
Community Strategy: How should you engage with your community?
Once you have a community, you have to make decisions on how you wish to engage with them.
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If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.
Excellently navigated journey!
Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, and in what kind of background?
Sameer Maggon: I grew up in Delhi. I did my engineering in Computer Science from Pune. Then I came back to my hometown to work for a document management company. Then I decided to learn more. I came to USC in Los Angeles and did my Masters in Computer Science. Since then, I’ve been in LA and worked in a variety of startups and larger companies in the greater Los Angeles area.
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Online learning has exploded in popularity over the last decade. In Covid, the field has found a tremendous force multiplier.
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I started blogging on Technology Entrepreneurship in April 2005. The Internet was different then. There was no Smartphone. Social Media was just starting. Facebook and LinkedIn were new concepts.
Today, in 2021, building and monetizing a Technology Entrepreneurship Blog requires a very different strategy than the one I started with.
In this multi-part series, I will lay out a fully fleshed out roadmap of how to do so with contemporary tools.
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During this week’s roundtable, we had as our guest Lloyed Lobo, Co-founder and President of Boast.ai, discussing his failures and eventual success building AI startups. Wonderful conversation.
Teleperson
For the entrepreneur pitch, we had Jesse Hollander, from Delray Beach, Florida, pitch Teleperson. Unfortunately, as I have said repeatedly, it is impossible to raise money to build MVPs, and this conversation is yet another iteration of this same flawed assumption that pervades the startup ecosystem.
You can listen to the recording of this roundtable here:

Entrepreneurship is not a career. It is a way of life.
For me, this journey began as a graduate student at MIT in 1994. The world watched Netscape go public that spring, and the Internet swept over us like a virus. As I wrote my Masters thesis, I also wrote my first business plan. We were, as a generation, shaping the Internet during those early years, and, my degree in hand, I was ready to jump into the unknown – from then on really, I have been jumping into unknowns at every turn.
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Most adult professionals have jobs, families, and other responsibilities. People working in the tech industry have big salaries to forego if they want to start a company.
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There are over six million students enrolled in Machine Learning courses on Udemy. The most daring will try to start their own businesses.
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