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 planning

And why trust, not just tools remains the cornerstone of good advice in the AI era