Yesterday TechCrunch posted an article about a blog written by someone at Microsoft which was eventually yanked. The blog post was a tongue in cheek father vs son debate about the differences between Office 365 and Google Apps. Putting the post aside, I thought it was a good opportunity to write about my experiences on this topic.

Placing your bets on Enterprise Software

At Unikrn we are a distributed team, with people in San Francisco, Sydney, Ottawa, Berlin, and Seattle. We also have investors from around the world that we need to share certain documents with. So even though we've been in operation for less than two months, we still struggled with our decisions on technology. What software should we use to operate to our business, what collaboration software should we use, how do we brainstorm on documents, and what do we use for email. Basically it boiled down to three things that we didn't want to think about past the first month;

  • Office 365 vs Google Docs
  • Yammer vs Slack vs others
  • Azure vs AWS vs Google vs Rackspace / Self Hosted

For this blog I’m going to focus on #1, perhaps I’ll discuss the other topics at another time.

Office 365 vs Google Apps

The first thing any startup has to do is setup their domain, and choose their email provider. No one wants to build their own mail server infrastructure anymore, it simply doesn't make sense. Being a Microsoft fan I was initially all about choosing Office 365, but this would prove to be a difficult decision.

I really see the value in Office 365 - it's pretty awesome - we tried both Google Apps and Microsoft Office 365 - giving both 2 weeks of dedicated (forced) use. Both are super easy to setup and administer, you can buy your domain and get your email up and running within minutes. After everyone had a chance to use both we came back with the same conclusion, Google Apps is the best solution for our company.

Our decision had nothing to do with cost because the fact is both work out to about the same price at the end of the day. The decision all boiled down to one thing: Gmail.

Gmail is the Gateway Drug for Google Apps and Google knows this

Office 365 mail is not the same as for some reason. Gmail is the only cross platform cloud email that allows for instant search, massive archives, ease of use, etc. You don't need to download an email client to use it ... and there's better than instant cloud search vs local search for any email ever in a large archives. There are also many third party cloud plugins that just work with Gmail. Gmail is universally the same across all devices, and thus it is the gateway drug to Google Apps.

Once you start working with the productivity tools you realize that calendaring on Outlook is much better than Google Apps. Excel, PowerPoint, and Word all beat Sheets, Slides, and Docs hands down. Things like font management, financial modeling, and effective presentations are all Office 365 all day long.

Real time collaboration on Google is better, you can tell it was built from the cloud up. Google Drive is much easier to administer than OneDrive. Google makes it very easy to share, search, and access documents from virtually any device, anywhere. Drive has quickly become the core of everything we do in our business. SharePoint almost felt like a bolt-on to Office 365, and trying to rationalize the difference between SharePoint, Yammer, and OneDrive just felt weird for the people on our team. Both companies continue to improve their products which is always nice to see.

Microsoft Office 365 could gain significant ground with startups by doing one thing

We may not be “enterprise class” companies, but today's startups are indeed tomorrow’s large companies. Microsoft needs to get more people at every accelerator and co-working space using Office 365 without even thinking about it. They need to make it easy and automated so the growth happens organically rather than through sales motions, pr, or blog posts. People just have to want to use it “just because”.

So how does Microsoft drive immediate usage and significant startup interest to Office 365 Apps like Word, PowerPoint, and Excel? They need to make it fully compatible with Google Apps. They should create a third party app for Google Apps, fully compatible with Drive, Gmail, and Adobe Acrobat Reader. If Microsoft can introduce better calendaring for Gmail, with integrated Skype and/or Hangouts support, that would be a huge bonus. They should make it free for 90 days, and charge a reasonable subscription fee thereafter. I can imagine many people would jump on this - us included. In fact I’d love to hear from entrepreneurs out there - if you agree say something in the comments!

We, like many startups, will likely not switch email providers at this point, Gmail is just too simple and too good to cancel - but we’re more than happy to add on quality apps that make our workforce more productive. Basically I'm saying I'm not sure it makes sense to wage war against established ecosystems. Instead, Microsoft should embrace other established ecosystems with what they do best. Office Apps are awesome, but Outlook/OWA/Exchange is just not as simple or universal as Gmail.

FWIW I used to work at Microsoft Ventures. I love the company, and I know they will continue to improve their offerings to make it better for startups. I remain a fan of the company and the direction they're going.