How to Write Cold Emails That Actually Convert (2025 Guide)

INTRO

This blog is a breakdown of a 1-hour live lecture I gave in Austin, TX to a room full of founders. We covered cold email strategy, messaging frameworks, examples of bad and good emails, and how to identify your Ideal Customer Profile (ICP).

If you’re a founder or new rep struggling to get replies or turn replies into meetings, this is the most actionable breakdown you’ll find. No fluff. Just proven cold email theory that works.

WHAT YOU’LL LEARN

• The goal of a cold email (it’s not what you think)
  
• A 4-part structure for writing killer cold emails
  
• How to identify and target your ICP
  
• What to say in follow-ups
  
• When to scale vs stay manual

WHY THIS MATTERS

Founders today are drowning in tools like Clay, Lavender, and Instantly. But tooling is not the problem. Poor targeting and weak messaging are. We’ve worked with founders who sent over 1,000 AI-powered emails and got zero meetings, then got 3 meetings from 14 manual sends after doing this exercise.

When you understand how to write a cold email that actually resonates, it changes your perspective on .

THE GOAL OF A COLD EMAIL

If you're sending cold outbound, the goal is usually to start a conversation or get a meeting, not to close a deal or make a pitch.

You want to:

• Show them you understand their world
  
• Present a sharp, relevant observation
  
• Offer a point of view or solution
  
• Make it dead simple to respond
  

If the person is very busy or high level, like a VP or founder, your email should be designed for them to disqualify you quickly or say “ok, interesting, tell me more.”

THE 4-PART COLD EMAIL STRUCTURE

Here’s the basic flow we use across all outbound (don't worry, we'll break this down in much more depth):

1. Observation: Prove that you’ve done some research. Show you’re not spamming.
   
2. Relevance: Make it clear why you’re reaching out now.
   
3. Value: Describe what you can do for them (in their language).
   
4. Call to Action: Make the ask. Keep it light. Don’t jump to a 30-minute demo unless it makes sense.
   

Basic Example:

"Hey Sarah, saw your post about launching a new marketplace vertical at [Company] last week. I'm a former marketplace CTO now building AI agents that detect fraud and automate customer conversations. Curious if that's something you're exploring. Worth a quick chat?"

HOW TO IDENTIFY YOUR ICP (EXERCISE)

Most founders think they know their ICP. But they don’t go deep enough.

Here’s how we coached one founder in the room to get there:

Initial Answer: "HR managers at industrial companies hiring contractors."

Follow-Up Questions:

• What kind of industrial companies? (Oil and gas, maritime, construction?)
  
• Within maritime, what segment? (Upstream, downstream, vessel operators?)
  
• What job titles are involved? (HR? Site manager? Ops director?)
  
• Do they hire seasonally? Nationally? Use government contracts?
  

Final ICP: "HR leads at mid-sized maritime companies hiring contract welders for offshore work."

That’s the level of detail you need.

Once you define this, you can:

• Build sharper messaging that is actually specific to your persona
• Customize faster at scale for similar, but different, personas in a matter of minutes
• Position your solution specifically for the persona and their business, not just generically in their 'space'
• Increase open, response, and meeting rates
  

BAD VS GOOD EMAILS

We showed a founder’s real email that got 0 replies out of 1,000 sends:

"Hey {{name}},

{{first sentence personalization}} (Ex. Congrats on the new funding round, etc...)

Before {NEW COMPANY NAME}, I founded {OLD COMPANY NAME}, a marketplace handling 4,000 daily book sales, 10,000 new listings each day (sellers list one at a time!), and 7,000 buyer-seller messages daily, not to mention constantly evolving fraud.

I am building {NEW COMPANY NAME} specifically for marketplace founders and operators, to provide AI agents that tackle these exact challenges.

I’d love to see if there is any potential overlap in the challenges you’re facing at {{company}}. Is there anything that jumps out that you would like AI to do for you?."

Why it flopped:

• Too long
  
• Too focused on the sender
  
• No clear CTA
  
• Vague value - even if I took a conversation it would likely be a fishing expedition that wastes my time.
  

Here’s the improved version that got 3 meetings from only 14 sends:

"{NAME},

Saw you’re growing fast at {COMPANY} and wanted to reach out as a fellow CTO in the marketplace space.

I built AI agents specifically for my business {OLD COMPANY NAME} that handle 7,000 messages per day and automatically detect fraud which have significantly improved our operating margin. I’m looking to better understand if I can productize these use cases with my next venture {NEW COMPANY NAME}.

Given you just crossed 6,000 members, would you be open to connecting in the coming week to explore marketplace specific AI use cases? I’m looking to work closely with a few Beta users (for free) to confirm the product roadmap for {NEW COMPANY NAME}."

Why it worked:

• Specific use case and results (increased operating margin)
• Solving a real PROBLEM, not focused on what AI can do.
  
• Clear ICP match
  
• Timely hook (the raise)
  
• Simple CTA
  

WHAT TO DO BEFORE YOU SCALE

Do NOT automate until:

• You’ve sent at least 25 to 50 manual emails
  
• You’ve gotten replies (even if not meetings)
  
• You’ve honed your ICP and message and are repeatably starting conversations that turn to meetings
  

Once you’ve proven it works manually, use Clay or Instantly to scale to a few hundred, then thousands if you continue to see success. If those hold up, then scale wider.

HOW TO FOLLOW UP

At scale, 80% of meetings are not set on the first email. As a simple starting point, we recommend a 4-step sequence:

1. Email #1: 100 percent custom. Nail the observation and value.
   
2. Email #2 (2 days later): Share a case study or ask a quick yes/no question. Alternatively try a custom video (loom)
   
3. Email #3 (2 days later): Try a new angle or highlight urgency.
   
4. Email #4 (optional): Breakup email — “Am I way off base here?”
   

ACTIONABLE TAKEAWAYS

1. As a founder, you have immediate credibility that sales reps do not have. Use it wisely and to your advantage
2. There is no shame in copying styles/templates if they actually work. If you're struggling, copy the above message from the article and make it your own. More power to you.
3. Aside from showing a prospect you understand their problems, nothing you say about what your product can do matters. Your messaging should be centered around solving their problems, not blindly about what your tool can do.
4. The above 3 steps and article should be able to get you meetings just from the information here alone. If you're looking to build a GTM motion from scratch with direct coaching from me, check out our Founder Led Sales Accelerator.

FAQ
Q: How long should cold emails be?
A: 3 to 5 sentences max. If you have more to say, use a Loom video or attach a PDF.

Q: Should I include a Calendly link?
A: Not on the first email unless your CTA is extremely strong or warm. Ask for interest first.

Q: What if they don’t reply?
A: Follow up 2 to 3 times, then move on or test a new message.

Q: Can I use ChatGPT to write my emails?
A: Yes, but only after you’ve defined your ICP and value prop yourself. Don’t outsource the thinking.

Q: What tools do you recommend?
A: Clay, Instantly, Apollo, and ChatGPT (for research and personalization).
‍
→ Want help writing emails that actually convert? Sales reps should check out our Cold Email Engine built by the #1 SDR Manager in Oracle History. Are you a founder venturing into sales for the first time? Our Founder Led Sales Accelerator is a private cohort with direct 1 on 1 coaching that has generated millions in pipeline for tech founders in 2025 alone.

TL;DR

• Start with a clear, narrow ICP
  
• Write 100 percent custom emails at first
  
• Use a 4-part structure: observation, relevance, value, CTA
  
• Follow up with simple, timely messages
• Don’t automate until manual works