Sashi Reddi was born in Madras, today known as Chennai, India. He graduated with a Bachelors in Computer Science and Engineering from the Indian Institute of Technology (Delhi), a Masters of Computer Science from NYU and a PhD in Operations and Information Management from UPenn (Wharton). Over 30 years ago, Sashi seized the opportunity to move to the US and began putting down roots there. He shares his journey of entrepreneurship from the web content management space with EZPower Systems, to the software testing space with AppLabs, to the investment sphere with SRI Capital. Sashi provides insights into what India was like when he was growing up in terms of technology, economy, and opportunity, as well as how things have changed over the years. Tune in to find out more about Sashi’s current investment projects, and his thoughts about the lessons he has learned over the years.

Key Takeaways:

[2:58] Kevin does a speed round with Sashi Reddi. [7:51] Sashi has an impressive educational background. He shares more about his educational trajectory from India to the US to his PhD. [12:49] What was the economic, technological, and enthronement in India like when Sashi was growing up there? [15:34] How did Sashi decide to stay "where he was planted" on the East Coast instead of heading to the site of action as the Internet was being born? [18:40] Why did Sashi decide to exit his web content management company so quickly, and why was he attracted to DocuCorp? [20:46] When did Sashi start AppLabs? [21:50] What was the problem Sashi was trying to solve with AppLabs and how did he approach it? [24:30] How was AppLabs structured? [27:28] What were some challenges AppLabs faced in convincing Sequoia? [29:16] How did Sashi grow his company from 5 employees to 2500 employees, from $10 million to $110 million in such a short time? [31:46] Sashi shares some of his insights from working in a large company. [33:11] Sashi entered the world of investments with SRI Capital. What elements does Sashi look for in his investment decisions? He shares his process of investing from his family office to starting SRI Capital. [38:05] What is a strong offline customer acquisition strategy? [40:58] Sashi explains more about Fakespot. [45:33] Kevin and Sashi discuss the potential of Foyr. [48:15] Another of Sashi's investments is SoftWear Automation Inc. [50:35] What is TiE? [53:57] What is the story behind Sashi's investment in Thinci? [59:42] What is Sashi's involvement in the consumer tech space? [1:06:11] What are LetsMD and FITSO? Sashi explains how they are business models that may not work in the US but make perfect sense in the Indian market. [1:11:58] Indian Money is a financial advisory services company in India, which clearly shows the scale of the market in India. [1:14:17] What is the story behind PhenomPeople, a local success story? [1:15:29] As Sashi looks back on the past 20 years, who was a major influencer or inspiration? [1:17:23] What is Sashi's opinion on whether entrepreneurs are born or made? [1:18:48] How does Sashi feel about investing in an entrepreneur's dreams but not being able to interfere?

Links:

Sashi Reddi

Benjamin Franklin: An American Life, by Walter Isaacson

DropBox

Sequoia

WestBridge

SRI Capital

Dollar Shave Club

DollarShaveClub.com - Our Blades Are F***ing Great, on YouTube

Fakespot

Foyr

Softwear Automation Inc.

TiE

Thinci

HealthifyMe

LetsMD

Fitso

IndianMoney Hyderabad Angels Phenom People Vinod Khosla How I Built This podcast James Dyson