Making Sense of Your Money Podcast

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.

EP #60 The Kitchen Table Conversations Families Avoid Most

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 [http://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.

EP #59 Selling With All 5 Senses | Armen Avanessian on Sales, Leadership & Living Intentionally

What happens when you’re hitting your numbers, earning well, and still quietly wondering, “Is this it?” In this episode of Making Sense of Your Money, Dan Pascone sits down with Armen Avanessian — fintech sales veteran, Head of Sales & Partnerships at Anthem, and author of Selling Senses — to discuss a completely different approach to sales, leadership, and life. Armen shares how the best sales professionals go beyond data and logic to create deeper human connection by engaging all five senses — and even a “sixth sense” rooted in intuition and purpose. They also dive into imposter syndrome, leadership growth, intentional living, and how healthy fear may actually be a sign you’re pursuing the right opportunities. This conversation is packed with insights for sales professionals, executives, entrepreneurs, and anyone trying to build a richer, more meaningful life beyond financial success. 💡 What You’ll Learn: * Why the best salespeople create sensory experiences, not just presentations * How active listening can transform relationships and sales outcomes * Why data alone isn’t enough to influence decision-making * The role of emotional connection in sales and leadership * How “healthy fear” can signal growth opportunities * Lessons Armen learned from 25+ years in fintech and sales leadership * Why intentionality matters more than achievement alone * The financial lessons Armen wishes he learned earlier in life 🔗 Learn more: makingsenseofyourmoney.com [http://makingsenseofyourmoney.com] Hashtags #MakingSenseOfYourMoney #SalesLeadership #SellingSenses #Fintech #PersonalDevelopment #Leadership #FinancialWellness #RichLife 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.