Making Sense of Your Money Podcast

Think your money is safe just because it’s in a bank? Think again. Behind every financial transaction is a maze of federal and state rules, and the average consumer is flying blind. In this episode, Chris Hilliard , co-founder of Winnow Solutions , to uncover the hidden compliance layers that shape your financial life, from AI regulations to licensing landmines and how fintechs are changing the ga...

Tired of toilets, tenants, and tiny returns? The ultra-wealthy aren't flipping houses or chasing rent checks—they're building wealth through syndications that offer scale, tax efficiency, and passive income. Discover: Why the wealthy ditch rentals for real estate syndications How to access institutional deals as an accredited investor The power of partnerships (and what to watch out for) Where syn...

If you’ve ever felt like the world is changing faster than your playbook, you’re not imagining it.  Executives and founders aren’t just navigating markets, they’re navigating meaningful change in economy, technology, leadership, and identity. In this episode, Dan Pascone sits down with Ashley Mosaic , human‑centered futurist, to explore how emotional intelligence, foresight, and values alignment a...

High growth doesn’t always mean financial health. Many companies double in revenue but collapse from within, all because their leaders don't understand cash flow. In this episode, Dan Pascone is joined by Michael Higgins , founder of Mindful Finance, to expose the hidden risk threatening fast-growing businesses: financial illiteracy among non-financial leaders . Discover: Why even profitable compa...

You know innovation costs billions, but did you know most clinical trials still fail? For executives watching capital markets, biotech investing, and long‑term innovation, understanding why drugs rarely make it from discovery to market is a competitive advantage. In this episode, Dan Pascone talks with Suzanne Vyvoda , founder of Concordia BioStrategies and seasoned biotech operator, to unpack the...

If you're a startup founder or early equity holder, this episode could save you millions in taxes. Alessandro Chesser, CEO of Dynasty , unpack Qualified Small Business Stock (QSBS) and how using the right trusts, like Nevada trusts, can protect your assets from lawsuits, creditors, and estate taxes. You’ll learn: What QSBS is and how much tax‑free gain it can offer Why early planning is crucial be...

If equity is part of your compensation, there’s a good chance you're missing opportunities or making costly mistakes. In this episode, Karl Strube, CPA , founder of Strube CPA, who specializes in helping high earners and tech professionals navigate the tax minefield of stock options, RSUs, ESPPs, and private equity comp. You’ll learn: What tax forms you must track (and where to find them) Why RSUs...

What if your stock compensation could work for you automatically, compliantly, and with less tax drag? In this episode, Adam Crawford , Head of Revenue at Candor, to demystify 10b5‑1 trading plans , a powerful tool for executives and public-company employees looking to offload company stock without triggering insider trading violations . Learn how these pre-scheduled contracts: Enable automated RS...

Planning your exit at retirement? That’s exactly how you lose big. In this episode, James Gorzynski, CEO of Certified Exit Planners, discuss how to exit on your terms by aligning your finances, business operations, and personal goals years in advance. Learn how to:1. Time your exit for maximum leverage2. Avoid owner-dependency pitfalls that kill valuations3. Structure for recurring revenue and str...

What if culture wasn’t just a feel‑good perk, but your company’s most powerful profit multiplier? Jay Doran, founder of Culture Matters, unveils how high-performing firms build clarity, values, and leadership alignment to transform culture into a competitive advantage and lasting financial success. Ideal for : Founders, CEOs transitioning to leadership, and high-achievers scaling their teams and o...

What if a luxury watch could protect your wealth better than stocks or real estate? Erich Wolters, founder of Timely Soles, reveals how the ultra-wealthy are using high-end timepieces not just for style, but for tax efficiency, asset security, and even cross-border wealth transfers. From models that double in value overnight to watches that track the gold market, this episode breaks down how to tu...

What if the best place to store your cash isn’t a bank, it’s a life insurance policy? Hannah Kesler, also known as The Single Millionaire Chick , breaks down how to take control of your finances with the Infinite Banking Concept a strategy used by the wealthy to grow tax-free wealth, fund investments, and never rely on traditional banks again. Whether you're earning six figures or starting small,...

What if your future revenue could pay your bills today without debt or delays? Andi Pereira, founder and CEO of fintech startup Capital, is reshaping the way small and midsize businesses manage cash flow. In this episode, he reveals how his platform unlocks trapped value by transforming receivables into instant payments, eliminating friction across entire supply chains. From replacing merchant cas...

Your salary isn’t the whole story, your real wealth might be hiding in your benefits. Kathy Mychajluk, a veteran benefits advisor with 25+ years across corporate and government sectors, pulls back the curtain on how most employees miss out on thousands in hidden compensation. From overlooked healthcare choices and FSA/HSA hacks to maximizing Roth 401(k) contributions, Kathy breaks down the small d...

What if the most valuable investment you make… isn’t in your portfolio, but in people? Melanie Davis, VP of Marketing & Development at City Team, shares a deeply personal and inspiring story of transformation—both her own and the lives of those served through City Team's mission. From supporting individuals overcoming addiction and homelessness to delivering programs in financial literacy and...

What if AI could build a better portfolio than your advisor? In this episode, Joseph Gradante, CEO of Alio Capital, explores how artificial intelligence and macro investing are transforming the way savvy investors build wealth. From behavior-led UX to risk parity strategies and institutional-grade tools, Joseph breaks down how Alio is empowering retail investors with a model once reserved for bill...

What if wealth wasn’t just what you make… but what you walk away with? Marine veteran and serial entrepreneur Cody Hall, founder of Tele-helping, joins the show to share how post-exit wealth strategy, intentional risk, and values-based decision-making shaped his financial life. Covered in this episode: Managing wealth post-exit: liquidity, trusts, and tax strategy Diversifying across real estate,...

Think insurance is just about protection? Think again. Dan Wice, an independent insurance advisor with 30+ years of experience, reveals how insurance can power long-term wealth, protect your estate, and create tax-efficient legacies. From term basics to advanced planning for high-net-worth individuals, this episode is your ultimate risk management playbook. Ideal for: High-income professionals, es...

Your points aren’t the problem. Your strategy is. John Taylor Garner, CEO of Odynn, joins the show to reveal how most people waste their travel rewards without even realizing it. Discover pro-level tactics for stretching Amex and Chase points, negotiating retention offers like a seasoned insider, and booking luxury experiences without spending a dime. It’s time to stop playing defense with your lo...

What if your portfolio could fight climate change, without sacrificing returns? Is purpose the new alpha? Helena Wasserman, Co-Founder of Investors for Climate, shares how more than $1B is being funneled into climate-forward private investments that don’t sacrifice returns. From family offices rethinking ESG to emerging VC shifts, this episode reveals why sustainability is no longer a side play—it...

Scaling fast? You might be bleeding cash behind the scenes. Is your sales team quietly draining your bottom line? Kyle Smith, Managing Partner at The Bridge Group, unpacks the hidden inefficiencies killing growth like bloated team structures, broken comp plans, and equity packages that underdeliver. Whether you’re a Series A startup or scaling into late-stage, this episode is your playbook for bui...

What do a dinosaur fossil and a Ferrari have in common? They might beat your index fund. Fractional investing is opening the vault to iconic assets once reserved for the ultra-wealthy. Rob Petrozzo, Co-Founder & CPO of Rally, breaks down how everyday investors are now buying into rare collectibles—from classic cars and sneakers to fine art and sports memorabilia. Learn how emotional connection...

Your vacation home could be your next wealth engine. Short-term rentals aren’t dead they’re evolving. In this episode, Shawn Moore, Founder of Vodyssey, unpacks how today’s investors are building scalable, cash-flowing STR portfolios without sacrificing their freedom. From debunking the “Airbnb bust” narrative to optimizing for passive income and long-term equity, this is your step-by-step bluepri...

Think scaling means staying local? Think bigger. Cross-border capital is quietly powering billions in global deals and this episode unpacks exactly how. Aditya Sahai, Managing Partner at Silver Mile Capital, shares behind-the-scenes insight on navigating international regulations, executing complex M&A, and scaling beyond Silicon Valley. If you’re a tech founder or investor thinking globally,...

The wealthy aren’t chasing the stock market they’re building the next one. Discover how the next generation of wealth is being built beyond Wall Street with Joseph Argiro, Founder & CEO of Iron Key Capital. This episode explores the rise of private markets covering startup syndicates, venture clubs, and shifting dynamics in VC. Whether you're a founder or a forward-thinking professional, learn...