Chief Shit Disturber

My friend Howard Gwin (LinkedIn) has said the perfect role for me would be one of “Chief Shit Disturber”.

“an individual who creates unnecessary conflict and unhappiness where it is especially not required” – Urban Dictionary

I’m not sure that this is quite what Howard intended. But that I live in the creative tension between product, marketing, development, customers and growth. It’s a chaotic place where the demands change instantaneously and often change due to forces unrelated to the company or the team. (Or at least that is what I hope Howard means, and not that he thinks I stir up trouble unnecessarily.)

I have often thought that the perfect role for me would be one like James Higa, who Steve Jobs picked as “his right hand man”.

“One was an ability to be frank, honest, and able to go toe-to-toe with him on any question. The other was wide peripheral vision. He’s always wanted that in the people around him. The ability to connect dots is really important. A Renaissance perspective on the world. Because it was always about the intersection of technology and liberal arts. BusinessInsider

Not to say, I won’t do the founder thing again. Founding Influitive was exciting/fun/stressful. Leaving wasn’t easy, but it was the right thing to do for me, for my cofounder and for the company. It gave Mark the room he needed to operate more effectively. I have enjoyed going toe-to-toe with Mark on everything from product design, to customer acquisition, to fundraising, to hiring, to company culture. I think Mark appreciated the candor and insight, as he has a Chief of Staff role that sounds strangely familiar to me.

But it has me on a new career path. I am back in a world as a consultant. I’m not sure that this consulting thing is going to be a permanent thing (see Teehan+Lax: A Happy Accident), but I will try it, at least part-time. I am spending part of time at OMERS Ventures, where I get to see how the sausage is made. But I’m trying to figure out what to do with the rest of my time.

I have worked with startups for a very long time. Some have been successful. Some haven’t. But I know I add value. The challenge with early-stage companies (pre-Series A) is that they can’t afford to pay me (for more reasons why this is important). I am looking for models that work and don’t work for a consulting practice. Yes, yes beware the consultant. And consulting math versus software math. And you can read my thoughts on being/using a funding broker, ain’t happening.

It would be easy to pay for bits or bit development. But we’re talking advice. Kind of like a lawyer. I can’t figure out how to make this work. Any thoughts?


Maker’s mode

CC-BY-NC-ND-20  Some rights reserved by drp
AttributionNoncommercialNo Derivative Works Some rights reserved by drp

It has been a long time since I built anything. I was trying to think through my last set of projects where I did the “making”.

  • Influitive – I started Influitive with Mark Organ (@markorgan) in the fall of 2010. We built the first set of mockups, screen flows, wireframes and prototypes with a very small team. It was a ton of fun, it wasn’t easy, but it was fun.
  • Spadina Optometry – I have the unfortunate task of being the cobbler. It’s nothing fancy, Wordrpress on Dreamhost but it’s HTML5, CSS and some PHP to keep me engaged.
  • StartupNorth/DemoCamp/Founders & Funders – StartupNorth is a blog, written, primarily, 3 guys about Canadian startups and the issues that affect high tech, high potential growth software/SaaS/mobile/etc. companies in Canada. This was about building connections and helping to facilitate a community in Toronto (and across Canada). But StartupEmpire was in 2008, the last DemoCamp was back in 2011. But no one expects that StartupNorth is set to be a game changing media play, it’s a regional blog about high tech entrepreneurship and emerging business models and technology.

I look at my friends that are all very successful in different ways:

They are all making stuff. Whether it is communities, sensor networks, conferences, software companies, it seems to be about making. And they are not alone:

What is making?

Authors produce books. Musicians produce albums (and tours). Vinters produce wine. Master distillers produce whisky. Developers produce software. Entrepreneurs produce companies. I think I need to get my head around making.

“MAKE unites, inspires, informs, and entertains a growing community of resourceful people who undertake amazing projects in their backyards, basements, and garages. MAKE celebrates your right to tweak, hack, and bend any technology to your will. The MAKE audience continues to be a growing culture and community that believes in bettering ourselves, our environment, our educational system—our entire world. This is much more than an audience, it’s a worldwide movement that Make is leading—we call it the Maker Movement.” From Make Magazine

When  I look back on the projects, activities, and companies I had the most fun being a part of in the past 15 years since grad school, they all involved making. Undertaking projects in “backyards, basements and garages”. Some were successful, others were less successful but just as much, maybe more fun.

I’m starting to think rather than looking for a job, I need to start to look for what I’m going to make.

Time to undertake a new project.

Under-related Resources


The day the punk music died

Joe Strummer by Simon White at Toronto Calling
Photo by Simon White in Toronto Calling exhibit

It’s been 9 years since Joe Strummer passed away from an undiagnosed congenial heart defect. Joe Strummer and The Clash were my biggest musical influence. I eagerly awaited the release of The Future is Unwritten (and I’m now the proud owner of a Region 2 DVD from My friends Scott Berkun, Roger Chabra, Saul Colt and others have reminded me about how important Joe was both musically and politically.

Joe Strummer by Simon White - Toronto Calling
Photo in my living room thanks to Lee Dale, Kristin Heeney and Simon White for the best friends and a special gift

“And so now I’d like to say – people can change anything they want to. And that means everything in the world. People are running about following their little tracks – I am one of them. But we’ve all got to stop just following our own little mouse trail. People can do anything – this is something that I’m beginning to learn. People are out there doing bad things to each other. That’s because they’ve been dehumanised. It’s time to take the humanity back into the center of the ring and follow that for a time. Greed, it ain’t going anywhere. They should have that in a big billboard across Times Square. Without people you’re nothing. That’s my spiel.” — Joe Strummer

It was Billy Bragg’s post this morning that connected connected Joe’s view on worker and humanitarian rights explicitly for me to the Occupy movements.

Thanks Joe!

The problem with Microsoft…

Some rights reserved by Nick, Programmerman
Attribution Some rights reserved by Nick, Programmerman

Gary Rivlin at Fortune Magazine has some recent articles about Steve Ballmer and Microsoft senior management (The problem with Microsoft… & Why insiders think top management has lost its way). The articles make great fodder given the rise of Apple to be larger than Microsoft in both market capitalization and revenues. What is strange is that I love both of these companies. I’m an ex-Microsoft employee. It was a great place to work. And I have been an Apple fanboy for a long time  (spending my entire signing bonus in 1997 on Apple stock). Let’s be clear Microsoft is still a large powerful company, they have just lost their way in defining the next generation of technology, business models, and customers.

Still, Ballmer needs to do something to shake Microsoft from what, at best, seems to be a textbook case of corporate ennui: MIT’s Michael Cusumano, who has featured Microsoft in several books, including the new work Staying Power, sees a company hopelessly stuck in neutral, in no small part because Microsoft has a weak board and no one expects Bill Gates, the company’s top shareholder, with about 5% of shares outstanding, to oust the CEO, who was the best man at his wedding. “Ballmer has been a good steward of Windows, and that’s about it,” Cusumano says.

Gary Rivlin nailed my feelings and analysis on Microsoft in The problem with Microsoft…. Microsoft is a juggernaut. But the markets and choices are evolving. There are a few successes like Silverlight, Kinect, XNA and Office. But generally the article highlights deeper structural and cultural issues.

  • Windows Platform dominance – Licking the cookie
  • Politicized management culture with “Made men” and “political assassins”
  • Lack of urgency – Massive existing businesses SharePoint is the last $1B revenue business
  • Killing products too early or too late – see Courier (too early) and Kin (too late it should never have made it to market)
  • Stock stagnation – this has a lot of impact on hiring new talent, retaining talent that should retire (under water ESOP buys)

There is lots to love about Microsoft. But I think there are even more concerns for the future. Just look at what the latest generation of big web companies are building on: Yahoo! (PHP, MySQL, Hadoop), Google (Java, Python, BigTable), Facebook (PHP, memcache, Cassandra, Linux), LinkedIn (Solaris, Tomcat, Oracle), Groupon (Java, Salesforce, EC2, Zynga (PHP, MySql, AMF), Quora (MySQL. memcache, PHP). Sure there are shining examples of companies building on SharePoint and SQL Server and Azure, but do they have the size and scale of those previously mentioned? And look at the fight for mobile developers. Appcelerator’s quarterly developer survey shows percentage of developers “very interested” in developing for different platforms: iOS (91%); Android (85%); Windows Phone (29%); sure it’s a head of Blackberry (27%). But this just reinforces my concerns and disappointment. Microsoft is a huge company. And I hope they can continue to build world class products, markets and inspire future developers.

SMS and Canadian Phone Numbers

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Photo by UggBoy♥UggGirl

I’m a huge fan of Google Voice. I’m not alone the team at TechCrunch also seem to be fans. I would really like to use my 416 number with a provider like Google Voice that let’s me keep this as my primary number but forward calls and SMS messages to a device or application I am using. Basically, I’d like to have my 416 follow me to a T-Mobile number of my choice in the US or a Wind Mobile number or a where ever. Basically I’d like something like Google Voice with a Canadian number.


I have a Rogers Wireless phone that until very recently has been my primary phone, but with the introduction of the Wind Mobile’s outrageous holiday rate of $40/month I decided to get a new phone. However, because I do travel out of the Wind coverage zone I kept my Rogers phone (it has a 1Gb North American data plan that I use when in the US and rural Ontario). I think MG Siegler has captured by desire to take control of my phone number (which is increasingly my SMS contact point). I’d like to port my 416 number and have access using the devices that are important to me: Android, iOS, SIP phone, softphone, and SMS.

As part of this I started looking at business solutions for the Influitive offices. Theand I’d really like to set up a Canadian business solution. But it seems that the SMS piece particularly for inbound Canadian numbers seems to be the bottleneck. This makes me suspect that the issue is either with the CRTC and a whole bunch of stuff that I just don’t understand (or care to understand) or with CLECs and SS7 hardware and a bunch of other stuff I just don’t understand. Anyone know why I can’t get SMS messages on VoIP providers for Canadian numbers?

I’m trying to find an alternative to Google Voice and a Canadian number. I’m thinking that I will try OpenVoice and Anveo as a SIP provider. I’m hoping this should work.

Provider Cdn Number Port a Cdn Number Inbound SMS to Cdn Number iOS Android Blackberry SIP access Comments
Google Voice Icon by Icon by Icon by Limited support of Canadian area codes (403 in Alberta)
Toktumi & Line2 Icon by Icon by Icon by Icon by Icon by No inbound SMS for Canadian #s, No SIP phones Icon by Icon by Icon by Icon by
VoxOx Icon by Icon by Icon by No SIP phones Icon by Icon by Icon by Icon by Icon by Icon by No inbound SMS for Canadian #s Icon by Icon by Icon by Icon by Icon by No inbound SMS for Canadian #s
Skype for Business Icon by Icon by Icon by
OpenVoiceTropo Icon by Icon by Icon by
OpenVBXTwilio Icon by
Cloudvox Icon by Icon by
Teleku & OpenVBX Icon by Supports Teleku and Google Voice SMS forwarding with Gizmo5
Asterisk & SIP phone

Icon by Icon by Icon by Great services. Managing a asterisk install was too much for me. rumored to have SMS inbound in Feb 2011.
Anveo Icon by Icon by Icon by Icon by

What are other startups using for their office phone system? I’m leaning towards I know a few others that are using OneConnect, but it bugs me they don’t list their prices.

But hoping others have thoughts? Opinions?

Building communities, not products

Photo by Lawrence Whittemore
Photo by Lawrence Whittemore

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, AllMyStuff,, 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,, 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.

Goodbye Microsoft, so long and thanks for all the bits

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Photo by Stuck in Customs

Can you believe that it has been 1230 days since I announced I was joining Microsoft? I’m guessing a lot of people lost out on that one in the over/under pool. Well, it has been a fantastic 3 years, 4 months and 7 days so far, unfortunately there are only 4 days left until it’s over for me. Effective Friday, September 24, 2010 I will be leaving Microsoft Canada.

I’m heading back into the fray. Or as John so eloquently puts it, I will be starting on a new path, with some old friends and the plan is actually quite simple:
Have fun and try to take over the world responsibly. I’ve spent the past 3+ years talking to entrepreneurs about programs like BizSpark and trying to help them build on the emerging Microsoft technologies and platform. I’m looking forward to getting back in the trenches and using customer development to build and ship products.

I’m not alone. There are a few of the folks that I’ve worked with or been lucky enough to call a friend that have also left Microsoft in the past year including: Don Dodge, Adam Kinney, Scott Barnes and others. This didn’t impact my decision to leave, it’s more just a curious observation.

As a sidenote, I’m pretty sure that John will be looking for a ISV DE (in non-Microsoft acronym speak: a developer evangelist focused on independent software vendors). What does an ISV DE do? Here’s the ISV DE job description from Belgium.

The ISV Developer Evangelist mission is to drive platform adoption and revenue growth with depth and breadth ISVs. The ISV Developer Evangelist is focused on winning ISV adoption of Microsoft platform technologies by working with ISV senior technology decision makers within these organizations. This is accomplished by collaborating with the ISV PAM (Partner Account Manager) to build a well-managed, mutually beneficial alliance that drives revenue growth and expands the reach of strategic Microsoft products within the partner’s solution portfolio.

It was a great time to be a part of the Developer & Platform Evangelism team at Microsoft Canada. And if I’d consider working with John Oxley (@joxley), Mark Relph (@mrelph) and the team again in the future. If you’re looking for a fun gig working with ISVs including startups and emerging companies, make sure you follow up with John.

204 Beech

I hate to see the struggles of my friend Geoff and his family.

The article at Open File identifies the closed black box nature that makes this so difficult. If this were a functioning court of law, the Teehans would at least have the opportunity to confront their accusers and see the evidence submitted. However, this backroom politicking leaves the taste of a councillor abusing her power. Ms. Bussin should be removed from office and a formal inquiry called into her behaviour.

Bussin says she has received “a number of emails and calls concerned about the future of that particular house,” as well as an online petition. She said she couldn’t give exact numbers of how many people were concerned.

These concerns led her to get an independent opinion of the property. She consulted ERA Architects, Inc., a firm the city regularly works with for heritage conservation issues.

In the undated document ERA Architects prepared for Bussin, Michael McClelland, a principal with the firm, “confirms” that the 204 Beech Ave. property has heritage value. He cites that it is a “Beach Cottage” type home with “typical elements found in buildings representative of the Cottage style.” He adds that a “recessed fully glazed entry porch, the rendered finish, and irregular pattern of fenestration are important elements of the dwellings character.”

This is a terrible, selfish abuse of power by Sandra Bussin. Jim Graham gets it right, it is not the role of the city or the neighbours to determine what the Teehan’s can do with their home. If Ms. Campbell wants to be upset with individuals for not making this property a heritage property, it’s her own parents who had the chance before they sold the home.  This is a fight for property rights. And we need to make sure as home owners that we do not live in fear of rogue politicians or expatriates or anyone else.

“The more this situation unfolds the clearer it becomes this isn’t about modern vs traditional, new vs old or even about the accessibility requirements. This is about property rights. We did our due diligence, we bought the property and are submitting plans without easements or variances. Now a neighbour who doesn’t want her view changed and a women who lived in the house decades ago and resides in Germany have more control over our property than we do. This isn’t something that residents of our neighbourhood should be worried about, this is something Toronto and many parts of Canada should be worried about.” – comment by Geoff Teehan on Open File

What a disgraceful display and an abuse of power by a Toronto councillor! Ms. Bussin you should be ashamed.

Four years later

photo by mariobraune
Photo by mariobraune

Time flies. It was four years ago that I had a myocardial infarction at DemoCampToronto6. That’s right, you read that correctly, I had a heart attack at DemoCampToronto6. I’ve had the misfortune of returning to the cardiac care ward just before StartupEmpire in 2008 after PDC for a second angiogram. The good news is the second time, everything was fine.

t has been a great 4 years in Toronto. Together with a loose group of friends and co-conspirators we’ve build a vibrant ecosystem for startups, entrepreneurs, designers, technologists and others. I hope that I’m around to see my daughters grow up and this community flourish. I’m grateful that we live in a city, province and country with fantastic medical care. Thanks to LeilaJay,Sutha, and everyone else for recognizing the symptoms and getting me to Toronto General (thanks to MaRS for being so close to TGH). Thanks to Dr. Eric Horlick and the entire staff at TGH for a 4am CathLab run.

Thanks to everyone for making the past 4 years so memorable.

I’m not alone, Om Malik suffered a heart attack in 2007. Paige Freeborn suffered one also in 2008. Heart disease is the leading cause of death in Canada. I hope that all of my friends and acquaintances through StartupNorth, DemoCamp and other activities will take the time to visit their doctors and ask about their risk factors for heart disease.