Nine Lives

A few decades ago, a career was a lifetime. Working for the same company, rising through the ranks, earning a pension, and retiring was the norm.

And then the Internet happened.

– Digital technology and a connected world changed everything about how we live and work. We’re inside this change, so it’s hard to see the proverbial forest for the trees. But historians will look back on this time as one of the greatest upheaval in human society.
– Technology made everything fractional. We could share a resource, because digital copies are free. But we could also share our car, or our house, or our labor. Gigs are the new normal.
– Technology created myriad niche markets. You couldn’t find a big enough market to launch many worthwhile products when you had to find customers through physical means, but you can find thousands of like-minded buyers digitally.
– Technology let us test things. Crowdfunding, Patreon, Kickstarter, and other platforms allows us to check demand and optimize go-to-market before investing in design and production.
– Technology sped up competition. Stalking your competitors took months; today, you can search for what they’re up to in seconds—and they can do the same to you.

This means the notion of a single career, leading to retirement, is increasingly rare.

Two lethal chasms

If you’re working on a new idea, or getting a startup off the ground, you need to know how to avoid pitfalls and test market strategies quickly. You need to know what kind of team to build, and how to measure your nascent growth.

An early-stage startup founder first finds a problem. She devises a solution. She invents, delivering some kind of prototype or proof-of-concept. But even then, her organization isn’t a startup. What remains is a business model—a sustainable, repeatable way to make money from solving a problem. This is the chasm between idea and acceleration. And it’s a solvable, teachable problem. Helping inventors discover and articulate their business models is the biggest thing we can do to increase the number of viable startups ready to enter accelerator programs or take on seed funding.

By contrast, if you’re emerging from an accelerator with a well-honed pitch and a sense of product-market fit, you need to bring on investment to scale quickly while you’re still competitive. A founder who has found the right product for the market needs to get to scale. He has found and demonstrated a new business model; now he needs to show it can grow to interesting numbers in order to achieve a return on the investment he’s taken in. This is the better-known chasm between startup and mainstream product, first discussed in Geoffrey Moore’s Crossing the Chasm.

Every end teaches and nourishes

Most startups die on one of these chasms. That’s the nature of the beast. But failure done right leads to learning, and those deaths aren’t in vain. With digital technology, deep analytics, iteration, and Lean Startup approaches, startups don’t die in vain, because founders and investors get smarter.

Entrepreneurs can live to fight another day, and sample several careers. They can do this for the rest of their lives, tapping into a global network of customers, sales channels, and talent that’s also available on demand.

There’s another kind of end, of course: An exit. Some startups do hit escape velocity, clearing both the business model chasm and the scale chasm. When a startup succeeds, its founders bring money, networks, and wisdom to their startup ecosystems. Failed startups teach; successful startups nourish.

Our focus this year

Startupfest brings together thousands of people from around the globe, and for nearly a decade our audience has been as diverse and varied as the startup ideas it’s working on. But startup founders—braving the business model chasm and the scale chasm—are our core audience.

Each year, we focus on a particular aspect of the startup world. In year nine, we’re going to dive into the cycle of death and rebirth of startups—what it takes to begin, how to learn, when to kill something, how to achieve escape velocity, and how those who’ve chosen this path handle the inevitable rollercoaster of emotions.

That means increased emphasis on real, personal interactions. We’ve always created an environment where actual networking can happen, and participants from around the world cite Startupfest as the best way to actually connect with the right people. But we can do more; we’re leveraging technology, game models, and new ways to connect people.

It also means expanded training content. We’re bringing some of the world’s smartest, most sought-after instructors and authors to create a curriculum that arms startups with the tools they need to cross chasms and achieve scaleable, repeatable business models.

With Startupfest nine, we want to embrace the nine lives of a startup founder, and explore the ways technology is forever changing how business, culture, and society function as a whole.

It pays to pitch at Startupfest- literally.

Attend this year’s edition of Startupfest (July 12th to 15th) and you’ll walk away with some seriously tangible ways to help boost your business (or business to be) forward.

You’ll soak up some of the first-rate brain power surging from the roster of world class speakers set to hit the stage. Your fingers will get a workout typing up all the new contacts you’ll meet into your phone. But, nothing can get your own startup to the next level like, well, you know, money. And Startupfest is awash in it.

So how do you get your hands on some of the riches? Easy, get your pitch on.

All you need is a honed presentation, a little moxie and a comfortable pair of shoes to get you to all the pitch opportunities at this year’s Startupfest.

So, are you ready to take full advantage of the game changing pitch opportunities (and prize money) up for grabs at this year’s Fest? Good, we thought so. From a group of investing granny gurus to the big payout (that’s an understatement), here’s a pitch primer to get you started:


  1. Best Onstage Pitch

Nothing opens an investor’s cheque book faster than a winning pitch. The Best Onstage Pitch event is where a select group of 7 startups vie for a panel of expert’s attention – and money – on the festival’s biggest platform.

This golden opportunity starts now! Applications to participate in the Best Onstage Pitch are now open! APPLY TODAY.  


  1. Grandmother’s Choice Award

You’ve never seen Nonas like this before. They’ll forever shelve any stereotype you had of seniors being Matlock obsessed, crochet loving folks quietly heading into their golden years.

This group of granny judges are wicked smart, shrewd investors with a BS radar finely honed from decades of seeing it all. Even though it’s a non cash prize, the Grandmother’s Choice Award has quickly become one of Startupfest’s most beloved, and coveted, pitch events.

And when it comes to judging pitches to date, these Grandmother’s have an impressive batting average. In previous editions of Startupfest they’ve picked as winners Onavo (acquired by Facebook for a cool $150 million) and custom-earphone maker Revols (recently raised $2.5 million in Kickstarter preorders).

Think you have what it takes to face this panel of skilled silver haired investors?

They’ll be waiting to hear (and applaud or rip part) any pitch at the grandmothers’ judging tent in Startupfest’s Tent Village July 14th, and 15th from 12-5pm.


  1. The Investment Prize

Imagine what $100,000 could do for your business. Done dreaming? Great, now start thinking about how you can actually bag Startupfest’s biggest payout – The Investment Prize.

Open to any startup in attendance (no need to apply for this prize either), all you have to do is convince the judges (with your killer pitch of course) that you’re worth the money. One startup may walk away with all of it, or two may split it, it’s up to the judges to decide.

Here’s how it works:

  • Track down any of the Investor Judges in the $200k Prize tent in the Tent Village and tell/sell them your pitch. They’ll be there Thursday, July 14th, from Noon-5pm, and wearing a judge badge (hint: you can also see the list of them here).
  • Each judge will shortlist one startup by end of day Thursday.
  • Shortlisted startups will be contacted and invited to a private breakfast Friday morning where they’ll pitch to the entire group of investors.
  • The winner(s) will be selected, and announced at the Friday afternoon ceremonies.


These are just three of the infinite possibilities to pitch your business at Startupfest. Don’t forget that top venture funds and accelerators (500 Startups, Techstars, FounderFuel, to name just a few) want to hear what you’ve got to say in the Tent Village.

So get into a startup state of mind, and sharpen that pitch of yours in time for this year’s Startupfest. Trust us, it pays to do so.

Two More Startupfest Firsts: Play The Future…or be Played By It.




People with long memories may recall that last year, I set a Startupfest first when I created–with enthusiastic attendee help–the event’s improvised national anthem.  (Those with short memories can re-live the event here.)

This year, I’m doubling down on new Startupfest “Firsts,” both about the most fascinating of topics–The Future.

The first “First” involves my own start-up, a predictive gaming platform called Play The Future.  One of my esteemed partners, Phil Donne (former CEO of Campbell’s Soup and Kellogg’s Canada) calls it “A breakthrough brand engagement tool that addresses the splintering of attention, the proliferation of ad-blockers and the wholesale rejection of push marketing”…

…but I call it “a game that lets you beat others, prove you’re brilliant and win stuff.”

That said, PTF lives by two credos:


  • Life’s a game.
  • If it can be measured, it can be played.  


Next week, we are bringing the two together, because for the first time anywhere, people will “play” an event.  Over its three days, Startupfest will turn into an interactive prediction tournament with daily winners, one overall champion, a whole lot of brain-stretching fun and some kick-ass prizes, including an Occulus Rift.

While I can’t reveal actual game questions just yet, suffice to say you’ll be asked to predict things like:

  • How many times Dave McClure will swear
  • How many beers (and/or deals) will be consummated at the opening party

…and so on.

The end result will be a layer of friendly competition, trash talk and surprise learnings draped over the world’s hippest, most relevant gathering of entrepreneurs and smart folk.

Playing Startupfest is easy. The whole thing lives on your smartphone; click here for the app, then Play The Future!

Which brings us to our second future-based “First”…a closing event which–gulp!–questions whether there will even be a future at all.

Okay, maybe it’s not that dire…but almost.  The way Startupfest’s closing speaker Josh Harris sees it, the oncoming “Singularity”–when A.I. basically eliminates the need for humanity–is a bigger threat than global warming, and is way closer than you think.

Crazy?  That’s what they said when Josh predicted the omnipresence of the Internet, reality TV, vlogging, the elimination of privacy and much more.  And when I say “more,” I mean it somewhat disturbingly. To understand, check out “We Live In Public,” Ondi Tomoner’s award-winning doc about Josh here (or see it with both of them Friday night at Startuptfest).

So it is with much anticipation, and way more trepidation, that I’m preparing to interview Josh in a very unique session called “Jack Knowledge.”  

Again, don’t want to give too much away, but to keep with our tomorrow-looking theme, I have these fearless predictions to make about said session:


  • You won’t be bored
  • You may be outraged and/or scared
  • You will change your worldview in 38 minutes



Startupfest 2016 presents The Future.

Play it…while it’s still around 😉