1Mby1M AI Investor Forum: Angel Investor Raju Reddy (Part 5)

Sramana Mitra: What else are you looking at, thinking about, interested in investing in in terms of AI companies? What are you looking for?

Raju Reddy: For me, Sramana, pretty much all my investments have been at a very early seed stage.

673rd 1Mby1M Entrepreneurship Podcast with Angel Investor Raju Reddy

Entrepreneur, Angel Investor, and Board Member Raju Reddy discusses his AI investment thesis.

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Best of Bootstrapping: Scaled with Angel Money in Canada

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. 

When we spoke in 2015, Joel Lessem was scaling a profitable company in Toronto called Firmex, and had only spent $4 million in angel money to get to almost $10 million in revenue. Datasite acquired Firmex in 2021.

Sramana Mitra: Let’s start with the very beginning of your story. Where are you from? Where were you born, raised, and in what kind of background?

Joel Lessem: I was born in Israel but raised in Toronto from the age of three. I grew up in Toronto.

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577th 1Mby1M Entrepreneurship Podcast with Chandrashekar Kupperi, Peaceful Progress Fund

Chandrashekar Kupperi is General Partner at Peaceful Progress Fund, an angel fund in India. We have some very interesting discussions on consumer startups in India, especially the ones targeting lower economic strata consumers.

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1Mby1M Virtual Accelerator Investor Forum: With Steve Eskenazi, Angel Investor (Part 4)

Sramana Mitra: I was talking to Eric Benhamou two days ago. He was like, “I’m looking for a good application or use case for NFT.” What about exits? What have you seen through your investments?

Steve Eskenazi: I think there are a couple of tried and true methodologies. I think the best company gets bought and not sold. You have to build companies the right way and you have to scale them the right way. Throwing money at problems is not a solution.

1Mby1M Virtual Accelerator Investor Forum: With Steve Eskenazi, Angel Investor (Part 3)

Sramana Mitra: Here’s a trend question. You have watched the music business for a long time. What is your analysis of the music business? We see music deals from time to time. A lot of the industry believes that you can’t make money in the music business. Can you talk about that?

Steve Eskenazi: I don’t look at it as binary. Some people say you can’t make money. I think it’s very selectively investable. That has been my approach. I was a private investor in Spotify as well. I’ve raised the bar on music deals more than I would in other spaces. I would probably agree that it’s really tough to make money in the music space.

1Mby1M Virtual Accelerator Investor Forum: With Steve Eskenazi, Angel Investor (Part 1)

Steve Eskenazi is an Angel Investor, and we had a number of interesting trend conversations.

Sramana Mitra: Let’s start with a little bit of your background. Tell us about what path you have traveled.

Steve Eskenazi: My career has three distinct phases. In the 1990s, I was Wall Street’s digital media analyst introducing Wall Street to companies like America Online and Electronic Arts. For the next 10 years, I was a venture capitalist for a firm called Walden VC where we invested in internet, SaaS, and digital media companies.

1Mby1M Virtual Accelerator Investor Forum: With Steve Eskenazi, Angel Investor (Part 2)

Sramana Mitra: Let’s do some more examples of the kinds of companies you like to invest in. Is Resonato an IT investment?

Steve Eskenazi: It’s a technology company that occupies the intersection of technology and consumer electronics. Our first TVs were thick. Now, TVs are very thin. They are doing for the speaker market what was done to the TV market. They are making flat-core speakers. They don’t make the speakers. They license their technology. They’re heavily patent-protected.