#412 - Takeaways from the 5 “Can’t Miss” Episodes of 2025
Cold Email Outreach with Jeremy & Jack
Release Date: 12/25/2025
#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
📫 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...
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#404 - Transforming Silent Rejections into Profits
Cold Email Outreach with Jeremy & Jack
📫 Don't miss the best cold outreach tips, join the newsletter - https://quickmail.com/newsletter About this episode (#404): In this episode, Jeremy and Jack dive into a smarter way to structure follow-up emails in cold outreach. Instead of repeating the same call-to-action (CTA) or simply lowering commitment levels, they introduce a sales-letter-inspired approach using upsells and downsells to increase engagement and conversions over time. Key Topics Discussed: Why sending the same CTA in follow-ups is a missed opportunity Introducing a follow-up “ladder” with escalating...
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#403 - How to Win at Outreach When Your Competitors Are Better Than You
Cold Email Outreach with Jeremy & Jack
In this episode, Jeremy from QuickMail and Jack from SalesBread tackle a tough question from a head of growth at a small B2B SaaS company: How do you succeed in cold outreach when your product lacks a clear edge in a crowded market? The two dive into real-world tactics and mindset shifts that can help founders and marketers compete against bigger players even without a flashy differentiator. Key Topics Discussed: The importance of market education and timing when entering a saturated niche Competing on price: the most basic but often effective strategy for early traction Why strong marketing...
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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:
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Why Episode 408 with Josh Brown stood out, and how sales psychology applies perfectly to email and LinkedIn outreach
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The “shoe store” story. How better opening questions create instant rapport and better conversations
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Using empathy in sales, including the power of labeling emotions and what happens when you miss the moment
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Episode 403. How to win at outreach when your competitors are better than you, and why educating the market can be the real differentiator
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Episode 389. The future of sales is organic outreach, and why templates keep dying as personalization becomes the expectation
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Episode 411. The “gun to your head offer” exercise for crafting an offer that feels almost impossible to say no to
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Episode 387. The Black Hole B2B Sales Theory, and the “sales universe” model that helps you prioritize warmer orbits and create gravitational pull
This episode is a reminder that the best outreach wins are usually simple. Better questions, clearer angles, stronger offers, and consistent thinking patterns you can absorb by listening to enough teardowns.
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