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: Learn About the Hybrid Retirement Method

  1. Oct 22

    EP #72: How Top Sales Leaders Negotiate Equity, Not Just Base

    For a lot of the revenue leaders I work with, the biggest lever in their net worth is not their base. It is the equity they negotiate on the way in, and most of them leave money on the table because they treat comp as a number instead of a problem they are solving for the company. My guest this week is Dane Crossie, founder of Alpha Source GTM and a headhunter with 23 years of experience, over a decade of it placing go to market leaders at data and intelligence companies across the US and UK. He has spent his career on the other side of the table from the executives in our audience, and he knows exactly how these packages get built and won. We get into why revenue roles carry the highest turnover, how senior leaders should actually work with recruiters, and where compensation is heading. Dane breaks down why equity now outweighs base for senior leaders eyeing an exit, and the one move that wins a negotiation before it even starts. Topics Discussed: Why go to market and revenue roles see the highest turnoverHow senior leaders should work with specialist recruitersWhy equity now matters more than base for leaders eyeing an exitHow equity packages got more complex with accelerators and bonuses tied to profitWhat drove East Coast US salaries to skyrocket after 2020Positioning yourself as the answer to a company’s problem before talking compWhat You'll Learn: How to build relationships with 2 or 3 recruiters who specialize in your fieldHow to read a compensation package beyond base and OTEWhy connecting your value to the company’s goals strengthens your leverageHow to negotiate without putting the relationship at riskLearn more: makingsenseofyourmoney.com #EquityComp #SalesLeadership #ExecutiveCompensation #WorkOptional #CareerStrategy 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. Oct 14

    EP #71: It’s Not the Workload, It’s Never Coming Up for Air

    The highest performers I know are running on empty and calling it ambition. The calendar is wall to wall, the inbox never clears, and underneath it is a quiet question about whether this is really the life they signed up for. My guest this week is Joelle Moray, a licensed professional counselor who spent 17 years in corporate public affairs, workforce and economic development, and public utility policy before walking away to build her own culture and organizational development practice. She now runs her own research on burnout and works with organizations ranging from public schools and universities to financial services firms and the NFL. We get into why burnout is almost never about the workload itself, it is about never coming up for air. Joelle breaks down the 5 systemic drivers she sees in every organization regardless of industry, and makes the case most leaders resist: that a real break makes your team sharper, not lazier. We also get into her own leap out of a stable corporate seat during one of the hardest seasons of her life, and the simple financial rule that gave her the confidence to go. Topics Discussed: Why burnout is a systems problem, not a workload problem The 5 systemic drivers of burnout across every industry What leadership models versus what it says it values Why a 10 to 15 minute break genuinely resets focus and creativity How to find agency over your day when parts of it are out of your control Joelle’s leap from a corporate seat to founder, and how she de risked it What You’ll Learn: How to spot the real drivers of burnout on your team Why pausing makes people more productive, not less How to take a break that actually works, away from the phone and the Slack channel The financial rule Joelle used to make work optional on her terms Learn more: makingsenseofyourmoney.com #Burnout #Leadership #WorkOptional #ExecutiveWellness #TeamCulture 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. 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.

  4. 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.

  5. 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.

  6. 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.

  7. 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.

  8. 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.

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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: Learn About the Hybrid Retirement Method

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