Cold Email Outreach with Jeremy & Jack

Jeremy Chatelaine and Jack Reamer
  • 4.7 (48)
  • MARKETING
  • UPDATED BIWEEKLY

Jeremy Chatelaine, founder of QuickMail.io and Jack Reamer, founder of SalesBread.com talk about the strategies and tactics around cold email outreach. Straightforward, to the point, no fluff for actionable insights to help you succeed with your cold email outreach.

  1. DEC 10

    #411 - Gun to Head" Offer Workshop

    📫 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 copy when it comes to getting cold outreach results The "gun to the head" exercise. starting in fantasy land where you can promise anything just to break writer's block and surface strong ideas How to gradually walk those fantasy offers back into reality while keeping them compelling enough that prospects cannot ignore them The "comfort spectrum" of offers. why feeling slightly uncomfortable about an offer is a sign you are ahead of competitors. plus the all important "stomach test" The difference between product or service deliverable offers and foot in the door offers. including examples like N95 mask outreach during COVID and podcast interview campaigns A live example of crafting an offer to sell a CRM for golf courses. moving from absurd promises to a feasible, high incentive pitch that Jack would actually stand behind How principles from Cialdini and first conversation psychology show up in cold outreach. including why small early commitments massively increase the odds of bigger yeses later This episode is a practical playbook on fixing weak offers so your cold outreach has a real shot at earning replies. Listen in if you want sharper, braver offers that still feel honest and deliverable. About the hosts: Jack Reamer founded SalesBread.com. a lead generation agency that brings B2B companies one lead per day using ultra personal 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 like Deliverability AI and Advanced Stats. Start your trial today here. https://quickmail.com

    16 min

  2. NOV 26

    #410 - Stop obsessing about your subject lines. Here's why.

    📫  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 is just as critical as your subject line for open rates - How to engineer your preview text to create curiosity - The hidden role of sender name and domain credibility in trust - Why vague or buried offers instantly kill engagement - How QuickMail's dynamic "sender name mimic" feature can lift reply rates - The difference between good execution and the right strategy - Why great agencies don't stop at outreach—they make sure clients see ROI This teardown reveals that a high-performing cold email starts long before the message itself. Getting the subject, preview, and sender right sets the stage for every reply that follows. 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. Jeremy Chatelaine founded QuickMail.com — the most performant cold email platform to get replies, with industry-leading features like Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com

    15 min

  3. NOV 12

    #409 - LinkedIn DM Autopsy: Watch us Fix These Common Mistakes

    📫 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

    16 min

  4. OCT 29

    #408 - Josh Braun Shares Sales Techniques That Work

    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, and contractor bids that illustrate the method How to use emotional echoing to make people feel truly understood Why it's better to walk away from a bad fit than try to force a sale  How to tailor your message based on job titles and switching risks What Chris Voss taught Josh about silence, trust, and listening for truth The best cold outreach doesn't push, it creates a moment of reflection. Ask the right question, listen well, and let your prospect talk themselves into the next step. 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

    30 min

  5. OCT 15

    #407 - Selling in a LinkedIn connection request? (2025 Example)

    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 curiosity, pain, and timing in message effectiveness What makes a product demo-worthy based on novelty alone Real-world examples of campaigns that broke the rules and won  The blurred line between "product-market fit" and compelling messaging When list-building and timing matter more than copy itself This teardown shows that even hard rules in cold outreach have exceptions if your offer hits the right nerve. Jack and Jeremy unpack what it takes to earn a "yes" at first touch and how to craft messages people actually want to reply to. 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

    15 min

  6. OCT 1

    #406 - Don't Let AI Cripple Your Reply Rate

    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 personalization has improved and where it still breaks Why buyer awareness of AI is making personalization harder, not easier The evolving role of the first line (and why the PS line might be safer) What makes a smart AI prompt and how to reduce hallucination risk Testing AI-generated personalization vs. handcrafted lines When AI might make sense for high-volume outbound vs. niche campaigns This episode is a no-fluff look at what AI can and can't do for outbound personalization in 2025. Jack and Jeremy break down the tradeoffs, the risks, and where smart filters and prompts can actually help without wrecking your reply rates. 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

    15 min

  7. SEP 17

    #405 - "Came across your profile" and other sales mistakes to avoid

    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 credibility, proof, or a clear ask How to use curiosity properly in cold messages (and when it backfires) Why offering value or reciprocity makes outreach more effective A teardown of a SaaS follow-up email that used a "you never used your free credits" angle The difference between cold, warm, and "lukewarm" outreach (and why lukewarm might be your best audience) How small, specific asks can increase reply rates This episode is a masterclass in cold outreach psychology, whether your leads are brand new or just haven't heard from you in a while.  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

    17 min

  8. SEP 3

    #404 - Transforming Silent Rejections into Profits

    📫  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 and descending offers The psychology behind "foot in the door" vs. "door in the face" techniques Using varied offers (video, guest post, webinar, trial) to maintain attention and add value Why the third ask might get a "yes" even if the first two didn't How to keep leads in your universe (e.g. newsletter, YouTube) even if they're not ready to buy The importance of investing thought into offers, not just copy, during outreach planning This episode is a goldmine for anyone running outbound campaigns and tired of stale follow-ups. Rethink your offers, make your asks more strategic, and turn "no response" into lasting brand engagement. 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

    18 min
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4.7
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Jeremy Chatelaine, founder of QuickMail.io and Jack Reamer, founder of SalesBread.com talk about the strategies and tactics around cold email outreach. Straightforward, to the point, no fluff for actionable insights to help you succeed with your cold email outreach.

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