Look to the future

The future - This way friend!

Man have I been traveling a lot the last few months. Sure it’s tiring, but the energy from meeting awesome people around the world definitely makes up the difference.

I recently met two of the coolest Japanese guys ever, Masa and Taka, who invest in European startups for an enormous corporate called Recruit (1). We were in Copenhagen together last week eating dinner when Masa gave me an insightful quote:

Masa’s insight was the majority of conversations focus on things that have happened. When first meeting someone it’s ‘where are you from?’, ‘what do you do?,’  ‘where do you live?’ After a rapport is built the conversation turns to ‘what’s new?’, ‘how’s the significant other?’, ‘still hate your job?’

Rarely does the question ‘where do you see yourself in 5 years?’ come up. These future looking conversations are surely the most insightful and way more fun than dwelling on the past. But for some reason they’re difficult to bring up, even with close friends.

Looking back at my conversations with entrepreneurs, even these are more about fact gathering than forward looking. ’Who’s on your team?’ ‘How big is your market?’ ‘What’s your traction?’ All valid questions, but for investments that won’t pay off for 7-9 years shouldn’t I be focusing more on an entrepreneur’s vision for the future?

So, with the remaining 5 weeks of 2015 I’ll strive to have 50% of my conversations about the future. If all goes well, hopefully this past/future ratio will become a norm. Want to join in on my little test? Let me know 🙂

(1) 28k people company, just IPOd to raise $1b – most will be for investments

Don’t judge a book…

As I get older (1) I find myself judging others more harshly… especially during a first conversation. Which is funny, because throughout my life I’ve prided myself on being open-minded and leaving a positive first impression.

Recently with just a few negative signals I have a greater tendency to A) consider the person a moron, and B) try to promptly exit the conversation.

Surely this combination of being quick to both judge and exit hasn’t ingratiated me to some, but subconsciously the time/effort savings outweighs a long and boring discussion.

If I break down my first interactions over the past year they would broadly result in the distribution below (2):

Dislike to like spectrum

The Switcheroo

Something strange has been happening recently. If I interact a second time with someone I initially strongly dislike, I tend to be completely wrong and end up strongly liking them…

Strong dislike to like

Late last year I met a US VC at a European tech conference. Long story short I considered him to be a typical arrogant American and I ended up actively hating his guts.

A few months later I met the same US VC again, spent some 1-1 time getting to know him and his perspective, and ended up strongly liking the guy.

The same thing happened twice recently with people I’ve met in London – a strongly negative first impression, months later a chance second interaction, and now I not only respect the person – but both have becoming good friends!

I hope I hate them?

My complete love/hate flip-flops have occurred often enough that I (strangely) now look forward to a strong initial dislike. Yes some people are jerks I’ll never enjoy. Yet if a high percentage of strong dislikes are likely to convert into good friends, to me that’s a good investment of time.

These thoughts leave me wondering:

1) Is there a correlation between my flip flops and the relationship advice “the more you love someone the greater they can hurt you?”

2) What are ways I can improve my ability to defer judgement and quickly understand someone’s perspective?

3) How does the time between first and second meetings affect my flip flopping?

4) Of my initial strong dislikes, how many also dislike me? And is their feeling toward me correlated with me flip flopping?

Overall the lessons I need to remind myself often are to keep an open mind, continue meeting LOTS of interesting people, and make every attempt to understand the perspective of others.

If you have any advice or tactics on the above, I’m all ears!

(1) I’m 31, so not that old

(2) Despite my increase in harshly judging, I’m lucky to have a positive outlook that still results in a positive impression of 95% of the people I meet.

Friends all around

I have this funny habit while on the tube. Every time the doors open I stick my head out to breath the “fresh” air. Yep… kind of like a dog in a car. There’s no rational explanation for this habit (fresh air + tube = oxymoron), just something that felt good and stuck.

Well, the other day I was doing my normal fresh-air-seeking thing when I heard a voice call out to me:

“Hey, where you headed?”

I looked around for a moment and noticed the person calling to me was in fact the train conductor. My first thought was ‘aren’t these trains automated nowadays?’ I answered “Kings Cross” and proceeded to retract my head in time for the doors to shut.

Next stop, same fresh-air-seeking followed by the same conductor asking another question:

“What do you do?”

This question was a little more intimate – especially from what sounded like a brit – but nevertheless I replied that I worked in finance. We both did a head nod in mutual agreement that I was one of ‘those guys’ in the faceless world of finance.

This little correspondence went on for a few more stops until I reached Kings Cross and went along my merry way. Before departing I waived and said goodbye to my new friend and he did the same.

What a great feeling it was to make friends with someone in such an unexpected way. In fact, it made my day.

Since this incident, I’ve found myself in a variety of situations where normally I would go about my daily routine without much thought. But now my conductor conversation often reminds me that potential friends are all around us.

I plan on taking better advantage of this potential. I suggest you do the same.