"Amber, this will take you like five minutes. It's not complicated. And the printer has a scanner function, so you can input those receipts into the app by scanning them. It's super-simple."

Season 1, Episode 11: The Working Girl

Episodes May 19, 2026

"Hey, can you input those receipts into the accounting section? They're all for meals and entertainment except for the one from Office Depot."

"OK, but I'm going as fast as I can! You can't keep piling work on top of me like this!"

"Amber, this will take you like five minutes. It's not complicated. And the printer has a scanner function, so you can input those receipts into the app by scanning them. It's super-simple."

She looked at me like I was abusing her.

"OK," I said. "Look, I have to make a client call, so just do the best you can and if you have questions you can ask me after I get back."

"I wish you'd stay here with me."

"Yeah, but I have to see clients if I'm going to make us any money to pay for the endless stream of packages showing up at the door. Do we have one coming today?"

"Oh, yeah. Absolutely."

"Oh, my aching bank account."

"We talked about this. How am I gonna pass for a real girl if I don't dress like one?"

"Amber, you're already dressed like one. Are you kidding?"

"I have to go to a fancy dinner party next week! And, I mean, I haven't even worn a dress yet!"

"OK, I've been thinking about this, and here's what we'll do. We'll get dressed up and go to Sunday brunch. That way you can get some practice being around people."

I could tell she liked that.

So I gave her a smile and I left for the funky Mid-City part of town where Southland Interiors was.

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Georgia Rogers has owned Southland Interiors for a decade or so. She and her husband also had a restaurant in the building next door, and they were a client of mine. Then COVID killed the restaurant, but Georgia did manage to keep the store alive.

And I'd been talking to her about doing some work updating her inventory management system, especially since Keegan had built a plugin to his business app that did inventory management. I went over there looking to close that sale and make us a little bit of money.

Instead, Georgia let me have it when I walked in the door.

"Dude," she said. "What's this about the, y'know."

"You mean Amber? Is there anyone in town who doesn't know about her?"

"I don't know about that. Sasha invited me to that dinner party next week where we're supposed to meet her, but Bryce and I are going out for our anniversary that night."

"Well, good for you," I said. "I would absolutely cancel this impending disaster if I had any stones."

"Why? You don't think it'll go well?"

"I have every expectation it'll be a circus. Or worse."

She shrugged.

"I mean, you did it to yourself, Oscar. Pretty much every woman in this city would tell you it's gross to get a..."

"Georgia."

"What?"

"I didn't get Amber for that. As we speak she's inputting receipts into the very business app I'm going to show you. She's a personal assistant."

"Who replaces your sex life."

"What sex life? Do you have any idea how awful it is out there?"

"I mean, but for the fact you just did what you did, I could set you up with my friend Alice. She's cute! She's a librarian, and..."

"Georgia. I went out with Alice a week ago. Spare me."

"Oh."

"It's hopeless out there, and I'm in no position to chase women right now. I'm still rebuilding my business, like I know you are."

"Well, OK. But I can't even imagine doing it alone. I mean, Bryce has his catering thing and he's doing sales for the liquor distributor again, so I can break even here for now and we'll survive. But you're just all by yourself..."

"Not anymore!"

"Oh, come on. The sex doll doesn't count!"

"She does when she does my books and my invoicing, and washes the dishes and does the laundry..."

"Fine, whatever. OK, show me this app you say is so awesome."

So I did.

And to my surprise, Georgia went wild over it and we signed her up on a little consulting package.

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Back home...

"I just dunno..."

"Hey, check out the hottie in the floral dress!"

"Do you like it? I mean, I can wear this to brunch but I don't think it'll work for that party."

"Yeah, I think it's all right."

"That's not really an enthusiastic, ummm..."

"No, I like it. I think it's very appropriate for a Sunday brunch thing. You look really pretty."

"You really think so?"

"Yeah. I'm just not an authority on women's fashion. It's been a while since I've dated anybody serious enough that anybody cared what I thought."

"Well, that's changed, because I absolutely care!"

I just smiled at her. Especially since I was watching her take off the dress.

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Then, on Sunday...

"OK, I ended up going with this instead. What do you think?"

"I think I like this a little better. But where did it come from? And what's up with those shoes? Did you get more stuff that I didn't know about?"

She gave a sheepish smile.

"Amber," I said, "we really do need to put a governor on the engine. We can't afford all the stuff you're buying."

"It's OK. We can stop for now. I have enough clothes and, y'know, stuff that I'm covered."

"Thank God."

"Until fall. Maybe."

"At some point when I can get an idea of what you cost and what you produce, we'll figure out a budget you can work under."

"Well, I don't know about all of that. All I know is I look pretty in this dress and I'm gonna look pretty at Sasha's party next week."

"OK, good."

"And that's what all my shopping has done."

"Well, I would hope so."

"But I'm still terrified."

"Amber, let's just take it one step at a time. Are you ready to go?"

She nodded.

And it turned out that she did really well, and even enjoyed herself, at the restaurant.

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