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

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 [https://go.oncehub.com/WealthClarity] More episodes and resources: https://www.makingsenseofyourmoney.com/ [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.

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 [https://go.oncehub.com/WealthClarity] More episodes and resources: https://www.makingsenseofyourmoney.com/ [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.

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.