Anthony Pellegrino

Start developing your sense of work-life balance sooner.


Anthony Pellegrino, of Goldstone Financial Group, has dedicated his practice not only to helping individuals plan for their financial future but also remaining by their side as a partner in achieving their desired results. He provides financial plans targeted at achieving consistent, reliable returns regardless of market fluctuations and uncertainties. He does this by putting his clients’ needs first. As a fiduciary, Anthony Pellegrino has a legal responsibility to put his clients’ needs ahead of his own and is held to a higher ethical standard than non-fiduciary advisors.

Anthony Pellegrino and Goldstone Financial Group have helped more than 1,500 clients bridge the paycheck gap during retirement by utilizing accounts with lifetime income features to guarantee earnings and create a paycheck for life. Pellegrino also offers professional asset management through a diverse portfolio of actively managed accounts and securities.

Anthony Pellegrino is seen Sunday mornings on CBS as the co-host of the television show, “Securing Your Financial Future*.” The show previously aired for five years on WLS 890AM radio station, where it was ranked one of the most listened to* financial and economic radio talk shows in Chicago.

Anthony Pellegrino has ranked in the Top 1% of Safe Money Specialists in the nation and was awarded as one of the Top 10 Advisors in America in 2013.** He was also named a Five Star Wealth Manager in Chicago Magazine twice, as voted by his clients and peers. This is a consumer-based award in the financial services industry given to wealth managers in the Chicago area who scored highest in overall client satisfaction. Pellegrino’s growing success led him to share the stage with former President George W. Bush in Washington, D.C., at the Ronald Reagan International Trade Center. He is honored to be recognized as a financial authority in the Chicagoland area. Anthony Pellegrino has passed the Series 65 securities exam and is registered as an Investment Adviser Representative. He also holds an Illinois insurance license.

In his spare time and work at Goldstone Financial Group, Anthony Pellegrino enjoys spending time in the Elmhurst community with his wife and three children. He has a passion for supporting the U.S. military and is an active advocate and sponsor of the USO and Operation Support Our Troops.

*as ranked by Nielsen Audio
**as ranked by Advisors Excel
Investment advisory services offered through Goldstone Financial Group, LLC, an SEC Registered Investment Advisor.

The Five Star Wealth Manager award, administered by Crescendo Business Services, LLC (dba Five Star Professional), is based on 10 objective criteria. The Five Star award does not evaluate quality of services provided to clients and is not indicative of the wealth manager’s future performance. Wealth managers may or may not use discretion in their practice and therefore may not manage their client’s assets. The inclusion of a wealth manager on the Five Star Wealth Manager list should not be construed as an endorsement of the wealth manager by Five Star Professional or Chicago Magazine. Working with a Five Star Wealth Manager or any wealth manager is no guarantee as to future investment success.

Where did the idea for your company come from?

When my business partner Michael and I started Goldstone Financial Group, we did so because we wanted to help people. Back before we entered the market, we noticed that a lot of companies that promised retirement planning solutions only offered generic investment advice. New clients would walk into an advisor’s office, fill out a brief questionnaire, and then receive a cookie-cutter set of investment options. Information wasn’t tailored to the person, and advisors weren’t in a position to give a person the assurance and guidance they needed to build a long-term financial plan. The generic approach was one that worked for a volume-centered investment firm, but it rarely suited the needs of individual clients perfectly.

Michael and I created Goldstone Financial Group as a more holistically-driven firm. We had – and continue to have – four goals. First, we would help our clients design effective income plans so that they would never run out or outlive their retirement funds. Second, we would create an investment portfolio tailored to each client’s needs and preferences. Third, we would help our advisees create a realistic retirement plan. Lastly, we would give clients the guidance they needed to leave a legacy. Our model takes more interpersonal work and effort – but at the end of the day, I know we’re making a difference for our clients.

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

Most of my days are relatively predictable. I start my mornings with a short workout and take a few moments to center myself in prayer and thankful reflection. Then, I head to the office, where I dedicate the first half of my day to meeting with clients and the second half to growing my business. As I move forward, I would like to focus more of my energies on the company – but as it stands now, I deeply value my relationships with my clients. I enjoy spending time working on their cases, and the idea of reshuffling that client-centered portion of my day is a bit difficult to contemplate.

On a slightly different tack, I would say that my calendar keeps me productive. I know that I only have a certain amount of time to complete a task before I need to move on to the next, so I make a point of being as efficient as possible.

How do you bring ideas to life?

I surround myself with a phenomenal team. With all of the media hubbub centered on high-powered CEOs and entrepreneurs, I think it can be too easy to forget about the tireless work that staff members put in to make a founder’s idea a reality. I’m an idea guy myself; I can’t put a number on the times I’ve come up with a business notion in the shower and had to scramble to record the idea on my phone before it slipped away. My team helps me sort through those spur-of-the-moment thoughts and implement actionable plans to bring them to life.

What’s one trend that excites you?

Over the next decade, 78 million baby boomer will be transitioning into retirement. That’s an incredible number; I think Pew put the rate of retirement at around 10,000 people per day. That’s nuts – especially given that a lot of those individuals don’t yet have a clear plan for their life post-career. Soon-to-be retirees need guidance, and my team and I are happy to be there to help them plan for a secure financial future.

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

I can’t say enough about the value of my early-morning routine. I find that working out and spending some time in prayer prepare me for the day in different ways. When I take thirty minutes to exercise, I feel as though I work out the stress and tension that might have lingered from the previous day. Similarly, dedicating some time to prayer helps me clear my mind and center myself for the coming day.

What advice would you give your younger self?

Start developing your sense of work-life balance sooner. Honestly, I feel like overwork is something a lot of entrepreneurs struggle with; business is on our minds almost every waking moment, and that focus can lead us to push off essential aspects of our personal lives. I have an incredible family and a fantastic wife – and I wish I had spent more time with them during those first hectic years. You won’t realize how fast life is going to fly, so you need to enjoy it while it happens.

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

I believe that despite our divisions and heartache, we will emerge from this period of national turmoil stronger and more united than we have ever been before. The hostility we face now won’t stop us from coming together in the end; as low as our national morale is now, I fully believe that we will be stronger and happier in fifteen years. How can we not, with so many great advancements coming down the pipeline? We have AI, and we have innovation; I foresee that within a decade, American businesses and people are going to start thriving.

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

Act like you’re one day away from going out of business. No matter how well Goldstone does, Michael and I never get comfortable or sit back. I guess a part of our philosophy roots in fear – I’ve seen successful businesses fall to pieces, and I know that mine could be next if I stop paying attention. Fear keeps the wick burning, as it were.

The other day, Darren Hardy, the chief editor of Success Magazine, said something that stuck with me. He commented, “Money makes people lazy; success makes people lazy.”

I couldn’t agree more. My advice would be this – keep pushing on, because you don’t know if your ride to the top will crash tomorrow.

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

I always keep moving forward. Here’s how I see it – if you can weigh the positives and negatives of a decision and come to the conclusion that an option is 80% positive, you should go for it. There is no such thing as 100% certainty in business, except that waiting around for a sure bet is guaranteed to stop your growth. It’s okay to take risks, and it’s okay to fail – you have to do both to grow.

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

Looking back, I think my worst failure was trying to make our business suit all types of clients and interests. Some years back, we decided to cast a bigger net and bring in a client base that, in retrospect, wasn’t the best fit for us. Our employees were becoming frustrated, our clients were getting irritated, and it put a pall over the whole office. In the end, I asked a seasoned business owner and friend for advice. He told me to fire every client who wasn’t a fit for Goldstone’s capabilities and interests. The solution sounds shocking, but it worked; we recentered our client base, returned to our roots, and resolved the issue.

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

I recently spent $100 on a pair of Nike all-weather gym shoes, and I really can’t say enough about them. They are waterproof and weatherproof – which, if you live in Chicago, are valuable traits during the winter months. Plus, all three of my sons play ice hockey, so I spend a lot of time stepping in and around water and ice.

If I had to pick a close second, though, dinner at Javier’s – an incredible Mexican restaurant just outside of Laguna Beach, CA – makes the cut. Spending time eating a good meal with friends or family is hard to beat.

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

We could not help clients as efficiently as we do without Riskalyze. It’s an outstanding piece of software that allows our advisors to determine a client’s risk tolerance and assess their potential for risk if the market were to undergo a 2008-esque downturn. We use it daily.

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

I highly recommend “What Got You Here Won’t Get You There” by Marshall Goldsmith. It delves into the problems of becoming too comfortable after experiencing success well.

What is your favorite quote?

I’ll quote Warren Buffet for this one. At a conference earlier this year, Buffett said: “It is insane to risk losing what you already have in order to make what you don’t need.”

As someone who regularly sees millionaire retirees put their money in unnecessarily risky investments, I couldn’t agree more. If more people had adhered to Buffett’s philosophy, the fallout from 2008’s crash wouldn’t have been as horrible as it was.