Jonathan’s Newsletter

Sleepy Portfolio - Repeat Edition (September 2025)

Hi everyone,

Sep 16 • 

Jonathan Smart

3

August 2025

Trade Idea: A CRAK in the markets

Hi everyone,

Aug 28 • 

Jonathan Smart

2

Sleepy Portfolio - The Most Important Chart(s) And The Most Confounding Chart (August 2025)

Hi everyone,

Aug 15 • 

Jonathan Smart

5

July 2025

Sleepy Portfolio - Manic Markets Edition (July 2025)

Hi everyone,

Jul 9 • 

Jonathan Smart

6

5

June 2025

Sleepy Portfolio - War Edition (June 2025)

Hi everyone,

Jun 17 • 

Jonathan Smart

1

May 2025

Sleepy Portfolio - Calm Before the Storm or Mea Culpa (May Edition)?

Hi everyone,

May 20 • 

Jonathan Smart

1

A Tale of Tail Hedging

Summary: Using the rally in the market and decline in VIX/implied vols to buy long-dated tail hedges (deep out-of-the-money puts on QQQ).

May 2 • 

Jonathan Smart

6

April 2025

Clown Show Continues (April Sleepy Portfolio Update)

“There are decades where nothing happens; and there are weeks where decades happen.”

Apr 15 • 

Jonathan Smart

7

2

March 2025

Be Careful What You Wish For

Note: This is primarily a political rant (about Trump/MAGA), so if you don’t want to hear more politics, I ask that you too ignore and delete this one.

Mar 28 • 

Jonathan Smart

8

3

Sleepy Portfolio - March Edition

Hi everyone,

Mar 19 • 

Jonathan Smart

6

8

February 2025

Sleepy Portfolio - February Edition

Hi everyone,

Feb 18 • 

Jonathan Smart

5

3

Trade Idea: Vinci SA (FR:DG / US:VCISY)

Hi everyone,

Feb 13 • 

Jonathan Smart

2