Your winnings, Sir.

So, the NSA has been snooping the data at most of the big Silicon Valley tech titans, who snoop the data of most of the planet. The former is looking for bad guys, the latter are looking for customers.

What’s the diff?

What cracks me up is the outrage. It reminds me of Captain Renault’s great line outside Rick’s Cafe the night he shut it down.

How did we get to this place?

Data used to be such a hard and fast thing. Name, address, and social security was plenty to get a verification going. It worked well for high stakes actions like getting a mortgage, a car loan, a college education… and it still does. The titans of big data and credit have built tremendous businesses based primarily on that data. But it’s getting tired, and the options for passing that data between them is getting more finite with every day.

However, a new generation is beginning to emerge. One without much credit, poor job prospects, shared homes, and many other traits that make them look like ghosts on paper. How to get a read on these guys? All they have are mobile phones and social networks which allow them temporary access to some of the things their parents owned (this is currently called sharing). Well, Zuck and the devil (not to be confused) both had it figured out: vanity is the world’s favorite sin. ….(i acknowledge the irony, as the guy writing a blog . The biggest affect of being mobile and social is the astounding amount of data that it throws off.

Facebook and the rest have masterfully used that data to imply the best ad to suggest a user, the best hotel in the area, the best gift for someone. Even the best match for you to date, lend a car, share a spare room, or walk your dog. That intelligence has gone way beyond the stale cookies of the online world; while not knowing your name, the parameters captured on mobile can include location, screen size, device type, apps open etc. Add to this what users willingly volunteer in their posts, comments, likes, reviews and you have a treasure trove of behavioral data to crunch. I know this from my experience at Mojiva, where we process 35,000 ads per second and analyse 1.5 terabytes of data a day.

Now how is the government supposed to resist all that?

And so now… the Outrage?

So while we as a younger planet willingly volunteer all kind of vanity data in an effort to look good, somehow some of us get outraged when it’s used for national security instead of recommendations for underwear.

I imagine the elders want to remain in the hard data world, and may react negatively to all this digital spy-craft. They own the assets – and the debt to support it – and their address, social security and FiCa will forever be their go-to data. For this group, railing on the government for something they don’t yet understand (like why would anyone want to know my behavior and preferences) is pretty logical, if not up to date. And on the other side of the spectrum, any mobile social junkie with 33 dukedoms on Yelp and a 800+ score on TrustCloud can’t possibly say “my public data has it’s limitations” … it’s all opt in and public anyways.

And there is the generational disconnect that conceals an emerging opportunity.

Those that were and still are accustomed to hard and real data as the one-and-only arbiter of trust-worthiness are going to quickly pass from majority to minority. You can’t look at this slide from Mary Meeker on how we spend our time and debate the effect of mobile. People are choosing to spend their time in places that throw off more data and indicators for the new world. And while the soft data from mobile and social are not yet enough to fully vet “worthiness”, those that recognize leverage of the combination of the two will prevail in the next chapter of “data as indicator”.

Let’s just call it like it is, Rick

Despite all the protests, we’re getting to the cusp of a new world, where hard data (FICA, mortgage, etc.) is going to meet with softer, more contextual data (mobile, social) to form new benchmarks of trust in our world. I suspect Zuck and the devil will prevail on this one, if not together then in league. And we’ll come to accept our digital behavior as an important component of who we are. Our mortgages as well as our underwear selections will be smarter because of it.

Get over it people. Rick already has.

Epic Cover from Popular Mechanics c’94

Ever wonder what goes on behind the scenes when you pull up some information on your mobile device or tablet like today’s Weather Channel outlook or last nights scores on ESPN? Ever been annoyed by the ad intruding on what you want to look at, or if it’s behaving but not being relevant at all. What goes on behind the scenes, in about 1/1000th of a second, is a remarkable battle for the right deliver a message from someone who wants to engage you.

Flattered? Well you (and about 6 billion other people) are one of the two pillars that anchor a giant eco-system that is defining our times. Congratulations.

But the pipes that run between the brand that wants to reach you and the mobile device you are looking are new, not fully developed, filled with billions of dollars, and clogged with FUD. For the un-initiated, that’s Fear-Uncertainty-and-Doubt. When it gets solved, it will mean more and better content supported by relevant and timely ads that actually add to the experience.

In the meantime, let me (try to) explain what we (the businesses behind this) are working on to bring you to that point…

The pipe is all the different ways a brand can reach a consumer on a mobile device (explained below). The hold up revolves around people’s natural resistance to change, and their comfort with the familiar. I’m not immune to that, and I can remember a turning point about mid-way through the dot-com era when I lamented to a few of my old school buyout friends “remember when we used to be able to buy a company and phone it in for 5-10 years without anyone messing with us”?. Thomas Friedman got that right in his World is Flat, stating that our ability to learn and adapt will become the greatest skill set for the modern world. As markets and models change overnight, those that resist change and evolution will inevitably become a smaller and smaller island, if not altogether sunk. And who’s to blame for all this?

The information super highway for one. And for two, creative destruction went from Generational to 140 characters. Which brings us back to mobile ad-tech.

For an outsider, there is nothing more exciting than the tectonic shift of time spent from TV and PC to Mobile and Tablet. Though I write this on a PC (Mac) there are fewer and fewer tasks that get completed in front of this screen. And the brands that want to reach me are beginning to figure this out: the ads are getting smarter, more relevant, less intrusive and – dare I say – value ad on occasion. And this is done without cookies (on mobile) but with many more interesting parameters. But, like the internet’s early days, it’s still got a long way to go.

Segue here for first timers: my theory remains that as consumers get access to more information faster, they want more information, faster. And, like the internet, they will not like to pay for any of that. So the brands who want to access those consumers will subsidize that content with advertising support. And one way or another, that’s how we’ll roll for a while here.

So why do outsiders and first timers make such a big deal about the complexity and fragmentation of the mobile ads ecosystem? FUD. Listening to the CM Summit – thanks Google for the live stream- Luma’s Terry Kawaga  (start at 1:17:45) uses a showman’s flair for ridiculous sound effects and funny mash-ups while drawing out the following truth: there are only two pillars in digital media, consumer and brand. Everyone else is an enabler to that connection. If you get confused while looking a LumaScape, just repeat the preceding sentence. Here are the rest of the players, per Terry:

• Publishers create content of interest, where consumers flock like birds of a feather.
• Agencies create interesting ad units, and control lots of ad buys
• Networks buy and sell the remnants the publishers can’t sell themselves
• Exchanges automate the process
• Data targets users for more unique ad delivery

My world. Welcome.

And if you are gazing upon the Mobile LumaScape for the first time, you might say I guess I won’t be able to phone it in for 5-10 years without anyone messing with me. So this is where it gets interesting, as Terry again point out. Those enablers between the consumer and the brand tend to welcome the newbies with the following line

Oh, yes it’s very confusing. Give me your money and I’ll make it better.

Which is a lazy way to look at it. Yes, there’s a bunch of logos up there but he has the basics in the right place: Consumer and Brand. In between, there are a bunch of petri dishes founded by innovators, funded by vc’s, helping find better solutions between the two. But playing the game of fear (this is so confusing) and hero (but I can save you, give me your money) will not advance any of the said petri dishes. What will advance and differentiate them is seamless integrations between the petri dishes such that a brand can plug-in and gain the benefits of any and all of the innovations that allow it to best reach the consumer at the best time with the best ad.

And all this will normalize into something pretty logical I think. Just look at the same video at 1:28:00, about pop-ups. They were hated online, and they eventually receded or were trimmed back. They are no less hated in mobile, and likewise they will not win by dominating the screen. They will win by being relevant and timely and reaching the consumer when they need it most.

So that’s what’s going on each time you pull up a page on your mobile.

~~

While not mentioned directly, I’d be remiss if I did not disclose I founded a mobile ad-tech company that powers several logos above: Mocean Mobile.

Xin’s Thoughtful Gift: PBJ and Ramen 2

Being an entrepreneur is a lumpy business at best. And while I’ve written extensively about the mortality rate (95%), I’ve never written about how hard it is along the way for those 5% destined for greatness.

It ain’t easy, and it ain’t easy on everyone.

This is a basket of Ramen Noodles and Peanut Butter, presented on my Birthday by a very appropriate, thoughtful entrepreneur I backed; Xin Chung. Xin certainly has the moral authority to present the gift: he was liberated from Saigon as a child, spent time in an internment camp, and grew up in Valdez Alaska before settling in to SoCal and pursuing his dreams as an entrepreneur. He is now Founder and CEO of TrustCloud which has emerged from a “walk in the wilderness” with 10k passionate users and a growing number of interested clients in the social check space.

The Ramen and PBJ is our shorthand for being capital efficient, a must for start-ups.

My system at Vaux usually provides $250k of less for a team to develop a product that addresses a meaningful market problem, and do it within 90 days or so. This means most for the proceeds are dedicated to product. The next $250k usually goes to determining if anyone cares. The numbers vary, but either way the Founders and early employees do not get rich in salaries off of angel money. Frankly, they have to be prepared to barely eat, and when they do eat for strength. This is part of the ugly underbelly – and not a full underbelly! – of the dedication it takes to pursue your dreams. Every dollar you don’t waste can go to a better product or a better viral coefficient.

And of course, stuff takes longer than you expect. And costs more money than planned. This puts tons of pressure on the entrepreneurs as they debate the next crucial steps, often on an empty stomach. Probably once in my last 10 start-ups has a company got it right, right out of the box and kept doubling down all the way. Most try with a product, revamp, try again, tweak, and try again until there’s no track left. And it leads to some very difficult conversations about where to invest precious resources: make the product better and more people will come… or tell more people about the product and they will spread the word. Development vs. Marketing vs. Biz Dev. It often provokes difficult conversations, and sometimes desperate measures (these guys slept in a van on a Biz Dev road trip that lasted months).

And so the entrepreneurs themselves, while pursuing their dreams of autonomy, making a mark on the universe and yes winning riches, have to absorb the vagaries of what precious resources to assign where… including their own sustenance. I get queasy when I hear comparisons to the comp someone could make in the corporate world, which simply doesn’t apply in start-up-ville. And I get nauseous when I hear debates about how deep down the rabbit hole start-ups should go pursuing the next pivot (which is another term for fail and try again). Luckily  angels don’t have that much patience or that much capital for endless restarts. Which is why, when interviewing prospective partners I always look for that unique combination of resourcefulness, willingness and mental toughness that will see us through. And a dose of reality to know when to put a fork in it.

Entrepreneurship is not a straight line to the summit, it’s a jagged ascent and we have to be prepared for the whole ascent not just the sprint at the top.

~~

Save runway: TrustCloud’s sample T&E guidelines

Use personal credit card; expense every month with invoice. Avg trip: 2nts/3days, $800, $1000max

1. Air: economy $250

2. Ground:  $25/day

3. Lodging: Airbnb $50/nt

4. Entertainment: $75/day

5. Badges: pre-approved

6. Big dinners: pre-approved

Start Up Choate NYC

Ivan Taback and Proskauer hosted the final at bat of our Start Up // Choate Spring Road trip in their gorgeous space at 11 Times Square. It was a fitting finale to a great week which gathered over 100 Choaties from three cities to network, learn, and share experiences about starting and growing businesses.

The Panel was definitely skewed young and mobile, with Alex Moazed and NT Etuk joining me for the final night. We polled the crowd and we surprised to learn that there were 10 entrepreneurs, 6 angels, 8 service developers among the crowd that gathered. All said, I’d estimate 2/3 of the crowds in all three cities were involved one way or another with start-ups in their everyday lives.

Who knew.

As usual, the panel had some great nuggets to share. Here we some of my favorites from NYC: When we talked about forming an ideal team and looking for co-founders, NT Etuk said “Don’t look for a partner in the mirror” – meaning having opposing points of view when developing a product, a business, and an organization is key. When we discussed “what would be the plastics for tomorrow”, Alex Moazed was sure that mobile was the answer for how profoundly is has affected our lives just five years into the show. He also added the analogy of the toy business, which never got around to thinking like a tech company: result is that toys (plastics, plush, etc) are now $20B industry, and digital games are about $18B. Gotcha.

Here were some of my favorites from Boston and San Fran:

One of my favorite comments from Boston was Bain Capital’s Jeff Schwartz (P’16) was embrace your ignorance. It can be a valuable tool. Dream about how to solve problems. Live in the future, and build what is missing.

Jeffrey Mullen (Founder and CEO, Dynamics, Inc.) who is a legit freak of nature (lawyer, EE degree, patent holder, CEO, addicted gamer, nice guy) was around the question of singularity (will we live forever if we live to 2046, per Ray Kurzweil). “Sure, I checked it out- living forever is basically an engineering problem”. And you know, he’s the one person that I believe probably has.

Michael Holthouse former CEO of Paranet (sold to Sprint) added that the “plastics” of tomorrow may well be energy. How we make it, store it, and consume it will become vital to our future sustainability.

My favorite comment of the San Fran night from Seth Sternberg was on the makeup of founder teams: While he stressed the fact that Eng’s (his abbreviation) had to form the core of the product and it’s build, having a business guy that does the deals/money was also a healthy add. One point we all agreed on: avoid replicants. Having divergent points of view are key. Last point form the audience was this: consider how “geared” your co-founders are to start a business. It’s a long haul, with plenty of dips.

And, proud to say, Choate finally started to get its social groove on: the  LinkedIn group (now one of the school’s most active) has been full of good pointers, suggestions, and comments and a twitter feed (at this point twitter’s most inactive account , but getting better ) picked up steam in New York (this is a relative term- it’s a humble beginning. Check us out at #startupchoate

Soup to nuts, this whole thing came togehter in less than six weeks from the time Ron Fleury and Joe McAndrew posed the question: “what the hell do we do?”. And while Choate has been effusive in its praise and gracious with its thanks during this whole process (and tireless in its coordination), I attribute my contribution to nothing more than “doin’ what come naturally”. Hard as this may seem to some, it is really, truly all in a days work. Special praise also to our hosts at Connect Solutions in San Fran and Choate Hall (coincidence) in Boston. So now Choaties with start ups, who have a great network anyways, now have one on mobile, social and local to press the advantage.

Which is perhaps the greatest start up lesson of all: do what you love and your efforts can make a tremendous impact.

Panel at Choate Hall- great space!

Last week, when putting the final plans together for our Boston stop on the Start Up // Choate Roadshow, the bombs went off. And so we paused, briefly, to assess what it meant and what needed done.

The response that came back from our hosts and panelist pretty much sums up what make Boston unique, and what makes entrepreneurs special. While acknowledging the practicalities of navigating Boston after the bombing, the message came back loud and clear: events like this are what we do as start-ups and Americans. We’re undaunted builders of things. We cherish our freedom of thought, expression, and opportunity. It feels great, and we won’t quit. Let’s go.

And so, in a dense rainy night in Boston we had a great crowd of entrepreneurs on hand to listen to a great panel.

One of my favorite comments from Bain Capital’s Jeff Schwartz (P’16) was embrace your ignorance. It can be a valuable tool. Dream about how to solve problems. Live in the future, and build what is missing.

Jeffrey Mullen (Founder and CEO, Dynamics, Inc.) who is a legit freak of nature (lawyer, EE degree, patent holder, CEO, addicted gamer, nice guy) was around the question of singularity (will we live forever if we live to 2046, per Ray Kurzweil). “Sure, I checked it out- living forever is basically an engineering problem”. And you know, he’s the one person that I believe probably has.

Michael Holthouse former CEO of Paranet (sold to Sprint) added that the “plastics” of tomorrow may well be energy. How we make it, store it, and consume it will become vital to our future sustainability. 

So, I ‘ll remind those from Choate that are reading this (sorry, group closed otherwise)… We started a LinkedIn group (now one of the school’s most active) and a twitter feed (at this point twitter’s most inactive account , but getting better ) and planned a road show highlighting the best and brightest minds from the Choate universe of StartUps. We’ll do(ne) SanFran, Boston (last night), and New York (tonight).

So far,  while I think this will become a HUGE benefit for our alumni, it is actually our gift back to  Choate. It has long deserved a great start-up network. And for Choaties themselves, who have a great network anyways, this one is finally going on mobile, social and local to press the advantage.

Which seems entirely normal to me. Doesn’t it you?

Our Host, Sir Michael of Connect Solutions

San Fran was a great start last night: Woody and Seth really connected with the audience (Choate said it was a large turnout for these type events) and Michael Fitzpatrick ’93, CEO of Connect Solutions provided a great space.

By the way, check out the photo of Mike: that is what a preppy-techie-CEO-Dr.Evil-Englishman-Founder portrait should look like!

My favorite comment of the night from Seth was on the makeup of founder teams: While he stressed the fact that Eng’s (his abbreviation) had to form the core of the product and it’s build, having a business guy that does the deals/money was also a healthy add. One point we all agreed on: avoid replicants. Having diverghent points of view are key. Last point form the audience was this: consider how “geared” your co-founders are to start a business. It’s a long haul, with plenty of dips.

Woody had an interesting perspective on what skill he learned at Choate that helped him later. While one might think crisis management was the obvious answer, he actually stressed that the communication skills he learned there were the real gem. Being able to be concise and persuasive with arguments has helped enormously in his role as a minority investor.

And Joe’s introduction caught me by surprise: he referred to this as my brainchild, when all I really think of it as the most obvious thing to do: have networking events with good speakers and record the rest online for others to continue the conversation. But, I’ll take credit for it nonetheless.

So, I ‘ll remind those from Choate that are reasding this (sorry, group closed otherwise)… We started a LinkedIn group (now one of the school’s most active) and a twitter feed (at this point twitter’s most inactive account ) and planned a road show hilighting the best and brightest minds from the Choate universe of StartUps. We’ll do(ne) SanFran, Boston (tonight), and New York on successive nights.  Boston features Bain Capital’s Jeff Schwartz (P’16), Jeffrey Mullen (Founder and CEO, Dynamics, Inc.) and Michael Holthouse (Co-founder and President, Paranet, Inc.; Angel Investor)

So far,  while I think this will become a HUGE benefit for our alumni, it is actually our gift back to  Choate. It has long deserved a great start up network. And for for Choaties themselves, who have a great network anyways, this one is finally going on mobile, social and local to press the advantage.

Which seems entirely normal to me. Doesn’t it you?

See you on Linkedin and twitter guys…

We are kicking off a unique series in San Francisco tonight: Start Up// Choate.

I’ve long remarked how deep the empathy and how good the connections were grown from that school. For some reason the cycle of 10 o’clock curfews, dress codes in the dining halls, room inspections, and deans countering our late-night antics built an espirit among my co-combatants rarely duplicated in my 30 years since. We simply trust each other on another level. And most of us want the best for the school, despite the epic pranks we prosecuted during our time there.

So when I was asked what the School could do to keep up with its tremendous group of entrepreneur alumni, I suggested “do what normal people do”… umm normal to me. In the weeks that followed I’ve realized perhaps, when it comes to mobile, social and networking that I’m just not that normal. My wife reminds me of this regularly. We started a LinkedIn group (now one of the school’s most active) and a twitter feed (we’ll see how that works out) and planned a road show hilighting the best and brightest minds from the Choate universe of StartUps. We’ll do SanFran, Boston, and New York on successive nights beginning with TCV’s Woody Marshall ’86 and Meebo’s (now Google+’s) Seth Sternberg ’97.

Hopefully, we’ll learn about that process of entrepreneurship I have referred to as Discover, Develop, and Deliver.  Interestingly enough, while I think this will become a HUGE benefit for our almni, it is actually our gift back to  Choate. It has long deserved a great start up network. And for for Choaties themselves, who have a great network anyways, this one is finally going on mobile, social and local to press the advantage.

Which seems entirely normal to me. Doesn’t it you?

More from the event later.

360 respect for Someone that looks up to you

I recently read “On Raising Boys” and it brought out some very interesting points that I think apply to start-ups as well. One of the three key phases to development for a boy is having mentors in his teen years that are outside their main family unit, that have perspective, and come with authority in some field.  He can rely on this guidance to make important decisions outside of his direct family unit while building interdependence and confidence on his own.

Same goes for mentoring entrepreneurs.

I recently wrote about my mantra of Discover. Develop. Deliver. Which in very broad terms means I am always looking for young-at-heart entrepreneurs with fresh ideas. But equally important is the willingness to develop themselves  their product, the message, etc.

So here are some experiences I have drawn from mentoring lots of entrepreneurs over the years:

Know what you are mentoring to

Sounds crazy, but often the mentee does not know what they want out of the relationship. “Sounding board” is often the catchword for “ I need someone to talk to”. Rather than that generalization, I find I have always been more effective when we focus on a specialty need. It could be finances, business models, business development, partners, motivation, time management, you name it. But knowing what the mentee wants out of the relationship allows me to think on their behalf through the lens that they asked for guidance.

I don’t give personal advice when business advice is asked for- or vice versa.

I try to share my experience wherever possible. I tried this… I realized this…. I once had trouble with this… so that the entrepreneur can see things through another lens, and not be defensive about hearing “you should do this.. try this… break that. Entrepreneurs are tense enough; they don’t need an office parent telling them to eat their vegetables. I was reminded recently of one of my classics in this category: breakfast begins at 8. I work with so many younger entrepreneurs, who has a quite different idea of “bedtime” on “school-nights”. Rather than try to correct that behavior, I simply scheduled important meetings at 8am. They soon got the message that no matter what is done the night before, the bill is due in the morning. Here’s the link from Richard Dinan ‏ breakfast is at 8

And I try to help people discover the talents within themselves by asking questions. Lots of questions. Lots and lots of questions. Eventually, we run the table from vision to execution and are ready to make some bold decisions. Having what Covey called “the courage of our convictions” means all the available facts have been surfaced, and intelligent discussion held, and the best course chosen. It’s never a lock, but it sure helps to enter the rapids with some sort of thought out plan.

And, most importantly, I try to behave like someone whose opinion is often sought. That’s perhaps the most important lesson of all.

Work with a mentee that actually is coachable

Some mentees want window dressing: so-and-so is on my Advisory Board. Some want a sounding board, but have their minds made up anyways. Some are just lonely. To me, neither are a great use of mentor time.

The mentee that has a thirst to learn, a gift for presenting situations with options, a curiosity to experiment and learn gives the mentor a sense of usefulness that is so key. Good mentees have the elements of challenges or opportunities worked out in their minds, but often lack the confidence to make a decision or fear some blind spot they haven’t considered. Those are great examples of where mentoring can really help cut to the chase, or save some dead ends.

The biggest gift you can give someone is to beleive in themselves – AJ Joshi

If you are doing it to make everyone money, let everyone know. If you are doing it for charity, make sure it’s worth it.

 Ah yes, why do we do this. Mentors are rarely ever paid by the hour (though some coaches are, but I contend that is different). I mentor a lot of CEO’s and Founders where I own stock in the company and have quite a vested interest in their success. So by teaching them, I expect to add value to my position. Sometimes, the lessons actually shrink value in the short-term; but that’s why they are called lessons. The worst sin there is to repeat them. Good way to lose a mentor relationship.

But some mentor relationships are just plain charitable. While I have very little free time to take on non-commercial mentorships, sometimes I run across someone who I really believe in, and believe they could use my help. I guess the key point there is that both mentor and mentee know what the other is doing it for, and the ground rules are set and respected.

I’ve been told that time spent and value delivered does not necessarily correlate: you can do just about anything in two minutes… if you spent thirty years perfecting how to do it.