How to Fill your Yacht with the Best People

3 tactical pieces of advice for the rich, famous, and everyone in between… who are struggling to fill their yachts

I’m back!

Wealth is common in Barcelona. At least as far as I could tell… and I’m on vacation so I’m not going to look up the actual statistics. We’re going to go with it simply judging by the size and quantity of yachts I found in the marina. While I have not splurged on a yacht purchase of my own (yet), I found myself daydreaming one day of the optimal yacht length and who I would invite aboard. Too small and you can’t invite all your friends, too big and it feels awkwardly empty with a small gathering. Luckily for you, I now have some advice. So are you pondering a yacht purchase? Struggling to effectively fill your yacht? All aboard and read ahead! (Yes, I’m serious).

Note to self: read this article before any future yacht purchase. I’ve been thinking about this purchase for a while actually. Walking past the slips always reminds me of how I used my dad’s name to send away for yacht brochures when I was a kid. Needless to say, he was extremely confused when a sales representative reached out to him, but after 10-15 years I’m assuming they gave up trying to sell him a 60-foot yacht (it is simply too big for an inland Michigan lake). And frankly, after seeing some of the yachts in Barcelona, I’m a little disappointed I set my sights so low in childhood.

1) Maximize quality conversation

Quality conversation is rare. I had a close friend in town a couple weeks ago and while wildly different in the way we think and approach life I respect her, her opinions and our conversations.  What stands out the most is her willingness (and most-likely enjoyment) to tell me when she thinks I’m completely full of shit. When it comes to talking business and life, I find this rare, refreshing, and absolutely necessary for growth. With that candor often comes intensity and many times sudden, slightly awkward, but likely necessary topic changes. I would like to think the arguments are brought on mutually but then again she bought me “natural born asshole” socks… so maybe (most-likely) its just me. My Advice: Put as many of these people as possible on the yacht.

2) Quantity is best saved for entertainment

Based on the size of your desired yacht you probably have room for 10-40 people (again not checking these numbers). While a 40 person party is a good time, do you really have 40 high-quality friends? Probably not, but that is certainly not a bad thing as partying is for entertainment and having a good time. While rarely conducive for real conversation, it is a great way to meet new people and discover who can eventually fit into your “quality” category. However, it is very important to distinguish the two types, realize the potential drawbacks of each, and certainly balance accordingly. If you would like a first-hand experience in the potential pitfalls of not balancing quantity properly, I suggest starting your night at Glow Bar before a night in Bairro Alto (you can thank or curse after). My Advice: Quantity is great for entertainment, but has limitations and must be balanced.

3) Fill your yacht with great people.

Everyone knows the ancient proverb: you are the average of the 5 people who get drunk with you on your yacht. This wisdom has survived the ages precisely because it is true and you would be wise to heed its advice. I consider myself fortunate to be able to surround myself with amazing people and this truly stood out as I was leaving NYC. I celebrated my 28th birthday, as well as hosted a going-away party shortly before starting my journey (which is currently me writing this while overlooking the ocean in Split). I still remember looking around the room at both events and seeing successful, smart, great people who push me forward, bring new ideas, and will intelligently debate just about anything. And if you’re going to be stuck on a yacht with a group of people – that is exactly what you want. My Advice: Fill your yacht with people like my friends.

If you would like to invite me aboard your yacht (looking at you Richard Branson) and/or buy me a yacht of my own to discuss EdTech, lending, or economic development please visit My Ask page.

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2 Replies to “How to Fill your Yacht with the Best People”

    1. Thanks man! FYI Casino Barcelona doesn’t have craps so we’ll have to find a different port to stop at haha

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