Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 46: An Investment Opportunity
Fiction Sex Story: Chapter 46: An Investment Opportunity - Jonathan's business life is booming, but he's also suffering from yet another loss. While he's done his best to pick up the pieces of that sundered relationship, he can't help but feel responsible. However, where two close relationships have withered, another blooms. Violet has transitioned from a badly damaged girl to a vibrant woman. Will he continue to climb this ladder, or will there be another ladder to climb in his future? No matter what, the only direction he plans to go is up.
Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa Workplace
September 1, 1984, San Francisco, California
I had a chance to review Ian McIntyre's business plan for Golden Gate Livery late Saturday morning, after sex and a whirlpool with Deanna. Based on the data he had provided, I decided it was an investment I could personally make. I would need to do a bit of due diligence, but really, that would just involve seeing his bank statements and tax returns to verify the income he was claiming, and his trip logs to verify his customer base.
"How would that work?" Deanna asked after I finished reading and said I was considering investing.
"As a silent partner, I'd take a minority interest and have a claim on the assets of the business in the amount of my investment, guaranteed by Ian McIntyre's personal assets."
"If I understand what you just said, you'd take his house if he defaulted?"
"I could, but unless I felt he had somehow defrauded me or acted with extreme negligence, I wouldn't. The reason I would ask for a personal guarantee is that he's operating as a Subchapter S corporation with passthrough income. It would be fairly simple for him to simply take all the assets and dissolve the corporation. I'd receive a portion of the profit equivalent to the percentage of shares I hold."
"Personally, not through Spurgeon?"
"Correct. I can't even run it through Yūsuke Holdings because the S Corp rules require all shareholders to be natural persons. I wish Wyoming's idea of Limited Liability Corporations would catch on, but until there's a definitive IRS ruling on it, they most likely won't."
"What's the difference?"
"A lot less paperwork and the restrictions on owners are relaxed."
"How much does he need?"
"His expansion plan lists $100,000, which is about right. That would cover the costs of acquiring and licensing the cars, plus a small amount of operating capital to cover any other expenses related to buying the cars and hiring drivers."
"Do you have that much cash on hand?"
"No, but I can draw against my earnings. I'm on track to make at least $400,000 this year, and probably significantly more, based on my success with the Arrow Fund."
"That number just boggles the mind!" Deanna declared.
"You think it boggles YOUR mind, imagine mine! Barring some complete disaster, I'll probably make close to a million bucks next year, not counting the several million in carried interest I'll earn. If the market does what I think it will do next year, my net worth will be north of $10 million on January 1, 1986."
"That is just crazy!"
"TELL me about it," I chuckled. "Shall we dress for the gallery?"
We dressed and went down to the lobby. We had enough time to take the cable car instead of hailing a cab, so we did that, and were admitted to the gallery at 12:40pm, twenty minutes before it was scheduled to open.
"Are you enjoying being 'arm candy'?" Deanna asked with a silly smile.
"The fringe benefits are nice," I replied.
"NICE?!" she asked in mock outrage.
I laughed, "You know I'm just winding you up!"
"And you know I'm responding appropriately!"
"Maybe I'll take the platinum blonde up on her offer if she shows up again," I teased.
"I'm the least possessive girl you know!" Deanna declared.
"None of the girls who are close to me are possessive," I replied.
"Keiko was."
I nodded, "Yes, though even she tolerated Bianca and me making Sofía, and that was before her diagnosis. And you know the context of meeting her."
"Ellie's one, true redeeming quality!"
"Ellie is actually very intelligent and has an innate grasp of financial concepts," I replied. "Her error, if you will, was trying to block Keiko from taking me out of play, so to speak."
"And for that, Ellie is in the penalty box with regard to you getting into her box!"
I chuckled, "Cute."
"Did you notice the tags on my paintings?"
"Yes. All orange. Is that good or bad?"
"Good. The paintings are intentionally priced higher than Ms. Anglim considers the 'correct' price, if there is even such a thing. In shows such as this one, the reserve is set around the price she believes is their 'correct' value. Everyone knows the game, so there will be multiple bids on each painting."
"Why do I hear air quotes around the word 'correct'?"
"Because it's impossible to price artwork. You know how you say the bid/ask prices are, in effect, random? Pricing art is even more random than that. At best, a valuation is based on what the appraiser believes someone would pay for the painting if it were to be offered at a public auction. The term 'priceless' does not mean there is no price — it means you cannot set one by any rational or logical means. Think about the conversation we had about what it could take for you to give a blowjob. There is a price, even if it's not something that could be priced."
"That reminds me of the joke Kristy told about the guy asking a girl if she'd have sex with him for a million dollars, and when she said 'yes', he asked her if she'd do it for $10, and she responded, 'What kind of girl do you think I am?'. He responds that they had already established that, and were negotiating the price."
Deanna smiled, "That goes to the theory that literally everything has a price — that is, something of value that can be exchanged — even if the price cannot be met by the interested party. The two years Teri spent trying to get you to pay her price for her cherry is a perfect example!"
"You make a surprisingly good capitalist for an artiste," I chuckled.
"You know I'm a libertarian!" Deanna replied. "But I will absolutely admit most of the students at the School of the Art Institute are pretty far to the left on the political spectrum.
"Do you agree with the idea that something is only worth what another person is willing to pay for it?"
"Isn't that a tautology?" Deanna asked.
"Maybe," I replied. "It's possible for me to place a value on something nobody is willing to meet. Whose value assessment matters at that point?"
"The one who refuses to sell at the offered price because he values it more than whatever he could exchange it for."
"Which goes right back to the question of 'priceless' — a thing which has so great a value to the owner he or she is not willing to part with it."
We had to end the conversation because the gallery doors were opened and the guests who were invited so nobody caused a social faux pas, arrived a minute later.
"I didn't ask this at the previous auctions, but how does someone know they've been outbid?"
"Do you see the woman in the blue dress with the clipboard? She has the current high bid for each item on her clipboard. The usual strategy is to return on Sunday to either raise your bid or buy the piece outright. Of course, you run the risk of someone else buying it outright, but given the displayed prices, I doubt anyone will do that for any of my pieces because I'm unknown and from Chicago."
"Being from Chicago matters?"
"In the sense that I'm not part of the art scene here? Yes. Nobody can reasonably invite me to a cocktail party to show off my work. If I had a name in the art community, then it would be different."
A well-dressed man whom my mom would have called debonair came over to speak with Deanna. He was engaging and charming, and the gorgeous girl on his arm didn't seem to mind his obvious flirting with Deanna. After a few minutes of banter, she stepped slightly away from him and closer to me.
"What do you do besides look good standing next to the artist?" she asked in an engaging but quiet tone.
"I'm an investment manager at a financial services firm in Chicago," I said. "What do you do besides look good on the arm of a man in an art gallery?"
She laughed softly, "Touché! That is actually what I do! This is work."
I nodded, understanding what she meant — she was an escort. And that explained why she wasn't bothered by the flirting.
"Only art shows?"
"Any social event — symphonies, operas, galas, and that kind of thing. Places and events I'd never get into otherwise. Mind if I ask how old you are?"
"Twenty-one," I replied.
"Wearing a $1000 suit? Impressive! You must be very good at your job!"
"What would you say if I said something like that about the very chic dress you're wearing?"
"I'd take it as a compliment! I am very good! I'm also a very good student. I'm pre-med at Stanford and haven't had to borrow a penny. Mind if I ask about your relationship?"
"Patron," I replied.
She smiled, "Which is why you didn't react to my revelation."
"I wouldn't have anyway. My ethical system allows for any behavior that does not intentionally harm another person."
"Katherine Miller."
"Jonathan Kane. Is that a nom de guerre or your real name?"
She laughed, "A riff on 'All is fair in love and war'?"
"Just trying to be lighthearted instead of saying 'pseudonym' or 'stage name'."
"My real first name, but my mom's maiden name. As I suspect you deduced, I might want to disguise my identity. I plan to Match out of state when the time comes. Do you know what that is?"
"Yes. A close friend is married to a second-year ER Resident at Cook County Hospital, and another close friend is pre-med."
"Drumming up business, Katherine?" the man she was escorting asked.
Katherine laughed softly, "You were busy chatting up the artist!"
She opened her clutch, extracted a card, and handed it to me.
"If you find yourself in San Francisco and need a companion for an event, call!"
I accepted the card, and she and the prospective buyer walked away.
"Escort?" Deanna asked.
"Pre-med and paying her way through school," I replied. "Did he close the deal?"
Deanna laughed, "I have $100 that says he's gay, and she's his beard."
"Beard?"
"Cover. He's the CEO of an insurance company, and even in San Francisco, being gay won't go over well for someone in that role, not to mention having to interact with people from places like where we grew up."
"I have to ask what makes you think that?"
"I've seen it before, and he fits the profile – a good-looking guy in his forties, never married, gorgeous escort, flirting, but almost trying too hard, if that makes sense."
I shrugged, "My sum-total experience with gay men is the Boys, and they're all out."
"Men you know are gay; I bet you anything you care to wager that at least one of the licensed guys at Spurgeon is gay and completely closeted."
"He'd have to be," I replied.
That was the last private conversation we had, as more and more people came into the gallery and engaged Deanna in conversation. By the time the gallery closed, Deanna had spoken to at least two dozen art collectors, and I'd actually handed broker cards to a pair of prospects who gave me their cards and asked me to send them the prospectus for my fund.
"Have you looked at the bid sheet?" I asked Deanna once we were in the cab, which would take us back to the Mark Hopkins.
"No. But they all hit the reserve, which means I'll make at least $1600 after commissions."
Which, if I subtracted the cost of the airline tickets, the hotel, and meals meant a profit of around $400, and that didn't account for Deanna's time.
"I can see why the stereotype 'starving artist' developed," I observed.
"This wouldn't be possible without a patron," Deanna said. "It really is something that needs to come back into vogue."
"Why did it die out?"
"A mix of things," Deanna replied. "The Roman Catholic Church reduced the art it commissioned, public treasuries did not pick up the slack, and private collectors began purchasing completed works rather than commissioning them. Patronage had its ups and downs, but what put the nail in the coffin was the Scull Auction in 1973, which created a market for contemporary art.
"That was both good and bad, with the bad being artists making a pittance compared to collectors and speculators. It made Robert Rauschenberg and Andy Warhol household names, but they felt ripped off by Scull, who had paid $900 for Rauschenberg's Thaw, which sold at auction for $85,000 fifteen years later. Those sky-high auction prices changed how everyone thought about contemporary art."
"Wouldn't that have ultimately helped them? I mean, if a Warhol piece went for a hundred times its original price, wouldn't Warhol be able to get more for his pieces?"
"Eventually. What mostly happens is that paintings from young, up-and-coming artists are bought dirt-cheap, held for a time, then sold at auction, with the artist seeing nothing and often no longer working. I'm lucky to have found a patron before my career really started, and I've had some help from professors at the School of the Art Institute. Most artists have neither. It applies to other creative fields, too — what chance would CeCi have had if you hadn't greased the skids with your Hollywood contacts?"
"A tiny one, at best. We all know the stories about trying to break into Hollywood, where the most important line you have to learn is 'Do you want fries with that?'. We hear similar stories about trying to break into the music industry, too."
"Exactly. People who have patrons or know someone have a much better chance. You did something similar with Spurgeon and Matheson, and Jack, Bianca, and Violet are doing the same with you. All of them have the necessary skills, but without a mentor or patron, they wouldn't be where they are now. Could they have achieved that on their own? Maybe in a much longer timeframe. The same is true for you."
I nodded, "Ultimately, I am where I am because my uncle is friends with Noel Spurgeon. Well, that and my own initiative and determination."
"Which is true for the others as well; CeCi won't make it just because you called in a favor — she'll have to prove she can do it, and probably have to do it twice as well as a guy because Hollywood is every bit as sexist as Spurgeon Capital."
"That is something I would never countenance at my own firm."
"I'd be shocked if you felt otherwise. Have you given your exit strategy more thought?"
"Yes, and I keep coming to the same conclusion — there isn't one at the moment if I want to stay in the industry. That said, as you know, I'm taking every possible step to ensure I have diversified investments and that my wealth is not completely tied to Spurgeon. It's not just property, either. I'll very likely provide seed capital to Erin Laning for her desktop publishing business and provide expansion capital to Ian McIntyre for his business. One goal of my trips to New York was to find other investments I can make, as well as raise capital for my fund."
"You know we'll all help in any way we can."
"I very much appreciate that."
When we arrived at the Mark Hopkins, we went up to our room, got ready for bed, then climbed in together.
"What can I do for you tonight?" I asked.
"Just once, gentle, then sleep, cuddled together.
September 2, 1984, San Francisco, California
On Sunday morning, we had breakfast delivered by room service, then took a cab to Golden Gate Park. For me, the most important thing to see was the Golden Gate Bridge; for Deanna, it was visiting the de Young Museum. We couldn't stay as long as she would have liked because we had to get to the gallery for the show's closing day.
"What do you say we come back here tomorrow before our flight?" she asked as we walked towards the street where the cab had dropped us off.
"I'll leave that up to you," I replied. "I did promise to take you to as many museums as you wanted to see."
"I figure the best time to do that is after I graduate. Maybe the Summer of '86?"
"Map out a plan, and I'll have Barney at Windy City Travel create a travel itinerary for us with top hotels, great restaurants, and, of course, the museums."
"There is one fly in the ointment," Deanna observed.
"Violet?"
"Yes. If we don't go before January, it complicates things."
"I honestly believe you'll find Violet amenable to our relationship. I can't guarantee it, obviously, but she is very different from how she was even three months ago."
Deanna laughed softly, "Losing her virginity did result in a very different person."
"I'd counter that and say the Violet you are seeing is the real one, and who she would have been absent her parents' abhorrent behavior."
"I'd say you're probably right."
"In January, when we come back from Hawai´i, have a private conversation with her, explain exactly what you want, and see what she says."
"You think I should approach her before you two have your conversation?"
"I think you asking her to sleep with me in the future is very different from me asking to sleep with you. I know Bianca is going to have a conversation with her, and I'd put heavy money on CeCi having one, too."
Deanna laughed, "And you get your fantasy future!"
"No, not really," I replied, my voice tinged with melancholy.
Deanna frowned, "Sorry. I shouldn't have said that."
"It's OK. I know what you meant, but I think you know why I reacted the way I did."
"I do, and it's the exact reason Violet doesn't think you're ready for the conversation. It's not Saint Martin, it's not Hawai´i, it's Keiko. You aren't ready to give your heart, or at least a part of it, to anyone."
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