Cold Calling: The Uncomfortable Secret Weapon

I’ve seen several email questions come up over the years, but very few about cold calling. And we all know why—it’s uncomfortable.

But here’s the thing: The original premise of search is buying businesses from retiring Baby Boomers, and they still answer their phones. Cold calling might feel awkward, but it’s one of the best tools for searchers.

Why?

• Real Conversations Win: Baby Boomers and Gen X don’t ghost you on the phone like they do with emails, (you might get told to F off sometimes though). If you can get them talking, you’ve got a shot at building real rapport.
• It Makes Your Emails Better: Want to know what works? Practice your pitch a few hundred times on the phone. You’ll learn what people respond to (and what they don’t) without the survivorship bias of email replies.
• Persistence Matters: One call won’t seal the deal. Leave a voicemail, call back, or send a follow-up note. The key is keeping the conversation alive.

Cold calling isn’t glamorous, but it works. Baby Boomers aren’t texting you back, and deals don’t land themselves. So, pick up the phone—it’s uncomfortable, but that’s where the magic happens.