Launching Jason Calacanis

Article appears in SAP Startup Focus Newsletter – Issue 2

Jason Calacanis .jpg

The history, the drama and the mystery behind the Launch Festival event revealed in this short interview. Startup Guru Jason Calacanis tells Ron Wessels, of Startup Focus, about the ever evolving event format and supporting the startup community. Jason discusses his own startup,, enterprise vs consumer startups and more.

Ron: How long have you been helping startups refine their approach and business plans? How did you get started?

Jason: Back in 1996 I hosted my first conference called "Ready, Set, Pitch!" in Silicon Alley. I've been doing the LAUNCH Festival for the last six years.

Ron: Kind of a staggering thought but take a guess, how many startup pitches would you say you have heard since you began? Are there one or two that really stand out and why?

Jason: I've heard thousands of startup pitches over the last eighteen years. Every year five hundred serious applications come in. So, I've seen a LOT of ideas. In terms of what stands out, it's interesting but things like Twitter, Yammer and Dropbox didn't really demo well. They were so simple that you sort of couldn't appreciate them until they hit scale. Of course, somethings like FitBit, Mint and Swype demoed really well.

Ron: TWiST has had a significant impact on the startup landscape worldwide, but now you have started another approach to startups with and the Launch Festival. Do you think there is a gap that you are filling with Launch or is it that the market to startups is big enough to include another pitch driven event series?

Jason: When we started the LAUNCH Festival the DEMO conference was charging $18,500 for startups to get on stage. We flipped that and made it free. Then we flipped it again and put up million in investment prizes. I'm really proud of the fact that when someone tries to get startups to pay to pitch they hear my voice in their heads saying "pay to pitch is a scam! don't do it!" I've had an amazing run as a Founder and I see the LAUNCH Festival and TWIST as my way of giving back. Of course, the truth is they keep me current as well. I don't have to wonder about what's coming, because hundreds of founders a year tell me what their planning to do over the next five years with their startups! I'm in constant learning mode, and TWIST and LAUNCH are my universities.

Ron: Why are you working with startups? Are you just looking for the next big thing to invest in?

Jason: I'm launching my next startup (enter your email for updates) in alpha in Q2 and to the public in Q3. I think it will be the best thing I've ever built and could become one of your three daily habits. In addition to that I invest in three to ten startups a year. I'm also on the board of DYN and just got off the board of GDGT (sold to AOL).

Ron: We see some great numbers being reported, but how has the Launch Festival launch been going for you and team?

Jason: Five thousand folks are coming to the event and over four hundred are registered for the Hackathon. The Hackathon has $75k in investment prizes--which is insane! It's going to be an amazing five days!

Ron: It seems that a large percentage of startups in recent years tend to focus on business to consumer (B2C). If you were to hazard a guess what percentage would you say are B2C and why?

Jason: First, B2C is sexy. Second 100% of founders are consumers, while only 20% of founders might be familiar with enterprise.

Ron: We have noticed a discernible movement of startups to enterprise solutions, particularly big data startups reaching out to the enterprise. Have you noticed a similar shift and if so, what do you think is driving this movement?

Jason: The chances of a consumer product hitting are one in twenty-five. The chances of an enterprise solution hitting are probably one in four. It's also much, much easier to get reoccurring revenue going on enterprise. I mean, if you make a helpdesk product for ten companies that pay you $25k a year each you're in business. We see this over and over again.

Ron: Are enterprise or big data startups in the Launch wheel-house? Why or why not?

Jason: Certainly, and were seeing more and more of them. we are agnostic to consumer or enterprise... we just want the best startups.

Ron: Just because interviewers always try to ask something a bit off the wall…over that last ten years what was your favorite year and month and why?

Jason: Easy: this past year due to my three year old daughter. Best one before that was when she was two, and the one before that when she was one! Professionally, I'd say selling Weblogs Inc to AOL or raising my first VC round from Sequoia Capital.... two items off the bucket list in one year! :-)

The LAUNCH Festival will be held March 4th – 6th, 2013 at the San Francisco Design Center Concourse. For more information, visit

Author and Interviewer:


Ron Wessels,

Senior Director for Startup Focus at SAP

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