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Randy Dippell, RMA, CRPC

Helping successful executives retire with style and live an epic retirement

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Milestone Money Randy Dippell, RMA, CRPC
Chicago, IL

Serving Clients Nationwide

Helping successful executives retire with style and live an epic retirement

(312) 815-8335

Website

Areas of Focus

  • Estate Planning
  • Financial Life Planning
  • Investment Management
  • Retirement Planning
  • Taxes

About Me

Hi, I'm Randy Dippell. I have been in the financial services business for 32 years, and spent the last 23 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.

Professional Designations

  • Accredited Investment Fiduciary (AIF)
  • Certified Exit Planning Advisor (CEPA)
  • Chartered Retirement Planning Counselor (CRPC)
  • Retirement Management Advisor (RMA)

Affiliations

  • Investments & Wealth Institute
  • XY Planning Network

Primary Location

1165 N Clark St, Ste 700 Chicago, IL 60610

Meeting Options

  • Video Conference
  • In-Person
  • Phone
Book Intro Call

Compensation Methods

  • Flat Fee
  • Percentage of Assets Managed

What to expect in the first meeting

Click the 'Book Intro Call' button above to tell us what’s on your mind using the form on the page, whether you need an answer to a question, more information about our retirement services, or you’re just wondering how windy the Windy City gets. If you’re ready to schedule a complimentary introductory meeting, click Get Started in the navigation to view scheduling options, and we’ll chat soon.

Offers Investment Management

Yes

About our Firm

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.

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.

Education

DePauw University, BA, Classical Studies and Economics

Badges

Hobbies and Interests

  • Baseball
  • Boating
  • Family
  • Football
  • Hockey
  • Movies
  • Music
  • Pickleball
  • Sports
  • Traveling
  • Wine
  • Working Out

SEC Lookup

View Disclosure

Who We Serve

  • Baby Boomers
  • Corporate Executives
  • Dual Income Family
  • Families
  • Financial Independence Retire Early (FIRE)
  • Gen X
  • Living in Retirement
  • Widow

To make Wealthtender free for readers, we earn a nominal monthly fee from financial advisors and firms in exchange for marketing services (including being featured on this profile page), subject to terms of use. This compensation creates a natural conflict of interest when we favor their promotion over others. Wealthtender is not a client of these advisors or firms. Testimonials may not be representative of other clients’ experiences and do not guarantee future performance or success.

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