Building a Venture Scale AI Company: Observe.AI CEO Swapnil Jain (Part 2)

Sramana Mitra: What was the idea that you zeroed in on? What was the process?

Swapnil Jain: It was a pretty long process that lasted two years. Towards the last two days of my job, I started formalizing some ideas. More often than not, you pivot. I started with one idea. I had eight different ideas during that period. I’d test and idea; if it’s working, keep moving forward. If not, then pull back.

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Building a Venture Scale AI Company: Observe.AI CEO Swapnil Jain (Part 1)

Swapnil makes a very clear distinction between his goal of becoming a Centaur ($100M+ revenue company), not a Unicorn ($1B+ valuation). Read on to learn about his journey.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born and raised? What kind of background?

Best of Bootstrapping: Startups Die From Overfunding

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

Funding = Success, right? I wish it did. But entrepreneurial tracks are littered with carcasses of dead startups that were very well funded, some to the tune of hundreds of millions. As a case in point, watch this 2 minutes 31 second video: Death By Overfunding.

If you prefer to read instead of watching, read the Nasty Gal story here:

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Cloud Stocks: Alphabet Bets on AI

Alphabet aka Google (Nasdaq: GOOG) recently reported its third quarter results that surpassed market expectations. Like Meta, Google is also benefiting from a rebound in digital advertising spend. Despite the growth, the market was not too pleased with the outlook that the company provided, sending its stock falling 7% in the extended trading session.

Best of Bootstrapping: Bootstrapped a Global E-commerce Venture to $50M

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

When we spoke in 2018, SmartBuyGlasses Co-CEO David Menning had bootstrapped a global e-commerce venture from Hong Kong to $50M. Splendid execution!

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

David Menning: I grew up in Sydney. I’ve been educated in Australia. In my later years, I studied at universities overseas both in Canada and Japan for a little while. It was this time when I was abroad spending time in different countries that I was exposed to different business models, cultures, and people.

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Thursday, November 9 – 625th 1Mby1M Mentoring Roundtable for Entrepreneurs

Entrepreneurs are invited to the 625th FREE online 1Mby1M Mentoring Roundtable on Thursday, November 9, 2023, at 8 a.m. PST/11 a.m. EST/5 p.m. CET/9:30 p.m. India IST.

If you are a serious entrepreneur, register to “pitch” and sell your business idea. You’ll receive straightforward feedback, advice on next steps, and answers to any of your questions. Others can register to “attend” to watch, learn, and interact through the online chat.

You can learn more here and REGISTER TO PITCH OR ATTEND HERE. Register and you will receive the recording by email, even if you are unable to attend. Please share with any entrepreneurs in your circle who may be interested. All are welcome!

Best of Bootstrapping: Bootstrapped and Pivoted from the US Midwest

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

Co-founder and CEO Paroon Chadha has bootstrapped Passageways from Indiana, now doing business as OnBoard based in Milwaukee, Wisconsin, and he wants to help other regional entrepreneurs succeed. Along the way, he has pivoted from licensed software to cloud software, and made other strategic decisions that helped his company become more successful. Read our conversation from 2018 to learn more on his moves.

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

Paroon Chadha: I was born in Chandigarh, India. I was born to a family of entrepreneurs. Growing up, the choices basically boiled down to being an engineer and then perhaps being an entrepreneur. I went to Punjab Engineering College and found myself a little bit at odds with technical internships that I did and felt like sales was my true calling. It was mostly influenced by some of my mentors in life. My dad ran businesses. It led me to join a sales job out of engineering. My first job was at Wipro. I sourced hardware and software solutions for two years in India. That’s how it started.

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Colors: Harvest II

I’m publishing this series on LinkedIn called Colors to explore a topic that I care deeply about: the Renaissance Mind. I am just as passionate about entrepreneurship, technology, and business, as I am about art and culture. In this series, I will typically publish a piece of art – one of my paintings – and I request you to spend a minute or two deeply meditating on it. I urge you to watch your feelings, thoughts, reactions to the piece, and write what comes to you, what thoughts it triggers, in the dialog area. Let us see what stimulation this interaction yields. For today – Harvest II

Harvest II | Sramana Mitra, 2021 | Watercolor, Pastel, Brush Pen | 8  x 8, On Paper