The Mafias of GTM

well, I had a post last week that got ~80k impressions and drove quite a bit of comments:

One of the fun things about doing my own thing now with VibeScaling and GTMBA is that I can go off the cuff and post some of the dark thoughts 😈 about GTM that I've been brewing in my head during the week.

This concept of mafias has always been one; as an Italian from the NY suburbs (as well as a Goodfellas stan), the whole concept of a mafia has always stuck with me as an interesting way to describe a tribe of sorts that disperses out to create other forms of bond on their own.

A lot of this article I am about to write comes from my own thoughts, along with inspiration from Kyle Harrison's (GP @ Contrary, former partner @ Index) talent vortex articles (article 1 and article 2).

Obviously, the literal definition of a mafia leans illegal, but if we think of the good that comes from a mafia, it can stem from three things:

• Having intellectually stimulating conversations

• Understanding ways for self-improvement

• Building a network to further enhance each other's careers

The earliest sign of this in America (to my knowledge) was Benjamin Franklin creating in 1727 what is now known as Junto - his own version of a mafia. Members of the Junto were avid readers and intellectuals who were deeply involved in their personal improvement and that of society.

This feeling of being part of something unified (and elite) stems from deep human behavior; Alexis de Tocqueville best articulates it in his book Democracy in America, published in 1835:

Fast forward to the 1860s with the emergence of the American Mafia, which began as Italian immigrant criminal groups forming in major U.S. cities. Over time, these organizations evolved into a powerful and secretive network known as La Cosa Nostra, shaping organized crime in America for decades to come.

Similar concept - a bunch of powerful folks helping each other out in the current state as well as in the future, feeling almost a sense of being "indebted" to the tribe.

The point: this is something humans've been doing for hundreds of years. People want to be around smart people for their own selfish reasons, which in turn makes it even more powerful in an ironic way.

It becomes exhilarating, and we’re still drawn to it in modern day, but in a different way.

How Does This Relate to Tech?

The most famous translation is what is now known as the PayPal Mafia.

The phrase "PayPal Mafia" is used because, after PayPal was acquired by eBay in 2002, many of its early employees left the company but remained closely connected as friends, business partners, and investors.

This group became so influential in founding and funding new technology companies (LinkedIn, Palantir, SpaceX, Yelp, Affirm, etc) that the media likened them to a mafia, emphasizing their strong internal bonds, mutual support, and outsized impact on the tech industry.

The "mafia" label is a tongue-in-cheek reference to their loyalty, shared history, and the way they continued to collaborate and invest in each other's ventures, much like a close-knit syndicate.

The term gained wider exposure after a 2007 article in Fortune magazine featured a now-iconic photograph of the group dressed in mafia-style attire (photo’d above), highlighting their influence and the way they helped each other succeed in Silicon Valley.

It got me thinking of where these have existed in GTM throughout my career. For background, I graduated from college in 2014 and started that summer, but didn't join the tech sales community until late 2016.

Index has written about talent vortexes, in particular what made Plaid, Plaid.

It's fascinating to think about, and it got me thinking - where are the current GTM mafias (pre-AI and AI-native)?

Traits I've Seen in GTM Talent Hotbeds:

• Usually cerebral sellers (not salesy); went to good schools (ivys, nescacs, top public schools like Michigan/UVA) - high intellectual horsepower

• Want to join early/growth stage companies to get a cut on the upside (the best sellers are not NPCs and want to take more of a bet on themselves)

• Desire to be around builders

• More technical in nature (more true for the SaaS era, but actually now seeing more technical sellers sell on the app layer)

• Focus on intellectual challenge over pure commission hunting (more so, a Renassiance rep than being coin operated)

Why is it important to get into one of these?

It’s because people often land (the best) jobs through their network. See #1 in the article I wrote here on what makes sales roles desirable: high talent density.

Specifically, from someone you’ve worked with previously who then joins the next rocketship and then strongly advocates for you on your behalf during the interview process.

Interviewing without this, is just a slog and plummets your acceptance rates. Still possible, but just way harder.

That’s why the first time getting in is the hardest, and then it compounds.

So, yes, I don’t mean to say “just get into one of these” - but yes, do all you can to get into the AI-native rocketships right now. Some tips on how to land here.

Your career will take off mainly b/c of the network of people you’ll meet and build relationships with. These folks will disperse into other “mafias” and will pull you along with them.

Here is, to my knowledge, where a lot of the top sellers in my network have gone (and are going to) from the mid-2010s until the present day:

Pre-AI (2010s - 2023)

• Dropbox

• Slack

• Box

• Snowflake

• Mongo

• Grafana Labs

• Datadog

• Stripe

• Plaid

• Segment

• Retool

• Vercel

• Airtable

• Linear

AI-Native (2023 - Present)

• OpenAI

• Anthropic

• Windsurf

• Cursor (Anysphere)

• Harvey

• Decagon

• Unify

• Fireworks

• Clay

• LangChain

Note: you won’t see a lot of John McMahon companies in the pre-AI list for me, the reasons being:

• A lot of his tribes were before my time in tech sales

• A lot of those leaders always gave me “buy my software or I’ll whack you” vibes - what makes the orgs above elite is that they come off more polished IMO, and those orgs never felt that way to me. A little too salesy and less executive presence than I’ve seen in modern GTM orgs.

A deeper post on individual mafias will follow, but this was a fun one to write and think about (and I wanted to keep it under 1,000 words). Feel free to email me/LI DM me on LinkedIn with your thoughts or any others I may have missed!

🫡 cheers as the italians say, salute´,

Chris