SimsBlog

Soooooo... I Wrote a Book (and why if you've ever had the urge, you should too)

 I wouldn’t say it was a life-long dream, but certainly one that’s been tickling me (yes, tickling, a word I use quite deliberately) for a decade or so.  

I could see stories-to-be-told in everything - in the infuriating mismanagement and decline of the newspaper industry, in the colourful entrepreneurs and venture capitalists of the start-up world, in my own family (perhaps that’s a given) - and I often found myself daydreaming about opening lines, quirky characters and surprise endings.

Still, writing a book seemed like a silly thing to do.  After all, I know actual real writers who have published actual real works of fiction.  A former colleague has even become an international sensation complete with thirteen bestsellers and a movie deal.  Who was I, an untrained wannabe, a business grad for god’s sake, to presume to join their ranks?

But then, during the last few months leading up to the sale of my start-up Shopcaster, as I was entertaining a girlfriend with yet another story of yet another bizarre start-up world encounter (this time with a delightfully idiosyncratic VC), she changed the course of the next year of my life with nine words.  

“God! I hope you’re writing all of this down.”  

And there it was, that old familiar tickle in my stomach.  Only this time, I knew I would do something about it.  

As the story grew more insistent, poking at me at night as I tried to fall asleep, I soon found myself sneaking into the den at four in the morning to make notes.  I didn’t have a choice.  My novel wanted to be written more than I feared writing it.

I learned about eight point story arcs, dove into Chuck Palahniuk’s 36 Essays and later turned to Steven Pressfield to help me overcome “the resistance”, which, by the way, is very, very real.

I’d read that telling people that you’re writing a novel can mess you up (rendering you overly confident or completely demoralized), so I kept my friends and family in the dark.  Only my partner John knew what I was up to.  

Upon completion of my third draft, when I finally started to tell people about the novel, I was pleasantly surprised.  First of all, they took me seriously.  Even the real writers.  

And then, many of them said, “I’ve always felt I had a book in me but…”

“...I’ve never had the time.”

“...I don’t have the discipline to do it.”

“...I don’t want to risk putting that much effort into something and then not get it published.”

And to those people I say: Bullshit.  Do not let fear cause you to miss out on such an extraordinary experience.

Writing a book has been one of the scariest, but also one of the most joyful journeys of my life.  

Sticky notes and index cards were transformed into a plot (with several eight-point story arcs of course).  And after a couple of clunky false starts, I got into the flow.  By the fourth week, I could sit and write for five hours or more without noticing the time go by.  I averaged about 1,000 words a day for four months (my record was 3,272 on March 26th - yes, I tracked).

I had planned my book rather meticulously, with a 40-page outline.  Yet, as new characters emerged, unplanned, but who would later become essential to the book’s resolution, I had the eerie feeling that I wasn’t the one actually writing the story; I was just the scribe.  When I finished the first draft and was forced to put the manuscript down for six weeks (the minimum amount of time recommended by Stephen King - who am I to argue?) I actually missed those characters.  They felt like real people who had left my life.

When I read the work in preparation for my second draft, I was horrified by how bad some of the writing was and amazed by how good some of it was.  As I handed the third draft over to a few close friends, I felt nauseous and didn’t sleep for several days.  And when the feedback was truthful and helpful, I felt grateful for having such wonderful (and willing) people in my life.

Personally, I changed as well.  I now look at people, particularly strangers, differently.  I’m fascinated by them.  I want to know their private hopes and struggles, what motivates them, who they love.  I stare at them a little too long on the subway.  

Having developed a deeper understanding of their literary achievements, I’ve grown a new appreciation for my favourite authors.  Mordecai Richler was always a hero, but now he’s reached deity status (I pray to him when the words don’t come).

Okay, it’s not all rainbows and fluffy bunnies.  While writing the first draft was magical, killing my darlings in the second and third was scary and yeah, the fourth draft (where I am now) is a slog.  

Soon, I’ll start down the path to publication with the full knowledge that the odds that my book will ever been seen by people who don’t actually know and love me are infinitesimally small.  I’ve heard all the tragic stories: the woman who worked on a novel for five years and then couldn’t secure an agent, the guy who got an agent but never sold his book and, worse, the guy who landed a rare and illustrious two book deal only to have the publisher go under a month later.

It doesn’t really matter if I publish or not.   I’m ready to venture back into the real world and a real job.  My year of creative indulgence has had a rejuvenating effect, delivering me from the exhaustion of three grinding years in the start-up world.  I’m looking forward to a new challenge (and a pay cheque).  

But, at the same time, book number two is starting to keep me up at night as new characters and new plot lines begin to form.  It’ll be harder to write while working full time, but I like doing difficult things.  I get bored otherwise.

So it turns out, among many things, I’m also a writer.  Perhaps you are too.

My Start-up was Acquired. Now What?

It wasn’t the kind of deal where everyone gets rich.  But, Shopcaster lives on, providing an amazing service to indy-retailers and consumers alike.  So, I’m okay with it.  Really, I am.

The day the last of the papers were signed, my partner and I jetted off for two weeks in Cambodia.  We rode in a tuk-tuk or two, flew in a helicopter over Angkor Wat, watched monks frolicking in a sacred waterfall and spent a few days on a private island in the Gulf of Thailand.  

It was awesome.

But now I’m home, and after an initial rush of “I’m freeeeeeeee!”, I admit to finding myself rather lost.  

Being CEO of a start-up was all encompassing, occupying 90% of my thoughts for close to two years.  It’s unnerving to have it all just stop.  I miss building something.  I miss being in New York all the time.  I even miss the painful day-to-day struggle that began to hurt so good.  I still compulsively check my email every 15 minutes, but no one has anything to tell me.  Nor do they need me to tell them anything.  I found myself writing to the new owners alerting them to some tasks they need to complete before the end of the year.  They wrote back, kindly advising me that they’re already on it.  

I don’t know how to not worry about Shopcaster.

This is not a place I expected to find myself at 42 years old.  I’ve always been driven, always planning two or three steps ahead knowing exactly what was next.

Not this time.  This time, I’ve decided to take my time.  I want to learn to code (hello Codeacademy!) and to speak Spanish.  I could stand to lose 20 pounds or so (hello gym!).  I want to go vegan (hello seitan!).  I want to write more.  Oh, and meditation!  Gotta do more of that.

I’ve never followed a traditional path.  At 16, when my parents moved to a new city, I decided to stay put, got a place with two older siblings and paid the rent with a part-time retail job.  Eventually, I dropped out of high school because it interfered with my job and frankly, it was boring. I earned my diploma by correspondence which was much more my speed (three years of French in three months - woo hoo!).  Got married at 19, divorced at 26. 

At university, I ran the student consulting program for three years.  In the corporate world, I gravitated to new ventures and product development.  I launched a national celebrity magazine and four websites and was the youngest woman to become a VP at Canada’s largest newspaper.  I’ve run two start-ups.  I’ve had spectacular failures and great successes.  

But for some reason, being okay with not knowing what’s next feels like the most audacious thing I’ve ever done.

The true gift of running Shopcaster was discovering a depth of courage I never knew I had.  It’s time to put it to the test.  This time, for me.

Wish me luck.

5 Tips for Corporate Types Looking to Break into the Start-up World

A few yeas ago, Jeff Jarvis was in Toronto promoting his book What Would Google Do.  As a VP Digital at a large newspaper, I invited him to stop by our offices to meet some key executives and to provide some input into a planned redesign of our website.

It was a nice afternoon, if a bit weird for Jeff (he was placed at the head of a giant boardroom table and asked to give his perspective on the future of media).  But at the end of our time together, I did something strangely out of character.  I pulled Jeff into my office and begged him to help me get the hell out of the newspaper industry.  

I had been a vice president for less than 6 months and though I loved the world of digital media, I was quickly discovering that I did not love the corporate world.  I wasn’t good at the politics and couldn’t get my head around working in an industry that seemed more interested in managing decline than building something new and exciting.  In fact, I was having daily dirty thoughts of working in the start-up world.

Amazingly, Jeff (who is very kind) did in fact help kick-start my journey toward a new life in the start-up world simply by making a few introductions.  

I took it from there.  And, after a little soul searching, a lot of work and a couple false starts, I’m now the CEO of Shopcaster, an ecommerce start-up that I’m currently expanding into the US.

If you feel trapped in a corporate job and long to make a break, here are five tips for making the big leap:

1.  Make sure you’re doing it for the right reasons

Do you have a genuine desire to build something from nothing or are you just bored or dissatisfied with your current job?  Or worse, have you watched The Social Network too many times and are dreaming about Zuckerberg’s billions?

Start-ups are hard.

Can you handle constant uncertainty?  How about ambiguity?  Constantly changing priorities?  Are you willing to work long hours at a punishingly fast pace?  Are you capable of working with next to no resources - ie. in a tiny office space with limited staff and virtually no marketing budget?

Without true passion and drive, you’re going to struggle.  

2.  Make sure you can afford it

With all the stresses of start-up life, the last thing you need is to be worrying about your own finances.  If you get paid at all, start-up pay is nowhere near the levels of corporate pay (not to mention the lack of benefits).  

Sure, the long-term goal may be to make your millions, but the truth is, most start-ups fail.  Do yourself a favour and build nest a egg first.  Even if it takes a couple of years to get there, at least you’ll be working toward something.  And, you won’t be freaked-out about your mortgage payment when you should be focused on how to grow your business.

3.  Talk to everyone

Do your research.  Which start-ups do you admire?  Who are their investors?  Get some meetings and let it be known that you have a certain skillset and you’re looking to make a move to a start-up.  

If you’re not a techie and you’re looking for a technical co-founder, get ready for a long hard search.  It’s probably easier to find a husband than to find a great CTO.

Ask for help.  In the corporate world, we’re taught that needing help is a weakness.  In the start-up world, not admitting that you need help is a weakness.  Ask for introductions, ask for advice, ask for resources.  

But, you have to be willing to give help too.  Which leads us to tip #4...    

4.  Be willing to work for free

If you’re looking to join an existing start-up, the best way to break in is to volunteer your time and do some project work.  You can do it by working nights and weekends before you leave the corporate world.  Not only will it show the start-up team what you can do for them, but it will help you determine if start-up life is really for you (see tip #1).

If you’re starting a new business from scratch, you’re going to need a working prototype and some thoughts on a revenue model before your first investment.  That means working for free.

5.  Only make the leap if you love, love, love the start-up you’re entering

My first start-up job was at a company called CanSport LIVE where we were gathering amateur sports organizations into a digital advertising network.    I joined the company because I thought that the business model was very clever (we were selling actual soccer moms to advertisers).  

But the job didn’t give me the satisfaction I longed for when daydreaming at my old corporate job.  And that’s because I have zero passion for amateur sports.

So I had to go back to the drawing board and that’s when I found Shopcaster, a company I truly love with a mission I care deeply about.  

And let me tell you, I took a 70% pay cut for this job and I’ve never worked harder in my life, but I’ve also never been happier or more fulfilled in my career.  

I wish all you daydreaming corporate types the same.

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I Have a Confession to Make: I'm No Longer a Newspaper Person

A couple weeks ago, I tweeted about newspapers with Twitter giants Jay Rosen and Mathew Ingram.  This may not sound particularly surprising or unusual, but the truth is, I haven’t tweeted about newspapers in months.  And, it felt a little strange.  

Perhaps even more telling, I haven’t written a blog post in almost a year.  Take a look, my last post was about what newspaper companies should be focusing on in 2012.

You see, I have a confession to make.  I’m no longer a newspaper person.

My journey to non-newspaperdom has been such a slow process, I hardly know when it began.  But I think I can pinpoint it to the Spring of 2006 when I took a five day course on innovation at the Harvard Business School.  

I was the Director of New Ventures for my newspaper company and at the time was struggling to save a failing print magazine that I had created a few months earlier.  The highlight of the week was a session with Clay Christensen in which he discussed his theories on disruption and innovation.  During the case discussion, Christensen challenged me to think about how newspapers and other print media could innovate in the digital world to save themselves.  I admit that I dismissed the idea immediately thinking, “It’s not that easy for our industry...he doesn’t understand...dollars for dimes" and all that stuff.  When I pushed back at him (embarrassingly cocky of me), he just shrugged and said, “Newspapers will have to innovate, or they will fail”.  

Those words stuck with me.

Over the next three years (after shutting down my magazine), I spent all of my time learning the digital space, eventually becoming Vice President of Digital Media.  I came to understand the new economic reality of the media industry and the new drivers of value and competitive advantage.

I discovered that it was possible for newspapers to innovate their way back to prosperity if only newspaper executives would:
a) take innovation seriously and
b) get out of the way of the people trying to innovate

Newspaper executives did neither of these things.  

And eventually, like thousands of other newspaper employees, I was “structured out” of the industry.  In my case, job loss turned out to be a very good thing.  It allowed me to redefine myself through my blog, my Twitter presence and various consulting and board gigs.  But I still felt very much a newspaper person.

Now, as I watch an industry-wide proliferation of cost cutting, paywalls and cash cow milking, I’m just sad.  These great institutions are eating themselves alive due to a lack of imagination, a lack of will and a lack of courage (with a couple notable exceptions).  

I've become disconnected.  I won't return to the newspaper industry.  

In fact, I’m off innovating in the world of local, independent retail as CEO of a start-up called Shopcaster.  I work in a world where disruption and change are expected daily, things move super fast and inertia leads to a certain and speedy death.  I love every second of it.  I know I'm where I'm supposed to be.

I will always love the newspaper world and newspaper people (hell, I live with one) and I wish them well.  Perhaps there’s still time to save themselves.  Clay Christensen has teamed with Neiman Labs to offer more advice to newspapers.  And there’s some pure-play digital good'uns returning to newspapers to fight the good fight such as Jim Brady and Steve Buttry at Digital First, Mark Potts at the Journal-World and John Ferri (full disclosure - the aforementioned person I live with) returning to the Toronto Star.

But, I’m already well into my next chapter.  Watch for this blog to be about the joy and pain of growing a tech start-up.

The chart below is already proving to be more accurate than I would like to admit.  

I hope you’ll stick around for the ride.

 

Start-Up Visit: Claystone Inc.

Recently, I had the pleasure of visiting the offices of a Canadian rarity – a digital start-up aimed at the consumer market, rather than the B2B market.

Claystone Inc. is a dynamic home screen launcher and media player application for Android that replaces an Android device’s entire interface. 

What’s cool about Claystone is that it gives users the ability to create “content stacks” where you can queue up content such as news feeds, social media feeds, videos, photos, games, etc for a fast and seamless viewing experience.

CEO Christian Lassonde says that Claystone helps you get more done on the home screen and spend less time switching between apps. 

I’ll say. 

The first thing you notice is how lightening fast it is.  I could barely keep up during a demo as Lassonde zipped from news story to video to Twitter feed all on the home screen, all without opening a single app. 

You can even organize your stacks into categories of your choosing.  For example, you could have a stack for business news, one for sports, one for TV shows, another for games even contacts can be stacked up on your home screen for easy access.  The content in the stacks can be saved for later viewing, even offline.

Very cool.

Android’s multi-tasking ability is one of the big feature wins over iOS.  It’s easy to see that as our digital lives become increasingly mobile, a fast, flexible time saving interface will become important. 

Though Android does offer more flexibility, it's a double edged sword as the phones can seem overly complex, particularly to newcomers.  This could be reflected in Claystone’s 3.7 out of 5 rating in the Android market and is why Claystone’s mantra has become simplify, simplify, simplify.  One innovative way that they are achieving this is by adding game-like elements to the user experience.  New functionality will be enabled only as users master the initial features.

At 37, Lassonde is already a veteran entrepreneur.  A Toronto native, he spent 10 years in San Francisco where following a stint at Second Life, he launched digital ad agency Millions of Us and continues to serve as a co-founder and board member at virtual eCommerce business Virtual Greats.

After returning to Toronto in April 2010 (so that he and his wife could raise their two children closer to family), it didn’t take Lassonde long to meet up with two of Claystone’s founders Dale Darling and Prasad Maruvada.  After some initial consulting work, they soon asked him to become the company’s CEO.

The business model remains somewhat vague.  The app itself is free, so the Claystone team needs to be creative in determining alternate revenue sources.   What has been clearly established is that users do not want to see ads on the home screen of their phone.  It’s more likely that revenue will come from paid content in the form of affiliate deals with video and other content providers.  In the meantime, Claystone design themes are available for purchase in the Android app store.

Perhaps the most surprising thing about Claystone is its very international user base.  A full 25% of users are Chinese, 25% are American and the app is also popular in India, Italy, Germany, France, the UK and many other countries. 

Claystone is proving that Canadians can produce great B2C digital products.  So why is there still a relative dearth of Canadian B2C start-ups?

It all comes down to funding.  To get a good feel for the state of the Canadian VC scene, one only needs visit the website of the Canadian Venture Capital and Private Equity Association.  So boring…so unhelpful…snore.

The truth is Canadian VC’s tend to be conservative and are fond of smaller bets (in the $100K to $500K range) in support of early stage start-ups, and lots of them.  And it seems this trend is picking up steam: 134 Canadian companies were financed in Q2 of this year, an increase of 11% over the same period last year, but the total value of those investments dropped from $355 million to $328 million.

This focus on early-stage ventures while avoiding larger investments aimed at making big, global scale plays aimed at the consumer market could hurt Canada’s tech scene in the long run.  As Mark Evans recently blogged on StartUpNorth, it doesn’t lead to the creation of a vibrant tech culture with hundreds of new tech-related jobs.  Instead, most often, Canadian start-ups are purchased by US companies and the business and its founders move south, further draining the small entrepreneur culture we do have.

I think it’s worth keeping an eye on Claystone.  I hope they’re a big Canadian success story.