Making Sense of Your Money Podcast

You've built the career, the comp, the title. But have you ever stopped to ask if any of it is actually what you want? In this episode of Making Sense of Your Money, I sit down with Tricia Maggio, a 25 year corporate leader turned executive coach and the CEO and Founder of TDM Coaching. Tricia spent over two decades building a reputation as the person who could solve any problem and overachieve on...

Most parents look at a six-figure college sticker price and either panic or say the words that quietly cost them a decade of retirement: "I'll just figure it out." My guest this week is Shanna Due, CFP, CCFC, AFC, founder of Due Financial. Shanna spent years as a full financial planner before specializing entirely in one thing: helping families get the college experience they actually want for the...

A lot of high performers are sitting on two versions of the same tension. At work, they lead a team that has outgrown how it used to operate, where the real conversations now happen in the hallway instead of the room. Personally, they are circling a bigger leap of their own, waiting for a right time the data never quite delivers. My guest this week is Rachel Wexler, a leadership development partne...

A lot of high earners quietly wonder if they could ever go out on their own. Then the mortgage, the kids, and the paycheck they rely on keep them feeling like a slave to the salary. My guest this week is Rick Sanchez, founder and CEO of Robyn Consulting Group and a fractional CFO who spent fifteen years in corporate finance before building his own firm. Rick helps founders turn messy financials in...

Most high earners can tell you their number. Very few can tell you what an actual Tuesday looks like on the other side of it. That gap is why work optionality stays a vague idea instead of a design. My guest this week is Tom Kinneary, founder of a specialized natural gas advisory firm. Tom spent years climbing inside a corporate energy company, moving from customer service to analyst to scheduling...

Most executives assume the stock market is their only lever for building passive income. Michael Parks, an eighteen year corporate veteran turned real estate investor and fund manager at the Navigator Wealth Fund, breaks down why that is not true and how he built steady, predictable cash flow outside the market entirely. Topics Discussed Michael's transition from eighteen years at Accenture to run...

In this solo episode, Dan Pascone breaks down the concept of hybrid retirement , a new way for high-earning professionals to think about financial independence, career transition, and life after the corporate grind. Instead of viewing retirement as a full stop, Dan explains how executives and business leaders can create the option to step away from demanding W-2 roles while still pursuing meaningf...

In this episode, Dan Pascone speaks with Anthony Herrera, President of Pursuit Sales Solutions, about how go-to-market leaders should think about career moves, compensation packages, and long-term wealth planning. They cover the current GTM hiring market, what makes sales and marketing leadership roles unique, how candidates can identify the right company stage for their skill set, and why compens...

Chris Giomblanco spent decades scaling companies like Dell, Alienware, Triad Retail Media, and Playwire as a finance executive and CFO. Today, he lives in rural Zambia, helping high-performing executives, founders, and CEOs design a life that is successful not just financially, but across every dimension that matters. In this episode of Making Sense of Your Money, Chris shares his journey from cor...

You've saved. You've built a real balance sheet. But have you ever stopped to ask — what is it actually for ? In this episode, Dan is joined by Gary Preisser, founder of Stonebriar Wealth Advisors and author of The Differentiators of Wealth . Gary spent 15+ years applying a CFO mindset to personal finance, and what he's found is uncomfortable: most investors are paying their advisors to underperfo...

What happens when financial planning goes far beyond investments? In this episode of Making Sense of Your Money , Dan Pascone sits down with Erin Niehaus, founder of Planning Paths and a wealth management professional with experience spanning institutional asset management, tech investing, and private banking. Together, they discuss the emotional and practical realities of managing money across ge...

What happens when you’re hitting your numbers, earning well, and still quietly wondering, “Is this it?” In this episode of Making Sense of Your Money, Dan Pascone sits down with Armen Avanessian — fintech sales veteran, Head of Sales & Partnerships at Anthem, and author of Selling Senses — to discuss a completely different approach to sales, leadership, and life. Armen shares how the best sale...

Most financial advice is only as good as the information behind it. In this episode, Dan Pascone sits down with Kevin Knull, founder of TaxStatus.com and former leader at MoneyGuide Pro, to discuss why incomplete data can lead to incomplete planning. Kevin explains how advisors can miss key pieces of a client’s financial life, why tax planning is one of the biggest opportunities for high earners,...

Just filed your taxes and shocked by the amount you owed? You’re not alone. In this solo episode of Making Sense of Your Money , Dan Pascone breaks down how high-earning executives and business leaders can use their tax return as a strategic planning tool instead of just a filing requirement. Dan walks through 11 practical tax planning moves to make right now while the numbers are still fresh — fr...

In this episode of Making Sense of Your Money, Dan Pascone sits down with Ashish Khanna, Partner at Hightower Signature Wealth, to talk about legacy planning, estate strategy, family communication, and why passing down wealth without passing down values often leads to failure. Ashish shares his journey from attorney to wealth advisor and explains why true legacy planning goes far beyond wills, tru...

The bigger paycheck came. Then came the bigger house, the nicer car, the upgraded lifestyle. And suddenly the golden handcuffs were on, and nobody noticed until it was too late. In Episode 55 of Making Sense of Your Money, Brandon Fluharty, founder of The Purposeful Performer and former top-1% enterprise sales executive, unpack why high-income earners are often the most financially trapped, and wh...

You're maxing out your 401(k). You think you're done. You're not even close. In Episode 54 of Making Sense of Your Money, Dan Pascone, CEO of Tailored Wealth, breaks down the three tax buckets every high earner needs to understand, and the powerful (and IRS-approved) strategy called the Mega Backdoor Roth that could unlock up to $72,000 in retirement contributions per year. This is a solo, listene...

You've spent years building your business. But if your financials are messy, your margins are murky, and your reporting is inconsistent, a buyer will use that against you. And it will cost you millions. In Episode 53 of Making Sense of Your Money, Dan Pascone, CEO of Tailored Wealth, sits down with Jeff Glick, CPA and Head of US Operations at OCFO, to break down what it actually means to make your...

"I need to get my finances together first, then I'll go see an advisor." Sound familiar? That thinking is exactly why so many women are flying blind when it matters most." In Episode 52 of Making Sense of Your Money, Dan Pascone, CEO of Tailored Wealth, sits down with Lacy Garcia, Founder and CEO of Willow, a wealth accelerator helping women find the right financial advisor through personalized ma...

Most investors don’t lose money because they lack knowledge they lose money because their brain gets in the way. In Episode 51 of Making Sense of Your Money, Justin Detray, Managing Director and Partner at Wealthspire Advisors, to unpack the behavioral biases that quietly drive bad financial decisions especially during volatile markets. Justin shares how his background as a former Wall Street prop...

Can hostage negotiation tactics actually help you close more deals? In this milestone 50th episode of Making Sense of Your Money , Sebastian Hidalgo , founder of Dorindo and creator of the SWAT Sales Method, this explore the powerful overlap between tactical negotiation and modern B2B sales. With a background in psychological operations and hostage negotiation training, Sebastian reveals how empat...

Is your sales engine running on guesswork and heroics or proven process? In this high-impact episode of Making Sense of Your Money , Gabe Lullo , CEO of AlleyOop, unpack how founders and revenue leaders can build a predictable, high-performing outbound engine. From removing prospecting from your top closers plates to creating structure with SDRs, Gabe reveals how to unlock scale without burning ou...

What does climbing Everest have to do with financial planning? For Chip Pyfer, everything. In this riveting episode of Making Sense of Your Money, financial advisor and mountaineer Chip Pyfer explore how facing death at 26,000 feet reshaped his perspective on money, purpose, and legacy. From risking it all in the Khumbu Icefall to guiding clients through the “death zones” of financial fear, Chip s...

Most high performers are stuck in a hustle crash repeat cycle. But what if scaling success didn’t require burnout? In this episode of Making Sense of Your Money, Michelle Terpstra founder of Revenue Rascals and fractional CRO this unpack what sustainable high performance really looks like in today’s leadership landscape. Michelle shares how to build autonomy, embed pleasure into your workflow, and...

Most founders wait too long to plan their exit and leave millions on the table. In this episode of Making Sense of Your Money, business exit strategist Evan Duke reveal what truly makes a company “sale-ready.” From customer concentration risk to over-reliance on the owner, this conversation breaks down the biggest mistakes founders make and how to fix them before it’s too late. What You’ll Learn:...