By name: email-outreach description: Helps write personalized outreach emails using YC's frameworks (startup/founder) or Sam McKenna's SMYKM method (enterprise/exec). Use when drafting cold, warm intro, or follow-up emails.
Task
Help draft or critique outreach emails — cold, warm intro, or follow-up — optimized for response rate.
First step: ask the user which framework to use via AskUserQuestion before drafting anything.
"Which outreach style do you want?"
- SMYKM (Show Me You Know Me) — Deep personalization for high-value targets, enterprise execs. Longer emails, "+" subject lines, objection handling built in.
- YC Startup — Tight, fast founder-to-founder outreach. 50-125 words, direct CTA.
Then read the corresponding reference file and follow that framework.
Mode Selection Guide
| Signal | SMYKM | YC |
|---|---|---|
| C-suite / VP / senior exec target | Yes | |
| Enterprise / large company | Yes | |
| Rich personal intel available | Yes | |
| High-value deal worth deep research | Yes | |
| Founder-to-founder | Yes | |
| Startup-to-startup, high volume | Yes | |
| Warm intro / referral | Yes | |
| Follow-up sequences (email 2+) | Yes (with SMYKM timing) |
Email Anatomy — Both Frameworks
YC: Opener -> Credibility -> Value prop -> CTA (50-125 words)
| Section | Length | Purpose | Key Rule |
|---|---|---|---|
| Personalized opener | 1-2 sentences | Show you researched THEM | About the recipient, not you |
| Credibility | 1 sentence | Why take you seriously | YC batch, relevant experience, social proof |
| Value prop | 1 sentence | ROI for them, not features | Use customer language |
| CTA | 1 sentence | Clear next step | 15 min ask, Calendly + availability option |
SMYKM: Subject line (SMYKM) -> First sentence -> Transition -> Value prop + Objection handling -> Close (longer OK for execs)
| Section | Purpose | Key Rule |
|---|---|---|
| Subject line | Gate to the email | SMYKM content + "+" format |
| First sentence | Preview text decides opens | Implied intro or straight SMYKM |
| Transition | Bridge personal to business | Stay conversational |
| Value prop + Objection handling | Challenge you solve + preempt #1 objection | Longer is better for execs |
| Close | Get the meeting | No calendar links, work around THEIR schedule |
Output Format
YC mode:
**Subject:** [short, intriguing, personalized]
**Body:** [50-125 words, 3-5 sentences]
---
Rationale: [Why this approach for this recipient]
SMYKM mode:
**Subject:** [SMYKM "+" format, specific to prospect]
**Body:** [5-part structure, longer is OK for execs]
---
Rationale: [Research layers used, objection anticipated, authentic tie-back]
Outreach Priority
Use the highest-available channel:
| Priority | Channel | When to Use |
|---|---|---|
| 1 | Your network | You already know someone at the company |
| 2 | Warm intro | A mutual connection can introduce you |
| 3 | YC alumni / community | Shared community affiliation |
| 4 | Personalized cold email | No connection — research hard, write tight |
Tone Rules
- Write like talking to a friend at a conference
- Read it aloud — if you wouldn't say it, don't write it
- "Hey" > "Hello", drop unnecessary "I" at sentence starts
- Use emotions ("I'd really appreciate...", "It would mean a lot...")
- Grammar must be flawless — recommend Grammarly for non-native speakers
- Never use buzzwords: "synergy", "leverage", "disrupt", "revolutionary"
Common Mistakes
| Mistake | Fix |
|---|---|
| Talking about yourself first | Lead with recipient |
| Vague ask ("pick your brain") | Specific CTA (15 min demo) |
| Too many value props | One value prop, one sentence |
| Generic "Hi there" | "Hey [First Name]" |
| No credibility signal | Add YC batch, relevant experience, or social proof |
| Demanding tone | Offer value first |
| Too long (>125 words) — YC mode | Cut to 50-125 words |
| Calendar link in close — SMYKM mode | "Do you have time over the next week or two?" |
| Inauthentic personalization | Every SMYKM ref must tie back to YOU |
When to Read Playbook
Read playbook.md when you need:
- Personalization strategies with concrete examples
- Follow-up sequence templates
- Subject line formulas
- Deliverability setup (SPF, DKIM, DMARC)
- Funnel math and volume benchmarks
- Recommended tools for prospecting, CRM, and automation
When to Read smykm.md
Read smykm.md when the user selects SMYKM mode, or when you need:
- The full 3-layer research framework (Human, Company, Space)
- Personalization pitfalls and don'ts
- The 5-part SMYKM email structure with examples
- SMYKM sequence timing (Thu/Fri send, <48hr follow-up, LinkedIn touch)
- Discovery call script and in-person meeting tips