Today’s guest, Arvind Kadaba, the CFO of Aidoc, started his career as a high-profile investor before transitioning into the role of a CFO. He joins CJ to share his career journey and discuss the challenges he faced in transitioning into an operational role. The conversation explores the “grass is always greener” mentality that drives career shifts, and how to find the right career fit. Arvind describes the evolving landscape of healthcare technology and AI. He emphasizes the need for innovation and how to choose whether to build, buy, or partner to achieve this, giving listeners a masterclass in portfolio theory for operators. He also gives helpful tips for balancing short-term and long-term investments and explaining long-term shareholder value to employees. The episode concludes with Arvind defending his contrarian views that not all businesses should be venture-backed and not all great businesses are tech businesses.

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@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(02:21) Sponsor – Brex | Vanta | Tropic

(06:59) Transitioning from Investor to Operator

(11:13) The Problem-Specific Nature of Being an Operator

(14:29) Sponsor – RightRev | Planful

(16:39) Personal Product Market Fit

(23:18) “All You Need Is One”

(25:46) How Arvind Decided to Switch Careers

(33:07) The State of Healthcare Technology in AI

(36:05) Innovation: Build Versus Buy Versus Partner

(37:36) Portfolio Theory for Operators

(44:36) Explaining Long-Term Shareholder Value to Employees

(47:50) Not All Businesses Should Be Venture-Backed

(53:38) Not All Great Businesses Are Tech Businesses

(57:03) Long-Ass Lightning Round: Cross-Functional Trust

(58:04) Finance Software Stack

(58:54) Craziest Expense Story

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Investors vs Operators: Aidoc’s Arvind Kadaba on the “Grass Is Greener” Trap and How to Escape It