Successfully Retired

In this episode, I sit down with Alana D’Angelica, a financial coach for high-earning women in tech who look successful on paper but often feel anxious, disorganized, or uncertain about their financial future.

Alana shares her journey from Morgan Stanley to early-stage Indeed (when it was just 50 employees), to leadership roles in fast-growing tech companies — and how those experiences shaped her coaching philosophy.

We discuss:

• Why many high earners don’t actually feel wealthy

Alana also shares a personal story of a negative experience with an advisor, and how it shaped her commitment to empowering clients with financial literacy and transparency.

If you’re earning well but still wondering where your money is going — or if you want more clarity, intention, and control in your financial life — this episode is for you.

Website: https://alanadeangelica.com

• The FIRE Movement (Financial Independence, Retire Early)

Put in your headphones and listen to me talk about sex, intimacy and being intentional with the wonderful Dr. Tina Schermer Sellers. (All this dropping a week before Valentine's? You're welcome.)

Dr. Tina brings her background as a licensed psychotherapist and the founder of the Northwest Institute on Intimacy to talk candidly about sex, shame, and why so many couples struggle to stay connected. 

We explore what “good sex” actually means—(something I’m sure all the other Financial Advisor podcasts are discussing at present). Dr. Tina reframes why sex often slows down for couples when they get past the “honeymoon” phase.

Be sure and listen in when we talk about how phones, family obligations, and our own desire to distract ourselves from our problems make it easier to avoid discomfort, while silently eroding intimacy at home, often turning sex into a boring and transactional box to check.

Then get your popcorn ready as we decide to talk about sexual shame—where it comes from, how early it takes root, and how fear-based messages about bodies and desire follow people into adulthood and can shape lifelong patterns of repression and isolation in ways that often goes unnoticed when life is busy but can be as loud as a hurricane in the quieter “golden” years of retirement.

Finally, we talk about long-term marriage and retirement: how couples drift into roles instead of staying people together, and what it looks like to repair, reconnect, and intentionally create joy in the next chapter of life.

Mentioned resources

Guest links

Dr. Tina also shares that if you want one or both of her books but can’t afford them, you can DM her on Instagram and she’ll send a promo code for the audiobook.

In this episode, I sit down with Joe Cianciolo to talk about why so many succession plans fail before the paperwork is ever signed.

We dig into the difference between building a business through strategy versus building one through people, and why expecting your kids — or successors — to think like you often creates more problems than it solves.

Listen in as Joe and I talk about how stress, wiring, ambition, and upbringing shape the next generation of leaders, and why preparing kids for inheritance isn’t about cushioning them financially, but about equipping them to handle pressure, purpose, and responsibility on their own terms.

In this episode of Successfully Retired, I sit down with Scott MacKillop, — a true adventurer in both life and work. Scott started his career as a securities lawyer in Washington D.C., went on to lead five TAMPs, and founded First Ascent Asset Management, the first flat-fee investment platform in the industry.

We talk about what happens after the climb — when you’ve built, led, and achieved so much, and then step away to ask, What’s next? Scott shares how he’s approached that transition, the challenges of leaving behind a lifelong identity, and how he’s redefining purpose in this new stage of life.

It’s a thoughtful conversation about reinvention, meaning, and what fulfillment really looks like beyond the business world — whether you’re retired, semi-retired, or just starting to think about your own next chapter.

In this home-grown edition of the podcast, I do the unthinkable:

In this episode, I talk about retirement mindset—why happiness in retirement isn’t about money but about curiosity, creativity, and purpose.

I share personal examples, read an excerpt from a book, and leave with a story of some of my clients who reinvented their lives in retirement. All that and more on successfully retired.

Rick advertises his Feng Shui episode.

I scour the corners of LinkedIn for rage bait.

We ask the question you've all been wondering, what's a good reason you should keep working with your financial advisor?

"If you don't know where you're going, any road will get you there."

The problem? 

Tune in to hear the whole conversation.

Ever heard of looking for a needle in a haystack?

But is it a good strategy?

It's no surprise to most of us that work is a big part of our identity. Whether it's at a networking event, a little league game, or the neighborhood BBQ people's first question is often "What do you do for work?" 

Listen in as Rick and I share stories of clients who have successfully found their purpose once the paycheck ends, questions we ask our clients that help them reframe their thinking in the years leading up to it, and what can go wrong if you wait too long to find hobbies outside of work.