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How an IT Services Startup Wants to Disrupt Itself in the AI Era: Sanjay Jupudi, CEO of Qentelli (Part 1)

Posted on Monday, Nov 26th

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  AI will disrupt outsourcing services companies in a very big way. We talk to Sanjay on how he plans to prepare. Sramana Mitra: Let’s go back to the very beginning of your personal journey. Tell me where you’re from, where were you born, raised, and in

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Bootstrapping a Virtual Company to 5 Million Plus: Nick Shaw, CEO of Renaissance Periodization (Part 1)

Posted on Thursday, Nov 8th

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. Nick has built a very interesting e-learning company and addressed scalability with nifty strategic choices. Read on. You’ll learn a lot. 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

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Bootstrapping with Paycheck to $15 Million from Tennessee: Gene Caballero, CEO of GreenPal (Part 2)

Posted on Tuesday, Oct 30th

Sramana Mitra: Did you start this as a bootstrapped company? Gene Caballero: Yes. We aggregated about $100,000 between the co-founders. We blew that by paying a custom shop to build us a website and a couple of apps. After about a year and a half of not getting what we want, they turned over a

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Bootstrapping with Paycheck to $15 Million from Tennessee: Gene Caballero, CEO of GreenPal (Part 1)

Posted on Monday, Oct 29th

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  This is a fantastic story of a founder duo bootstrapping with a paycheck, now growing from $5M to $15M in one year, with a virtual team of freelancers. Your classic 21st century internet business. No outside financing whatsoever! Sramana Mitra: Let’s start at the very beginning

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Building a Fast Growth, Cutting-Edge Insurance Brokerage: Karn Saroya, CEO of Cover (Part 4)

Posted on Thursday, Oct 25th

Sramana Mitra: There’s some reason why you were drawn to insurance? Why insurance? Karn Saroya: When we were running Stylekick, we worked with some insurance brokers. One day, I walked into one of their offices. This was in Toronto in the financial district. They had multiple floors wedged between investment banks, consulting firms, and private

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Capital Efficient Entrepreneurship: Neil Vaswani, CEO of Corestream (Part 3)

Posted on Wednesday, Oct 24th

Sramana Mitra: How did you get it off the ground? You said you raised money right away? Neil Vaswani: Yes. My co-founder and I wrote up a two-page executive summary. We started spamming VCs. We got some calls back. Sramana Mitra: What year was this happening? Neil Vaswani: This is 2005. Not exactly the best

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Building a Fast Growth, Cutting-Edge Insurance Brokerage: Karn Saroya, CEO of Cover (Part 2)

Posted on Tuesday, Oct 23rd

Karn Saroya: Ultimately, we were acqui-hired at Shopify. We got to build all sorts of interesting things. We worked on the Facebook Messenger chat bot for commerce. We got to work with Toby a little bit. Having been there for a couple of months, we still had the itch. We decided that we wanted to

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Capital Efficient Entrepreneurship: Neil Vaswani, CEO of Corestream (Part 1)

Posted on Monday, Oct 22nd

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  Neil has turned a $3M investment into a ~$10M annual revenue company by addressing a cumbersome piece of workflow in benefits management. Read on to learn how. Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born,

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