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Bootstrapping a Cloud Services Business

What does it really take to start a cloud services business? While the headlines glorify those entrepreneurs who rake in millions from VCs, there are plenty of startups that are pulling themselves up by their own bootstraps. They choose to own their destiny and build their business -- usually while holding down a "real" job -- one customer at a time.

Building a Base Through Beta
The idea for Winsitter, a cloud service that monitors Windows servers and delivers alerts to busy admins, evolved from Bret Fisher's own sysadmin experiences. Now CEO of Winsitter, Fisher wrote on the first entry of the company blog, "I thought...what if we took the combined ideas of everyone we knew in the biz of Windows Server engineering and built an analysis engine in the cloud? ... What if the analysis engine does all the wizardry and you just get alerts the way you prefer (e-mail/SMS/Twitter/Facebook/Jabber/phone)?" 

Now in its second year of beta testing, Winsitter has been building a global user base that provides feedback on its functionality and usability. There is currently no charge for the service, but that will change soon -- which will be the real test of the startup.

All of the progress that Fisher and start-up partner Kevin Griffin, Winsitter's CTO, have made to date has been accomplished through time investment, with no outside funding. Like many entrepreneurs, the team works regular jobs to support their startup habit.

As is clear from Winsitter's Web site, Fisher and Griffin have built a strong group of supporters through a culture that invites participation. It's hard not to root for a company that toasts its supporters on the About Us page: "No sysadmin learns everything on his/her own, so cheers (*clink*) to all those who have helped us over the years to be better computer geeks."

Microsoft Support
For most startups, Microsoft is not the platform of choice, but Fisher spent his entire career on Windows and wasn't going to change. The entrepreneurs took the route few others have taken by building their cloud service on Windows Azure with Node.js.

"The majority of recently developed business and personal apps have been on Linux or Mac," Fisher noted. "On the Windows side, we are still playing catch-up. I feel like that culture has been lost in the Microsoft world."

While Microsoft's cloud reselling partner model is clear, finding support for Windows-based Software as a Service (SaaS) solutions is more challenging. As most startup partners know, getting attention from Microsoft team members is not an easy task, but Fisher has found Microsoft's Worldwide Partner Conference (WPC) to be effective.

"If you are a SaaS company, it's key to find the right people in Microsoft to help you," Fisher said. "The way that I have been able to find them has been to attend WPC. One week at WPC is more valuable than a year's worth of e-mails and phone calls."

Fisher made another important discovery while at WPC in Houston this year -- Microsoft's Pinpoint partner directory. During a 20-minute visit to the Pinpoint booth, Fisher worked with the Microsoft reps to build the Winsitter profile. "I am now a big advocate," Fisher said. "Since we set up the profile, we get user adds almost every day." A huge benefit of Pinpoint to the SaaS startup is that, unlike pay-per-click, there is no cost for each customer add.

The Journey Continues
The cloud has broken down barriers to entry, but the journey from startup to sustainable business still follows a long, winding road. From designing an appealing Web site to processing payments in multiple currencies, there are countless issues cloud service businesses need to manage. We'll check back over the next few months with the Winsitter team to share more lessons learned.

How are you building your cloud business? Add a comment below or send me a note and let's share your story.

Posted by Barb Levisay on October 10, 2013