SMIRK (audio version)
Tips for Dealing with, or Dating, Martin Shkreli

Tips for Dealing with, or Dating, Martin Shkreli

Chapter 16, Part 3: Here are mistakes I made and lessons I learned, so you don’t have to repeat them.

Through the lens of social media, everything looks surprisingly OK for Martin Shkreli a year post-prison. He has embraced what is perhaps his one true calling: being an internet character. And the internet has started to embrace him back. 

While Twitter (now “X”) owner Elon Musk hasn’t let him officially rejoin the platform, Martin’s latest alt account, @wagieeacc, has been allowed to remain active for several months, blossoming to a following of nearly 48,000. He’s managed to turn tech influencers into fans by jumping into zeitgeisty artificial intelligence-related discourse. Even some of the “bros” in Elon’s circle have reacted approvingly to his tweets.

He’s back to all the old tricks: Heckling reporters and liberal politicians; making sometimes offensive, sometimes hilarious irreverent jokes; sparring with haters (including calling out people who lob abusive comments from anonymous accounts); and either sarcastically or sincerely hitting on women who overtly sexualize themselves online.

For better or worse, he looks like he’s having a lot of fun. “Fun” can be an enticing quality for romantic partners…and investors. Numerous times, he’s indicated he’s on the prowl for both. Like me, plenty of people in Martin’s past, whether lovers, business associates, or a combination of the two, were sucked in by his cheerfully reckless anti-establishment antics.

Behind the scenes, though, I know things are less rosy than he makes them appear online. He still has tens of millions of dollars worth of judgments and legal bills hanging over his head. His main investment, his drug company Vyera, is being sold off for parts. And a promising new romance he began with an ambitious, beautiful woman (whom I became friends with) soured because he couldn’t let go of bad habits.

This excerpt from the Vyera bankruptcy refers to Martin trying to get $168 million from the estate to cover his legal and judgment costs. A judge rejected his claim.
This excerpt from the Vyera bankruptcy refers to Martin trying to get $168 million from the estate to cover his legal and judgment costs. A judge rejected his claim.

The journalists who gasped and clutched their pearls when I came out as Martin’s ex-girlfriend in December 2020 were devastatingly accurate about one thing: He was, and still is, a walking red flag. Intentionally or not, he constantly creates turmoil that leaves people hurt — financially, reputationally, emotionally, or all of the above.

I knew the pitfalls and calculated that I could survive them. But the going was still rougher than I anticipated. I wouldn’t want other people to careen down the same path without access to a roadmap. Throughout writing SMIRK, I have come to understand this is a purpose the book can achieve.

In that spirit, I’m going to share points of advice. They might be useful for anyone else harboring a secret wish to follow in my footsteps and try to date the “Pharma Bro”…or try to become one of his investors or business partners. Consider this like a Surgeon General’s warning label on a pack of cigarettes.

1. Don’t. If you value your sanity, it’s not a good idea to get involved with Martin Shkreli. It doesn’t matter how intelligent and self-sufficient you are, or if you can handle all of his negative externalities. He’s fully capable of driving anyone nuts. 

2. Don’t. This point bears repeating, à la the rule against talking about “Fight Club.” Seriously. Step away from the Shkreli.

3. Expect at least a few lies. If you’re going to proceed with any sort of relationship with Martin (despite me explicitly telling you not to), you should always be at least a little skeptical of what he’s saying. “If your mother says she loves you, check it out,” journalism teachers advise. You know the drill. Trust but verify.

Some investors have straight up called Martin a pathological liar, noting that he has misled people about everything from where he went to school to how much money he was managing at a hedge fund. Women he’s dated in the past have felt gaslighted by him when he said blatantly untrue things, causing them to question their senses.

I, perhaps overly generously, think Martin wants to be truthful — he’s a brilliant person who cares a lot about details and accurate facts and is often refreshingly more honest than most business people. But he’s sataboged constantly by his insecurities. He lies like my 7-year-old nephew lies when he’s caught doing something wrong. There’s nothing clever about the manipulation. It’s like he just trying to hit an “undo” button.

4. Recognize you are not special. I don’t mean you’re not special in the sense that you lack a compelling blend of intellect and talent. I’m sure you’re a very gifted, tenacious, worthy individual. I mean your interest in Martin is not special, nor does it make you special in his eyes. Martin doesn’t find it noteworthy if someone is intrigued by him. He’s used to the whole internet being curious about him. There’s a celebrity dynamic at play (even if you don’t think he should be a celebrity), and it will always be lopsided.

If your premise for entering a financial or personal relationship with him is that you chatted with him over Twitter or Discord and felt a “special” connection, be forewarned: It might be all in your head. And if he’s laid it on a bit thick and told you you’re “special” without even meeting you in person, look back at No. 3 and think carefully about his possible motives. (Also be aware he is prone to intense short-term infatuation and “love-bombing.”)

5. Be emotionally and financially secure. It is extremely precarious to count on Martin Shkreli for anything, in love or money. He dreams big, talks big, he want to be a hero, and he wants to be generous to everyone. But reality often falls short of his optimistic outlook, and he regularly fails to make good on his promises. When sh*t is going down (which is always happening because he is a human manifestation of chaos), it gets worse. He can’t protect you. He can’t take care of you. You have to depend on yourself. 

Financially speaking, that means you should be wary of leaning on him for your livelihood or trusting him with a substantial amount of your savings. Emotionally speaking, you must be able to mentally disengage from the relationship periodically (because I can assure you he will) and stop yourself from trying to seek his approval. Anyone who has an anxious attachment style or self-esteem problems should stay the hell away from Martin. He will make both worse.

6. Understand you can’t fix him. This was my biggest mistake, and looking back I can see how other people made it, too. I think of past investors like Brent Saunders who tried to coach him and make him behave more professionally, to no avail. I also think of Evan Greebel, the former outside corporate lawyer for Retrophin, who thought he could help Martin fix the mess he created by blowing up hedge funds; Greebel ended up in prison for 18 months and owing $10.4 million in penalties after being convicted of aiding Martin in fraud.

It sounds like a laudable goal — helping Martin Shkreli achieve his potential and be a better person. But trust me, it’s been tried MANY times by MANY sophisticated people, and it hasn’t worked. Martin’s craftiest deception may be his ability to convince others he has the capacity to change when he does not.

7. Have strong ethical boundaries. Even in strictly professional contexts, it’s not always possible to control human emotions. Love is love, and if it’s going to happen at an inconvenient moment you have to come up with a plan for how to deal with it. I credit my strong ethical foundation as a journalist and my deep sense of honesty with helping me navigate the difficult situation of falling in love with Martin Shkreli while I worked at Bloomberg News. I never accepted gifts from him, slept with him, kissed him, or even held hands, while I covered him for Bloomberg. 

Sympathetic though I was to him, I never would have lied in print for him. (I still won’t.) That was an absolute. When I finally realized I did love him, which was a very hard thing to admit to myself, I proactively chose to resign rather than let a conflict of interest fester. Glib people reading at a surface level will call me “unethical” for leaving Bloomberg to date Martin. Thoughtful people looking closer tend to see that my decisions were more ethical than most people’s would be in similar circumstances. I took the hard road.

Having integrity has protected me from the worst possible forms of Martin-related blowback, such as being dragged into his legal nightmare. Similarly, some of Martin’s close friends have managed to stay out of trouble because they are aware of the implications of Martin’s shenanigans and know where to draw the line.

8. Be comfortable with the worst-case scenario. I sacrificed incredible amounts of time, effort, energy, and concern for Martin and got very little from him in return. People will say I also sacrificed my job at Bloomberg and my marriage, but for reasons I’ve explained extensively here, I had decided I didn’t want either. I walked into my relationship with Martin knowing that at worst I would have a hell of a story to tell in the end. As a writer, I didn’t think that was a terrible outcome.

SMIRK (audio version)
My experiences uncovering the story of, and falling in love with, Martin Shkreli.