Former PayPal CFO on Risk and Return in Venture Capital, Private Equity, and Public Companies

As a CFO, how should the way you navigate risk and return change from venture-backed companies to publicly-traded companies to private equity companies? To answer this question, CJ speaks with Mohit Daswani, a seasoned CFO with experience across multiple stages, including roles as CFO of Payments, Platform, and Risk at PayPal, and Head of Finance & Strategy at Square. Mohit shares the lessons learned from his time at Square, including when Jack Dorsey seeded a second billion-dollar business from within the company, and his experience at PayPal when they spun out from eBay under activist pressure. The conversation also covers the Rule of 40 in the different financial models, the dangers of using valuation as a scorecard, how founders should reset their mindset on what defines success, and the likelihood of a super app for the USA.

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LINKS:

Mohit Daswani on LinkedIn: https://www.linkedin.com/in/mohitdaswani1/

SimplePractice:

https://www.simplepractice.com/

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics:

http://mostlymetrics.com

RELATED EPISODES:

From CF-No to CF-Go: Serial CFO Michael Bayer’s Guide to Hypergrowth:

Inside Grab: How a Super App Transformed Southeast Asia — with CFO Peter Oey:

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Timestamps:

(00:00) Preview and Intro

(02:42) Sponsor – Planful | Tabs | Rippling Spend

(06:36) Mohit’s Office and a Tip From Churchill

(09:07) Risk and Return in Different Investment Models

(13:05) Financial Discipline Versus Room for Growth in Venture-Backed Companies

(16:30) Sponsor – Pulley | Tropic | NetSuite

(20:25) Balancing Short-Term Performance and Long-Term Bets in the PE Space

(24:00) The Rule of 40 in Different Financial Models

(30:19) What People Get Wrong About the Private Equity Model

(34:40) The Benefits of Using Leverage

(37:41) The Dangers of Using Valuation as a Scorecard

(41:41) How Founders Should Reset Their Mindset on What Constitutes Success

(44:00) Being at Square When Jack Dorsey Seeded a Second Billion-Dollar Business

(49:43) Being at PayPal When They Spun Out From eBay

(53:59) PayPal’s Acquisition of Braintree

(55:48) The Probability of a Super App for the USA

(58:38) Learnings From Launching PayPal’s Payments Dongle in Japan

(1:04:12) Long-Ass Lightning Round: A Flight Mistake

(1:06:20) Advice to Younger Self

(1:07:31) Finance Software Stack

(1:09:28) Craziest Expense Story

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#VentureCapital #PrivateEquity #RiskManagement #RuleOf40 #PayPal