Jason Calacanis is the CEO of Mahalo.com, “a human powered search engine,” as well as the former co-founder of Weblogs, Inc. and GM of Netscape. His latest mission (quest?) is to ensure that entrepreneurs are never forced to pay to pitch to angel investment firms.
Jason was kind enough to provide his take via e-mail on a wide range of topics, including his involvement with Open Angel Forum, the latest doings at Mahalo and in the blogosphere, and the future of the New York Knicks.
What is Open Angel Forum, and what’s your involvement with it?
Open Angel Forum is a movement to create a *free* forum for angel investors and startup companies. It is a for profit effort that will not profit from charging startups access to angel investors.
The format will be like any other angel forum: a handful of startups will pitch a room filled with angel investors. If there is a match the investors will follow-up with the startups and make an investment. We’re going to start in Los Angeles, where I know two dozen high-profile angel investors, then we will move on from there.
You’ve always been something of an iconoclast. Do you see your current campaign to end the practice of angel investors charging entrepreneurs to hear pitches as part of some larger “quest”?
When I was coming up as an entrepreneur I had to fight for everything I got and there was no clear roadmap of how to be successful. I’ve been more successful than I probably deserve, so I’ve been spending 10% of my time trying to give back to “the game.” That’s why I started the TechCrunch50 conference with Mike [Arrington], that’s why I angel invest and it’s why I started This Week in Startups. I like to share what I, and others, have learned. I think entrepreneurship is a beautiful thing.
Is the practice of charging entrepreneurs to pitch similar to agents charging aspiring writers/actors to review their work/resume?
Exactly!
They are just as predatory and slimy as “model agents” who charge aspiring models for head-shots and modeling lessons. It’s repulsive, and no real angel investor charges.
What stage should startups be in when they approach OAF and what range of funding will be invested to successful entrepreneurs?
We’re going to target the OAF at pre-Series A obviously, but it will be open to entrepreneurs with or without a track record.
What kinds of startups will OAF be looking for?
Ones that want to change the world in the technology space I suppose, but we’ll see where we take it. If folks want to pitch restaurants and sports drinks, well, I guess we would consider it!
Can you describe the first time you pitched angel or VC investors – what was it like?
I think one of the first times I pitched someone it was Jerry Colonna of Flatiron Partners. He took the time to explain to me how venture capital worked and what pitching was, and that’s why he was a great VC.
Your lengthy essays that you send to your e-mail group (and repost at times to your blog) are always interesting, opinionated, and fun. Any additional plans for these?
Yes, I’ve got about five that are between 60-95% done. I just like to sit with them for a while. I’ve got one on “creating a corporate culture document” and another on building community that I’m almost ready to hit the send key on.
You famously “retired” from blogging some time back, but now use your blog presence as something closer to a microblog (posting pictures, content snippets, links, and video, etc.). What are your thoughts on this, and what’s your take on the state of the blogosphere?
Blogging is great and I read blogs all day long. However, my goal is really to have a deep meaningful discussion with people. For some reason I’m able to accomplish this best via email. I’ve gotten 2-3k word responses from CEOs of other companies to my essays! These same folks would NEVER have responded in a blog post, so I’m sticking with photos of my dogs for my blog and email for long essays.
What is the goal of Mahalo 3.0 ?
We’re trying to merge content, q&a and search on one page. It’s a really hard thing to do visually, and the truth is no one has ever done it.
Essentially we’re making Wikipedia-style pages with Yahoo Answers and Google search bolted on. The trick is to try and make it not feel bolted on.
How has the mission of Mahalo fundamentally changed, if at all, since you founded the company?
The mission remains the same: To help people find information they can trust.
How we accomplish the mission has changed. At the start I thought we would be 80% search and 20% content. Today we’re 50% content, 30% search and 20% Q&A. So, we will keep playing with the dials until we get it perfect. We’ve got two or three more years of work and I think we will solve the puzzle. If we do, we will have a site that is bigger than the Wikipedia.
Is your goal for people to think of products such as Google, Wikipedia, and Mahalo when looking for information and resources on the Internet, or do see it from a different perspective?
When people think of Mahalo I’d like them to think “the best page on the internet for any topic.”
Additionally, I’d like some percentage of folks to think Mahalo is “the best place to start” their Internet journey. That’s a really hard thing to do, but I think we will take 10% share of the search space in the next couple of years.
I’ve long thought that the changes that Netscape (now Propeller) went through while you were the GM there would greatly influence the future of web content; that is, a combination of user submitted content, original content, and editor-curated content would become the norm. What’s your take on this?
I still believe in that mission, and I think even Kevin Rose does to a certain extent–but on a different percentage. In fact, their Digg Dialoggs are a great example of laying produced content on top of community content. Gawker, GDGT and the New York Times are all doing similar things by promoting consumer content to the top level.
Curation is the future of the internet.
The Knicks… any hope?
Absolutely! The Knicks are going to trade [Eddy] Curry right after Christmas freeing up a lot of cap space.
LeBron [James] will lose to the Boston Celtics in the Eastern Conference Finals and then sign with the Knicks. He will then convince Chris Bosh to join him and the Knicks will win three championships in a row.
A boy can dream right? 
(this post originally appeared on Technorati)