Dark net markets are a competitive environment. As these anonymous markets enable criminals to trade illicit goods or services, this causes vendors to operate under pseudonyms, rather than real-world identities. The constant battle between market admins and law enforcement makes the typical lifespan of a market two years. When a market disappears, active vendors migrate to other markets with the intention to continue their business, or have already pro-actively done so in an effort to ensure business continuity. To secure their reputation across markets, they can try to obtain the same pseudonym on multiple markets, but other individuals could beat them to the punch. A much safer method therefore, is to generate a PGP-key and use the public key as identification across markets. This way, vendors signal their continued trustworthy and reputable service on markets to buyers. In this paper, we leverage the use of PGP-keys to map careers of dark net market vendors. We parse and analyze scraped data from over 90 dark net markets (2011-2015), and discern 2,925 unique careers. By employing group based trajectory modelling, a type of latent class analysis, we infer three different career trajectories - differentiating ‘established’, ‘challenger’ and ‘failed’ vendor careers. We show that these trajectories are heavily unbalanced in terms of longevity and success. We find that on average 80% of careers last just four months and generate very little sales. Only a small group (∼2%) of highly successful vendors have a long and uninterrupted career that lasts years and spans multiple markets. This group is also responsible for at least 31% of the total revenue in our data.