Flying a Kite into the Trend

There’s a simple principle I follow in investing which also relates to career planning.

That is to “Fly a Kite” in areas where I think there are going to be major winds.

Put another way, I simply want to go long areas I still believe have more tailwinds coming. 

  • Social media in the 2010s. 

  • EV’s and green trends as Tesla emerged. 

  • Crypto with the rise of BTC and ETH and Web3.

This sounds really obvious, and it a way, it is. 

But most people don’t always act so simple in their thinking.

We get really caught in details and complexity. We want to debate and discuss the finer points and counterpoints.

People worry about price and about picking the exact right bet. 

These things do matter. 

The question is when you’re making these bets, do they matter more than where we are in a trend? 

So that brings us to timing

Timing is the only key to get right. I don’t spend as much time on the details of anything else.

“Where do I believe we are in a cycle?”

If you trade volatility, will there be more volatility?

If you are going long, how much time does this trend still have to play out? Two years, 5 years?

I can do a lot wrong, but with good enough, early timing, I can often still come out ahead.

I like to think I spot trends early. I’m not the earliest of the early, I’m not the cypherpunk/hacker. 

But I’m also not the late majority. 

My sweet spot, I think, is the sort of the second group of risk-takers. Not the first in, maybe third.

I get excited early, then get bored before many others get excited.

So my thesis is really to spot the trend early enough that there is still a potential major tailwind ahead, and “Fly the kite” in that area by going long in some form or another before it’s obvious.

Then hold on until the thesis has really played out and the wind starts to die, before moving to new pastures.

This same thesis applies to careers. 

As we look at the landscape of potential directions our careers can take, the question is… which path do we want to go down?

And with this path, how are we putting the wind at our back or fighting against it?

One way I’m playing this is by being long investing and long video.

I believe that investing, and the language of investing is becoming more important to our careers. This means that being financially savvy is an asset that will only grow with time.

The second is being long video content. This one is interesting because most people would say the trend is late.

I think it’s STILL just beginning.

So there is an example of why this is tough. Timing is not always easy to understand or spot.

For both of these bets, this means expecting that whatever I do to grow my ability areas will benefit from an extra tailwind, that goes beyond my doing.  

I want the tailwind to bid-up my ability to more than what I could do on my own. 

When you leverage potential opportunities early, before they are obvious, you get the benefit of the trend expansion, which makes you look smarter than you are.

You ride the winds as a multiple on your effort or ability.

I think DAO’s and NFT’s fit in this category as well.

Cohort Based Courses would be another.

There are plenty.

The world is constantly changing.

This volatility and the new trends that emerge are your friends if you place yourself in their path and ride the wind.


XX I’m David Sherry, I coach, invest, and discuss the overlap of investing, crypto, and the creator economy.

You can join my Telegram chat for more real-time conversations.