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.

I just returned from a month-long tour across the US, which was incredibly energizing. Getting to work with clients in-person and reconnect with friends and family reminded me why I love this work. Speaking of clients, congrats to two founders I worked with who successfully closed their rounds in July (though they haven't shared the news publicly yet).

On the market front, I was encouraged to see Peter Walker's LinkedIn post this week about how down rounds are starting to fade. Though as Peter noted, he's a bit concerned we might face a new down round wave in 2027-2028 given all the inflated AI valuations we're seeing today. Something to keep an eye on as we navigate the current fundraising environment.

Now on to today’s newsletter topic, which is all about why you’re likely thinking about VC follow-ups backwards.

The Follow-Up Fallacy: Why Not Following Up Is the Real Desperate Move

A founder I worked with had been ghosted by a promising VC for 2 weeks. Radio silence after a great first meeting and two initial back-and-forths over email. She was paralyzed by fear of seeming "pushy" and almost wrote them off completely. Then I coached her to send one thoughtful follow-up with business updates and fundraising momentum. 3 weeks later: term sheet.

Here's what that founder got catastrophically wrong.

Everything You Think You Know About VC Follow-ups Is Backwards

The conventional wisdom around VC follow-ups is broken. Founders think following up makes them look desperate. They worry about being pushy. So they sit in silence, hoping their brilliant pitch was memorable enough to cut through the noise of 50 other deals.

Here's the reality: NOT following up is actually the desperate move.

Think about it. You're essentially saying, "I hope this investor remembers me among the dozens of pitches they see each month, and I'm too scared to remind them I exist." That's not respect for their time. That's fear disguised as politeness.

I've worked with over 40 founders who've raised more than $160M combined. The pattern is clear: the founders who treat follow-ups like professional sales communication close faster and get better terms. The ones who stay quiet? They struggle.

VCs expect follow-ups. They're managing massive deal flow, juggling portfolio fires, and making million-dollar decisions daily. A well-crafted follow-up isn't an interruption. It's helpful information that makes their job easier.

The most successful founders I work with have cracked this code. They've realized that confident founders follow up systematically, while insecure ones hide behind silence.

The Professional Follow-up Framework

Here's how to transform your follow-ups from awkward check-ins into competitive advantages:

Reframe Your Mental Model Stop thinking "I'll look weak or desperate if I follow up." Start thinking "I'm providing valuable information they need to make their decision." Every enterprise salesperson knows that deals die in silence. Your fundraise is no different.

Use the Value-Add Formula Avoid sending a "just checking in" email. Your follow-ups should contain substantive updates in one of three categories:

Business progress: "We just signed our largest enterprise customer. A $50K annual contract that validates our pricing model."

Fundraising momentum: "Two VCs have advanced us to partner meetings this week, and we're expecting term sheets by month-end."

External validation: "Saastr founder Jason Lemkin tweeted about our product launch, calling it 'exactly what the market needs right now.'"

Time your Follow-Ups Wait 1-2 weeks since you last heard from the VC (unless they missed a specific deadline, in which case you can follow up 2-3 days after that deadline passes). Space out your 2 follow-ups by at least 1 week.

One founder I coached got radio silence from a top-tier VC for two weeks. She sent one update mentioning two new VCs showing strong interest plus a product milestone. The VC's response? "Sorry, had two portfolio emergencies. We've been discussing you internally and want to continue." Term sheet arrived three weeks later.

Master the Professional Close End every follow-up with a direct but respectful ask: "Given the momentum in our round, we're hoping to hear back by Friday. Are you still interested in moving forward, or should we focus our energy elsewhere?"

This isn't pushy. It's professional. You're giving them an easy exit while demonstrating you have other options.

The Follow-up Advantage

That founder from the beginning? The one follow-up she almost didn't send turned into her lead investor. Without it, she would have written off one of the best VCs in her space.

The difference wasn't luck. It was mindset.

In fundraising, the founders who win aren't the ones who wait politely in silence. They're the ones who systematically remind VCs why they matter while VCs are drowning in deal flow and portfolio crises.

Your next term sheet might be one follow-up away. The question isn't whether you should follow up—it's whether you can afford not to.

👉Want a sparring partner to help you navigate investor follow-ups? 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.

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👉 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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