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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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Building a Fast Growth, Cutting-Edge Insurance Brokerage: Karn Saroya, CEO of Cover (Part 1)

Posted on Monday, Oct 22nd

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  This is a terrific story of a team that has tremendous expertise in building and acquiring customers for consumer apps, and how they applied that unfair advantage to disrupt a domain (insurance). Sramana Mitra: Let’s start at the very beginning of your journey. Where are you

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Building a VC-Funded B2C CRM Company From Virginia: Zaius Founder and CTO Spencer Pingry (Part 1)

Posted on Monday, Oct 15th

We love companies that have roots in off-center geographies. Zaius started in Virginia, raised capital in Boston, and has grown to ~500 customers with a $24k average ARR per customer. These are healthy metrics, and for the team in Virginia, accomplishments to be proud of. Sramana Mitra: Let’s start at the very beginning of your

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