Anyone who’s followed Derek Halpern’s Facebook page over the last couple of years has read numerous amusing anecdotes from his coffee shop escapades.  It’s not the fact that interesting things happen to him…it’s that he’s great at telling the story.  A master copywriter, we chat about being unemployable, being irritated in the world, some of the best resources for old-school advertising, and how to pinpoint your customer with your copy and narrative.


I initially interviewed this week’s guest in Episode 15 (September 2013), where we spent an entire hour discussing the psychology of sales and storytelling. Today, Derek Halpern of Social Triggers is back with an explanation of the three kinds of customers and how to sell to each one, why you need to be authentically you—but not too much—and on general guidelines for sharing your story in a way that invites the customer in to connect with you and what you do.

“Storytelling – whether it’s print copyrighting or captivating a room, an audience, or a dinner table, is key to building relationships.”


3:20 – Michael recently had breakfast with Larry King and Cal Fusman from Esquire, masterful storytellers and feel our guest is the equal of these two men in storytelling.

6:24 – Derek’s gift is articulating the angst as part of the story.

8:10 – Jerry Seinfield as entrepreneurial icon.

14:25 – You always want to be polite, and Derek feels that in New York, in these coffee shops, people are throwing polite out the window. Open doors, help people putting bags in overhead bins on airplanes. Be that person.

18:10 – You got to be your true self, because being anyone else is so difficult. (Derek)

18:57 – Not sterilizing message could be a detriment to finding customers, but there are ways you can “not be yourself” that would help sales, such as cursing. Some people won’t buy from people who curse, so if you don’t curse online, it will gain you followers.

21:40 – You can’t mix business and politics. He doesn’t feel it’s a good decision. People subscribe to you to learn what you have to teach them. They didn’t subscribe to you to learn about your political opinion.

24:30 – Derek discusses his growing up in a rough neighborhood and that he views this as a benefit because he knows what he’s fighting for.

26:50 – Who influenced Derek’s personality? Mom. Grandma. Crazy dad.

29:55 – Everyone has their story (their ‘stuff’). Those who are the most successful don’t lead with their story.

30:40 – Derek agrees, but there are three times when he will lead with his story.

31:40 – If you want to show people that they can recover from uncrecoverable experiences, so you have to show them your unrecoverable situation.

32:31 – Until the world changes, let’s look at the 1 out of 10 who made it, and be that person. Try to become the outlier.

33:00 – There is implicit permission to share your story when you’re inspiring others, rather than throwing a pity party.

35:25 – Why sales pages convert and how they convert to each of the three different types of customers.

36:10 – Definition of an Informed Customer and why your internal launch rocks.

37:13 – Definition of an Afflicted Customer and why a 50% off sale may not be the best option.

37:56 – Definition of an Oblivious Customer and why they make you work three times as hard.

39:00 – Converting oblivious customers give you a 7+ figure business.

40:55 – Downplay the specificity of what you’re doing to talk to those who may not know what you do.

41:40 – Knowing how to write better copy has helped me overall from a business standpoint and a life standpoint.

42:20 – Where do you start if you want to learn how to write great copy?

45:05 – Address the customer at the stage the customer is in. Lead with your product in an aware market is to lead with the features. If you’re in an unaware market, lead with your promise.

51:50 – Michael’s new course, The Art of the Interview, Launches April 11.
56:15 – Derek discusses his weight loss over the course of the last year and what motivated him.

59:10 – The reasons why Derek is moving back into the public spotlight to be the face of his business.

63:00 – March 22 at Social Media Marketing World, Michael will be talking on the Art of the Interview

Derek’s class:
Michael’s Class: The Art of the Interview

Breakthrough Advertising by Eugene Schwartz

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