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.