Making Sense of Your Money Podcast

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:...

Will AI make advisors obsolete or simply better? In this episode of Making Sense of Your Money, Rob Burgess from Financial Planning Magazine this unpack the rise of AI in wealth management. From smarter CRMs to note-taking tools and portfolio automation, they explore what tech can (and can’t) replace and why human insight still reigns supreme. What You’ll Learn: Why the best advisors are tech-enab...

Most investors overlook the most consistent cash flow machines in real estate mobile home parks and parking lots. In this episode of Making Sense of Your Money, Kevin Bupp, real estate investor and principal at Sunrise Capital Investors, explore these often-ignored verticals and why they’re perfect for stable, long-term returns. What You’ll Learn: Why mobile home parks offer unmatched cash flow co...

Money is more emotional than logical especially for those historically underserved. In this heartfelt episode of Making Sense of Your Money, Shari Rash, founder of GWA Wealth and host of Everyone’s Talking Money, this explore how women and LGBTQ+ individuals can build financial confidence and clarity without the spreadsheet overwhelm. What You’ll Learn: Why traditional financial advice often fails...

Think your ESG fund is helping the planet? Think again. Most ESG portfolios aren't what they seem and that misunderstanding could hurt your impact and your returns. In this episode, Peter Krull, Partner & Director of Sustainable Investing at Earth Equity Advisors, this break down what ESG really measures and how to invest with purpose, performance, and precision. What You’ll Learn: What ESG ac...

Your parents worked hard, followed the rules and still weren’t set for life. If you’re part of a family under 40, watching house prices skyrocket, wages lag, and debt pile up, this episode is for you. Rebecca Irey, founder of Blue Skye Financial, this dismantle the outdated financial playbook and reveal how young families can build real wealth with their own rules. You’ll discover: Why the “save‑t...