right before Christmas? Probably not.

But, I think founders have X’d off too many months for potential fundraising kickoffs. For example, a founder asked me “Can I really fundraise in June? In just two months all VCs will be out of office and we’ll lose momentum.” Maybe in a future newsletter I’ll expand more on this topic, but for now I’ll leave it at this: go out to fundraise when YOU’RE ready, not when everyone else has told you is the optimal time.

Thank you as always to Peter for the terrific data & insights, and if you’re not following him yet on LinkedIn, you’re seriously missing out.

…Now on to today’s newsletter topic, which is about the importance of playing offense when it comes to skeletons in your closet during fundraising.

Skeletons in the Closet: Why VCs Care and How to Handle Them

Every VC has asked the question: “Who’s that on the cap table?” Or: “What happened with your co-founder?” Or: "Why is there a contractor listed as owning IP rights?"

It’s not the skeleton that (necessarily) kills the deal. It’s how you handle it.

Startups are messy. Investors know that. But the way you navigate uncomfortable topics—especially during fundraising—says a lot about your leadership, maturity, and trustworthiness. When you play defense and hope no one asks, you risk looking evasive. When you play offense and take control of the story, you come off as thoughtful and trustworthy.

Here’s how to do it right.

Common Fundraising Skeletons

Founders often assume they’re the only ones with mess in their history. Not true. Here are some of the most common skeletons that show up during fundraising:

• Acrimonious co-founder departures (especially if they still own equity)

• IP ownership gaps (e.g. early code written by someone without a signed agreement)

• Dead equity on the cap table (non-active advisors or team members with sizable stakes)

• Unfiled board consents or missed legal paperwork

• Past lawsuits or investor disputes

These things don’t have to be fatal. In fact, they’re often manageable. But they do need to be handled with thoughtfulness.

The Danger of Silence

When founders decide to hide skeletons, they’re usually hoping to sidestep awkward conversations. The problem? VCs will find out.

Whether it’s in the data room, through cap table analysis, or casual reference checks, these issues eventually surface. And when they do, the VC is left wondering:

• When were they going to tell me about this?

• Are there other red flags I haven’t seen yet?

• Can I trust this founder to be transparent moving forward?

In venture, trust is everything. VCs are deciding whether to enter a 5-10+ year relationship with you. If they sense you’re hiding something, the deal can fall apart quickly.

The Offense Strategy

The better move? Play offense. Address red flags proactively—on your terms.

Here’s how:

1. Acknowledge Early

Don’t wait for the VC to discover the issue. Raise it in a follow-up email, a data room note, or even the meeting itself. Example:

2. Show the Lessons Learned

Founders who own their mistakes (or early messiness) and show how they’ve grown from it earn more trust. Frame the story with reflection:

3. Present Your Mitigation Plan

VCs want to see what you’ve done (or are doing) about the issue. This could mean:

• A vesting schedule adjustment

• A clean-up clause in the next financing

• A definitive agreement with a former employee

• And so on

Whatever it is, show you’re not just aware of the issue, but that you’re also on top of it.

Final Thought

No startup is perfect. Investors know this.

But there’s a big difference between a messy past and a messy founder. The former can be explained. The latter raises doubts.

So if you have a skeleton in your fundraising closet, don’t wait for someone to find it. Own it. Explain it. Show what you’ve done to fix it.

Because at the end of the day, skeletons don’t (necessarily) kill deals.

Surprises do.

👉Want a sparring partner to help you navigate your skeletons while fundraising? I would love to help.

Thanks for stepping Into the Ring 🙏

Thank you for reading today, and for your support. If there’s anything that resonated with you, simply hit reply and let me know.

📩 If you were forwarded this newsletter, you can subscribe here.

👉 I’ve helped 40+ founders raise over $160M. Curious to work with me? You can learn more about what that looks like on my website.

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