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.

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.

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.

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.

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

#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.

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.

• 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

#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.

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.

• 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

#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.

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

#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.

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.

• 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

#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.

What happens when financial planning goes far beyond investments?

In this episode of Making Sense of Your Money, Dan Pascone sits down with Erin Niehaus, founder of Planning Paths and a wealth management professional with experience spanning institutional asset management, tech investing, and private banking.

Together, they discuss the emotional and practical realities of managing money across generations — from helping aging parents and preparing children financially to navigating caregiving costs, estate planning, and the difficult conversations families often avoid until it’s too late.

Erin also shares how personal experiences shaped her mission to help families prepare for life’s biggest transitions, why stewardship matters in financial planning, and how AI is transforming the wealth management industry.

This is an insightful conversation for executives, business leaders, caregivers, and anyone trying to build a richer, more intentional financial life.

💡 What You’ll Learn:

• Why financial planning should go beyond investments and portfolios
• The biggest financial risks families face with aging parents
• Why beneficiary designations and estate documents matter so much
• How to start difficult “kitchen table” conversations with family
• What the “sandwich generation” needs to prepare for financially
• How AI is changing financial planning and wealth management
• The difference between being wealthy and living a rich life
• Why stewardship and trust are critical in financial advising
  
  🔗 Learn more: makingsenseofyourmoney.com
  
  Hashtags
  #MakingSenseOfYourMoney #FinancialPlanning #WealthManagement #Caregiving #AgingParents #EstatePlanning #RichLife #PersonalFinance
  
  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.