Young Business Owners Share Their Best 'Actually, You're Speaking To The Boss' Experiences

There are few things quite like dealing with an entitled customer. We stand by it: Everyone needs to work in customer service at least once in their lives (because it'll teach them so much).

But there's absolutely nothing quite like dealing with someone who doesn't realize that you're the one in charge. That's ridiculously satisfying, as we were reminded once Redditor bigzachvapor asked the online community:

"Small business owners, who look too young to own the business, what's your favorite 'I AM the boss, lady' moment?"

"I ran a small non-profit..."

"I ran a small non-profit for a while. It ended up being a kind of big deal at a local level, which I'm super proud of."

"I had a sticker of the non-profit on my water bottle. At a party, a friend of a friend had the same sticker on her phone case. I pointed to her phone, then my water bottle, and gave her a thumbs up. She walked over and proceeded to tell me all about the organization and what she thought of it and how she got involved etc etc. She talked for a few minutes before asking how I'd heard of it. I told her that I suppose I'd first heard of the organization while sitting in my kitchen creating it."


"I'd occasionally work behind the bar..."

"I owned a popular neighborhood coffeeshop for several years. I'd occasionally work behind the bar pulling shots and making drinks, and I lost count of the number of people who'd come in demanding free coffee or whatever because they "knew the owner and he always gives me free coffee".

It always went down the same way: "I know the owner."

"No, you don't."

"How would you know?"

"Because I don't know you. That'll be $2.50."


"His reaction was priceless."

"I'm 20 years old and started a small business earlier this year when I was 19 making art from trash I find on the beach. When we sell the art it helps fund an artificial oyster bed sculpture we're attempting to make and install in the water to help filter pollution from the water. It's called Cilly Sells Sea Shells after a nickname I got when I was younger."

"So about a month ago, I met a guy at an event in a gallery I had pieces hanging in (this place hangs a lot of different artists and host music events pretty often). We started talking and mentioned our majors (I'm environmental science, he's marine biology) and he goes "oh you're gonna love this." He brings me over to MY OWN WORK and starts talking about it. Apparently his friend who worked there had told him about my work."

"I didn't know what to say, so I just didn't say anything while he talked about it. He said he loved how the pieces looked like glass and that they use stuff from the beach. Dude was clearly super into marine bio and talked about the science behind oyster filtration and all that. He had apparently been super interested in my project for like 2 months before he came to this and really knew his stuff."

"He picked up the big UV lamp that was underneath it and proceeds to show me how all of it glows in the dark. I pointed to my SELF PORTRAIT and said I liked how it glowed differently than the others. He looked closer and said nothing. At that point I had to walk away to greet an event organizer."

"Ten minutes later, a worker came up to me and said someone would like to meet me. Brought me up to the guy I was talking with earlier. His reaction was priceless."


"The customer doubles down..."

"I worked for a landscaping company ran by a man and his brother, Scott. The one brother Jim was the main boss, but his brother ran things when Jim when out of town. Jim was out for a week and his brother gets to one of their houses to cut it, The owner comes out and says, "hHey man, I'm Jim's cousin. He said you guys could trim the hedges while you were here today?"

"Scott says "No sorry man, I don't have anything in my notes about trimming your hedges today. I'll talk to Jim tonight and get your hedges sorted out, but it might be a few days."

"The customer doubles down, replying, "I told you, I'm his cousin, I think I would know if my family says he can trim my hedges for me."

"So Scott laughs and asks, "well how come I've never seen you at any family reunions?"

"The guy looks confused for a minute and finally Scott says "I'm Jim's brother, and we're not trimming your hedges today."


"I work in tract housing..."

"I'm 21 and started a construction company about 4 months ago. I work in tract housing, and I work alongside other sub contractor for the same builder. I was asked to go into a house to fix another contractors mistake. The electrician, who was in the house when I went in, thought I had made the mistake and basically called me an idiot, saying the house next door was much better built/straighter/cleaner and that my boss shouldn't accept my work. I gladly told him that I was the boss, and I was the one who built the house next door. We both laughed it off, not trying to make enemies with other trades I have to work alongside of."


"One guy came in..."

"I run a small wood shop that takes commissions from locals. One guy came in looking to order something as I'm planing a piece of stock. I stop and ask him if he needs anything, the same thing I ask all my customers, and he says, "You can't help me boy, let me talk to the owner." Keep in mind, I started this company when I was 17, and that's probably how old I was at the time. I also had hair down to my shoulder blades and a beard that hadn't fully developed a mustache yet, so he was quite right in his assumption that I wasn't an adult yet, but he left soon after I told him that, "Sir, I do indeed own this building along with everything inside it, and if you don't think i'd be capable in helping you, you are free to leave." He left."


"Most of the time..."


"This happens all the time for me, I'm a younger guy who owns a construction company specifically flipping houses. We also rent them etc. But every time I go over to a tenants house and fix something, or send the crew there its the same story."

"I know you came here to fix this but your boss said you'd also do blah blah blah" Most the time I'll just do it to keep people happy but there's been a few times I've had to tell them I am the boss and that never happened."


"One customer told me..."

"I run a retail business with my other half. I'm a 26 year old female but I look around 15/16 and often get mistaken as the student part-timer."

"One customer told me I looked 15. When I told her I owned the place he said, "Wow, you're so successful for being so young!" Had to break the news I was 26, not 15."

"Another time, a woman stormed in with a complaint about the delivery she just ordered. I explained the issue she had wasn't ours to fix (driver problem, they're not our drivers) and she cut me off with, "Can I speak to your manager." I deadpan, "I am the manager." She sizes me up, huffs, crosses her arms and asks what I'm going to do about her problem, then."

"I also remember a guy who started with, "So where's the boss today? The guy that runs it?" I pass the guys drink over and say, "Oh, you mean my husband?" He flustered for a bit and followed up telling me he knew I was also a manager and that that "guy" was my husband. Sure, dude."

"Oh, but my favourite one is the Asian lady who was unbelievably surprised I ran the shop we do (it's Asian based, my other half is Chinese) because "you're white, I didn't think you'd know what you're doing."


"I am..."

"I am a 24 year old PhD student working in IT. I am commonly referred to as ~18. I and a partner own a small service business. I always enjoy people trying to pay me directly for my service rather than going through the business. I don't always correct them, but the malicious ones always have a great look on their face when they realize I'm the owner they're trying to screw."


"My girlfriend..."

"My girlfriend got to turn down an MLM this way. "How would you like to be your own boss?" "I am..."


"All of them."

"All of them. Literally all of them. They jaw drop, the mystified look when they hear it, the stutter, the "oh s*** I f**** up" realization.... I relish each and every moment it happens."


"This place had been in town already..."

"Just today actually, and it wasn't even a bad one! I [27F] took over a small used bookstore in my town about a year ago (full year on the 26th, go me!). This place had been in town already for about eight years, and passed through one other person before me since the original owner, who I had actually worked for about five years ago. That said, this lady is in, wandering around and checking things out, making conversation, the usual. She mentions that her son brought her in, and last she heard the woman running it had a kid."

"I just laughed and answered that she was speaking of the previous owner, and that I was the new one and had been for a year. To which she seemed properly astonished, and then complimented the store- we have christmas decorations up, and a lot of them are handmade papercrafts because the decoration budget was nil."


"My mum owns a florist..."

"Similar but different. My mum owns a florist, and hired some new staff so that she wouldn't be working 10 hours every weekday. Her biggest rule is to NEVER refuse service to a customer, because the shop doesn't get too much foot traffic and all the stock is unusable after a week and gets thrown out, hence why every customer should be served. One day my Dad (who doesn't own the shop but has a lot of authority over it) was walking past the shop while a new staff member was on. He was about to ask if he could help (since just by looking at the shop, he could tell not much had been done) before she, without looking up from her phone, said that the shop was closed."

"The shop definitely was not closed. Dad definitely told the employee who he was, and definitely told mum what happened. The employee was definitely fired shortly afterward. As soon as she was fired, the shop went from potentially going bankrupt to profiting."


"I used to help..."

"I used to help at adoptions fairs through a local shelter at a local chain of pet shops (multiple shops in the same city) the owner dresses way more comfortably than anyone would expect."

"One time a lady was throwing a fit over the shelter's policies, and the owner the of pet store chain came over to find out what the commotion was all about. He just quietly listened as she raved and ranted about complaining to corporate and how she was going to get him fired and everything. He just took down her info and never bothered to tell her that she was yelling at and being abusive to the owner. Honestly he's kind of a cool dude."


"After three weeks of leash training..."

"I'm not a business owner but I do basic dog training and walking and general pet sitting as a side hustle. I'm a very small woman (5' 110 lbs)."

"I got a call from a dog mom asking if I could leash train her 2 year old Great Dane rescue. She and her husband have just been completely unable to get this boy to walk on a leash. We negotiate a price. I work on the cheap side because I'm not licensed but I want to help people so they don't rehome their dogs."

"I show up with my fiance and the husband and wife take one look at me and they are incredibly uncomfortable and a bit skeptical. I have my own slip lead and use their leash and collar. My fiance accompanies me and they ask their roommate to walk with us as well. Totally understandable."

"This boy is about 150 lbs and he is STRONG. He is also insecure and almost impossible to walk on a lead. He doesn't follow directions well but I'm determined. This boy has been rehomed six times in his two years of living and his parents are considering rehoming him if this doesn't work. They already have 2 adult female Great Danes and a puppy living with them."

"The first walk was horrible but like I said, I'm determined to help this pup and his family. The next day, I show up and he's excited to see me. He's a little bit better but not much. His parents are still skeptical. After a week of walks, when I show up, he actually goes and sits by the door to wait for me to leash him! His dad is amazed. Their lead was grossly wanting because they normally don't have to leash their females. I borrow one from my roommate that can hook around my waist."

"After three weeks of leash training, his parents are moving and I will not be able to train him any longer. But this boy has made progress by leaps and bounds! His parents are able to take him for walks around the neighborhood. He follows directions. He doesn't bolt. He's not as insecure as he once was. Our last training session, I meet the rest of the household. They call me a miracle worker. We walked for an hour and the only leash I had to use was the one around my waist. We were able to walk hands free. His parents decided to keep him. I'm especially proud of myself for this one."


"She ended up..."

"Me but also not me kinda."

"I look older than I am (guy on gfs account) and my old boss looked slightly younger than i. Well some lady came up and asked me if we had a specific phone case. I was honest and said I didn't know and that I could look (we had custom cases). As I started to look, the owner came over and asked if everything was OK. She replied with "yes sir, the owner is looking for a specific phone case."

"The owner replied with "I am?" And he started looking too. I turned around and told the lady that I couldn't find that specific image for her phone but the owner can make one for her if shed like. She stood there confused and then asked who the owner was. I pointed to my boss and said he is and my boss patted my back and said I was. So the lady stood there and was even more confused. A few moments went by and then co-owner came by and asked what the problem was."

"The lady said "I am looking for a specific image for my phone and they couldnt find it. Neither one of them could find it and the tall one said the owner can print one for me. I asked who the owner was and the tall guy pointed to [him] and said he was but [he] patted the back of the tall guy and said he was. Are you the owner (asking co-owner)?"

"The other owner laughed and said yes. He said he could do it and asked for the picture."

"She ended up getting the phone case but I don't think she ever found out who the owner was"


"I've been asked..."

"I co-own a clothing company and we do a lot of expos and booths. I don't know how many times recruiters, printers, manufacturers, whatever have completely ignored me and have gone to my athletes that come to help for the day to ask if they could be our manufacturer or if we could be a part of their event."

"I've been asked how long I've been working for the company, if I can give their card to my "boss", you name it. Even when the other athletes tell them I'm the one to talk to, they kind of talk to my athlete/ambassador or helpful friend instead of me especially if they're male and white. I just toss their card into the trash."


"He left..."

"For background, I don't own the business, but I am the general manager at a pool and spa store. I believe this fits here though. I am also a rather short (5ft tall) woman who, despite being in my 30s, gets mistaken for a high schooler at first glance. Also, I try to get a mix of both male and female employees, but not a lot of women apply for a pool store, so besides myself, the other 4 employees that day are guys, and it being seasonal for all but GM and ASM's, they are all between 18-20 year old guys in between college semesters."

"Customer comes in with a pump with a frayed/broken cord. I greet him, and am promptly ignored. Knowing I'm the only one that has shopwork training (I was put in this location to fix a failing store and had to train a whole new staff to boot) I walk off the sales floor and into the shop area to work on other equipment while I wait for the customer."

"So customer walks up to the young guy on register and tells him he needs his pump fixed, is told that shopwork is done by the manager and gestures to the shop window. Customer proceeds to ask 2 other brand new employees, they tell him they are still in training, but I would be able to help him, and point him towards me."

"Exasperated, the customer walks up to the shop window, and in spite of me standing there working on a disassembled robotic pool vac , says in a snippy tone, "hey, I need the manager to fix my pump, where is he?"

"I put what I was working on down, and with that "customer service smile" on , ask if his pump is 110v or 220v since the plug is missing (I can tell once i open the pump, but I prefer to collect all the parts needed first if I can) and if there were any other issues he can tell me about to ensure I have all the parts or if i need to get some from other locations."

"Customer looks at me, looks at the screwdrivers and test leads and says, "Honey, they told me I needed the manager, they said he was the only one who can do this, is he here?" (All in a tone like i was bothering him)"

"I kept that smile and reached out to shake his hand, saying "hello sir, I'm the manager, fuzzyoverlordsmom. Besides a new cord, is there anything else I can help you with today?"

"Unfortunately this guy was a jerk, and instead of brushing it off, apologizing for dismissing me, or just acting like a normal person, he questioned if i knew what i was doing and if ive ever even fixed anything before. I told him it was his choice to leave it w me to fix or not, but he does need to talk to me w the same courtesy and respect that he is being shown in spite of how hes been acting."

"He left and I fixed the cord, the pump seal & gaskets. Pump worked great after, and his wife came and picked it up. He came in a week later and apologized to me, and ended up giving me another tip. Hes been a model customer since."


"I worked for a landscaping company..."

"I worked for a landscaping company ran by a man and his brother, Scott. the one brother Jim was the main boss, but his brother ran things when jim when out of town. Jim was out for a week and his brother gets to one of their houses to cut it, the owner comes out and says, "Hey man, I'm Jim's cousin. He said you guys could trim the hedges while you were here today?"

"Scott says "No sorry man, I dont have anything in my notes about trimming your hedges today. I'll talk to jim tonight and get your hedges sorted out, but it might be a few days."

"The customer doubles down, replying, "I told you, I'm his cousin, I think I would know if my family says he can trim my hedges for me."

"So scott laughs and asks, "well how come I've never seen you at any family reunions?"

"The guy looks confused for a minute and finally scott says "I'm Jim's brother, and we're not trimming your hedges today."


"When I was 23..."

"When I was 23 I has just started a roofing company, put about 40 roofs in this neighborhood. Went to pick up a check for one of sales reps and got a very suprised look when I introduced my self as the owner."


"Growing up..."

"Growing up my mom owned a business. She did the majority of administrative and behind the scenes work while my father and a family friend worked the front end. Occasionally if my father was off, a customer would come in and ask for the boss only to be surprised/annoyed when she said she was the boss. One time this happened she was just over it and walked back into the office put on a jacket my dad bought her as a joke that said "The boss lady" and went back to the customer to say "now do you believe I'm the boss?"


"I'll take my boyfriend..."

"I'll take my boyfriend to yearly conferences and when at booths or when I'm getting supplies or reading material the people running booths will usually talk to him first, thinking he's the one in the field I'm in."


"Even when..."

"Everytime an older (60+) customer comes into my yarn shop and my mother's visiting the shop. Apparently, at 35 I'm too young to own a yarn shop. My mom (62) looks the part, so they all sidestep me to ask her. Even when I'm the one answering they still turn back to her with their questions."


"So satisfying."

"I used to have a window cleaning business. My employee, who is older than me, was standing nearby taking a short break while I continued working."

"Typical "Karen" pulls up and starts asking my employee about our prices, how to get an estimate etc, etc. I start answering questions over my shoulder while I'm working (time is money right?). She gets all huffy, and says something sarcastic like "Sir, I was talking to your boss" in her best The Grownups Are Talking voice."

"So I turn around, set my window cleaning tools down deliberately and carefully, take one of my cards out of wallet and said "well ok, but I just thought you might like to talk to the owner instead". So satisfying."


"It was glorious."

"I was the manager at an EB Games back in the day. This was probably about 2000-2001. I was there for the launch of the PS2 and Diablo 2 (two biggest events I can remember)."

"We had an older lady come in one day and wanted to "return" a system she had bought for her son. She claimed he had gotten bad grades in school and was returning it as a punishment. She handed me this ridiculously old and beat up cardboard box. I opened it to find a dirty, dusty, cheeto fingerprint covered PS1. I knew that the original PlayStation launched in 1994 (...and now I feel super old), so what I was looking at in the box was at least 6 years old. I paused, looked back at her, and for whatever reason asked if she had the receipt. She actually did. Sure enough, it had the date printed on it, and it was from some time in '94."

"I still hadn't said anything more, I was just looking at the mess in front of me when she spoke up and said something along the lines of "and I'll just take the cash back, that will be fine." I laughed, which was probably my first mistake, and said "I'm sorry, but I don't think I'll be able to return this, this is six years old, and clearly used."

"She tried to argue that she had bought it here at this store and the manager at the time told her she could return it for "any" reason and went on this crazy diatribe about her kid being bad, etc, etc. It went on for a good 5-10 minutes. When she was done, I just flipped the receipt over and read her the EB return policy. "30 days from date of purchase for unopened merchandise... etc".

"She completely lost it. It escalated so quickly I contemplated calling mall security (ha!) and the police. She wasn't having it. Then I told her she could "sell" the system back to us (it was worth about $40 at the time), which would have given her something, but she wasn't biting on that one."

"She asked for the manager, demanded to see the manager, wouldn't rest until she told the manager how rude I had been (I was pretty much a saint for most of this) and was going to get me fired. I just pointed to my name tag, and in the most satisfied tone humanly possible said "Lady, I AM the manager, and there's no way on God's green earth that I'm returning an opened, 6 year old, clearly used, dirty PlayStation."

"She stormed out, never to be seen again. It was glorious."



"I ran an ice cream shop. I must have had to say "Actually, I am the manager" at least once a week."

"My favorite was this woman I eventually banned from the shop. She would come in with her husband and shitty kids. Then she would try to order a large (three scoops) and ask me to put it in three single scoop cups, but only charge for the large."

"I said no. You either order three single scoops or you order a large. The difference in cost is quite a bit, but it's fairly standard for companies to do it this way. I wasn't having it. She got pissy that I wouldn't do it. First she said "Well the manager let me do it last week."

"No I didn't," I told her flatly.

"Well than whoever was working let me do it and they said they were the manager."

"No they didn't. I believe my workers over you."

"Well I want to talk to the manager."

"I am the manager. You are talking to me. I said no."

"Fine!" And she and her little family stormed out without any ice cream. No skin off my back. She was rude to me and my workers, I wasn't going to let her treat us that way."

"Then she proceeds to call the shop the next day, when I am working again (as the manager, I worked a lot.) She said "Hello, I need to speak to the manager."

"Speaking. How can I help you?"

"I was in there yesterday and some little bitch lied and said she was the manager, but she wouldn't let me get what I wanted..."

"That bitch was me. You're banned from our location. Don't come back."

"Bonus justice boner: She tried to call corporate to report me. Corporate outsources complaints to the manager with the highest rating in the area. Which was me. So when she called corporate to complain about me, she also got me. I wrote up the details of the conversation and forwarded all of her messages to the district manager, and he agreed with my decision and allowed me to send her an email officially banning her from the store."


"On one night..."

"I used to work in the box office for an MLB team. The actual manager was usually extremely busy and couldn't easily respond to issues at 15 different windows, so we frequently pretended to be each other's managers. It was the easiest way to get back up when an annoying customer would not accept one of our policies."

"On one night I was helping a very drunk customer who refused to accept a policy (I don't remember exactly what it was). He asked to speak to the manager, but he and everyone else around me were crazy busy. So I turned my back on the customer, turned back around, pretended to be a different person, and backed myself up. He accepted this without issue and went on his way."


"Worked in retail..."

"Worked in retail, specifically a specialist bra fitting shop. One day I was working the change room desk upstairs, taking bookings for fittings and helping the 10 or so customers in the rooms for people who didn't need a fitting but needed me to just quickly check things sometimes and fetch different sizes etc. It was busy, and a woman came in on the lunch rush and demanded a fitting."

"I politely told her that I was very sorry but all the fitters were booked and with other customers for the next hour or so, so I could help her a bit but can't give 1-1 attention as I'm helping all the other rooms too, so if she wants the full thing she would need to pop back tomorrow or later."

"She flew off the handle, telling me how busy and important she was, that she made a special trip, she can't come back tomorrow, I should help her etc. She was really rude, aggressive and mean. I just politely repeated that I was very sorry but I couldn't help her for the reasons above, we just had no free staff, she ranted a while but then left."

"A few minutes after she went downstairs I got a call from one of the till girls saying a customer was complaining about the young girl on the fitting desk who refused to help her even though she could see spaces on the list, and had been rude and had been swearing at her and wanted to see the manager about it. It should be noted I was about 24 at the time, but looked really young - maybe 18. She clearly had no idea I was the manager. I told the desk girl I would be down shortly."

"I walked down those steps so slowly with a huge shit eating grin to let the horrible woman slowly recognise who I was. When she saw it was me her face was just a picture. I played along asking for a description of the "girl" who was so rude, as that is very much outside our standards I am shocked to hear such a thing happened, I was upstairs at the time and certainly would have intervened if I had heard such a thing etc. Shit eating grin on full power the whole time."

"She had caused such a scene that all the people in the shop were staring at us. So she either had to admit she had been lying and trying to get what she though was some poor shop girl fired, or she had to make up a description with me obviously going to be saying things like "hmm, no one here looks anything like that - try again".

"She just was at a loss for words, her mouth agape gasping for air, bright red, not making eye contact. I forget if she said anything at all but she stood there for a long while, and just left."

"I have never felt such satisfaction as I did walking down those stairs knowing what was about to happen."


What amazing moments from these young entrepreneurs. Do you have similar stories to share? Let us know in the comment section below.

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