Are you part of the Medellín Cartel or the Cali Cartel? No, I’m not talking about the infamous cocaine cowboys of old. Nor is this some ramshackle post about which Narcos character you are (I’m an agent Pena btw). But thanks for stopping by if that’s what you were looking for. I’m talking about your approach to your career - and to get a bit more existential, also your life. Your path to financial freedom (or not). Because really, there are only two types of people in the world (at least in modern western society) out there trying to make it: The Calis and the Medellíns.
t has been brought to my attention that this article might make more sense if you have seen the Netflix series Narcos - or have a cursory understanding of what went down in the 80s in Colombia with the competing cartels. Go watch it - it's a great series.
Are you part of the Medellín Cartel or the Cali Cartel? No, I’m not talking about the infamous cocaine cowboys of old. Nor is this some ramshackle post about which Narcos character you are (I’m an agent Pena btw). But thanks for stopping by if that’s what you were looking for.
I’m talking about your approach to your career - and to get a bit more existential, also your life. Your path to financial freedom (or not). Because really, there are only two types of people in the world (at least in modern western society) out there trying to make it: The Calis and the Medellíns.
So, what am I talking about? Obviously I’m not talking about contemplating and plotting your drug running career. I’m talking about how you fit into modern society - what career path have you chosen and why?
As a general rule of thumb, it breaks down like this: if you are pursuing an entrepreneurial endeavor, you’re in the Medellín Cartel. If you’re working for someone else, you’re in the Cali Cartel. It can be as simple as that. But, there are a few other signs to uncover a Cali or a Medellín. Let’s break them down.
The prototypical Cali comes from privilege and wealth. You often went to an Ivy League school, and followed that up with a Top 10 MBA program (or other professional school that gives you letters like MD or JD). You aren’t carrying debt because your parents foot the bill, or donated a building so they could say you went to Yale to their friends at dinner parties.
Your typical careers of choice are in Finance, Consulting or one of the professions (Medicine and Law being the most common). The bigger the brand name, and the more exclusive the hiring process, the better. Your identity is often wrapped up in the conglomerate you work for.
Your relationship with money is like that of a stale marriage - you take it for granted. Your parents have it, and as far as you know, always will, until it’s handed down to you (through a trust or other tax-sheltered entity).
You value the “security” that a corporate job gives you, but secretly admire those that have tossed their hats into the ring to start their own ventures. However, the thought of weaning yourself off your paycheck, which pays for a 2BR pad downtown and a Model S, makes you dispel any notion of taking the plunge into that app idea that you share at cocktail parties.
You are driven not by a desire for freedom, but more for a status goal that is constantly moving - it’s never enough.
You also have a “firm handshake and an easy smile” (as Pink Floyd puts it) that a polished upbringing and education can give you. You use them in your climb up the rungs of the corporate ladder, playing a political game of Survivor that culminates in either reaching the top, getting pushed out, or languishing in middle management hell.
More often than not, you are born into being a Cali. You can masquerade as one, but when it comes time to make partner or the C-Suite, it’s usually made in a deal at the Harvard Club in New York. A sort of nepotistic glass ceiling.
Like Pablo, you didn’t come from wealth or privilege. Most likely you grew up in a middle class or lower class family. Your family had high hopes for you, most likely pushing you to pursue the Cali path (despite being at a decided disadvantage there). Immigrant families fit snugly into the Medellín mold.
The gates to the upper echelons weren’t laid bare for you. If you wanted something, you had to kick the door in through hustle (or find the third door). This is generally how you were drawn to entrepreneurship initially - if you wanted nice things, you had to materialize them.
Perhaps you had the scores and the ability to hack it at an IVY League school, but you chose not to go because your parents weren’t footing the bill, and you didn’t want to take out the loans to pay for school. For that matter, you may dispel with the notion of school altogether. You know you can be successful without it and would rather jump right into starting a company rather than waste time learning concepts that you won’t use in practice (or you could learn through an online course).
You have a relationship with money that makes you more frugal than your Cali counterpart. It’s often feast or famine if you’re pursuing the entrepreneurial path, but your spending habits remain measured throughout. When investing in a business, you could be living on ramen noodles in a closet, but you maintain a vision of what your business could be.
You can be extremely successful as one of the Medellín Cartel, and many that do reach the pinnacle try to buy their way into the Cali Syndicate. But many find that they are not accepted into these circles, even after accumulating new wealth.
Where do you fit in?
I can hear it now: “But Mike, neither of these profiles describe me. I’m special, I’m different, I’m a unique snowflake blowing in the wind!”
That may be...and you will probably melt.
You know that old line from Gordon Gecko? “Bulls make money, bears make money, pigs get slaughtered”? Ok, maybe I'm abusing the metaphor (it's really referring to excessive greed getting you burned on the street). But this can also be looked at as a way to say you should pick a side. You can really only master one strategy. Try to do too much - and you'll get burned. You’ll end up like a sheep surrounded by wolves if you don’t give yourself wholeheartedly to one of these groups.
Sadly, whether you like it or not, you’ll have to choose one of these paths if you want to have career success, great results and eventual financial freedom.
And you may ask me - “But Mike, I don’t run my own business, nor am I a high flyer at a Fortune 500 corporation”. Well, you’re still in one of the two groups, you just may be in a lower ranking position within one of those groups.
You know the henchmen or the sicarios that carry out the hits for the Calis? The ones that don’t have many lines, get barked at and do the dirty work? If you work at a company and you’re a middle manager or further away from the inner circle, you’re one of them. If you don’t have a top MBA or connections to the upper echelons in a company, it becomes extremely hard to reach the top spots there.
The same goes for the Medellín side of things, if you have yet to bring on accredited investors, top firms, and get mentioned in the press. If you don’t feel like people are getting excited when you mention your ARR (annual recurring revenue numbers) numbers, they probably aren’t. You can often feel like a leper starting a new company. No one will touch you until you’ve achieve enough success that you don’t need their help anymore. C’est la vie.
It’s much easier to make the jump from Cali to Medellín, honestly. As mentioned above, the Calis that will go far are generally ordained from birth. That’s not to say you can’t make it as a Cali coming from nothing, it’s just more difficult. There is a ceiling on what you can accomplish, generally determined by your social capital within a company you have been devoted to and the decision making of a handful of hire-ups. It’s not entirely in your hands, and maybe Timmy will get the promotion over you because he has longstanding ties with a family friend of the CEO. That’s how it goes.
The exception here is the idea of “failing up” or getting acqui-hired. If you have enough success with your entrepreneurial venture that you were able to get traction, users and revenue flowing through your doors, you can find yourself in a cushy VP position at a top company - even if you fail spectacularly. This may be more related to the technology industry, but failing up is a common Silicon Valley trope. The top tech cos are littered with management teams made up of failed start-up founders. That’s another reason to go Medellín, as you do have a bit of a parachute, even if your company doesn’t strike gold.
This is an interesting point about the perceived risk of taking on your own venture. Yes, you may not build the next Snapchat, but even if you fail spectacularly, there are plenty of teams that would love to use your knowledge on the wins you did achieve, and how you built your product or service.
Of course, this is assuming that you made enough of a splash, raised enough capital and saw enough traction - at least for a time. As mentioned before, perception and political jockeying is incredibly important in the Cali realm. The executive teams at these companies want to announce to the world that they were able to make a huge get by hiring you.
Meanwhile, it’s slightly easier to make the shift from Cali to Medellín. Having a pedigree from a top brand company and top school connections can make it easier to find investors, and you may have uncovered certain problems in your corporate life dealing with customers that give you unique perspective on how to solve them.
However, in mindset, it can be very difficult for a Cali to switch over to the Medellín camp. They have been fed and taken care of, and have had a path set out for them, throughout their entire careers. The path becomes a lot more muddled when you take on the tall task of starting a company. The wins aren’t as easy or as obvious to come by. You could be flying high one moment, and a second from shutting the lights off the next.
It also takes incredible self-discipline to run your own company. There is no boss, there is no one forcing you to come in every day. You could conceivably take days off. But if you do, you’ll fall behind your competitors, and likely lose.
For many people, the task of choosing one of these sides can be daunting. It is not a lack of opportunities that become a problem. It is that there are too many opportunities, and that becomes overwhelming. How can you devote your time to one endeavor, one idea, one business when there are so many problems and exciting challenges you could be solving?
I was in this camp. Often attempting to build businesses on the side while working at a full-time job trying to build something meaningful
However, focusing on one thing is truly the only way to get extraordinary results. What makes this scary is that, as laid out in the tail end, we really only have the time and opportunity to focus on so many things. This is why multi-threading is so appealing (and was so appealing to me while I was doing it). Working a full-time job while juggling a side business. Starting a fund while consulting with different clients. The “side hustle” seems to be lauded in today’s world (or even downright necessary in some cities trying to make rent).
But, honestly, it’s very difficult to create anything with the level of quality needed to succeed when you’re focusing on multiple things at a time. That’s not to say you can’t accomplish many things, switch between Cali and Medellín and work the corporate ladder one moment and build an amazing company another.
Just focus on one path at a time, crush it out of the park and then assess from there.
Are you part of the Cali Cartel or Medellín Cartel and you want to grow your business? Reach out to me on Twitter 🐦, Instagram 📸 or LinkedIn 💡.
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