The Art of Seeing What Others Miss: An "Outsider's" View of Private Equity

In this episode of Preferred Return, we sit down with Usamah Khan, Vice President of Data & Technology at White Star Capital, to explore the intersection of technology, venture capital, and data-driven decision-making. 

Usamah shares his unconventional journey from engineering and startups to venture investing, revealing how his background in data analytics and product development helps White Star assess and support portfolio companies.

He breaks down the role of technical due diligence, the challenges of AI adoption, and the unique CTO-to-CTO conversations that set White Star apart in venture investing.

In this episode, you’ll learn:

• How Technical Due Diligence Shapes Investment Decisions: Usamah explains how White Star evaluates technology startups, identifies red flags, and determines what makes a product defensible.
• The Adoption Challenge in AI: Discover why AI tools often struggle to deliver ROI and what it really takes for businesses to integrate AI successfully.
• The Power of Data in Venture Capital: Learn how White Star leverages data insights to track potential investments, monitor portfolio performance, and support founders beyond capital.

Things to listen for:

(00:00) Introduction to Usamah Khan

(01:11) From engineering to venture capital

(04:08) Early startup lessons in data analytics

(05:51) Building smart city tech at Umbrellium

(08:33) The COVID pivot that changed everything

(10:24) Finding his way to White Star Capital

(12:07) Pitching his own role and making it fit

(13:58) How White Star evaluates technology

(17:45) Spotting red flags in early-stage startups

(20:41) Unifying portfolio insights with data

(24:54) Using AI signals to track investments

(29:57) The real challenge with AI adoption

(40:04) What CTO-to-CTO talks really uncover

(45:52) Supporting founders beyond capital

(55:08) Advice for breaking into venture capital

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