The Learning Lab

Boston John Responds to shitty Cold Caller

March 8, 2025

Helping elevate the people and profession of Sales by sharing authentic conversations, practical tips, expert advice, relevant tech and real-world lessons from my experience selling every day. Delivered to your inbox every Saturday.

Now that we’re past the launch of my new Membership, I've shifted my attention to an event I’m putting together for the 28th to go see the Broadway production of Glengarry Glenn Ross which I’ll tell you more about in the next newsletter (it’s going to be epic if I can pull this off by the way).

But for this week I was heads-down trying to catch up along with a bunch of client meetings, trainings, podcast recording and more.

Needless to say, I didn’t have much time to write the newsletter this week so here I sit on Friday afternoon trying to think of something meaningful and valuable to write that would be worth your time.

I usually keep a log of things that happened to me throughout the week that I think are interesting or would be good to share but this week I didn't so I had some writer's block to say the least.

That was until I decided to pick up an unknown number from a cold call and that’s when the magic happened and the writing began:)

Instead of breaking it down into the different categories I’m going to just write the story and include the tips and resources along the way.

SALES FROM THE STREETS: Boston John responds to a shitty cold caller

I’m one of those people who actually picks up cold calls from unknown numbers. I want to see if I like the person’s approach and how it works.

Side note: I don’t understand Sales Executives who don’t pick up cold calls or get mad when someone cold calls them but still tell their team to make 50 dials a day. But I digress….

So here I sit with writer’s block, trying to figure out what to write about this week, and my cell phone rings with an unknown number, so I pick it up and hear:

“HEEEEYYYY, BIG JOHN! HOW HAVE YOU BEEN MAN?”

Like he was my best friend.

I knew what was going on, but I still played along and asked who it was and if they knew me.

And then came the obvious answer of “no, but….”

Before he got into his pitch, I cut him off and admittedly was a little pissy with him saying something to the effect of

“Dude, cut the shit with this best friend intro approach. I train sales reps like you and this is one of my least favorite intros because even though it might get them to stay on the phone with you for an extra minute, when they realize it’s a sales pitch they get more annoyed than they would have otherwise. Seriously stop this crap.”

He then explained that it works and tried to justify it by saying that I'm still on the phone with him, etc.

I tried to explain more, but I just got annoyed and hung up.

Then my phone rang again from a similar New York number/location, so I knew it was either him calling back or his boss, so I picked it up again and said

“You calling back for more? Do you actually want to learn how to sell?”

There was silence and I heard whispering in the background repeating what I just said which annoyed me even more so then “Boston John” came out and started calling them a few things I probably shouldn’t put in writing.

The “boss” got on the phone and asked me what my problem was and I explained again, what I do, and why their tactics are the reason people hate sales reps.

I then said “I bet you’re a huge fan of Grant Cardone and Jordan Belfort aren’t you?”

As expected, he answered loud and proud - “Every day baby!”

I then went on to explain why those guys were the absolute worst thing to happen to sales and gave this profession a bad name.

We even started getting into the Boston and New York rivalry of talking shit (which I always love:)

To this kid’s credit, he stayed on the phone with me, asking why I felt that way and explaining how they are in a brutal industry (selling financing solutions), and this is how the entire industry works and what customers and bosses love.

(p.s. Calling someone “kid” is a Boston thing. It has nothing to do with your age)

He then asked me about what I do and went to my website to see who I was.

He tried to boost my ego by calling me a baller but then, to my surprise, was actually interested in learning more.

This softened me up a bit, so my FU attitude dropped a few notches as we started talking more.

To give him credit, he did find a way to circle back to why they were calling and explained that I was on a list of people who had requested funding in the past.

After explaining I had never requested funding he then stopped selling and said that his team was always looking to get better so he was going to check out my podcast and some of my content and wanted to stay connected.

I told him if they ever wanted to learn how to sell without losing their sole to give me a call and then, he ended it by confirming this was my cell phone and asking if it would be ok to send me a text so in case I ever needed funding i would have his number.

He texted me after and I texted back a quick prompt I used to come up with non-douchey sales intro:

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What went from me tearing into a cold caller turned into an actual conversation that ended on a high note.

Here are some of the learning lessons:

  • Don’t try to trick people to stay on the phone with you
  • Try different approaches to find out what works for you
  • When someone is pissed, stop trying to sell them and start trying to learn
  • Always walk away with something (text, meeting, info)
  • Learn something on every call
  • Don’t be a douche

Will I ever reach out to them for funding? Probably not.

Will they actually follow my content and start trying different approaches that are non-Cardoney? Who knows.

But I might have just made a dent and got them to think a little differently.

To the guys on the call today, if you signed up to my newsletter and are reading this now - thanks for the story. I hope you follow through on what you said related to checking out my content and being open to learning.

#MakeitHappen

P.S. This experience reminds me of one of my absolute favorite scenes in Boiler Room (another movie that portrays sales in all the wrong ways but is a great movie).

​https://youtu.be/64cj7Q9c_YA?si=gfGC6kbNn6KqDDS6

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ADDITIONAL WAYS YOU CAN LEVEL UP YOUR SALES GAME ​
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  • The JB Sales Membership is where you’ll get access to my live training, workshops, AMAs and OnDemand catalog so you can level up your sales skills every day! 3000+ Sales pros have already joined. Are you next?
  • The industry-leading Make it Happen Monday Podcast where you’ll get insights and inspiration from some of the most interesting and influential people in the world of Sales and business. (this is where you’ll hear the Guy Kawasaki episode on May XYZ)
  • The JB Sales YouTube channel with practical tips that you can apply immediately to drive results along with interviews and content that is guaranteed to get you to think differently.

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