Jan. 6, 2026

Why AI Projects Fail: An Oracle Strategist on Data, Guardrails & the 70% Problem | Diganta "Digs" Sen Gupta

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Why AI Projects Fail: An Oracle Strategist on Data, Guardrails & the 70% Problem | Diganta "Digs" Sen Gupta

Why do 70% of AI projects fail?

What guardrails do enterprises need for AI?

What is RAG in AI?


"If we don't have the understanding of data, it becomes so challenging. AI is something that comes

from the data." — Diganta "Digs" Sen Gupta


In this milestone Episode 100, Donna P. Mitchell, The Transformation Authority™, speaks with Diganta "Digs" Sen Gupta — Forbes Technology Council member, IEEE AI Governance Committee member, and Oracle enterprise architect with 25+ years experience — about why AI transformations fail and what executives must understand about data readiness.


What's covered:

• Why "everyone from bedrooms to boardrooms" talks AI but most projects fail

• The data silo problem destroying enterprise AI initiatives

• How Oracle went from database company to multi-cloud AI partner

• RAG, vectorization, and semantic search explained simply

• The guardrails executives must put in place before any AI project

• How blockchain creates "trusted data" for AI applications

• AI's future in healthcare: diagnostics, patient records, and beyond


Timestamps:

00:00 — Welcome & Introduction

01:01 — Digs' journey with Oracle (2007-present)

02:49 — Oracle's transformation: Database to cloud

10:28 — Why AI projects fail: The data problem

16:11 — RAG & vectorization explained

21:34 — The three mistakes executives make

37:04 — AI in healthcare: The future


Connect with Diganta "Digs" Sen Gupta:

LinkedIn: https://www.linkedin.com/in/dsgupta/


Connect with Donna P. Mitchell, The Transformation Authority™:

PivotingPortal.com

PivotingToWeb3.com

ConnectWithDonnaPMitchell.com

Forbes Business Council | C-Suite Network


#TransformationAuthority #AITransformation #EnterpriseAI #Oracle #DigitalTransformation #DataStrategy #AIGovernance #PivotingToWeb3 #podmatch


Want to be a guest on Pivoting to WEB3? Send Donna Mitchell a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/1671449794354x786692998532303600

DIGANTA SEN GUPTA Profile Photo

MASTER PRINCIPAL ENTERPRISE ARCHITECT

Diganta Sengupta is a thought leader & technology strategist and a Forbes Technology Council member leader, specializing in AI, cloud, and blockchain-driven digital transformation. With over 25+ years of experience, he has led large-scale innovations across multiple industries—modernizing systems for Fortune 500 organizations. He is a published researcher, thought leader and passionate advocate for building trusted, intelligent enterprise ecosystems.
A trusted advisor to CIOs and CTOs, Diganta blends technical depth with strategic insight, shaping go-to-market strategies and governance models. He is a published researcher, IEEE Senior Member and ACM Professional reviewer, BCS Fellow and passionate about leveraging emerging tech to build connected, resilient and intelligent enterprises.