How I Raised Money From One Of The Most Famous Angel Investors of All Time
Fundraising is rigged— here's how I beat it
Here’s the truth.
Fundraising is rigged.
If you didn’t go to Stanford or an Ivy League college, most investors simply don’t believe in you.
They’ll say they do. They’ll say they “back misfits.” But when you look at their portfolio it’s the same old story. Harvard graduate, MIT graduate, etc.
Here’s the brutal truth: VCs and investors love to use Ivy League degrees as an IQ filter.
The typical founder? Attends a Tier 1 university decides to partner up with their roommate to “build a startup”…
And builds nothing. No product, no customers. Not even a clear idea.
Yet, gets into a program like YC and gets a massive “pre-seed” investment of $500k-$2M.
Product? Idea? That comes after the money hits their bank account.
That’s wasn’t me. That’s not most founders, especially if you’re reading this.
I was the odd kid in school blasting Kanye, skipping class to hit the museum, and flipping electronics online.
I never graduated college. Never worked at Google (or for anyone for that matter).
Still, I raised money from Jason Calacanis, one of the most prominent angel investors of all time (3rd/4th investor in Uber and one of the first investors in Robinhood).
Without any degree. Without any network. Without any co-founders.
Here is how I did it.
🛠️ Step 1: Build a Beautiful Product
Stop talking. Ship something real.
Your product must be:
• Real. Functional and live
• Beautiful. Polished enough to impress users
This shows investors you’re not just a talker. You are a doer who can actually build.
Example: I single‑handedly built Rivin.ai software for Walmart sellers and brands to analyze Walmart sales data. Before Rivin, I built software for Amazon sellers that drove $50M+ in GMV. I knew how to build a beautiful product from my last startup and used that knowledge to build the beautiful product we have today at Rivin.
You don’t need a fancy resume. Or a degree. Just a beautiful product to PROVE you can build.
💵 Step 2: Sell It (Even If It’s One Customer)
A flawless product is meaningless if no one will pay for it.
Most engineers think “if I build a good product, they will come.”
Nope. This is not how the world works.
Look around.
If you don't see any salespeople, you're the salesperson.
You need:
• A handful of paying customers
• Clear, documented feedback
• Real revenue (not a forecast)
Within 1 week of launching Rivin.ai I had a full calendar of sales calls, a handful of Walmart sellers paying for Rivin.ai to analyze Walmart sales data, and customers giving me product feedback. They paid me. That’s traction.
🧠 Step 3: The Secret Weapon? Pretend They’ve Already Invested
This is the game‑changer.
The step that most founders skip: Instead of waiting to “be ready” and then pitching, start by sending updates.
Here’s how I did it:
Curated a list of 50+ investors I respected
Sent weekly product updates and monthly financial snapshots
Shared:
What I built that week
Monthly MRR, burn rate, cash on hand, and MoM growth
Crucially: I never EVER asked for money.
I just acted like they were already invested.
👉 After a few weeks? This happened:
“Wait. Have we invested in your company? These updates are 🔥”
Exactly the reaction I wanted.
That’s how I landed Jason Calacanis’ firm to invest in Rivin.ai. There were no “VC lunches”, I never asked for money, and I don’t even think had a pitch deck.
Just undeniable traction and momentum.
That’s the secret.
💡 Why This Works
If you don’t have an Ivy League degree, you need to prove yourself:
Build = Show you can build something beautiful
Sell = Prove your product is needed by closing real customers
Update = Be disciplined and transparent
⸻
🔑 Moral of the Story?
You don’t need:
An Ivy League degree
A network
Demo day
A polished pitch deck
You do need:
A working, polished product
Real customers
Regular, disciplined updates
Relentless follow‑through
That was the story of how I raised initial investment for my startup Rivin.ai.
For context: Rivin.ai builds software for Walmart sellers and is trusted by multi-billion dollar brands to power their Walmart sales data insights, so they can make smarter inventory and purchasing decisions with Walmart data.
If you are not a pure SaaS startup your fundraising process will likely be pretty different. For example if you are a hardware or deep tech founder your fundraising will likely rely on hitting certain product development milestones since that’s the main “selling point” of your startup.
Hope this helps you out!