Anthony Pellegrino is the co-founder and principal of Goldstone Financial Group, a Chicago-based investment firm that specializes in retirement planning and wealth management. Pellegrino has dedicated his career to helping people achieve the financial future they have worked so hard for and deserve.  He found mainstream acclaim as a co-host on the Sunday-morning CBS show, Securing Your Financial Future. Prior to its televised debut, Pellegrino’s show aired for five years on WLS 890AM, where it earned prestige as the #1 Most Listened-To financial and economic talk radio show in Chicago and has recently returned back to the airwaves. Compress Image (1) (1)

Anthony Pellegrino’s skills as a fiduciary and business leader have earned considerable acclaim; he has ranked in the Top 1% of Safe Money Specialists in the US and was recognized as one of the Top 10 Advisors in America in 2013. Today, Pellegrino lives and works in the greater Chicago area, where he guides Goldstone Financial Group to new business heights. 

An Interview with Anthony Pellegrino

Name the most impactful lesson you learned from failure.

Anthony Pellegrino: I think early on we underestimated the importance of not only making sure that we were a good fit for the client but that the client was also a good fit for us.  Several years ago, we decided to try casting a wider net and target a broader audience. It was something we had never tried before and, in retrospect, it was not a great idea. We were bringing in a client base that Goldstone Financial Group was ill-prepared to serve, and the change had consequences. Our employees were getting frustrated, our new clients felt the disconnect, and it was a lose -lose for everyone. 

Eventually, I was so frustrated by the situation that I turned to a seasoned entrepreneur and friend for advice. To my shock, he told me to fire every client who didn’t comfortably align with Goldstone Financial Group’s capabilities and interests. 

Was it a drastic move? Yes — but it resolved the issue and taught me that like everything else in business, expansion has to make sense for the company, its consumers, and its employees. 

What accomplishment are you most proud of?

Anthony Pellegrino: I think that the accomplishment I am most proud of isn’t one I can take all of the credit for. I constantly find myself humbled and uplifted by the incredible work that our team at Goldstone Financial Group puts in daily. Most people forget that behind each hard-hitting, successful CEO is a group of people who showed up, put in the time, and provided the support their leaders needed to thrive. I’m an ideas guy; I can’t tell you the number of times that I’ve scrambled to record a business notion I had in the shower before it slipped away. My team helps me take those instantaneous ideas and turn them into actionable and profitable plans. My greatest accomplishment is assembling the team that I have today — because without them, Goldstone Financial Group could never have achieved what it has. 

What did you waste the most time on when you were first starting your career?

Anthony Pellegrino: Perfectionism. Early in my career, I spent far too much time in deliberation. I found myself stressing over small uncertainties and flaws; I held myself back from action because I was worried that one missing detail would derail my plans. The truth is, all of that hesitant anxiety held me back from achieving. 

Today, I make it a point to be in motion. Here’s my rationale: if you can assess the pros and cons of a situation and determine that an idea is 80% positive, you should go for it. There is no such thing as a sure bet in business, and anyone who tells you otherwise is flat-out wrong. It’s okay to take risks and fail; after all, you have to do both to grow. But if you always wait for perfection — well, you’re never going to get anywhere, are you?

Name a tool you use for work that you can’t live without.

Anthony Pellegrino: We use Riskalyze daily. It’s a truly incredible piece of software; it empowers our advisors to pinpoint a client’s risk tolerance and analyze their potential for risk in the event of an economic downturn.

What excites you the most about your industry right now?

Anthony Pellegrino: Right now, we’re in the middle of a mass transition. Over the next decade and change, around 78 million Baby Boomers will be leaving the working world for retirement — if you do the math, that’s about 10,000 retirees per day. That’s an incredible amount, especially given that so many of these seniors simply do not have a plan in place for their post-career life. A lot of people are realizing this and seeking help. We receive numerous inquiries every day that start off with “I realized that I do not have a plan in place for retirement and it is right around the corner”, it has definitely snuck up on people but the good news is that’s what we’re here for.  There’s never been a more exciting time to be in the retirement planning industry, that’s for sure. 

Name one small habit that positively impacts your productivity.

Anthony Pellegrino: I get up early. I know it’s almost a cliche for business leaders at this point, but hey — cliches are cliches for a reason. I find that taking an hour in the morning to work out and dedicate a few moments to pray helps me center myself for the day. Being able to clear my mind and resolve any lingering stresses through prayer and exercise is well-worth the earlier alarm. 

What tips do you have for getting a seat at the table?

Anthony Pellegrino: Always keep working for that seat, and don’t let comfort or ego make you lazy. One of my favorite quotes comes from Darren Hardy, the chief editor of Success Magazine. In an article a while back, Hardy said, “Money makes people lazy; success makes people lazy.”

I couldn’t agree more. Even as a young entrepreneur, I saw high-potential businesses crash because their leaders took accomplishment for granted. Fear keeps the wick burning — so always act like you’re one day away from going out of business. That perspective will make all the difference in the world. 

What book has made the biggest impact on your life?

Anthony Pellegrino: I would say one of the most compelling books I’ve read recently would be Marshall Goldsmith’s What Got You Here Won’t Get You There. It explores the problems that can occur if you start taking your success for granted. 

Do you value intelligence or common sense more? Why?

Anthony Pellegrino: This might sound like a cop-out, but I believe it: You need to have both intelligence and common sense to survive in business. Book smarts are all well and good — as is common sense — but if you can’t adapt your theoretical knowledge to real-world challenges, your business endeavors will be dead in the water. 

What would you consider to be the perfect day?

Anthony Pellegrino: I have an incredible wife and three wonderful boys, so if I could design a perfect day, I would spend it with them. There’s nothing in the world like enjoying carefree hours with your friends and family. 

But if we’re talking workdays, I’d point you towards my usual routine. I’d wake up early, get a short workout in, and take some time to pray and reflect upon the day at hand. Then, I’d go into the office, dedicating the morning to meeting with clients and the afternoon towards growing my business. Then, I’d come home and spend the evening with my family. I have so much in my life that I’m grateful for that even my hardest days have their bright moments. 

Investment Advisory Services offered through Goldstone Financial Group, LLC (GFG) a Registered Investment Advisor.  GFG is located at One Lincoln Centre, 18W140 Butterfield Rd., 14th Floor, Oakbrook Terrace, IL  60181, Telephone number – 630-620-9300.

Anthony Pellegrino
Job Title
Goldstone Financial Group