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- I'm challenging you to a 50-mile walk
I'm challenging you to a 50-mile walk
PLUS: Notes on China, Luxury apartments in Kenya?, How to focus by Steve Jobs...
Welcome to this week’s edition of ‘The Adventure Capitalist’. The Adventure Capitalist is for the uncommon man.
This week is a special email. We're issuing a challenge to you, a challenge that some of you will be inspired by and others will be repelled by.
Here’s what you can expect in this issue:
Introducing ‘The Kennedy March’. Are you up for the challenge?
Some of the best travel related wisdom I’ve ever read
An assortment of links to get your blood flowing
The Kennedy March
We choose to go to the moon, not because it’s easy but because it’s hard. - JFK
In 1908, Teddy Roosevelt issued an executive order challenging the officers of the Marine Corps to do a 50-mile hike in three days. His goal was to create a standard level of fitness, so he called it the “50-mile standard”. The Marine Corps, being as hardcore as they are, said three days is too long – we'll do it in a day.
Then in 1962, President John F. Kennedy learned about Roosevelt’s 50-mile executive order. He sent a memo to the Marine Corps Commandant David Shoup suggesting that a similar 50-mile challenge would be a good test to see how the present-day officers could perform the task.
Concerned the average American was becoming more and more unfit, President Kennedy announced that he would also put his White House staff to the 50-mile test as well. It was meant to be a publicity stunt to kick-start the national fitness campaign, and the press ate it up.
The President's brother, Bobby Kennedy Sr. immediately took up the challenge. On February 9, 1963, Bobby Kennedy completed 50 miles in 17 hours and 50 minutes, through slush and snow in a pair of oxford dress shoes.

A snapshot from Bobby Kennedy’s legendary walk
His legendary walk inspired tens of thousands of Americans to grab their running shoes and hit the trail. His 50-mile walk was the inspiration for the first-ever ultra-marathon, the JFK 50, hosted every year on the anniversary of his death.
The Challenge:
Today, I’m challenging you to complete a 50-mile walk in under 20 hours sometime during the month of May.
Completing a 50-mile test is simple – but hard. All you need to do is walk.
Are you up to the task?
Why should I do this?
Some of you are going to read this email and know it's something that you have to do. Others will read this email and say, "no effing way." I'm not here to convince you to do this.
I only recommend undertaking this if you feel like it's a type of challenge that you're looking for in your life.
Walking 50 miles in one day is going to suck – but it's not something you'll ever forget.
You can probably get through the first 25 miles no matter who you are, but the second half of that walk (from mile 25 to 50) is going to be a suck fest for just about anyone.
Our goal is to inspire you to get out of your comfort zone and heed the call of adventure in your life.
FAQs:
When is it?
To put it simply, any time in the month of May.
The only requirement of this challenge is to complete a 50-mile walk during the month of May in under 20 hours.
I'm sending you this email on March 27th, which means you have over a month to prepare and train for a 50-mile walk. If you're in decent shape, this should be enough time.
If you're not in great shape right now, maybe you don't complete the entire 50-miles but instead you go for a long walk. This can still be the kickoff to getting yourself to where you want to be.
Is this something I do by myself or with a group?
That is entirely up to you. You can do it by yourself or with a group.
Option A: You map out the route, you start walking, you suffer, and you grow as a person.
Option B: We have recruited leaders of this 50-mile challenge all across the country who will be hosting walking groups.
Current Regional Groups:
Florida, Oregon, Austin Texas
If you're interested in joining us for a 50 mile walk (either on your own or with one of our groups), please reply to this email!
The Adventure Capitalist
Within the US, and around the world, people are having fewer babies. What does this mean for investors, who are looking for places that are growing (versus shrinking)? We dive into what US states are growing the most, what countries around are growing the most, and why we should all be aware of what's happening.
🎙️Listen on Spotify, Apple Podcasts
The Lifestyle:
🌎 Global Adventure:
I love seeing what you can get in different countries in terms of housing. This is what you get in Nairobi, Kenya for $142,000 - a four-bedroom palace (link)
Are you interested in learning more about China? This is a fascinating video on scale, construction, young people, public opinion, censorship, tech, and AI in China. (link)

This paragraph, written by Kevin Kelly, is probably the best travel-related wisdom I've ever encountered.
💰Wealth, Business, and Life:
This is a fascinating video from Jony Ive on what he learned from Steve Jobs about focus (link)

Wake up and choose adventure