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

"Get a warm intro. This is the most effective way to get people to respond to emails that you're sending to them and you're going to have a conversion rate two to three times what you would get if you were just sending a regular cold email." - Aaron Epstein

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.

Timestamp: [0:01-1:48]

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

"Your goal should be actually to get to the next step in the funnel that's all you should be focused on here." - Aaron Epstein

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.

Timestamp: [1:48-5:43]

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:

"We talk a lot at YC about making something people want and targeting is really all about finding the people that want it." - Aaron Epstein

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

"If you get a text from somebody and you don't know them it can almost feel like an invasion of privacy sometimes." - Aaron Epstein

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

Timestamp: [0:01-7:44]

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

Timestamp: [7:50-8:48]

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:

"You are the brand. The words that you use, the way that you reach out, the level of personalization and the effort and work that you've shown in reaching out to somebody will really stand out to people." - Aaron Epstein

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:

"If you can put your personal cell phone number in there and tell them to reach out to you at any hour of the night if there's anything that they need, that's going to feel like you really care and you're going above and beyond to make them successful." - Aaron Epstein

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.

Timestamp: [8:48-9:53]

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:

"If you have multiple asks or multiple things that you want them to do in the email, it can create a paradox of choice and then this feels hard and overwhelming for the recipient." - Aaron Epstein

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:

"I remember one time somebody sent me an email and in it they had an animated gif of them holding a little whiteboard and it said Aaron... and she's waving to me... that got my attention because it felt like they had done something that was very personalized that probably took time to create." - Aaron Epstein

The Friend Test:

"You really want to write how you talk to a friend. This is super important." - Aaron Epstein

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:

"If you're just swapping out a few words, it's probably not specific enough." - Aaron Epstein

Timestamp: [9:53-14:54]

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

Timestamp: [7:50-14:54]

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

Timestamp: [7:50-14:54]

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):

"If I'm reaching out to somebody and I say, hey I see that you are a man, I also am a man we should do business together, then they're going to be like okay that's a little weird it's a lot of people that are like that." - Aaron Epstein

The Good Example (Uncommon Commonality):

"If somebody reaches out to me and they say, hey we went to the same college and went to class in the same buildings, instantly I'm starting to build a connection with them or I feel like we have something in common and I want to get to know them better and I want to help support them because I know what it's like to be in their shoes." - Aaron Epstein

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:

"Most people are pulling up emails on their phone and if you can make it so simple that they can just hit reply, fire off a quick response, quick click a link, whatever the thing is that you want, they're going to do it right there in the moment." - Aaron Epstein

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

Timestamp: [16:22-17:04]

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:

"Tell your story as the quest to solve the problems for your users and this works especially well if you are solving a problem that you have felt yourself." - Aaron Epstein

The Empathy Connection:

"If you know at your past company you ran into this problem, it was a huge headache for you and now you're building this company to solve it, you should tell the user that and tell them that you're dedicating the next 10 years of your life to build this company to solve this problem that you felt so deeply that you know that they feel too." - Aaron Epstein

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 language that your users use to describe you is almost certainly the same language that's going to resonate with other people just like them." - Aaron Epstein

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

"You're on their time, you're in their inbox and it's not their responsibility to get back to you." - Aaron Epstein

Timestamp: [18:10-19:52]

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:

"Often times people will scan an email, get down to the end and try to figure out what is it they're asking me to do. Is this something that I could take care of right now in just a few seconds or is this something that's going to take more time and effort?" - Aaron Epstein

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:

"If you do all of these things, the good news is you'll be the top 5% of all emails that are sent and it's going to be hard for your recipients to ignore them." - Aaron Epstein

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:

"I've done this in the past I was emailing somebody they weren't responding, send an email subject line 'free donuts,' they opened that one and I went and brought some donuts to their office to get them to talk to me." - Aaron Epstein

The Professional Mindset:

"If somebody doesn't respond don't get angry, don't get frustrated, nobody owes you anything here, just move on. You can check back in in a couple months maybe it's not a problem for them right now, maybe it will be in the future." - Aaron Epstein

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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

Timestamp: [15:01-22:10]

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

Timestamp: [15:01-22:10]

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:

"Hi Aaron, hope all is well, wanted to follow up because I noticed your order processing time could be faster. Our company plugs into your e-commerce platform to pull orders in real time and guarantees all orders are fulfilled and on their way to your customer within one day or your money back."

Why It Failed Spectacularly:

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

"This could have been the most amazingly written, most personalized email and nothing that they could do would make me their customer because the targeting is not right." - Aaron Epstein

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

"This is basically telling me that this is spam, they've added me to some list and now it's my responsibility to get off that list... this is an example of an email that I could not delete fast enough." - Aaron Epstein

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:

"You can see that this is all about the person who's sending it, not about the recipient at all. Basically everything about this email is I, I, I... it's all focused on the person who sent it, not on me the recipient and why I should reach back out to this person." - Aaron Epstein

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:

"Hope you don't mind the cold reach out but saw you also spent time in Van Munching Hall."

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:

"As a quick intro, my co-founder and I are both ex-Googlers working together on a meeting driven task manager."

Strategic Elements:

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

The Respectful Ask:

"I was hoping you might help out a fellow Terp and review my YC app. I've already had a few friends review so it's been cleaned up significantly."

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:

"If you have a few moments let me know the best email to send you the doc and thanks in advance."

Execution Excellence:

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

"This was super effective, I responded to this person when that's something that I very rarely do." - Aaron Epstein

Timestamp: [25:48-27:18]

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:

"I write how I talk, you know it's like 'oh and please don't share any info,' that sort of thing." - Aaron Epstein

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:

"It makes it feel very special for the recipient rather than something that I'm spamming out to everybody and hoping anyone responds to me." - Aaron Epstein

Key Elements:

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

Timestamp: [27:24-29:16]

Before & After: The Smoothie Company Transformation

The Original Email (Weak):

Focus: Company's demo day goal and product features

"Hey, we're in the current YC batch hustling to achieve our demo day goal. Can you forward me to your office manager to chat about trying our delicious smoothies in the office for free in exchange for feedback to improve our product. We got Uber, Fitbit, GoPro and others using us and thought your team would enjoy them too."

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

"Hey [first name], I'm Oliver the founder of Snack Blends from the current YC batch and I'd love to throw a free smoothie party for the whole company team at your office. It's like happy hour but smoothies and free! Are you interested? All we ask in return is for some feedback on the smoothies. Is there an afternoon I can come by to treat your team? Thanks!"

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

"When they started doing this one it almost seemed like a no-brainer for their recipients. Yeah, free smoothie party, somebody's going to come and give smoothies to my team, sounds great." - Aaron Epstein

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.

"If you're trying to automate right out of the gate, you're doing it wrong." - Aaron Epstein

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.

"You the founders should be sending these. People are going to take them way more seriously when it comes from the founders or the CEO much more so than if it comes from some account executive or some intern or some other automated process." - Aaron Epstein

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

"You may be small but that is your advantage because you can give your personalized attention to making these dedicated emails feel special to the recipient." - Aaron Epstein

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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