Interview with Jeff Costello

1)    Tell us a little bit about yourself. How did you get into writing?

I’m a long-time sales executive in the technology space. That’s how I’ve made a living for the past 30-plus years. But, deep down inside, I’m really a storyteller. Whether it’s a presentation to a large group, a barstool conversation with a customer, or just hanging out with friends, I like to tell stories. Usually, they’re humorous. Occasionally, they’re insightful. Sometimes, they’re both. I hope that book falls into the “both” category.


2)    What inspired you to write your book?

There’s a famous quote from Toni Morrison that goes like this, “If there’s a book that you want to read, but it hasn’t been written yet, then you must write it.” I’ve always wanted to read a book that accurately captured what I’ve experienced in my career. I felt that readers would enjoy the people, passion, camaraderie, customer interactions, and overall craziness associated with hitting a revenue goal, chasing the big deal, or being for sale, especially if I did it in a humorous way.

3)    What theme or message do you hope readers will take away from your book?

I hope that readers gain a better understanding of the salesperson-buyer relationship and, hopefully, a better appreciation of it. Business people are almost always portrayed negatively in books, movies, and TV shows, especially salespeople. It’s a common trope to show salespeople as either smart but devious or affable morons. This has not been my experience. I’ve interacted with thousands of buyers and salespeople over my career and have found the great majority of them to be intelligent, honest people.

One other theme that I’d like for readers to see is to always find the humor in things. The characters in my book deal with a lot of turmoil in a short period of time but are always laughing together every step of the way. That should feel authentic to every salesperson I’ve ever met.

4)    What drew you into this particular genre?

I find what I do for a living to be fascinating. I love it and really thought readers who were unfamiliar with my world would love it as well. I confided to friends that I wanted to write a book that described the process of running a sales organization with the same level of passion and detail that Tom Clancy uses in describing the inner workings of a submarine because I think it is every bit as intriguing.

5) If you could sit down with any character in your book, what would you ask them and why?

I want to sit down with Joseph Whitehorn. Every other character in the book is very familiar to me from my years of experience running technology sales teams, so I’ve already had the pleasure of spending time with many similar people.  I find the backstory of Joseph Whitehorn to be fascinating, especially since this year marks the 100th anniversary of the first casualty from the Osage Indian Murders. I love his blend of purpose, focus, and his hidden humor that emerges as the story progresses. 

6)    What social media site has been the most helpful in developing your readership?

As a business person, I have the most extensive following on Linked-in, so that has been the best outlet for me. I also use Facebook and Twitter and would expect those two platforms to grow in importance to me in the future.

7) What advice would you give to aspiring or just starting authors out there?

The two obvious answers are to read more and write every day. That’s the recommendation from every reputable source, and I agree with that wisdom. The best way to get better at something is to do it, so writing daily helps. I would suggest that when you read other author’s work, read with a purpose. Notice the things you like, such as descriptions, dialog tags, POV choices, story structure, etc. Take notes and use them as inspiration for your own work.

Those are the two things that everyone will tell you. Now, I’ll give you some advice that few people will give to you. My book is filled with humor, and I found this advice from Neal Simon quite helpful. I saw him on 60 Minutes, where the interviewer asked him, “Do you laugh at your own work.” He answered that he does the first or second time he reads it, but after that, he doesn’t because he already knows the joke. He remembers it was funny, though, and that is the key. As you proof a chapter for the 50th time, the funny lines are no longer funny to you. You’ll be tempted to pull them or change them. Don’t do that! If it was funny when you wrote it, it will be funny for your readers the first time they read it. That advice may seem blindingly obvious, but when you are deep into the editing process and questioning everything you’ve written, it isn’t.

8) What does the future hold in store for you? Any new books/projects on the horizon?

I just released Surfing with the Bishop and will focus on promoting the next few months. After that, I’ll see what inspires me. I’ve already got some thoughts on future projects but want to get more reader feedback before I lock in on anything.  I do publish a weekly blog called Trifling Amusements on Business and Life that readers might enjoy. To view, check out my website,


About the Author

Jeff Costello served as a senior sales executive for 30-plus years, driving billions of dollars of revenue from emerging technology markets. He’s led worldwide sales teams that supported partners in over 100 different countries and participated in numerous company acquisitions. Having entertained customers for decades, he’s often boasted that he has, “fed more people than Mother Teresa, or at the very least, served better wine.” Jeff lives in the Dallas/Fort Worth area with his wife, Trina, and their dogs, Bentley and Bo. 

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