This Week in Startups

E36: “Angel” Podcast: Ajay Agarwal, Partner at Bain Capital shares insights on culture evolving from sales-driven to product-driven, why enterprise software is the ideal business, best investments & anti-portfolio

Mar 4, 2020

Ajay Agarwal, Partner at Bain Capital, shares his expertise in venture investment within enterprise software. He discusses the evolution from sales-driven to product-driven company culture, emphasizing the potential profitability of software. The conversation veers into the challenges of capitalism and declining social mobility, and Ajay highlights his successful investments, such as FourKites, while lamenting missed opportunities like Pinterest. The dialogue also touches on the transformative power of entrepreneurship and the critical importance of gross margin in the software industry.

01:05:29

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Episode guests

Ajay Agarwal

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Episode notes

Intro

2min

Redefining the American Dream

10min

Breaking Barriers: Empowering Change Through Entrepreneurship

7min

Understanding Gross Margin in Software

5min

The Evolution of Enterprise Software: From Challenges to Accessibility

2min

Navigating the Evolution of Sales in Enterprise Software

2min

Seamless Living and Venture Insights

2min

Cultural Integration and Business Evolution

14min

The Shift to User-Centric Software and Investment Innovations

4min

10.

Navigating Venture Capital Evolution

17min

0:51 Jason intros Bain Capital's Ajay Agarwal
3:17 Are we experiencing late-stage capitalism? Is capitalism broken?
8:22 Why is upward mobility stalling?
15:29 What is it about founders & startups that made him dedicate his life's work to?
18:46 What piece of knowledge got him in startups? Ajay describes gross margin & incremental costs
23:03 Two insights on why enterprise software is the best business
30:11 Mitt Romney at Bain Capital & issues with cultural appropriation
36:44 Ajay's early days at Trilogy Software, how software sales were different in the 1990s
42:23 Companies going from sales-driven culture to product-driven
46:52 Ajay describes one of his best investments: FourKites
49:13 Ajay describes the biggest miss of his anti-portfolio: Pinterest, and why some firms care about stage and some are stage-agnostic
54:57 Has Bain ever participated in every round of a companies life-cycle?
58:15 Effects of the SoftBank Vision Fund on venture capital as a whole

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