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dan stewart
Best of Bootstrapping: Bootstrapped to an Inflection Point
If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. Happy Grasshopper CEO Dan Stewart was a 1Mby1M entrepreneur when we spoke in 2017. Read how he navigated his way to an inflection point that brought him to the cusp of 4x growth. Sramana Mitra: Let’s start at the very beginning of your journey. Where are
Best of Bootstrapping: Happy Grasshopper CEO Dan Stewart Bootstrapped to Inflection
If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. Dan Stewart was a 1Mby1M entrepreneur when we spoke in 2017. Read how he navigated his way to an inflection point that brought him to the cusp of 4x growth. Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where
Bootstrapping to Inflection: Dan Stewart, CEO of Happy Grasshopper (Part 7)
Sramana Mitra: What was the inflection point? I remember there was a channel-based inflection point that you were able to hit upon as well, right? Dan Stewart: It was the introduction of the custom-writing services that caused the spike in our revenues. Instead of providing a single message that they can send once per month,
Bootstrapping to Inflection: Dan Stewart, CEO of Happy Grasshopper (Part 6)
Sramana Mitra: Talk a bit about the ramp in customers. What was the first year and how did it grow from there? Dan Stewart: In the first year, we ended up with tens of clients from the real estate coach who was talking about our service. Somehow, a very prominent real estate agent up in
Bootstrapping to Inflection: Dan Stewart, CEO of Happy Grasshopper (Part 5)
Sramana Mitra: When you and I started working together and we were looking for the positioning, that was very much our conclusion. It’s okay to cater to people who are coming as inbound leads and are a fit for the technology and product. But from an outbound marketing point of view, you have to pick
Bootstrapping to Inflection: Dan Stewart, CEO of Happy Grasshopper (Part 4)
Sramana Mitra: How many years was the CRM company? Dan Stewart: Three years. Sramana Mitra: How much did you sell it for and to whom? Dan Stewart: That’s all really confidential. It wasn’t a sexy exit. Our largest customer did not want us to sell to their competitors. They basically bought a license of the code and
Bootstrapping to Inflection: Dan Stewart, CEO of Happy Grasshopper (Part 3)
Sramana Mitra: Your background was in sales training and then construction. Where does CRM come from into this process? Dan Stewart: Maybe we should go back a little bit further. We all have our gifts and talents. I’ve always been fascinated with learning. I have a very diverse set of interests. Whenever a subject interests me,
Bootstrapping to Inflection: Dan Stewart, CEO of Happy Grasshopper (Part 2)
Sramana Mitra: When you decided to shut that down, what was the next move? Dan Stewart: I went to work for one of my yellow pages clients. I became a construction manager of all things. That was a great experience because I got to sell millions of dollars worth of projects. In the process, I
