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
This is a terrific entrepreneurial story of a woman entrepreneur with no technology background who is killing it with a technology startup. Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? What’s your background? Cooper Harris: I’m from the southeast of the East Coast. I was born in Atlanta
If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. Jyoti started as a first-time entrepreneur trying to do a fat startup. Read how he managed to navigate the chicken and egg, and build a Unicorn-level success. Superb story! Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were