Miles To Go.

Smiling still: TY

Every once in a lifetime or so, someone like Tom Yankus comes along, sets his hand upon your shoulder and says “kid… fill in the blank”.

And it remains with you all through the years, etched in  corner of your mind, to be repeated and reused in all sorts of forks in the road of life. Of course, in my case, I acknowledged little of it for the first five years, and used only a little of it in the five that followed. But my journey has taken me a long way from Exit 14, and has more than a few decades of seasoning now. The advice seemed to settle in, the mentorship seemed to take on a new meaning, and I realized what a fine leader I had followed.

And the irony of course, is when you present something like this to TY, he invariably says “did I say that? – sounds like an afterthought!” And yet, I kept it with me for decades.

I’ve written a few pieces now on TY (here, and #2 here) but later this Spring, we will break ground on the new Ayers-Yankus Baseball shrine (news item), and I am proud to have been a part of the support that makes this possible (as can you, here). We likely all have our TY afterthoughts (add yours if you like in the comments below).

TY taught me many things while I was at Choate, but I learned them years after as I built and lead teams of 5 (many), 75, 105 and then 1,005 people. I remember one instance where I was managing a large and logistically challenging charity and having trouble balancing the need to get things done and the desire to  remain somewhat un-hated (for a summary of the breadth of the challenge, look at KFAC). I reached out to TY and asked about communication style, especially to large groups. His advice was to stay direct, but try to make them smile.

Wit makes it go down easier. One of the funniest expressions I ever heard from him was when we were debating the merits of one classmate who was off to a good start in his career, and had the attitude to match. TY cracked a classic, one perhaps he had been saving for years: ”He was born on third base and thinks he hit a triple.” I fell off my chair laughing.

Another story, which he will deny and I can’t prove after 30 years (these are the best kind) was when the honor roll was announced one spring in Chapel, and those on it were asked to stand. They did as each name was called, and they started making a lot of noise about it (especially if you were sitting down and not expecting your name to be called). TY’s hand went up, and the Chapel hushed. “Those of you standing for honor role, please remain so” he bellowed. “You’ve done great work here. But take a moment to stoop and shake the hand of one of the C students next to you. Because while they may not be standing now, they have had to learn the communication skills that will allow them to lead people like you the rest of your lives. Be friends”.

Needless to say, I was sitting so I did not fall off my chair. But I didn’t forget that either. And so in preparation for this announcement I spent a little time interviewing Tom (most of which ended up in my previous blogs). Here now are last nuggets from that conversation

MS: what were the best years for you? TY: Other than 1989 (marriage to Julie), 1990 (first daughter Anne arrives), and 1992 (second daughter Alex arrives), I loved my year in Navy flight school (1957) and my years in pro baseball (1956 and 1958).

MS: What is the compliment you most frequently get? TY: ”You look the same as when I had you in class. Don’t you ever get old?”

MS: What is your favorite word? TY: Empathy.

MS: What it your favorite quotation? TY ”An Alumni pulled me aside and said ‘You taught me how to write.’ That means more to me than anything else.”

Yes TY, perhaps it does.

Ride share with this gang?

I’ve been spending some time learning more about the sharing economy and some of its players. As an angel investor accustomed to clearly defined problems, grand solutions and natural revenue models, it seems like the beginning of the story. Kinda like a lot of people showing up in munchkin land- somewhat disoriented, terribly excited, not sure of the path forward.

Dorothy was pioneer when it came to couchsurfing (wimdu perhaps?), but she woke up in a terribly different world. She had to make snap judgments about people, and she had very little context to help (The Good Witch of the North notwithstanding). She was taking very real risks with herself, her dog, and her ruby slippers. But she had to rely on her wits: no help from web 2.0 and social media to help her make big decisions on risk  (one of the great segues of all time folks).

Nowadays, there are more ways to make an assessment about people. People vouch for each other on sites like LinkedIn, Honestly, and Connect.me. People accumulate likes and helpfuls from sites like TripAdvisor, Facebook and Yelp. And some products go further, combining those elements plus offline verification to develop multi-layers scores, like TrustCloud (I’m an investor). Through all these inputs, we have begun to infer things about people based on their actual behavior over time. Here’s how a well-designed trust solution might have helped with her key judgments:

1. The Scarecrow- great domain expertise and happy to assist. Probably a contributor to Yelp or TripAdvisor and frequently tagged helpful.
2. The TinMan- experienced and analytical, probably has people vouching for him like the static inputs of Honestly and Connect me
3. The Lion- I have this guy tagged as a reputation guy. Very proud and looking to clean up what people think of him. Uses Reputation.com a lot.
4. The Wizard- He’s all about influence, which means he spends most of this time on klout.
5. Dorothy- a teambuilder and leader. Probably destined for LinkedIn. But having trouble verifying place of residence!

The point is (and I have taken a veritable yellow brick road to get there) that we no longer live in Oz. There is real, relevant data out there that when properly gathered, weighted, and presented can really help the sharing economy navigate their challenges. (Here’s a great blog from Charles Greene on Trust). But no single point of reference and no rigid formula will serve the Trust needs of every community, let alone every situation.

This is a challenge and a journey that requires multiple layers, great heuristics, and the power of the network effect. (which is one super reason for all these layers to work together). I look forward to watching how this evolves, and who gets to the Emerald City first.

TY New Sign: speech is over!

Continued from Moneyball and TY #1… Choate will soon honor Baseball legend Tom Yankus in an as-yet-undisclosed grand gesture. But lifetime winning averages on the diamond are one thing. Winning averages over a lifetime are quite another. As Rod Serling once said, there were signs along the way.

So thirty years on, what I have learned is that the signs he gave us, and the strategies we executed, were actually great lessons in life.

One note: in an act of stunning simplicity and ultimate cunning, TY ”changed the signs” every year- to the same signs! From from 1958 to 2010! No one on another team ever stole, in spite of their simplicity, because no one would have been stupid enough to use the same ones every year. And as TY adds “We made them simple to be certain that OUR guys got them right!”

Here are a few of my favorites:

1. Thumb to chest was a Delayed steal. A unique move where the baserunner waits until the long after a normal stealer would take off, and then takes off. No-one alerts anyone of the steal, and the result is everyone on the opposing team yells at each other. No sweeter song than listening to that while standing on second base. The lesson was to Stay alert, you may catch them napping.
2. Red hankee out on the clipboard was a suicide squeeze. I loved the finality of it. We needed a run, and we had a guy on third. Everyone had to execute and it was a walk in the park: anyone chickens out and its an out, a double play, out a bat in the head. The lesson, of course, have confidence in yourself.
3. Arms Behind Back was a hit and run. It was a great way to get things moving, and take a chance when the upside is there. A missed sign here meant a sure out, but execution meant you could score from first. The lesson was to measure the risk against the upside (or downside)… and run like hell.
4. Hand to the Shin was a bunt. It was a way to get things started, to build a little momentum and confidence and perhaps manufacture a run. It taught me that Rome wasn’t built in a day, and taking it bit by bit was not a bad way to get things started. Particularly with younger ballplayers, getting a little confidence under the belt was key.
5. And finally, hands on hips meant, invariably, “kid, you still have a lot to LEARN”!

Did I have any clue that, as I took my lead off first and peered toward the Choate bench for TY’s next move, he was actually giving me signs I would use the rest of my life. The way I thought ahead, maybe so. Which would explain why I was picked off first once or twice, daydreaming. But, by and large I put the signs to good use. Still do.

Next: TY the interview:What did he kids teach teach the coach? And finally, likely, some details on what’s coming down on the honors front.

TY: Serving BP meatballs since 1958

MoneyBall got some Oscar nods recently; “Hollywood newcomer Brad Pitt may have finally arrived” quipped George Clooney from his Golden Globe podium. Meanwhile, another great baseball story 50 years in the making is now becoming an overnight sensation:  Choate legend Tom Yankus is due for some honors we can only mention once Choate’s PR cranks up, or the end of this series of blog posts, whichever comes first.

But first, here’s just a little bit about the why:

First off, my personal experience. I am one of a thousand or so athletes coached around the bases by TY. And the one thing that sticks with me is the comment I heard from my College coach after my first day on the field there: ”one of the best coached players around”. I shrugged, as I knew I was pretty normal coming from where I did.  It had very little to do with me, and everything to do with the coaching. Imagine the impact of good fundamentals and leadership lessons when multiplied by a thousand.

But the legend began way before the coaching started. Most of these Legend of Yankus facts have been verified, or the statute of limitations on appeal have long since expired:

• He visited Choate’s Winter Ex to watch the Boston Braves’ spring training in 1943, borrowing a jersey for later use because he wanted “to feel the glow.”
• In his Fifth Form year he won the junior varsity baseball award for outstanding improvement.
• After graduating in 1952, TY attended Williams College where he played varsity baseball, for which he has since been named to the Williams College All-Time Baseball Team.  
• TY was at Yankee Stadium in the summer of 1956 trying our and searched around the changing room for a blue sweatshirt, having not brought anything of the sort. Seeing him looking around, Mickey Mantle said, “Here, kid,” and gave Yankus his own sweatshirt, with the number seven embroidered in it. That year, Mickey Mantle went on to win the Triple Crown and the World Series. Now word on the shirt’s whereabouts.
•  Yankus signed with the Yankees and began a minor league career with the Missoula, Montana Timberjacks of the Class C Pioneer League. He later wrote a book, Montana Summer, published in 2000, about his experience in the minors. Turns out, he was pretty good with a double clutch on the team bus. Slider, maybe not so much.
• He pitched for teams such as Harwich and New Orleans in the Cape Cod Baseball League and later managed the Orleans Cardinals for nine years. 
• TY had been around Wallingfrd for a long time and at Mem house, most 3rd formers thought the New York Yankees were NAMED AFTER YANKUS!
• During his coaching career outside of Choate, he helped several players join the major leagues, including Aaron Boone, Todd Helton, Nomar Garciaparra and Frank Thomas. At Choate, Yankus coached Chris Denorfia ’98, who currently plays left field for the San Diego Padres. He has also sent numerous Choate baseball players to Division I colleges, such as Princeton, Harvard, Yale, Dartmouth, Columbia, and Duke.
• After forty-five seasons as head coach of varsity baseball, Coach Yankus heads to the locker room with 503 wins, 288 losses, and 11 ties, giving him a .627 winning average.

But lifetime winning averages on the diamond are one thing. Winning averages over a lifetime are quite another. As Rod Serling once said, there were signs along the way. Next: TY’s favorite signs for baseball- and life!

Janet Lee; nine ball machine

I once beat Janet Lee, the famous black widow, at nine ball in a giant exhibition. * **

While you’ll have to read to the bottom for the whole truth, let me at least  explain partially: it was excellent training for starting and growing  companies. Really. Here is what I used over the next 20 years from what I learned in  that one game:

The crowd is mostly noise: forget about them. So many startups  compete in crowded fields, with others releasing news and versions day after  day. While it’s good to be in tune, an entrepreneur has to be about supreme  focus on the task at hand. Nothing else matters.

The break sets it all up- that’s the team and launch. The entire DNA  of the table emerges with the first big shot- the break. Same goes for the  launch in entrepreneurs. Get it right and give it your all. Otherwise, the table  is a mess and takes more effort to clean up.

Know the speed of the table- market. Nothing ruins a well  executed shot than a misread of the felt. Rollers become bouncers, or never  make it to the pocket. You have to know how fast a surface you are playing on,  in either game.

Miracle shots also come with consequences. It’s amazing how  many wild triple bank shots present themselves in any nine ball game. But they  are low percentage shots. Worse still, they may leave your opponent an easy angle to finish you off, then and there. Calculate the odds, both of the shot,  and of the consequences.

Momentum is real. Make a bank shot, a lefty and a combo and you begin to feel you are invincible. You see the table with possibility, and your stroke has a confidence that could achieve anything. It feeds on itself, and it is certainly picked up by your opponent.

Think ahead: making the 3 ball does not mean you are in position for the 4. Ah, yes, the essence of nine ball is actually the next shot. Players and entrepreneurs both have to look down the table at what could be, and how their next move positions them.

Don’t think ahead too much: getting a good leave for the 4 ball only counts if you sink the 3 ball. And the reverse corollary to the rule above is: think longer term, but don[t forget to execute on the little things right before you. Otherwise, there will be no next shot.

Nothing counts as much as the last ball: run eight in a row and scratch and you lose anyways. Funny how people can stroke smoothly and confidently on 1-8 and suddenly look twice at an easy 9 ball shot. Miss and the opponent suddenly has you over a barrel in a way uncommon to the previous 8 shots. For entrepreneurs, this might be analogous to the exit: blow that and  it’s a re-rack, plus probably a waste of several of your best years.

Be a creative problem solver: there are more than one ways  to sink the shot. My game really improved when I began playing on several  levels, mostly to include banks, combos and the occasional jumper shot. But  basically, this is looking at a set of circumstances (the balls and their table  position) and figuring out the best shot for your abilities and for the odds of  leaving nothing good for your opponent. I also shoot left and righty (which  most people don’t know and makes me good money on side bets). And the  last comment is likely safe because pool players don’t read many blogs!

Don’t confuse luck and skill. I had a little of the latter, and for a moment a ton of the former. In any case, don’t stay too long at any table. Knowing when to walk is a life saver.

Shake hands and be a gentleman, win or lose. Perhaps most  importantly, the handshake acknowledges that you won or lost fair and square,  and were a sportsman throughout. This plays equally in nine ball and  entrepreneurship. Get used to it; you are going to lose a few. Handle yourself  with dignity and learn a few lessons for the next game.

*And now, the technicalities: Janet Lee was hosting the Brunswick table at  the Chicago Housewares show at McCormick Center, in the mid 90′s which is a large exhibition  hall (ok, everyone else was there for blenders and hooks!). The fact I was walking the floor looking for companies (and  eventually found a deal I did there) should not get in the way of a good story. I have lots of bizarre analogies, this is but one.

**She challenged me to ONE GAME and sank a  ball on the break. She sank two more before trying a two-banker, perhaps  playing to the crowd. In my finest nine ball moment, I sank the next six  including the 9 ball for the win. She has gone on to tremendous success as a  touring pro, and wants to learn about digital media. Knowing the odds were long  I ever would beat her in any rack again as long as I lived, I retired from  competitive nine ball that afternoon and used the lessons for angel investing  and creating businesses.

Join me in liking Janet Lee on Facebook and Twitter and thanking her for all she has done for  start-ups!

Mobile Global: Click 2 see cool pic

I work hard to get lucky.

1. The Carriers used to think they were content curators. Seriously, there was no other way to get distribution than to program in bizarre carrier languages (BREW, etc) and pay them through the nose to be “on deck”. Hey, they got the idea from the old AOL days. But these people did not realize the comic effect of managing content on a 2″x2″ screen. Plenty of money was wasted getting on those decks, and getting the content optimized. At one point, I counted an easy $500MM of venture money was poured down that rabbit hole.
2. Eyeballs began to shift. First it was getting email and text on phones. Then a few games and stock quotes. But the iPhone and its 250,000 apps out the gate brought all manner of information and entertainment to the mobile screen. The PC reached a plateau.
3. People were no more willing to pay for apps than they were to pay for the “old fashioned” internet. It should be free, man continued as the digital credo. And except for very few exceptions (iTunes being one), the entire mobile revolution has been driven to date with ads.
4. Tablets followed shortly, and guess what: they’re mobile too. Meaning all the ad serving technology, all the geo-location and device data was much more like a mobile phone than a PC.

With a little knowledge as an angel/board member with digital yield optimizer operative (now Operative One) and some domain expertise from Cellufun, I went on to start mobile ad network/ad server Mojiva with co-founders Krish and Dan.  And I have since been founding angel in mobile powered projects like MyBailiwick (crowdsourcing too early!), TrustCloud (trust in the sharing economy getting hotter now) and WellAware (mobile health and wellness platform). I think my bets in mobile media have been pretty lucky, and i will continue to make them for all the basic reasons above (and many more that are regularly laid out by tech guru Mary Meeker).

I just never knew where the tipping point was.

I do now. High five.

"Play responsibly"

I’ve been trading everyday phone calls and emails with the developer that built our new family home. The experience hasn’t been perfect, from my perspective, but I acknowledge the guy probably has plenty other things going on besides the faulty control panel on my Kohler steambath.

Turns out, I was right.

Seems Brandon won the Connecticut Powerball lottery earlier this month, and it all came out today. For those that don’t know it, our new nhometown of Greenwich does not see a lot of suffering. In fact, if there was ever a town that did not need a lottery winner, that would be ours. If there is an Occupy Greenwich Avenue movement starting soon to decry the inequality of the 1% winning a lottery designed for the 99%, consider this: the town is full of rags to riches stories. It’s just that they usually involve numbers that come through a Bloomberg terminal, not spit out for a dollar at the local BP station. Luck is random, and this proves it, again.

But the BP station is where Brandon and his two boyhood buddies went in equal (I surmise) on a dollar bet that pulled a lump sum of $100,000,000. (Powerball markets it as $254,000,000 but that’s a 30 year payout into a black hole of tax policy no one in or out of Greenwich should take a bet on). I was recently told by an EO leadership swami that you can’t control the world, you can only control how you react to it. This is a good example of that.

He has been sitting on this news for the past three weeks. In the meantime, he has been responsive and professional about the various punchlist fixes he owes at the house. We knock something out every few days. And that says a lot about Brandon; old school, honest and possessing a genuinely good heart. I spend a lot of time thinking about Trust, and have written about the Heuristics of Trust , actually more than once. I’m not sure who bought the ticket, but the fact the three shared it also says a lot about their Huck-Finn like trust dynamic ($.66 would have bought out the others a few weeks back).

Today, they came clean and told the public. They had formed a trust, and will give a large amount to charity. They don’t strike me as the type of guys about to go on a race to the bottom and be deeply in debt 5 years after winning. It will probably not change their lives all that much, but that’s an outside view at this point. All I can say is, it has not changed my friend in the past three weeks.

That is a good story. Good on you mate.

PT Barnum would have been proud

I was heartbroken this week as news that the wedding of the century lasted 72 days… Actually, what brought tears to my eyes was that the American public took yet another collective step down the ladder in race to the bottom, and this particular bottom is a big one, if that shot from the New York Post isn’t retouched!

How does anyone assemble such a large group of lazy, nihilist, shallow, hopeless aspirationalists and suck them into actually believing that shallow self-absorbed and dumb as a clogheel is any way to go through life (to quote Judge Smails from Bushwood CC). Oh, and all the while selling them products and services that redefine trashy?

1. Turn on a camera I guess.

P.T Barnum may have said “sell to the masses, eat with the classes… the Kardashian Empire has somehow gotten Americans to consume endless hours of totally worthless pettiness, appears to be selling them fairly lame clothing (with what is best described as VS syndrome it looked so good on her…), and almost loading all those follower/purchasers into a ridiculous fee loaded credit card. That was finally pulled, as the smell from the fees and interest must have even penetrated the perfumed confines of the Dash boudoir. It seems no one every got poor underestimating the class of the American people.

So truth be told, I don’t mind Kim. She’s pretty. And she is not the first to run the table in the star-infatuation for profit racket.

Elizabeth Taylor carried that type of fascination factor throughout her live, and was no stranger to quickie marriages and headline grabbing affairs. But she actually DID stuff. Decent movies. Ardent support of AIDS victims. Classy as hell fashion. And articulate positions on a variety of issues that concerned our society. On the other side of the spectrum of nothingness, there is Paris Hilton, who is furious she can’t muscle onto a magazine cover lately, having contributed equally as much to society’s table as Kim, to date.

Kim has become the most extreme symbol, so far, in just how low and desperate America’s aspirations are for something better, and how totally devoid too many Americans are these days of the skills and work ethic required to actually earn any of it. That’s the saddest part of this progression, and it won’t stop until we find something better to do with our time. Like developing a skill, or creating something that benefits society, our community, or just a circle of friends. And it will take tuning the crap out of our lives and getting on with something more rewarding and redeeming.

And what’s next for Kim and the value of the throne as Queen of Nothingness? Perhaps the best answer came during lunch with Sam Zell yesterday while he talked about distressed assets: price is the cure for any perceived defect.

Sponsorship for her next wedding, or a ringside seat at the birth of her as-yet-un-announced secret love baby (no doubt conceived during an yet-to-be announced affair while married to her now belatedly-beloved for 72 days) may well fetch less that $17M. How much less and how quickly her price falls depends on how soon America snaps out of it, and moves on to something with meaning.

I’m counting on that happening, but not fast enough.

The Kardashians next season begins November 27th. Plans for her run for the Senate are as yet un-announced…