Bootstrapping to $15 Million in Three Years: Connatix CEO David Kashak (Part 1)

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. Extraordinarily tight, disciplined strategy and execution has enabled David to build a tremendously fast growth company with a small team. A lot to learn! Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in

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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,

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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

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Bootstrapping Using Services: James Kane, CEO of RWS (Part 5)

Sramana Mitra: How did revenue ramp during this two-year period? James Kane: We went from about $500,000 to a little under $3 million. Sramana Mitra: That brings us to what? 2008? James Kane: Yes, roughly speaking – about when the housing crash started. Sramana Mitra: How did that impact your business?

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

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Bootstrapping Using Services: James Kane, CEO of RWS (Part 4)

Sramana Mitra: As you identified that opportunity, what then did you do to execute on it? What changed? James Kane: We identified that the opportunity was significantly large here. We then reimagined the company to pursue a much larger opportunity. We moved the business from a small, sleepy college town in New York to Phoenix,

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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

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Bootstrapping Using Services: James Kane, CEO of RWS (Part 3)

Sramana Mitra: What was specifically the customer acquisition strategy? Were you calling these people? Were you visiting these people? Was it direct? Was it channel? How did you sell? James Kane: The primary customer acquisition strategy was in-person sales at trade shows. The appliance retailing industry is cyclical. They have two buying seasons – in the late

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