Miles To Go.

Great name!

Yes, Marissa Mayer is out there honing her strategy for a next move, and lots of buzz is around Mobile Ad-Tech. I’m quite keen to those developments, because of my activity in the space… you might say.

But before her time, Yahoo made an offer that prompted one of the best “What Would you Do” conversations of our generation. I caught the gist of it at during Peter Thiel’s talk at SXSW, but Inc. does a better job of describing it here:

…Facebook was just two years old. It was a college site with roughly eight or nine million people on it. And, though it was making $30 million in revenue, it was not profitable. “And we received an acquisition offer from Yahoo for $1 billion,” Thiel said.   

“Both Briar and myself on balance thought we probably should take the money,” recalled Thiel. “But Zuckerberg started the meeting like, ‘This is kind of a formality, just a quick board meeting, it shouldn’t take more than 10 minutes. We’re obviously not going to sell here’.” 

At the time, Zuckerberg was 22 years old.

Thiel said he remembered saying, “We should probably talk about this. A billion dollars is a lot of money.” They hashed out the conversation. Thiel said he and Breyer pointed out: “You own 25 percent. There’s so much you could do with the money.”Thiel recalled Zuckerberg said, in a nutshell: “I don’t know what I could do with the money. I’d just start another social networking site. I kind of like the one I already have.”

Now for the What Would You Do part- a/k/a- WWYD.

If I were Mark Zuckerberg, I would have done the same. His talent is towering, his vision is far reaching. I would also say his youth might lead some to say he didn’t know what he didn’t know, but Zuckerberg probably did know. He had one great idea, and the likelihood of having another of such epic scale and impact was remote. He knew that lucky and good are not the same thing, and the former rarely strikes twice. He was, and is, part of an asset light generation that I have written about before.

But, I am not Mark Zuckerberg. Not even close.

I am not a sole founder (um, was Zuck?) and I would not imagine to be able to run something myself without the great work of those talented people around me. I might have other ideas I’d like to back, and more entrepreneurs I’d like to work with. I also deeply respect the stakes held by each of my shareholders, and would give due consideration to what they may want as well. Everyone has a number. And working for Yahoo, especially the new Yahoo, might be quite interesting. I may have hit the bid, not being Zuck.

But most of all, I love the fact that it was a ten minute Board meeting, or he thought it should be!

By the way, What would you do?

Krish, Miles, Dan (who is in a rare moment of overdressed) in 2008

This past month marked the fifth year of working together with my two co-founders at Mojiva: Dan and Krish. If I were a DJ spinning vinyl to sum up those days, I would drop the needle with Bob Seger’s Against the Wind. With a few edits…

It seems like yesterday
But it was long ago
[Mobile] was lovely, she was the queen of our nights
There in the darkness with the radio playing low
And the secrets that we shared
The mountains that we moved
Caught like a wildfire out of control
Till there was nothing left to burn and nothing left to prove

Call it founder bias, nostalgic, or just plain sappy but it is amazing what’s has actually gone down in sixty short months. No one has been in mobile very long- old timers can claim ten years, most likely five is when the early scouts hit the beach. Apple was just about to launch the iPhone and end the carrier’s dominance of the “deck”. Premium publishers that took down minimum guarantees were not getting repeat business. Android didn’t exist. There were no apps, and no tablets either. No one knew the difference between online ad-tech and mobile, and how soon they might converge. Wow, that world was simple! It’s now Flintstones vs. Jetsons!

First thing we did, of course, was to name the damn thing. It may sound like a whim, but we actually worked hard to craft a name that had meaning- at least to us three. MoJiva was a mash up of jivan, which is a Hindi god (we favored the elephant Ganesh) and Mo for mobile of course. The good thing about crazy names is they are always available at register.com. And everyone has remembered us since.

We gave Krish $300k and 3 months to build the mOcean platform (he’s had a bit more budget lately!). In light of what developed, that amount just seems ridiculous. But that’s how it went down, and build it he did. We served 3M ads a day by month 3, and we felt like we were on fire. Three months later, we raised Series A from a strategic VC and hired a rock star CEO. Dan got going on Biz dev, and we went on a run. I can’t even begin to list the milestones along the way: often it seemed like we were on a runaway train, fixing the front wheels even as we were shoveling coal, painting the cabins and losing luggage out the caboose. Such is the world of start ups and technology. It takes a strong stomach and a keen eye for the rewards at the end.

And I remember what she said to me
How she swore that it never would end
I remember how she held me oh so tight
Wish I didn’t know now what I didn’t know then

Against the wind
We were runnin’ against the wind
We were young and strong, we were runnin’ against the wind

Amazing what you can accomplish when you don’t know any better. Everything we did was against the odds, let alone the wind. And now its five years on and we just completed another monster milestone year. We are now part of one of the best teams in Mobile ad-tech, over 100 strong. We’ve booked 100% growth for four straight years, and we now serve over 1,000,000,000 ads a day. Yes, that’s a billion ads a day. I had to write that out. In the December rush, we were serving 35,000 ads per second in virtually every country in the world.

But what makes me most proud is the team that we have built and what THEY have accomplished, sometimes by adding people, sometimes by subtracting. From day one, folks walk into our office and universally say Wow! This place is cool- I’d love to work here. Yeah, it’s packed now and someone needs to do the dishes. But we have a wonderful HR effort that backs it up with training, 401k, healthy Mojiva, Core values we live by, peer awards, leave bonuses, flex time, A Player recruiting… and a very open environment where every suggestion to make it better is heard (ok, not all are actionable), and we truly believe in the value of their equity, cause we all own it.

It’s flattering and humbling to consider this came from our DNA, and that vision we cobbled together 5 years ago is still going strong today. There’s more to the song of course, and there’s more to the story to be told. But I want to stop here and tip my hat to my two co-founders and say wow: we helped build that!

Nice job guys!

Gate is actually the basis of the Vaux Logo

Despite focusing most of my writing efforts on my blog, and keeping up with the world via my twitter the year-end letter to Vaux angels is a tradition well worth continuing. I’ve cribbed the best of it here…

 Discover. Develop. Deliver.

These three words are scrawled across everything I do for Vaux. They are three parts of my personal mission to success as entrepreneur and angel investor, which I had the honor of mapping out in a 2012 white paper for the Family Office Association  “Angel Investing for the Family Office” . I took a hard look at the process of building a foundation on the long journey from inception to exit, and nowadays I plan my week based on these categories. I color code each meeting in my outlook. They might as well be scrawled on my bathroom mirror in lipstick. They are the cycle of life for Vaux les Ventures and the angels that have supported these endeavors for nearly 10 years. Here’s what these simple words mean to me:

Discover is about being very focused on what you can do well, and what markets will have an impact that can generate angel returns. Big market trends that people don’t yet see, or are unwilling to accept. Trends that will obviously converge, but no one knows exactly when. It means being early and brave, but it also means being patient to find the right mix that can sustain the long march. This is where the DNA of the business is set: habits formed early are virtually impossible to break. Many people in the business call this “deal flow”, and I did too for a while but I soured on the term as too many IB ‘s and VC’s (both of which I have been) over-use it. Having a well know criteria for how to invest and who to invest with seems to do very well in attracting the right types of people. So does being a good guy. But it’s about discovery as much as it is about network. And that discovery includes markets and their real problems as well as solutions and the best team to build them.

A recent example of this would be my work on WellAware, the mobile health solution. I’m as committed as ever to the trend of mobile devices having profound affect on health and wellness. And I truly believe that very simple data can have tremendous impact on lives. The Wellaware team did a tremendous job developing the platform for this theory to play out, but certainly overshot the MVP standard. What we need in 2013 is more cycles with large user bases to refine our solution, likely in the mobile environment.

Develop is where the entrepreneur (in anyone!) takes over: translating a vision for a product solution into a product itself, and testing it with users to see if the darn thing works. It takes tremendous amounts of courage, persistence and luck. Some attempts are ridiculously off the mark. Ironically, more often there are overshots than undershots when going for the minimally viable product. And users are rarely the viral dream everyone hopes for- more like a block-by-block struggle to get to a vantage point where people notice you. But more than product and users, the team is the big part of the develop picture. Entrepreneurs have a passion for building things are not always Schwartkoffs when it comes to leading people. And that is where the coaching and mentoring foundation is laid. Capital begins to show up at this point, as we have baked enough of the risk out of the opportunity for larger sources of capital to begin to show interest. That too is a major challenge in this phase, and if you grow fast enough, it never ends.

[Major edits here from the angel letter. Sorry, that's not public.]

The poster child for the develop phase is certainly TrustCloud, which just 9 months ago had product solution in search of a problem, no user base, and a team that had already endured a few pivots. Such are the risks of being early! But the saving grace was each of the founders used the sharing economy and saw what it could deliver, as well as its limitations. Something had to give, we thought.

And 2012 was full of such breaks, as TrustCloud found its core team, delivered a product and began building users at an impressive clip  (10x from July to December) after the Wall Street Journal picked us up. Check out the product here, or the very impressive Facebook TrustCloud user group (which tracks bugs and promotes the product passionately). The Company rolls into the New Year with a new Peer Protect insurance product to couple with it’s ever growing number of sharing networks.  Kudos to the indefatigable and imminently coachable CEO Xin Chung, who details the year here:

 I shared keys to my NYC apartment on Airbnb, rides through San Francisco in a Sidecar, and my workload with TaskRabbits. I’m not alone– people worldwide are sharing more than ever with millions of room-nights booked, cars rented, and dogs walked by reputable strangers. The movement is called The Sharing Economy, Collaborative Consumption, or as Mary Meeker calls it, living Asset Light. (this is a great read! Don’t miss it!)

 Flush with VC funding, the movement scaled fast in 2012– but not without growing pains: A quick look at recent sharing history would give anyone pause before sharing with a stranger. Home sharing market leader Airbnb had a redux of its 2011 EJ incident with the so-called airbed & brothel snafu where a Swedish apartment was literally pimped-out. Carsharing had it’s own collisions with the luxury carsharing service HiGear shutting down due to thefts, car sharer RelayRides’ liability issues with a fatality crash, and regulatory fines for on-demand ride-sharers.

 These events highlighted that trust between strangers in peer-to-peer marketplaces must keep pace with their own rapid growth. In the offline world, hotels have long adopted star ratings, rental cars are licensed and insured by brands spend billions to give consumers confidence to buy. Since online, peer to-peer marketplaces powered by micro-entrepreneurs don’t have time to brand themselves or vet strangers, they are much less efficient as buyers and sellers waste time sizing each other up, figuring out a schedule and even haggling over price before committing. Trust can make these transactions much faster, and insuring the risk is something we look forward to. Read more at TrustCloud’s Blog.

Deliver is where all the hard work pays off. That would seem like a triumphant moment, and I’ll allow myself a few. But as I have matured it has become a little more bittersweet. Here are companies we have built from scratch, communities that started with a handful of people, angel capital that came in for under $1M pre money. And despite some intermittent liquidity opportunities, in some cases these companies have futures that remain bright(er). We have seen large that we turned down; we may see 2x-3x-4x from here (or of course, we may not). So parting with some or all of the ownership isn’t as easy as “see ya later”. It’s an asset, with a value that has to be managed detachment that is at arms’ length, hard as that may be. We also live in a world of high risk, so those precious few windows of liquidity opportunity have to be considered when they are open.

[More major edits here from the angel letter. Sorry, that's not public.]

In summary, I guess I feel every venture I have been involved with has contributed to the next. Things I have learned about the Discover phase have allowed for better Develop results. Those few short peeks at liquidity in Deliver have been viewed with a paradigm that allows the whole group to consider individualized risk and reward before deciding on liquidity. And of course, the success through the process has allowed us the opportunity to feed the beast, return to what we do best, and further diversify with another opportunity.

I am extremely grateful for the opportunity to work in the field that I do, side by side with talented entrepreneurs, backed by caring and value adding angels that ask good questions and have the patience to help realize the vision I had almost ten years ago. We’ll see great opportunities in each of the three key Phases in 2013. Drop me a line and we’ll discuss which ones best fit your criteria in the days ahead.

All my best in the New Year,

Meet Fake Grimlock

Mary Meeker just called it: Sharing is now a megatrend.

In her wildly popular bi-annual prognosis, Meeker points to the demise of asset-heavy life especially among 20 somethings wherebye sharing economy and  smartphones free time and money, creating an asset-light generation.

So how does this relate to virtual dinosaurs and dating? Hang on, let me tell a good story. Dialing it back a bit, I was watching Cat in the Hat with my son this morning and began to wonder about how that famous tech character might teach us something about a this big trend, now that Mary called it. Suppose I pose these questions abut the tech world’s favorite virtual persona Fake Grimlock… as only Dr. Seuss could:

Would you meet him in a mall? Would you pass him in the hall?
Would you let him drive your car? Would you let him drive it far?
Would you let him watch your pet? Would he eat them, hmm, sure bet?
Would you let him tutor the kids? Could you, would you blink an eyelid?
Would you let him sleep upon your couch? Would he scare you with those teeth- Ouch!
Would you date him late at night? Would you lend him money? Right!

Which means, essentially, if you were going to do a “Sharing Transaction” with an unknown Peer, do you trust the person behind fake grimlock? He’s extremely well known in a small circle of tech entrepreneurs (and deservedly so- he’s hilarious in a CAPSLOCK kinda way). But my point is, there are millions and millions of Fake Grimlocks out there.

From Spencer 323232 on gMail to Pineapple88 on EBay, people have for more than a decade created and maintained personas and avatars for everything from virtual gaming to very real Craig’s listings. Taking it back to Dot.com days, we used to hear the reason the internet was popular was … no one knew you were a dog. People could go online (Chatrooms!) under any handle they chose and behave pretty much with impunity. It was the digital equivalent of turning out the lights at a teen mixer. Stupid ideas came and went, as did plenty of fortunes and not a few great companies. But the ability to take on an alias, or even build an avatar in another parallel world lingered as a quaint benefit from back in the day. To some gaming sites, it’s a hell of a business that virtual world.

But now comes along Social, Mobile and Local where a billion people share their profiles, activities, photos and innermost thoughts with perhaps way too many friends. Privacy was redefined, or its boundaries were pushed out by the devils favorite vice, vanity. Rachel Botsman called it early with her Colaborative Consumption moniker, and subsequently has talked about trust within peer networks a lot. Now, as big data companies are starting to realize this data is meaningful, strong voices are pointing out that people should own their own data. Tim Berners Lee is one such voice, having started what I call the “Data to the People” movement with this Guardian interview. Add to this a rich mix of a green consciousness, underemployed/over-indebted college graduates and a sluggish economy and you get the Sharing Economy a/k/a the very more wordy Collaborative Consumption. Al it needs now is some glue, or as Neal Gorenflo recently said in a post to Shareable Magazine the dramatic transformation of the economy that’s needed is not going to happen until a large coalition begins to work together.

This is precisely why companies like TrustCloud, Connect.me  and MiiCard are helping stitch together a trust and reputation metric for the Peer economy. Basically, in 2012 everyone knows you are  dinosaur, and if you are transparent enough with it, more and more people are ok with it. So, for argument’s sake, let’s say Grimlock does not want to reveal his identity, but he wants to claim credit for all the good things he has done online. He has a ton of influence and follows (you can see that from twitter or Klout) but maybe he also contributes to Stack Overflow and helps out on GitHub under Grimmy22. Maybe he maintains an ebay account where he is top rated as a seller, but under FakeyBoy101. He has a few verifiable email addresses, and actually lives somewhere under the name Human B. Good. What if Human B Good claimed all that data and consolidated in one place- without actually divulging that he was Grimmy22, FakeyBoy101 or any other avatar. But he claimed the credit for all the good things he does for the community under whatever name. If he was transparent enough to verify and share his human identity, he’d be golden, or the human behind him would be. And all without blowing the connection to the mysterious Grimlock. Here’s my point: thousands of people every week are coming to that conclusion and getting TrustCards.

So… let’s look again at these peer transactions

Would you meet him in a mall? Would you pass him in the hall? 

This is the perfect CraigsList question. If Grimlock offered me $100 cash for my old iPhone in some dodgy exchange in the mall parking lot, it’s a pass. To much risk there. But if Human B. Good made the same offer (and had claimed all the virtuous data Grimock threw off), it would be a different story.

Would you let him drive your car? Would you let him drive it far?

This is the GetAround/Relay Rides/ Ridepost question. As Anotonin Leonard’s partner Benjamin Tinq (both OuiShare guys) remarked, “Ten years after Jeremy Rifkin wrote The Age of Access, shared mobility is fundamentally changing the way people think about car ownership, among other things. Especially the younger ones, to whom owning a car has lost its appeal of independance, which is now embodied by electronic and social media devices. So you want me to hand over the keys to  a $30k asset so Grimlock and his monster buddies can go up skiing Vermont for the weekend, and he will give me… $30 per day? Can you say asymmetrical risk? And for some extra credit reading, has anyone really looked at their insurance coverage when you turn your car into a small business. The answer is pretty disappointing (and the backup from the sponsoring sharing network won’t be good for much either, especially as that risk scales). But Human B. Good give me a better feeling about his identity, interactions and behavior with his TrustScore. Perhaps things would have been better for HighGear had they such a system in place. RideShare is already doing this, and more will follow I think.

Would you let him watch your pet? Would he eat them, hmm, sure bet?

Talk about precious assets! I would not turn Baxter over to Grimlock for fear of dinner! Rover.com is already onto this, and has trustscores flowing out to their 70,000 dog watchers nationwide. Essentially, people Human B. Good would get the job, and Baxter would come home safe (and incidentally, my home would be safe, seeing as how Human B. Good has the keys to the house).

Would you let him sleep upon your couch? Would he scare you with those teeth- Ouch!

This one comes right out of AirBnB’s book- and Wimdu, LoveHomeSwap, HomeAway, InterHome and lots of others. While millions of room nights have been booked, as the early adopted give way to a more mass acceptance of “crashing on the couch”, so to will a demand grow for “who is this”, and from both sides of the transaction. AirBnB has had its “Ej Incident” and the “Hookers on Holiday“, which at the very least left a bad taste (sorry) for the hosts. I’ve heard there are plenty more where those came from. But there is risk on the guest side as well, just ask the poor blokes who wired in advance for their Fun and Sun Holiday in France and got… (sorry) just pictures for their trouble (the house did not exist), and the hosts, well what do you think? Again, no keys in this scenario for Grimlock. Human B. Good, more likely.

Would you date him late at night? Would you lend him money? Right!

So after the roundup of the “Sharing Companies”, it makes sense to imagine the other places that a trust and identity system could help other Peer economies. While I have heard stories of young ladies throwing themselves at Grimlock at his personal appearances, I’m not so sure that is scalable. Dating is the ultimate peer transaction, and one where a few simple verifications would do a world of good. To wit: a) does the guy really make $100k+ and b) are those photos of the girl recent or retouched? Likewise, peer lending could be greatly enhanced with a similar solution. Of course, the incidence and transaction data that flows back through the intake API becomes crucial to the richness of the scores.

So to wrap this one in a bow… there is a great saying about trust and context: I would trust my dog with my life, but not with my hamburger.

Grimlock has done a good many great things for our tech community across a few social networks. He is known to the community, and he adds to it. And that’s fine for the virtual world. But for the rest of us, so much of our lives pass between the virtual and real worlds. And many of us have piled up so much virtuous data, it’s time to start harvesting it, claiming it and organizing it in one place that makes it useful to a variety of networks.

We all have our data from our own versions of Grimlock out there. Start using it.

 Full disclosure: I mention TrustCloud here. I am an angel investor in same. 

This way, or that way? (Photo ABC News)

This year’s Presidential Election will be the most important in my lifetime… as per usual.

I was a fan of politics back in the day, when the process itself didn’t make me puke. I tuned in to the weekend talk shows eager to see who would say what, and even the most sold-out of hosts played it pretty middle of the road. I did the same this weekend: the most memorable prognosis was David Gergen who went so far as to say we may see a landslide, but he didn’t know for who…

Though I’m just a guy from Pittsburgh, I ended up living in a data driven world, and dealing with a lot of coastals. So I’ve been fascinated with a few interesting graphs like the Path to the White House from the NYTimes and Nate Silver’s BET THE FARM prognosis called 538. After 18 months, there are still hundred of permutations on the path to to 1600 Pennsylvania Avenue… which the rest of the world thinks is another exhibit for America’s case for self-inflicted insanity.

I also live in a world driven by Mobile and social – in fact I helped create it. I’m impressed (or bored or perturbed) by the frequency of Facebook or Twitter posts from friends who feel it’s a good time to share the scoop on the latest Gotcha charge from either camp. Events move dramatically, though they are played out before less people than back in the day, on network TV. Witness this week’s Sandy Storm; it featured the horror of Boardwalks falling into the sea (they are boards!), to cancelled marathons, to inter-party wet kisses on the jersey Shore in exchange for first dibs on FEMA help. Yet most of the rest of the country was faurly clueless as to the true effects of the storm. Or take the singular issue of the election:  jobs. That’s the one thing that will save our economy, but that debate turned to offshoring, tax burdens and the auto bailout. The real value added jobs created by entrepreneurs are too often overlooked.

Those that follow are more engaged, more vocal… and thank god only carry just one vote apiece. This Presidential Election has certainly set a record for skewing of the truth and for willingness to play for the margin of error in states that still count. Nixon campaigned in 49 states in the last month of his election… Romney and Obama, more like a handful. The rest didn’t matter. Data has allowed us to zero in on the few votes that hang in the balance. And our mobile social world have allowed us, even driven us, to magnify differences among ourselves in order to make a breakaway move, left or right.

“If we are victorious in one more battle, we shall be utterly ruined.” King Pyrrhus once said. And indeed, my prediction is the winner tomorrow will face an impossibly divided Congress, a debt burdened Treasury, and a society whose place in the world would best be managed as a soft landing.

Good luck with that.

I think it’s a lock: our next President will be Pyrrhic.

Charlie Green, author of Trusted Advisor

(MS) Since there is so much buzz around Sharing, (I’ve written about it recently here, here and here) and it’s key component, Trust, I’ve asked some experts to lend their opinions on my blog to fill out the color commentary. Here’s Charlie Green;

Whether you call it “the sharing economy” or “collaborative consumption,” there’s a fascinating new economic and social phenomenon going on.  While not identical, both terms refer to markets for the sharing of products and services between individuals.

It may seem obvious that the role of trust is pretty critical. But just what that role is turns out to be not so obvious.    

Background

The chroniclers of the movement are Rachel Botsman (Botsman & Rogers, What’s Mine is Yours), and Lisa Gansky (The Mesh: Why the Future of Business is Sharing). Botsman characterizes three sub-markets: product-services systems (like ZipCar), redistribution markets (eBay), and collaborative lifestyles (CouchSurfing).

Some of those sub-markets hint at huge scale economies: how many zillions of available-seat-miles go unused on the nation’s streets and highways on driver-only trips? How many available car-hours per day are actually used for driving, as opposed to uselessly hogging valuable real estate? And for nearly every traveler vacationing, there’s an empty house back home going unutilized.

Other sub-markets are more akin to intriguing social experiments: imagine a global foreign exchange student program run for adults, only faster, bigger, and with do-it-yourself vetting, and you’ve got something like CouchSurfing.

In an odd way, “markets” is precisely the wrong way to describe the social experiment part of the phenomenon – it’s anti-market, in a sense, to focus on collaboration and reduced consumption, rather than on increased sales and  intermediating exchanges.

But in more traditional senses, these are very much markets, with loads of interest. Technologies are enabling peer-to-peer interactions; but unlike stock exchanges and book-buying, many of them exist to facilitate real flesh-and-blood interactions. Subletting your house or apartment to someone, or simply hosting an out-of-town visitor, is no trivial social exercise. And lending out your car or tools, while not necessarily social, also involves a social risk.

Which is where trust comes in.

Trust in the Sharing Economy

If you’re going to open up your house to someone you’ve never met before, you will make some form of trust calculus about the possible guest.

The reverse is true as well: if you’re going to go spend some time as the house-guest of a perfect stranger, you also will make some assessment along the lines of, “Do I, or do I not, trust these people?”

Might there be a secondary market here for trust. Indeed, there might.  (Disclosure: I have a small relationship with one such venture, TrustCloud). Suddenly, the decision to trust has economic, and possibly very personal, consequences.

Trusting and Being Trustworthy.  People often talk about “trust” as if it were a single thing.  It’s not.  “Trust” is the result of a trustor and a trustee arriving at an agreement. Trusting is not the same as being trusted. Trust is, if you’ll pardon the abstract language, an asymmetric relationship.

To be clear, the one doing the trusting (the trustor) is the one taking the risk. If I loan my tools or house to you, you might abuse them. The trustee, by contrast, takes little risk.

The trustor’s decision is based partly on the perception of the trustworthiness of the trustee. Wouldn’t it be great, the thinking goes, if we could come up with the equivalent of a FICO credit score for would-be trustees.

The search for trustworthiness metrics goes in two directions. One is reputation;  the other is behavior. Reputation is relatively easy to assess; unfortunately, it’s also easy to game, and can easily be confused with notoriety. Kim Kardashian may score high on reputation, and even influence – but does that mean you trust her?

Behavior is harder to game: to fake behavioral dependability, I would have to establish a track record of dependable behavior – which is, after all, the point. It can be faked, of course, but such an elaborate con requires a level of effort quite out of proportion to the benefit, not to mention out of character.

Trusting. It’s easy to focus just on measuring trustworthiness, particularly in the product-services and redistribution markets, where the trustor wants information about the trustee to mitigate downside risk.

But in the collaborative lifestyles segments of the movement, it’s not just the trustworthiness of the trustee that is important, but also the trustor’s propensity to trust. In the fascinating sub-movement that is Couchsurfing, the parties aren’t just looking to cut risk: they want upside potential in terms of fascinating people willing to take social risks in order to meet others. They want trustors.

The 60s Redux?

The parallel with the 60s is instructive. Some of the era’s social experimentation didn’t make it out of the 70s. But the Beatles, Steve Jobs, and the Grateful Dead were all once-radical types who created models that are mainstream business today.

Even the hard-core economic segments of the sharing economy aren’t as radical as we think. The timeshare industry “shared” underutilized vacation home capacity; so did distributed computing in the 70s-80s. McDonalds’ discovery of breakfast was another capacity utilization play that paid off big.

In any case, we’re all going to be talking more about trust. And that’s likely a good thing for us all.

The Social Network is a hell of a movie, but the real people upon whom the characters were based have stated that the film’s version of the founding and growth of Facebook was overly dramatized. And appeared way more fun than it actually was.

Face it, entrepreneurship is hard. Angel investing is doubly hard. While we read about spectacular successes, one can hardly keep up with the many outright failures preceding them. The thin veil  can really only be perceived once you are on the right side of it-it’s practically see through! But if you are on the wrong side, the thin veil might as well be a brick wall.

Someone once said the two best traits an angel investor can possess are a strong stomach and a sense of humor. The strong stomach will tolerate its share of quick deaths from being too early, too late, poor execution or leadership, lack of funds, or just tons of competition. The sense of humor will come into play when you attempt to tell your God which element of your portfolio is going to be The Big One. God will invariably laugh and throw at least one thunderbolt, wreaking havoc with your “sure thing” — but turning your also-ran into a winner. (No kidding, it’s happened. But to protect the innocent, we won’t name those we feel were luckier than they were skilled.)

Other sources of angel heartburn include those frustrating periods of illiquidity…the fast pace of technology which upends business models and proprietary positions quicker than at any time in history… the global markets bringing competition to one’s door on a massive scale… the high valuations of exposed deals,…the lack of influence when part of a syndicate…the competition with other angels (and now, VC’s). The list goes on.

The angel game can be summed up in the words of the “advert” placed by explorer Ernest Shackleton (1874-1922) ahead of his Antarctic expeditions (none of them successful, by the way):

“MEN WANTED FOR HAZARDOUS JOURNEY.

SMALL WAGES, BITTER COLD, LONG MONTHS OF COMPLETE DARKNESS.

CONSTANT DANGER, SAFE RETURN DOUBTFUL.

HONOR AND RECOGNITION IN CASE OF SUCCESS.”

And yet, we do it.