Jason's current workforce is split between two groups: In office staff (even if they're not physically located in the office) and a growing large number of freelance people who are contributing to his goals.

I think that this is an important consideration when asking "what is it really like to work for Jason Calacanis". Currently, Jason is creating a huge (both in opportunity and in scale) archive of topical pages. He's doing this with the help of his management (in office) staff and labor (out of office) contributors.

As a result, I think that the best answer to this question will come from the discovery of these two groups. The easiest way? Become a contributor here on Mahalo and participate in Answers, Page Creation and all of the other great things that Mahalo has started. They paid freelancers / remote contributors $40,000 last month so it's hardly a waste of time.

Generally, wondering what it's like to work for Jason is somewhat irrelevant. Working for someone is a personal / professional relationship and as a result is unique for everyone. Individual employees could try to convey their unique experiences but at the end of the day, Jason will treat everyone a little bit differently and everyone has a different job. The only way to know is to do it.

As someone who worked for Jason for over 3 years, first as a freelance writer then lead blogger for The Unofficial Apple Weblog, then as Managing Editor of Netscape in a virtual work environment, and finally in an actual meatspace office as the initial Editorial Director of Mahalo, I have to agree with Lon's assessment.

You learn a lot working for Jason. You have to be a hard worker. You have to know how to handle stress, because it will be very stressful at times. Jason wants all his employees to be excelling at what they do so that the business continues to succeed because the success of the business is what supports the employees continued success.

If you understand that truth of business, you're a hard-worker, and you have a good attitude, then working for Jason Calacanis can be a great thing.

If not, you'll hate it. I've seen many people who did hate it, but quite frankly, most of those who really hated it are people that I wouldn't want to work with again because they're not hard workers, they're looking for an easy pass, they're willing to settle for mediocre results, and, because of all those things, they don't know how to make great things happen.

This isn't a bad thing necessarily; They're still good people and they'll no doubt be successful in other scenarios. I still count many of these people as my friends.

However, they don't belong in a startup. I do and that's why I worked so well with Jason for so long (I just didn't belong in LA, so I had to leave; now I'm back in New York in another startup). If you don't belong in a startup, you shouldn't be working for Jason. Plain and simple.

I'm a developer here at Mahalo and have worked for, no... with @jasoncalacanis since pretty much the beginning of the project and would never trade an instant of that time for anything else! There are very few companies in existence that has a CEO that is has involved in the dirty and gritty development / scaling process as he is, the flatness of the organization is unprecedented and I admire that.

Day to day, I may have your ups and downs, but in the end when I look back on everything that Jason and Mahalo is, I smile and love what I do.

Now if you dont mind I have to go back to Crushing It :p

ps. I remember when @lon and tyler were hired :)

I was not going to respond to this question. However, after reading all the bulls--t responses, I have to write a HONEST account of what working for Jason is life.

Working for Jason is terrible and that is only to say the least.

Not only does Jason over-work, underpay and totally under appreciate his staff but he is also DISGUSTINGLY disrespectful.

If you don't drink his kool-aid and completely agree with his crazy backwards ideas about Mahalo or life you are fired.

If Mahalo was high school, Jason would clearly be that fat nerdy kid who got his ass kicked daily and later grows up to become a police officer only to cover up his total Napoleon complex.

Jason likes to find weak people who have no other options. While his employees are super smart, Jason fully realizes that if he fired them they would most likely end up back at a mini-mart.

While I worked at Mahalo I sat alongside people with several degrees and even masters...all of them were working WAY below their intelligent level and were also working too many hours, with no REAL benefits and s--t ass pay.

I honestly wait for the day that I see Jason in person so I can tell him face to face what a awful person and even more so awful boss he was.

I thank god daily that I no longer carry the unnecessary stress that Mahalo brought along.

If an employee spoke up about an issue, Jason would just threaten them with replacement.

Honestly, working for aside Jason and having to deal with his crazy ideals and his backward illegal work practices made life miserable. At first Mahalo was F_U_N.

The staff got along, the ideas were not only groundbreaking but also really exciting to be involved with and Jason was barely around.

However, the bubble of fun soon burst and things went downhill quickly. Jason was always being negative and was literally making the staff compete to keep their jobs.

All in all, I am glad I worked at Mahalo because now I know who Jason REALLY is and I will never, ever let another boss take advantage of me or my skill set.

This is NOT the Craig Ferguson Show!!! (although working with Jason can be a lot of fun)
Are you looking for a Hollywood type answer? something that begins and ends in one half hour or hour and you know there is a happy ending at the end of each episode after the commercial break for a comedy, etc. by formula? or do you really want to know?

If you really want to know the answer you need to experience it as we all have been since Mahalo started in all aspects of building the number 2 website in the world from the ground up - one brick at a time. Then you will REALLY know what it is to work WITH Jason, and you would not be asking what it is to be working FOR Jason - because it is not like working FOR anyone, not like Craig Ferguson as Prince Charles and people work FOR him in a late night skit, not like working FOR someone in that you are working in some cubicle on site or in some cubicle working by yourself as a freelancer offsite.

The Jason experience is to work WITH Jason, and you will never "get it" fundamentally until you join in and become one of the team - the onsite team, the how to team, the at home team, the Mahalo user team, the beta tester team, the Twitter commenter team, the This Week in Startups participant and viewer team, the page management team, the Mahalo Street Team, the top 100 Mahalo user team, the person who serves the staffers their lunches and breaks team, the participants in the onsite daily exercise class team, etc. etc. etc. Here are some entry points of many to some of the teams so that YOU can find out WHAT IT IS LIKE to REALLY work WITH Jason and HIS TEAM @ Mahalo:

http://twitter.com/remotev/mahalo my Twitter list for Mahalo of 46 Mahalo members you can follow, some who are onsite team members - you can follow or find links to others or find other Mahalo lists and links and follow from there also

http://twitter.com/jason the personal Twitter for Jason where he posts many other links, events, happenings, announcements, and Mahalo goings on that you can participate in or comment on - he shares his insights freely with the world

http://bit.ly/jasonslist the personal mailing list for Jason "for insider stuff"

http://www.mahalo.com/ register @ Mahalo and click on the tab TASKS and pick a RUSH WEEK task to apply for admission to the how to team, a key team at Mahalo that works with Jason and Mahalo

http://www.mahalo.com/how-mahalo-works How Mahalo Works - everything you need to know to to start to become a real Mahalo team member in all its aspects

Creative Commons Craig Ferguson Stand-up Comedy by rick

As Rob mentioned, there are two types of people working for Mahalo -- those in-house and those in the online community. I am one of the latter, and have been working in the online capacity for 2 years now. I was part of the greenhouse program, then a remote full-time guide, and now a profit sharer.

I'm not sure where to begin actually. I could write volumes on all I have learned since joining up with Mahalo. I have always been a freelancer.....but I worked in film/television production. So, I know a thing or two about working a gazillion hours and then some to try to get something off the ground. Also, I understand what it is like to work with a variety of colorful personalities. I tend to be a diplomatic person -- something I am naturally, but skills I honed even more while working in production. I kinda feel like that is exactly what one needs to have while working at Mahalo too --

What I feel like I have learned working for Jason in the online capacity is that you need to be a diplomatic person, hard worker, and always willing to adapt. I guess the adapting part is what start-ups are all about, and what I have had to work at the most. I am good at acclimating to change, but I would be lying if I said adapting to Mahalo's growth and changes have been easy for me. I have had to change my work approach a lot in the last 9 months. Ultimately, all the changes have proven fruitful for me, and I hope for Mahalo as well. I am one of the first round of remotes that were released into the profit sharing work force, and one of a handful that have continued to make the community a full-time job. I have done that because I believe in Mahalo and what it has to offer -- I think the brains behind the project are what makes me keep plugging. I am referring to Jason, of course, but also to Lon, who I have had the pleasure to work with a lot in cyberspace the last nine months. I think part of Jason's talent lies in hiring the right people to help him see his ideas through.........in-house and online.

So, to really answer the question? Working for Jason has been a rewarding experience for me because I have learned so much -- about the internet, about people, about working for and with others toward a common goal -- which is to make mahalo a great place. It doesn't really matter that I don't know Jason on a more personal, working level -- I have only met him once, very breifly -- because I think the way the community thrives is Jason at work.....and I am working with the community. I like how Jason is involved in the community, how he makes his presence known and puts himself out there. He wants to know what users like and dislike, and make improvements accordingly.

Mainly, I like that Jason has given me the opportunity to work for a great company from home. I was getting tired of production, and this work is perfect for an aspiring writer that likes to travel. I can pack up and head out, working on the road, and that is just awesome. Thanks Jason......

I've worked remotely from home here in Canada for Jason for three years now, first briefly at Netscape and now for the past two years with Mahalo.

Unfortunately I've never had the chance to meet Jason in person but I do know the fundamentals of what Jason is looking for in an employee and even remotely I've done my best to achieve these goals as I'll work night and day on Mahalo whether I'm on the clock or not because and since his kool-aid is so tasty I even do it with a smile and full of optimism.

For me, this is the most exciting startup to work for today on the web. I thought that when I signed up for the Greenhouse back in the summer of '07 - He has not disappointed, it seems with every improvement Mahalo makes the site just gets better, I have no reason to think this trend won't continue.

I hope to meet Jason someday, maybe in a year or two a "Mahalo Page Managers Convention" won't be a bad idea. @robbrown, @wdawe, @girlieq3000 and @christhomson will man the Canuck table.

I saw C. K. Sample's tweet that anyone who ever worked for Mahalo.com should answer this question, so here I am.

To ask what it's like to work for Jason Calacanis, or anyone, is to solicit a range of subjective answers. Mine can't help but be equally subjective, but because I have to assume the question was asked in good faith (too bad the questioner is anonymous - what's up with that?) I'll try to answer the same.

To understand the source of my particular brand of subjectivity, here's a little context: I was recruited to Mahalo.com by the CTO and one of the developers back in April of 2007 -- before the "public alpha" launch of the site.

I did my due diligence on Jason before I signed on. I knew he was a mid-level tech entrepreneur respected enough by investors that people with more money than he had were willing to give him some more. I knew he was seen as headstrong, opinionated and bullish. I took in some interviews he did (and hosted) and recognized that he enjoyed a fight and seemed to relish in being right.

Hey, I'm opinionated. I don't back down from a fight. Everyone's an a$$h0l3 to someone, and I'm certainly not excluded from that rule. So, okay. In for a penny, in for a pound.

I believed in the company enough to drive a 175 mile commute (total each day) five days a week, to and from the office. This, along with not-uncommon nine hour-plus days (four with working lunches) and occasional off-hours work, meant I was dedicating seventy to eighty hours per week to Mahalo.com, minimum. I did this because I believed in the product, I appreciated the creative challenge, and I liked my co-workers.

Shortly after I started at Mahalo, I helped conceive, develop, manage and steward the Mahalo Greenhouse, and I served as unofficial, and then much later, official, Product Evangelist once the Greenhouse was more or less automated and we began to develop the second phase of the site. In October of 2008, I was laid off along with half of the in-house editorial staff and a good number of developers. After the layoff (which came as no surprise to anyone who followed the news coming from our primary investor) I worked briefly for Mahalo.com as a freelancer.

So there's the back story. Now the subjective-but-hopefully-fair stuff. :-)

Working at Mahalo.com in those early days meant working side by side with Jason, along with C.K. Sample, Lon Harris (see their Answers higher in this thread) and the rest of the team of more than three dozen folks. Ideas were solicited in a creative soup around the lunch table four days out of five. It was exhilarating to dive in and speak up and learn along the way. My own persistent urging that humans (the users) be involved in the human-powered search site we were building directly influenced the creation of the Greenhouse, and that's something I still take pride in.

No one can deny that Jason Calacanis is an excellent self-promoter. I don't use that phrase in the negative sense! As an independent creator my whole life, I know you have to believe in yourself and your product in order for others to feel the same way. Jason's apparent relentless confidence is infectious and, at least initially, inspiring.

Jason is famously vocal about his idea of the ideal work ethic. Google around or just read some of the other comments in this thread -- I think it's fair to say that Jason believes that the only acceptable attitude toward work is one that is identical with his own: Long hours, personal sacrifice and dedication to the project to the exclusion of all else is the only way to succeed.

In my opinion, based on my experience with him, Jason equates exhaustion with loyalty. Loyalty feeds validation. In my time with Mahalo, I saw Jason's apparent opinion of some employees diminish because they, while otherwise intelligent, creative, engaged and productive contributing members of the staff, did not share his Ideal when it came to a work ethic.

I disagree with this, as do many productivity experts. Balance in life -- working to live rather than living to work, to put it simply -- typically increases productivity, creativity, innovation and yes, loyalty.

To work successfully with Jason, you must have the same views about work as he does, or you must be willing to subsume your views for the duration.

I mentioned the open, actively participatory atmosphere in those early days at Mahalo. The feeling that each person's serious, reasoned idea, no matter how far out in left field it might initially seem, was heard and considered, was, for me, at least, the most rewarding reason to work for Jason. I felt -- as I believe many of us did -- that we were truly contributing to the creation of something that was special.

After a while, though, two patterns emerged that chipped away at that feeling of contribution and worth.

One was -- and I say "was" because I don't know if this is still Jason's practice -- his habit of letting ideas come from us until one person finally said what he wanted to hear, at which point he would say, "That's the right answer." The right answer was only right because it was the one he'd already decided upon. It made the whole exercise feel like a waste of time, but more often than not we laughed it off. Sometimes, though, you could see the frustration on the faces around the table.

The other demoralizing practice was his use of what we all called "Calacanimath" -- quick, often wildly inaccurate estimations that supported whatever point he was making. Attempts to correct him or provide evidence that conflicted with the Calacanimath result were often brushed aside.

To be honest, I think it's likely Jason is unaware of how stifling both of these quirks are to willing and "best and brightest" collaboration. Sometimes the best way to learn is to be wrong... and Jason rarely admits to being wrong, at least not directly. In my time working with him, the times he admitted error -- especially in interpersonal relationships -- were so uncommon as to be remarkable.

So, in my experience, to work with Jason Calacanis is to accept that your ideas are only as valuable as they are in line with his vision. Which some might say isn't so bad -- after all, he's the boss. On the other hand, in a room full of people bringing different perspectives and experiences to the literal table, it's best to be flexible with that vision -- you might see more.

Jason's signature steamroller-style, seemingly good-natured and unswaying personal drive is perhaps the strongest source of his success to date. Again, I admire a strong personal drive... but for Jason, this single-mindedness sometimes causes him to make choices and act in ways I could not support.

I will not point to specific examples, but rather describe varieties of situations.

Jason (at least in the time that I worked with him) pursued choices -- always, I believe, with the best interests and success of Mahalo.com in mind -- that were ethically cloudy.

Additionally, his work ethic expectations for employees sometimes ran contrary to the expectations of labor law.

Finally, I witnessed several instances of treatment of employees that was disrespectful and dehumanizing. There's nothing wrong with being what Lon Harris called "frank, blunt and direct," but one should always treat others with respect -- even more so when one is in a position of leadership and hopes to be treated with respect in turn.

Like Jason, I find it hard to keep my mouth shut about things I believe in. Many times, this put us in in opposition. He once warned me of being an advocate for the sake of being an advocate. I believe a strong sign of a need for advocacy is the denial that such a need exists. Unfortunately, our opinions on many things may never converge.

So. What's it like to work with Jason Calacanis?

It's a roller coaster, and the degree of the peaks and valleys is directly related to your personal ability / willingness to let him control the ride. If your personality, ethics, and interpersonal attitudes are complimentary to his, you'll likely go around again and again. Enjoy it, if it's for you. Make sure it is for you -- you'll sleep better at night.

I believe that Jason Calacanis is a good person whose drive for success tends to overpower his better angels. I sincerely wish him, Mahalo.com, and any of my former colleagues who are still at Mahalo.com the best of luck -- may all their yachts have laser cannon gun turrets when those fabled stock options finally come in.

I hope this has all come across with the fairness and equanimity I intend. The fact that I've spent the time to write over 1,400 words that I could have dedicated to my National Novel Writing Month effort should be an indicator of my sincerity and that my motivation is one of caring. And yeah, Jason -- any time you want to sit down and yak about this face to face, I'm game!

Best,

Matthew Wayne Selznick

I am a current, in-house employee at Mahalo and I have to say working for Jason isn't the easiest thing. I wouldn't have it any other way though, he's constantly challenging everything we do and asking, why wouldn't we do something different. I think it's a good thing to keep every level of the company transparent, I work with server infrastructure and architecture and I think most of the people in the company can tell you, at a pretty high level, how the databases and web servers are laid out. I know Jason can, which is not something a lot of CEOs can say.

I've worked for and with some difficult people and I'd have to say Jason isn't difficult, he's inquisitive. My first job was at a record company and I have to say that anyone who thinks Jason is a hard guy to work with should spend some time at a record company. Record execs are some of the most ruthless, cut throat people on the planet. They'd stab you in the back in a second if it benefited them in any way.

I've heard it said about Jason that he'll never stab you in the back, but he might stab you in the face. I think it might seem that way, but its not the truth. I think Jason will question your choices and if you're a professional you should be able to answer any questions without hesitation.