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About Milestone Money

Milestone Money helps you manage the financial challenges of retirement, so that you can enjoy life without being concerned about money.

OUR MISSION

Income is the Outcome

As much as we imagine that retirement is a time of leisure and easy living, it is actually charged with meaningful and sometimes difficult decisions about how we manage our finances. And those decisions can have a lasting impact on the kind of life we have in retirement.

Too many financial advisors make the financial planning experience about them, rather than about you and those big decisions. They present elaborately-named processes and 65-page plans full of generic charts and graphs.

You really just want to know your financial advisor is an expert in your life goals and financial outcomes. For Milestone, that means recognizing the 3 distinct stages of retirement that we go through, the big life and tax events that take place in each, and how to transition into retirement and throughout each stage gracefully.

For some of our clients, they look to us to help them manage their paychecks and the play-checks and that we can clarify between the two. For others, they want to thoughtfully de-accumulate assets over the rest of their lives. What’s important is that your advisor helps with the planning, investments, and tax strategy to help you get where you want to go. You decide where.

IT'S ABOUT YOU

Our Values

It's About You

Everything starts with you. Your goals. Your hopes. Your dreams. Your money. We want you to feel good about your money.

Keep it Simple

Planning for retirement shouldn’t be scary. We’re committed to delivering a simple yet robust experience that helps reduce stress and potentially improves your finances in retirement.

It's Our Duty

Retirement can be complicated. And sometimes it’s difficult to know where to look for good advice. The financial industry has left many people unprepared for the realities of retirement. We are here to fix that; it’s our job

Go Enjoy Life

You’ve worked hard; don’t waste time on things that we can do for you. We crunch the numbers, provide you with options, and help you make smart decisions with your money so you can focus on what really matters to you.

It's Our Duty

Retirement can be complicated. And sometimes it’s difficult to know where to look for good advice. The financial industry has left many people unprepared for the realities of retirement. We are here to fix that; it’s our job

Go Enjoy Life

You’ve worked hard; don’t waste time on things that we can do for you. We crunch the numbers, provide you with options, and help you make smart decisions with your money so you can focus on what really matters to you.
WHO WE ARE

The Milestone Money Team

Randy Dippell, founder of Milestone Money.

Randy Dippell, CEPA, RMA
Managing Member and Owner

My name is Randy Dippell. I have been in the financial services business for 30 years, and spent the last 21 years in Wealth Management.

My mission is to serve you and your family. I am committed to serve as your family’s CFO (Chief Financial Officer) and guide you through both ordinary and unforeseen events of life. I develop long term relationships with my clients and their families, and strive to always provide you with the best possible advice.

At Milestone Money, my clients are my only priority, and I invest considerable time in all of my relationships to make sure each client gets exactly what they need. I invite you to schedule some time with me to see how I might be able to help you.

Prior to founding Milestone Money, I was the Owner and Managing Member of Nestegg Advisory, an independent wealth management firm that I started in 2012. Prior to that, I was a Vice President in the Private Bank at J.P.Morgan, and worked exclusively with High Net Worth and Ultra High Net Worth clients.

I hold the FINRA Series 66 securities license registration, and previously held the FINRA Series 7 registration. I relinquished the Series 7 designation in 2014 to reaffirm my role as a fiduciary advisor to clients.

In 2020, I earned the Chartered Retirement Planning Counselor designation from the College of Financial Planning designation, which has helped me focus on the needs of pre-retirees and clients who have already retired. I earned the Accredited Investment Fiduciary Certification in 2017, and in 2015, I received Chartered Retirement Plans Specialist designation from the College for Financial Planning. I also obtained a Certificate of Completion from Northwestern University’s Certified Financial Planner Education Program in 2006.

Away from work, I enjoy travel, media, sports and music, and live in Chicago with my wife and two children.

As Featured In

Andrew Dippell,
Director of Client Services

My name is Andrew Dippell. I am the Director of Client Services for Milestone Money. I have worked in financial services for 15 years, with the majority of my time spent in the insurance industry. My role is to provide our clients with a smooth process from onboarding to managing the day-to-day needs of your retirement roadmap and being available to assist with any client needs. At Milestone Money, we are committed to delivering a robust, jargon-free client experience.

Prior to joining Milestone Money, I taught mathematics at a local public middle school for several years. In my final year of teaching, I was honored to be nominated for the “Teacher of the Year” award. Before teaching, I spent over a decade as an insurance claims adjuster handling various lines of business including personal auto, commercial auto, property, general liability, and injury claims, and received several customer service awards for excellence. Both professions have provided me with the opportunity to refine my communication skills and given me extensive experience in meeting clients’ diverse needs.

In my free time, I enjoy hiking and being outdoors, collecting vintage home audio equipment, and spectating my two children’s sporting events. I currently reside in Mishawaka, Indiana.

RETIREMENT SORTED

Download our free checklist of 32 important issues you should really think about before you retire.

RETIREMENT SORTED

Download our free checklist of 32 important issues you should really think about before you retire.

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Life is full of financial milestones. We pay for college, we get married, we start businesses. But the most important financial decision we will ever make is when and how to retire. Milestone Money helps you map success to and through retirement.