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 before your shares gain value
• How Nevada & South Dakota trusts work to shield assets and reduce tax exposure
• What “qualified business stock space” means for founders, employees, and investors
• Real examples & strategies for getting started today

Featuring: Dan Pascone & Alessandro Chesser

🧠 Build your legacy, legally tax‑efficiently → ⁠makingsenseofyourmoney.com⁠

#MakingSensePodcast #QSBS #QualifiedSmallBusinessStock #TrustPlanning #AssetProtection #StartupFounders #Dynasty #TaxStrategy #TailoredWealth

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 are often misunderstood and poorly managed
• Strategies to diversify stock holdings without triggering huge taxes
• How to handle private company tender offers the right way
• The emotional and financial weight of equity comp—and how to balance both
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Whether you're at a startup or a public company, this is your roadmap to smarter planning and bigger outcomes.

Featuring: Dan Pascone & Karl Strube🧠 Take control of your stock comp now → ⁠makingsenseofyourmoney.com⁠

#MakingSensePodcast #EquityCompensation #RSUs #ISOs #TaxStrategy #StockOptions #TailoredWealth #KarlStrube #DanPascone

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 RSU and ESPP sales
• Avoid common tax pitfalls via lot-level optimization
• Extend 10b5‑1 access beyond the C-suite
• Give executives freedom and flexibility across the full calendar year
  
  

Featuring: Dan Pascone & Adam Crawford

🧠 Smarter strategies start here → ⁠makingsenseofyourmoney.com⁠

#MakingSensePodcast #ExecutiveCompensation #RSUs #10b5Plan #StockSales #FinancialFreedom #TailoredWealth #AdamCrawford #DanPascone

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 stronger multiples4. Build a business that runs without youIf you’re a business owner eyeing an exit in the next 2–10 years, or simply want to increase business value, this episode is your roadmap.

Featuring: Dan PAscone and James Gorzynski

🧠 Start making smarter moves with your money, watch now.
🔗 makingsenseofyourmoney.com

#exitplanning #exitstrategy #businessvaluation #successionplanning #sellmybusiness #businessowner #planningahead #businessgrowth

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 organizations.

Featuring: Dan Pascone & Jay Doran

🧠 Rethink the power of your workplace culture, watch now.

🔗 ⁠makingsenseofyourmoney.com

#MakingSensePodcast #CultureMatters #Leadership #BusinessCulture #JayDoran #TailoredWealth #ProfitThroughPeople #OrganizationalGrowth #DanPascone

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 turn your wrist into a financial powerhouse.

Ideal for: High earners, collectors, crypto investors, and business owners looking to diversify with high-performing alternative assets.

Featuring: Dan Pascone & Erich Wolters

🧠 Rethink what’s really on your wrist. Listen now.

🔗 ⁠makingsenseofyourmoney.com

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#MakingSensePodcast #LuxuryWatches #AlternativeAssets #ErichWolters #TailoredWealth #RolexDaytona #WealthStrategy #WatchCollector #DanPascone #StoreOfValue #TimelySoles #AssetProtection #SmartMoneyMoves

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, Hannah shows you how to turn every dollar into your own private bank.

Ideal for: Entrepreneurs, high-income professionals, and real estate investors looking to leverage liquidity and build generational wealth on their terms.

Featuring: Dan Pascone & Hannah Kesler

🧠 Flip the script on your financial future, listen now.

🔗 makingsenseofyourmoney.com

#MakingSensePodcast #InfiniteBanking #TailoredWealth #HannahKesler #BeYourOwnBanker #WholeLifeInsurance #CashValue #MoneyMultiplier #TaxFreeGrowth #WealthStrategy #DanPascone

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 cash advances to building smarter financial ecosystems with AI and blockchain, Andi shares how Brazil’s fintech wave is creating global solutions for SMBs.

Ideal for: Business owners, fintech enthusiasts, CFOs, and anyone obsessed with solving cash flow challenges or scaling smarter.

Featuring: Dan Pascone & Andi Pereira

🧠 Reimagine working capital, listen now.

🔗 makingsenseofyourmoney.com

#MakingSensePodcast #Fintech #WorkingCapital #TailoredWealth #BuyNowPayLater #SMBFinance #CashFlowSolutions #ReceivablesStrategy #AndiPereira #CapitalFintech #SmartMoneyMoves

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 decisions that have massive long-term impact. Whether you're changing jobs, navigating open enrollment, or eyeing retirement, this episode gives you the playbook to stop leaving money on the table.

Ideal for: Executives, professionals, and HR leaders ready to turn their benefits package into a wealth-building machine.

Featuring: Dan Pascone & Kathy Mychajluk

🧠 Discover the power of your invisible paycheck, listen now.
🔗 makingsenseofyourmoney.com

#MakingSensePodcast #EmployeeBenefits #InvisiblePaycheck #TailoredWealth #FinancialWellness #Roth401k #RetirementStrategy #KathyMychajluk #WealthOptimization #SmartCompensation #OpenEnrollment

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 job readiness, City Team is creating real, generational change.

Melanie’s journey from personal recovery to nonprofit leadership proves that generosity isn’t just charity—it’s strategy. When giving aligns with your values, it becomes a source of purpose, healing, and impact—for both donor and recipient.

Ideal for: Business leaders, philanthropists, and mission-driven professionals who want to create lasting impact through giving.

Featuring: Dan Pascone & Melanie Davis

🧠 Rewire your wealth with purpose, listen now.
🔗 makingsenseofyourmoney.com

#MakingSensePodcast #Philanthropy #TailoredWealth #PurposeDrivenWealth #FinancialWellness #CityTeam #MelanieDavis #DonorAdvisedFunds #FaithBasedLeadership #WealthWithImpact