Jack Howley

Jack Howley is an entrepreneur, financial advisor, and expert in assisting corporations and individuals in meeting their wealth creation and protection objectives. Jack spends his time between Naples, Florida and Rumson, New Jersey. For over four decades, Jack has been a successful financial advisor and a leader in his field, representing the top 1% of the industry. After college, where he studied finance & marketing, Howley was looking for a career that would provide meaning and fulfillment in his life, but even more importantly, he was looking for a purpose in life. A fateful meeting with a man named Al Ferrara helped push him towards the insurance and financial services industry.

Jack opened his own firm, Howley Financial Group, in 1986, focusing on a comprehensive approach to protecting families’ finances. Recognizing that most clients he was meeting with had a set of micromanagers in their lives, including accountants, stockbrokers, bankers, and investment advisers, Howley’s business model was built around integrating all those facets together. Howley’s firm works with his client’s investment advisers in order to achieve optimal efficiency in meeting the client’s wealth creation and protection, retirement, insurance, and estate planning objectives, making the complex world easily understandable and transparent. He achieves this through a financial model outlining 27 different areas focusing on protection, savings, and growth in what he refers to as “an MRI of money”. The goal is to have their money work as efficiently and effectively as possible, to minimize taxes, and also protect all the wealth that they’ve accumulated against countless wealth-eroding factors. Howley loves the business that he made his life’s work. He loves helping people and enjoys the satisfaction of improving others’ lives through his work.

Where did the idea for Howley Financial Group come from?

Well, the idea for the name of Howley Financial Group did not require too much intelligence or creativity. I just created a Financial Group and put my name on it. I went out on my own back around 1986, because I was never comfortable in the corporate marketplace. I wanted to be an entrepreneur and have my own hours. I was willing to work many, many hours, to start early and finish late, and I didn’t want to be in a cookie-cutter type of environment. I looked at how the majority of my clients ran their affairs and I wanted to be like them. They were small, closely held corporations and small business owners, and I respected their work acumen. I modeled them as much as possible.

What does your typical day look like and how do you make it productive?

I’m usually up fairly early. I work out in the morning and stay on top of the news in all its aspects, looking at anything from investments and politics to sports and entertainment so that I’m knowledgeable as I speak to people throughout the day. I want to know a little bit about as much as possible so that I can relate to them and their lives. My business world starts at around 8:30 in the morning and goes till maybe 7:00 pm. I usually try to work as many half days as possible, like an 8 am to 8 p.m. kind of thing. Everybody tells me I’m working too hard. But I’ve been working half days for decades. It takes people a few seconds to figure it out when I put it like that, but it is literally half a day that I’m in the habit of working. It’s only twelve hours, but I love it. I love what I do and I’m on the phone with a lot of people. We now have multiple Zoom meetings every day. That’s my typical day and then in the evening, I’m eating with my wife, and then we go out on weekends. We’re typical of most people.

How do you bring ideas to life?

That’s our job, isn’t it? To bring ideas to life. My associates and I are in the financial services business and we have to be the best at it. My typical interview with a client might be two to three hours long, with the first hour just listening and obtaining a clear understanding of their objectives, both short-term and long-term, their assets, their liabilities, and what their personal and professional goals are. The second and third hour is providing advice on how to have them best achieve that. That’s something we have to be very good at because clients typically have sort of a “junk drawer” approach to their financial world. It’s not integrated. It’s not coordinated. Their portfolios are very confused in many cases. They’ll have IRAs over here and mutual funds over there and 401ks over here and bank notes over there.

We try to integrate and coordinate their assets so it’s working almost like a symphony orchestra, so that they’re working together in a very integrated and coordinated fashion that creates an optimal amount of wealth and minimizes tax. We take each of their assets and I share my expertise on how those assets can perform more efficiently and effectively by using a macroeconomic approach in their planning so that they work together with the other assets rather than separately. Many of my clients have been trained by financial institutions to think very micro and very separate. We’d like them to do the exact opposite and have them all work together. We find from our experience that by having them work together often, they’ll have more efficiency, effectiveness, and fewer taxes. They’ll have more protection and they’ll be in control of their money rather than relinquishing control to the financial institutions and the government.

What’s one trend that excites you?

People have historically saved too little. What I’ve been reading is that as a result of COVID people are saving more because they’re not spending it. They’re not going out as much, they’re tightening their belts a little. That’s a good thing because people have a tendency to spend much more than they should. It also helps people in a psychological sense, it makes people feel good and more confident about the future when they have more money they can see is in the bank.

What is one habit of yours that makes you more productive as an entrepreneur?

I’m very organized. To be an entrepreneur, you have to have a very efficient organization so that you’re always on top of, not only the latest trends and tax laws, but also the everyday work you do that’s necessary to making sure that my clients’ interests are paramount. Whatever their goals are, my main objective is to make sure that they’re accomplishing them in the most efficient way possible through some of my recommendations or contacts. Keeping the organization of that process smooth and continually updating my understanding of what my client’s needs and goals are, is one of my best habits.

What advice would you give your younger self?

Stay organized, work very hard, always educate yourself, and stay on top of everything regarding your industry so that you become an expert at what you do you. You want to be the best at it so that you can provide the best advice possible to make your clients’ lives better.

Tell us something that’s true that almost nobody agrees with you on.

I’m always reinforcing the importance of the simplicity of just saving money, and that’s more important than the products they’re going to buy. A lot of people are focusing on the return they’re going to receive on their assets, as if that’s the only metric that really matters. Well, a 60% rate of return on nothing is 0%, while a 0% return on something is still at least something. Saving money is more important than the return you’re going to receive on it. Of course, the ultimate is to have both, to save money and get a good return, which through my macro process is what we help clients do.

Another thing is I always like to look at qualified retirement plans. Let’s say people put their money in 401ks and IRAs and they always think they’re saving taxes. I always tell people that there’s not a qualified retirement plan in America that saves taxes, and they think I’m crazy. People are putting their $19k every year into a 401k and they think they’re saving $6k in taxes. They may be currently saving tax, but then that money is locked up until they’re almost 60, and they’re still going to pay taxes on it. That $19k would have grown to $60k and now they’re going to be paying $20k in tax and only saved $6k. They’re really thinking that they’re saving taxes and I’m just trying to make them aware that they’re just postponing tax.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

There is no substitute for hard work. It sounds very simplistic, but I think a lot of people aren’t working that hard today. They want instant gratification and they’re not looking at the long-term effects of that, especially a lot of the single people. They don’t realize the responsibilities that they have ahead and they’re living for today. Then they get married, they start a family, they buy a house, and all of a sudden, they’re in their late thirties and in many cases they probably regret a lot of the habits that they had in their late twenties. They could have made their life better in their thirties and forties by having a different perspective. When they start too late, it’s going to be very difficult to recover. Starting early and working hard towards financial security is something few people would ever regret.

What is one strategy that has helped you grow your business?

Probably the number one reason for the growth of my business is clients being very happy with my advice and them being kind enough to refer me to their friends, family, and business associates. They want to share this very unique process with other people. They understand that the solutions that I give them focus more on the process and strategy of how money works versus the products. I think most people who are in my business are focusing on products while I focus more on the process. I’m focusing on the golf swing and they’re focusing on the clubs. I tell clients they can keep their current clubs, let’s just take golf lessons.

What is one failure you had as an entrepreneur, and how did you overcome it?

Like any successful athlete, a successful entrepreneur experiences multiple failures every day. The greatest hitter of all time was Ted Williams and he failed 60% of the time. There have been so many failures for me, but if you don’t fail, you’re not growing. I think putting yourself in an uncomfortable position on a consistent basis is how you grow. It’s very easy to stay in a very comfortable area, and if you do, you’re not going to fail. We can repeat third grade forever and we’ll never fail, but if you don’t put yourself in an uncomfortable position which allows you to grow, then you’re never growing. You’re rotting.

What is one business idea that you’re willing to give away to our readers?

The only business I have is this business which is I think is the greatest business of all. It gives you a tremendous amount of satisfaction in knowing that the people that I have come across throughout my professional career are better off after they’ve met me than before they met. That that gives me tremendous satisfaction. It’s not an idea, it’s just a passion for what you do, and I think a lot of people go through life maybe never having a professional passion.

I’ve been very, very fortunate in that I entered this industry and I’ve always had passion for it because this is real life. We’re dealing with things that that affect people’s lives in a very, very, very, very important way. My recommendations affect how their children are going to be educated, whether they’re going to pay off their mortgage, whether they’re going to retire successfully, and whether they’re protected in the event of death, disability, or lawsuit. There are so many complex ideas and reasons and they’re just going to be in a better place and have that ultimate financial peace of mind which gives me peace of mind. If I had to start over, I would do the same kind of work because I love how much good I can do for people.

What is the best $100 you recently spent? What and why?

On a nice bottle of wine! My wife and I bought a bottle of Caymus and had some laughs.

What is one piece of software or a web service that helps you be productive?

I am the most non-technological person you’ll ever speak to in your life. As great as technology is, I think it’s had a lot of negative impact on people because they hide behind their computers and iPads and they’re hiding behind numbers rather than trying to relate it to what their clients’ goals are. Clients want to know that you’re human and that they can speak to you and talk to you and cry with you and laugh with you and share their life with you, so I’m not going to be hiding behind that software. I think the experience that we provide clients, which I think is unparalleled, is all about people and caring and being sympathetic and being understanding of their short-term and long-term objectives rather than some software program. So, to answer the question, I’ll say my cell phone because it helps me keep in personal touch with all my clients.

What is the one book that you recommend our community should read and why?

From a financial standpoint, I recommend two books that I give out to my clients. One is called Missed Fortune 101 by Douglas R. Andrew and the other one is called Leap by Robert Castiglione. Both books reinforce the various macroeconomic financial strategies that that we employ in assisting our clients and meeting their objectives.

What is your favorite quote?

I don’t have too many good things going on, but people seem to respond to the stuff that comes out of my mouth when I’m on a roll. I sort of laugh myself because I thought it was funny, though sometimes I’m the only person laughing! But I think my quote about “It’s the swing, not the clubs” is something that people can appreciate. Or if I know the client’s a baseball fan, I’ll say “It’s the swing, not the bat.” That statement sounds simple, but it has a lot of meaning. It may make someone go, “What is this guy talking about?” But when you analyze it, I simply mean the products you buy are not that important. You’ll be buying products from now until the day you die, but how you buy them is more important than what you buy.
I think that’s important so that they realize that the process and the strategy is more important than the products. I always talk about how this is “The Howley Experience.” This is an experience. If this is just a good idea or a few good ideas, big deal. You can get a few good ideas from a lot of people. I tell clients this will be the greatest two hours of your life. Other than the birth of your children, there nothing more meaningful since what we’re going to be reviewing life changing.

Key Learnings:

• Our financial services are very unique, focusing on a macro view of our clients’ finances
• It’s not enough to have a great castle. You must have a strong moat around it for protection.
• A stable financial life in your forties and fifties begins by taking steps in your twenties and thirties.