The Exact Emails I Used to Raise an Angel Investment From Jason Calacanis
Hey all— after my last post on how I raised money from one of the most famous angel investors of all time, Jason Calacanis, the response blew me away. It went semi-viral with over 60,000 views on Reddit— and honestly I’m happy that many of you found it valuable :)
Here’s the original post for context if you missed it:
🔗 How I Raised Money From One of the Most Famous Angel Investors of All Time
Since then, a bunch of you DM’d me asking for the actual email templates I used to raise the round.
So here we go!
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🧠 TL;DR from my last post: You Only Need 2 Things to Raise
A beautiful, working product
Real paying customers
Nothing else matters.
Then comes Step 3: Getting in front of investors — even if you have no network.
The Strategy? Act Like They Already Invested
When I was raising for Rivin.ai, I didn’t have warm intros or VC friends. I just made a list of 50-100 angel investors I respected and started emailing them like they had already invested.
No pitch deck. No “ask.” Just regular, short updates showing momentum.
Here’s how I structured my updates:
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📬 1. Weekly Product Updates
Purpose: Answer the question: What did you ship this week?
Subject line: Rivin.ai Product Update v1.2
Hey [Investor Name] 👋
This week at Rivin we launched [feature or improvement] and [feature or improvement] !
[Explain in one sentence what each feature or improvement does]
Customers are giving feedback [feature or result — ideally with a short quote or stat]
[ sign off with focus for next week e.g. improving feature or working toward big launch]
Best,
Emiliano
Founder @ Rivin.ai
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📈 2. Monthly Traction Updates
Purpose: Answer the question: How is business going this month?
Subject line: Rivin.ai – June 2025 Update
Hey [Investor Name] 👋
June Stats
– Users: [Number] (% MoM)
– MRR: $[Amount] (% MoM)
– Expenses: $[Amount] (% MoM)
– Cash: $[Optional] (% MoM)
[ This month’s biggest win: E.g. “This month we landed our first $1k MRR customer in the CPG space, (ABC Brands), super excited to get them rolling and onboarded to our ___ product.”]
[ What we’re focused on next month: E.g. “For July our #1 priority is improving our onboarding flow and outbound to enterprise brands. Our goal is to use ABC Brands as a case study and go after similar sized brands.”]
Until next month,
Emiliano
Founder @ Rivin.ai
^Note: For each monthly update for each metric you NEED to include (+__% MoM) for each metric
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🧲 What Happens Next?
After a few updates, most investors are in a state of semi-confusion and ask themselves:
“Wait… did I invest in this startup? Why am I getting updates?”
That’s exactly what you want.
Eventually, their curiosity takes over. Investors will check out your product. Some will even sign up. And when your updates consistently show momentum, they’ll reach out and ask for a call or more info.
You don’t need a warm intro. You don’t need a pitch deck. You don’t need to beg.
You just need to build, sell, and update.
It's not complicated.
When your product and traction are good enough, they’ll respond.
Note: As mentioned in my previous post these emails will vary slightly from startup to startup. For context, my startup Rivin.ai builds software for e-commerce sellers to analyze Walmart sales data— we are a pure SaaS startup.
If you run a deep tech or hardware startup your emails will have to be more product centric since funding for these types of startups usually depend on technical breakthroughs.
Let me know if you have any questions or which post you’d like to see next :)