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.

Quick shoutout: crossing my fingers for all the readers who applied to YC's Fall 2025 batch and are waiting to hear back. The anticipation is brutal, but you've got this. And huge congrats to those of you who already got in!

On a personal note, I've been spending some time in Amsterdam lately, where I was born. There's something magical about navigating the city by bike. It makes everything so much easier and more enjoyable when visiting. Sometimes the simplest solutions are the most effective.

Speaking of effective solutions, today's newsletter is about a topic that's been on my mind: why using AI to write your fundraising materials can backfire spectacularly, and how to leverage it without losing your authentic founder voice.

When AI Makes Your Fundraising Materials Look Generic

A Bay Area founder received 65 potential warm introductions to VCs from fellow founders. Exactly the kind of network every founder dreams of. But only 11 converted to actual meetings. The memo had all the right facts about their startup, but VCs couldn't connect with the founder or the story. The culprit? They let ChatGPT write their entire investment memo, complete with em dashes flying everywhere and robotic language that stripped away their humanity.

This founder learned the hard way that in venture capital, being smart about AI means knowing when NOT to use it.

What VCs Are Looking For in Materials

Here's the reality: VCs bet on founders, not just business models. When you let ChatGPT tell your story, you think you're being efficient. What you're actually doing is handing over the one thing that makes investors want to write checks: your authentic voice and unique perspective.

I've seen this pattern repeatedly with the founders I work with. They come to me with polished, AI-generated materials that check every box but somehow feel hollow. VCs have told me they scan the first few sections of a memo and immediately decide whether to keep reading. They're looking to answer why this startup & team are special (and could lead to a big outcome). When they see phrases like 'revolutionizing the industry' or 'significant market opportunity,' they mentally check out. When your memo reads like it could have been written about any startup in your space, you've lost before the meeting even happens.

The founder I mentioned? When VCs finally met them in person, they were blown away by their passion and insights. But by then, 83% had already said no to meeting. That's the hidden cost of outsourcing your voice. You lose the opportunity to make that crucial first impression.

Understanding the psychology is crucial, but you need a smarter approach to leverage AI without losing your authenticity.

How to Actually Write Memos with AI

You don't need to throw AI out completely. You just need to know when to use it and when to stay human. Here's how to get the efficiency without losing your voice.

Let AI Gather Your Data

Use ChatGPT to gather and organize background data, but you provide the insights. Prompt it: "Create a table of the top 10 companies in [space], including: founding year, total funding, last round size, key investors, and current headcount." Use this to build your competitive slide, then add YOUR unique perspective on why you're different. Have it pull industry reports and synthesize market size data, but you write the "why now" narrative based on your firsthand experience.

Build Your Structure with AI

Let AI create structure, but you fill the content. Ask ChatGPT: "Create an outline for a Series A memo for a B2B SaaS company." Use this skeleton, then populate each section with your voice. Have it generate 50 potential VC questions for your space, then craft answers that only you could give based on your unique background and insights.

Write Your First Draft Yourself

Here's where most founders go wrong: they let AI write the first draft. Don't. With your research and outline in hand, sit down and write your first draft yourself. Use your unique insights, personal anecdotes, and specific customer conversations. Reference the market data ChatGPT gathered, but tell the story only you can tell about why this matters and why you're uniquely positioned to win.

Polish with AI Feedback

Once your authentic draft is complete, it's time to pressure-test your work. Feed your draft back to ChatGPT with prompts like: "Find logical inconsistencies in this argument" or "What questions would a skeptical VC ask about this market analysis?" Use it to spot typos, grammar issues, and weak reasoning. Think of this as having an AI editor who helps refine your thinking without changing your voice.

The Bottom Line

AI can accelerate your fundraising process, but only if you use it right. Let it handle the research legwork and structural scaffolding. Let it pressure-test your logic and catch your typos. But when it comes to telling your story, that's all you.

Your unique insights about the market. Your passion for solving this specific problem. Your perspective on why now is the moment. These are the elements that make VCs lean in and want to write checks. No algorithm can replicate the conviction that comes from a founder who's lived their story.

This week, try the four-step process on one portion of your fundraising materials. Use AI to gather data and build structure, then write the story yourself. Your authentic voice is your competitive advantage.

Because the smartest founders know when to be human.

👉Want a sparring partner to help craft fundraising materials that sound like you? 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.

➡️ I regularly share insights from my work on LinkedIn. Be sure to connect with me.