simplicity

build a k.i.s.s. fundraising story

Author

Jorian Hoover
January 06, 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.

I hope everyone reading this had a wonderful holiday season and is feeling energized heading into 2026. I’m excited to be back and bring Into the Ring to you every week in 2026 (please forgive last week’s holiday absence!).

For today’s newsletter, I’ll give my quick take on the startup scene in San Francisco, review the latest fundraising rounds Tier 1 VCs led last week, share my recommended VC essays & podcast episodes, and give a deep dive on the importance of simplicity when fundraising.

And thank you for being part of this Into the Ring tribe of 1.7K+ 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: San Francisco

  2. What funding rounds did Tier 1 VCs lead last week (Dec 20, 2025 thru Jan 2, 2026)

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

  4. Today’s deep dive on how to fundraise like a pro: simplicity when fundraising

1. Jorian’s 1min take: San Francisco

SF is back, and it never really went anywhere.

Especially during covid, we heard lots of discourse on how Austin, Miami, etc. would replace San Francisco as the preeminent cities to build tech companies in.

Even during this period, I thought this was silly. The Bay Area was largely dwarfing these other cities by 10x or more in terms of capital raised. And so many of these proclamations about Austin and Miami were based more on anecdote than on fact.

And now with AI, momentum is back on SF’s side and it’s cementing its #1 spot. Anthropic & OpenAI are based there, AI startups & talent are centered around SF, people are moving back to the city, rents are rising, there’s excitement around the mayor, and so on.

Speaking of anecdotes, here’s one that surprised me: multiple non-SF accelerators that I’ve met (even ones based abroad) are now asking their founders to move to San Francisco.

Because the thing about SF is — yes, you get some benefit if you fly out there and raise in SF. But unless you’re actually building in SF, VCs won’t see you as an SF-based startup (and therefore give you the SF premium).

So do you need to move to SF? No. Iconic startups are still getting build outside of SF.

But all things being equal: building an AI startup in SF will likely get you higher amounts raised and higher valuations than building outside of the Bay Area.

What do you think?

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

  • Podcast: “#840: Bill Gurley — Investing in The AI Era, 10 Days in China, etc.” (link) by Tim Ferriss, interviewing Bill Gurley (former GP at Benchmark). Tim Ferriss is one of the best question askers I know, and I love how plainly Bill Gurley speaks about the AI era we’re living in. For example — to the critics who say circular AI deals are relatively small, Gurley asks, “well why are they happening at all then?”

  • Newsletter: “Notebook Lawyer” (link) by Fred Wilson, GP at Union Square Ventures (USV). Wilson talked about “an experiment [he ran] over the holidays” to have NotebookLM from Google ingest a ton of closing documents from previous investments USV has led. And then had NotebookLM do an extensive legal review of the draft documents and create a memo to raise potential issues. He saved tens of thousands of dollars in legal fees…

  • Newsletter: “Push, Pull, and PULL” (link) by Rob Snyder, who’s a startup sales coach & expert. When startups are struggling to figure out their go to market (GTM) motion, I often suggest they check out Rob’s content (and potentially work with him). He has an in-depth pull framework around how companies actually buy from startups which goes against a lot of what we’re taught in business school & business books.

4. Today's Deep Dive on How to Fundraise Like a Pro: simplicity when fundraising

You’re a founder and you’re meeting a VC. You want to score a $2M pre-seed for your startup.

This startup is your baby, the culmination of a decade you’ve spent in the industry. And so you have a lot of ideas for it. You want to attack a huge market with some big incumbents. But you also see several spinoffs of your idea and want to build adjacent products.

You also see some consulting companies in your space and think you could do a better job than them. And so you want to tell the VC about your services offering. Most of all, you just want to share all these ideas with the VC and for them to get giddy about all the opportunity. And that you’re the right person to build this.

Meanwhile, the VC on the other side of you is meeting a dozen new founders this week, and around 50 this month. They’re also on several boards and keeping track of 20+ portfolio companies.

Yes, the VC wants to dig deep into your company. But they want a simple way to get to an “aha”.

Far too often, founders will completely overwhelm VCs with info.

At best, this makes it hard for the VC to get to that “aha moment” with your company.

But at worst, VCs might see you as an unorganized founder who’s not ready to build a startup. They might think that you’ll spend that $2M all over the place without any direction in mind.

Use the K.I.S.S. principle for your startup’s story

The US Navy came up with a design principle named “Keep it simple, stupid” or K.I.S.S. back in 1960. And it’s a principle that’s helpful across industries, whether it’s Johan Cruyff playing soccer or Steve Jobs designing the iPhone.

Startup fundraising is no different. Your story is the most important thing, and keeping it simple is an invitation for others to understand what you’re building and your vision.

How do you build a simple story? What I recommend to founders is to think through the “aha moments” that an investor needs to have to really “get” your idea.

Perhaps, they really need to understand your problem. It’s non-obvious, and once they understand it, they can have an “aha moment” that you’re the right startup to build the solution.

Or maybe the problem is dead obvious, but the “aha moment” is how special your team is. And that they’d be silly not to invest in you.

Most likely, it’s a combination of multiple “aha moments.”

In a well-crafted, simple story for your fundraise, you want to get the VC (or whoever’s listening) to these “aha moments” as quickly as possible. Write them down and focus on getting to those points — and helping them understand what they need to believe in order to invest.

Spend time there and don’t spend much time elsewhere.

“So should I ignore other areas of my startup?”

Often in creating a simple story, you end up leaving out real-world complexity. I’m not suggesting you ignore that complexity, but rather that you approach sharing that complexity differently.

The art of a startup story is getting a VC to those “aha moments” where you have PERMISSION to completely nerd out about a topic. For example, if a VC has gotten the “aha” of your high-level customer flow, and then asks you to go into detail about the tech behind it, that’s a perfect time to nerd out about your tech.

What you don’t want to do is start nerding out about your tech (or insert other subject) before the investor has gotten that high level concept.

One word of caution: don’t feel the need to start nerding out about every topic possible (btw: I use “nerding out” as shorthand for going into lots of detail about a subject). In fact, if you start giving too many details on too many topics, you can run the risk of seeming unorganized to the investor or like you have no overarching plan. If this starts to happen (and often it’s the VC who leads you astray), feel free to bring the conversation back to the primary points that matter.

Even when I speak with founders who are raising $50M+ rounds, they tell me that getting your story right is the most important thing when fundraising.

And a final message from me?

Keep it simple, stupid.

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I’ve helped 50+ founders run high-quality fundraises and raise over $190M. Check out jorianhoover.com to read founder testimonials and learn more about my approach.