Confessions of a Serial Salesman by Steve Nudelberg

Confessions of a Serial Salesman, Interview with Author Steve Nudelberg

This week’s guest has to be my favourite of all. He’s my Cuban coffee in the morning that gets me going.

We invited Steve Nudelberg back onto the show to talk to us about his new book, “Confessions of a Serial Salesman: Rules of Engagement for Leaders and Influencers,” and what we can learn from it.

Steve Nudelberg is a serial salesman & entrepreneur. As a product of his entrepreneurial spirit, he developed On the Ball – a company that focuses exclusively on sales & business development. Inspiration for the company name was derived from the feedback Steve received from business associates, claiming that he was always ‘on the ball’.

Super excited for what we can learn from Steve this week, so let’s dive right in.

In this week’s show:

  • The importance of relationships to success in sales
  • “Growing to Greatness”
  • How to build relationships
  • Rule number 1 from Steve Nudelberg’s book
  • What other rule in the book gets the most traction?
  • What are people going to learn from reading “Confessions of a Serial Salesman”?
  • Where to get “Confessions of a Serial Salesman” on presale


Steve describes “Confessions of a Serial Salesman” is a way to live your life. He is a student of the game and has been in sales for 40 years, and in putting together this book he gathered the best of the best from the industry to create the ultimate process for successful people.

Steve is proud to have had his son write the foreword for the book – who has lived his life by this process and has seen tremendous success in his career as a college football coach.

The importance of relationships to success in sales

What is the difference between a good business relationship and a good relationship? None.

People who focus on specific aspects of the process of selling are generally the least successful, observes Steve. Especially today when everything is so transparent – people buy you long before they buy your product or service.

If you don’t get along well with a prospect in your first interaction, you’re going to struggle to do business together. But when you do make those good connections, sales is a lot of fun – because the richness is not just the sale, it’s the long term relationship and opportunity to help other people to be successful.

In many relationships, you may not end up getting a direct sale, you may just be a friend or a resource to them. And that can lead indirectly to a sale down the line through referrals. Strong relationships are central to that.

“Growing to Greatness”

In this era of many young people struggling with self-confidence, how do men and women grow great as Steve talks about in the book?

In a world where so much of our work life and even personal life is online, young people aren’t getting hands-on, face-to-face sales experience with retail or sales veterans.

The president of Steve’s company is 30 years old and started in the company at the age of 23 as an intern to learn on the job. That form of training is critical, practical learning that takes time and patience and can’t be replicated with any form of online training.

It is a slow path to mastering the craft.

The way people are being trained now – both young and old – is often in a transactional mentality. The relationships method of selling requires a different kind of training, the basics of which are discussed in Steve’s book.

If you are targeting the C-suite, not having those relationship skills is going to stifle your career progression as those soft skills that have to be learned through experience, are critical to success.

How to build relationships

Learning about people before you meet them gives you the opportunity to find common ground that can be a topic of conversation when you meet.

The longer you are able to have a conversation and enjoy one another’s company without mentioning your product or company, the more likely it is that you are going to be able to do business together.

Finding out where someone went to school, what their interests are, what their sports teams are, you are able to find shared passion and become ‘their guy’, as Steve puts it.

Rule number 1 from Steve Nudelberg’s book

Rule number 1 in Steve’s book, “Confessions of a Serial Salesperson,” is “wake up early.’

Most successful people wake up early, says Steve. Of course, early means different things to different people. But he gives the example of a client he did business with who would send him emails at 3 A.M.

Steve asked him why he got up so early. The client’s reply was that most people consider early to be between 5-6 A.M. and so he figured if he woke up an hour earlier than them he would outwork them by 30 hours per month – another week of work every month over his competition.

Consistently being the first in his clients’ inboxes since that moment has proven to be a huge asset to Steve throughout his career. It says to people who he is and what he is.

There are also very few interruptions early in the morning, which allows him to be very productive.

Steve now wakes up without an alarm between 3-4 A.M. every day. Not everybody has to do this, but even adding 30 minutes to your day, every day, will benefit you tremendously each month.

What other rule in the book gets the most traction?

Rule number 21 – Tell Me Something Good.

This is the number 1 takeaway for many people that Steve has delivered his presentation to on this subject.

People are programmed to meet each other with the phrase, ‘hey how are you?’ The response to this question is often very negative as they share their problems with you. And you then have to move from a negative start to the conversation to a positive one.

Steve asks, why do that? He’s reminded of the Chaka Khan song ‘Tell Me Something Good,’ and instead starts the conversation on a positive note. It’s a fantastic conversation starter that gets things off on the right food in the right frame of mind.

You want to be able to make people feel good enough that every time they see you they want to be around you so they can feel that good every time. – Chris Cebollero.

What are people going to learn from reading “Confessions of a Serial Salesman”?

The book contains 27 rules of engagement for you to try and see how they work for you.

The two greatest validations of this system are Steve’s son who at 30 has been one of the fastest rising college football coaches and the president of his company who started with him when he was 23.

The greatest athletes in the world have coaches to help them see blind spots. The book is a system based on Steve 40 years of experience in the business that provides a structure to help you observe those blind spots and guide your actions as you develop through your career. It’s a toolbox to deal with the day-to-day rejection of being a sales person and be successful.

Where to get “Confessions of a Serial Salesman” on presale

You can sign up for the book at