EP #61 Why High Earners Build Big Portfolios That Never Actually Work For Them

EP #65: REITs vs Syndications vs Hard Money Lending

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 running publicly traded REITs to launching his own real estate fund * The real differences between owning rental property, investing in syndications, and hard money lending * Why Michael walked away from bigger, splashy returns for steadier, more predictable income * Depreciation, cost segregation, and how syndication income gets favorable tax treatment * How lending income is taxed differently than real estate ownership * How Michael funded his own transition out of full time corporate work What You'll Learn * How to evaluate REITs, syndications, and hard money lending against your own return and time expectations * Why real estate cash flow is rarely immediate and what to expect in year one * How depreciation can defer taxes on syndication income, and why lending does not offer the same benefit * A simple framework for calculating what your investments actually need to produce to fund the lifestyle you want * How alternative income sources can reduce the pressure on your portfolio as you consider a hybrid retirement Learn more: makingsenseofyourmoney.com [http://makingsenseofyourmoney.com] #HybridRetirement #RealEstateInvesting #PassiveIncome #EquityComp #FinancialPlanning Disclaimer Tailored Wealth is a marketing name used when offering advisory services, however advisory services are conducted exclusively through Sovereign Financial Group, Inc. Services are only offered to clients or prospective clients where Sovereign and its representatives are properly licensed or exempt from licensure.

EP #64 Hybrid Retirement and Becoming Work Optional

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 meaningful work, purpose, income, and flexibility. He shares why many high earners may be closer to becoming work optional than they realize, how the tax code can become more favorable after leaving corporate, and why the best plan includes both a financial strategy and a career strategy. Dan also explores potential next chapters, including consulting, fractional work, content creation, business ownership, franchising, and passion-driven projects. The key message: do not wait until you are ready to leave corporate to start planning. Start the financial plan and career plan now so you can create more options, more confidence, and more control over your time. TOPICS DISCUSSED * What hybrid retirement means * Why traditional retirement may not fit high-performing professionals * The difference between FIRE and FINE: Financial Independence, Next Endeavor * Why many high earners may be closer to work optional than they think * How leaving a W-2 role can create more tax planning flexibility * The three income phases: W-2 years, tax-control years, and IRS-mandated income years * Why financial planning should begin before you are ready to leave corporate * Why career planning is just as important as financial planning * How to think about your next endeavor after corporate life * Consulting, fractional work, and monetizing your expertise * Content creation, writing, and publishing as possible income paths * Business ownership, Main Street businesses, and franchising * Why starting early can create more family time, travel, purpose, and flexibility * How work optionality can help you design and live your version of a rich life 🎯 WHAT YOU’LL LEARN * What hybrid retirement means and why it is different from traditional retirement * Why “Financial Independence, Next Endeavor” may be a better fit than FIRE for high earners * How corporate leaders can transition from W-2 income to more flexible work * Why the tax code often becomes more favorable after leaving a high-income W-2 role * The three earning phases: W-2 years, tax-control years, and IRS-mandated income years * Why work optionality may be closer than many executives think * How consulting, fractional work, content, business ownership, and franchising can fit into a next chapter * Why financial planning and career planning need to happen together * Why waiting too long to plan can cost you time, flexibility, and quality of life 🔗 Learn more: makingsenseofyourmoney.com [http://makingsenseofyourmoney.com] #HybridRetirement #WorkOptional #FinancialIndependence #ExecutiveWealth #RetirementPlanning #CareerTransition #CorporateExit #TaxPlanning #WealthPlanning #FinancialPlanning #NextChapter #FINE #FinancialIndependenceNextEndeavor #MakingSenseOfYourMoney #TailoredWealth Tailored Wealth is a marketing name used when offering advisory services, however advisory services are conducted exclusively through Sovereign Financial Group, Inc. Services are only offered to clients or prospective clients where Sovereign and its representatives are properly licensed or exempt from licensure.

EP #63 GTM Careers, Compensation & Wealth Planning with Anthony Herrera

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 compensation should be evaluated far beyond base salary and bonus. Dan and Anthony also discuss equity compensation, 401(k) benefits, mega backdoor Roth opportunities, deferred compensation, leadership development stipends, hybrid work, and creative ways senior leaders can negotiate roles that support their broader life goals. TOPICS DISCUSSED: * Why your next executive or GTM role is also a financial planning decision * How career changes impact long-term wealth, retirement, and lifestyle goals * What makes hiring for go-to-market roles unique * The difference between builders, scalers, rebuilders, and operators * How GTM leaders can identify the right company stage for their skill set * Why many sales leadership roles have high turnover * How to evaluate risk before accepting a CRO, VP Sales, or GTM leadership role * Why equity compensation may not always be as valuable as it looks * Current compensation trends in GTM roles * What candidates should negotiate beyond base salary, bonus, and equity * The importance of 401(k), Roth 401(k), and mega backdoor Roth benefits * How deferred compensation can support senior executives nearing career transition * Using phased exits, advisory roles, and succession planning as negotiation tools * Why networking and thought leadership matter for GTM career growth * Anthony Herrera’s advice for younger professionals: keep saying yes 🎯 WHAT YOU’LL LEARN * How GTM leaders can find the right role and company stage * Why compensation should be viewed through a financial planning lens * What to consider when evaluating equity, bonus, and benefits * How retirement benefits can accelerate financial independence * Why deferred compensation and phased exits can be powerful tools * How senior leaders can negotiate for better alignment between work, wealth, and life 🔗 Learn more: makingsenseofyourmoney.com [http://makingsenseofyourmoney.com] #GTM #ExecutiveCareers #SalesLeadership #CompensationPlanning #WealthStrategy #CareerStrategy #EquityComp #RetirementPlanning #FinancialPlanning #MakingSenseOfYourMoney Tailored Wealth is a marketing name used when offering advisory services, however advisory services are conducted exclusively through Sovereign Financial Group, Inc. Services are only offered to clients or prospective clients where Sovereign and its representatives are properly licensed or exempt from licensure.

EP #62 The Rich Life Isn't About Money: A Former CFO's Journey to Fulfillment

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 corporate leadership to life architecture, why many successful people feel stuck despite achieving their goals, and how to stop waiting for "someday" to build your version of a rich life. Topics discussed: • The hidden cost of chasing titles and money • Why high achievers often feel unfulfilled • The difference between performing and thriving • Building a life across all dimensions of success • Creating your personal North Star • How meditation transformed Chris's life • Lessons from scaling multiple high-growth companies • Living and working remotely from rural Zambia If you're a business owner, executive, entrepreneur, or professional seeking more than just financial success, this conversation will challenge how you think about wealth, purpose, and fulfillment. 🎯 WHAT YOU’LL LEARN Why high income and high success can still feel unfulfilling when life isn’t intentionally designed How a former CFO went from scaling billion dollar companies to building a completely different life in rural Africa Why “performing at the top” can still leave you burned out, even when you’re winning on paper The difference between chasing titles and intentionally architecting a life across multiple dimensions Why most high achievers never actually stop to define what they want beyond career success How stepping back from constant noise can create clarity most people never reach in high-performance environments Why “someday” thinking keeps even successful people stuck in the same patterns for years What it looks like to rebuild your life around alignment instead of obligation or expectation Why your environment and distance from constant pressure can completely reshape your thinking How to recognize when your success is working against your well-being instead of supporting it. 🔗 Learn more: makingsenseofyourmoney.com [http://makingsenseofyourmoney.com] #MakingSenseOfYourMoney #ChrisGiomblanco #RichLife #PersonalGrowth #Leadership #ExecutiveCoaching #LifeDesign #Entrepreneurship #BusinessGrowth #SuccessMindset #FinancialFreedom #PurposeDrivenLife #CareerDevelopment #HighPerformance #CEOLeadership #FounderJourney #BusinessPodcast #MindsetMatters #WealthBuilding #TailoredWealth Tailored Wealth is a marketing name used when offering advisory services, however advisory services are conducted exclusively through Sovereign Financial Group, Inc. Services are only offered to clients or prospective clients where Sovereign and its representatives are properly licensed or exempt from licensure.

EP #61 Why High Earners Build Big Portfolios That Never Actually Work For Them

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 underperform the benchmark, year after year — and nobody's talking about it. In this conversation, you'll learn: * Why purpose has to come before portfolio design — and how to figure out yours * The difference between volatility and risk (and why conflating them costs you money) * What asset location is and why it may be worth more than your asset allocation * How to actually measure whether your advisor is adding value * Why the accumulation mindset quietly destroys your retirement experience If you're a high earner who's optimized your career but hasn't designed the life your money is supposed to fund — this one's for you. 🎯 WHAT YOU'LL LEARN * Why purpose has to come before portfolio design — and how to figure out yours * How to apply a business CFO cash flow mindset to your personal finances * The difference between volatility and risk — and why conflating them is quietly costing you * What asset location is, how it differs from asset allocation, and why it could save you 1.5% per year in tax drag * Why most investors are unknowingly paying their advisors to underperform the benchmark * How to make the mental shift from accumulation to actually using your money * What to do when you've never thought about what your money is actually for * Why one-time financial advice in a vacuum can be more dangerous than no advice at all 🔗 Learn more: makingsenseofyourmoney.com [http://makingsenseofyourmoney.com] #PersonalFinance #WealthManagement #FinancialPlanning #InvestingStrategy #AssetLocation #RetirementPlanning #HybridRetirement #MakingSenseOfYourMoney #DanPascone #HighEarners #TaxStrategy #PortfolioManagement #FinancialAdvisor #MoneyMindset #ExecutiveFinance Tailored Wealth is a marketing name used when offering advisory services, however advisory services are conducted exclusively through Sovereign Financial Group, Inc. Services are only offered to clients or prospective clients where Sovereign and its representatives are properly licensed or exempt from licensure.