185 Days Later

Zombie Walk 2010

It’s been like a great zombie movie. There’s interesting zombies, lots of gore, non-cliche characters, man vs zombie, and at least one human idiot (hello, my name is David).

Actually it’s been an amazing 185 days (just over 6 months) since I announced that I was leaving Microsoft.

MSFT 9-24-2010 thru 3-24-2011

The good news is that as a Microsoft shareholder, my departure did not appear to greatly affect Microsoft’s stock performance (closed Sept 20, 2010 at 25.13 vs Mar 23, 2011 at 25.81). This means technically my leaving added 68 cents a share. While my giant ego would be incredibly bruised being the cause of $5.712B increase in value because of my departure (8.40B shares outstanding *  $0.68/share change). I am pretty sure that most of this change is unrelated to me, and more related to Kinect, Phone 7, and other product sales performance). But as an egomaniac, I’ll claim I’ve added $5.7B of value to the economy ;-). But I digress.

I found a co-founder. We started a company. We’ve hired a team. We’re raising money. We’ve built a product. Talked to potential customers. Threw that product out. Started again. Talked to potential customers.Listened. Formed a hypothesis. Gathered feedback. Iterated. Measured. Tested. Deisgn. Built. Lather. Rinse. Repeat.

It is completely different than my experience at Microsoft. And completely worth it.

Don’t get me wrong. It has been difficult. There have been arguments. I’ve been sick as a dog, twice. Payroll is still a bitch. Dealing with government agencies full of red-tape. Trying to write here and at StartupNorth has been difficult.  I’ve been on planes. Trying to build products. Trying to raise my girls. Trying to stay healthy (unsuccessfully – see SxSARS below). I keep helping other startups: here’s looking at you BuzzData, Attachments.me, and TribeHR.

I’ve been heads down for so long that I forget that there are other things going on in Toronto and around the world. I skipped SxSW for the first time in a few years, though I still managed to get the dreaded #SwSARS. It is a very strange experience being sick and not being able to work, even when you want to, versus just taking a sick day when you work for a big company. The fact that I’ve been mostly unavailable because I’ve been stuck in bed and medicated, makes me wonder how long this will continue. I can’t wait to feel human again, and I can’t wait to get back to talking with customers and building. But since the team kicked me out of the office yesterday, I’m home again fighting this zombie virus.

It’s been a fun 185 days. I’m looking forward to the next 185 days and the changes it will bring.


Building communities, not products

Photo by Lawrence Whittemore http://www.flickr.com/photos/lawrence_evil/149197406/in/photostream/
Photo by Lawrence Whittemore http://www.flickr.com/photos/lawrence_evil/149197406/in/photostream/

I’ve been feeling a little rusty this week. I received feedback that my focus of the past 5+ years on community and evangelism was not necessarily a benefit to an early-stage technology company. This came as a shock as I had to justify and rationalize the past 9 years that I’ve lived in Toronto and why I have been relentless about the need to build a stronger ecosystem and community in Toronto.

I moved to Toronto in November 2001. I had left Austin, TX in July 2001 after spending a great few years working at Trilogy Software and at Reactivity Inc. I had spent the previous years doing interaction design, presales, and product management for a sales force automation company and then for early-stage and pre-product clients at Reactivity (this was before the transition from startup accelerator to a product firm aka the XML firewall company that was sold to Cisco). I worked with more than 15 clients including Living.com, AllMyStuff, eLaw.com, Zaplet, MetalSite and others. It was a great time, I learned a lot about small teams, venture funding, and how to effectively build products for undefined markets, undefined customers, and undefined budgets.

When I moved to Toronto there was (and continues to be) a very strong agency culture. There were firms like Cyberplex, BlastRadius, Organic, JWT, ModemMedia, MacLaren McCann, Critical Mass and others. There was a hub for this community with Spadina Bus, TechSpace and AIMS. The problem was there wasn’t a strong Internet application or product culture. I wrote about my investigations looking for TO software companies part 1 & part 2.

As part of the return to Toronto, my spouse started her optometric practice. One of the requirements of the financing to get this off the ground was that I get a regular paying gig. And then strangely September 11, 2001 happened. I took a job working at CIBC in the Retail Markets group as the lead Usability Consultant. I lasted about 6 months at CIBC, big corporate culture was not an environment where I thrived. I found a gig at Ryerson University rolling out the self-service component of their Human Resources Management System. Turns out my first recommendation was to scrap the Oracle 8 Forms based application in favour of new HRMS selection and patching functionality in the existing system using web applications. It looks like the front end of the applicant tracking system I built is still running 5 years after I left (if you’re curious the system built using Fusebox 3.0 running on Coldfusion 6.x against Oracle 9i on Windows Server 2000/2k3). This was as close to product I got until about 2005.

In 2005, I decided I really wanted to be back in the startup game. There was a flurry of activity and events in Silicon Valley, Seattle and Boston that were attracting my attention. I thought I would benefit by replicating the ethos and DNA of these communities in Toronto — see my post on TorCamp. This was the beginning of DemoCamp, StartupNorth and my attempt to facilitate a community of like minded individuals in Toronto doing great things. Did you know that I met Jay Goldman, Jon Lax, Geoff Teehan, Leila Boujnane, Reg Braithwaite, Mike Beltzner, Mark Surman and others at the first BarCamp Toronto?). At the bar after the second day of presentations, hacking and meetups, Albert Lai and I hatched a plan to do a lighter weight monthly gathering modeled after DEMO where entrepreneurs and developers show what they’ve been working on, aka DemoCamp.

And I started thinking about the role that community plays as the framework for making Toronto a stronger ecosystem for software, Internet, mobile startups. I was trying to build my own future. I was trying to create a strong, dense community of companies where designers, developers and entrepreneurs can find employment, inspiration, a sense of belonging. Why? Well this is what I was missing. But it meant that I stepped back from representing a single company or a single product. My role was to build a stronger community. John Oxley and Mark Relph at Microsoft understood this mix of community, product, technology and rabble rousing.  They took a chance and hired me. This allowed me to focus on helping to enable a stronger community. And my particular focus has always been startups, early stage technology companies, etc. It required me to take a role in evangelism marketing. To continue to be a social media enabled and facing presence in the community. To host events and continue to identify, nurture and develop influencers particularly in the unfriendly to Microsoft community.

So it was funny this week to hear from someone in the industry that I respect deeply make comments that my product abilities are substandard and describe the focus of the past 10 years as counter productive to my career. It brought up a lot of personal turmoil about past decisions. And generally it has left me thinking about my role in the community versus my career as product builder. I started all of this community activity because I wanted to build emerging technology products in Toronto. There wasn’t a strong community of product builders and entrepreneurs (or I couldn’t find this community in Toronto). I think there is a much strong network of entrepreneurs, developers, designers, funders and others that have emerged. StartupNorth and TechVibes provide local coverage of events and activities. There are world-class startups like Dayforce, Rypple, Idee, Well.ca, Kontagent, CiRBA and others.

But I think it’s time for me to focus on building a company and products again. To shake off the rust of the past 9 years. And go deep on the product management, design and customer development needed to design, build and ship a world-class product. It leaves me wondering about my pedigree which 9 years ago I thought was stellar: Waterloo, Carnegie Mellon, Trilogy, and Reactivity (an Accel funded startup with spinouts funded by Kleiner Perkins and Sequoia). I get it, this was a lifetime ago. But really have I gone from being an asset to a detriment? And what do I need to do to change this perception. Time to focus on my career and not the community for the time being.

Refreshing my technology

Michael Arrington has a great list of products that he uses everyday. It includes a number of products that I’m hoping to add to my arsenal including:

I’m not sure what’s up, but I’ve been Jonesing for an Android phone. I’m hoping to either snage a Motorola Milestone (think Droid on HSDPA/UTMS) or a Google Phone. I’d like to retire my first generation iPhone, and while the HTC HD2 looks amazing I’m just not excited about it. I want to try to use Goggles and Swype (also available on the WinMo 6.5). The integration with Skynet, sorry Google Mail, is appealing since all of my personal mail has lived exclusively in GMail since 2006.

I’d also really like a Kindle or a Nook, but I’m willing to wait until after CES to see what gets released (Notion Ink, HTC or another manufacturer). It’s also got me thinking about cloud platforms, HTML5 and the browser as OS, improving and dealing with email, improving my calendar, and personal data backup.

I think it’s time to revamp my entire technology stack and usage.