Making Sense of Your Money Podcast

Dan Pascone
  • 5.0 (3)
  • Business

Hosted by Dan Pascone, CEO of Tailored Wealth (Learn more: yourtailoredwealth.com), Making Sense of Your Money helps high-income professionals optimize their financial strategies. Each episode features expert insights on investing, tax planning, and wealth building, turning complexity into clarity.Connect with Dan here: linktr.ee/danpascone.com

  1. Sep 14

    EP #70: The Hidden Cost of Winning at Work, Losing Life

    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 command, until a layoff in 2020 and the sudden loss of her father in 2022 forced her to ask a question she had never taken time to answer. Who am I without my job and without my title? We get into what it really means to separate your identity from your role, why Tricia chose to leave corporate without a perfect plan, and how she uses a simple tool called the wheel of life to design a version of success that goes beyond the paycheck. If you have ever felt like you are winning at work while everything else runs on empty, this conversation gives you a practical way to think about balance, not just balance sheets. For executives weighing their own hybrid retirement timeline, Tricia's story is a reminder that the financial plan and the identity work have to move together. Want to talk through your own hybrid retirement or equity strategy? Book a Free Wealth Strategy Call: https://yourtailoredwealth.com/book-a-call More episodes and resources: https://www.makingsenseofyourmoney.com/ #HybridRetirement #ExecutiveCoaching #WorkOptional #FinancialPlanning #RichLife 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.

  2. Aug 7

    EP #69: The College Sticker Price Is Almost Never What You Pay

    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 least amount of investment. She works the numbers most parents never see, and she has two kids of her own heading through the system right now. We get into why the published cost of attendance is almost never what you pay, how to decode a school's real business model, and the financing moves most parents miss. Shanna breaks down how to read a school's net price calculator, when to take the federal direct loan even if you do not need it, and how to turn a hundred-thousand-dollar decision into a monthly number a 17-year-old can actually understand. We also get into where college is heading in the AI era, why some schools will get more valuable rather than less, and the cash flow most parents forget they free up the day their kid leaves home. Topics Discussed: The three-legged table for choosing a school Why the sticker price is rarely the real price How to decode a school's business model and net price calculator 529s, Roths, taxable brokerage, and cash flow as funding sources When to take the federal direct loan as a safety net Turning a six-figure loan into a monthly number kids understand Where college is heading in the AI era What You'll Learn: How to figure out what your family will actually pay for a given school Which financing levers to pull and in what order How to set financial expectations with your student years in advance Why timing income and distributions matters for aid eligibility Learn more: makingsenseofyourmoney.com #CollegePlanning #FinancialPlanning #529Plan #CollegeTuition #WorkOptional 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.

  3. Jul 31

    EP #68 The Fear You Cannot Analyze Your Way Out Of

    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 partner who spent 25 years running product and strategy in the corporate world before building her own practice. She helps leadership teams that have outgrown the way they work together reach the next level of performance their business now demands. We get into how to spot a team that is quietly fracturing, the body language, the silence, the side conversations, and how to build real healthy conflict instead of just claiming you want it. Rachel makes the case that trust and vulnerability start with the leader, and that consensus is not the goal, being heard is. Then we get personal. Rachel spent eight to ten years thinking about leaving corporate before a milestone birthday finally pushed her to move. We talk about facing the fear you cannot analyze your way out of, and what the transition to running your own practice actually looks like on the other side. Want to talk through your own hybrid retirement or equity strategy? Book a Free Wealth Strategy Call: https://yourtailoredwealth.com/book-a-call More episodes and resources: https://www.makingsenseofyourmoney.com/ This content is for educational purposes only and does not constitute investment, tax, or legal advice. Consult a qualified professional for guidance specific to your situation. #Leadership #ExecutiveLeadership #WorkOptional #HealthyConflict #CareerTransition 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.

  4. Jul 24

    EP #67: The Test That Tells You If You Can Leave Corporate

    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 into a clear operating system, and he made the exact leap a lot of executives in their 40s and 50s are quietly weighing. We get into how to test your way out of corporate before you jump, using a low risk environment to see if you even like the work, not just whether you can sell it. Rick makes the case for doing early work free or cheap to learn your customer, your objections, and your real value before you set a price. Then we shift to the business itself. Why not all revenue is good revenue, how to find the levers that actually drive profit instead of just top line, and why cash flow, not profit, is the number that keeps a company alive. It is the same mindset shift we push on the personal side: budgeting is small, planning is the goal. Want to talk through your own hybrid retirement or equity strategy? Book a Free Wealth Strategy Call: https://go.oncehub.com/WealthClarity More episodes and resources: https://www.makingsenseofyourmoney.com/ This content is for educational purposes only and does not constitute investment, tax, or legal advice. Consult a qualified professional for guidance specific to your situation. #WorkOptional #FractionalCFO #Entrepreneurship #FinancialPlanning #CashFlow 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.

  5. Jul 21

    EP #66: The Exercise Executives Skip Before Leaving Corporate

    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 and trading, before walking away from the salary to build something he could eventually step back from. He is doing exactly what a lot of executives in their 40s and 50s are quietly thinking about, and he is doing it with math instead of hope. We get into the visualization exercise he ran five years ago that produced the seven pillars his weeks are still structured around. We get into how he defines the end zone first, then backs into the funding required, then solves for the delta between what he has today and what work optional actually costs. That is the same logic behind Life Driven Investing, just applied to a business owner instead of an equity comp heavy executive. We also cover something every listener pays for and almost nobody manages: energy. Tom explains why roughly fifteen states let you choose your supplier, and how locking a forward rate takes one variable off the budget entirely. Want to talk through your own hybrid retirement or equity strategy? Book a Free Wealth Strategy Call: https://go.oncehub.com/WealthClarity More episodes and resources: https://www.makingsenseofyourmoney.com/ This content is for educational purposes only and does not constitute investment, tax, or legal advice. Consult a qualified professional for guidance specific to your situation. #WorkOptional #HybridRetirement #FinancialPlanning #Entrepreneurship #RichLife 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.

  6. Jul 3

    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 fundThe real differences between owning rental property, investing in syndications, and hard money lendingWhy Michael walked away from bigger, splashy returns for steadier, more predictable incomeDepreciation, cost segregation, and how syndication income gets favorable tax treatmentHow lending income is taxed differently than real estate ownershipHow 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 expectationsWhy real estate cash flow is rarely immediate and what to expect in year oneHow depreciation can defer taxes on syndication income, and why lending does not offer the same benefitA simple framework for calculating what your investments actually need to produce to fund the lifestyle you wantHow alternative income sources can reduce the pressure on your portfolio as you consider a hybrid retirement Learn more: 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.

  7. Jun 26

    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 DiscussedWhat hybrid retirement meansWhy traditional retirement may not fit high-performing professionalsThe difference between FIRE and FINE: Financial Independence, Next EndeavorWhy many high earners may be closer to work optional than they thinkHow leaving a W-2 role can create more tax planning flexibilityThe three income phases: W-2 years, tax-control years, and IRS-mandated income yearsWhy financial planning should begin before you are ready to leave corporateWhy career planning is just as important as financial planningHow to think about your next endeavor after corporate lifeConsulting, fractional work, and monetizing your expertiseContent creation, writing, and publishing as possible income pathsBusiness ownership, Main Street businesses, and franchisingWhy starting early can create more family time, travel, purpose, and flexibilityHow 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 retirementWhy “Financial Independence, Next Endeavor” may be a better fit than FIRE for high earnersHow corporate leaders can transition from W-2 income to more flexible workWhy the tax code often becomes more favorable after leaving a high-income W-2 roleThe three earning phases: W-2 years, tax-control years, and IRS-mandated income yearsWhy work optionality may be closer than many executives thinkHow consulting, fractional work, content, business ownership, and franchising can fit into a next chapterWhy financial planning and career planning need to happen togetherWhy waiting too long to plan can cost you time, flexibility, and quality of life 🔗 Learn more: 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.

  8. Jun 12

    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 decisionHow career changes impact long-term wealth, retirement, and lifestyle goalsWhat makes hiring for go-to-market roles uniqueThe difference between builders, scalers, rebuilders, and operatorsHow GTM leaders can identify the right company stage for their skill setWhy many sales leadership roles have high turnoverHow to evaluate risk before accepting a CRO, VP Sales, or GTM leadership roleWhy equity compensation may not always be as valuable as it looksCurrent compensation trends in GTM rolesWhat candidates should negotiate beyond base salary, bonus, and equityThe importance of 401(k), Roth 401(k), and mega backdoor Roth benefitsHow deferred compensation can support senior executives nearing career transitionUsing phased exits, advisory roles, and succession planning as negotiation toolsWhy networking and thought leadership matter for GTM career growthAnthony Herrera’s advice for younger professionals: keep saying yes 🎯 WHAT YOU’LL LEARN How GTM leaders can find the right role and company stageWhy compensation should be viewed through a financial planning lensWhat to consider when evaluating equity, bonus, and benefitsHow retirement benefits can accelerate financial independenceWhy deferred compensation and phased exits can be powerful toolsHow senior leaders can negotiate for better alignment between work, wealth, and life 🔗 Learn more: 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.

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About

Hosted by Dan Pascone, CEO of Tailored Wealth (Learn more: yourtailoredwealth.com), Making Sense of Your Money helps high-income professionals optimize their financial strategies. Each episode features expert insights on investing, tax planning, and wealth building, turning complexity into clarity.Connect with Dan here: linktr.ee/danpascone.com

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