< 140 Leadership Primer

If something doesn’t feel like leadership, it’s not.

Leadership is the most overused term in business. Few know what it looks like.

Imagine explaining a leadership concept to your grandfather. If you see him looking sceptical, so should you.

Reading books about leadership is an infinitely less valuable exercise than reading books about lives well-lived.

If a leadership concept doesn’t fit the world, it won’t fit your home either.

A true leader rarely thinks about the term “leadership.”

Leadership is always about empathy, never about tolerance.

Leaders walk the walk and guide others in doing so. Leadership without teaching is hollow.

Leadership is thought plus action, never thought alone.

Look for leadership outside of your comfort zone. Understanding leadership in different contexts is key.

There are no negative leadership lessons. Seeing how not to lead is a remarkable gift.

There is no leadership without reflection and meditation. A leader knows how to find their center.

Leadership needs to be communicated virally.

Leadership can be learned by and from people of all ages. We are never too young or old.

False praise is to leadership what arsenic is to a soup recipe.

Leadership is not a contest.

Leadership is iteration plus awareness.

Ego is leadership kryptonite.

Leadership is never a final document. It is an ongoing series of rough drafts.

Pack Like a Champ

Okay. A quick and fun little post as I sit at ORD waiting for my very early morning flight to SFO.

I’ve traveled two MILLION miles with carry-ons. It’s not as difficult as you think, though I did kind of bend the rules a bit in the old days.

When I used to need to “dress up” (thankfully, with my work now, I wear whatever I want, whenever I want) I had several home bases around the world. So I’d store clothes there. When I arrived in Beijing, for example, my hotel room closet would magically have my freshly-pressed suits and clean shirts, dress shoes shiny as a pretty penny.

That was pretty cool.

And on those trips, I’d really have only my brief bag and dopp kit. That’s it.

But I also did a 70 day business trip carry-on only. Lessons from that trip resonate today:

- You can replenish things (including, say, socks) when you’re on the road.

- Not everything that left with you needs to come home.

- Quick-dry clothes (Nike’s dri-fit totally rules) save the day.

- Your carry-on needs to be the perfect balance of light and indestructible. Err on the side of indestructible.

- While wheeled luggage is great, hard-sided cases are not the way to go. You need soft ballistic nylon (I use a no-longer made Timbuk2) that accommodates jamming in extra stuff.

Here’s the issue: Assuming that you’re staying places where laundry isn’t an issue, how much do you REALLY need to bring?

I can go a couple of months on the road with:

- 3 pair of pants. Quick drying is best, but I don’t follow that rule. I like jeans and khakis as soft as puppy fur.

- A variety of 5 shirts.

- Quick drying personal garments. Tilley Endurables make stuff that dries in minutes.

- Layers for warmth. Again, I swear by Nike Dri-fit. Their full- and half-zip tops take no room, cut the cold and wind and can dry in an hour.

- Workout gear. I’m partial to Ralph Lauren’s quick-drying RLX line. Great gym shorts.

If you DO need a business jacket, the aforementioned Tilley Endurables make a great travel blazer. I had one and beat the crap out of it. You can roll it into a ball, use it as a pillow on your flight, hang it in your bathroom, turn on the hot water and, voila, no wrinkles. Amazing. And it looks like a real blazer – it has structure and style.

Sometimes it’s best to wash your own stuff rather than send it to the laundry, especially when what they charge to wash your pants is more than the pants cost. Here’s my how-to:

You take what needs to be washed into the shower with you. After you’re clean, You pulverize the clothes with liquid soap and very hot water. Don’t be shy. Ring it all out well. Place on the floor in a thick towel. Roll up with towel with a piece of clothing in it. Walk all over said towel (jumping is cool too, as is doing the Mambo), thereby extracting water from the garment. Hang or lay the garment. You’re soon good to go, friend.

Never put damp clothes in your bag. Even after a short flight, the stench is amazing. It will ruin your bag (R.I.P. lovely old Tumi).

As for shoes, I’m a sneakerhound, as you know. And I work out a lot. So, I wear one pair and pack another.

And that’s all. It’s totally do-able and you can have a variety of clothes. Just remember that very thin is always better than thick. Always err on the side of bringing a bit too little. You can always pick up something you need when you’re there.

And enjoy your trip

How to Build Anything From Scratch

Yeah. ANYTHING.

It’s simple: just learn to deal with the fear of starting from zero. And, to help you out, I have the perfect training tool:

Snakes and Ladders

Yes. THAT Snakes and Ladders.

You remember the game. You roll the dice, move your piece and head up the levels of the game board. If you land on a ladder, you move up to where the ladder ends. If you hit a snake, you slide down to where it takes you.

Basically, like working with any startup in the world.

The beauty of the game is that it sucks you in. Things appear to be going so smoothly. You’re 10, 15, 20 places ahead of the competition. Then…ssssssssssssliiiiiide (insert snake sound here, please). You’re 18 behind. And then they hit a snake and all of a sudden you’re even again.

But part of the fun of the game isn’t that you’re once again tied, it’s that you thought the game was about to end and, instead, you’re both only on number 22 instead of 71.

It’s frustrating. But it’s good practice for starting anything from scratch.

I really like to cook. And my favorite thing is to take a pot, fill it with some water, and create some kind of Asian fusion soup. What I love most about the process is just that – staring at a pot with water heating up in it and thinking about what I’m going to pull out of the fridge and cupboard over the next few minutes to make it not only consumable, but, ideally, something I’m proud of.

So I’ll take a little miso paste from the fridge, some rice noodles, peanut sauce, seaweed, some kale, spring onion, maybe some lemongrass, even add a little green tea if I’ve brewed some. Maybe some sliced fish cake, a little of the salmon roe I always keep in the freezer, maybe some Malaysian curry paste and then I let it simmer.

Sometimes, for a variety of reasons, what I end up with isn’t great. And sometimes it’s stunningly good and while I’m tempted to record on paper what I just did, I never do. It’s about the art of the invention. Next time I want to make something even more delicious and I want to do it by really testing the elasticity of my ingredients. I want to try a new mix of parts to make an even more innovative whole. I’m no longer afraid of how the pot looks when it only has water in it.

I spent most of yesterday moving from a blank Keynote on my iPad to, about 14 hours and four NFL and NHL games later, a really decent deck for something brand new. The feedback this morning on what I created was strong. I feel good about what I did and how I did it. I want to do it again because the feeling of getting in front of the idea that you’ll never again create anything of value is amazing. And the way for you to experience that is to, again and again, stand in front of that empty pot, that blank screen, and make it happen. That’s how to build anything from scratch. Be prepared for the snakes and ladders and the days you forget how salty salt actually is and ruin the broth. You can always start again but you can’t start again unless you start the first time.

As always, rock on, my friends.

Be

Let yourself BE in 2012.  Please, just let who you are shine through next year.

I don’t want you to make any New Year’s Resolutions aside from this one: “I will allow myself to BE.” By allowing yourself to be, you will allow yourself to become.

That’s it. Its beauty is in its simplicity. When you stop being the one who not only builds but actually (and kind of insanely, when you think about it) guards the roadblocks in your life, you’ll be opening the avenues to a new world.

I know. I don’t usually write about things like this. I am avowedly not in the mold of the self-help gurus you can see at 2am on a bad cable channel. But this is immensely important stuff and I implore you to consider this today, before your airwaves fill with Resolutionmania.

I had a conversation the other night about gyms. You know when gyms are the most full? Right after New Year’s. Know when they empty out? A month later. The reason is simple: when someone sets a personal policy such as “I will go to work out at the gym every day,” and the starting point was a fully sedentary life, it’s a prescription for failure. It’s simply not a resolution that’s going to be met, for a variety of reasons.

What I’m advocating here is permission to just be. If you want to be more healthy, allow yourself to be. These are affirmative choices. It’s not about schedule or routine or the insanity that comes with padlocking pantries and painful deprivation. Just open a door every day on the path to your goal.

So maybe the first thing is to develop a taste for an Americano instead of your usual latte. You think “Wow – I love the coffee flavor and it’s a different thing without the milkiness.” And since you drink two small lattes a day now, you end up saving 500 calories a day which will, just given the math, result in a one-pound weight loss a week. By doing nothing but exploring a new taste. It’s about discovery, not deprivation.

Here’s another simple one: many people tend to shy away from walking during their workday for a simple reason: the shoes they wear to work are very uncomfortable to walk in. We’ve all had new shoes and ended up creating a makeshift band-aid triage unit just so we could walk from the train to our offices.

Well it’s 2012 in a few days. There are tons of great walking shoes disguised as dress shoes, for women as well as men. I can tell you that I used to walk tens of thousands of miles around the world in Ecco Danish dress shoes. They’re not expensive, they look as good as any conservative dress shoe, and it’s like walking in a pair of sneakers. Cole-Haan, in fact, makes an entire line of dress shoes for men and women with Nike Air technology. They’re so comfortable, you’ll find yourself slipping into them on weekends.

The point being, of course, that if you’re comfortable walking, you’re inclined to walk more. It becomes something that you can just do more of rather than a painful chore.

Back to my gym example for a sec – know a major reason why so many people new to a gym quit? It’s the bikes. Seriously. They’re not used to riding, then they sit on stationary bikes (assuming that they’re easier than any of the other cardio machines) and within days they’re in constant pain because of how uncomfortable the seats are. That dull throbbing when they walk turns them off the gym altogether.

“Okay, so we’re feeling somewhat warm and fuzzy now. Aren’t you going to talk about innovation, as you almost always do?”

Yep. Here comes:

Let this attitude carry over to your relationship with ideas.

By far, our biggest obstacle in the realm of innovation is ourselves. I see this every day in my work. We’re afraid to give our ideas the oxygen they need to survive.  We’re scared of failure and, If we’re being open and honest, we’re more scared of success. Too many ideas die well before iteration. We kill them out of fear.

So, following this model, find ways to discover your ideas. Buy a nice notebook or (I prefer these) big artist’s pad and start to write and draw out what you’re thinking. Collaborate. Share your idea with people who can help. Get on my radar if you think that might make sense – I’m happy to talk with you and point you in the right direction. Tell your fear that having a few sets of eyes and ears on your idea is just a way to stretch your creative muscles a bit. It’s not about an endgame, it’s about learning.

Don’t forbid yourself what you used to see as a luxury of time. Your ideas are a part of you and they deserve your attention. No matter how you need to do it, gift yourself that time and focus to play with your ideas. Test their elasticity. See how they fly and, more importantly, in what direction they bounce when they hit a wall.

Play with this idea of letting yourself BE as a resolution substitute. Resolve not to resolve and let 2012 be the best year you’ve ever had.

Slow Information

2011 was the year of information. It seeped into our consciousness over the year, this idea that the volume of information now available in the world truly was overwhelming.

Fifteen years ago, few people used the Internet. Not many used email and even if you actually did, you couldn’t assume that even a small fraction of the people you knew did. So it had little currency.

Today we live in a state of daily information overload. But, I would argue, the fundamental problem remains, that of finding meaning and relevance.

When I was a kid, I was taught how to search for information. It was a slow process, involving travel to a library, index cards, often asking a person for help. And the information available to me was just the information available to me. If it wasn’t physically where I was, then I couldn’t have it.

I could ask others for help, and in so doing, I’d have access to the information to which they has access. So my reach was now wider. And they might consult with someone on my behalf, for another plus one.

Surely this was slow and as certainly this was labor-intensive. But I’m going to argue that in some ways it was superior than what we often do today.

When we did first-hand research then broaden our search by consulting others, there was a legitimacy to the process. I remember doing a research project as a kid on zoos. Aside from some primary library research, we had to talk to people who worked at zoos. We gathered first-hand accounts and perspectives. While the volume of information we collected paled in comparison to what we get today, it was deep and
robust.

Now we have instant access. From almost anywhere in the world, we can immediately find information on devices that, in 1995, made only phone calls and that very few people had. As the devices that are the conduits of information became ubiquitous, the volume quickly ramped up. Just the other day I read that the amount of information an elementary school student can access in a day eclipses that to which a
fine scholar would have had access in a lifetime less than a century ago. Phrased in this way, I envision a toddler holding a gun that can down elephants.

So if 2011 was the year of information, I think that 2012 will be the year of transparency. The true currency of information is trust. In my research example from when I was a kid, I trusted the librarians, the encyclopedia, and the people I spoke to who worked at the zoo. After all, if you want to know what it’s like to work at a zoo, isn’t it a
better idea to ask someone who does rather than enter a “query” into a “search engine?”

How many university student would you guess consult online resources when they’re considering entering a profession? I would guess a massive percentage. They go online and learn about, say, different specializations in the Law, what new associates earn at a set of firms they choose to plug into their search. There’s a lot of data online and they do a diligent job in diving into it.

How many do you think arrange in-person meetings with several lawyers? How many ask questions in person like “Are you a happy person?” “If you had to do it again, would you become a lawyer?” It’s not just asking the question (sure, that can be done online), it’s about the intimacy of the research, the reception of indepth emotion and nuance that one can only get in person. It’s about a trust that happens when said experienced lawyer whispers “Honestly, the just isn’t for me. I’m stuck and I’d love to get out. And here’s why…”

2012 will be a year where the value of information finally seeps into the public consciousness. The conversation will become about not only what we know but how we know that what we know is meaningful. We will shift from an orientation of quantity to one of quality. It’s not that we won’t use the Internet, it’s not that Google will disappear – of course not.

I like to think of it as Slow Information.

Just as the Slow Food movement brought a shift in perspective to how we thought about food and eating (and how we gathered food, and where and why), Slow Information (an elegant counterpoint, I would argue, to the hyperfastness of information today) is about meaning and meaning is currency.

What’s a Startup?

I’m seriously sick of getting into arguments, all over the world, really, about what the hell a startup is.

A startup is ANY newly-created company or, if you want to get more technical, one with a relatively limited operational history. Yeah, actually, that’s the definition of startup.

People almost never use the term “tech startup” anymore, which is a shame, because the massive number of startups in this space has resulted in tech startups taking ownership over the entire nomenclature. But, and this is entire reason I’m writing this piece, it’s ESSENTIAL to understand that while tech startups are absolutely startups, so are newly-created businesses that aren’t in the tech space. Seems like a no-brainer to me but I’m often standing in the wilderness on this.

See, here’s the thing. I love tech and I love educational technology (“EdTech”) and all of the other forms of tech. But we’ve somehow lost the thread. We’ve become yobongoed.

Hah? “yobongoed?”

So, yesterday I saw a commercial for a tech startup called yobongo, currently in development or perhaps dead (a little difficult to ascertain at the moment). Here’s the video, in case you’re so inclined:

yobongo (click on it, silly)

I’m sorry but this video pushed me right over the edge and it does so for three key reasons:

1. Stop. Just stop using your big, fertile brains to create another messaging service when you could be creating socially useful shit. For the love of God, stop. How many messaging services are enough? I don’t want to know exactly where everyone I know is at all times and I as sure don’t need to be tracked more than I’m sure I already am. Plus, um, hasn’t this been done before. What the hell is Glympse? Yammer does pieces of it. Even INSTAGRAM does if you use it in that way. Seriously.

2. The video itself is just abysmal. Seriously, this is the worst piece of shit I’ve seen in ages, partly because of the next point.

3. Enough hipsters already. Come ON. First, the video was clearly shot in insanely hipstery Dolores Park and the even mas hipsterific Summit SF cafe. The level of inventiveness in this is a flat zero. My brain hurts with the entire concept. I can just smell the soy latte and ironic monotone whining.

Oddly, this wasn’t a tangent. This is the shit people see in their minds when they think “startup.” It’s seared into our consciousness with the hot, red branding iron of mediocrity.

Look, I work in and with a bunch of startups. I love to advise them and the entrepreneurs who fuel their progress. And while tech is a part of most startups today, where tech is in and of itself the beginning and end, my concentration is strained. Throw in terms like “social” and “messaging” and the ubiquitous “the next Facebook” and I’m measuring the potential bodily damaging from flinging myself over whatever is closest.

What I want to see for 2012 is a much broader realization that anyone looking to open a great new business is opening a startup. I want to see incubators for non-tech startups. I want to see more EDUpreneurs use tech as a tool rather than as the entire engine. I want more talent following what I try to do, which is to identify amazing people with great drive and energy and leadership and for us to use our time and talents to support them. I want to see people passionate about making truly exceptional, world-changing shit rather than getting all bouncy over how to monetize something they haven’t a clue how to build out. I really just want to see ALL good startups have a chance to succeed and I want us to call out stupid ideas and copycat shit and put a bullet in the base of the skull of a lot more rip-off, intellectually complacent, fluffy ideas.

And I want world peace, of course.

And onion rings.

Pop Everything Up

It was late 2007 and I was sitting in the Presidential Suite that was my insanely ridiculous upgrade at the Sofitel Wanda Beijing, a place I pretty much called home for the better part of three years. I had a big paper photocopy of a map of the world and I was drawing on it in permanent green marker my plan to create a massive pop-up school.

Why, I reasoned, could I not open a school brand in China for Chinese kids and then build a series of global relationships all over the world so that these high school kids could study in other countries. So instead of building what had become known as a (very one-way) Golden Bridge to the West, where kids would go from China to, say, one boarding school in the UK or US, I wanted to build something more akin to an Interstate highway with lots of interesting exits. One in Stockholm, Buenos Aires, Montreal, London, Amsterdam, and so many more. I was actually reasonably close to securing the last bit of financing to build this brand when the market crashed and the earthquake hit (our Chinese home base was going to be in my beloved Chengdu, Sichuan Province).

Flash forward to a year later when I had the great good fortune to meet the amazing Founder of THINK Global School and we worked together to build the most unique high school in the world and, indeed, the first pop-up school. Students at THINK Global School travel the world and study in three international cities each year. Essentially, each city is a perfect pop-up, in that a relationship is developed with a host school, students and faculty engage with the local community for a trimester of an academic year, then the school moves to the next city. There’s always a new challenge ahead. Boredom isn’t on the menu.

I actually saw my first pop-up store in Hong Kong. It was a very temporary set-up of a fairly ethereal French brand, testing the market before making the huge investment in permanent space on Hong Kong Island. I was immediately taken by how rough the store looked with unfinished wood, temporary tables, and a variety of shelves and hangers. But the idea was a massive success and the brand established itself all over Asia because of its pop-up success.

Here’s the beauty of the pop-up concept: its value proposition is in its impermanence.

Just recently, Seiko watches (one of my favorites – I’m a sucker for their Japan-only high end stuff) made a big investment and opened a boutique on Toronto’s very expensive Bloor Street. It was ill-advised, as Toronto doesn’t have a big Japanese watch culture and there was no way that they would sell anywhere near enough watches, over the long run, to break even. The day the boutique opened, I thought “Why not just do a pop-up for a month? Bring your coolest stuff, set up a pop-up in any one of a few perfectly appropriate spots, message it broadly, then get out of Dodge?” The boutique closed a few months after opening, losing plenty of cash in the highest rent area of Toronto.

Impermanence brings interest.

I’ve recently advised three clients/potential clients to make a new position they’re hiring for a closed-ended one. As counter-intuitive as it may seem, there can be a huge benefit in making a job pop-up instead of permanent, whatever that means in the world of work today. If you’re trailblazing something really unique or maybe doing something that’s a fixer-upper, why not realize right off the bat that the relationship will have an organic cycle? There will be a honeymoon with lots of high fives, then some peaks and valleys, then both sides are going to get sick of each other. The pre-ordained end can actually be a brilliant feature.

I’ll tell you what I want to see right now, in very superficial things. I would love a Dean and Deluca gourmet shop pop-up in Toronto. I even know some amazing spots they could drop it. Come for eight weeks, kick some ass, make a pile of cash and split.

I want to see a Mos Burger pop-up in Toronto. It’s a Japanese burger joint that’s like the tastiest fast food ever. I’ll personally eat enough over your eight weeks in Toronto to make it worth your while, and I’ll turn on some serious influencers to join me (Saul Colt – you’ll lose your mind over Mos Burger).

Finally, I want to see Onitsuka Tiger do a pop-up in Toronto. Bring the rare stuff, some of things I only see in Tokyo. Toronto can afford your crazy expensive shoes and pieces of fun and style. Just bring it and you’ll be tempted not to leave. But do. Then come back and surprise us.

I want you to think about the things that you see around as permanent and think about them as potential pop-ups. Let yourself imagine what it might look and feel like and, if you’ve never been to a pop-up store, find one in your city.

And the Damage Done

In the prologue to “The Needle and the Damage Done,” Live at Massey Hall (right here in Toronto, where I’m writing this today), Neil Young talked about how his generation lost so much talent to hard drugs. Then he sang one of the most visceral songs I’ve ever heard:

I caught you knockin’
at my cellar door
I love you, baby,
can I have some more
Ooh, ooh, the damage done.

I hit the city and
I lost my band
I watched the needle
take another man
Gone, gone, the damage done.

I sing the song
because I love the man
I know that some
of you don’t understand
Milk-blood
to keep from running out.

I’ve seen the needle
and the damage done
A little part of it in everyone
But every junkie’s
like a settin’ sun.

Twenty-one lines of poetry, a song that lasts two minutes and eighteen seconds, and Neil Young created one of the most powerful songs of his generation.

I see far too many people who don’t take care of themselves. They have the means to do so, they just fall prey to whatever real or metaphorical needle they can’t get around.

There are always hard things to focus on in our personal and professional lives. And there are times where, for many, it’s beyond challenging to find a glass half or even one-tenth full. But I’ve always been a huge believer that as long as there’s time left on the clock, the game’s still on. In sport and in life, I’ve witnessed magnificent comebacks and been blessed enough to have a hand in a few.

Sometimes at night when I can’t fall back asleep (who knows why – often it’s because it’s the middle of the night and my body clock knows I need to wake up at 4am for a call to or from Asia) I think of one of these comebacks. As I’ve written more than once, I played some football as a kid. One season, I was the quarterback of a particularly bad team (who had a particularly inconsistent and kind of whiny quarterback) that went 1-7 in our first eight games.

On this particular game, we played perfectly. We made no mistakes – either in act or omission – yet we found ourselves down 17-13 with less than two minutes to play. I don’t think that I led the team down the field because, to this day, I remember their excellence – they definitely led me all the way to the opposing 22-yard line. With time becoming a huge issue, I rolled left to pass, saw nothing and headed as quickly as I could for the sideline and a two-yard gain. I almost made it before this bullet of a linebacker accelerated the end of the play and the emptying of air in my lungs. The sun was definitely setting.

Last play of the game ahead, I knew exactly over whose left shoulder I needed to lob the ball in the end zone and he knew exactly where the ball would descend. Into his hands. As it did.

20-13. Over.

I think about this a lot not because it’s the schrapnel of my tranche of faded quasi-glory (though it very well might be) but because it exemplifies the comforting serendipity of luck. The receiver and I were pals. We practiced that play for years. In our backyards. On the recess playground at school. With a Nerf ball in his basement. And at football practice for two years. We missed a lot. I usually lobbed it off his oversized skull. Thwump. Or I overthrew him by an embarrassing distance. Whoosh. But we also ran it perfectly about ten thousand times. So, in serious pain and exhaustion yet still feeling the pressure, it was my go-to and he knew it.

To me, a huge part of hope and optimism is knowing that you can accomplish something. Seeing oneself at a really shitty point A is a realization, not an end. There’s never an end while there’s still time on the clock. There’s always time to write 21 lines of poetry that can change your life or change the world.