Startup LA: Fighting the Fight with Jason Calacanis

This article first appeared on Bub.blicio.us November 23, 2007. Jason Calacanis is known for his direct delivery style and he had some strong words for entrepreneurs on what it takes to fight and conquer. In light of ongoing occurrences with start-ups trimming staff and cutting budgets it seemed appropriate to re-post.

“Business is not about being nice. If you want to be nice go to a church social.”
- Jason Calacanis

Ah. The infamous Jason Calacanis. I’ve heard so much about him over the years and even remember pitching SA Reporter way back when during the boom. Now here we are a short 9 years later and I’m attending the Fireside at Startup LA with him and host, LA’s own, Heather Vescent.

I don’t know Jason as a person at all and have only met him a handful of times, almost every time with him giving me a look of total lack of recognition and “yeah, what do you want?” all over his face. I was told recently that this is a tactic he uses just to see how people will react. Good thing then that when he shook my hand limply at Startup LA and said, “Yes, I remember you” in a totally bored voice I simply said, OK, and turned around and walked away. I’m not one of those ass-kisser types no matter how many people want you to sign their napkin.

It was with great curiosity that I sat down at a table in the front with my purty little Macbook popped open in front of me with Bub.blicio.us name tag proudly on display to capture the entire conversation word for word. You always hear, “You either love Jason or hate him. There is no in-between.” I was looking forward to watching him go and go he did.

Instead of drafting a gigantic summary I’ve decided to keep with the theme of my previous post and give you a list of my favorite takeaways (and to save certain tech industry celebrities further embarrassment.) Some are direct quotes, some are paraphrased, all are 100% authentic.

Editing down is also good since it allows me to exclude the many, many F-bombs Jason was throwing out like a frenetic water balloon toss at a family picnic. Apparently this is one way to tell when he’s had a really great day. Which begs the question, what does he say when it’s a bad one?

He had some gems and I understand even more why he’s successful, feared and admired. His approach is…how should I say this…Unique? Crazy? Focused? Aggressive? Manipulative? Driven? Yeah. That kinda sums it up.

And now, on with the Jason Calacanis show…

1) Jason was a psychology major, which explains, well, a lot.

2) Jason thought he was going to grow up to be a cop and then join the FBI but then he got into computers and video games at the age of 12 and it led him into the early world of technology. He first got on the Internet in 1988.

3) When asked to describe qualities of an entrepreneur the first three he named were: paranoid, delusional and arrogant… he joked (but not really) that he was trying to think what words people use to describe him.

4) For Jason there is no such thing as having a healthy lifestyle if you are an entrepreneur. He asked the audience if any entrepreneur present maintained that kind of balance and someone raised their hand to which Jason shouted out, “Bullshit!”

5) To the chagrin of all the people in the audience fighting to prove LA is a force to be reckoned with Jason commented that he doesn’t think LA is the best place to do a start-up company. Yet, he lives here because he likes it and because, at the end of the day, it’s up to you how your start-up does, not the environment around you. “You can make a business work anywhere…it’s the dedication, not the location.”

6) Jason wakes up every day thinking about and preparing for the many ways his competitors want to kill his company, and vice versa. (The word “Kill” and “Fight” were common threads to the underlying business philosophy presented.)

7) “When shit is going down you have to be cool as a leader and not panic.”

“It’s fucking war when you start a company. Look at your competitors and kick their ass. That’s what it’s about. Everything is fair. Cut their legs out from under them and compete.”

9) I won’t go into the details of the cuh-razy story he told but here’s the basic gist: If there is a competitor that you want to hurt, truly wound in the deepest way, steal their best person and have that person send their resignation while said competitor is in the air to receive upon landing at their vacation destination on another continent, rendered completely helpless and thus ruining their good time, on purpose. Damn.

10) “Facebook is really about Google and Microsoft fucking with each other. If you’re not willing to mix it up and fight when competition comes you will get crushed.”

11) Regarding the life of an entrepreneur: Resiliency is the number one attribute in his mind. “You have to be because every day you will wake up and feel you can take on the world. You throw stuff against the wall and then the next week you’re like MJ hitting it with your eyes closed and you win. You have to be prepared for the roller coaster of great moments and the incredible tragedies. It’s a horrible life in many ways.”

12) “By the 3rd or 4th company you start to see themes in your career, where you say, ‘I’ve seen this pattern before.’ When you see the same patterns start to emerge, follow your nose.”

13) “Video is a huge trend and people’s behavior is changing how you watch it. The concept of watching an entire film on an iPhone was ridiculous but now every time I go on a flight I see people watching movies on iPod’s or on your laptop in bed. The creation of video is changing. Some of it is shifting to other places…Video is going to be big.”

14) Regarding what he wished he’d known at the beginning: “The biggest thing is about people…I always felt I could work with people and change them and motivate them. It was a fools errand and not true. You have to pick great people and treat them well. If it’s not the right person fire them as quickly as possible and don’t try to work with them at all. It’s a waste of time. It’s a war. If you go to war and you’re going up the hill and there are 5 or 6 people in the platoon and one doesn’t want to be there and isn’t paying attention they’re going to get the other 5 people killed. You have to look at it like as if they are a 3 out of 10 and rest are 10 out of 10. You can always replace that 3 with someone who is a 10. The rule is: no one can do “good” work at a company. You can only do very good or excellent work. If you only want to do good work go work for Starbucks or somewhere else because that is not what being at a start-up is about and it’s not fair to the people who are working 18 hours a day trying to kill it. And it makes the people running the company look bad. I tried being a nice guy. Fuck that. It doesn’t work. You have to move on.”

15) “The second your gut tells you it’s not going to work out you are 99% correct.”

16) Jason does an excellent impersonation of Arianna Huffington.

17) The good and the bad on being acquired: “The good is the wire transfer. The bad is everything else.”

18) For an entrepreneur the driving force is about building a product not making the money. He built Weblogs Inc. because he loved blogs. A lesson we should all remember…following your passion will bring the money to you.

19) “A lot of entrepreneurs are full of shit when saying it’s not about money because it is about money just not ONLY the money.”

20) “Business is survival of the fittest. Certain people give up and other people keep going. You keep pounding and pounding. Columbus went the wrong way and it turned into the most glorious voyage of his time.”

21) Competitive tactic: “Instill in your competitors that they should give up.”

22) “…Sometimes you [your company] does die but who cares, you can start again. Failure makes you a hero here [U.S.]”

23) On risk: “There’s no downside. Why wouldn’t you do it [risk?] People will sit there and not put themselves in the game because they’re scared. People overestimate the downside of risk in everything. Just fucking go for it and fail and by the 5th time…even a blind man can hit a baseball if he keeps swinging the bat. It is the law of odds. You could have the stupidest idea and you swung the bat and watch the ball whiz by. Just keep slogging through it.”

24) On the highs and lows: “Fear of failure is a great motivator for people. I’m scared to death to fail. I want to succeed. Any entrepreneur who says they aren’t scared of failure is lying. A healthy fear of failure is good as long as it’s not disabling for you.” [Motivation at Weblogs was refusing to lose to Denton.]

25) “In the hierarchy of needs, competition is low level but it’s also a powerful motivator.”

26) On keeping your team enthused: “Make people feel great and repeat the mission to them over and over again to keep them focused.”

27) Jason always tries to participate in university-related speaking invitations. He echoed the sentiment from the Success Stories panel that it’s important to give back as a mentor and resource.

***

And with that our hour with Jason Calacanis comes to a close. Phew. Just reliving it through my notes has me hopped up. I hope you enjoyed these morsels as much as the entrepreneurs and industry friends in attendance. Didn’t I tell you there were some gems?

…Now get out there and take over the world people!