Emails that feel insincere can erode trust and harm your outreach efforts.

'I honestly look at this message and I'm like, well, this guy's full of shit, like I'm not going to, like, this is the most clear example of a um of a false, um. I want to use the word like opposite of genuine, like ingenuine like starting point, you feel the same.'

Takeaway:

• Avoid insincere or forced personalization.
• Build genuine connections to establish trust.
• Authenticity is key in effective email outreach.

Focusing on key points can make your cold email more effective.

'This could be twice as good if they said half as much.'

Takeaway:

• Keep your emails concise and to the point.
• Avoid unnecessary details that dilute your message.
• Respect your recipient's time with clear, concise communication.

A confusing or unclear message can lose your recipient's interest quickly.

'At this point in my read through, I'm about, you know, 40 seconds in, and I'm like, spit it out. What, what are we doing here, guy?'

Takeaway:

• State your purpose early in the email.
• Avoid long introductions that hide the main message.
• Clarity helps maintain the recipient's attention.

Providing immediate value can pique interest and encourage engagement.

'So please, if you're listening to this and you have an option to do a, you know, a gimme for, for your, your list, um. I think of it like people just signed up for a trial, but you're just making it dead easy for them.'

Takeaway:

• Consider offering a free trial or sample to showcase your value.
• Make it easy for recipients to experience your product or service.
• Value-driven approaches can lead to higher engagement rates.

Overemphasis on hyper-personalization might distract from the main message of your email.

'And you're wondering like, you know, should I go for personalization or hyper, like I think you're focusing on the wrong thing. So a little bit of personalization is good as Jack said, like, just like, is it really for me?'

Takeaway:

• Don't let personalization overshadow your core message.
• Ensure personalization serves to enhance, not detract.
• Focus on delivering value to the recipient.

Certain writing styles or punctuation can reveal AI-generated content, reducing trust with your audience.

'Jeremy and I's inside joke, cause you can find out if AI wrote something by, uh, did they write use a double hyphen. This is a single hyphen, but for some reason, ChatGPT, Claude, Grok, they tend to default to this double, and that's a kind of a dead giveaway.'

Takeaway:

• Be mindful of AI writing patterns that may seem unnatural.
• Edit AI-generated content to match human writing styles.
• Maintain authenticity to build credibility with recipients.

Personalization is key in email marketing, but overstepping boundaries can harm your outreach efforts.

'I think for me the big mistake was this stuff that are like borderline personal that you wouldn't bring up. Like it's fine to say, Jack, I know you love backgammon, that's great. But Jack, you're playing backgammon with your wife. It's like one step too far, you know, it's like the human will pick that up.'

Takeaway:

• Keep personalization relevant and professional.
• Avoid discussing personal relationships unless appropriate.
• Subtle personalization can be more effective than overly detailed.

Without a clear Call to Action (CTA), your cold emails may leave recipients confused about the next steps.

'We didn't talk about the CTA, but do you want to see the output of research done on you and your company? Like, that's not bad, but again, I kind of already got it.'

Takeaway:

• Ensure your CTA is clear and actionable.
• Avoid assumptions that the recipient understands your offer.
• A well-crafted CTA guides the recipient toward the desired action.

Relying heavily on AI-generated content can make your emails seem inauthentic and off-putting to recipients.

'There was something here, but it's like this philosophy was, let's gather every tidbit from the board game they mentioned on a LinkedIn post to a client they referenced in 2013. I'm not kidding. It was 2013. And so, let's shotgun all this stuff and use that to our advantage. I'm like, you know, you just muddied the water. And if anything, like, made it a little bit creepy.'

Takeaway:

• Use AI tools to enhance, not replace, genuine communication.
• Be cautious about overloading your emails with excessive personal details.
• Maintain authenticity to build trust with your recipients.

Over-personalization in cold emails can make recipients uncomfortable and distract from your main message.

'I'm not sitting here saying like, first line personalization is dumb. I don't think it is, but that's not the point of doing outreach is to show people how much research you did. You're using it to say like, this message is for you, and I don't need you to tell me that you love Monopoly and you fight viciously with your fiance because of the board game and you want other guys to back you up like. Calm down, you know, it's like you're trying to pitch me something.'

Takeaway:

• Avoid sharing overly personal details that may make the recipient uneasy.
• Focus on relevant personalization that connects to your message.
• Keep the personalization concise to maintain the recipient's attention.