#409 - LinkedIn DM Autopsy: Watch us Fix These Common Mistakes
Cold Email Outreach with Jeremy & Jack
Release Date: 11/12/2025
#414 How the Pros 2X Their Sales Meetings (No Extra Prospecting)
Cold Email Outreach with Jeremy & Jack
đź“« Don't miss the best cold outreach tips and cold email tactics, join the newsletter - About this episode (414): In this episode, Jack and Jeremy share practical ways to boost booking rates when handling warm leads from outbound campaigns. They walk through simple habits and tactics that help you reply faster, cut friction, keep momentum high, and ultimately get more prospects to show up to the calls they requested. The conversation focuses on what really moves the needle once someone raises their hand and how small tweaks in your follow up can dramatically increase conversions. Key...
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#413 - Fix any campaign with 2 simple changes
Cold Email Outreach with Jeremy & Jack
đź“« Don't miss the best cold outreach tips and cold email tactics, join the newsletter - In this episode, Jack and Jeremy tackle a simple but powerful question. If you could only pull two levers to improve a cold outreach campaign, which ones would produce the biggest lift in both reply rate and ROI? What starts as a theoretical exercise turns into a deep breakdown of strategy, list quality, offer strength, and how to diagnose a campaign that is getting crickets. The hosts compare notes, challenge each other, and map out which levers matter most depending on the situation. Key...
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#412 - Takeaways from the 5 “Can’t Miss” Episodes of 2025
Cold Email Outreach with Jeremy & Jack
📫 Don't miss the best cold outreach tips and cold email tactics, join the newsletter - About this episode (#412): Jack and Jeremy do a laid back end of year “water cooler” recap of the episodes that hit hardest in 2025. They revisit the moments they still think about, from sales psychology and empathy to offer creation and a new way to visualize prospecting, plus a quick trip down memory lane with the outreach email that helped kick things off back in 2017. Key topics discussed in this episode: Why Episode 408 with Josh Brown stood out, and how sales psychology applies...
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#411 - Gun to Head” Offer Workshop
Cold Email Outreach with Jeremy & Jack
đź“« Don't miss the best cold outreach tips, join the newsletter. https://quickmail.com/newsletter About this episode: Jack walks Jeremy through his "gun to the head" exercise for building irresistible offers in cold outreach. They explore why most campaigns suffer from weak, boring offers and how to move from ridiculous fantasy promises to bold, realistic offers that actually get replies. Along the way, they break down concrete examples and the psychology behind what gets someone to respond to a first message. Key topics discussed in this episode: Why offers are often more important than...
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#410 - Stop obsessing about your subject lines. Here’s why.
Cold Email Outreach with Jeremy & Jack
📫 Don't miss the best cold outreach tips, join the newsletter - https://quickmail.com/newsletter About this episode (#410): In this episode, Jack and Jeremy tear down a cold email that opens with the line “No one likes a cold email.” They explore why this approach fails to stand out and how small details in your inbox preview can make or break your open rates. The conversation turns into a masterclass on subject lines, preview text, and how the overall “look” of your message shapes trust before anyone even clicks open. Key topics discussed in this episode: - Why preview text...
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#409 - LinkedIn DM Autopsy: Watch us Fix These Common Mistakes
Cold Email Outreach with Jeremy & Jack
📫 Don't miss the best cold outreach tips, join the newsletter - About this episode (#410): Jeremy and Jack are back in the studio breaking down a pair of cold outreach messages, including one that went viral on LinkedIn. They explore what worked, what didn’t, and how small tweaks in tone and structure can make a big difference in response rates. The episode dives into writing conversational, curiosity-driven messages that actually open doors on LinkedIn. Key Topics: Why starting a cold message with a question can be risky but sometimes effective The problem with jargon and why clarity...
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#408 - Josh Braun Shares Sales Techniques That Work
Cold Email Outreach with Jeremy & Jack
About this episode (#409): In this episode, Jack and Jeremy sit down with sales legend Josh Braun to explore how to start smarter, more effective cold outreach conversations. They break down Josh’s “poke the bear” method, a way to uncover hidden pain points without triggering resistance, and share practical tips for making prospects pause, think, and actually want to talk to you. Key topics discussed: Why cold outreach fails when it starts with pitching or convincing How to “poke the bear” by asking questions that expose invisible problems Real-life examples from malls, car washes,...
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#407 - Selling in a LinkedIn connection request? (2025 Example)
Cold Email Outreach with Jeremy & Jack
About this episode (#407): In this episode, Jack and Jeremy break down a bold connection request on LinkedIn that skips the usual small talk and goes straight for the pitch. They debate whether this “go for the kill” approach ever works in cold outreach, and if so, under what conditions. Along the way, they define a framework for when pitching in a connection request might actually make sense and when it’s still a terrible idea. Key topics discussed in this episode: Why most people shouldn’t pitch in a connection request The rare exceptions where a direct pitch can work The role of...
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#406 - Don’t Let AI Cripple Your Reply Rate
Cold Email Outreach with Jeremy & Jack
About this episode (#406): In this episode, Jack and Jeremy revisit the question: should AI be trusted to write and send first-line personalization in cold outreach? It’s late Q2 2025, and AI tools are smarter than ever. But are they smart enough to handle something as nuanced (and reputation-sensitive) as email intros without human review? The guys go deep on how far the tech has come, what’s still risky, and where it might actually make sense in your workflow. Key topics discussed in this episode: Why letting AI send unchecked intro lines is still a risky move How the quality of...
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#405 - “Came across your profile” and other sales mistakes to avoid
Cold Email Outreach with Jeremy & Jack
About this episode (#405): In this episode, Jack and Jeremy run a two-part teardown of real cold outreach messages. They start by analyzing a LinkedIn message that pitches AI agents for lead generation, then break down a clever follow-up email from a SaaS tool the recipient had signed up for months earlier. You’ll hear what worked, what didn’t, and how to write outreach that actually gets replies, whether your audience is ice cold or just cooling off. Key topics discussed in this episode: Why vague or generic subject lines instantly signal cold outreach - The dangers of pitching without...
info_outlineđź“« Don't miss the best cold outreach tips, join the newsletter - https://quickmail.com/newsletter
About this episode (#410):
Jeremy and Jack are back in the studio breaking down a pair of cold outreach messages, including one that went viral on LinkedIn. They explore what worked, what didn’t, and how small tweaks in tone and structure can make a big difference in response rates. The episode dives into writing conversational, curiosity-driven messages that actually open doors on LinkedIn.
Key Topics:
- Why starting a cold message with a question can be risky but sometimes effective
- The problem with jargon and why clarity always wins
- How to use the CCQ framework (Compliment, Commonality, Question) to personalize outreach
- Rewriting a LinkedIn message to sound more natural and human
- How to balance curiosity with clarity in a short LinkedIn connection note
- The difference between opening a conversation and selling right away
- How strategy and product positioning tie directly into outreach campaigns
This teardown shows how small writing decisions shape your outreach success. Whether you’re writing LinkedIn DMs or cold emails, the goal isn’t to pitch, it’s to connect.
About the hosts:
Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/
Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com