Featured Startup – Dialawg, LLC

Today’s featured Indiana startup business is Dialawg, LLC, a startup that provides a service that is near and dear to my nerdy attorney heart.  Attorneys have all sorts of ethical obligations to keep client communications confidential / top secret.  Some communications and documents are obviously more sensitive than others.  Email is by far the dominant way for attorneys (and anyone for that matter) to distribute information – but it is not always the most secure way to do it.  That is where Dialawg comes in – it provides a secure online platform for attorneys to share sensitive information with clients and other people – and keep in line with ethical requirements.  I just met these guys recently, and plan on giving it a whirl in my practice.

Tell us about your startup…your words…whatever you want to say.

Dialawg allows important conversations to be had online in a private, trackable, and organized manner.  We are a two-person, Indiana-based startup with a wholly-owned Canadian subsidiary.  Our clients simply “start a Dialawg” and then post messages, files, and form submissions as they like. Participants can be added at any point and receive access to everything in the Dialawg.  Features like real-time chat, simple conference calls, and IMAP integration make keeping people connected easy, and at the end of the day, a PDF audit report can be downloaded to verify activity within the conversation.

How did you come up with concept for your business, and how/when did the business model for that concept become clear?

My co-founder, Jeff, has been an attorney for about seven years.  After a few years of practice, he noticed the disturbingly commonplace use of unencrypted email to distribute highly sensitive information to clients, and he approached me with the idea of building an end-to-end encrypted system for transmitting messages and files.  We began by targeting the legal community with a simple solution, and soon realized that we had an opportunity to revolutionize the digital conversation for everyone.

What made you first believe that starting a business is right for you (i.e. as opposed to working for someone else)

I’ve been a creator since I was a kid: one of my first inventions was a reusable band-aid (which wasn’t such a big hit with adult audiences), and the clubs I started with my friends collected taxes and had loan services. I always knew that I’d have to run my own business to be truly satisfied, and every professional move I’ve made since has been another step in that direction. For me, having my own business is just about finding equilibrium.

What challenges have you encountered?

The biggest challenge for us has been getting the word out. As a small, largely self-funded operation, we haven’t had the luxury of hiring a lot of staff or making expensive marketing moves. We have to balance sales, marketing, and basic business activities with building a fantastic product. We were in operation for over two years before our system led us to the realization that context was the missing ingredient and that our customers should be starting “Dialawgs” with each other. Although staying so busy with the day-to-day operations has sometimes prevented us from being able to spend a lot of resources on reaching a wider audience, our hard work is now apparent in our solid, stable platform.

What sacrifices have you made to start your business?

Since we don’t have rich uncles or piles of gold in our garages, we’ve had to simplify our lifestyles and sometimes take on additional work when necessary. Before Dialawg, I had been working on another startup for almost three years. The long nights of coding are over (there’s only so long you can physically keep that up), but I’ve been hitting things extremely hard for over five years now. I’ve learned a lot about patience, humility, and the importance of a life-work balance.

In your opinion, what makes Indiana a great place to start your business?

The low cost of living and high quality of available services in Indiana has been a big benefit to our company–running an operation as ambitious as Dialawg on such limited inputs may not have been as possible in the Valley.

If you could give an entrepreneur looking to start a business one piece of advice…what would it be?

Patience and honesty are critical. Starting a business is relatively easy, but sticking it out and refining your work into something truly remarkable always seems to take longer than you might expect. Without being honest with yourself you can’t build a great product, and without being honest with your customers, you can’t expect reliable revenue.


Stat Sheet: Dialawg


  • Business Name: Dialawg, LLC
  • Website: www.dialawg.com
  • Facebook Fan Page (if applicable): http://www.facebook.com/pages/Dialawg/39955629978
  • Twitter Account (if applicable):@dialawg
  • Your title at the business: Colin Mathews, Co-Founder and Chief Technologist
  • When was the business founded: Winter ’08-’09
  • Business Description in 140 characters or less: Dialawg allows you to have a private conversation, accessible from anywhere, where parties may easily exchange messages, share files and collaborate on documents

Categorized: Featured Indiana Startups

One Response to “Featured Startup – Dialawg, LLC”

  1. Thank you, Brian for the interview — it was a pleasure!


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