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
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
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
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
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
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,
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
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