Posts Tagged ‘Jason Calacanis’

January 31, 2013

Start-up Blues

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I drew this car­toon because a recent story in the news made me sad:

A lively and popu­lar figure of the start-up scene, Jody Sher­man com­mi­ted suicide.

I didn’t know the guy, but we had mutual friends, like Jason Cala­ca­nis and Tony Hsieh.

Jason sum­med it up well: “And it seems like folks are not ready to talk about that issue just yet. Which I can understand.”

This is the second star­tup sui­cide in a month, after poor ol’ Aaron Swartz. We are gene­ti­cally pro­gram­med to have our our tiny brains fried by the sui­cide of some­body we care about; wri­ting about it well is impos­sibe at the best of times. But here are some of my own mea­gre, insuf­fi­cient thoughts:

1. My dee­pest con­do­len­ces to Jody’s family, ese­cialy his wife and chil­dren. The sorrow must be horri­ble, simply horri­ble. I am so sorry, truly.

2. Once we’ve made our millions, reti­red and got­ten old and dec­re­pit, hey, then DEATH is not so scary an idea, but when one is still in one’s prime… Most of us doing the start-up thing are still in our prime, so natually DEATH is ama­zingly strange and alien to us.

3. The start-up life, for all the time we spend glo­rif­ying it, is a very tough road. Again, Jason says it well:

Perhaps we owe it to these three ama­zing humans to exa­mine if the pres­su­res of being a foun­der, the pres­sure of our community’s relent­less pur­suit of great­ness, in some way con­tri­bu­ted to their deaths?

I’ve always belie­ved that being a foun­der is an unhealthy pur­suit at times, and few have disa­greed — cer­tainly not those who have done it. Read any bio­graphy of a suc­cess­ful foun­der and you’ll find colla­te­ral damage around — and cer­tainly in — those individuals.

Star­tups are a full-contact sport. This is a good time for all of us to pause and think about why we’re doing this. And the impact it’s having on us and the peo­ple around us.

4. Me and my friends in the sart-up scene aren’t spring chic­kens any­more, for the most part. We’re the old guard now. And as Karma catches up with us and the hard choi­ces we made, our deaths are going to start get­ting a lot more common.

5. As I’m fond of saying, anything worth doing will cost you your life, even­tually. Best make sure it’s worth it, make sure it’s something your dee­pest self actually wants.

6. Yes, your dee­pest self, not just your glib, sexy, bullshit self.

7. This is it. Fight like hell. Godbless.

April 24, 2010

daily bizcard 05: jason calacanis

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Today’s Daily Biz­card, “Soup” goes to Jason Cala­ca­nis.

Web 2.0 serial entre­pre­neur Jason is one of the smar­test peo­ple I know. Some peo­ple find his man­ner abra­sive, but eh, that’s just his high-energy, take-no-prisoners, no-bullshit way. He’s a real gent­le­man and a sweetheart if you ever actually spend time around him.

The car­toon is all about cut­ting cor­ners. It’s a really temp­ting and easy thing to do, espe­cially when busi­ness is slow. The down­side is that ine­vi­tably peo­ple do notice even­tually. Of course they do.

[The Daily Biz­card archive is here etc.]

[Jason, please send me an e-mail at gapingvoid@gmail.com with the details you want to see on the back of the card, and I’ll send a free batch of 100 to you. Thanks!]

February 28, 2010

random thoughts on being an entrepreneur

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[The “I’m Not Delu­sio­nal” print, for sale on the gallery…]

Ran­dom thoughts on being an entre­pre­neur. [Ori­gi­nally pos­ted January, 2007]

I wouldn’t say I was an autho­rity on entre­pre­neurship, cer­tainly not in the same lea­gue as peo­ple like Fred Wil­son or Jason Cala­ca­nis. That being said, the last cou­ple of years haven’t been too shabby, either. With that in mind, here are a few thoughts I have on the sub­ject, in no par­ti­cu­lar order. The list, by the way, is far from com­plete– I’ll pro­bably be adding to it soo­ner than later etc.

1. Everything takes three times lon­ger than it should. Espe­cially the money part.
2. The best way to get appro­val is not to need it.
3. Peo­ple want what they can’t have. In fact, that’s pretty much all they do want.
4. Once you become an entre­pre­neur, you find the com­pany of non-entrepreneurs a lot har­der to be around. You’ve seen things they haven’t; the wave­lengths alter, it’s that sim­ple.
5. In a world of over-supply and com­mo­di­fi­ca­tion, you are no lon­ger paid to supply. You’re being paid to deli­ver something else. What that is exactly, is not always obvious.
6. Word of mouth is the best adver­ti­sing medium of all. The best word of mouth comes from dis­rup­ting mar­kets.
7. Peo­ple buy your pro­duct because it helps fill in the narra­tive gaps in their lives.
8. You can either be chea­pest or the best. I know which one I pre­fer.
9. Some peo­ple think that once they secure ven­ture fun­ding, their pro­blems will be over. Wrong. That’s when your pro­blems REALLY begin.
10. It’s bet­ter to be under­fun­ded than over­fun­ded.
11. If an ave­rage guy in a bar can unders­tand what you do for a living, chan­ces are you’re half­way to beco­ming a com­mo­dity.
12. It’s easier to turn an ally into a cus­to­mer than vice versa.
13. If you’re happy in your career before the age of thirty, you’re pro­bably doing something wrong. Heck, if you’re happy in your career before the age of seventy, you’re pro­bably doing something wrong.
14. Smart, young, artis­tic peo­ple are always asking me which is a bet­ter career path, “Crea­ti­vity” or “Money”. I always ans­wer that it doesn’t mat­ter. What mat­ters is “Effec­tive” and/or “Inef­fec­tive”.
15. Write the follo­wing on a piece of paper, have it fra­med, and stick it on your office wall: “Have you hug­ged your cus­to­mer today?”
16. Peo­ple will always, always be in the mar­ket for a story that reso­na­tes with them. Your pro­duct will either have this qua­lity or it won’t. If your pro­duct fails this test, quit your job and go find something else. Just making the pro­duct inc­re­men­tally chea­per or bet­ter won’t help you.
17. Pro­ducts are idea ampli­fiers. The mole­cu­les and/or bytes are secon­dary.
18. Peo­ple remem­ber the qua­lity long after they’ve for­got­ten the price. Unless you try to rip them off.
19. Mar­kets serve entre­pre­neurs bet­ter if the lat­ter can keep the for­mer under­sup­plied. Over­supply is the kiss of death.
20. I per­so­nally know a for­mer CEO who, once he attai­ned con­trol of the com­pany, ran an EXTREMELY pro­fi­ta­ble busi­ness into the ground in less than two years. From a mar­ket cap of $100 million to ZERO, just like that. Why? Short ans­wer: He loved being “The” CEO, but he didn’t much care for being “a” CEO.
21. In terms of beco­ming an entre­pre­neur, pro­bably the most use­ful thing I lear­ned in the last twenty years was how to enjoy my own com­pany for long stretches of time.
22. One suc­cess­ful entre­pre­neur I know well has a won­der­ful qua­lity, namely that he never, ever com­pa­res him­self to other peo­ple. He just does his own thing, which actually ser­ves him rather well. Just because his com­pe­ti­tor has bought him­self a big­ger motor boat, doesn’t mean he feels the need have a big­ger motor boat. This qua­lity helps him to build his busi­ness the way he sees fit, not the way the motor boat peo­ple see fit.
23. Run­ning a star­tup is full of extreme ups and downs. Which is why so many suc­cess­ful and happy entre­pre­neurs I know lead such nor­mal, sta­ble, ungla­mo­rous, “boring”, family-centered lives. Somehow they need the lat­ter in order to balance out the for­mer. Extra-curricular drama looks great in the tabloids, but that’s all it’s ulti­ma­tely good for.
24. MBAs are con­di­tio­ned to use their brains in much the same way as sex wor­kers are con­di­tio­ned to use their geni­tals. Nice work if you can get it.
25. Bill Gates may have a million times more money than me, but he isn’t going to live a million times lon­ger than me, watch a million times more sun­sets than me, make love to a million times more women than me, drink a million times more fine wines than me, lis­ten to a million times more Beetho­ven String Quar­tets than me, nor sire a million times more chil­dren than me. Human beings don’t scale.
26. F. Scott Fitz­ge­rald once wrote, “There are no second acts in Ame­ri­can lives.” F. Scott was a drun­kard and a fool.

February 17, 2009

dear crazy, deranged fools…

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[UPDATE: Please sign up for the “Crazy, Deran­ged Fools” News­let­ter. Thanks!]
Dear Crazy, Deran­ged Fools,
For a while, I’ve been thin­king about what to call y’all collec­ti­vely, i.e. the peo­ple who follow my work with regu­la­rity.
My friend, Jason Cala­ca­nis calls his regu­lar rea­ders “Jason Nation”. I thought that was very cle­ver; I liked it a lot. Hey, it rhy­mes! In a simi­lar exer­cise in word­play, I thought about “Voi­det­tes”, “Gaping­voi­ders”, “Hugh­trai­ners” or wha­te­ver, but nothing really stuck. I guess that’s because these kind of names were “All About Hugh”. And, well, let’s face it, it isn’t all about me– you guys have your own stuff going on, as well. That’s what makes it inte­res­ting.
So what uni­tes us? The ans­wer came to me in flash this mor­ning, in a blog post:

A. Most peo­ple work for the money. Most peo­ple wouldn’t do their jobs for free.
B. Most peo­ple hate their jobs.
But I’m not thin­king about “Most Peo­ple” right now. I’m thin­king about the small per­cen­tage of the popu­la­tion who want to love their work; who want to find mea­ning in their work… and are willing to work like hell to find out how.
Those crazy, deran­ged fools…
How do they manage to exist? How dare they exist!
Are you one of them? Just curious…

A Crazy­De­ran­ged­Fool [CDF for short] is, like me, some­body who has the teme­rity to aspire to work in a way that pro­du­ces both joy, mea­ning and con­tri­bu­tion for both them and others, while also paying the bills. It’s about crea­ti­vity, it’s about fin­ding mea­ning, but it’s also about living in the real world. That’s the rea­lity I want to live in, and from the vast quan­ti­ties of e-mails and com­ments I get from y’all, that seems to be your game plan, as well.
I really liked what Ms Cons­tan­tine said in the com­ments of the afo­re­men­tio­ned post:

I’m wor­king about 30 hours a week on top of my “day job” so that one day I’ll be able to do the work I love.
I’m currently doing the extra hours for free, so I’m kind of one of them.
Gotta pay the bills though.

Ms Cons­tan­tine, that too has been my life for the last twenty years. I too am a CDF. This IS INDEED the crazy, deran­ged, foo­lish world of my own making that I chose to live in. And this IS INDEED the crazy, deran­ged, foo­lish world I will die in. I’ve already cros­sed the Rubi­con. Alea iacta est. There is no going back. Ever.
With Love and Res­pect to You All,
Thank You. Seriously. Gods­peed!
–Hugh MacLeod

July 13, 2008

cheapeasyglobal

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[Car­toon ori­gi­nally published Decem­ber, 2007. It was dedi­ca­ted to my friend, the daunt­less Robert Sco­ble.]
As anyone who has been rea­ding Techc­runch will know, the “Is Blog­ging Dead?” meme has rea­red its ugly head again.
Well, before we all get dres­sed up in our best fune­ral gear, let me say it one more time: The big story is not about blog­ging. It’s not about Twit­ter, You­Tube, Face­book, Friend­feed or wha­te­ver. And it cer­tainly is not about Robert Sco­ble, Mike Arring­ton, Jason Cala­ca­nis, Nick Den­ton or wha­te­ver so-called “A-Lister” you care you men­tion.
Yes, again, it’s all about what Clay Shirky said four years ago, in a won­der­ful inter­view he did for Gothamist:

“So for­get about blogs and blog­gers and blog­ging and focus on this — the cost and dif­fi­culty of publishing abso­lu­tely anything, by anyone, into a glo­bal medium, just got a whole lot lower. And the effects of that inc­rea­sed pool of poten­tial pro­du­cers is going to be vast.”

I had cof­fee with Clay a cou­ple of weeks ago. A totally great guy. We didn’t talk about blogs much. Nor did we talk much about Twit­ter or Face­book.
We tal­ked about something con­cep­tually far sim­pler: Cheap. Easy. Glo­bal. Media.
Chea­pEasy­Glo­bal is the big story. And it’s here now. It has arri­ved. And it’s per­ma­nent. And there’s not a damn thing anyone can do about it, save for a nuc­lear holo­caust.
Some peo­ple will do very well by it. Other peo­ple will pre­fer to stay on the side­li­nes ins­tead, using the inter­net to yak yak yak end­lessly on about what other peo­ple are up to, hol­ding the “pla­yers” to far higher stan­dards than they will ever attain them­sel­ves. These lovely armchair quar­ter­backs will be swiftly for­got­ten by his­tory. Same as it ever was.

April 18, 2008

gillmor gang joins the techcrunch network

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So it looks like my friend, Steve Gill­mor is wor­king with Mike Arring­ton now. Jason Cala­ca­nis breaks the story, with the above car­toon on the blog post. The Gill­mor Gang’s new per­ma­nent home is here.]
Jason writes:

Here’s some exc­lu­sive news: after being offline for over a year in a legal dis­pute (can’t get into details) the Gill­mor Gang is back and is part of TechC­runch! Steve Gill­mor is one of the most insight­ful minds in the tech­no­logy space, and his “gang” is a free-form thought-fest that unpacks, repacks, and dis­tracts memes fas­ter than any other con­ver­sa­tion out there.