The hardest single day of my life

Last updated on 02 Apr 2025

Mount Kilimanjaro is not an adventure to be taken lightly. She demands your utmost respect and complete surrender. Without question, I gave her everything I had — mind and body — as tribute for the opportunity to reach her summit.

My total trip included this 9 day hike of Kilimanjaro, a 4 day safari in the Serengeti and surrounding parks, and then 3 days on a small island 20 miles off the coast of Tanzania named Zanzibar. I did the bare minimum of pre-planning, I didn't learn much about Tanzania, I didn't try to learn any Swahili, I didn't pack well, and I didn't train for the hike at all.

I just said said yes to a grand opportunity and showed up with a good attitude and a willingness to engage with the chaos of the universe.

If I could impart some some life wisdom on you it would be to that as much as possible. Planning too much of life is the same as planning death, pointless.

Full image gallery of Kilimanjaro

What are you capable of?

The hike wasn't so bad until the final day, then final day was indescribably difficult. It was 8.5 hours and 4,000 foot elevation up and then another ~9 hours and 9,000 feet down. We started at midnight when it was freezing cold, pitch black, and foggy. For the first 5 hours I couldn't see anything in any direction except the persons shoes in front of me. This combination gave me some very uncomfortable sensory deprivation effects, my eyes were rolling in the back of my head and I was hallucinating a bit, and this went on for hours until sunrise. By the time the sun got out we were climbing at 18,000 feet where the temperature had plummeted and the air was thin.

My body had long given up by this point. I truly can't tell you how I got though the day other than the human body is capable of feats beyond what is physically reasonable or explainable. We reached the top around 8:30am, saw the sign, and immediately started our trek down. I didn't get much good photography at the top because all I could think about was getting to lower altitude and the 19,300 feet we had to descend over the next 2 days.

This adventure makes me reflect on the dozens of times in life that I didn't think I could do something, and then did it anyway. I didn't think I could join the Army or jump out of airplanes, I didn't think I was smart enough for college, I didn't think I would ever own a house, I definitely didn't think I would own multimillion dollar apartment buildings or be a millionaire, I didn't think I would ever be able to deadlift 500 pounds, and I didn't think I could really be a world traveling photographer....and yet all those things were not only within my capability each of them made me realize I was setting goals that were way too small.

Whatever you think you're capable of, you're wrong.

You can do more.

Immense thanks to the crew and Steve

4 of us climbed the mountain together with a support crew of 24 people. They made our tents before we arrived at each camp, then made us food, then in the mornings they would break everything down and pack the camps on their backs, blow past us during the hike and get to the next camp hours before us to set up the tents and prepare food. They did this for 9 days straight while carrying way more than us and for the final day they even took our packs. They carried our gear while watching us struggle. It was some weird combination of humbling and humiliating. The guides, porters, and crew of Follow Alice were at least as impressive as the mountain herself.

Though I benefited from this trip I didn't plan it, Steve did (my father in law) and it's unlikely I would have done it without him. I am tremendously thankful for that. I think more people would go on adventure like this if it gets on the calendar and Steve has a super power for making that this stuff a priority. Everyone needs a Steve in their life to help them prioritize adventure.

Digital detox

9 days without the internet was very healthy for me, and I am surprised to admit it. I love the internet but I definitely felt more clarity and confidence of thought without having the constant bombardment of random "stuff" in my head all day every day.

I'm going to 'try' to do less doom scrolling, less random internet and focus more on long form conversations, deliberate learning, and using the internet to create and serve rather than consume and distract.

This is a very special image for me. IYKYK

This is a capstone (...mostly)

I'm not sure how long you've been following this newsletter but I started documenting my real estate journey in 2018 and I was writing and acquiring a LOT of assets until ~2021 when the real estate market dramatically changed. We entered into a retail priced market around 2019, then covid inflationary environment saw prices soar with interest rates still subsidized. I couldn't buy anything underpriced and it was extremely obvious that rates would increase making acquisition essentially impossible (which is what happened and many people are now paying a severe price for not seeing this). At this point I made the greatest sin in real estate investing I decided to wait, or as I prefer to call it I took a strategic pause. Perhaps more accurately I just stopped buying assets that didn't make money. I took some time to travel the world with my camera and enjoy the freedom I had worked so hard to create. I also explored other financial opportunities including various partnerships, I networked my tail off, and I launched the BetterLife podcast in Maui with Brandon Turner. None of those opportunities really worked out the way I wanted but that's the point of exploring, to see what sticks, and regardless it's been a wonderful 4 years full of life.

I think I'm done exploring for a while, I'm now in Austin and I'm here for good and I have a new bride and I'm with her for good. It's time to sink my teeth back into making money and creating wealth, which I have a plan for and have already started and I will share that journey once I get make a little more progress. Kilimanjaro will be a great capstone to this passing chapter and allow a new one to start.

Adventure first

The reason I said this was "mostly" a capstone was because I don't see much point in making money or even being alive if I can't go on grand adventures occasionally. So to do this responsibly I will now schedule a single big adventure each year and build the rest of my year around it and say no to the random stuff for a while. I think this is makes for a healthy balance.

Next year I'm going to do the 8 day Inca Trail to Machu Picchu and I'm am going to make that a group trip and bring some people with me. My bet is that other people have the opposite problem as me, instead of going on too much aimless adventure they go on not enough or no adventure at all, and if I can plan and get them on the books then more people will go - and that's a worthy service to the world I think.

My responsibility to you

I've never had any real plan for this website. I knew what I was doing was valuable and I wanted to leave breadcrumbs in case it could be useful to the next person, and it has, but I haven't really invested into a structure or process to truly help people. I haven't packaged what I've learned to make it accessible. This is because I've been learning myself and I hate seeing people who learned something yesterday turn around and start teaching it at high cost, but this trip changed my mindset.

The lifestyle and investing philosophy that I have implemented over the last decade has created a wildly fulfilling life backed by a bulletproof balance sheet. I set out to create this life and it worked, now I'm confident that I can give this philosophy and system to other people.

Last year I started a free Whatsapp group with a few dozen of my financially minded friends and it's been great but I want to turn that into a more robust platform and I'm invest my heart and soul there.

I'm currently calling it the Ascentic lifestyle - I want to get away from the stupid middle that is 8% average annual return index investing or other investments that only slightly beat the market but take on tons of additional risk and labor. My goal is not return maximization, it's life maximization. I think the wisest portfolio style is a combination of bullet proof near-zero risk cash flow assets combined with extremely high risk and high upside opportunities. This would allow a person to pursue a life of adventure, curiosity, art, and deep human relationships while getting extremely wealthy and not having to worry at all about systemic market risks. It's a combination of Dave Ramsey and Nassim Taleb.

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