The Unexpected Mentor: How My Sugar Daddy Helped Shape My Success

I grew up in a ski resort town, which is kind of a weird concept for people to grasp if they’ve only ever been to one on vacation. Basically, the town exists on tourism. You work your tail off for five months over the winter, and then the town is a ghost town for three months, and then you’ve got three months of summer vacationers, and then it’s another one or two months of nothing again.

Living and working here is like the epitome of “get while the gettings’ good” or “make hay while the sun shines,” if you’ve ever heard those sayings. But, in less euphemistic terms, every year is hopefully 8 months of great pay and inevitably at least 4 months of layoffs and penny-pinching. Most people would love to be able to save, but ya know. It’s a struggle.

And everyone who’s stuck around for more than two seasons has learned how to adapt to this way of life. But it’s certainly not an easy way to live. And it’s honestly even harder when the tourists you’re catering to are all ultra-rich and often rude and don’t really understand that a good night of tips is what gets us through the so-called shoulder season.

Now that we’ve got the context set up, let me introduce myself. I’m Sylvia, and I actually got myself out of that perpetual loop of financial insecurity. And it all started when I spilled a drink on the man who would become my sugar daddy.

I had seen him come into the restaurant where I bartended quite a few times, always with his buddies. They always got a booth in the back, so other than making their drinks, I really had no contact with him. But this was the year that I had made it a personal goal of mine to start making better drinks (even though the owner of the bar was stingy and only ever bought the worst-quality ingredients). And, my practice must have been paying off because Mr. Future SD came up to the bar to ask who had made his drink and pay his compliments while asking for another round. And, this was the first time that I was able to see him up close, which was kind of a shock because he was way more handsome than I had realized.

And now look, I don’t mean to come off as arrogant, but this isn’t the first time that a patron has asked me out (a guy likes a lady bartender, it’s kind of a thing). But it was the first time that a patron asked me out by saying the words,

“ I hope you don’t mind me just coming out and saying this, but I’m a sugar daddy. I like taking girls out for a nice dinner and great drinks, and then if something comes of it, amazing. If not, then we’ve both had a really nice night. I don’t want you to say anything now, I’m just going to give you this napkin with my phone number, and you can reach out if you want. I leave on Thursday.”

And this is the moment that I fully embarrassed myself because as I was reaching across the bar to hand him his drink and take the napkin, my brain misfired (I mean, it was a shock what he had said) and the drink slipped out of my hand, bouncing perfectly off of the edge of the bar and onto his pants. I thought I would simply perish from the embarrassment. At the very least, I was expecting a reaming from him and probably my boss. But instead, he laughed, gave me a wink, and said, “Well, now you owe me a drink.” And he went over to say goodbye to his buddies, and then he left.

Long story short, the next night, I found myself raiding his mini fridge and making him the best hotel cocktail this town had ever seen. I admit that I probably wouldn’t have called him if I hadn’t felt bad about the drink, but now I was surprised to find that I was actually enjoying myself. We got to talking about our lives and plans for the future. I told him that someday, I’d love to own my own speakeasy-style bar, where I could make actually good drinks and charge ridiculous prices for them. But it was hard enough to get through the end of the year with even a little bit of savings.

“If life is so hard here,” he asked me. “Why don’t you leave?”

Typically tourist perspective. I told him that even though it was hard, I loved living here. I had never thought to leave.

He took a moment to soak this in and then said, “Okay, well, why don’t you leave only for the off-season?”

For what, I thought, to be broke and jobless somewhere else for two months?

“Look,” he said. “I have an Airbnb that doesn’t get many rentals during the off season. You can stay there, I won’t charge you rent. You’ll have your own space, and I won’t even have a spare key. And all that I ask is that you let me pay for mixology courses and that you work as a private bartender when I have parties at my place. Whenever you want to come back here, you come back.”

I asked him what, exactly, was in it for him, and he took a sip of his drink.

“Honestly? The best cocktails I’ve ever had in my life. And, maybe a date every once in a while.”

Sure, it wasn’t a conventional setup. And I wasn’t naive enough to think that it couldn’t blow up in my face. But I also knew that I had enough savings to keep my gas tank filled in case I ever needed to get out of there. Which, thank goodness, I never did.

Within three years, I had quickly breezed through the mixology course (most of it was online anyway) and then set my sights on online business school. My sugar daddy was on board immediately, as long as I could still commit to bartending his frequent private events. He even bought a brand new desk and office chair to put in the Airbnb so that I could study.

I’m not going to lie and say that I now own my own speakeasy or anything like that. But, I’m definitely on the way towards that! I save as much as I can during the busy season here at home, and my costs are virtually nothing when I’m staying at my sugar daddy’s place. And, over the years, he was always there to answer any small or large questions I had about where I should take my career. He even helped me invest some of my savings so that when I’m ready, I can actually open up a place of my own.

I would honestly go back and spill a drink on that man without hesitation. It changed my life.