Back to Our Roots: Productivity in Microsoft Outlook

It is with great emotion and excitement that we are announcing a major shift in our business.  The DotAlign social web application will soon be shut down.  We are grateful to our beta users and deeply regret that we cannot support the application going forward. Instead, we will focus on productivity and relationship intelligence within Microsoft Outlook. If you are familiar with the Microsoft Office tools built by my prior startup, DealMaven, our plan is to deliver similarly valuable tools for Outlook. Here is the story behind our transition, along with lessons learned.

B2C Social Challenges

Per my recent TED talk, I believe fervently that social networks have tremendous untapped potential value for professionals. Over the past couple years, I’ve/we’ve tried a couple different approaches to unlock this value but encountered key obstacles:

  1. Chicken & Egg: OpSpark, the predecessor to DotAlign, was an invite-only social network for highly credentialed professionals. In a world of social network fatigue, creating a new network proved incredibly difficult. We pivoted to DotAlign as a tool that gets value from existing networks rather than creating a new one. However, DotAlign encountered the next two challenges.
  2. Competing Social CRMs: Many startups have emerged, including some with serious funding, to bring together contacts from across different networks. It has been hard enough to cut through the noise when pitching VCs and we saw that as a sign that marketing the finished product (even a free one) to customers would be equally difficult.
  3. Email is Here to Stay: For me, Social CRM was always just the first step toward a meaningful sharing of information among related professionals. My LinkedIn social stream is of limited value today, mostly filled with commodity information that my contacts feel comfortable sharing publicly. The goal of DotAlign (and OpSpark) was to enable private conversations among smaller sets of relevant people. No matter what its advantages, however, the fact is that we were requiring a behavior change in moving these conversations out of email. This got us thinking further about use of email as an opportunity.

B2B – Meanwhile, Clients Need Our Help

My last startup, DealMaven, provided productivity tools for PowerPoint and Excel. Former clients and others have told us their firms desperately need similar tools for Microsoft Outlook. Considering that our CTO even worked on the Outlook team at Microsoft, we see this as a natural direction for DotAlign.

We understand Gmail and mobile are important to email too, and we may build solutions there in the future. However, for the customers we are targeting, it all begins with Outlook. Bankers, lawyers, and other high-end professionals don’t just sell, they manage relationships.  They use Outlook, and there are gaps in existing tools and traditional cloud-based CRM relative to their needs (including regulatory compliance issues).

If you find managing your inbox and your contact relationships to be a tedious, stressful experience, we plan to delight you. If your firm is exploring solutions in this area, let us tell you about the features we are building (and soon you can try them). Just reach out to team(at) We also welcome your ideas for features, and will give a free copy of the app to the most helpful contributors.

Lessons for Fellow Entrepreneurs

I understand why I made the mistakes I did. DealMaven improved quality of life and productivity for 10,000 professionals working in PowerPoint and Excel. It was a solid success for investors, employees, and stakeholders. But this time, I wanted to build a business with a greater societal impact. The goal with DotAlign wasn’t just to organize social contacts, it was to set up ways that professionals could help each other “connect the dots” toward opportunities (deals, investments, jobs, clients, etc.).

I still dream of changing the world and boosting overall economic productivity, and I still believe that DotAlign, Inc. will have that impact. But rather than starting with a free B2C web application and later finding ways to monetize it, we will instead delight paying customers and then find ways to create an impact beyond our initial base. If there is unlimited financing, I suppose either route can work. But I’m no longer interested in courting VCs. From now on, we’re courting customers.

3 thoughts on “Back to Our Roots: Productivity in Microsoft Outlook

  1. Vince, that is a tough decision, but one well made. I had a super idea related to email that I took to London law firms at the time the global financial crisis hit — wish I knew how to move it forward!

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