How Jason Calacanis Got His arse Kicked And Then Came Back And Kicked arse


When Eliot Spitzer resigned as governor of New York last year, he invoked a phrase that should be a fundamental guiding principal for every entrepreneur: “As human beings, our greatest glory consists not in never falling, but in rising every time we fall.” 

In the mid-1990s, a young entrepreneur named Jason Calacanis started his first company, Silicon Alley Reporter, by posting xeroxed copies of a newsletter on Manhattan bulletin boards. A few extraordinary years later, Silicon Alley Reporter was one of the leading publications in the industry, and Jason had become the world-famous CEO of a growing media empire.

Then, two years after that, after the dotcom collapse, the only thing left to do was to turn out the lights.

How do you recover from that? 

How do you learn from the experience without obsessing about the past?  What do you take away that will help you avoid blowing it next time?  (And did you blow it?  Or, as an entrepreneur, do you just have to accept that some things are beyond your control?)  How do you pick yourself up and do it again?

How do you get investors to trust you? How do you recruit and motivate employees? How do you rebuild your own confidence?  How do you eat?

In short, how do you do what Jason did, which was pick himself up off the mat, start another company at the depths of the dotcom depression (Weblogs), sell it to AOL, start a third company (Mahalo), co-found a product-launching conference (TechCrunch 50), and, once again, become a fixture in the industry?

In the past 15 years, Jason Calacanis has been through more than many entrepreneurs will in a lifetime. On June 3rd, at Startup 2009, he’s returning to Silicon Alley to tell us about it.

Get your tickets here >

(Photo by Peter Kaminski)


Conference Details











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Startup 2009 will take place in New York on Wednesday, June 3.  The conference is co-hosted by Silicon Alley Insider and New York University’s Stern School of Business, with support from founding sponsor General Catalyst Partners and several other generous sponsors.

Startup 2009 will showcase 10 top startups competing for bragging rights, buzz, and a $50,000 prize.  The companies will make their pitches–and you and our judges will give them the third degree…and then pick the winner.  We’ll also be having in-depth conversations with Jason Calacanis and John Battelle, two entrepreneurs who built great companies, saw them get destroyed in a crash, and then got right back up and did it again. 

Three top VCs will tell us How To Raise A Boatload Of Money In A Crappy Market At A Huge Valuation, and three more will reveal The 10 Biggest Mistakes Promising Companies Make.

The conference will take place on June 3, 2009, at the Schimmel Auditorium at NYU’s Stern School. It will be the first of what we hope will become an annual forum for outstanding entrepreneurs and early-stage companies to meet VCs, investors, journalists, and other members of the East Coast startup community. 

Early-bird tickets are available now (thanks to our ticketing sponsor, Eventbrite) for $395.  We also have a limited number of student tickets for $49.  The Schimmel Auditorium is awesome but small (attendance is limited), so please buy your tickets early.

The Conference

Startup 2009 will be a one-day conference featuring interviews with entrepreneurs, expert panels, networking, and 10 featured startups competing for a $50,000 Grand Prize.

Speakers will include:

  • Jason Calacanis, Founder/CEO Mahalo, founder Weblogs, former EIR at Sequoia.  In his return to Silicon Alley, Jason will describe what it’s like to build a thriving company out of thin air, become a global media star, and then get steamrolled by a collapsing economy.  More importantly, he’ll explain how he managed to get up and do it all over again.
  • John Battelle, Founder/Chairman/CEO, Federated Media; author The Search and Searchblog, former CEO, The Industry Standard.  John also built a huge company (Industry Standard), watched it get destroyed in the dotcom bust, and then bounced back up and did it all over again.
  •   Chris R. Hughes Cofounder,  Chris co-founded and served as spokesperson for the online social directory, Facebook, with Harvard roommates Mark Zuckerberg and Dustin Moskovitz. Hughes currently serves as a consultant for the popular site, but primarily acts as coordinator of online organising within the Barack Obama presidential campaign on, the campaign’s online social networking website.
  • Kevin Ryan, CEO Alleycorp; former CEO Doubleclick; founder Gilt Groupe, Silicon Alley Insider, Shopwiki, Panther, 10gen.  Kevin built DoubleClick from a New York-based startup with a dozen employees to a global behemoth with 1500.  Then he shrunk it to 750 people, sold it, and launched six New York-based, venture-backed startups, including the highly successful Gilt Groupe.  Kevin will explain what he’s learned from this 15-year ride–and why you should never bother with a business plan.

Our VC partners will serve as judges:

  • George Bell, partner General Catalyst Partners; former CEO Excite, [email protected], and Upromise; board member Big Fish Games; Going; HubSpot; PhotoShelter; ShortTail Media and WonderHowTo.  In the late 1990s, George built Excite from a tiny startup to a global behemoth.  He then merged it with @Home and became CEO of the combined company.  
  • Rick Heitzmann, founder/Managing  Director, FirstMark Capital; board member Clickable, Live Gamer, weplay, Riot Games and New York City Economic Development Corporation.
  • Eric Hippeau, managing partner, SoftBank Capital.
  • Jeanne Sullivan, general partner, StarVest Partners.
  • David Pakman, partner, Venrock, former CEO eMusic. 
  • Matt Marshall, Editor-in-Chief of VentureBeat and co-executive producer of DEMO, and Dan Frommer, Senior Editor of Silicon Alley Insider, will also serve as judges.

The Contest

Emerging online companies are invited to submit applications to present at the conference. We will circulate your application to our panel of VCs and experts, who will choose the Top 10 most promising companies from the pool of applicants.  The Top 10 will be announced on Silicon Alley Insider and be invited to present on stage at the conference and compete for a $50,000 Grand Prize.

Applying to the conference is free*, and all companies that apply will be evaluated by General Catalyst, Softbank, StarVest, Venrock, and FirstMark Capital for possible investment. The Top 10 will be featured live at the conference and will be written up on Silicon Alley Insider.

At the end of the conference, one of the Top 10 will also win a $50,000 Grand Prize, which will consist of a $25,000 cash investment from General Catalyst Partners and $25,000 of in-kind services.  The latter will include:

  • Up to 6 months of office space in NYC.
  • Marketing campaign with Silicon Alley Insider.
  • Legal services from a top-notch law firm.

How to Apply – Deadline Is April 20, noon ET.

Emerging companies in the online industry are invited to apply.  (We define “emerging” as up to a few million of seed capital.)  Operating companies are fine. Business-plan-stage companies are also fine, but you will need to describe your planned product and value proposition in detail. 

Here’s how to apply:

1. Log-in to Angelsoft, a web site that connects entrepreneurs and investors, which we have modified for Startup 2009.

2. Click the green “Apply for Funding” button on the right hand side to fill out a Startup 2009 contest application form. (We’ve modified the standard Angelsoft application for use with the conference, so please ignore the “Apply For Funding” part.  You’re applying for the conference, not funding.)

3. Fill in the information and upload your business plan–any other uploaded material will be discarded.

4. Save your work and submit your application.

We will share your application only with our staff and our panel of judges, which includes General Catalyst, Venrock, and Softbank.

Applying to present at the conference is free.*  We’re also offering a promotional package for $295 that includes:

  • Publicity on Silicon Alley Insider (logo, link, and company description)
  • A conference ticket

The $295 can be paid via credit card.

Check out the Rules and Eligibility before you apply.

*We initially planned to charge a $295 application fee, but thanks to the generosity of our sponsors, we’ve been able to eliminate it.  If you’re coming to the conference, the $295 promotional package is still an excellent deal.

Questions? Email us at [email protected].

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