How To Convert Customers With Cold Emails with Aaron Epstein | Startup School

The Ultimate Cold Email Strategy

The Game-Changing Truth:

Get a warm intro - this single strategy will transform your email success rate completely.

Why Warm Intros Dominate:

• 2-3x higher conversion rate compared to cold emails
• Recipients trust recommendations from mutual connections
• Bypasses the initial skepticism barrier entirely
• Creates immediate credibility and context

Your Warm Intro Hunting Strategy:

1. LinkedIn Network Mining - Search through all connections systematically
2. Friends & Friends-of-Friends - Leverage personal relationships
3. Professional Connections - Current and former co-workers
4. Alumni Networks - School and employer alumni databases
5. Industry Contacts - Turn over every rock and stone

When Cold Email Becomes Necessary:

While warm intros aren't always possible, understanding when to go cold is crucial for:

• Sales outreach to potential customers
• Recruiting top talent for your team
• Partnership development opportunities
• User research and feedback collection
• Mentor relationships with experienced founders

The Reality Check:

Most cold emails are terrible, which means the bar is really low for you to stand out and get responses.

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Understanding Your Conversion Funnel Mathematics

The Funnel Mapping Process:

Start with your goal and work backwards - this reverse engineering approach reveals the true scope of cold email campaigns.

Sample B2B Software Company Funnel:

1. Goal: 1 new customer
2. Demo to Customer: 10% conversion (need 10 demos)
3. Response to Demo: 25% conversion (need 40 responses)
4. Opens to Response: 10% conversion (need 400 opens)
5. Sent to Opens: 50% conversion (need 800 emails sent)

The Mathematics Reality:

• 800 emails sent → 400 opens → 40 responses → 10 demos → 1 customer
• You need dozens of emails per day, possibly 50+ daily for meaningful results
• A handful of emails per week won't cut it

Critical Implementation Guidelines:

Start manually, not with automation:

• Write personalized emails yourself initially
• Learn what works through direct experience
• Scale the process only after proving effectiveness
• Track and measure every conversion rate step

Optimization Strategy:

• Track conversion rates at each funnel step
• Identify bottlenecks where rates are especially low
• Focus improvement efforts on the weakest conversion points
• Remember: conversion rates decrease as you scale

Important Warning:

Fix low conversion rates while doing manual outreach before scaling - they only get worse with automation as you target less ideal prospects.

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The Power of Laser-Focused Targeting

The Targeting Revolution:

Better targeting is the highest leverage improvement you can make to your email campaigns - it beats any subject line trick or email template.

The YC Philosophy Applied:

Quality vs. Quantity Approach:

• 100 targeted emails with high open rates and response likelihood
• Beats 1,000 untargeted emails that mostly get deleted
• Iterative improvement as you learn to qualify leads better
• Higher ROI on time and effort invested

The Recipient's Decision Screen:

What they see determines everything:

• Sender name (personal name vs. company name)
• Subject line (short, relevant, interesting)
• Preview text (tiny glimpse of first sentence)

Winning Formula for "From" Field:

Use your personal name - feels human rather than corporate

Subject Line Excellence:

Choose something short, relevant, interesting:

• "Hey, quick question"
• "Can I get your advice?"
• "Help a fellow founder"
• "Hello from [Your Company Name]"

Channel Selection Strategy:

1. Email: Usually the best option
2. LinkedIn: Usually worse (often overwhelming/spam-filled)
3. Text messaging: Can be more personal but only with explicit permission

Industry Adaptation Required:

• Some industries: LinkedIn feels overwhelming and spam-filled
• Other industries: LinkedIn messages feel special and rare
• Adapt your approach based on your specific industry and use case

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Essential Insights:

1. Warm introductions deliver 2-3x higher conversion rates - This single strategy change can transform your entire outreach effectiveness
2. The 800-email reality check - Understanding funnel mathematics prevents unrealistic expectations and helps you plan appropriate volume
3. Targeting trumps everything - Better prospect selection beats clever subject lines and fancy templates every time

Actionable Insights:

• Mine your entire network systematically before going cold - LinkedIn, alumni networks, former colleagues, and friends-of-friends
• Start with manual, personalized emails to learn what works before scaling with automation
• Track every conversion rate in your funnel to identify the biggest improvement opportunities
• Use personal names in sender fields and keep subject lines simple, human, and curiosity-driven
• Choose email over LinkedIn in most cases, and never text without explicit permission

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People Mentioned:

• Aaron Epstein - Y Combinator Group Partner sharing cold email conversion strategies

Companies & Products:

• Y Combinator - Startup accelerator providing framework for product-market fit and targeting strategies
• LinkedIn - Professional networking platform for finding warm introductions and prospect research

Concepts & Frameworks:

• Conversion Funnel Mapping - Reverse engineering from goals to required actions and volume
• Warm Introduction Strategy - Leveraging network connections for higher response rates
• Targeting vs. Volume - Quality prospect selection over mass email distribution
• Manual-First Approach - Learning through personalized outreach before automation

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The Complete Email Discovery Toolkit

The Email Detective Arsenal:

When you need to reach strangers, here's your step-by-step hunting strategy:

Personal Network Approach:

1. Ask mutual connections if they have the email address
2. Request warm introductions instead (always better than just getting the email)

Digital Detective Work:

3. LinkedIn outreach - Connect and message directly
4. Personal blogs/websites - People often list their contact info
5. Company email pattern guessing - If you know the format (firstname.lastname@company.com)

Professional Tools That Work:

• LinkedIn Sales Navigator - Find and contact relevant prospects
• Apollo.io - Comprehensive email finding and verification
• Hunter.io - Domain-based email discovery
• Clearbit - Email enrichment and verification

The Company Format Hack:

If you discover one employee's email format, you can often guess others:

• Pattern: firstname.lastname@company.com
• Apply to any employee name from LinkedIn or company website

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Personal Branding for Early-Stage Founders

The Brand Reality Check:

Your company brand won't help you when you're small - nobody knows who you are, but this creates a unique opportunity.

The Personal Brand Advantage:

What Really Matters in Early Days:

• Your personal communication style and authenticity
• Level of personalization you demonstrate
• Effort and work visible in your outreach
• Personal commitment to their success

The Risk-Reduction Strategy:

People bet on YOU personally, not just your company:

• Working with startups is inherently risky
• Personal connection reduces perceived risk
• Your individual credibility becomes the deciding factor

The Above-and-Beyond Approach:

Building Long-Term Brand Equity:

• Early personal relationships scale into company credibility
• Consistent quality interactions build reputation over time
• Personal investment in success creates lasting partnerships

The ROI Reality:

Remember: the highest ROI for increasing open rates still comes from better targeting, not just personal branding efforts.

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The Science of Response-Generating Email Copy

Principle #1: Have a Focused, Specific Goal

One outcome, one action, one response - everything else creates decision paralysis.

The Single-Goal Strategy:

• Next step in funnel - getting a conversation started
• One clear action - respond, click, or intro
• All copy drives toward that single objective
• Every word counts - delete anything that doesn't move toward the goal

The Paradox of Choice Problem:

Result: People delete or archive your email instead of responding.

Principle #2: Be Human

Emotions and informal language separate you from automated spam.

Human Language Indicators:

• Emotional expressions: "I'd love to," "it would mean a lot," "I'd really appreciate"
• Informal greetings: "Hey" or "Hey Aaron" vs. "Hello Mr. Epstein"
• Casual formatting: No capitalization, occasional typos acceptable
• Personal touches: "Thanks, you have no idea how much this helped"

Creative Personalization Examples:

The Animated GIF Story:

The Friend Test:

The Writing Process:

1. Open your email editor (not Google Docs)
2. Put specific person's name in the "To" field
3. Write with that specific person in mind
4. Read it out loud to test for awkwardness
5. Change anything you wouldn't say face-to-face

Principle #3: Personalize Beyond Name Swapping

Real personalization shows research and genuine interest.

The Name Power:

• "Hi there" = feels generic and spam-like
• "Hey Aaron" = feels written specifically for me

Shallow vs. Deep Personalization:

Shallow (feels like a template):

• "Hey, love what you're doing at Creative Market"

Deep (shows real research):

• "I'm a huge Creative Market fan ever since you launched the photos category, it's now my go-to resource"

Why Deep Personalization Works:

• Shows actual research on the product and company history
• Demonstrates they might be a real user of your product
• Creates excitement to respond and connect
• Proves time investment in learning about you specifically

The Key Insight:

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Essential Insights:

1. Email discovery is systematic, not magical - Use the right combination of personal networks, digital detective work, and professional tools to find anyone
2. You are the brand in early-stage startups - Personal credibility and relationship-building matter more than company recognition when you're small
3. One focused goal prevents decision paralysis - Multiple asks in emails create overwhelm and lead to deletion rather than response

Actionable Insights:

• Master the email discovery toolkit including Apollo.io, Hunter.io, and LinkedIn Sales Navigator for systematic prospect research
• Put your personal cell phone number in emails and offer 24/7 availability to demonstrate extraordinary commitment
• Write like you talk to a friend - use emotional language, informal greetings, and casual formatting to stand out from automated messages
• Personalize beyond name-swapping - show real research about their product, company history, or specific achievements
• Use the "read out loud" test - if you wouldn't say it face-to-face, rewrite it to be more human

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Companies & Products:

• Creative Market - Aaron Epstein's former startup, used as personalization example
• Apollo.io - Email discovery and verification tool
• Hunter.io - Domain-based email finding service
• Clearbit - Email enrichment and contact data platform
• LinkedIn Sales Navigator - Professional prospecting and contact tool

Concepts & Frameworks:

• The Seven Principles of Effective Email Copy - Systematic approach to writing response-generating emails
• Personal Branding for Early-Stage Startups - Using founder credibility when company brand is unknown
• Focused Goal Strategy - Single-outcome email design to prevent decision paralysis
• Deep vs. Shallow Personalization - Research-based customization vs. template variable swapping
• The Friend Test - Writing emails as you would speak to friends for authentic tone

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The Secret Psychology of Deep Personalization

The Uncommon Commonalities Principle:

Find unique shared experiences that aren't obvious - these create powerful emotional connections that drive responses.

The Bad Example (Common Commonality):

The Good Example (Uncommon Commonality):

Why Uncommon Commonalities Work:

• Create instant emotional connection through shared unique experiences
• Trigger empathy and support - "I know what it's like to be in their shoes"
• Build trust faster than generic similarities
• Make you memorable among hundreds of generic emails

The Research Investment Required:

You have to do the work to discover these connections:

1. Research the company thoroughly
2. Find the right contact person
3. Look them up on LinkedIn for background details
4. Use their product to understand it deeply
5. Connect personal experiences to their situation

Examples of Uncommon Commonalities:

• Same college + specific buildings/experiences
• Same previous company or boss
• Same hometown or unusual location
• Same niche hobby or interest
• Same specific certification or program
• Same unusual career transition

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Principle #4: The Mobile-First Length Strategy

The Wall of Text Problem:

Long emails = instant delete for most recipients - especially in our mobile-first world.

The Mobile Reality:

The Cognitive Overhead Trap:

If it requires mental effort, it gets postponed or deleted:

Immediate Action Triggers:

• Easy to read on mobile screen
• Quick to respond in the moment
• Clear next step that takes seconds
• No cognitive overhead required

The Archive Death Spiral:

If your email is too long or complex:

1. Archive for later (but never gets revisited)
2. Flag to respond (but gets forgotten)
3. Delete immediately (most common outcome)

The Sweet Spot Formula:

• Short enough to read in 30 seconds
• Clear enough to understand immediately
• Simple enough to respond without thinking
• Actionable enough to take immediate action

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Principle #5: Strategic Credibility Building

The Credibility Toolkit:

Use these elements to get taken seriously from the first line:

Educational & Professional Credentials:

• Former schools you've attended (especially prestigious ones)
• Companies you've worked at (recognizable names)
• YC participation (if applicable - often enough to open doors)
• Other impressive achievements relevant to your industry

Social Proof Through Customers:

Share well-known customer names when your company is live:

• Competitor usage - shows market validation
• Well-known brands - creates trust through association
• Industry leaders - demonstrates product quality

Expert Positioning:

Establish yourself as an industry expert:

• Share interesting data or trends relevant to their industry
• Publish industry-specific insights your customers find useful
• Demonstrate deep knowledge of their space and challenges

Connection-Based Trust:

Mention shared connections for baseline trust:

• Mutual contacts who can vouch for you
• Shared network members who recommended you reach out
• Common professional circles or industry associations

The Balance:

Include credibility markers naturally in your email without making it feel like a resume dump - weave them into your story and value proposition.

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Principle #6: The Reader-Centric Transformation

The Reframing Strategy:

Transform all "I" statements into "you" and "your" language - make them the hero of your story.

The Personal Problem-Solution Story:

The Empathy Connection:

Why This Works:

People connect when they know you understand their problem:

• Shared pain creates trust - "you've been where I am"
• Personal investment shows commitment - "you really care about solving this"
• Future dedication demonstrates reliability - "you'll be here to support me"

The Language Discovery Trick:

Ask your users: "How would you describe my company?"

• Use their exact phrase when reaching out to similar prospects
• Put that phrase as the header on your website
• Mirror their language because it resonates with similar people

The Respect Principle:

Never make demands in your emails:

• No deadlines - "respond to me by this date"
• Respect their time - you're in their inbox
• No pressure tactics - it's not their responsibility to get back to you

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Principle #7: The Concrete Next Step Formula

The Clear Action Strategy:

End with a concrete, specific next step that removes all ambiguity about what you want.

Winning Call-to-Action Examples:

• "Reply to let me know" - Simple response request
• "Click here to get started" - Direct action with link
• "Can you intro me to Aaron?" - Specific connection request
• Clear outcome - exactly what you want them to do

The Formatting Rules:

Make your CTA impossible to miss:

Standalone Presentation:

• Its own paragraph - separate from other content
• Its own sentence - not buried in text
• Right before sign-off - last thing they see

The Scanning Behavior:

The Two-Second Decision:

People quickly assess:

• Can I do this now? (immediate action)
• Will this take time? (gets postponed/deleted)

By ending with a clear call to action, you're more likely to get somebody to take that next step.

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The Complete Framework for Email Excellence

The Seven Principles Recap:

1. Have a focused, specific goal - single outcome, no decision paralysis
2. Be human - emotional language, informal tone, personal touches
3. Personalize - uncommon commonalities and deep research
4. Keep it short - mobile-friendly, easy immediate response
5. Establish credibility - strategic social proof and expertise
6. Make it about the reader - their problems, their language, their benefits
7. Have a clear call to action - concrete next step in its own paragraph

The Top 5% Promise:

The Follow-Up Strategy:

One email is often not enough - people are busy, distracted, or on vacation.

The Persistence Formula:

• Manually follow up 2-3-4 times as needed
• Wait a few days between emails
• Get creative with each follow-up attempt

The Creative Follow-Up Story:

The Professional Mindset:

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Essential Insights:

1. Uncommon commonalities create instant emotional connections - shared unique experiences like same college buildings trump obvious similarities like gender or location
2. Mobile-first length determines immediate action - long emails get archived or deleted while short emails get responded to in the moment
3. The 7 principles framework puts you in the top 5% - following this systematic approach makes your emails nearly impossible to ignore

Actionable Insights:

• Research deeply to find uncommon commonalities - same schools, companies, unusual backgrounds, or niche interests that create real connection
• Write for mobile immediate response - keep emails short enough to read and respond to in 30 seconds on a phone
• Use your users' exact language to describe your company - ask them directly and mirror their words in outreach
• Make call-to-actions standalone paragraphs right before sign-off so recipients can quickly assess if it's a 2-second task
• Follow up creatively 2-4 times with persistence, not aggression - "free donuts" subject lines and office visits show dedication

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Companies & Products:

• Y Combinator (YC) - Startup accelerator that provides instant credibility for email outreach

Concepts & Frameworks:

• The Seven Principles of Effective Email Copy - Complete framework for writing response-generating emails:

1. Focused, specific goal
2. Be human
3. Personalize with uncommon commonalities
4. Keep it short
5. Establish credibility
6. Make it about the reader
7. Clear call to action

• Uncommon Commonalities Strategy - Finding unique shared experiences that create deeper connections than obvious similarities
• Mobile-First Email Length - Writing for immediate mobile response rather than desktop reading
• Reader-Centric Language Transformation - Converting "I" statements to "you" and "your" language
• Creative Follow-Up Persistence - Multi-touch sequences with unique approaches like "free donuts" subject lines

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Dissecting Epic Email Failures

Bad Example #1: The Targeting Disaster

Subject: Follow-up on order processing time The Fatal Flaw: Selling shipping services to a digital download company

The Email:

Why It Failed Spectacularly:

Creative Market sold digital design assets downloadable from the internet - they didn't ship physical products at all.

The Lesson: Perfect execution can't save terrible targeting.

Bad Example #2: The Generic Spam Disaster

Subject: Partnership inquiry The Problems: No name, vague ask, anonymous sender, spam disclaimer

The Email Breakdown:

• "Hey there" instead of using Aaron's name
• "Your audience looks interesting to us" - completely generic
• "Do you collaborate somehow to make extra bucks" - unclear ask
• No signature - anonymous sender
• "If you don't want to hear from me anymore just let me know" - admits it's spam

Bad Example #3: The Self-Centered Disaster

Subject: Freelancer offering services The Fatal Flaw: Everything about the sender, nothing about the recipient

The "I, I, I" Problem:

Key Mistakes:

• Explaining how they found the email (irrelevant to recipient)
• Entire focus on sender's background and achievements
• No mention of recipient's problems or how they can help
• Zero research into the recipient's actual needs

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Dissecting a Perfect Cold Outreach

The Winning LinkedIn Message:

• Subject: Go Terps!
• The Strategy: Uncommon commonalities + credibility + clear ask

The Perfect Opening:

Why This Worked:

• Specific building reference at University of Maryland
• Immediate uncommon commonality - both went to same school
• Shows actual research and context about Aaron's background

The Credibility Builder:

Strategic Elements:

• Google credentials establish technical competence
• Co-founder mention shows serious commitment
• Product description gives context for the ask

The Respectful Ask:

Why This Was Perfect:

• Fellow Terp reinforces the commonality
• Specific request - review YC application
• Pre-work mentioned - shows they won't waste his time
• High-value help requested, not low-hanging fruit

The Clear Call-to-Action:

Execution Excellence:

• Simple next step - just provide email address
• Clear process - they'll send the doc
• Gratitude in advance - respectful tone

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Aaron's Creative Market Recruitment Masterclass

The Challenge:

Recruit designers as first sellers for Creative Market marketplace launch

The "Template" That Felt Personal:

Every element except name and URL was templated, yet felt completely customized.

The Psychological Tricks Used:

1. Exclusivity Language:

• "Want to be one of the first Creative Market sellers"
• "We're just starting to open the doors"
• "Special link to start setting up"
• "Handpicked sellers only"
• "Welcome to the club"

2. Informal, Conversational Tone:

3. Behind-the-Scenes Vulnerability:

• "It's still super early in the rollout"
• "Let me know if you run into any bugs"
• "We're working hard to improve things every day"

4. Personal Investment Appeal:

• "I'd love any thoughts or feedback"
• "Your feedback is super important to us"
• "Look forward to hearing your thoughts"

The Secret Sauce:

Key Elements:

• Smiley faces for informal feel
• Conversational transitions ("oh and...")
• Exclusive positioning throughout
• Personal attention emphasis

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Before & After: The Smoothie Company Transformation

The Original Email (Weak):

Focus: Company's demo day goal and product features

Problems with Original:

• All about the company's needs (demo day goal)
• Asking for forwarding (extra friction)
• Transactional feel (feedback in exchange for smoothies)
• Weak value proposition for recipient

The Reframed Email (Powerful):

Subject: Smoothie Party - Current YC Company Focus: Fun experience for the recipient's team

Why the Reframe Worked:

• "Smoothie party" - fun, exciting concept
• "For the whole company team" - benefit for everyone
• "Like happy hour but smoothies" - familiar, appealing analogy
• Simple yes/no question - easy decision
• Founder personally coming - high-touch service

The Sales Strategy:

Get in the door with value, then convert to long-term deals once they experience the product and service quality.

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Final Implementation Strategy

The Manual-First Mandate:

Start manually to learn, scale later - automation without learning is guaranteed failure.

The Time Investment Reality:

Block off hours per day if cold emails are important to your growth strategy:

• Do it incredibly well rather than doing it quickly
• Focus on the return - worth the investment when done right
• Learn before you scale - understand what works first

The Founder Advantage:

People take emails from founders/CEOs way more seriously than from employees.

Your Small Company Advantage:

Being small is your secret weapon:

• Personalized attention you can give
• Dedicated effort per email
• Special feeling you can create
• Direct founder access that big companies can't offer

The Daily Volume Target:

Send dozens of emails per day - block off the time and do the work to see results.

The Success Formula:

Personalize, be human, be persistent, and do the work.

The Measurement Imperative:

Track and measure your funnel:

• Conversion rate at each step - opens, responses, demos, customers
• Identify drop-off points and focus improvement there
• Continuous optimization based on real data

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Essential Insights:

1. Perfect execution can't save terrible targeting - the most beautifully written email fails if sent to the wrong audience
2. Templates can feel personal with the right psychological tricks - exclusivity language, conversational tone, and vulnerability create connection even in mass emails
3. Founders should send emails personally - recipients take founder outreach much more seriously than employee or automated messages

Actionable Insights:

• Research deeply before writing - understand their actual business model and needs to avoid embarrassing targeting mistakes
• Use uncommon commonalities immediately - specific shared experiences like same college buildings create instant connection
• Reframe benefits around recipient experience - "smoothie party for your team" beats "help us reach our demo day goal"
• Include exclusivity language in templates - "handpicked," "special link," "welcome to the club" make mass emails feel personalized
• Block dedicated hours daily for manual cold email outreach rather than trying to automate immediately

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Companies & Products:

• Creative Market - Aaron Epstein's former marketplace startup for digital design assets, used as email template example
• University of Maryland - School referenced in successful LinkedIn outreach example with Van Munching Hall building
• Google - Former employer credential used to establish credibility in cold outreach
• Y Combinator (YC) - Startup accelerator mentioned in multiple email examples for credibility
• Uber - Social proof reference in smoothie company email
• Fitbit - Social proof reference in smoothie company email
• GoPro - Social proof reference in smoothie company email

Concepts & Frameworks:

• The Manual-First Approach - Learning through personal execution before scaling with automation
• Founder Credibility Advantage - Why CEO/founder emails get higher response rates than employee outreach
• Template Personalization Psychology - Using exclusivity language and conversational tone to make mass emails feel individual
• Targeting vs. Execution Trade-off - How perfect targeting trumps perfect writing every time
• Before & After Email Analysis - Systematic comparison of failed vs. successful cold email approaches

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