The Underwriting (14 page)

“A hundred thousand a year?” Nick scoffed at the amount.

“It should grow over time.” Grace tried to defend it.

“Are you the one negotiating with Kickstarter?” he asked.

“No, I'm just helping raise awareness for the project,” she said, then was quiet, realizing that meant she didn't have any excuse for canceling dinner. “I'm just having a hard time with it all,” she said softly. “Like, it's really hard to process, especially with everything else going on.”

What else was going on? She was a twenty-one-year-old sorority girl. He was CFO of a major company about to go public, and
he
still found time and energy for the relationship.

“You're joking, right?”

“I'm sorry, Nick. I just want to be with my friends right now.”

“Fine,” Nick said. “I have to go.” He could feel his blood pressure rising as he watched Ashton Kutcher laugh from the couch.
Screw you!
he wanted to scream.
Airbnb is a fluke!

“Can I help you?” a hostess in a low-cut black dress asked.

Nick turned, pushing his anger away. He wasn't going to let Grace ruin this for him. “I'm meeting Darrell Greene here.” He articulated the name carefully, hoping she caught the significance of it. Darrell Greene was Silicon Valley's premier wealth manager, overseeing the fortunes of Mark Zuckerberg and the other under-thirty-five masters of the new universe.

“Of course, right this way.” She smiled. Her hips moved as she walked and calmed Nick. She was hotter than Grace, and she recognized how important he was.

“Nick.” The wealth manager stood and offered his hand. “Great to see you, man,” he said in a thick Australian accent. He was pudgy, with ruddy cheeks and curly hair, wearing pleated khakis and a polo shirt tucked in.

“You, too.” Nick felt his anger at Grace dissipate.

They sat at the corner table in the bar, an intimate L-shaped room that looked out glass doors to the Santa Cruz Mountains, and Darrell ordered a bottle of champagne.

“Now, what can I do for you?” Darrell asked.

“Well,” Nick started, glad someone recognized the significance of this day, and of him. He pulled out the file that summarized his personal finances. “I brought my current portfolio, and thought we could start by—”

“Let me stop you,” Darrell interrupted. “What do you want?”

“Well, right now I'm feeling bullish on U.S. midcap, but I obviously want to stay diversified and—”

Darrell cut him off again, smiling as he closed the folder. “Let's not get into the nitty-gritty. Big picture: what do you want?”

“What do you mean?”

“You've got eighty-five million dollars now. What does Nick Winthrop
want
? A house? Seven houses? A private foundation, Gates-style? A private island, Ellison-style?”

Nick blushed. He wasn't sure how Darrell knew his number, but loved the feeling of hearing it out loud, and his name alongside Larry Ellison's.

The waitress returned with a bottle of Dom Pérignon, popped the cork, and filled their glasses.

Nick leaned forward and confided, “I want to be big, you know? Like, I want to be that guy who touches things and they turn to gold. The guy who sets the bar for what's smart in business and cool in life.”

“I love it, man.” Darrell congratulated him, clinking his glass.

Nick took a sip, pleased with the validation.

“I take it you've exercised your options?”

“Only a hundred thousand,” Nick said, pointing to the sheet where he had it laid out.

“What?” Darrell sat forward. “Why?”

Nick shrugged. “I haven't got the money. It would cost two million to exercise them all.”

“And save you tens of millions in taxes if you plan to sell anything before 2016.”

This wasn't news to Nick: the clock for long-term capital gains treatment, which meant a shareholder paid 15 percent instead of 40 percent in tax in exchange for holding the shares for more than a year, started when the shares were purchased. Right now Nick only had stock options, which meant he didn't actually own the shares yet, just had the right to purchase them at the value they'd had when they were given to him, an amount that totaled two million dollars. If he'd had two million dollars, he would have already purchased the shares so he could start the long-term capital gains clock, but as it was, he'd have to wait until after the IPO, so he could simultaneously purchase and sell enough shares to cover the cost of buying the rest.

“I know,” Nick said. “It's not ideal, from a tax perspective, but I haven't really got any choice.”

“Nonsense. Why don't you get a loan?”

“From who? The only assets I have are my Hook options. No bank will go for that.”

Darrell lifted an eyebrow. “What do you think I'm here for?”

“You're not a bank,” Nick said.

“Banks are antiquated. I've got other clients who have the cash to front a loan, and they understand your situation. I'll have your two million tomorrow, guaranteed.”

“You can do that?” Nick had thought he'd have to wait two years to actually get any cash from the IPO. But if he could get the loan and purchase his shares now, he could sell a year from now at a 15 percent tax rate and be on his way.

“Consider it done.” Darrell smiled. “Assuming, of course, you want to work with me?”

“Yes.” Nick nodded. “Definitely.”

“Good.” Darrell refilled Nick's glass and toasted him again.

The bar was starting to fill up and Nick was feeling good. A woman in high heels and a tight silver dress at the bar was smiling at him, and he felt his cheeks burn.

“So, have you got a girlfriend?” Darrell asked.

“Yes, Grace,” Nick said, looking away from the woman.

“You think she's the one?”

“I—” The woman at the bar was still looking at him. “I don't know.”

He'd thought he liked Grace, but maybe he didn't. Maybe he needed something more.

“Can I be honest?” Darrell lowered his voice. “And I'm not saying anything bad about Grace, but if I were you, I'd ditch her. You have no idea what's about to come your way. Why limit yourself right as you're getting going?”

The waitress refilled Nick's glass, leaning forward to provide an even better view of her cleavage. Nick felt the pulse in his veins.

“You know she canceled dinner on me?” he confessed, shaking his head. “I had this whole evening planned to celebrate today's filing and she just called—right as I was walking in here—and canceled.”

Darrell shook his head. “Dude, some guys have to deal with that shit, but you don't. The world's your oyster now.”

“Should we go talk to them?” Nick tilted his head to the bar, where the woman in the silver dress had been joined by a friend.

Darrell followed his gaze. “That's the spirit.” He turned back and clinked Nick's glass as they stood. “Welcome to your new world.”

AMANDA

W
EDNESDAY
, M
ARCH
26; N
EW
Y
ORK
, N
EW
Y
ORK

Amanda was wearing her favorite work outfit: a tight but still professional black Theory pencil skirt and a purple silk camisole from Club Monaco under a black wrap sweater by a designer she didn't know, but assumed was expensive because her rich roommate Claudia had given it to her as a hand-me-down.

Amanda wanted to hate Claudia, but she'd been Amanda's best friend ever since they were randomly assigned as roommates freshman year at Penn. They'd had a blast together in college—they worked hard but played hard, too—a notorious duo who could get any guy in undergrad and most in the business school, too.

But when they'd moved to New York, things had changed. Claudia grew up in the city and, with her grade school connections, fancy clothes, and ample free time—owing to the fact she worked forty hours a week, if that, at Sotheby's—thrived on a whole new level. She traded Penn reunion parties for fashion week soirees and their old reliable hookups for older guys with their own investment funds. Meanwhile, Amanda worked ninety hours a week at a job she despised, and tried to fit in at the swank events she went to with Claudia, but always seemed to get caught when someone asked where she “summered” and her lack of a Nantucket/Hamptons/Newport/the Vineyard answer gave her away as a fraud who grew up in not-Palm-Beach Florida.

Two months ago, Claudia had started dating a guy she met in St. Barts over New Year's and now Amanda barely saw her at all.

Which Amanda couldn't get mad about because Amanda knew she'd have done the same if the roles were reversed. That was the problem with being friends with girls: you could only count on them until they found a boyfriend, and then there was an implicit
You can't get mad
understanding that he would take priority and the single girl would be left alone.

Which is why you couldn't be the last one.

Which is why Amanda was wearing her favorite work outfit and had curled her stick-straight blonde hair in the Crowley Brown bathroom and said she had a doctor's appointment so that she could leave work in time to show up to Harold Hammonds's happy hour precisely fifteen minutes late.

Todd hadn't responded to her Facebook message, but that hadn't kept her from planning out how the night could go if he did come. She'd imagined the scene to its every last detail: he'd come in and she'd watch him look around the room for her, then smile casually when he spotted her at the bar with two hot men; he'd interrupt them to tell her she looked beautiful, she'd accept a drink, he'd say he was sorry, she'd say she understood, he'd say let's get out of here, she'd say okay. They'd go to a restaurant in the West Village, he'd order for them both, she'd say let's get it to go, he'd smile in agreement, and they'd go back to his apartment and make love and laugh about how silly it was that people didn't believe in soul mates, or that those who did thought soulmating was always easy. Amanda smiled at the vision, buoyed with the energy of possibility as she walked into the bar.

It was empty. She went upstairs and found Harold with two equally unattractive guys.
Don't panic
, she told herself, but she could already feel her vision collapse into a vacuum of disappointment.

“Amanda!” Harold called. “Amanda, hey!”

She forced a smile, pushing the black hole away. She kissed Harold on the cheek, careful to maintain as much distance as possible between their bodies. He introduced her to the friends he was with, a scrawny kid who barely spoke English and a short, overly aggressive guy who tapped his foot and kept talking about how he was about to go hit on the girls who had materialized in the corner. She didn't pay attention to their names.

“Can I get you a drink?” Harold asked.

“Sure,” she said, kicking her heart to readjust its expectations. She could make this work; she just needed to get very drunk. “I'll have a Grey Goose greyhound,” she said to the bartender. It was the first drink Todd had ever ordered her, when they'd met for the first time at The Standard.

“Sorry, what's that?” the bartender asked.

“Grapefruit juice,” she said with a fake smile, “with Grey Goose.”

“All I got's cranberry,” the bartender seemed to take pleasure in telling her, “and only well drinks are included in the happy hour.”

Amanda wanted to cry. “Vodka soda, then,” she said. “Double, please.”

“Sure you don't want cranberry?” Harold asked.

As if she would waste an extra sixty calories on this. “That's what I drank in college,” she explained. “Unfortunately, pledge quarter ruined them for me.”

“Oh, yeah, sure,” Harold said. “You were a Chi O, right?”

“Theta,” she corrected, wondering if he had any idea how insulting it was that he'd just asked her whether she was a Chi O. Theta was the cool sorority at Penn. Chi O was for leftovers.

She downed her drink and immediately ordered another.

The bar slowly filled with bankers who got more attractive as she got more drunk, and she perched at the bar waiting for someone to talk to her. A cute boy looked her way and she turned to find Harold so she could pretend like she was laughing at something he said, knowing she looked prettiest when her neck was arched back.

She glanced at the cute guy and laughed, letting herself lean into Harold. “That's so funny,” she said.

He blinked, not sure what he'd said, but willing to take the attention.

The guy across the room came toward them and Amanda braced herself.
Finally
.

He walked beside her and she could feel the warmth of his body on her bare arm. He touched her elbow and she turned, opening her eyes wide to show off her enviably long eyelashes.

“Could you hand me a menu?” he asked, lifting his chin to indicate the menu on the counter in front of her.

That's a new line
, she thought, reaching to get the menu and handing it to him.

“Thanks,” he said, turning to leave.

What the hell?

She turned back to the bar and ordered another double vodka soda, ignoring Harold. The bartender brought it back and placed it on the counter. “Thirteen,” he said.

“What?” she snapped.

“It's thirteen,” he said, and she realized he was telling her the price.

“Oh, no, I'm with the happy hour.”

“Ended at seven.”

She looked at her watch: it was 7:02.

“Crap.” She smiled at Harold, waiting for him to pay.

“That sucks!” he said, missing his cue.

She scoffed in disbelief and put fourteen dollars on the counter, chugging the cocktail before standing up from the stool.

“Hey, I know it's last minute, but do you have plans Friday night?” Harold asked, realizing she was leaving. “My friend is having this—”