Startup Story: Charlie Kindel on Leaving MSFT, Rolling Out MileLogr

When Charlie Kindel left Microsoft in August 2011, he did what plenty of critics say is too rare for refugees from Redmond: He started his own technology company.

In a 21-year career at Microsoft (NASDAQ: MSFT), Kindel had plenty of experience building digital products and services, including Internet Explorer 3.0, Windows Media Center, Windows Home Server, and Windows Phone 7.

Getting those projects to succeed certainly took skill, vision, and a healthy dose of gumption. But doing it outside the walls of an industry titan with billions of dollars in profits is another thing altogether.

“For me, it’s about proving to myself that I can do these things without the huge organization as a backstop,” Kindel says.

Today, Kindel and co-founder Stefan Negritoiu are running MileLogr. It’s an online application that plugs into digital calendars to figure out how many work-related miles have been racked up on a user’s personal car, to help make it easier for people to track work expenses.

MileLogr has already landed some paying customers, and if it’s successful, there could be plenty more opportunities ahead for the parent company, called BizLogr. Before they get there, I called Kindel up to hear about the experience so far as a newbie entrepreneur. Here’s what he told me:


“When I did startups at Microsoft, I had to go and beat down the bushes for VC within Microsoft, and I had to go through all the gates. In many ways, there are parallels within parts of Microsoft or a big company for how you do that. But once I got started and I got that first little bit of funding and I was able to hire someone … well, that person came with a desk and a healthcare plan and a phone on their desk and a computer.

When you’re doing a startup, you don’t get any of those things. And actually, you can’t even pay someone a salary, which is even further away. So knowing that was the case, but not having actually done it, meant a lot to me.

It was a merit badge, if you will, that I wanted to earn. You don’t earn the merit badge by reading books about how to do something. You earn merit badges by actually doing them and demonstrating you can do them.”

“On one dimension, it’s so much smaller. At Microsoft, it isn’t even considered a business unless it’s got a clear pathway to being a $1 billion business. The product that I built at Microsoft that I’m the most personally proud of (Windows Home Server) ended up being a $30 million a year business.

I was this total unicorn at Microsoft for having pulled that off. And it was wildly successful after three years—if it would have been anywhere but within Microsoft. But at $30 million, you know, it’s just mouse ears.

While there’s great ambition around the underlying business that we can build over time, MileLogr is still at a much smaller scale than most Microsoft business problems.”

“The startup that I was running before I began focusing on MileLogr … we did believe we were going after an exit, and it was a very bodacious thing. [Editor’s note: This startup was an outdoor advertising business focused on youth sports.]

The merit badge I got through that was the merit badge of a failed startup. Which is valuable and thrilling and frustrating, but a very different merit badge.

For someone coming out of Microsoft, who’d been at Microsoft for 21 years, I think it’s pretty valuable to have. So I’m sort of proud of it in a weird way.

We actually built the technology. I had a VP of engineering, I was CTO. My CEO was drumming up money and we just … it was a very capital-intensive initiative to get started the way that we wanted to do it. I think that was one of the mistakes we made.

We simply got to the altar with funding multiple times and just couldn’t get the final deal signed. The money never showed up in the bank.”

“My mom died about this time last year. We went through her storage unit and there was a big box that was full of her old tax returns. And right next to it was a box that was full of her old calendars. And she kept those because they were records of what she had done.

You take that—OK, calendars can go back in time, they can provide you with valuable information about what’s come before. You add to that this other thing that I learned as I was building the prototype, which is all of these calendar systems talk a different protocol.

There’s no standardization for how you access someone’s online digital calendar. Exchange does it one way, Google does it a different way. Yahoo and Apple share the same fundamental protocol, but there are still differences. And does it even differently.

I went looking for some open-source or some library that would simplify this. And I couldn’t … Next Page »

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