Master of 500 Hats

Great Entrepreneurs are PASSIONATE about Customers & Products, NOT about being Great Entrepreneurs.

yeah, that's a super long-ass headline, i know... it's a personal soundbite from a Stanford BASES E-Challenge panel discussion i participated in earlier tonight over on campus.  probably plenty of other people have said something similar previously, but i'll at least claim some original thought.

(note: i've been on blog vacation way too damn long... since before i left for Japan in December really.  sometimes if you're not feeling it, you just need to take a break.  hopefully i'm back now)

here's my point -- Silicon Valley is WAAAY too infatuated with the ELEGANT IDEALISM of Entrepreneurship (or the GOLLUM GREED of making a shitload of CASH) , rather than the GRITTY REALITY of running a CRAPPY little startup business that will likely GO NOWHERE... which if you've ever been through it, is a tough, painful, low-probability motherfuck of an adventure, aka tragedy.  it ain't no merry go round folks (well it is, but not the way you think... probably rollercoaster is a better way to describe it).

now please don't get me wrong.... i'm not here to shit all over your enthusiasm for building a startup.  nor am i saying there is anything bad about wanting to make money, or wanting to be your own boss, or to valiantly attempt to defy the odds and create the next Google or whatever. 

but i DO hope some of you young-ass whippersnappers get your heads out of your collective asses and get a little more practical about what you're likely to encounter should you decide to do your own startup.  and a little more real about what you may face at the end of a rough hand of poker.

to wit: the first time i tried to do my own business, it took 7 years of hard work, below market pay, near bankruptcy (2 or 3 times), broken friendships, damaged relationships, credit card debt up to my ears, ridiculous stress, several missed opportunities for big paydays as a grunt at Microsoft, Intel, Netscape, or Yahoo, all in exchange for a piddly-ass half-million acquisition that barely got me enough cash to put a down payment on a small condo in SF.  sure it was a good lesson in learning how to [NOT] run a business, but it was a HARD goddamn lesson.  and one i'm pretty sure i never want to repeat. the fact that i still wanted to try and go back out and do another startup AFTER that first effort is prime evidence that i'm either crazy, stupid, or both.

another thing i said tonight is running a startup for the first time is a lot like being a teenager driving a car at high speed -- in fact many high schoolers learning to drive are required to watch a movie about fatal car accidents / drunk driving consequences (WARNING: don't click thru if graphic images disturb you).  those movies are sobering in every sense of the word, and they do serve a useful purpose -- to provide negative incentives against doing something stupid that could result in severe harm to you or others. 

well most people in venture capital or business school won't tell you this, but first-time entrepreneurs are just as friggin' dangerous as drunk teenagers behind the wheel of a speeding automobile.  mostly to themselves, but possibly also to their employees, customers, investors, or family.  now every once in awhile, one of them actually manages to make it across the finish line with flying colors... and unfortunately their success may justify VCs throwing their cash away on not just that 1% but also the other 99% who may end up mangled along the side of the road.  but that's how it goes -- VC is a hit [and run] business.  you just gotta hope you're the Super Model 1% and not the other Wham Bam Thank You Ma'am 99%.  Good luck, sucker.

(um dave: wtf does this have to do with your headline dude?  hold on buddy, i'm getting there...)

ok, so i have i put the Fear O' God in ya yet?  good.

now, if you're still with me at this point, you must be serious about being an entrepreneur.  only crazy, ignorant, passionate people would still be reading this, thinking that startups are worth all this hassle.

so when i say "PASSIONATE", what i really mean is PASSIONATE about SOLVING A PROBLEM, and PASSIONATE about BUILDING A GREAT PRODUCT or SOLUTION.  it does NOT mean you're infatuated with the idea of being an entrepreneur or a great leader (yeah, bullshit... i know you're still in L-O-V-E LOVE with yourself, but maybe after i've kicked you in the startup balls a few times you'll be less likely to engage in this mental masturbation without a little reality check). 

hopefully, being PASSIONATE means you are driven to make someone's life better by understanding their PROBLEM, and perhaps helping create a great SOLUTION to that problem, and possibly even making a buck by actually DELIVERING it to them (... at the cost of $.99 or less, we hope). 

ok, enough of this drivel.... get back to work. 

BUILD something, dammit.

Well whaddya know... Yes, We CAN.

thank you america.  now, let's get to work.

Finishing Dead Last... is Still Finishing.

I'm not an Olympian, but some days i still get out and try to act like an athlete (if you count Ultimate Frisbee a sport, and i do).

I'm not a great entrepreneur, but i ran a small business for a few years & managed to make payroll happen (most of the time); these days i try to help others with theirs (or at least avoid some of my mistakes).

I'm not an A-list blogger, but every once in awhile i write a half-decent post and maybe get a headline on TechMeme for 15 seconds (but most folks still hate my font choices).

recently i've had a lot of stuff on my mind, and it's been a little tough to get rolling on some projects i'm working on.  I don't really have any excuses; some days i just don't feel motivated.  some days i just feel old & tired.  some days i just do my best to put one foot in front of the other.

for those of you who occasionally feel the same way, i think you'll enjoy Ben Parr's 7 Lessons Olympians can Teach Entrepreneurs, and in particular the clip on Derek Redmond from Barcelona in '92 makes an impression:

You could say the same for Gabriela Andersen-Scheiss in the '84 womens marathon, or more recently just yesterday when the US mens gymnastics pulled a Bronze medal out of their ass. 

All of these folks decided to push just a little harder, and finish... even after they knew they weren't coming in first.  or second.  or even twenty-second.

Here in Silicon Valley, so many of us are obsessed with the big home run, the grand slam win, the next Google or YouTube or PayPal or Microsoft or whatEVAR.  Often, we don't stop to consider how important just getting on base is... whether it's a single, a walk, or even getting hit by a pitch.

Now i'm not saying it doesn't suck when you don't win... hey, no bullshit there: it sucks.  But many times we tend to forget what an achievement it is just to finish the damn race... even if it means coming in dead last. 

note to self: finishing dead last is still finishing.

so FINISH, dammit... get your ass across that line.

The Problem with the Zuckerberg-Lacy interview @ SXSW: Sarah's not a Geek.

So i'm still in shock at what happened a few hours ago at SXSW during the Sarah Lacy interview of Mark Zuckerberg.  I'd like to be nice about it & i feel for Sarah, but to be brutally honest i don't think i've ever seen such a complete & utter train wreck of an interview before.

As several of us noted in the audience and in the twitter avalanche that ensued (almost a pseudo-sxsw backchannel, tweets were flying so fast), it was an astonishing case of Nuclear Fucking Fail.

It was uncomfortable from the very beginning, and not just because of Mark's well-known shy nature.  Sarah conducted the interview in a very personal fashion, assuming a familiarity with Mark that was obvious she didn't really have.  Whether or not she's interviewed him 30+ hours for her upcoming book, she just never connected well... with either him, and most especially NOT with the audience.

Now Mark can admittedly be a challenging interview, and it might be normal for a reporter of even Sarah's stature to be slightly nervous interviewing him in front of 2,000 SXSWers, but her laughter and self-references and flirty-style of discussion just weren't working.  She seemed to enjoy talking about her relationship with Mark as an interviewer (or other?), more than asking him questions about Facebook or Platform or Beacon, or anything relevant to what the geeks in the audience wanted to hear about.

But it didn't stop there.

In the face of growing rumbled dissatisfaction from the crowd, Sarah continued to have a tough time asking mark a direct question, and ultimately ended up creating an adversarial relationship with the crowd that became palpably vicious.  At one point she exclaimed to the crowd "you don't know how hard my job is up here", and then complained "i'm trying ask interesting questions... you think you guys can do any better?"  After asking the audience to come ask their own questions, she even went as far as saying "if you guys think i suck so bad, why don't you send me an email?", to which the next questioner responded immediately "what's your email address?".  the crowd exploded with a roar that clearly indicated they were not Sarah's friends by any means.

At that point most of us were in complete and utter shock at what we were watching.  Several folks i know (like 7 or 8, not just 2 or 3) stated they had never seen anything like it, and that quite possibly it was the worst tech interview they'd ever seen.  NOTE: I'm not trying to attack Sarah here, and i wish this weren't the story... but it clearly was.  We all kept hoping it would get back on even footing, and it just never did.

In hindsight, we all wondered: WHAT THE HELL JUST HAPPENED?

well i might not have all the answers, but i think i know what went wrong...

The Problem: Sarah Lacy isn't a Geek.

Note to Brandee: Mark Zuckerberg is a geek.  He surrounds himself with geeks.  He feels comfortable with geeks.  He opens up & talks to geeks about stuff they have in common: technology, APIs, making cool shit that changes the world, and most important.... talking to other geeks. 

So if you want to put your CEO at ease & make him sound like a star, here's two suggestions:

1) Find an interviewer who lets him talk about tech, and how he's changing the world with it.

2) Find an interviewer who's ALSO a geek, and can at least relate to him on that level.

My guess is Mark will never turn into Steve Jobs, but i'm pretty sure he's one of the most brilliant geeks around, and that when you get him on a subject he's familiar with, and talking to someone he's comfortable with -- and not someone who's more interested in hitting on him -- he'll probably surprise us all with how eloquent he sounds. 

that is, as long as it's about stuff he wants to talk about.

and who know?  if you let him be who he is, and let him talk to someone who's more like him, maybe he might just turn into Bill Gates.  that guy's a geek too, but he seems like he turned out ok.

photo credits: Brian Solis, FutureWorksPR / Bubblicious

 

Need more diversity? like a bullet in the head.

Right now several people i respect a lot in the blogosphere  ask "do we have enough diversity at tech conferences?"... most of them meaning "do we have enough women speakers?"  In particular, the Future of Web Apps is being skewered for having only one woman at their recent London conf (and they were skewered last fall for having zero women at the SF conference).  Organizing a conference with 0 or 1 women speakers out of 20 is obviously going to subject you to a hell of a lot of criticism. 

However, i'm helping organize the upcoming Web 2.0 Expo conference and even only having ~15-20% women speakers puts us in the hot seat.  Does it matter that we actively sought out folks like Tara Hunt, Deb Schultz, Emily Chang and Kelly Goto to be part of our program committee?  that one of our co-chairs Jen Pahlka, has been reported to be female?  that Caterina Fake is on our advisory committee? that we have several notable female speakers like Kathy Sierra, Charlene Li, and Mena Trott presenting and moderating at our panels?

No probably not.  We still need to work hard to make sure we don't fall subject to all white male lineups (right now our primary keynoters are white boyz: Jeff Bezos, Eric Schmidt, and Jeff Weiner... Kathy is also doing a keynote, and we asked Caterina, still tbd).  Especially in the tech industry, that's easy to do.  Much as progress has been made in the last few years, there are still a distinct minority of tech geeks and entrepreneurs who are female.   Exceptions like Caterina, Joyce Park, Mary Hodder and others notwithstanding, we're likely only in the equivalent of the 50's or early 60's in terms of female geek emancipation.

That said, i think Brian Oberkirch hits it on the head when he notes diversity isn't just about having enough people with vaginas around (sorry my paraphrasing, not his... bitch at me, not him).  To wit: one of the critical issues we discussed early on putting together Web 2.0 Expo was to make sure we created tracks & sessions for people in marketing & community, user interface design, and business managers /entrepreneurs, rather than just being exclusively about programming & technology.  While we certainly made a point of having women involved in our planning, selection, speaking, and organizing process, we focused more on having OCCUPATIONAL DIVERSITY than gender diversity be at the crux of the conference.  Perhaps this was oversight on our part, but we wanted a diverse representation of PEOPLE coming from each of these disciplines, whether or not they're female. 

And yet, we still realize we were probably overlooking diversity of people from international geographies, diversity of age (both old and young)... both of these being significant demographics to include in the Web 2.0 conversation.  Not to mention we overlooked speakers who were blind (don't think we have any), speakers who were gay (didn't ask, won't tell), speakers who are evangelists (we have a lot of those, but i don't know their religion), speakers who are atheist or agnostic (don't know, don't care), or speakers who like latex and S&M (hey, we ARE having the conference in San Francisco).

So ultimately, what am i saying here?  Diversity doesn't matter?  It isn't a problem?  No & no.  Yes, it is something we should care about... specifically, we who are organizers should try harder to invite more women speakers at tech conferences.  However, on a scale from 1 to 10, is gender diversity at Web 2.0 conferences a high priority issue?  Imho, no it isn't.  There are a ton of other issues that people should be paying more attention to.  At best, i would say there's more concern around racial mix at tech conferences than gender.  But even there... why not spend your time worrying about gender equality in education or the workforce?  Or more significantly, gender equality around the world and in religion?  Sure tech conferences are one aspect of the problem, but i think you could spend your time on areas of society more obviously lacking... just ask Patsy Mink.

For a reference point on the scale of these issues, consider the tragedy of Zilla Huma Usman.  She was a Pakistani politician who fought for human rights / women's rights, recently assassinated by someone who thought she wasn't wearing the proper head covering... Zilla Huma Usman, the minister for social welfare in Punjab province and an ally of President Pervez Musharraf, was killed as she was about to deliver a speech to dozens of party activists, by a fanatic, who believed that she was dressed inappropriately and that women should not be involved in politics.

Now there's a challenge to diversity worth raising hell about. 

Ev sez: 10 rules for startups

10 great tips for startups from Ev Williams, founder of Odeo and Pyra Labs (aka Blogger, acquired by Google):

• #1: Be Narrow
• #2: Be Different
• #3: Be Casual
• #4: Be Picky
• #5: Be User-Centric
• #6: Be Self-Centered
• #7: Be Greedy
• #8: Be Tiny
• #9: Be Agile
• #10: Be Balanced

and an extra:

• #11 Be Wary

(here is a picture of Ev being wary ;)

straight up: Ev is really amazing being this honest & transparent with his business efforts.  i applaud anyone with so much humility who can give back to the entrepreneur community, and be so generous to let us learn from his mis-steps.  thanks ev, you rock :)

Don't Be Afraid... of Terrorists, or Leaders of the 'Free' World

Don't be afraid.  Don't watch the news.  Live your life to its fullest.

the show with zefrank

Forty & Fortunate

  go fly a kite 
  Originally uploaded by dmc500hats.

today i turned forty years old young.

some folks might get a bit depressed when they pass the ripe old age of four decades... but honestly i feel like i'm just hitting my stride of late :)

perhaps it's been the change of scenery for me in the past few months, doing some travel to Japan and the east coast, then coming back to the bay area & getting my hands dirty with several new ventures.  truly, i'm a fortunate soul -- i get to have the pleasure of working with several really cool new startups and some of the smartest folks in Silicon Valley.  a geek's delight!

i've also been able to spend time helping out some great non-profit organizations like Unitus, Full Circle Fund, and Kiva, as well as enjoy the company of all the wonderful people involved with those groups.

lastly, it's been magical to see my son Dante grow up before my very eyes in the past year & a half, and go from wide-eyed infant to very active toddler.  i can only imagine what next year will bring, as we have another little one on the way... talk about startups, yikes!

so altho i grow older, fatter, balder, and perhaps not any wiser, i must say i'm having a lot of fun enjoying my work, my play, and my family.  as i've noted before, it's tough to have a bad day in california when the sun is shining.

so step out, smile, throw a frisbee, go fly a kite... enjoy yourself, and smell those roses. 

(ps - apologies for being a bit senile & forgetful... those of you i've missed inviting over lately, i'm having a birthday party with some friends & family on sunday afternoon... drop on by & say hello :)

changes, oh

( please click on this musical interlude before reading post below - dmc)

you know what they say -- the more things change, the more Ziggy looks the same.  actually, i guess they don't really say that.

but i've always admired David Bowie's desire & ability to re-invent himself -- from glam rock in the late 60s/early 70s, to funky soul r&b in the later 70's, to pop superstar in the 80's and beyond.. including some work in film as well.  very few other artists (Madonna?, Miles Davis?) can stay both relevant & interesting while dramatically changing styles & growing older.

So i've had a little Space Oddity on my mind as i've decided recently to step down from a full-time VP role at SimplyHired.com, and become an advisor to the company.  The timing might seem a bit strange -- lately we've achieved some notable recognition, closed a significant round of funding, and lined up a very strategic media partner.  A lot of folks would look at the situation and say WTF dave?!?  you just spent a year-and-a-half busting your ass to make Simply Hired a 'Web 2.0' poster child (whatever that means), and now that you've finally arrived you're taking off?  are you clueless?

well, it's a label i've certainly earned before.  i've turned down jobs at Microsoft & Intel in the early 90's, overlooked great opportunities at Netscape & Yahoo in the late 90's, and barely managed to survive the dot-com depression by parachuting into PayPal in 2001 not long before they went public (my first day on the job was supposed to be 9/11... yikes).  i bought GOOG at $85, but sold at $180 (when they were only slightly ridiculously overvalued).  i'm usually way off on predicting other trends too: i sold my condo in SF in 2003 and became a renter, meanwhile i'm still waiting for bay area real estate prices to "tank" after they've gone up 3 straight years in a row.  still i like to think i'm not wrong, just early... um yeah.  perhaps a better objective assessment of me would be "often wrong, never in doubt".  just point me towards the next windmill, tally ho...

so be it -- i've never been a stranger to risk or contrarian thinking.  i'm sure i could be making a mistake leaving the [relative] stability of a funded startup with the wind at its back -- but in fact i'm hoping SimplyHired's future success (and my other angel investments) will help fund my next bout of startup insanity.  regardless i'm a free spirit again, and it's time to take a look around to see what else is happening in Act II of the Internet Revolution.  don't know whether i'm going to join something or start my own thing, but there's definitely a lot of brave new ideas floating around (and yes, i realize that includes a lot of silly / crappy new ideas getting funded too, but the rising tide of irrational VC exuberance floats many boats).

in the meantime i'm taking a few months off to relax & recharge the batteries, and reconnect with several new & old acquaintances to see what they're up to.  should also be a good opportunity to spend some time with the wife & kid (we celebrated our 10th anniversary this month, and Dante's 1st birthday yesterday), do a little extra work for  a few non-profits i support (Unitus, Full Circle Fund, SDForum), and read some books i've had sitting on the shelf way too long.  maybe even play a bit more Ultimate if the knee holds up.

on Monday i'm headed off to Tokyo with Saya & Dante to visit the in-laws for a few weeks, and enjoy a lot of sushi & miso soup.  look forward to catching up with everyone when i get back in middle / late May. watchout Ziggy... here i come!

Requiem for an Entrepreneur

I found out a good friend passed away a few days ago.  He was young; his death sudden.  I was sad to hear the news.

According to email from his family, Jad Duwaik died in Shenyang, China of an aneurysm on Jan 14, 2006 at 9:20pm.  His family will hold a funeral soon in Denver once he is home. 

For those who wish to find out more, his family can be reached @ [email protected], or at:

  The Duwaik/Hartley Family
  12476 E. Cedar Circle
  Aurora, CA  80012

update: Jad will be honored on Friday, January 27th at 9am
    Horan & McConaty
    3201 South Parker Road
    Aurora, CO  80014
    (303) 745-4418

update2: obituary for Jad Duwaik, SF Chronicle 02/19/06 (a guestbook is available for comments)

---

I met Jad in San Francisco back in 2000, just as the first Internet dot-com era was coming to a close.  At that time, Jad was organizing an entrepreneurial networking group called GreenHouseForStartups.  He had moved out to San Francisco in 1999, after the Denver ISP he had founded was acquired.  With his first win under his belt, Jad thought Silicon Valley would be the natural place for him to go next.  While many other entrepreneurs (like me) in the bay area shared Jad's sentiments & optimism, unfortunately for him (and us) the plug was just about to get pulled on round 1 of the Internet boom.  Still, we became fast friends and enjoyed sharing thoughts & conversations about the Next Big Idea and how we might get a new startup off the ground.

Jad spent a few years enduring the post-boom dot-com crash, and most of the money he'd earned from his first acquisition was put into 2-3 other ventures he hoped would turn into further successes.  Alas, it was not to be.  Times were tough in the valley, and Jad had no way of knowing the next boom was at least another 3-5 years off.  Jad did make a name for himself rather famously by authoring a piece called 'Diary of a Failure' that ran in the San Francisco Chronicle in late 2001.  With that he became a bit of a poster child for internet entrepreneurship, but i think he enjoyed the PR regardless.  Although the article was pretty depressing -- believe me, it was a depressing time for ALL of us who stayed here through it -- still, Jad struck me as optimistic by nature and i was sure he'd bounce back in the future.

In 2001, Jad decided to switch gears and go back east, to try and make it as a writer in New York (or teacher? apologies if i'm getting any of the facts wrong here... i'm sprinkling some links to his writing during the time that may have more accurate details).  He was in NYC when 9/11 occurred, and he wrote about that experience.  For a short time he also thought about going to the Middle East to learn more about the challenges taking place there, but after thinking about it for awhile decided to stay in NY and became a math teacher. 

Then in 2003, Jad got the itch to travel and see more of the world.  Ever the entrepreneur, he decided China was the next big wave of opportunity, and so he moved to Liaoning to teach English.  He also started writing a regular newsletter on his experiences in China which i found fascinating.  it was interesting to hear about his interaction with a new culture, and his efforts to learn Chinese (language, culture, people). i occasionally would IM jad late at night and catchup with him.  one time i helped another friend of his in China do some AdWords buys, to help drive traffic to a tourism site for the city he was staying in.  he wrote some great stories and poems about the Chinese, and about color and women.  i think he was really starting to get into the flow of China.  i hope so, i really would like to think he was full of optimism again before he passed on.

I don't know if this short story captures the flavor of Jad, but i thought it important to write down what i remember.  He was a good friend and a thoughtful person.  He had wonderful ideas -- though some a bit far-fetched, but that's an entrepreneur for you.  His creativity and writing were a joy, and they made me laugh, made me think.  It's sad he passed on so young, because he had so much still to offer the world.  But i hope he enjoyed as much of it as he could, and i know we all enjoyed Jad and our time with him.

So here's to Jad, aka TJ, aka TokyoJad -- my friend, fellow entrepreneur, cherished traveling companion on the road ahead. 

Peace be with you my friend.

- Dave McClure
  Redwood City, California
  January 20, 2006