How Jim Masiello Faced the Big Banks and Won

In a world where success is often equated with privilege, Jim Masiello and his story stand out. Starting from humble beginnings, with nothing but hard work, grit, and determination to rely on. Today, he is the former founder, chairman & CEO of Alliance Holdings, parent company of Satellite Agency Network, and Strategic Insurance Agency Network (SIAA), a national network of over 5000 Independent Insurance Agencies. Jim is also the founder of successful Masiello Group entities including Financial Services, Insurance, Real Estate, Commercial Leasing, Real Estate Development, an Employment Agency, and an American Express Corporate Travel Agency. Jim’s inspiring journey is chronicled in his memoir, Screw U. In this interview, we dive into the details of Jim’s life and career and learn what made him into the success story he is today.

Tell us about your book.

Screw U: A Memoir is based on factual situations that occurred involving negative and belligerent relationships with banks, the Internal Revenue Service and IRS asset attachment. It includes the inspiration that led to the founding of SIAA (Strategic Insurance Agency Alliance), comprised of 5000 Independent Insurance Agencies that grew into the largest National Insurance distribution network and has remained the number 1 model since its conception in 1983.

What is the PRIMARY benefit, above all others, that your potential reader will gain from reading this book?

In the early 1980’s, independent insurance agency companies were engaged in what is known as a “hard market”. Companies were not appointing many smaller agencies, were raising rates, and actually cancelling smaller more rural agencies and/or seriously restricting what type of exposures existing smaller agencies could insure.

The front cover of Screw U: A Memoir by Jim Masiello“BIG IS BETTER” became our marketing motto simply because our member agencies were paid above average commissions and entered into the SIAA company relationships with competitive insurance companies, wherever they were located.

Also, during this time the U.S. Tax Code was undergoing business-unfriendly changes that affected how businesses reported income and investment asset treatment. The result of which ended up with many small businesses unable to pay taxes based on the changes to the code, especially to assets and depreciation. Smaller agencies were being forced out of business. They needed to grow into much larger premium writers or join a much larger regional insurance organization!

The Masiello Insurance Agency developed a plan to bring only 10% of smaller more rural agencies into the organization. These agencies had to meet certain criteria, be financially solvent and committed to wanting to grow. A highly entrepreneurial model was put in place that allowed Masiello to invite agencies to become “producers.” But, they had to be located in the more rural areas and would not be housed within the Masiello offices, thus the name given to this profit center was “Satellite Agencies”.

If you had to compare this book to any other book out there, which book would it be?

Made In America by Sam Walton, the founder of Walmart

Sam’s quote, “My role has been to pick good people, and give them the maximum authority and responsibility.” This was my operating model! “You can make positives out of most any negative if you work at it hard enough.” This was the single most valuable statement in the book. I’ve always thought of problems as challenges and welcomed opportunities.

On my desk for over 40 years is a plaque that says “In the middle of any difficulty, there is opportunity.” This was my guiding light. I had to deal with bank and IRS harassment issues at the same time that I was developing our tremendously successful SIAA National Insurance program.

Hundreds of thousands of books come out every year. Why should someone buy THIS book? 

The book has a very successful ending. But still talks about the negative situations to overcome. It shows the negative side of dealing with belligerent and incompetent banks, and the high success of the entrepreneurial SIAA, both of which were occurring at the same time.

Who is your target audience?

Anyone that needs to understand the sacrifices an entrepreneur has to endure, negative and positive in detail. My business philosophy is simple; success is a journey and not a destination!!

Did your environment or upbringing play a major role in your writing and did you use it to your advantage?

A photograph of author Jim MasielloI grew up in the poorest part of our city (I became the youngest mayor at age 31), living behind a small side street Italian products grocery store. To help my parents, I worked in the store.

From 8 years old work ethic was instilled in me. I went to a small business college and had to work in the cafeteria so I could eat. Then, I would thumb an 85 mile round trip so I could drive taxis Saturday nights.

I just knew that I did not want to live my life in an environment like I was brought up in, I wanted a lot more and had the work ethic to achieve. There were many bumps in the road but perseverance best describes my character!

Tell us your most rewarding experience since publishing your work.

Brought lots of memories of my journey to share, mostly with family and friends. The process provided a hell of a look back! In retrospect, it is one hell of a factual entrepreneurial story!

How would you describe your writing style?

Usually straight forward; no mincing of words. Identify issues and resolve them irrespective of opposing positions.

Are your characters pure fiction, or did you draw from people you know?

The book is strictly void of ANY fiction!

Are you more of a character artist or a plot-driven writer?

Factual driven–life for me is too short for fiction in my world!

What do you hope to accomplish with your book other than selling it? 

My success has not been without difficulties that had to be overcome! The story of Screw U needs to provide the reader with knowledge that hard work pays off and there are few obstacles that cannot be overcome!

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