Milestone Money

While money may not be the most romantic topic, neither are the arguments that often arise because of poor communication around household finance and investments. Commingling of funds, saving vs. spending, and investments are topics that every couple should discuss if they want to maintain healthy finances and a healthy relationship.

Couples’ Financial Planning: Creating a Shared Path Forward - Milestone Money Learn how couples can align values, improve financial communication, and build a cohesive long-term wealth strategy together.

Grandparents who want to help the grandkids with education expenses may also be able to help themselves to an estate planning tool by gifting a 529 education plan. The grandchild gets tax-advantaged education funding, and the grandparents can apply the gift to their annual gift tax exclusion, reducing the size of the taxable estate for future heirs.

529 Education Plan Gifting: Grandparent Guide - Milestone Money Learn 529 education plan gifting strategies for grandparents. Reduce taxable estate while funding grandchildren's education tax-free.

Since 1974, when the individual retirement account (IRA) was created by Congress, these accounts have become a mainstay for many individuals who want to save for a more secure retirement. Since their creation, however, IRAs have received many refinements and additions, making them an even more versatile tool for long-term savings. Milestone Money founder Randy Dippell provides some helpful basics.

Guide to IRA Types: Traditional, Roth, SEP & SIMPLE Learn about the 4 main IRA types and their tax benefits. Discover which retirement account—Traditional, Roth, SEP, or SIMPLE IRA—is right for you.

Having a qualified professional in your corner can really make a difference. Whether it’s car repair, legal questions, or making the right decisions for your retirement, dependable guidance from a certified professional can provide confidence that you’re doing the right thing. Our article discusses the advantages of having the services of a Retirement Management Advisor®.

What Is a Retirement Management Advisor®, and Do You Need One? - Milestone Money Discover what a Retirement Management Advisor® (RMA®) does, how they help with income planning, taxes, and longevity risk, and whether you should work with one.

The decision about how to manage inherited wealth can be complicated by several factors: the nature of the assets, their cost basis, your own financial picture, and others. A qualified, professional financial advisor can be a huge help in figuring out what to do. Our article offers some helpful guidance.

I Inherited Stock: What Should I Do Next? - Milestone Money Inheriting stock can feel overwhelming. Learn how stepped-up cost basis, concentrated holdings, and a clear financial plan can help you manage inherited stock wisely and protect your long-term goals.

A retirement upsurge among the Baby Boom generation is creating ripple effects across multiple industries, and one of those effects is an increase in the options available for retirees who want to secure their options not only in the early years, but also in the later years of retirement. Our article provides some basic information about continuing care retirement centers and how they can fit into the retirement planning picture.

Is a Continuing Care Retirement Center Right for You? - Milestone Money Explore the pros and cons of Continuing Care Retirement Centers (CCRCs)—from costs and contracts to lifestyle and healthcare—so you can decide if they fit your retirement plan.

There’s a lot of economic uncertainty in the air these days, and for some, that may generate concerns about being ushered into retirement sooner than anticipated. Whether because of downsizing, strategic changes, or other reasons, sometimes retirement comes “too soon.” Our article offers some advice and encouragement.

“Sooner Than I Planned”: What to Do When Your Retirement Seems Premature - Milestone Money Forced to retire early? You're not alone. Here's how to navigate the financial (and emotional) curveballs of unexpected retirement.

Wondering If You’re a Good Fit for Milestone Money?

If you're 50 or older with $1M–$5M in investable assets and you're retired—or planning to retire soon—we may be the right partner for you. Our clients value financial independence, want to make the most of advanced strategies, and seek thoughtful guidance through life’s transitions. If you're ready for a lifestyle with more enjoyment, less work, and a focus on generational wealth, we're here to help.

While retirement may include leaving something behind, it’s more about who you’re becoming. Building your retirement identity starts with small shifts, not a complete reinvention.

Consider this an “operating system upgrade”: you’re still you, just applying your time and talents in new ways.

Revisit your “why.” What gives you purpose? Purpose drives fulfillment, and staying connected with both close relationships and casual community ties plays a key role in longevity and joy.

And don’t forget to talk about it. Retirement is a shared experience. Open, honest conversations with loved ones matter and will guide you as you create your retirement identity.



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Creating Your Retirement Identity - Milestone Money For many people retirement can come with a certain loss of identity. The day you stop working, all the familiar markers that you used to navigate the days and weeks are gone.

Retirement planning doesn’t have to be overwhelming. At Milestone Money, we focus on making the process simple, clear, and effective—so you can feel more confident about your future and focus on what matters most.

Meet Andrew Dippell — Director of Client Services

Andrew plays a central role in guiding clients from onboarding through the day-to-day management of their retirement roadmap. He is dedicated to maintaining a clear, jargon-free experience and prides himself on being a reliable point of contact for every client question or need.

Before joining Milestone Money, Andrew taught middle school mathematics and was honored with a nomination for “Teacher of the Year” in his final year of teaching. His earlier career included over a decade as an insurance claims adjuster, where he earned multiple customer service awards. These diverse roles have shaped his strong ability to communicate effectively and support clients with empathy and precision.

Read Andrew’s full bio to learn more.

About Retirement Wealth Advisor Firm - Randy Dippell | Milestone Money Randy Dippell is founder and wealth advisor for Milestone Money, a financial advisory firm that specializes in retirement wealth management.

Inheriting wealth can feel overwhelming, but with the right steps, it can become a meaningful foundation for your financial future.

Start by building a trusted team. A fiduciary financial advisor can serve as your financial quarterback, helping coordinate tax strategy, estate planning, and investment decisions.

Take time to understand the documents and assets you’ve received—especially cost basis rules and how inherited retirement accounts or life insurance proceeds are taxed.

With thoughtful planning and the right support, your inheritance can become a lasting resource for you and future generations.

Making Smart Decisions about Your Inheritance - Milestone Money Would you know how to avoid becoming one of the 33% who deplete a major inheritance within two years of receiving it?