Russian Spy’s Connections to Silicon Valley

UPDATE: Anna Chapman’s (one of the Russian Spies taken into custody) Facebook profile has gone private. Pictures and Friends information is no longer publicly available as of Wednesday evening (6/30/2010).

Earlier today, I looked up the Facebook URL for Russia’s hottest spy. I was actually pretty surprised her profile was still up and available… you know given that she was being held by the authorities, probably in some cell in Guantanamo.

So, curious as I am, I started digging around her default public profile. I saw that she had 168 friends. I started digging further.

Her friends seemed to be virtually all men… 83% to be exact. I then started looking at the profiles of some of these friends she had. After only a few clicks, I found that some of her friends had shared friends with me. My attention instantly perked up as I realized that I am 3 degrees of separation away from the Russian spy… or put another way, many of my friends have the same friends as the Russian spy. Okay, kind of quirky and fun for a Wednesday morning.

Now for those of you who don’t know me, I am a tech entrepreneur and investor in Silicon Valley. Having some success on both fronts has afforded me the opportunity to friend up with a bunch of the movers and shakers in Silicon Valley, Internet entrepreneurs and investors alike. So things started to get interesting as I deployed some sorcery to run through all 168 of Anna Chapman’s friends and determine if we shared mutual friendships.

The Analysis

Here’s where the analysis took me:
– The Russian Spy has mutual friendships with 32 (or 6%) of my friends
(or put another way: 32 of my friends know at least one of the Russians Spy’s friends)
– 12 (or 7%) of the Russian Spy’s friends directly know my friends
– 4 (~1%) of my friends directly know several of the Russian Spy’s friends

The Low Down – naming names

Here’s a list of my FB friends who share friends with the Russian Spy:
– Jimmy Wales – Founder, Wikipedia
– Robert Scoble – Founder, Building 43
– Om Malik – Founder, GigaOm
– Matt Marshall – CEO, VentureBeat
– Loic Lemeur – Founder, CEO Seesmic
– Dave Mcclure – Angel Investor
– Philip Kaplan – Co-founder, Blippy
– David Weekly* – Founder, PBWorks
– Larry Lessig – Board Member EFF, Creative Commons
– Naval Ravikant* – Serial Entrepreneur
– Raj Kapoor – Partner, Mayfield Fund
– David Lee – Partner, SV Angels
– Ed Baker – Founder, CEO
– Paul Bragiel – Founder, CEO of Lefora
– Noah Kagan – Co-founder Gambit
– Kamal Ravikant* – Angel Investor
– Patricia Lassus – Entrepreneur
– Ryan Junee* – Entrepreneur
– Sylvia Battilana – Co-founder, Auctionomics
– Tammy Camp – CEO, ComCorp
– Matt Mireles – Founder, CEO, SpeakerText
– Ben Mendelsohn – President, Interactive Television Alliance
– Beatrice Pang – Founder, Mokini
– Shaukat Shamin – Co-founder Permuto
– Carl Bressler – Investor, Advisor
– Grant Wernick – Entrepreneur
– Erin Turner – Founder, CEO Crave
– Babak Nivi – Co-founder Venturehacks
– Daniel Brusilovsky – Entrepreneur
– Jared Kopf – CEO, Homerun
– Gerd Leonard – CEO of the Futures Agency
– David King – Founder GreenPatch

Disclaimer: All information provided above was publicly available as of Wednesday morning (6/30/2010). If anybody wants me to take their information out I will, but as I don’t believe there is anything personally embarrassing or inherently private, I figured there was no harm in providing this data.
* denotes individual that has multiple friends in common with the Russian Spy


– I was initially surprised by the number of connections the Russian Spy has into the movers and shakers of Silicon Valley. A deeper look paints a bit more textured story. Basically Anna has (/had 😉 ) a handful of friends that are in the periphery of the Russian and American tech scenes. I wouldn’t say that she was a regular in the scene but rather was friends with people who are. Given the sheer number of just my friends the Russian Spy shares connections with, I’m gonna guess that she had several run-ins with a number of top-level Silicon Valley entrepreneurs and executives, and who knows how many of them she may have connected with. Maybe getting the next degree out into the tech world was part of her orders from the Kremlin.. maybe I or my friends would have connected with her at a tech party in the next 6 months… who knows.. 🙂

– What this whole exercise made clear to me is the extent of deep investigative insights that sit just a few keystrokes away for a criminal or civil investigator. I personally haven’t seen any pitches for companies that sell sophisticated social networking investigative tools to law enforcement, but if they don’t exist, they most certainly will. Maybe I should start or fund one!

– I’ve always been a fan of transparency, and have theorized that the ultra-transparency that social networking tools provide will keep everyone a lot more honest. Criminals and Spies are going to have a very difficult time being engaged members of society without being completely vulnerable and exposed through the tools that being socially engaged require.

– Trust is an interesting thing when extended online. Trusting friends with information often means that your information goes to their friends including sexy Russian spies. And then everything is so public on social networks today and your information is available to any investigative hack (like me) or actual investigator. I just did the equivalent of 3-6 months of investigative work 20 years ago, in about an hour. This is a new world for sure.

– What a fascinating and fun analysis for me to do. I mean, when I was a kid I always wanted to be a spy. The public data gave me the opportunity to do counter-intel on a suspected Russian operative, all from the comforts of my home office!! That’s SERIOUSLY COOL!

Attention Ning Engineers: Less Suck – More RADOOL!

This note is for the uniquely creative, astonishingly productive, remarkably intelligent, extraordinarily adventurous, unnaturally constrained-by-the-bloated-company-mentality Ning engineer…

My INSANELY AWESOME portfolio companies are HIRING!!

Here are my portfolio companies:

Hit me up – @konatbone !!

Have fun at your pink slip party tonight…and let’s rap about working at a killer startup tomorrow…or the next day 😉

The Whole Truth and Nothing But the Truth, So Help Your Reputation

Over the weekend, Mike Arrington put up an interesting op-ed on the state of the reputation on the Internet — and Techcrunch then followed up with a fairly negative review of a site ( that just launched. The gist of the posts is that these sites will primarily become scaleable defamation platforms, and if Arrington is right, we all need to hope that society learns to disregard indiscretions.

Surely, on today’s Internet, we’re all potential victims of some “wingnut” saying something horrible about us, or some random picture of some indiscretion making it to the Internet and ruining our careers. The problem is that any and all information that ever existed is making it to the Net. Compounding the problem is the existence of the real-time web, its exploding communities of people sharing all of their thoughts and uploading content at will. What we’re quickly finding is that in some regards the Internet acts as a cesspool of information where lies and libel can ruin people’s reputation. And even with regards to legitimate, accurate content about people or entities, the Net is becoming too noisy for the crisp signal that we’re actually looking to get from it.

But what happens when an accurate, high signal-to-noise reputation system for people rolls out? A service designed to take in all the public information about a person, encourage reviews of that person, sift through and moderate each profile toward the most accurate picture of that person (including progressive moderation that has a slight lean toward empathy of the reviewed). The value could be huge. HR departments already check criminal history before hiring, but what if they could get an accurate picture of someone’s reputation in the workplace? What if, before you did a meeting with someone you didn’t know, you had a tool that went far beyond a simple Google search, and had lengthy reviews of that person across all his colleagues, partners, bosses, employees? You knew his weaknesses and strengths, and what to watch out for in a partnership with him.

What would happen is that this hypothetical site would take off. The value it provides its users would be huge, and it would quickly become a *necessary* tool for professionals. But it would only be valuable as long as it can do a great job of providing *accurate* information and reputation scoring. Why? Because a reputation site that has a bad reputation itself is worthless. What long-term value is a site which has a reputation of being an information cesspool?  It gets old, becomes a lame gossip site, and I move on (like the unmoderated financial/stock commenting sites).

Now some of us may hate that all of this information gets out there, that all of these reviews are so easily created, that we are so exposed to the public… that cheating on a wife, or a business colleague no longer can happen in the dark, but hyper-transparency is the world we are increasingly living in and we all better get used to it.  The silver lining is that services pedaling hate, libel, and gossip will be marginalized as forms of entertainment if they’re lucky or will whither altogether. There is simply too much value (and revenue oppty) in accurate reputations for the inaccurate ones to keep up.

The sites/services/platforms in this category that win are those that turn the real-time noise into something valuable.  The services that can provide the most accurate view for the consumers of the reviews–along with some level of empathy and recourse for the reviewed–will win.  All data will be out there, and truth shall ultimately win, because truth is so much more valuable than falsehoods.  Add to that a comfortable place for the reviewed to interject “their side of the story”, and the service becomes the trustworthy truth and accountability platform.

So what about Arrington who says reputation is dead, and that society will change to accept indiscretions? I think what Arrington was really saying was that managing reputation by omission of facts is dead. But I think that reputation is anything but dead, and instead will become more important than ever. With more data and info getting on the net, and as the tools to decipher fact from fiction get better, reputation becomes more accurate, and significantly more valuable. We can, fortunately, breathe a sigh of relief that value is in fact and not in fiction; that hating, and libel and lies get pushed out b/c of their relative paucity of value. But we are fooling ourselves into thinking that indiscretions will be completely forgotten–the best case is that the most common indiscretions get pushed off the indiscretion list. Its just that those of us that are adults right now are carrying an old belief that what happens in the past stays there. That’s a luxury that is about to die and we all better get used to it.

The Killer, Killer Marketing Job

When I invest in a company, I’ll usually get involved in the company well beyond the typical angel investor. So, when Dan Rodrigues, the founder & CEO of Kareo asked me to help bring some thunder to Kareo’s recruiting efforts for an insanely strategic marketing position, I jumped at the chance to step up my recruiting game. We’ve still got to find the Killer Marketer to fill the Killer Marketing Job, but my guess is the job post we came up with below is one of the more creative and progressive you’ll see. What do you think?

[Note: special shoutout to David Barrett, founder/CEO of Expensify for continuing innovations in the creative job post arena].

Killer Job for a Marketing Killer
Profitable, healthcare IT startup looking for a modern day marketing warrior!

Hello candidate. Let us first introduce ourselves. We are Kareo ( and we’re based in Irvine, California. We build the Healthcare cloud services that power the offices of thousands of small physician practices throughout the U.S. We help doctors get PAID by transforming the complexity of today’s healthcare system to make it simple. Scheduling, billing, and practice management? Check. Electronic connections to thousands of insurance companies? Check. Integrated electronic medical records? Check. The list goes on. Basically, Kareo is at the center of the storm, which is at the center of Obama’s policy agenda and the national debate. Healthcare. A $2.4 TRILLION (yes, that’s with a “T”) industry, representing 17% of the U.S. GDP. Technology is coming to transform and revolutionize this industry and Kareo is positioned to carry the torch for 60% of the approximately 900,000 physicians in the U.S. who practice in small medical offices.

That’s the high level. The details go like this… Kareo, founded in 2005, has finally reached profitability and cash flow positive! We’ve done this through a fierce focus on our customer acquisition funnel, complete dedication to our customers, and disciplined belt-tightening to make ends meet. But now we’re generating cash flow, and that means it’s time to vastly expand our marketing efforts. Running those marketing efforts is the marketing warrior’s job to take. You might call this position a Director of Marketing, but that doesn’t quite do it justice. We’re looking for The Marketing Killer! Based on your experience, we’re budgeting for an annual salary of $120,000- $150,000, and you’ll be entitled to benefits and stock options.. Here’s what the position looks like:

SEM/SEO and customer acquisition basics still apply. Doing them better, smarter, and integrating them with a more creative and expansive marketing effort is where we’re going. Expanding the funnel and tightening acquisition – making lead conversion do things we thought weren’t possible. Turning our industry leading customer satisfaction into a powerful “word-of-mouth” customer referral program and channel will give us leverage. Digging in and doing outreach into the social media realm, becoming visible in the blogosphere, and experimenting with a presence in real-time streams are all part of our agenda. Lighting up our inbound leads with savvy, coordinated email and direct mail campaigns. Refining and polishing our marketing collateral. Turning our under-the-radar media presence into a top-of-mind healthcare industry narrative, inserting us into the national healthcare debate and positioning Kareo as the Healthcare IT pioneer to watch.

This is a strategic position for Kareo… but that doesn’t mean you’re not rolling up your sleeves. Yes, we are embarking on a substantial growth ramp in terms of revenues and in people, but we are still a small startup. That means that you’re growing with us. We want the go-getter, hard working, creative problem solver. You’re as analytical as they come and have actually dreampt of Excel spreadsheets at least once. You bring that data driven decision-making with an experimental and tinkering approach to your work. You iterate constantly, making the funnel bigger and badder and are full of glee when you get the A/B test results back. But you also have a creative side. You know how to motivate and inspire the prospective customer. You work with creative types to make Kareo’s vision a reality. You have an entrepreneurial, empowered mindset, and expect to be accountable, and expect the rewards that come with it. You bring energy to your work and your optimism and enthusiasm are infectious.

This killer job is here for the taking but here’s what it’s going to take from you:
• Provide a link to your LinkedIn profile with an email address (let’s face it, resumes are dead).
• Answer the short-form and essay questions below (this shows us you’re serious).
It’s a lot to ask so what will we do in return? If you complete the application, we guarantee that our CEO will review your application and respond to you directly within 5 days or less.

Killer marketers need-only apply. What are you waiting for? We look forward to hearing from you.

Kareo Killer Marketer Questionnaire

1. How would you rate Kareo’s current SEM and SEO efforts? What might you change or experiment with to improve the performance of our search engine marketing?

2. What’s the single, most important factor in successfully converting online prospects into paying customers? Why? What’s the most overlooked high-impact variable in converting online prospects into paying customers?

3. What is the best way to leverage social media and the blogosphere in order to enhance sales of a small business product? Where does traditional PR fit into this picture?

4. Name a product for the small business market whose marketing you most admire. What do you think is the secret to their marketing success?

5. How do you manage your professional ‘Inbox’? How do you schedule your time at work? What are your secrets for staying productive?

For consideration, please email your LinkedIn profile and questionnaire answers to

CouchSurfing for the TechCrunch50

Attention all TechCrunch 50 out-of-town Attendees!! The JamPad will be providing free couch-surfing to two (2) TechCrunch50 2009 entrepreneurs during the TC50 rehearsals and the main event. Making your company a success is all about being scrappy. Paying for hotels can crush your cash flow so couch-surfing is the only way to go. The JamPad is the ultimate way to couch-hop in luxury & style and in a creative, entrepreneurial atmosphere. Here’s the FAQ on how to get your free lodging.

Q: What is the JamPad?
A: The JamPad is my San Francisco home. It is a place where entrepreneurs regularly come to hang out, to rap on ideas, to jam with other entrepreneurs, to play Wii Tennis and Gears of War, and to have fantastic healthy gourmet meals made by the JamPad’s in-house chef. Normal open hours for the JamPad are from 10AM to 2AM. We also do BBQ’s, grill seshes, art & wine events, networked Armagetron competitions, coding seshes, you name it.

Q: Did you say FREE LODGING?
A: Yes! For a limited time, the JamPad will be offering free lodging to entrepreneurs in need during the TC50 rehearsals and main event. Planned availability includes: September 1st-3rd, and September 9th-15th (some flexibility around dates). There are two rooms available, rollout in home office and a 2nd master bedroom. High-end accommodations include generous living space, backyard for BBQ, hiking, tennis court, basketball court, amazing views of the city. Meals will be provided for you, with a focus on healthy, tasty cuisine (as well as the occasional pizza delivery and Trader Joe’s meal ;). Entrepreneurial advice and coaching on your TC50 pitch is also available if you so desire (though not a required activity of your stay). Expect many silicon valley entrepreneurs to come in and out during the days and evenings.

Q: Who exactly qualifies for the JamPad FREE LODGING?
A: Qualified applicants must be legitimate founders of any TC50 2009 demopit or presenting company.

Q: Is this first-come-first-served?
Absolutely not! The JamPad is my house for God’s sake. There will be a brief vetting interview in order to determine who we award the FREE LODGING to. Best chances are to those who 1) have a GREAT idea 2) are generally optimistic, hard-core entrepreneurs, 3) bring a lot of passion and creativity to their work and their life, 4) are fun to hang and have a beer with, and 5) do not have serious legal troubles (bad credit scores excluded ;))

Q: And who exactly are you?
My name is Travis Kalanick. Here’s my crunchbase page. I have been a pretty hard core entrepreneur, and definitely one of the scrappiest. In everything I do, especially my companies, I’m all about creativity, passion, perseverance, and fun. My last company worked out and now I advise and invest in the most amazing companies and entrepreneurs out there. The JamPad is my way to give back to my fellow scrappy soon-to-be-successful entrepreneurs and have a blast while I’m doing it.

Q: Who can vouch for the JamPad?
Many tech entrepreneurs can vouch for the JamPad prowess. Here are just a few friends who’ve recently spent time at the JamPad:

  • Aaron Levie, Founder, CEO, “Travis’s full range of sleeping and hygienic amenities offer a winning combo for any sleep-deprived, smelly, starving, delusional, stressed, or money-less guest. If you happen to fit into four or more of those categories, you’ll likely be treated to a gourmet breakfast and be waited on by his Live-in Harvard Ph.D girlfriend”
  • Angelo Sotira, CEO/Founder, Deviantart: “When I visit San Francisco, the JamPad is the place I want to stay. Being central to most of my meetings is a nice advantage, but the bar is set spectacularly high by the hosts of JamPad; tbone and dolce diablo. Come experience the madness, the fast wifi, the comfort and style of the place, the excellent discussions ranging from technology to technology; but *mostly* the variety of cheeses in the fridge, err!!!”
  • Paul Bragiel, CEO/Founder, Lefora: “The JamPad… if you’re looking to live the life of a struggling musician, sleep on the floor of a random fan, and be surrounded by cockroaches, then you’re in the wrong place. If you’re looking to for an awesome place to crash in comfort and meet super connected entrepreneurs, then you’re in the right place. Might even be treated to a bottle or two of homemade wine that we’re letting age as we speak”

  • David Barrett, Founder, CEO Expensify:
    “Travis has a mean BBQ and the biggest couch in San Francisco — no joke you’ll be couchsurfing on a longboard for sure. He’ll also destroy you in Wii Tennis if given the chance.”

  • Janina Gavankar, Actor, Ms. Dewey in her spare time: “I love being a fly on the wall for Travis’s JamPad sessions… the insane geek creativity makes me want move to San Francisco, to the extra master bedroom of the JamPad of course.”
  • Gary Vaynerchuk, founder, Vayner Media: “I have never seen a place that has such a bad ass vibe…and it has nothing to do with Travis!”

Q: How do I apply?
Send an email to or @reply me on twitter. If the applicants come in as I expect, we’ll be locking down lodging pretty quickly, so hit me up ASAP.

Good luck and see you soon…

Why Schwarzenegger is right

A couple of weeks ago, I jumped into the fray of an online debate (on the PHO list/) about how California should deal with its looming bankruptcy. The debate essentially broke into two camps a) tax and spend and b) no new taxes, less spending. It would likely be too “taxing” to have the dissertation on the merits of the two camps, but I figured I would take a look at the hard numbers to determine which side has the better argument.

The numbers weren’t pretty. CA has some of the highest tax rates in the country. With those high tax rates you’d think there would be fairly high quality services provided by the state. Unfortunately, those huge taxes provide services that have the lowest levels of quality in the country. To make matters worse, it turns out that of the 30mm CA citizens, the state depends on 140k affluent people to pay 50% of the tax burden.

The bottom line is that the state is so inefficient at spending its tax dollars, and its politicians and bureaucrats so unaccountable for their corrupt spending practices that I believe spending cuts are the only way to restructure our insolvent state. Below is all the juicy data in the email I sent to the email list (7/12/09):

CA taxes its citizens more than virtually all other states, and then provides services at quality levels ranked at or near the bottom compared to all other states. The facts show that CA citizens are getting a *very* bad deal economically speaking. None of the stats I provide below are surprising to most folks except as to how they illustrate how extraordinarily bad the state is run compared to other states in the U.S.

Tax stats on a per capita basis (unless otherwise noted):
– CA’s state/local tax burden ranks 6th highest in the nation
– CA business tax environment ranks 48th lowest nationally
– CA top individual tax rate ranks #1
– CA corporate income tax highest in west, #9 in the U.S.
– CA property tax collections are in the middle of the pack, 19th highest nationally (avg. $$ per household, 28th on per capita basis)
– CA sales tax rate of 8.25% (2006) is highest in the country


Summary: CA citizens carry some of the highest tax burdens in the U.S. on almost every tax category you can come up with. Even on the property tax issue, CA ranks middle of the pack at #19.

Now let’s look at the quality of services:
– Quality of Healthcare: CA ranks 50th in quality of healthcare provided (and 39th overall if you include factors other than quality)
– Quality of Education: CA ranks 42nd in reading and math scores by 4th and 8th grade students
– Violent Crime per capita: CA ranks 14th highest in violent crime rates

Healthcare stats from:
Education stats from:
Crime stats from:

Twittergate: Don’t Believe the Hate

Okay, before we get started, here’s the catch-up on Twittergate for those of you who aren’t up on the 24-hour tech news cycle:

  1. A hacker broke into Twitter-owned file stores and copied hundreds of documents
  2. Techcrunch received these hundreds of confidential Twitter documents as did several other individuals.
  3. Michael Arrington, founder of techcrunch, is posting a limited amount of the information he received.
  4. In true blogging style, Arrington has openly discussed the ethical dilemma he is faced with in real-time, something you rarely if ever see from the mainstream press. Arrington is talking about not just what was in those documents, but also being very transparent about how he got those materials

So what happened next? Some serious hating on Arrington ensued which got me to thinking about this entire event.

So here are my main contentions on the matter:

  1. The main action Arrington took that was different than how most other journalists would handle this was that he was transparent about how he got the information.
  2. If you have a serious problem with what Arrington did in this case, then you have a general problem with the institution of news in the United States.
  3. There is a very good argument that what Arrington did in this case was at least as ethical if not more so than how stolen Trade Secrets are normally handled by journalists

And instead of a full treatise attempting to prove those arguments, I figured a little Q and A might actually be more effective. Fire away in the comments section to debate the points!

Skeptic Q: A crime was committed to get Arrington the information. Doesn’t that make Arrington a dealer in stolen goods?

Swoosher A:

  • Yes, Arrington was dealing in stolen goods. But Arrington’s actions have broad 1st amendment protection:
  • Most journalists do this regularly, they are just not so transparent about it. Even this morning’s news about the latest termsheet from Microsoft and Yahoo! discussions is quite possibly the dissemination of material that qualifies as a trade secret. I could come up with 100 examples here. I recommend you scan the headlines of the Business Press on any given day to find a few.
  • The uproar over this in many ways is that people got a very inside, very candid, dirty look at how the sausage is made. It makes people feel uncomfortable to see that–like going to a slaughterhouse– but overall it’s a very good thing for folks to have their heads abruptly removed from the sand. The part that is regrettable is that in Arrington’s candor, he became the object of the abhorrence with the sausage making

Skeptic Q: Isn’t there something different about a leak of Trade Secrets vs. a hacker stealing them?

Swoosher A:

  • It’s the difference between an “inside job” and an “outside job”
  • The hacker committed two crimes (hacking, and theft of Trade Secrets), where as the insider committed one (theft of Trade Secrets).
  • In either case, the journalist (in this case Arrington) is generally protected to publish what comes into his or her inbox.
  • Is it okay that theft happens from insiders, but somehow worse when it happens through outsiders?
  • Bad analogy: If there was a diamond heist committed by insiders at a jewelry store vs. a straight out robbery, should the insiders get a pass? Sure, maybe the outsiders used force to get the gems, which means they also may have committed an additional crime, but a heist is a heist.

Skeptic Q: Just because other journalists do it doesn’t make it right…

Swoosher A:

  • Totally fair Argument
  • The news business is FOR PROFIT. It’s in their interests to publish news that draws an audience and makes them money. It is also highly competitive. If someone else draws your audience tomorrow, you’re out of business.
  • This has caused an environment that sacrifices some notions of ethics to stay in business.
  • My main contention is that though not necessarily right by the strictest moral code, but theft has fueled the news machine for hundreds of years. Theft of trade secrets is common, and sometimes (though not in this case) the journalist is involved in even “conspiring” with the thief… i.e. “I’m going to need more to run the story… do you have a document that says XYZ?”
  • The problem is a completely free press though it has many benefits to society, can ultimately encourage crimes to be committed. We see such crimes regularly committed for the purpose of disseminating to the media all of the time.
  • I’m certainly open to how to change the system. Where to draw the line is a very difficult task

Skeptic Q: I can understand if there was some misconduct or moral imperative being looked into, but in this case there was none. Shouldn’t that effect the ethical conclusions about this case?

Swoosher A


  • The moral imperative question is easy. If there was serious moral import in this case, there would be no question at all. If Twitter was committing fraud, or stealing diamonds from banks to fund their business, I don’t think there would be a single complaint about Techcrunch’s actions.
  • The real question is that in cases *without* moral imperative, should journalists continue trading in stolen information that has little to none moral import?
    • News business is competitive
    • To stay in business they must break stories
    • Everybody trades in stolen property in order to continue breaking relevant stories in order to stay in business.
    • Is the journalist at fault for wanting to keep his job which requires dealing in stolen property?

Skeptic Q: I still feel that Arrington was more wrong than the average journalist

Swoosher A:

  • Arrington brought an extreme amount of openness to the party that was unnerving for people who do not understand how the news system works, or disturbing for people who are not used to that kind of openness. He showed us how the sausage is made, and it definitely ain’t pretty, and makes a lot of us feel uncomfortable.
  • Arrington was blogging real-time as his Inbox was filling up. The emotion of a hungry hard core news person comes through in that first post. Not everybody is comfortable with that. And that’s where Arrington’s lightning rod style comes in. Even with the facts on his side, his style isn’t elegant and can certainly rub some people the wrong way. But it doesn’t change the facts, and it doesn’t make him morally wrong as many detractors like to claim.

Skeptic Q: How the heck was Arrington in this case as ethical or *more* ethical in his handling of Trade Secrets in this case than the average one

Swoosher A


  • He was fully transparent about how he got the information. This is atypical in the business. In fact, if Arrington had not been this transparent, simply stating that an anonymous source had provided the document, there would have been ZERO uproar about this matter. Most news organizations like to stay out of the story itself, and generally like to keep the spotlight off of how they get their materials. The typical news outlet would have debated this in the newsroom but left the debate there.. AND they certainly would not take it into the public.
  • It can be argued that journalists dealing with their sources of trade secrets are halfway conspiring with the leaker to get those documents. This activity is shady at best, and criminal at worst (without 1st amendment protection), but is rarely prosecuted or enforced. Arrington simply opened his email box in this particular case.

Spinning the Globe

As many of you know I’m a pretty prolific travel and adventure junkie, especially since leaving Akamai late last year. In less than 12 months I’ve made it to Spain, Japan, Greece, Iceland, Greenland, Hawaii (twice), France (twice), Obama Inauguration, Australia, Portugal, Cape Verde, Senegal. Good times, great friends, epic adventures.

One of the most interesting trips is an annual pilgrimage I make with The Random Travelers Society. The Random Travelers Society is a 3 year old organization made up of 12 technology entrepreneurs from around the world who love adventure travel. Here’s the big idea:

Location Selection

At each year’s destination, one of the members throws up an inflatable globe. Another member catches the globe, and yet another, with his eyes closed, points on the globe with a marker.

Wherever that marker lands, we go to the nearest point of civilization that has a pub or bar. So far we’ve gone to the Chatham Islands, New Zealand, Tasiilak, Greenland, Antarctica, and Sal, Cape Verde. Next year’s locale: Mar Del Plata, Argentina.

The location selection algorithm above is biased toward unpopulated areas in general, and strongly tilted toward isolated, unpopulated islands. Think about it: densely populated areas take up a very small land area on the globe (as opposed to non-densely populated areas) and any water landing – water making up 70% of the earth’s surface—will go to the nearest land mass—i.e., an island.

Finding a date

Finding a date has to happen early. We try to lock in a date a year in advance so that we don’t have crazy conflicts with the 12 society members to coordinate. We basically look at weather, events going on locally, members’ availability, etc.

Staging Location

When you’re going to far flung places around the globe, there is typically 1 or 2 cities that are suitable “jump-off” points. We call them staging locations, and we usually spend a few days to a week at a staging location. Staging points can be great to get to know the region better, and can also be a great half-way-house as you go in and out of some far-off remote location. For our most recent trip to Cape Verde, we had two staging locations: Lisbon, Portugal, and Dakar, Senegal. I met up with fellow RTS member Paul Bragiel in Lisbon beforehand and closed out the trip with a group of RTS’ers in Dakar, Senegal after the main event in Cape Verde. Lisbon was a great last piece of civilization on our way in, and Dakar greatly enriched the trip as it allowed us to dive deeper into Africa on our way out. Last year we all went to Reykjavik, Iceland before wandering off into the wilderness of Tasiilaq, Greenland

So, you go to a crazy random locale… AND??

The purpose of RTS is to visit truly random locations.. locations that are likely on NOBODY’s must-go-to-list. But once we get there, we look to connect with high profile local dignitaries, entrepreneurs, professors, artists and the like. Yes, this is a vacation, but it is also a cultural and entrepreneurial exchange of sorts.

The idea is that from the moment you hit the ground (even in the staging areas), you want to dive into the region’s culture, its business community and its education and government leadership. What better way than this to meet really interesting locals and dive into the local scene? Doing this right takes SERIOUS prep work (a HUGE shout out to Paul who is an international business networking PHENOM)

  • You’ve got to dig deep into LinkedIn for your connections in a region
  • Google searching to find out who’s who in that country.
  • Prolific email networking and follow-up
  • SNAIL MAIL. Yes, get your envelopes and stamps out. A personal letter to your ambassador or a business leader can make a huge difference. And once you’ve got them in the loop, use their know how to help you spread further.

Ultimately, you should have a dinner scheduled for every evening you’re in town. Here’s a list of a few of the amazing folks we met up with (i.e. lots of drinks and dinners) on our West African trip:

  • U.S. Ambassador to Portugal
  • U.S. Ambassador to Cape Verde
  • Foreign Minister of Cape Verde
  • Former Communications Secretary of Cape Verde
  • Spoke to professors and students at Praia University
  • Several famous Cape Verdean artists & musicians
  • Managing Director of Senegal’s largest bank

Adventures Galore & Turning the dial up

At the end of the day RTS is about travel adventures with other like-minded people, in our case technology entrepreneurs. We make sure to take some down time and hang out, talking shop, jamming on new ideas and life. But at the end of the day we’re constantly looking out for adventurous times. We like to ask ourselves the question, “How do we turn the dial up?” The answer has ranged from creating a flashmob Reykjavik house party to attending an inspiring music concert with diplomats and dignitaries in Cape Verde’s congressional hall, to virtual anarchy on the street markets of Dakar (and a whole lot in between).

For me RTS has been about making the Flat World my world, and living life as an experience. The more stories I come home with, the better the trip. And taking a week or two a year to change your environment in an extreme way to see the world differently… that’s living. The great thing is anybody can create their own Random Traveler’s Society. Giddy up!! Get your globes out. We’ll see you in Argentina next year! 🙂

African Tricks & Myths

As many of my Twitter followers know, I made it out to West Africa at the beginning of June and just returned last week. I spent most of my time in Cape Verde and Senegal and loved every minute of it. While there I met with diplomats (including 2 U.S. Ambassadors), dozens of entrepreneurs, spoke at a university and saw the sites. Not a bad way to go (definitely have to come up with some goal for number of U.S. ambassadors I can have a drink and fist bump with). Below are some fun anecdotes and tips from the lighter side of my West Africa travels.

#1 Fist Bump Origination

No matter what Wikipedia says, the fist bump DID NOT originate in the United States. EVERYBODY in West Africa does the fist bump, from casual gatherings to business functions. They even do a Sammy Sosa-like bash to the chest/heart after bashing with their “brother” (brother is used generally to describe a friend or someone you are aligned with in some way). The stylish West African fist-bump is WAY too widespread and natural for this to have been brought from the just-getting-on-board-the-fist-bump-wagon-U.S.A. I’ll make sure to forward this to Michael Arrington as Africa may be a good place for him to do *ALL* of his business meetings.

#2 Fittest City in the World

Every day in Dakar, at about 5pm the rush hour starts, and it doesn’t end until about 8pm. But this is not your typical car-induced traffic jam. Dakar sits along the coast and has its own Pacific Coast Highway. The difference w/ this traffic jam is that during rush hour there are more people along the side of that highway than cars in some stretches. This 20 mile long crowd isn’t leisurely walking home from work. They aren’t even briskly walking to do their daily grocery shopping. No, this group looks like they just jumped out of a Nike ad in their workout gear and their insanely toned ripped bodies and are all getting in their daily jog in 90-100 degree heat. I’d estimate that there are 10’s of thousands of runners along the highway on any given afternoon. Along some stretches on the beach, you’ll see a mass of maybe 500-1000 runners tightly huddled together running in unison. Also dotted along Dakar’s coastline are mini-gyms with simple equipment on the side of the highway. It’s normal to see pushup/pullup contests, bench press & weights (they use tires instead of iron plates). I’m not sure if researchers include Dakar in their surveys of fittest cities in the world, but I am 100% positive Dakar wins against all comers.

#3 Surfing is epic

Why doesn’t anybody talk about Africa surf? It’s all there. For the kitesurfers and windsurfers, there are steady wind havens all over the place. I personally spent my time at a windsurfing world tour site in Cabo Verde (aka Cape Verde) about 300 miles off of the west coast of Africa. The weather is some of the most consistent you’ll see anywhere. As it sits off of the Saharan coast, it has Saharan desert characteristics with archipelago ocean moderation. Cabo Verde brings consistent year-round temperatures at 80-85 F with low humidity. In fact, one of the locals told me they had seen it rain only a couple times in the last 2-3 years. Beautiful waves that range from the tame 3 footer to the much larger. And of course the host of a Surf World Championship Event at Ponto Preta (pics here. Can you say year-round surf-athon??

#4 Marketplace madness

Do we have any garage sale aficionados (umm @garyvee where you at)? Any flea market fans? Any gnarly negotiation fiends? You’re not going to like what I’m about to say, but you all definitely need to hear it. You are all AMATEURS. Can you be an All-American basketball player if you’ve never been to March Madness? Can you call yourself a real pro-golfer if you’ve only seen the Master’s on TV? The answer is a resounding ‘NO’ and that’s why all you street market fiends are still in the bush leagues. Because, as far as I can tell, Dakar is the Mecca of Street Market Madness and if you haven’t been there, well… you just need to. I’ll provide you with a couple anecdotes in case you make the pilgrimage:

Boo-Boo Extravaganza (warning: not for the timid or faint of heart)—When you first arrive at the downtown street market (ideally with a few travel buddies—i.e. more fresh meat for the vendors), walk down one of the streets and loudly announce to all that can hear you that you are in the market to buy a Boo-Boo. Now for those of you that don’t know, a boo-boo is the traditional African dress for men . It’s the ideal African tourist high-margin product. You should be walking as you say this—this will get you more coverage, and your movement will make the vendors nervous that you’re going to leave. Quickly several boo-boo vendors, ad-hoc brokers for boo-boos, sisters and brothers who know someone who sells boo-boos—they’ll all come out of nowhere to meet your every Boo-Boo desire. Now slow down and stop and let the rush of people settle down a bit, and then ask for the best price of a Boo-Boo, and then start walking again. Get really animated when you get your first price and tell them that they’re crazy and wave your arms, etc. Next, yell out a low-ball price (at least 1/5 of their ask), and start walking away. At this point you should have at least 20 people chasing you down the street. These guys will be yelling at you to visit their “factory” (i.e. their small shop), and b/c things are so competitive, they’ll also start yelling at and pushing each other. Eventually people will start grabbing you and try to physically restrain you, and that’s when you start running down the street.

Dakar Markets in style – take the coolest guy in the crowd that you just ran away from, and offer to hire him for $5 to take you around the markets for a few hours. Tell him his job is to:

a) show you all the awesome stuff in the Dakar street markets

b) help you negotiate on various transactions (a local can get the negotiations started much lower and you waste less time bluffing, calling bluffs as you get down to the best price

c) keep crazy vendors away from you.

Startup Seed Raising Skilzzz

A bunch of companies I’m involved in have gone for seed funding in the last few months. After one of them asked for the ultra-warrior-l33t-skillz, I thought I’d put this post up and break it down.

If any of you are raising your first startup or seed money, this is a must read. Would love to hear any of your stories/feedback in the comments on this post…

Priming the pump: How do you get started with rounding up some angels for a seed round? It’s pretty simple. Go to angel gatherings, industry conferences, any and all networking events. Meet people who are angels or who know angels. Give ‘em the elevator pitch. KEEP IT SHORT. Set up Intro meetings. Also, if you’re not located in a startup hotspot, then find/make a friend in Silicon Valley and stay on his/her couch for a month and make sure you’re meeting with somebody new EVERY DAY.

Intro meetings: Informal discussion where you pitch the company over a lunch/coffee/etc., and expand potential angel network through referrals. Get your pitch down to 5-10 minutes, and prepare a tight FAQ in your head so that you have tight answers to the top 20 questions. Let them pay. Be proud of your scrappiness.

ABC’s – Always Be Closing: At the end of every meeting, get a clear understanding of where they stand on your deal opportunity. Shoot for getting an amount they would be interested in investing. You won’t usually get a commitment on the first meeting but do not accept vagueness. Get a clear idea of where they stand, and what next steps might be to move them through the pipeline. Hypotheticals are also useful: When I lock on my lead investor, how much would you be interested in investing?

Referrals are key: “Glad you’re pumped… any thoughts on who else I should meet with?” If your pitch is kicking ass, then most angels will immediately offer up a couple folks they can hook you up with. Regardless, always ask for more folks you can connect with.

Advisors: Turn a couple of these potential angels into advisors. Having a few top-notch people in your corner can make all the difference in turning the tide in an angel round. Everybody’s going to want to help and everybody will want a piece. Be selective, don’t settle. An average advisor is worth 1/10 the amount of an awesome advisor. Make it known that you expect your advisors to invest in the round. No exceptions—an advisor that doesn’t invest in the round will have significantly less influence in helping you close a round.

Thought Partner: Pick one advisor, co-founder, or mentor who will be your thought partner in managing the process. There is a lot of activity as you go to get your first term sheet, all the way through the close. Strange shit you cannot predict WILL go down. Big personalities, money, valuation, ego, all that makes a nice recipe for some crazy shenanigans. Nailing your messaging, managing the big personalities, keeping momentum going, takes a certain amount of magic, and making that happen is not accidental. It’s hard work, hustle, credibility, and preparation, and you’ll be much better at it with a partner in crime who can help you think through the issues, and craziness that inevitably will go down as you get to closing.

TheList: Keep a list (aka pipeline) of the people you’re meeting with, the referrals that they provide you, and the level of their interest in the seed round. Stay on the ball…Always follow up…be the pro that impresses all those investors that interact with you.

Passion/Charisma: This is the X-factor. It separates the men from the boys in fundraising. If you’re doing a startup, you’re trying to change the world, you’ve kicked your cushy job to the curb, you’ve had Ramen noodles for breakfast lunch and dinner as far as you can remember, and maybe you’ve moved back in with the ‘rents. You’ve definitely got the passion…why else would you be doing this? Don’t be afraid to show it. Every pitch could be your last one (i.e. the dude across the table writes you a check!), know that… give it your all… listen to some music that pumps you up before you get into the meeting, think about all of the great shit you’re doing and could do. Focus on the positive, have confidence, be amped, bring passion to your game, and share the love with the person across from you… bring extreme positivity into the potential investor’s otherwise boring pedestrian day. Watch some of @garyvee to see this in its purest form.

Credibility: DO NOT FIGHT THE TRUTH. If you do, you will become road kill. Do not try to spin out of what your weak points are. Do not try to make something certain that is not. Do not pretend to know something that you don’t. Credibility is the name of the game in fundraising. Every startup investor knows there are uncertainties. We all know there are risks. Accept them for what they are, BUT have a SMART answer for them. How are you addressing the uncertainties? How are you dealing with the risks? Show them you have thought 2 or 3 steps ahead. Be frank and to the point about negative concerns, and always try to focus negative concerns toward your strengths and your positives.

Momentum and Urgency: Investors are fickle creatures, they are motivated by fear and greed, and without it they will take their time and hem and haw at every turn. They will turn a 3 week process into a 6 month process. Time IS NOT YOUR FRIEND! The longer the process drags out, the more it seems that nobody is interested in your deal, and the less likely you are to actually get one… AND even if you do, with every day you will be sinking more time and energy into the process and less into your company. Every communication you have with prospective investors must include a sense of momentum and urgency in the deal process. “Things are moving quickly.” “My day is packed with meetings.” “Many parties are interested.” “This deal could come together quickly.” You back this up with hard work and serious hustle. Keep your update conversations short. Make the Urgency a reality by working your ass off. It will become a self-fufilling prophecy and your deal will get done.

Getting the Lead: You can get all of the investors in the world amped on your deal, but until you have a lead, you don’t have a deal. What is a lead? The lead in a deal is the investor, usually one of the largest, who negotiates the T’s and C’s and essentially sets the terms for the round of funding… essentially providing you with a term sheet. The way to get a lead is to spur one of the larger, most interested investors into making an offer. Ask him what it’s going to take to make a deal happen, what kind of terms he had in mind, what would make this an exciting deal. You can make momentum moves with this request, by making it clear that you’re going to other investors and having the same conversation with them. Make it a matter of “shit or get off the pot” (but in a polite way).

The Competitive Deal – The Need for Speed: The second you have a single term sheet, you need to move *very* quickly to get a second one. You don’t have a lot of time, because momentum at this point is crucial to closing and your first lead does not want to feel like he’s being dicked around. Your second term sheet will be easier to get than your first, but it will make a HUGE impact on your deal. Without a second termsheet, you will be in a position to take whatever crappy terms the original lead provided, and it’s quite possible that the terms could get worse (or even go away!) as the one-termsheet deal drags out. Figure out who those 2 or 3 potential other leads are and hustle the hell out of them. Here’s a voicemail I left on a 2nd termsheet prospect on a recent *competitive* deal I was involved in. The recipient of this voicemail called back in 5 minutes, AND ended up being the lead on the deal (notice the urgency while staying true and credible):

Hey , wanted to check in with you regarding . . .things are heating up with a couple other parties and it looks like things could get done pretty quickly from here… wanted to check in with you, see where you’re head’s at on the deal, and see if we there’s a shot we can work together on this one… give me a call back as soon as you can… talk to you soon

Herding the cattle: Once you start working the competitive leads, you need to start getting word out to ALL of the interested parties, that this deal is getting hot, and that you could start moving to close in very short order. This is key to continue momentum with the deal and keep your potential leads hot. If they know you have $200-300k following their investment, then they feel even better about your company knowing all the other folks are interested too. This makes them anxious about the competitive situation you’ve created b/c now your deal has been validated. On the other side, the small investors that were interested in following, now feel that this is a real deal that they can really follow, and since there are big guys involved putting in real money, they’ll essentially commit to an amount w/o necessarily having all the final terms. Nail those follow-on investors to an amount. Make sure those competitive leads know that you’re bringing a lot of extra money to the table.

Anti-Collusion: Once you lock on your lead investor, there are a lot of terms still left to fill out. The heavyweights in your deal will have the inclination to collude to make the terms better. They know they’re in the deal and the delays that happen when final docs are getting fully locked makes them rambunctious. Keep it short and sweet with each potential colluder, and draw a very straight firm line that the material terms are not changing. That kind of leadership will keep you from having what I call an investor revolt before you even get the deal done.

Sprint through the close: The best entrepreneurs *never* stop selling. The finish line is in their sites, and it’s pretty clear they’re going to make it across, but they don’t let up… they sprint even harder through that finish line. I like to say that until the deal is closed, you have at best a 50/50 shot of it happening. Keep working new seed investors, keep the competitive leads warm, get your deal oversubscribed, because until your deal is done, it’s just a nice fantasy in your head. The best sprinters sprint through the finish line, and the best entrepreneurs sprint through the close.