In this episode, we dive deep with Sukesh Pai, CFA, Founder & Principal at Trillium Square Advisors, whose journey from building code at Microsoft to building trust with families across America is anything but conventional.With over 20 years of diverse experience across technology, hedge funds, and Wall Street giants like Morgan Stanley, Sukesh brings a unique lens to wealth management, one that combines the analytical rigor of engineering with the emotional intelligence of a trusted financial partner.Based in North Carolina and working with clients nationwide, Sukesh serves a broad spectrum of professionals, particularly those in the technology and engineering communities. While many of his clients happen to be first-generation Indian immigrants, he clarifies in the episode: this is not a “hard niche,” but a vibrant, growing segment with shared values around education, family, and financial security.The discussion explores how behavioral patterns such as a deep-rooted culture of saving and a preference for real estate shape financial choices. Sukesh also shares how second-generation Indian-Americans are embracing more diversified strategies and seeking advisors who can act as partners, not just planners.But this conversation goes far beyond one demographic.We unpack:- The shift from institutional investing to deeply personal financial advice- The evolving expectations of the modern investor- How Sukesh uses Python & AI to scale and personalize wealth planningAnd why trust, not just tools remains the cornerstone of good advice in the AI era

In this episode of Advisor Ally, we sit down with Steve Boorstein - the founder of a values-driven, flat-fee financial planning firm RockCrest Financial LLC, and a true advocate for comprehensive, life-centered wealth management.

Steve’s journey from pharmacist to financial advisor is anything but ordinary and his insights into industry evolution, client psychology, and the role of technology in advisory practices are both timely and transformative. 💡

Steve is a “Personal Finance CEO” — helping successful individuals and families align their money with their values, simplify their lives, and focus on what matters most.

He and his team deliver all-inclusive, flat-fee planning across five key areas:

✔️ Financial Planning

✔️ Tax Strategy

✔️ Estate Planning

✔️ Investment Management

✔️ Risk Management

They coordinate across disciplines and with other professionals to ensure clients’ entire financial houses are in perfect order—and stay that way.

🔍 In This Episode:

- Steve’s leap from pharmacy to financial planning

- His early passion for stocks and self-education in finance

- Why flat-fee fiduciary planning is the future of advice

- How generational differences affect advisor-client relationships

- What Gen X, Millennials, and Boomers each expect from an advisor

- The role of AI and automation in creating a more human practice

- Advice for advisors looking to modernize their offering and tech stack

- What it really takes to build a multigenerational, purpose-driven firm

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#FinancialPlanningPodcast #ComprehensivePlanning #NextGenAdvisors #AIinFinance #TechInAdvisory #AdvisorJourney

#ClientCentricAdvice #ValuesBasedPlanning #FamilyOfficeModel #FinancialAdvisor #RIACommunity