I sit down with financial coach Kelsa Dickey to unpack why so many smart, disciplined people still struggle with money. 

I learn that traditional budgeting fails 80% of people, not because they lack willpower, but because the whole system is built backward, obsessively tracking what we already spent instead of planning for what's coming.

Kelsa walks me through her three-movement framework, spend fixed, spend future, and spend freely, and shows me how mapping paychecks forward instead of reviewing them backward eliminates guilt, decision fatigue, and the constant feeling of being two steps forward, two steps back. 

If you've ever felt like a failure for abandoning a budget app, this episode will change how you see money completely.

What's one recurring expense you know is coming but never actually prepare for until it hits you?

I sat down with Scott Miller, a financial outcome coach who spent nearly a decade climbing out of tens of thousands of dollars in consumer debt after losing his job in 2008. 

Scott breaks down the real difference between a financial coach and a financial advisor, why "awareness is curative" might be the three most important words you ever hear about your finances, and how tracking your spending, not cutting coupons or chasing a perfect FICO score, is the single habit that changes everything. 

We talk about lifestyle inflation, the shame that keeps people from asking for help, and why the first step out of debt is never about willpower, it is about knowing exactly where you stand right now.

What is one expense you have never actually tracked?

I sat down with Mike Kelly, CFP®, founder of Kelly Financial Planning and Right Path Enterprises, for a conversation that went far beyond investing, retirement, or how much money you need to be successful. We talked about why so many people spend years climbing a ladder they never consciously chose, chasing money, status, recognition, and success without stopping to define what they actually want from life.

Mike shared how working 16 to 18-hour days, neglecting his health and relationships, and eventually reaching a breaking point forced him to reconsider what success really meant. We explore life planning, finding your purpose, defining your “enough,” building habits around what matters, and why your calendar and spending can reveal your true priorities better than your goals ever will.

We also discuss how to get unstuck, the power of mentors and accountability, and why financial freedom means very little if you lose your sense of purpose along the way.

If money and status disappeared from the equation, what would success actually look like for you?

I sat down with Dr. Wally T. Luckeydoo, a high school personal finance teacher in Smyrna, Tennessee, for a conversation that hit way closer to home than I expected. 

We got into why money is still one of the most taboo topics in American households, even though it touches literally every part of our lives. 

Wally shared his own story of ending up trapped in student loan debt because no one ever told him trade school was an option. We talked about why kids form money habits way earlier than we realize, and why compound interest might be the single most powerful lesson no one teaches before graduation. 

What's one money mistake you made young that you wish someone had warned you about?

I sat down with Vered Frank, certified financial planner and founder of Stack Wealth, and we got into why so many people who make good money still feel completely stressed out about it. 

Vered breaks down why having an actual financial plan can boost your confidence by over 80%, versus just 40% for those winging it, and it's not about how much you earn. 

We talk about the shame that keeps people from even looking at their bank accounts, and why she tells her own clients to use AI tools like Claude to review their spending without judgment. 

What's one money habit you picked up as a kid that you're still trying to unlearn today?

I sat down with Hayden Ess, a wealth management expert with deep experience in annuities, advisor transitions, and financial planning, to unpack why so many of us feel lost when it comes to money. 

Hayden breaks down why financial advisors are becoming less like number-crunchers and more like life coaches, and why fee transparency should be the baseline, not the exception. 

We dig into why young people are more comfortable day trading than actually investing for the long haul, and why that's backwards.  We also talk about his work with Fiduciary Gives, a nonprofit helping future CFPs earn their certification through scholarships.

What's one money lesson you wish someone had taught you before you turned 18?

In this episode of Growing Money, I sit down with Dr. Joshua Wilson to explore the psychology behind money, trust, marketing, and business decisions. Joshua explains why expertise, credentials, and technical knowledge are not enough to earn someone’s trust. Before people evaluate your financial plan, service, or business offer, their brains are already deciding whether they feel safe, understood, and comfortable with you.

We discuss neurobehavioral finance, emotional decision-making, financial anxiety, and why people often feel first and justify their choices later. Joshua also reveals why successful entrepreneurs and high earners can remain deeply insecure even after achieving financial success. More money may improve the numbers, but it does not automatically create peace, confidence, or emotional stability.

We also explore what separates great financial advisors from technically skilled ones, why generic marketing makes businesses invisible, and how trust becomes the first real sale. This conversation is a powerful reminder that people do not simply buy information, they choose the person they trust to deliver it.

Has achieving more ever made you feel safer, or did it simply give you more to worry about?

I sat down with Stevyn Guinnip, a health coach who works exclusively with financially minded people, and this conversation completely reframed how I think about wealth. 

Stevyn treats health like a financial asset, using money language to explain biology: abdominal fat as high-interest debt, muscle as a currency you spend down after forty, stress as a tax bracket quietly eroding your reserves.

We talk about her own near-death experience with sepsis, the four-part framework she calls Mind, Mend, Meals, and Move, and why muscle loss after thirty might be the most underrated threat to long-term wealth.

Do you know your own health "credit score" and are you investing in it the way you invest in your money?

Money is never just money - and this episode of Growing Money proves it. 

I sat down with Joy Slabaugh, a CFP turned licensed trauma counselor, who's spent her career at the exact intersection of finance and emotional healing. 

Joy walked me through why our anxiety around money almost always traces back to three deep human needs: safety, freedom, or connection. 

We got into the "eating cat food alone" fear that shows up again and again in her sessions with wealthy clients, why financial advisors are rarely trained to sit with emotion, and how compulsive spending, hoarding, or even chasing the next dollar often has nothing to do with logic and everything to do with a story we inherited. 

What's the earliest memory you have about money, and do you think it's still shaping how you handle it today?

I sat down with Brian Wagman, a public equities investor and Bentley University grad, to break down what actually builds wealth versus what just feels exciting. 

We get into why dollar cost averaging beats chasing meme stocks and crypto hype, how social media and 24/7 market news have made investing more emotional than ever, and why fear and greed are both equally dangerous depending on who you are. 

Brian shares why most people approach investing more like gambling with better vocabulary, how to size risk relative to your own financial situation, and why comparing yourself to professional investors can be a trap. 

Be honest - when it comes to your money, are you more driven by fear or by greed?