Successfully Retired

Should Dual-Income Couples Combine Finances? With Alana D'Angelica

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• The common blind spots around compensation (RSUs, stock options, 401(k) match, health plans)• How lifestyle creep quietly erodes financial progress• The emotional side of money decisions• Why she believes dual-income couples should not fully combine finances• The power of starting retirement savings early• The importance of understanding investments — even if you hire an advisor• Her six-month coaching framework and investing community for women
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.
 Connect with Alana
Website: https://alanadeangelica.comLinkedIn: https://www.linkedin.com/in/alanadeangelica/Instagram: https://www.instagram.com/alanadeangelica/
Resources & Concepts Referenced
• The FIRE Movement (Financial Independence, Retire Early)• ChooseFI Podcast• Afford Anything Podcast• Ikigai framework (Japanese concept of life purpose)• RSUs (Restricted Stock Units)• Stock Options• 401(k) match optimization• Variable Universal Life (VUL) insurance• DIY investing 

Sex and Connection - Cultivating Intimacy To and Through Retirement

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
Sex, God, and the Conservative Church: Erasing Shame from Sexual Intimacy — Dr. Tina Schermer Sellers
Shameless Parenting — Dr. Tina Schermer Sellers
Not Under My Roof — Amy Schalet
Man’s Search for Meaning — Viktor Frankl
Guest links
Website: TinaSchermerSellers.com
Instagram: @DrTinaShameless
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.

Blind Spots, Legacy, and the Stories We Hand Our Kids

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.

Redefining Purpose - a Conversation with Scott MacKillop

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.

Navigating The Housing Maze: Lesson's from Burlington for Cherokee County - with Dan Thrailkill

In this home-grown edition of the podcast, I do the unthinkable:Talk about politics!Now before you get excited, know that we won't be talking about partisan politics or D.C. powerbrokers. Instead, I sit down with Woodstock entrepreneur and community-builder Dan Thrailkill to talk about a topic that’s hitting home for a lot of us: why housing feels so out of reach—and what we can actually do about it right here in Cherokee County.We look at Burlington’s community land trust experiment and how well it really worked before digging into our own county’s proposed “land bank.” Dan helps me break down the trade-offs, like how these programs affect nearby property values and whether they truly help first-time buyers.Listen in as we discuss the five L’s of affordability (land, labor, lumber, laws, lending) and why density doesn’t have to be a dirty word. We get into micro-units, zoning rules that quietly drive up costs, and the choices that help younger families and retirees alike. Most importantly, we talk about what retirees can do to influence the direction of their community: show up, ask better questions, and advocate for smart policies rather than “do something” shortcuts.If you care about housing, your neighborhood, your kids’ future here—or just want to understand how these decisions actually get made—this conversation will give you something to think about.

Stuck In Reverse?

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.

Should You Keep Working With Your Advisor

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?All that and more on Successfully Retired.

Investing Without a Plan

"If you don't know where you're going, any road will get you there."Today Rick and I unpack a case study of some new families he's met with who were doing a great job investing and capturing the growth of the market.
 
The problem? They had never checked to see when they personally could retire. The answer shocked them.
Tune in to hear the whole conversation.