Our mission with 404 Fund I

I left my job to build 404 Fund. Here’s why.

In five years, I might look back on this newsletter (if it even qualifies as one) as either the start of the best or worst decision of my life. I left an extremely reputable and well-paying job to build a venture fund from scratch. No fallback plan. No sabbatical. Just an unpopular view of where the industry is and a stubborn belief that it can be better.

Why 404Fund?

I’m building 404Fund to back the fintech founders the rest of the market either misunderstands, ignores, or just flat-out misses. Hence the name: 404.

Some of the most technical, deeply impactful fintech companies are being overlooked. Not because they’re bad companies, but because they’re complex. Because they don’t compress well into five-minute partner meetings. Because the founders are actually building infrastructure instead of talking about AI or whatever the hot theme is during demo day.

My Experience

I’ve seen this up close. I’ve been inside hedge funds and fintech startups. I’ve shipped code that moves real money. I’ve sat in investment committees and done diligence on 200+ startups. I’ve seen what separates the teams that win from the ones that quietly burn out.

Here’s what I’ve learned: The best fintech companies are weird at the start. They’re wedge-first. Distribution is hard. The tech is opinionated. The compliance stack looks like a headache. And most VCs don’t want to touch it until someone else does. Which means, usually, no one does.

But these are the companies that end up quietly owning the rails. And those are the companies I want to back. That’s why I’m building 404Fund.

What We Offer

• Investments: Writing checks between $50K and $500K, from pre-seed through seed, focused entirely on the US and Canada.

• Support: I might not be the biggest check (at least for now), but I’m okay being the one who actually shows up and sets up twelve investor meetings before the “big guys” reply to your email.

• Expertise: I bring engineering, market structure, regulatory nuance, real quant literacy, and an obsessive curiosity for how financial systems are evolving.

I’m not a tourist. I’ve tried building ten startups. Eight failed horribly. The ninth and tenth finally worked. Then came a few exits. So I truly understand what it means to be a founder who started with nothing but a bold idea.

I studied this stuff when I was broke and eating ramen. Now, even with some success behind me, I still study the industry like I did when I first started. Sure, I attend more meetings than I read now, but that’s besides the point.

Our Team and Tools

Fortunately, I’m not doing this alone. My team consists of builders, operators, and investors who’ve sat on both sides of the table, launching companies, scaling products, and managing multi billions in assets. We bring deep technical expertise, sharp commercial instincts, and hands-on support to every founder we back.

We also built our own tooling. A system called RTS, Real Trend Score, that parses signal from noise by combining behavioral product metrics with real-time sentiment scraping. DAU to MAU, session length, retention, Reddit buzz, founder velocity, and more. Not because I think software makes better decisions than people, but because if you want to spot early momentum, you need to know where to look and how to look fast to actually make it out alive in this crazy space. That’s how we avoid the trap most VCs fall into of chasing what’s popular instead of spotting what’s working.

Why Now?

I’ve been watching the market reset. All the crazy valuations have corrected. The tide is out. This is the best time in a decade to back technical founders in fintech.

My Commitment

I’m not pretending to have it all figured out. This is my first fund. I’m operating lean. I’m placing high-conviction bets. And I’m committing two things to every founder I back:

• I won’t waste your time.

• I won’t disappear when things get hard.

What’s Next?

These newsletters are going to stay honest. Some will break down deals I’m seeing. Some will dissect real companies, anonymized if needed. Some will explore founder-market fit in fintech. And some will just be reflections from someone who bet their career on this.

If you’re building something in fintech that feels a little early, a little complex, a little contrarian, I want to hear from you. 

If you’re just following along to see how this all plays out, I respect that too. Let’s see where this goes.

—

Shav

Founder, 404 Fund
www.404.investments
shav@404.investments