Is your sales engine running on guesswork and heroics or proven process?

In this high-impact episode of Making Sense of Your Money, Gabe Lullo, CEO of AlleyOop, unpack how founders and revenue leaders can build a predictable, high-performing outbound engine. From removing prospecting from your top closers plates to creating structure with SDRs, Gabe reveals how to unlock scale without burning out your team.

• Why your best closers shouldn’t be cold calling
• How to align SDRs to bridge the marketing and sales gap
• The “Alley-Oop” approach to consistent outbound success
• Why founder-led selling hits a ceiling and how to break through
• The math behind opportunity cost and prospecting ROI
• Scaling outbound while keeping brand voice and quality control

Featuring: Dan Pascone & Gabe Lullo

🎧 Ready to replace sales chaos with consistency? Tune in now and learn how the best teams build scalable revenue engines.

🔗 www.makingsenseofyourmoney.com

#MakingSensePodcast #DanPascone #GabeLullo #AlleyOop #SalesDevelopment #SDRStrategy #RevenueGrowth #OutboundSales #SalesProspecting #B2BSales #FoundersJourney #SalesLeadership #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.

What does climbing Everest have to do with financial planning? For Chip Pyfer, everything.

In this riveting episode of Making Sense of Your Money, financial advisor and mountaineer Chip Pyfer explore how facing death at 26,000 feet reshaped his perspective on money, purpose, and legacy. From risking it all in the Khumbu Icefall to guiding clients through the “death zones” of financial fear, Chip shares profound lessons on living intentionally on and off the mountain.

• The mindset shift from chasing summits to defining your “why”
• How fear in finance mirrors fear on the mountain and how to conquer both
• The importance of having a financial Sherpa (and how to find yours)
• A simple discovery framework to align your money with meaning
• What near-death experiences teach us about legacy, family, and fulfillment

Featuring: Dan Pascone & Chip Pyfer

🎧 Ready to rethink what wealth really means? Tune in now for a powerful conversation about fear, focus, and financial clarity. 🔗 www.makingsenseofyourmoney.com

#MakingSensePodcast #TailoredWealth #ChipPyfer #DanPascone #Wealthspire #ClimbYourMountain #EverestLessons #FinancialPlanning #LifePurpose #OvercomingFear #LegacyPlanning #FinancialSherpa #HighNetWorthInsights

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 high performers are stuck in a hustle crash repeat cycle. But what if scaling success didn’t require burnout?

In this episode of Making Sense of Your Money, Michelle Terpstra founder of Revenue Rascals and fractional CRO this unpack what sustainable high performance really looks like in today’s leadership landscape.

Michelle shares how to build autonomy, embed pleasure into your workflow, and why corporate cultures must evolve if they want to retain elite talent.

• Why autonomy is the value for high-performing sellers
• The dangers of hustle then rest and how to break the burnout loop
• How to retain top talent without endless perks or micromanagement
• Sustainable growth principles for scaling teams and revenue
• How your personal habits affect your long-term wealth and leadership impact

Featuring: Dan Pascone & Michelle Terpstra

🎧 Ready to scale smarter, not harder? Listen now and unlock your next level. 🔗www.makingsenseofyourmoney.com

#MakingSensePodcast #MichelleTerpstra #RevenueLeadership #HighPerformanceHabits #BurnoutRecovery #TailoredWealth #SalesLeadership #FractionalCRO #WorkLifeDesign #ScalingSustainably #DanPascone #WealthStrategy #FinancialFreedom

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 founders wait too long to plan their exit and leave millions on the table.

In this episode of Making Sense of Your Money, business exit strategist Evan Duke reveal what truly makes a company “sale-ready.” From customer concentration risk to over-reliance on the owner, this conversation breaks down the biggest mistakes founders make and how to fix them before it’s too late.

What You’ll Learn:

• When to start building your exit plan (hint: it’s not when you’re ready to sell)
• Why your business must run without you before a buyer ever signs
• How to identify and reduce valuation killers
• What earnouts really look like and how to maximize them
• Why post-sale planning is just as critical as the sale itself

Featuring: Dan Pascone & Evan Duke

🎧 Ready to exit on your terms? Don’t miss this episode.

🔗 www.makingsenseofyourmoney.com

#MakingSensePodcast #BusinessExit #TailoredWealth #DanPascone #EvanDuke #ExitPlanning #MergersAndAcquisitions #Earnouts #BusinessValuation #FounderLife #EntrepreneurExit #SuccessionPlanning #ExitStrategy #WealthStrategy #BusinessOwnerTips #CEOLife

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.

Will AI make advisors obsolete or simply better?

In this episode of Making Sense of Your Money, Rob Burgess from Financial Planning Magazine this unpack the rise of AI in wealth management. From smarter CRMs to note-taking tools and portfolio automation, they explore what tech can (and can’t) replace and why human insight still reigns supreme.

What You’ll Learn:

• Why the best advisors are tech-enabled not tech-replaced
• The top tools transforming wealth management
• How financial firms are building smarter tech stacks
• Where clients draw the line on automation
• How AI can enhance, not replace, client connection

Featuring: Dan Pascone & Rob Burgess

🎧 Listen now to understand the future of financial advice and how to stay ahead.

🔗 www.makingsenseofyourmoney.com

#MakingSensePodcast #DanPascone #RobBurgess #FinancialAdvice #AIinFinance #Fintech #WealthTech #TailoredWealth #FutureOfAdvice #FinancialPlanning #AdvisorTools #FinancialInnovation #TechStack #CRMintegration

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 investors overlook the most consistent cash flow machines in real estate mobile home parks and parking lots.

In this episode of Making Sense of Your Money, Kevin Bupp, real estate investor and principal at Sunrise Capital Investors, explore these often-ignored verticals and why they’re perfect for stable, long-term returns.

What You’ll Learn:

• Why mobile home parks offer unmatched cash flow consistency
• What makes parking garages a hidden gem in urban markets
• The key signs of a high-quality operator before you invest
• How to think like an investor even in overlooked sectors
• The single biggest mistake passive investors make in real estate

Featuring: Dan Pascone & Kevin Bupp

🎧 Learn how smart investors are building serious wealth by zigging where others zag.

🔗 www.makingsenseofyourmoney.com

#MakingSensePodcast #RealEstateInvesting #MobileHomeParks #ParkingInvestments #AlternativeInvestments #KevinBupp #DanPascone #PassiveIncome #CashFlowStrategies #TailoredWealth #HiddenGems #FinancialIndependence

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.

Money is more emotional than logical especially for those historically underserved.

In this heartfelt episode of Making Sense of Your Money, Shari Rash, founder of GWA Wealth and host of Everyone’s Talking Money, this explore how women and LGBTQ+ individuals can build financial confidence and clarity without the spreadsheet overwhelm.

What You’ll Learn:

• Why traditional financial advice often fails single women & LGBTQ+ clients
• How emotions not just math drive money decisions
• The myth of performance-based planning and what to do instead
• What “accidental millionaires” really need to hear
• How Shari uses conversation not charts to empower wealth

🧠 Featuring: Dan Pascone & Shari Rash

🎧 Tap in to reframe your relationship with money and lead with confidence.

🔗 www.makingsenseofyourmoney.com

#MakingSensePodcast #TailoredWealth #WomenAndMoney #LGBTQFinance #EmotionalSpending #ShariRash #GWAWealth #FinancialConfidence #MoneyMindset #EveryoneTalkingMoney #FinancialTherapy

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.

Think your ESG fund is helping the planet? Think again.

Most ESG portfolios aren't what they seem and that misunderstanding could hurt your impact and your returns. In this episode, Peter Krull, Partner & Director of Sustainable Investing at Earth Equity Advisors, this break down what ESG really measures and how to invest with purpose, performance, and precision.

• What ESG actually measures (and doesn’t)
• The truth about “greenwashing” in funds
• Why sustainable, socially responsible, resilient
• How to spot true impact-driven portfolios
• Where biotech and infrastructure are creating growth
• The new SRI: Sustainable, Resilient, and Innovative

Featuring: Dan Pascone & Peter Krull

🧠 Want smarter investing insights? Get full access to the free content hub at www.makingsenseofyourmoney.com

#MakingSensePodcast #ESGInvesting #SustainableInvesting #PeterKrull #TailoredWealth #DanPascone #ImpactInvesting #GreenInvesting #FinancialFreedom #CleanEnergy #BiotechInvesting #InfrastructureInvesting

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.