The Calendaring Land Grab

There is a lot of chatter about calendar being the next native iOS application (much like Mailbox and Taskbox for Mail) that is set to be out replaced by a startup.

Atlas Scheduling Re-Invented - Today Feed  - Events & TasksJust looking at my phone you’ll find:

I’m hopeful for Atlas because it has the potential to replace and improve on, ScheduleOnce, Doodle, Skedge and others (see Adam Popescu’s article on Mashable). I’m hopeful that it is as useful a calendar as Sunrise, but the advanced scheduling features are something I still crave post Zaplet (it’s funny, I remember building those screenshots back in late 1999).  The group scheduling application is feature, not a fully functional calendar.

I seem to struggle with  the business model for calendaring applications. I understand why companies like Apple, Facebook, Google and Microsoft need to have applications that are engaging and functional for users on their respective platforms. But it feels like a user acquisition land grab. But one that is focused on engagement and not monetization. I guess a queue of >500,000 users can net you an acquisition around $100MM users.

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?


Reinventing Email

I was just struck by how similar my GMail experience was to the ReMail work that the CUE team at IBM Research published in 2003.

ReMail by Collaborative User Experience (CUE) team in IBM Research

The experiences are different. But the integration of the GCalendar, live names (think GTalk status), thread size and threaded messages, thread visualization (reminds me of Rapportive), collection categorization (a combination of tags and priority). It’s amazing how prescient this work was almost 10 years ago. Amazing.

The best part is being able to track the researchers on LinkedIn:

Marketing Technology Landscape

Marketing Technology Landscape by Scott Brinker @chiefmartec

Scott Brinker provides a must read summary of the 5 meta-trends that underly most modern marketing.

  1. The great digital migration of marketing (and business).
  2. The convergence of paid, earned, and owned media.
  3. Customer experience as the core of marketing.
  4. Rise of the creative/marketing technologist.
  5. Agile marketing management.

The post lays forth a strong foundation for marketers and investors looking at understanding the competitive landscape of different offerings. Interestingly as a practitioner it also provides a great summary of the tools available to enable potential tactics. There are a few logos and companies I think are missing in the landscape, for example, Calls section is missing Twilio and Voxeo/Tropo. And the diagram is missing the entire SMS marketing enablement which are both part of the breakdown of VoIP and SMS through programmatic APIs. I am also trying to figure out where in the list to put InfluitiveCustora, TotangoSpinnakr, Bloom Reach and a few others. It is an amazing list. There are a few new companies that I need to check out and learn more about.

Thanks Scott!

Mesh Marketing

The Mesh Conference team continually amazes me. You can read my bromance piece on the big brother Mesh Conference. But Mark, Rob, Mathew, Stuart, Mike and Sheri continue to do a fantastic job bringing together leading thinkers with the Toronto community. I have hosted my share of local events and I recognize balance of cost and accessibility, but the quality of the mesh speakers and the ticket price is fantastic. I’m always impressed with the spread of speakers from startup to agency to larger company. This event is no different. It has a great group of founders, executives and thought leaders.

The current event is happening in the middle of the fall startup event storm, but it is significantly differentiated from the regular startup event. This is an event for marketers. It is focused on content strategies, mobile tactics, social media tools and features some great folks like:

Jennifer LumHicham RatnaniKristina Halvorson

It’s a great group. I’ve personally seen the amazing work of Jennifer and Hicham (I sit on the advisory board of TribeHR where Jennifer is an investor, and I’m a semi-loyal customer of the Frank and Oak – only semi-loyal because they keep selling out of stuff to fast). It’s a great event and it would be a shame for Toronto marketers to miss the event in their own backyard.

Halifax Pop Explosion

I had a great time at NxNE. It wasn’t representative of the time I’ve spent at SxSW. But this is probably a good thing. I was on a panel hosted by Dave Senior of Playground Inc. with Michael Litt (@michaellitt) of Vidyard and Raja Bhatia (@raja) of Confluence Labs. Great fun talking about startups, traction, funding, teams, marketing, etc. It’s funny, it was a great panel, I spent a lot of time heckling Mike. But I guess the reviews were positive. Because my friend Meghan Warby (@withoutayard) invited to Halifax to attend Halifax Pop Explosion.

I have a few confessions:

  1. I have never been to Halifax.
  2. I am going because I get to see my friends Jevon (@jevon) and Ben (@byosko)
  3. I am putting together new material

I’m in Halifax from Tuesday, Oct 16 until Friday, Oct 19. It’s a short stay, but I am choosing to be home for dinner on Friday with the kidlets. I’m looking for food recommendations, a place to have a pint, and some sights. Any suggestions on where to eat?

I’m also putting together a new presentation. The program description for my talk, titled How to Start a Startup, is:

Everyday more and more web startups are getting founded by entrepreneurs tenured and new. However, most abandon basic business pillars when building a venture in the digital economy. Not every start-up requires the same advice, but there a similar threads that apply to almost every company attempting to build a new digital product. We will be discussing the 5 things every startup must have to succeed.

I need to build a new talk and slide deck. I was thinking I could do something fun, like try to only build a presentation using quotes from The Social Network. Which in looking through the IMDB quotes could be surprisingly difficult.  I need to make this presentation a little more fun. Otherwise it’s going to feel like a “how to” guide for the basics of a startup. Which isn’t a bad plan, but I’m not sure I would sit through an hour long talk. Maybe I can use Paul Graham’s Want to Start a Startup:

  • The Idea
  • People
  • What Customers Want
  • Raising Money
  • Not Spending It

And just intersperse stories I have from Influitive, Maintenance Assistant and the startups I’ve worked with. I think coupled with Thomas Tunguz’s Your startups top 3 priorities

  • Distribution
  • Monetization
  • Engagement
I guess I can talk about my experiences along The Startup Curve. And since I’ve never seen the Acquisition fo Liquidity or Upside  of Buyer, my experience will be limited.
Paul Graham's Startup Curve

Strangely I haven’t given a presentation in what feels like a long time. It’s a good time to build a new deck that is engaging and fun. Maybe I need to start with a simple hypothesis and build out the supporting materials.

Featured Image: AttributionNoncommercialShare Alike Some rights reserved by Steve Dinn

Scotch tape, safety pins and spaghetti – SMB marketing automation

CC-BY-20 Some rights reserved by gotosira
Image courtesy of gotosira Attribution some rights reserved

I was talking to a friend who runs a >10 person distributed professional services firm. He was looking for better tooling to automate his customer processes. He had recently dropped Salesforce, not because it was too much or too expensive, but because the configuration and usage was too complicated for his non-enterprise sales staff. We’ve been talking about his constraints and what he’d like the software to do.

It is part CRM, part project management, part marketing automation. Similar to the “Poor Man’s CRM“.


  • Must access the FreshBooks API – All client billing is done in FreshBooks. It works. His staff is familiar. It is easy enough to send, track and account for with FreshBooks. They are not replacing this.
  • Preferably cloud based.
  • Must work with Microsoft Exchange email.
  • Costs <$150/person/month – this is an all in cost. However a preferred cost is $6000-12,000/year.
  • 20,000 contacts
  • 5,00 active clients
  • Prefer commercial offerings to custom development, and modify workflow to fit new processes.

Work Flow

It’s a pretty standard workflow. From lead capture to opportunity identification. The opportunity is defined by multiple stages, each stage has a series of tasks that usually result in an email being sent or a web form needing to be completed or a signed document. The workflow is pretty linear with clearly defined actions that move a opportunity through each stage of the engagement.

The majority of the business is referrals and business developers sourcing leads (50%). New business from existing clients (30%). And the remaining 20% is from web contact forms.

Possible Solutions

We’ve been talking about both CRM and marketing automation solutions, particularly those that are able to match both an organization or a person to their FreshBooks contact information. The goal is to be able to show outstanding invoices before a new project kicks off.


Web Forms & Electronic Signatures

Email Automation

Scotch Tape, Safety Pins & Spaghetti

I keep leaning towards solutions I have used in the past. But I think they are not the right fit, given that I’m going to have to automate a number of webhooks using Zapier or itDuzzit, which are amazing, but the complexity scares me given the friend. It’s starting to feel like my advice is going to end up with scotch tape and safety pins holding together a spaghetti of web services.

I have no idea if it is the professional services aspect, or the hand off from lead generation to sales to project management. Maybe it is because of the FreshBooks integration (which I have never done). But I’m unclear about what the best options are. I keep finding more interesting solutions. Maybe it is that the past 3 years I’ve been deeply immersed in inbound activities for SaaS offerings that makes me drool over HubSpot and Performable. But I’m just not sure where to go from here.

Thoughts? Guidance on where to look next? I’m stuck.


Not your typical tech startup incubator

This is just too awesome. It looks like the Hyperdrive team staring as a Blue Man like group doing an interpretive dance number. And because when you’re trying to stand out as a startup incubator/accelerator/cyclotron you need to think different in order to change the world.

I guess I know why I’m ordering a red body suit.

Mapping the next three decades of health tech

Envisioning the Future of Health

The good folks at Fast Company sourced an interesting visualization from futurist Michell Zappa and the Envisioning Tech crew. Lots of science fiction, but it provides an interesting analysis based on the breaking down of information silos.

“This visualization is an exercise in speculating about which individual technologies are likely to affect the scenario of health in the coming decades. Arranged in six broad areas, the forecast covers a multitude of research and developments that are likely to disrupt the future of healthcare.”

The article provided interesting links to 2 other visualizations:

The Cocky Rooster

The Cocky Rooster

I had never had a michelada. I didn’t even know they existed until early this morning. I haven’t had a Bloody Caesar in about six years, they are delicious but since I’m now watching my salt intake, I can’t justify 36% in a cup of clamato.

Mott’s Clamato Nutritional Facts

Amount per 8 fl oz. (1 cup)
Calories 50
Total Fat 0g 0%
Sodium 870mg 36%
Carbohydrates 11g 4%
Dietary Fiber 1g 4%
Sugars 9g
Protein 1g
Vitamin A 6%
Vitamin C 4%
Calcium 2%
Iron 2%
* Percent daily values are based on a 2,000 calorie diet.

My friend Zak agreed to be an unlucky participant in my pre-noon beer concoction and curiosity. And it wouldn’t be any michelada, it would be a variant from An Choi Bahn Mi in NYC. Thanks to one tweet from Liv, I decided that today would be my initiation.

I couldn’t find any “33” Export at the LCBO. So I figured that a bottle of my favourite Mill Street Organic Lager.

Cocky Rooster
An Choi, N.Y.C.
Makes one cocktail

1 lime wedge
Kosher salt
1 oz. lime juice
Several generous squeezes of Sriracha
3 dashes Maggi sauce
2 jalapeño slices
1 bottle “33” Export beer

Rub the rim of a pint glass with the lime wedge, then coat the rim in kosher salt. Fill the glass with ice and add lime juice, Sriracha, Maggi, and jalapeño. Add beer and garnish with wedge.

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These are spice, but they are delicious. I’d do it again anytime.