If there’s a theme to this issue, it’s simple: cold email still works, if you do it with intention. Harry Stebbings landed Marc Benioff after 53 emails, Cold Email Hall of Fame is basically a playbook for writing messages people actually answer, and I sat down with Justin Schenck to break down how we’ve used the same approach to get in front of brands like Disney, Apple, and Goldman.
If you’ve been “dabbling” in outbound and hoping something sticks, this edition is your sign to get serious about structure, persistence, and infrastructure.
📨 53 Emails to Yes: Harry Stebbings’ Cold Outreach Playbook
Harry Stebbings did what most people would quit on: he cold-emailed Marc Benioff 53 times over a year to land him as a podcast guest. The Salesforce CEO eventually said yes and even praised Stebbings publicly for his persistence. But it wasn’t spam. Stebbings relied on a simple, repeatable structure that anyone can use to write cold emails that actually get opened, read, and answered.
Key Takeaways:
- ✉️ Start strong and clear: Use a direct subject line, skip “hope you’re well,” and state your ask within the first couple of sentences.
- 🧾 Show why you’re worth a yes: Add quick credibility with numbers and names (subscribers, customers, notable guests) that prove you are legit.
- 🎯 Make the ask small and specific: Define exactly how much time you need and what for, so saying yes feels easy.
- 🔎 Personalize beyond LinkedIn: Reference real details (favorite drink, recent results, interviews), and use AI tools to uncover those quickly.
- 🔁 Persist without being annoying: Thoughtful follow-ups over time signal seriousness; most people give up long before the yes.
📨 Steal These Cold Email Moves (Legally)
ColdEmails.world isn’t just a fun gallery of messages to Elon Musk and Mark Cuban, it’s a crash course in what actually gets replies. The site breaks down real cold emails that landed jobs, funding, clients, and even responses from celebrities, then turns them into bite-sized lessons you can copy.
Key Takeaways:
- 🧠 Steal proven templates, not guesses: You’re studying actual emails that landed jobs, meetings, funding, and replies from hard-to-reach people.
- 🎯 Every email has a clear job: Whether it’s a job ask, investor pitch, or podcast invite, each example nails one specific goal—not five.
- 🔍 Breakdowns show why they work: The 8-day challenge explains structure, psychology, and small details that flip “ignore” into “reply.”
- 🚀 You get reps without the risk: Instead of learning only from your own misses, you can shortcut the process by modeling what’s already worked in the wild.
🎙️ Goals, Pivots, and Cold Email That Actually Works
I joined Justin Schenck on the Growth Now Movement to talk about how I went from a bright-eyed founder fresh out of college to running Email Outreach Company and living as a digital nomad. We got into why I care more about clear goals than New Year’s resolutions, how we used cold email to land brands like Disney and MasterCard, and what “success” looks like for me now across business, health, and relationships.
Watch/listen to the full episode here »
Key Takeaways:
- 🎯 I’m a goals guy, not a resolutions guy: I set specific targets each year, then stay open to pivots when reality presents a better path.
- ✉️ Cold email is just a connection at scale: To me, it’s person A reaching person B with a clear problem, a relevant offer, and respectful copy.
- 🛠️ Infrastructure is the new “secret”: With inbox limits and spam filters tightening, we win by building serious domain and inbox setups, not by sending more spray-and-pray.
- 🌍 Freedom is designed, not found: Journaling, sleep, and daily movement help me run a growing company while still choosing where in the world I want to wake up.
My Last $.02
If there’s one thing I want you to take from this issue, it’s this: most people lose the game long before the inbox. They either never hit send or they quit after two follow-ups. The people winning treat cold email like a system they can tune, not a lottery ticket.
If you want help building that system, book a free cold email audit, and we’ll walk you through what to fix first. And if you take one idea from this newsletter and ship a new cold email this week, hit reply and tell me how it goes.
Until next time, happy emailing!
Adam