#135 · A better way to sell AI automations

youtube ↗Cold Email

Is it normal to receive hostile replies threatening legal action when cold‑emailing marketing agencies, or is this likely just a copy/paste scare tactic?

Getting hostile replies that threaten legal action is uncommon for most cold‑emailers; it’s often just a scare‑tactic copy. The laws governing cold email are intentionally vague, which makes many people avoid it out of fear. In reality, the government goes after large‑scale spammers (think hundreds of millions of deceptive emails) before it would ever target someone sending a few dozen highly personalized, value‑driven emails per day. If your emails are hyper‑personalized, sourced from LinkedIn Sales Navigator, and actually provide value, you’re far down the enforcement priority list. So you don’t need to worry much—just keep your outreach legitimate and valuable.

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Related answers

youtube ↗Cold Email

What are the legalities of cold emailing leads, and how can I stay legally compliant?

Nick explains that most cold emails require an unsubscribe opt‑out and a PO box address for CAN‑SPAM compliance in the USA. He notes the legality isn’t mainly about regulation but about enforceability and downside risk. He points out that millions send cold emails, but the vast majority do so poorly—blasting massive spam campaigns fishing for email addresses or banking details. Enforcement will target those bad actors, not the few sending high‑quality, customized emails with strong offers. He emphasizes he’s not a lawyer and his video isn’t legal advice, adding the disclaimer that someone might misinterpret it as encouragement for illegal activity. He observes that people send cold emails at scale worldwide, and laws like CAN‑SPAM are deliberately vague to push self‑compliance for risk reasons. He concludes by saying to do with that information what you will. He then acknowledges a comment from Tech to Jazz about replacing scrolling with daily updates being the best thing for their media diet, and thanks them.

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youtube ↗Cold Email

I’m getting many replies to my cold emails, but they’re mostly negative (‘please stop’). Does that mean I’m on the right track, or should I just keep refining my offer, icebreaker, and consistency?

Getting replies—even negative ones—means your outreach is working; you’ve cleared the first hurdle. Now focus on turning those replies positive by respecting recipients’ time and crafting an offer that’s a clear, easy‑to‑accept no‑brainer.

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youtube ↗Cold Email

How many follow‑ups do you recommend in a cold email campaign, and does it change if I'm still testing an offer after finding product‑market fit?

I start with two emails in total: one main email and one follow‑up. The reason is to put yourself in the shoes of someone reading a crappy email. Think about how many times you’ve opened a pitch email, marked it as unread, or ignored it. If the email isn’t good, a follow‑up makes the recipient far more likely to mark it as spam—about 100× more likely after the first follow‑up and a thousand times after a second. The number one thing we’re trying to avoid in cold email is being marked as spam. So, before you know your copy is good, do not add more than one additional follow‑up, spaced about 48 hours apart. Once your copy is acceptable—say a 3 % reply rate or a 0.5–1 % positive reply rate—you can add more follow‑ups. Adding them will raise your total reply rate, though the proportion of positive replies may drop, the absolute number of positive replies will still increase.

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