Jason Calacanis Deal Memo Template: How Angels Evaluate You (With Examples)

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The deal memo template Jason Calacanis popularized exists to answer one blunt question fast: should an angel invest in you right now.

Founders ask me how angels like Jason make decisions so quickly and what goes into an investment memo that actually gets funded.

In this guide, I break down the Jason-style investment memo, show you how angels think, unpack a practical due diligence checklist, and share angel memo examples you can copy.

I write this in a direct, first-person voice so you can apply it today and raise faster.

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Jason Calacanis Deal Memo Template: How Angels Evaluate You (With Examples)

1) What Is the Jason Calacanis Deal Memo Template

Jason Calacanis is known for crisp, short memos that cut to signal and skip fluff.

His deal memo template is not a legal document.

It is a fast way to distill the why, the what, the who, and the risk into a one-page decision artifact.

Here is the spirit of it in one glance:

Team: Why this founder can win.
Product: What is built now and what makes it 10x better.
Market/Timing: How big and why now.
Traction: Proof it works with real users or revenue.
Business Model: How it makes money and unit economics.
Moat: Defensibility and compounding advantage.
Risks: Top three things that can break.
Terms: Valuation, round size, and allocation.

It is simple by design so the angel can decide within minutes, not weeks.

2) Why Angels Use a Deal Memo Template

Angels see dozens of startups each week and context switching kills accuracy.

A repeatable memo template reduces bias, captures the same fields for every deal, and lets angels compare apples to apples.

It also helps angels communicate the opportunity to their syndicate or co-investors without replaying the entire pitch.

As a founder, think of the memo as the “executive summary” investors wish you had sent before the call.

If you hand them the memo, you save them time and show you can self-edit.

3) The 5-Sentence Memo That Forces Clarity

When I prepare an angel memo, I start with five short sentences.

It sounds almost too simple, yet it forces sharp thinking.

Problem: One painful sentence in plain English.
Solution: One sentence on the product and 10x difference.
Why Now: One sentence on timing catalysts.
Traction: One sentence on current proof.
Ask: One sentence on terms and use of funds.

If those five lines are weak, the rest of the memo will not save the deal.

I coach founders to write these five lines before they touch a deck.

For more on crafting tight narratives, see our blog post: The 9 Slides That Actually Raise Money.

4) How I Score the Team Like an Angel

Team is the first filter in any investment memo.

I look for founder-market fit, shipping speed, and a clear history of obsession with this problem.

Here is the shortlist I use:

Edge: Founder has a unique advantage from domain, network, or tech skill.
Proof of speed: Demos ship weekly and metrics improve monthly.
Scrappiness: Creative wins without big budgets.
Ethics: References match claims and show consistency.

An anecdote beats a bio.

Tell me how you pulled an all-weekend fix to save a customer and shipped it Sunday night.

5) Market and Timing the Jason Way

Jason Calacanis often pushes on timing and tailwinds because timing turns tiny edges into big outcomes.

When I write a memo, I ask three timing questions.

Tech shift: Is there an enabling platform change like AI, mobile, or cloud that makes this newly possible.
Distribution shift: Is there a low-cost channel opening like short-form video, B2B communities, or app store policy changes.
Regulatory shift: Any laws or standards that now favor this solution.

Big market plus real timing beats big market alone.

6) Product and Proof: What Angels Need to See

Angels invest in momentum, not mockups.

When I evaluate product for an investment memo, I ask for three artifacts.

A live demo link: Video or sandbox I can click now.
Usage heat: DAU/WAU, time-in-product, or power-user cohort curves.
Customer love: One-minute testimonial clips or support tickets that show delight.

These beat polished slides because they show reality today.

For more on early traction, see our blog post: What Investors Want in Your First 1,000 Users.

7) Business Model and Unit Economics

Even at pre-seed, I want to see the shape of a viable business.

Your memo should include a single snapshot of unit economics.

ARPU or ACV: What an average user or contract pays now.
Gross margin: Cash margin after direct costs.
Payback: How many months to recoup CAC.
Churn: Logo and revenue churn for the last three months.

Early numbers will be noisy, but your logic should be clean.

Show me how better onboarding, pricing, or channels move these ratios in the next two quarters.

8) Distribution and Go-To-Market That Actually Works

Investors do not back products that cannot find customers.

In your deal memo template, write down one primary channel and one secondary channel, not five.

Channel: Where you reliably find target users today.
Message: What headline converts and why.
Motion: Self-serve, product-led sales, or outbound with clear steps.
Evidence: CAC screenshots or campaign cohorts.

Pick the one channel with the lowest CAC and highest intent, then pour gas later.

For channel strategy, see our blog post: Go-To-Market Playbooks That Don’t Burn Cash.

9) Defensibility and Moat Without Fairy Dust

Moats start small and deepen with compounding loops.

In my memos, I frame moats as practical flywheels.

Data loop: More users create better models, which improve product, which attract more users.
Distribution loop: Viral or ecosystem effects that cut CAC with scale.
Workflow lock-in: The deeper you sit in daily work, the harder it is to rip you out.
Economies of scale: Costs drop as you grow, widening margin gaps.

Write the loop as a sentence and show one metric that is moving in the right direction.

10) Financials, Runway, and the Use of Funds

Great memos show how new capital translates into line-item progress.

I ask founders to map every dollar to milestones, not generalities.

Runway: Months of cash at current and post-raise burn.
Hiring plan: Roles, start dates, and how they unlock metrics.
Milestones: The three measurable outcomes you will hit before the next round.
Contingency: What you cut if revenue lags.

This is how angels build confidence that you will not drift.

11) Terms, Valuation, and Signaling

Jason and most angels want simple, fair terms.

Your memo should include a clean terms block.

Instrument: SAFE, convertible note, or equity.
Cap/Discount: Valuation cap and any discount or MFN.
Round size: Amount raising and minimum check.
Committed: Capital soft-circled and lead status.

Anchor your valuation with traction, not vibes.

For valuation guidance, see our blog post: How to Set Your Seed Round Valuation Without Guessing.

12) Risks and What You Are Doing About Them

Honest risk framing increases trust.

In my memos, I list the top three risks and one active mitigation for each.

Distribution risk: Counter with a pilot pipeline and partner commitments.
Technical risk: Counter with a roadmap, benchmarks, and hires.
Regulatory risk: Counter with counsel, compliance steps, and geo focus.

Smart angels appreciate clear-eyed founders more than blind optimists.

13) The Due Diligence Checklist Angels Actually Use

A tight due diligence checklist speeds yes decisions.

Here is the short list I share with founders before the call.

Corporate: Charter, cap table, SAFEs or notes, option pool plan.
Product: Demo link, repo overview or architecture diagram, roadmap.
Metrics: GA or Mixpanel screenshots, revenue exports, cohort views.
Customers: Top five logos, LOIs, testimonials, churn reasons.
Team: Bios, references, hiring plan, contractors list.
Legal: IP assignments, licenses, privacy policy, security posture.
Financial: P&L, cash balance, burn, projections, runway math.

For a deeper checklist, see our blog post: The Founder’s Due Diligence Checklist.

14) Data Room Essentials and Naming Conventions

Most founders lose days to messy data rooms.

I use one simple structure and consistent names so angels do not hunt for files.

00_Overview: One-pager, five-sentence memo, 3-minute demo.
01_Product: Roadmap, architecture, security overview.
02_Metrics: Growth dashboard, cohorts, funnel.
03_Customers: Logos, pipeline, testimonials, churn analysis.
04_Financials: P&L, cash, runway, hiring plan.
05_Legal: Charter, cap table, IP, contracts.
06_Team: Bios, references, org plan.

Use read-only links and track views so you can follow up with context.

For help building the room, see our blog post: How to Build a Killer Data Room in 24 Hours.

15) Red Flags I Call Out Before an Angel Does

Almost every no can be traced to a few avoidable red flags.

In my memos, I name them early and explain the fix.

Overbuilt MVP: Shipping slow and chasing perfection.
Unclear ICP: Everyone is a customer which means no one is.
Leaky funnel: Great top-of-funnel with zero activation focus.
Vanity metrics: MAUs without retention mean nothing.
Legal mess: No IP assignment or mis-signed SAFEs.

Fixes are often boring but effective.

Pick one ICP, define one activation action, and iterate weekly demos.

16) How to Write Your Own Founder-Facing Angel Memo

Founders can win meetings by sending their own investment memo first.

Here is my founder-facing template you can copy and paste.

Title: Startup name, one-line, and stage.
Five sentences: Problem, Solution, Why Now, Traction, Ask.
Snapshot: Team, Market, Product, Model, Moat, Risks.
Metrics panel: Growth, retention, revenue, payback.
Terms: Instrument, cap, size, committed.
Links: Deck, data room, demo video.

Send that before your meeting and watch the questions get sharper and faster.

For downloadable capitaly.vc resources, templates, and examples, see our blog: Fundraising Templates Library.

17) Angel Memo Example: Consumer SaaS

Here is a condensed, realistic angel memo example I would send for a consumer SaaS app.

Problem: Creators waste 6 hours a week editing short-form video across platforms.

Solution: ClipKit auto-edits long videos into viral clips with AI, posting to TikTok, Reels, and Shorts in one click.

Why Now: Short-form consumption is exploding and new APIs enable hands-free posting.

Traction: 12,400 MAUs, 1,900 paying at $15 MRR, 4.7-star rating, 36% month-over-month growth, 30% D30 retention.

Ask: Raising $1M SAFE at $12M cap to hire 2 ML engineers and scale creator partnerships.

Team: Former PM at a creator tools unicorn and YC alum ML engineer.
Model: Freemium to $15 and $49 tiers, 82% gross margin, 5-month payback.
Moat: Dataset from 3M edited clips tied to performance outcomes.
Risks: Platform policy changes and algorithm shifts, mitigated by multi-platform posting.
Terms: SAFE, $12M cap, $400k committed.

That is enough for an angel to decide on a follow-up within minutes.

18) Angel Memo Example: B2B AI Infrastructure

Now a B2B example focused on enterprise AI reliability.

Problem: Enterprises cannot ship LLM apps because outputs are unstable and audits are painful.

Solution: GuardRail monitors prompts, detects hallucinations, and auto-switches models to meet accuracy SLOs.

Why Now: Enterprises are mandating AI usage but require verifiable reliability for regulated workflows.

Traction: 6 pilots, 2 paid design partners at $5k MRR each, 1,200 developer signups, SOC 2 in progress.

Ask: Raising $2.5M SAFE at $18M cap to complete SOC 2 and scale field sales.

Team: Ex-FAANG infra lead and PhD in NLP evaluation.
Model: Usage-based with enterprise floor, 89% gross margin, target 12-month payback for mid-market.
Moat: Feedback loops from production traffic and fine-tuned evaluation models.
Risks: AI platform vendors bundling competing tools, mitigated with neutral, multi-cloud support.
Terms: SAFE, $18M cap, $1.2M soft-circled.

Notice how the memo balances technical depth with business clarity.

19) VC Memo vs Angel Memo: What Actually Differs

A VC memo is longer, committee-driven, and references market maps and comps.

An angel memo is faster, founder-centric, and focused on near-term proof.

Here is how I summarize the difference.

Time: Angels write in hours, VCs write in weeks.
Depth: VCs include market sizing, competitive grids, and exit analysis.
Process: VC memos are consensus artifacts, angel memos are conviction artifacts.
Outcome: VC memos defend a partnership decision, angel memos memorialize a personal bet.

If you can satisfy an angel memo cleanly, you already have a strong base for a VC memo later.

For VC processes, see our blog post: Inside the VC Investment Committee.

20) Using capitaly.vc Resources and Templates to Win

I have seen founders shave weeks off their round by starting with the right template.

Here is the quick stack of capitaly.vc resources I recommend.

Deal memo template: Duplicate the format in this article and tailor it to your stage.
Due diligence checklist: Build your data room with the checklist above and keep it updated weekly.
Founder video: Record a three-minute Loom demo and place it at the top of your folder.
Metric dashboard: Ship an investor-facing dashboard that updates automatically.
Email system: Use short, numbered updates that link back to the memo and data room.

For more templates and guides, see our blog post: AI-Ready Fundraising Stack.

BONUS: The One-Page Deal Memo Template You Can Copy

Here is a one-page structure that mirrors the Jason Calacanis style and keeps angels focused.

Header: Company, one-line, stage, date.
Five sentences: Problem, Solution, Why Now, Traction, Ask.
Team: Founder-market fit bullets and key wins.
Market: ICP, TAM/SAM/SOM short notes, timing catalysts.
Product: What is live, demo link, next two releases.
Model: ARPU/ACV, margin, payback, churn.
Moat: Data, distribution, workflow lock-in, or scale.
Traction: Growth, retention, revenue, pipeline.
Risks: Top three with mitigation.
Terms: Instrument, cap, size, committed, allocation.
Links: Deck, data room, demo video.

Keep it to one page and update the numbers monthly during your raise.

How Angels Use AI to Speed Investment Memos

Today’s angels use AI to summarize decks, parse data rooms, and benchmark metrics against their portfolio.

I recommend founders lean into this and make your materials AI-friendly.

Plain text: Include a text version of your five-sentence memo for easy copying.
Structured tables: Present metrics in simple CSV or clean tables.
Short videos: Under three minutes with captions for transcription.
Consistent names: Files and tabs named clearly so LLMs do not get confused.

This is Generative Engine Optimization in practice and it helps both humans and AI evaluate you faster.

Founder Mistakes in Investment Memos I See Weekly

After reading hundreds of memos, I see the same errors again and again.

Fix these and you jump a tier.

Pitch inflation: Overstating traction and triggering deeper skepticism.
Jargon soup: Using buzzwords instead of clear value.
No downside: Hiding risk and forcing the investor to discover it.
Messy numbers: Inconsistent metrics across deck, memo, and data room.
Weak ask: Unclear terms or a moving target round size.

Write simply and make it easy to say yes.

Turning Your Memo Into a Weekly Investor Update

The best founders convert the memo into a weekly or biweekly update that moves investors from curious to committed.

Here is my format.

Subject: Company – Week of MM/DD – growth, product, ask.
Top line: M/M growth, retention, revenue, cash.
What shipped: Three bullets with links or GIFs.
What’s next: Three bullets with dates.
Asks: One or two specific intros or hires.
Memo link: Updated one-pager with numbers.

Consistency builds trust and creates momentum during the raise.

For email tactics, see our blog post: Investor Updates That Get Replies.

Signals Angels Love to See in Your Memo

Great memos carry a handful of high-signal details that make angels lean forward.

I prioritize these when I write.

Customer urgency: Short sales cycles or inbound demand.
Fast iteration: Weekly release notes or changelog links.
Unfair access: Unique distribution partners or datasets.
Capital efficiency: Progress with little spend and a clear plan to keep it tight.
Founding team chemistry: Years working together or prior wins.

Signal density is what separates fundable memos from forgettable ones.

How to Handle Weak Areas Without Losing the Room

No startup is perfect and angels know that.

When a section is weak, I acknowledge it and reframe with a concrete plan.

Low retention: Call it out and show the activation experiment calendar.
Thin pipeline: List the 20 named targets and the next five intros you are pursuing.
No revenue yet: Present signed LOIs and a time-boxed pricing test.

Owning the gap lowers perceived risk more than hand-waving ever will.

FAQs: Quick Answers Angels Want Up Front

1) What exactly is a deal memo template.

It is a structured one-page summary of your company that angels use to decide whether to invest or take a deeper meeting.

2) How is the Jason Calacanis style different.

It is shorter, punchier, and focused on immediate proof like traction, team edge, and why now.

3) Do I need a full business plan to raise from angels.

No, a crisp investment memo plus a working product and a simple data room often beats a long plan.

4) What traction do angels expect to see.

Anything that proves pull like active users, retention, paid pilots, or signed LOIs.

5) How long should my memo be.

One page is best and two pages max with links to a deck, demo, and data room.

6) What goes in the due diligence checklist.

Company docs, product artifacts, metrics, customers, financials, legal, and team references.

7) Should I include a valuation in the memo.

Yes, include your instrument, cap, round size, and what is already committed to make it easy to say yes.

8) How do I show moat at pre-seed.

Describe your compounding loops like data advantage, workflow embed, or partner distribution that gets stronger with scale.

9) Can I send a memo before a warm intro.

Yes, a sharp memo plus a short demo link can turn a cold outreach into a meeting.

10) How often should I update the memo during the raise.

Update the top-line numbers weekly and version the file so investors always see the latest.

11) What if my numbers are small.

Show growth rates, cohort improvements, and clear next steps rather than hiding small absolute numbers.

12) Do angels care about SOC 2 or security early.

Yes if you sell to enterprises and you should state your current posture and timeline for audits.

Conclusion: Make Your Memo the Fastest Yes of an Angel’s Week

Your job is to remove friction, show undeniable proof, and make the next step obvious.

If you use this Jason Calacanis deal memo template, include a clean due diligence checklist, and send clear updates, you will raise faster and with better partners.

Turn this template into your standard operating system and let the momentum do the rest.

To go deeper and access capitaly.vc resources and templates, Subscribe to Capitaly.vc Substack (https://capitaly.substack.com/) to raise capital at the speed of AI.