“I’m Not a Natural Salesperson—But At Least I’m Funny”

Because nothing closes a deal like self-deprecating charm and a well-timed joke about

“How to sell the rest you deserve at The Virginia May.”

Let me start with a confession that will probably get me banned from every Bed and Breakfast motivational thread ever:
I am not a natural salesperson.

I didn’t pop out of the womb asking the doctor to upsell me on the deluxe swaddle package. I never convinced my third-grade classmates to buy into my lemonade stand in the dark of a cold Canadian, December day.  And I’ve never described myself as someone who can “sell anything.”  I did however emerge into the world with quite a gift of fast quips, levels of sarcasm that often are to my detriment, and a fast brain that only sees good choices long after I have made a few (ok many) questionable bad choices. 

I am mostly in awe of those who have the hustle to sell.  (cue the 70’s The Hustle with the predominant piccolo,  drums, a guitar and a few horns).

But you know what I am?
Funny.

Like, actually funny.  But funny in a way that makes people lower their guard, laugh unexpectedly, and then say, “Okay, fine, add the charcuterie board.  For this I am thankful, because in my head I am thinking “awesome, this goes towards paying for my mortgage this month,” because small business is no joke.  

Here is another confession– this small business gig is harder than I thought.  My charm only goes so far.  

Year three of business, and I am still working my way through how to sell rest and relaxation on my website.  Once the guests are out here, all is well that ends well as Shakespeares mused.  Everyone is happy. Breakfast is delicious, the deer,  the quiet of the street, the crepes. God blesses the crepes more than Texas.  Is that sacrilegious?

The way of the  world is websites, SEO, sales pitches, vacation platforms, and all the magic of the internet.  So how does one get heads in beds as the industry proverbial phrase goes?

I constantly get emails from companies telling me my website looks “good,” but it doesn’t rank high enough on the elliptical, (or whatever it is) so therefore I need their expertise.  And that for the low price of 408,000 thousand  per month with a 12 month contract, my first born and my sweet dog, the innards  of two toads, one rat snake, and my credit card, I too will be wheelbarrowing money around the property.

I wish the one liners that I could use were as easy as this:

We only have 3 left.” 

“This price goes up Friday.” 

“Everyone’s getting breakfast. You don’t want to be that guy that misses out do you?”

It has been a long few years of  researching how to sell my “product,” or my “brand.”

Here’s where it gets fun. Humor isn’t just for making people like me. It’s for making people see the problem they’ve been ignoring.

Sadly, humor is how my brain works when I am trying to work through problems. Everything becomes a scenario that is so over the top that inside my head it is just a constant stand up comedian sketch.

"Let me ask you something: when was the last time you felt genuinely rested? Not 'I got six hours and a coffee' rested—but like, 'my soul just took a bubble bath' kind of rested?"

[Pause. Let that land.]

"That’s exactly what The Virginia May is designed for—except without the loofah."

I am not mocking them. I am mocking the chaos they’re surviving in. And suddenly, my product isn’t just a solution—it’s salvation.

OR

“Here’s what’s not at The Virginia May: conference rooms, urgency and people saying “let’s circle back.” At that point, if I could, I would like to offer them a yearly membership, or a free juicer, or perhaps something that improves their credit score like a bag of tongue depressors. Or face cream. 

"The Virginia May isn’t just a place to stay—it’s where stress goes to die. It’s rest, redesigned. Think soft sheets, slower mornings, warm lighting, and the kind of silence you didn’t know your nervous system needed."

As a non seasoned salesperson, could this  be my opening, and my mission?  To identify the itch, then become the scratch? I don’t have a  manager, the classic bait and switch tactic  that I can go and get.  The one who comes back smooth as fine pinot noir wine,  the “closer” of the deal.  Nope. Just me. And my natural charm. 

“At The Virginia May we don’t fix burnouts.  We prevent it.  By doing … nothing.  Beautiful, luxurious, soul-repairing nothing.  Doesn’t that sound like a weekend of bliss?”

“Let’s be honest: you’re not just “a little stressed.” You’re one group chat away from faking your own disappearance.  Your brain’s buffering, your body’s buzzing, and your calendar has more color blocks than a toddler’s Lego set.”  

I have been bamboozled several times by the ardent salesperson who was just a hair smoother than me. 

Take for instance the dude who sold me the dream of new cast iron pipes I never knew I needed.   That will go down as the biggest bamboozle on record thus far in my sordid spectacle of a life.  It practically pays for itself.  Oh didn’t it….”hell hath no fury like a scorned woman.” 

 I have seen behind the curtain. I have been hoodwinked. I have eaten the overpriced poisoned fruit  of betrayal, and drank the koolaid without the needed vodka. 

But here’s the upside– I   know exactly what not to do. I have been sold to. Hard. Aggressively. Uncomfortably. And now I get to be the refreshing opposite. So I am learning to embrace this new world order of sales.  Be the anti-bamboozler I tell myself. 

“Look, I’m not here to bamboozle you. I’ve been bamboozled. It left emotional scars and two years of monthly payments. I’m just here to help you make a decision about the weekend. Or the week. Why not stay a week, or better yet, a month? 

A weekend is cute. A week is smart.  But a month?
That’s a lifestyle choice. That’s a full-blown “I no longer participate in burnout culture” declaration.  Why not choose a long rest over a long weekend?  

And to quote the funniest salesperson I know: “salespeople never quit, they keep going until someone buys their stuff.”

I think I found my motto. ;)