Bob Leonardo, Managing Director at MassMutual

Call Directions Website Contact the business

Bob Leonardo, Managing Director at MassMutual I provide a total financial needs analysis through a network of experienced professionals. Charles Chamber and Oswego Chamber.

Bob Leonardo is a Financial Services Executive of WWM Investments, LLC in Chicago, a firm with $500 million in assets under advisement. In his role, Bob provides families and business owners with comprehensive financial planning, wealth management solutions and risk management plan design. Bob specializes in working with divorced individuals, helping them transform challenging life transitions into opportunities for growth and change. Utilizing an open and transparent process, Bob manages each client’s unique financial needs, providing protection planning and investment advisory services tailored to their objectives. Bob has worked as a financial advisor since 2003, providing personalized service to clients and businesses nationally. Prior to joining WWM, Bob was ¬a Managing Director of Hoopis Group, where he was recognized as a top advisor for twelve consecutive years. Each year since 2010, Bob has been a member of the Million Dollar Round Table, which recognizes top financial services industry producers and leaders. Bob is committed to giving back to his community serving as a member of the Naperville Area Chamber of Commerce, St. Bob received his bachelor’s degree in Economics from Villanova University. He is a Registered Representative and member of the National Association of Insurance and Financial Advisors. Bob resides in Naperville with his wife Colleen, his two sons and daughter.

11/03/2026

U.S. stocks ended the week lower as a sharp tech selloff, including Alphabet’s record drop amid questions about AI spending, outweighed broader market gains. Treasury yields fell as the Fed held rates steady and inflation cooled, while economic data remained resilient. Check out this week’s market perspective to learn more.

Business and family circumstances can change over time. Periodically reviewing your succession strategy can help ensure ...
11/02/2026

Business and family circumstances can change over time. Periodically reviewing your succession strategy can help ensure it continues to reflect your goals and intentions for the future. Let’s review your options.

You insure your home, car, and even your phone. But what about your income? An illness or injury could keep you from wor...
10/29/2026

You insure your home, car, and even your phone. But what about your income? An illness or injury could keep you from working and put your finances at risk. Let’s review your protection strategy and help safeguard your paycheck.

“When the well runs dry, we know the worth of water.” – Benjamin Franklin Drawing a poignant parallel between the value of water when the well runs dry and the crucial importance of disability insurance when one is no longer able to earn an income. This piece captures the essence of foresight ...

Last chance to register! Hear from Daken Vanderburg, Chief Investment Officer, MassMutual Wealth Management, as he share...
10/28/2026

Last chance to register! Hear from Daken Vanderburg, Chief Investment Officer, MassMutual Wealth Management, as he shares perspective on today's economic and market environment and the factors that may influence markets in the months ahead.

Join Daken Vanderburg for a timely discussion on how economic growth has remained firm despite higher interest rates, persistent inflation pressures, and ongoing geopolitical uncertainty. The session explores what simmering geopolitical tensions and elevated inflation mean for the Federal Reserve, v...

10/26/2026

U.S. stocks ended last week mixed as investors moved away from technology and communication services and toward more defensive areas of the market. Treasuries gained on safe-haven demand, while inflation concerns persisted and elevated borrowing costs continued to pressure housing. Dive into this week’s market perspective for more analysis and key takeaways.

Many tax-related decisions can be time-sensitive, making the months leading up to year-end an important time for plannin...
10/26/2026

Many tax-related decisions can be time-sensitive, making the months leading up to year-end an important time for planning. Whether you’re considering charitable giving, retirement savings, or other investment decisions, now may be a good opportunity to review your options and coordinate with your tax professional. Let’s connect.

Three things for an employee to look at if your ESOP company is sold:1️⃣ What does this mean for you financially? It’s i...
10/23/2026

Three things for an employee to look at if your ESOP company is sold:

1️⃣ What does this mean for you financially? It’s important to be clear on the details – price per share, deal structure, and your voting rights are all important considerations.

2️⃣ How and when you’ll get paid – this varies, so it is important to be clear on the details about vesting, payout timing, and form of payment to expect.

3️⃣ Taxes and distribution options – for many employees, this may be the largest sum of money ever received, so it’s important to understand how it is taxed and how it fits in your overall financial plan.

Don’t go it alone – I can help you understand these considerations and more. Let’s connect.

Check out this guide for tax-smart giving strategies to consider before year-end: https://bit.ly/3TNKah6Ready to start b...
10/22/2026

Check out this guide for tax-smart giving strategies to consider before year-end: https://bit.ly/3TNKah6

Ready to start building your plan? Reach out today.

As your life evolves, your insurance needs may change too. Learn how term-to-permanent conversions work and whether perm...
10/20/2026

As your life evolves, your insurance needs may change too. Learn how term-to-permanent conversions work and whether permanent life insurance or the use of an available conversion option may be appropriate for your situation.

https://bit.ly/4iu7U38

10/19/2026

Last week, stocks fell as technology and AI-related weakness outweighed resilience in defensive sectors. Treasury yields declined amid demand for safety, while persistent inflation and strong consumer spending added uncertainty around interest rates. Learn more about the market forces driving recent performance in this week’s perspective.

Address

2441 Warrenville Road Suite 300
Lisle, IL
60532

Alerts

Be the first to know and let us send you an email when Bob Leonardo, Managing Director at MassMutual posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to Bob Leonardo, Managing Director at MassMutual:

Shortcuts

Share