How To Moonlight Effectively And Keep Your Day Job

Here’s how the founding team of Straw developed their idea and stayed on track at their day jobs at Microsoft.

How To Moonlight Effectively And Keep Your Day Job
[Photo: Flickr user Al Ibrahim]

It started with a debate among friends.


At a New Year’s Eve party, four guys were discussing college football bowl games, complete with posturing about favorite teams. But separating smack talk from stats on who would have a better chance of winning proved more elusive. Posting a question on Twitter or Facebook can potentially elicit a ton of replies. But just as often, the discussion generated descends into digressions or not very useful information.

The debate would have stayed in the social media realm if the four friends hadn’t also been co-workers at Microsoft with experience in engineering, design, user experience, marketing, and sales. So Ben Rudolph, Craig Kitterman, Nate Gunderson and Jason Wilmot pooled their collective knowledge to design a way to poll friends about any topic across social networks.

Working at their regular jobs by day and their new application at night, they created Straw in March of 2014. Rudolph tells Fast Company that Microsoft actually encourages this kind of moonlighting. “A few years ago, the company began encouraging employees to build apps for the Windows ecosystem in their spare time, and offered up a number of resources and tools,” he says. Other companies, both large and small, do this to foster innovation.

The Straw Team (L to R) Craig Kitterman, Jason Wilmot, Ben Rudolph, Nate GundersonPhoto: Genevieve Ruth Photograpy

In this way, Straw 1.0 launched seven months after that New Year’s Eve party. Even though Straw isn’t a Microsoft project, Rudolph says it’s fully Microsoft powered, which explains why it launched on Windows Phone first and didn’t make an iOS and Android debut for another month. The mobile apps were built on the .NET stack with Microsoft developer tools and the back-end services are running in the Microsoft Azure cloud.

This June saw the release of Straw 2.0 with StrawCast, which allows users to broadcast their polls to all other users of the Straw app in addition to their social networks. In its first week, over 1,000 polls were posted. Overall, Straw has more than 10,000 active users and logged nearly 500,000 poll votes to date, according to the company.

Though the progress was swift, Rudolph says that it was a balancing act to work between day job and passion project–especially in the exciting early stages. He believes in the power of planning how you want to spend the next 24 hours. “Everyone lives in a world where they have competing priorities–work, family, fitness, hobbies, etc. Straw is one of those priorities for us. We all have important, rewarding, challenging day jobs at Microsoft that keep us very busy, and we all have spouses and kids who are a huge part of our lives,” he admits.


That said, Rudolph maintains that everyone works on Straw every single day. “But we don’t do it at the expense of the other two,” he asserts. “It may mean getting up a little bit earlier, going to bed a little bit later, and watching a little less TV–but we’re OK relying on coffee and DVRs if it means we can make Straw a success,” he says.

Staying on track as an independent team could also prove tricky when there is no corporate oversight and only yourself to answer to. It’s often the thing that makes passion projects languish or fail to launch at all. Rudolph says the founding team had a sense of mutual accountability that kept them on track. “No one wants to let anyone else on the team down,” he says, in large part because not only do they all work together, but they are all also neighbors and their children play together. “If you’re the one who slips up–there’s nowhere to hide,” he adds.

But it’s bigger than just the four of them, Rudolph believes. “Straw will only succeed if our users love using it, and they’ll only love using it if we’re continuously working and innovating,” he explains. “Knowing that slacking off means potentially disappointing thousands of people around the world is a pretty powerful motivator.”

To meet goals, Rudolph says the team relies on communication, documentation, and meetings.

To communicate, they are devoted users of Slack. The platform allows them to chat in real time and offers them a central place to store ideas. “If someone has a lightning strike of an idea on a lunch break, there’s no, ‘Oh, I’ll write that to the guys in email later.’ It immediately goes into Slack,” Rudolph says.


To document everything from engineering to design to marketing, the team uses (no surprise) Microsoft’s Visual Studio Online, which integrates into Slack. “This is how we assign work items and deadlines and ensure that nothing, not even the most minor UI tweak or bug fix, gets missed,” he says.

Getting together is equally important, says Rudolph and they have a standing weekly meeting on Thursday nights, without exception. “If one of us is traveling (as we often are), we Skype in,” he says, “This is where we assess progress, prioritize work and have deep discussions about Straw’s future.”

About the author

Lydia Dishman is a reporter writing about the intersection of tech, leadership, and innovation. She is a regular contributor to Fast Company and has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.