• Rain Bennett

Ep. 36: Better Selling Through Storytelling with John Livesay

Updated: Nov 28, 2020

This week’s guest is John Livesay, keynote speaker, pitch whisperer, and storytelling expert! Rain and John discuss how to use storytelling to boost sales, make yourself irresistible to clients, and turn case studies into “case stories.” This is a great episode for all you entrepreneurs wanting to learn the best way to pitch your idea or sell your product!



When you think of the word “selling,” what comes to your mind?

Is it a greasy used car salesperson? Or a pushy timeshare representative?

For many of us it is. We’ve turned “selling” and “sales” and “salesperson” into dirty words, but I have a problem with that.

We all are selling something at some point -- whether you’re a startup founder pitching to a funder, an entrepreneur selling his product to a store, a nonprofit raising money for their cause, or an individual interviewing for a job. We all are selling and it’s something we need.

John Livesay has made a career of selling to people. He’s cracked the “selling” code and changed the connotation of the word because he understands people.

He’s not the pushy salesperson because he knows people don’t like that. Instead, his strategy is to tell people a story that pulls them in.

You don’t win Condé Nast’s “Salesperson of the Year” by being annoying and pushy.

You get that kind of recognition by knowing something that others don’t.

Luckily John, AKA “The Pitch Whisperer” is sharing his knowledge with all of us in his latest book, Better Selling Through Storytelling.

“When you tug at people’s heartstrings, you open their purse strings.” - John Livesay

So that sounds great and all, but HOW DO WE DO IT, JOHN??

Don’t worry, my compelling storytellers. He’s got a great answer for you.

John talks about the concept of turning your case studies -- previous clients, customers, or community members that you’ve helped -- into “case stories.” This is something that I know people overlook and neglect.

We have these success stories (as I call them) to tell, but we always get caught up wanting to talk about ourselves or our products in an effort to convince people to buy.

But that’s pushing. John wants us to pull.

When you tell someone a good story, especially one that they can picture themselves in, they are hooked and you don’t have to convince them of anything. They’re already locked in.

You just direct them to where they need to go.

When John reaches that final point -- the desired Call To Action -- he has a simple question that is almost 100% effective if you’ve told the right story.

After I talked to John on the show, I tried it with a potential client.

It landed me my first full day workshop, consulting with a large corporation.

Want to see if it will work for you? Go give this episode a listen!

This one is perfect for all of us (because we all have something to sell)!

If you want to learn how to use storytelling to boost sales, make yourself irresistible to clients, and turn case studies into “case stories,”

listen now!

Some highlights from our conversation:

  • How to turn case studies into case stories

  • How to sell yourself as a whole package

  • How John learned to connect with different types of people

  • Life lessons learned from childhood activities

  • Leaning into unique intersections

  • Working as a Speaker

  • Customizing your talks for different audiences: know their life and struggles

  • Empathy

  • Psychographics & how they can be used in marketing

  • Why John went into advertising

  • Repositioning stories for movie trailers

  • Integrating brands into events

  • John’s story of getting laid off and then coming back with a bang

  • Why you should always leave on a good note: strive to find empathy even in the hardest situations

  • Having to transition from print to digital marketing

  • Starting client conversations with “What if?”

  • Using storytelling to help pitch your ideas

  • Common mistakes people make when pitching

  • How to get people to trust you, in order for them to listen to you

  • People buy with emotion, not logic: your marketing should reflect that!

  • The Ladder to irresistible: how you want clients to see you

  • Why it’s so important for you to understand where you stand with your clients

  • The last step of closing with a client: How to seal the deal

  • How to pull people in with a good story: start with exposition, describe the problem, give a solution, and then give a resolution

  • Connecting ideas to make the story stick

  • Steps to help creators sell content

  • Storytelling in the healthcare industry

  • A Micheal Phelps story - what are you willing to do that your competition isn’t willing to do or hasn’t thought of yet?

AND a special gift from John at the end of the episode!

As always, enjoy!

Peace and Love,



Follow John on Twitter @John_Livesay

Follow John on Instagram @thepitchwhisperer

For more storytelling tips and tricks,

Follow us on Instagram @sixsecondstories

Visit our website

Hosted by Rain Bennett (@rainbennett | Twitter) (

#podcast #thestorytellinglab #storytelling #valuesfirst


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