Chris Ennis

and then I thought “I should really write about some stuff. But nothing from my 20’s. That stuff is reserved strictly for the book.” So, here I am.

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Why B2B Startups are Easy or Hard

I appreciate those who work on hard problems. Scratch that. I admire them. Too often though, I see startups that sell directly to businesses building upon concepts that are unnecessarily hard. In a business you have cost centers and profit centers where most B2B startups fit in with their customers. If you’re in the profit center portion of your customers' business, then good for you. This does not apply to you.

What I am talking about here is B2B products that is a cost center for it’s customers' business. It may lead to greater efficiency and cost savings, but by itself does not generate revenue. My first company was a B2B solution, and at the age of 21 I was learning about this first hand.

Repeat after me. The single hardest product to sell to a business is one that creates a new cost that previously did not exist. You may have built a great solution for...

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HIPAA in a PRISM World

I spend a significant amount of my time as CTO of RxAssurance working with our partners to insure that patient information, commonly referred to as Protected Health Information (or PHI), will never be exposed to anyone other than the individual and the care providers that they have granted consent to. We deal with all types of healthcare executives: the pragmatic, the optimistic, those who wear large tin foil hats and those who are attached at the hip to their legal counsel when it comes to HIPAA.

HIPAA is scary. Not so much because of the bar for securing information that the mandate sets, but for the penalties it levies when a violation occurs. What most don’t know is that the majority of violations have had nothing to do with actual networks and software. Most violations come as a result of misplaced or stolen storage devices, mishandled paperwork and careless front desk processes....

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Twitter No More

This isn’t what you think. I’m not closing my Twitter account. No, this post is addressing something that happened over half a decade ago. In May 2008, I began a side project. While running SoberCircle, I built a Twitter aggregation service that worked solely upon local Twitter users and their networks of followers. The service was called NashMash and indexed the activity of over 30,000 Twitter users in the Nashville market.

Why did I build it? I wanted to play with the Twitter API while growing my local network. I had met Dave Delaney (for those of you who don’t know Dave, check out his book New Business Networking) at SXSW in March 2008 and it was Dave’s strong presence on Twitter that encouraged me to look at Twitter as a means to grow my local connections. Most of my work at that time was with people outside of Nashville, so I didn’t have a strong...

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Sanity Check: Taking Two Small Children to Europe

My wife and I have been talking about going to see friends in Amsterdam for the past year. Originally, we thought about taking our newborn to Europe last May, but finally thought better of that idea. Well, 13+ months after our second son was born, we’ve booked the trip and depart for London on Saturday. WTF were we thinking? A five year old and a one year old on a 11 hour journey from one hemisphere to the other, are we mad? Perhaps.

In 2011, we took our oldest son, who was 2.5 at the time, to Sweden. That worked out reasonably well. So our confidence has been high that we can pull off the feat again, this time with two in tow. In the months since we started planning this trip, I hadn’t thought much of the difficulties traveling with a 13 month old might present. But a recent visit to his pediatrician gave me pause, as he explained to me that a 13 month old that just...

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Feedback First

It’s amazing how much further you can get with a potential investor, especially VCs, if you approach them asking for input. Of course, given their position as rainmakers in the startup world, they are constantly showered with requests to talk. Those talks are often about how great the entrepreneur’s business is and why the investor should give them money.

Of course it’s easy to see how going into that talk looking for feedback first is a refreshing change of pace. More importantly, by asking for input first, you are showing the investor that you are interested more in the value they bring to the company outside of the capital.

I know personally, I’d rather invest in the entrepreneur who is looking to maximize the value of every relationship, understanding that money is the oxygen necessary to run the race, but winning comes down to the strategy of choosing the right pace at the...

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