Playing to win

“The devil’s in the details. The angel is in the policy.” – Mitt Romney
“Knowing what it looks like, and knowing how to do it, are two different things.” — Chris Connor
“I was determined and eager and that’s all this is. I find that a lot off the people that come into the business now do not have the same level of commitment. They don’t come in like little hungry beavers; they don’t have that look in their eyes. They are all a little too cool about it and I think it’s a life thing. You’ve got to do in looking like you want to be great at this.” – Alistair King
One of the concepts that came up at the Loeries was this idea of the difference between playing to win and playing not to lose. The former takes some serious guts. The latter is a recipe for mediocrity.
But here’s the other thing: there is a hell of a big difference between talking a good game and actually following through. There’s a difference between knowing what something should look like, knowing how to do it, and actually doing it. This is why the execution part is the hardest bit of anything, and why the people who can actually deliver wind up really changing the world. You are more likely to think you can if you’ve done it before, then you just go and do it.
Although shame, I was reading about Marissa Meyer (Yahoo’s new CEO) who, two months into her job, has ‘so far failed to provide a clear strategy going forward.’  Oh, snap. Here’s another case of relativity. Two months is a long time. It’s also a short time. You don’t want to go mucking with things and making big announcements until you’re sure it’s the right thing. And by sure, I don’t mean sure, I mean as sure as you can be before you actually have to make the call.
My life is hectic. This last week was a short one due to the public holiday on Monday. My meetings I had on Tuesday seem like they were about three weeks ago and by the end of the week I had, yet again, changed my mind/refined my thinking on one of the key things I’m working on.
It was a great week, and a terrible week. I had a two-day trip to Joburg and Pretoria on Wednesday & Thursday. Flying and staying up there is not cheap, so I wanted to squeeze literally every second of productivity out of the trip. This meant I waking up at 4am on Wednesday to catch a 5:45am flight, and then arriving at home about 1am early Friday morning. Managed four meetings Wednesday and three on Thursday, which ranged from pretty good to pretty damn awesome, so we got our money’s worth out of the trip. But on the flip side, I think my average sleep was about 6 hours, with the shortest being 4.5 hours and the longest 7. This was not sustainable and by lunch on Friday I could feel that my brain was not right. This is not a good feeling when every single meeting you have requires you to be operating at 100%.
My rock stars I work with continue to be rock stars. We found new offices this week (move is at the end of November), and I had a very interesting series of meetings. Literally across the spectrum from customers to prospects to ex-employees to resellers to potential resellers to one of our key partners to another company that could become a very key partner. And I discovered that we’re on Forbes 2012 list of top 20 startups in Africa.
Unfortunately I can’t speak publicly about any of the details of what I’m doing other than to say that it’s awesome. About 5% of the time I get a bit overwhelmed and think ‘Oh good Lord WHAT have I gotten myself into, this is 10x bigger and harder than I thought it was going to be.’ But the other 95% of the time I am excited and thinking ‘Oh good Lord WHAT an awesome situation to be in. This is 10x bigger than I thought it was going to be.’
Oh I guess I can say that I’m spending a good portion of my time in sales, and that not only am I apparently naturally good at it but I’m actually loving it. I’ve always believed I can sell anything I believe in, and one of the things about this job that specifically attracted me was the need to be out there actually actively selling which is something I haven’t done, can in theory do, and I looked forward to the opportunity to challenge myself. I sure didn’t anticipate that I would enjoy it so much but I am not complaining. I think it’s a mix of the meeting new people (and I love people), and the finding their actual problems and how we can best meet their needs (that I did at a macro level as a product manager), and the whole competitive aspect of the game.
Because from where I sit, the best way to beat the competition is to be better, smarter, faster, more aggressive. Gotta play to win rather than play not to lose. This is why I loved the Mitt Romney quote: my game right now is to get the best plan and then actually execute it. Both are important, and both are fun.
It’s spectacularly glamorous and spectacularly non-glamorous at the same time. But I’m loving every minute. It’s like I told Sam: it’s just like I’m in love. Actually, it’s not like I am in love. I am in love.
So this was a rest week (haha), but I’ve made some significant progress on rehabbing my injury which is awesome. I haven’t felt this healthy in months and I still have another week to go, and in this week I can actually control my sleep, diet, and make the time for the actual rehab.
Friday night through now has been pure pleasure. 27dinner on Friday night; I was like a kid in a candy store as a lot of people that I really like showed up. Some were people I see often, some were people I hadn’t seen in months. Even the talk was the best I’d possibly ever heard at a 27dinner and this was through the haze of exhaustion and two glasses of wine.
Slept in Saturday then went to a bodywork session, then acupuncture, picked up Sam and went to the Biscuit Mill then out for coffee, made another pot of coffee at home (I need more sleep), then drove to Kommetjie for my friend Amy’s braai. Quite fun. Talking to Amy about some serious topics got me thinking. Since I’ve started working for the man again I’ve become much more resentful of the robot beggars, and I think it’s because I feel guilty.
Related: on Thursday I had been trying to decide between dropping the rental car off at the airport or in Sandton and taking the Gautrain to the airport (Gautrain is a high speed rail link). Finally decided on the latter. Turns out to have been a good choice because the striking mine workers had hijacked the highway and were smashing car windows, throwing petrol bombs, burning tyres, etc. I do sometimes forget that I live in a dangerous country. Every time I drive on the N2 past the Cape Town airport and I see the police cars facing the townships I remember this fact but what strikes me most is that it would just never work. You couldn’t hold back that many angry people if they all really did decide to start looting and rioting. Let’s hope they don’t.
But hope is not a strategy now is it? Well, that’s actually not my problem to solve, happily. I’m not a politician. My job is so much simpler.
Sunday I had breakfast in Hout Bay with Rika, who I hadn’t seen in far too long. It was fun to tell her about my new job, and by the end of the conversation I’d told her exactly where I am as it relates to CrossFit, and what I’m thinking about the future. I had never been that open with anyone about it, and that she, an ex-Olympic athlete, thinks about it exactly the same way I do is a nice validation. These validations are less about ego than they are making sure you’re on the right path.  
Also, because it’s been on my mind: Cape Town is so beautiful. Joburg is vast and somewhat charmless and the drivers are an unholy combination of Cape Town crazy, Boston aggressive, and Miami aggro, and roads are not labelled at all until you are right on top of them. Hectic. Pretoria is slightly nicer and has the added benefit of a seemingly excessive ratio of stunningly attractive people to normal people. And it has jacarandas (which were not quite out yet). So I’m looking down the barrel of potentially spending a lot of time in this part of SA over the coming months and one wonders, in these situations, could I actually live here? Would I like it?
Of course I could, and I might even love it. But then I arrive back in Cape Town and it is so stunningly beautiful here it’s actually literally like another country. It’s actually breathtaking, especially now in the spring when you look at the mountains and the fynbos is in bloom, and there is so much if it that you can see the explosions of yellow and purple from kilometres away. Should you be lucky enough to go hiking, you can see even the small bulbs with their stunning displays of colour. Beautiful and unique. That’s my little city, at least for now.
And in just over a week, I leave. Autumn in New England, San Francisco, a road trip across parts of the country I’ve never seen, Denver, and New York City. Family, friends, business, and then some. Gonna be epic. Then I get back, which is going to be even more epic.
Overwhelming. But only in the best possible way. Playing to win.
  • “I don’t know him. But I know who he is.” – Lauren
  • “I see you’ve upgraded your phone.” – Misha
  • “He emails you? Oooh, you’re special!” – Helen
  • “You do present with a certain pathology.” – Byron
  • “Well, it isJeremy.” – Craig
  • “So. There are small businesses and there are big businesses.” – Craig (and our target market is …. ALL OF THEM)
  • “Maybe it wasn’t a matter of losing out but it was there waiting for you.” – Craig
  • “It’s called a vodka Red Bull.” – Doug
  • “The public transport system in this country is good for our business.” – Roelof
  • “There’s no value in free Wi-Fi if it’s awful.” – Dave
  • “In ur honor, i went to sleep at 4.40am this morning, waking up at 7am,  to simulate your new working conditions :-)” – Michael
  • “You’re tired so your defences are less.” – Debbie
  • “That’s a Pico.” “It looks like a candle!” – Tim & Monica
  • “If they’ve gone with another provider they’re probably unhappy now.” – Henk
  • “It’s a strange paradise.” – Henk
  • “Unless you’re a carrier you’re in a no mans land.” – a potential partner
  • “It’s hard enough for us to tell the customer to plug the cable into the wall. How he’s got three cables.” – Laurie
  • “Dating a rock star is exhausting!” – Sam
  • “This is a 27dinner, not a counselling session.” – Jess
  • “He’s such a porn star when he’s drinking!” – Jess
  • “Schools are the worst designed games in existence.” – Danny
  • “Here is where we step firmly out of the realm of the scientific.” – Byron
  • “You have outgrown it.” – Rika 


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