Businesslady and Aunt Acid: What to Do When Work Friendships Sour -The Toast

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Are you in need of advice? Write to with “Aunt Acid,” “Businesslady,” or “Ms. Proprietypants” in the subject line.

Greetings, Toasties! Aunt Acid and I received another joint query, which reminded me of one of the very first letters I ever received—and one that I’ve never quite found the words to answer. Today, we take a two-person look at the difficult storm that erupts when work friendships (or friend workships?) go sour.

Dear Businesslady and Aunt Acid,

I’m addressing my question to both of you because this is a matter dealing with good friends turned business partners. What a terrible idea, I know. I apologize in advance for the length, but I’ve never written to an advice column before and so I’m hoping I’m following protocol. [You’re fine, but I’m redacting/tweaking a few things below in the interest of brevity and anonymity. —B.]

About 4 months ago, two of my close friends (they are also a couple) approached me with a nascent idea for a start-up. This was in July, when I wasn’t working, and they were serving their notice period at work. They suggested that since they would be relieved of official duty July 30th, I should move to their city the first week of August to begin work. Come August, they suddenly decided to go on a two-month break, and postpone work on the start-up. I was upset, and I told them I wished they had involved me earlier, since this decision affected me as well—a point they disagreed with. But I agreed we should resume the discussion when they got back. They promised to call me around mid-September, which they did not.

I have since taken up another job, because the start-up seemed to be on indefinite hold. I mailed one of them a few days ago about something unrelated. They called me yesterday, and said they would like me to join them again. I explained that I had already taken up full-time work, but I would still like to help out in a reduced capacity, pending further discussion. They insisted I make a decision right then about my role, equity shares, etc., all of which they have apparently discussed with their lawyers, but never told me. Every time I had asked about finances in the past, I never received any information. I pointed out that it was unfair to ask me to make a decision like this, especially since they stated it will not be an equal partnership, and that work will be on ‘their terms’—terms they have not explained. I should point out that they have repeatedly made decisions without even letting me know (such as re-locating the office to yet another city), and have never been forthcoming with information (there are several mail threads where I’m the only one writing). I told them that I didn’t understand how I was supposed to work with them if I never had any information, or any choice with respect to decision-making. 

I have just received a very angry missive from them this morning. They accused me of willfully misunderstanding them, and said that I am the one behaving unreasonably and hurtfully. They reiterated that they really want me to work with them, but also told me that they’ll only give me information on a need-to-know basis. I have not replied to the mail yet, since I am upset and angry, and I don’t want to say anything I might later regret.

These guys are close friends, but I feel strongly that they have not treated me well, personally or professionally, over the past few months. Am I overreacting? I still like the business idea, so I would still like to be involved. How do I make it clear that I would like to work with them, but that I would also like to be treated fairly and not taken for granted? I feel like no matter what I do, the friendship is ruined. Is this how start-ups really work? I realize that my feelings are complicated, but I’m miserable about this, and very stressed out. Thank you for listening to me!


From Start-up to Dust-up

Dear Dusty,

I can’t speak to “how start-ups really work” in the abstract, but I can speak to this one: it’s not looking good. Friendships and work relationships can be a bad combination even when everyone’s on their best behavior—and what you have here is the rare trifecta of romantic relationship + work relationship + third-party friendship, all in the unstable context of a brand-new business. If you were writing to me four months ago, I might not have said “what a terrible idea,” but I’d have advised you to tread very, very carefully.

But now that you’re in the thick of this, here’s the best path forward: First, figure out what you really want. Second, figure out whether or not it’s actually achievable. Third, either go forth and make it happen or else see step one.

Right now, it seems to me that a lot of your desires are incompatible. You consider these start-uppers close friends, but you also feel like your friendship with them is inevitably ruined. You’d like to work with them, but on terms that seem pretty different from how they operate. You don’t want to say something irreversible, but in the meantime you’re biting your tongue about a serious misunderstanding.

I realize I’m only getting your side here, and maybe the start-uppers would have a different tale to tell: about the difficulties of getting a business off the ground, about the legal complexities, and about how their friend/would-be colleague seems clueless about the reasons a married couple wouldn’t share privileged information outside the duo. (Although to that I’d still say “yeah, well, the whole “leaving an unemployed person in the lurch after they moved to be closer to your workplace seems pretty shitty,” among other things.) But at the end of the day, it doesn’t matter who’s objectively “right” in this situation—what matters is what happens next.

Your start-up buddies have developed a workflow and see no problem with it. You feel like it’s intolerable, yet are still intrigued by their idea (and, if I’m reading you correctly, would like to salvage the friendship if possible). So I’m guessing that the “what you really want” from my step one above is: Make This Work, Somehow.

The good (“good”) news is that if the friendship’s already ruined and the business partnership is technically nonexistent, you have nothing to lose. That means, forget the shouting-into-the-void email threads. Pick up the phone or get on Skype or otherwise figure out a way to talk things through with them in real time. If that means scheduling a call—something I personally hate doing with friends but which I begrudgingly acknowledge is often the only way to actually talk to them—so be it.

And then, hash. this. out. once and for all. Try to keep an open mind as they explain their perspective, but not so open that you ignore everything that’s happened before. Listen carefully to how they respond to your concerns. Are they eager to put a plan in place to make you happy—one that’s documented, on which you’re given full input? Or is it more about “aww, Dusty, you’re our friend, let’s chase this dream together and it’ll all fall into place eventually”? This is your one shot to reach an agreeable solution, so make it count.

Then again, I’m mainly focused on the “how not to make your livelihood dependent on a fraught interpersonal dynamic” aspect of this…Aunt Acid, what’s your counterpoint?


My eyebrows went up at the second paragraph and I snorted for the first time shortly after that. Darling Dusty, you had the right idea: get out and stay out. You deserve better. Your close friends do not know how to run a business or, it seems, maintain cordial, respectful relationships. No one who values your time would demand that you obey first and find out about vital information such as finances, equity shares, and so on second / never.  

They may say they think you’re important. Their actions scream otherwise.

Whatever their other virtues — are they good at backgammon? do they pick you up from the airport? I’m really curious what makes them “close friends” — this high-handed couple seems to be composed of equal parts antagonism and poor communication. These are not traits you want in people you work with, especially in a small, scrappy, start-up capacity. And believe me, I know. I once quit a stable work situation for a position at a great-sounding small, scrappy start-up. There was more optimism in that office than there is helium in the average balloon. We were young! We were bright-eyed! We were unstoppable! We were even featured in The New York Times Magazine! And, thirteen months after we started, we were out of a job.

Good governance matters. Though the leaders of our start-up were intelligent and ambitious, they had never run anything before, and it showed. One bad decision after another weakened us and finally sabotaged us altogether. On the Friday afternoon in January when we were all let go, given no notice and only black Hefty bags with which to clean out our desks, the CEO who had inspired us so much didn’t even show up to work.

Here’s another story: I’m close to two people, K and S, who joined/started a new venture with a third party, TP, who had been a friend. TP turned out to be a difficult person to work with: he disappeared for stretches, he neglected his tasks, etc. Within the year, K and S had to ask TP to leave, and TP, who had unlimited funds at his disposal, hired a high-price lawyer and sued. To keep the matter out of court, K and S were forced to settle — which means they are responsible for paying TP a whopping $15,000.

So when I look back on my experience, I consider myself lucky. At least my mistake didn’t come with a five-figure price tag.

Businesslady is right that what has happened has happened, and there’s little point dwelling on it. You’ve done a good job, it seems, at not letting yourself get dragged too deeply into your friends’ drama. You’ve gotten a new gig. You’ve moved on. Wish them well and let them go. Be polite, of course, but I’m sure you will be; you’ve acted reasonably thus far. And no matter how much invective they sling at you, try to resist the impulse to yell back. Someday they may be rich and you may want to get an invite to a party on their yacht. Odds are they won’t be, though. The vast majority of start-ups, even well-run ones, fail — viz., the fascinating podcast Start Up, season two. Thank your stars you got out early and, to a large extent, got off easy.

Start-ups seem sexy and exciting. Working with friends seems like a no-brainer. But your gut is right about this particular situation: it’s not worth it. Reward your gut with an ice cream and get on with your life.

—Aunt Acid

Dear Businesslady,

I really don’t know what to do anymore. I feel so sad and trapped. I started a collaborative art project with a friend of mine, and over the years we have built success and a fan base together thanks to her hard work and good connections. But in recent years my friend has become very hard to deal with. She has bouts of absolute insanity during which, out of the blue, she screams at me and says really hurtful things and then seconds later switches back to normal and expects me to pretend it didn’t happen. We live in different cities and I do not have another regular job (which is due to the fact that I need to be free to travel to do work with her) so she expects me to come whenever she pleases, and she gets very upset when I don’t do as I am told. Sometimes I shy away because she scares me so much, which makes her even angrier.

I have really tried to talk to her several times, but it is not possible to have any rational arguments with her. She speaks badly about me to my other friends behind my back (which they tell me about with shock and concern). I feel my heart racing every time I get another email from her, as they are almost always full of accusations and deluded ravings. I don’t know if I should give up this project and try to find a more ‘boring’ day job (and even if I had the courage, I don’t know how I would try to extricate myself from it all; there are contracts and obligations that bind us to the shared work) or if I should just keep putting up with her and develop a thicker skin for the prize of growing success and doing something that I love — albeit with someone who is sometimes unkind and who terrifies the living shit out of me.



Dear Desperate,

My own desperate wish is that you’ve found yourself in a better place by now. But I wanted to publish this letter in conjunction with the earlier one, because in many ways my advice to you is the same. The only difference is that the stakes for you are much, much higher.

Because: you can’t change people. Your friend—and I find it hard to call her that given the way you describe her treatment of you, so let’s call her your fiend instead—has fallen into a very specific pattern of behavior. If she won’t listen to your arguments and has a distorted view of the reality between you, I don’t think there’s a fix.

So this all comes down to you. What you want, what you value, what you can tolerate and what you can’t. Developing a thick skin can be a useful professional skill, and being successful at something you love is a rare opportunity—if you were writing “everyone says I’m being foolish for seeing this through, but I think the benefits outweigh the costs,” I’d say screw the haters and keep forging ahead.

But instead you’re talking about how you lack the courage to leave, and to me that suggests that leaving is what you have to do. Breaking contracts and upsetting the status quo is logistically complicated and emotionally disruptive. Your fiend will likely ratchet up to a new level of anger and abuse. You will feel the sting that comes with telling people “no” in a world where so many of us are socialized to always say “yes,” and there will likely be guilt and a sense that you should’ve just stuck it out. That will all fade, though. And once it does, you’ll finally be free. I hope you already are.


Businesslady is in her early 30s and somehow managed to find a rewarding career despite her allegedly useless degree in the humanities. Her job history includes everything from food service to retail to corporate nonsense, but she currently does writing and editing for a nonprofit, and devotes the rest of her life to playing video games, patronizing bars, and spending way too much time on the internet.

The role of Aunt Acid is played by Brooklyn-based know-it-all Ester Bloom.

J. Longo is a freelance Illustrator & Storyboard Artist in Brooklyn, NY. His work can be seen at as well as on Instagram.

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