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The Underwriting

Michelle Miller

'You are such an asshole.' Her face had gone from red to white as she pulled her naked legs from under the sheets. Retracing last night's steps from the living room to the bed, she collected the trail of discarded clothing in her arms.

Todd reached for the remote and turned on MSNBC, hoping the sound would drown out the awkwardness. He hated morning awkwardness. The girl came back into the room and started rummaging through the sheets for her underwear.

'I just don't ...' she started, looking at him. 'I just don't understand why you're so afraid of commitment.'”

'I'm not afraid of commitment,' he said simply, pretending to be absorbed in the television, where two commentators were discussing the latest scandal at L.Cecil, involving traders who allegedly peddled two hundred million dollars of shares they knew were overvalued to unwitting investors. Todd made a face at the television: that better not affect his bonus.

The girl pulled her skirt over her thin hips and refastened her push‑up bra; she had a nice rack, but her thighs were too big and she looked like the type who was going to balloon when she hit thirty-five. She was an 8 out of 10 on an attractiveness scale, which was where Todd liked to play: eights were hot, but insecure about not being tens, so they worked hard to please. Right now, though, she was barely scraping by as a six with her smudged eyeliner and greasy blonde hair.

'Then what's so wrong with taking me to dinner?' she said softly, still for the first time since she'd left the bed.

'Because that's not what you are to me,' he answered honestly.

'Then what am I?' Her voice was even softer. Her fingers clenched the sheets as she waited for the answer she didn't want to hear.

'Listen: we’ve had a really good time. Why ruin it?' Todd said, meaning it.

Her jaw set and her watery eyes shimmered. 'You mean I'm the girl you fuck.'

Todd didn't respond. He needed to get to work.

'Do you know I went to Penn? Like, I'm not some bimbo idiot. I work at a top-tier law firm. I'm the girl you date, not the girl you fuck.'

'I'm sure you’re right.'

'So let's go to dinner!' she said, exasperated.

'I don't want a girlfriend.'

'Then why did you - '

'You.' Todd cut her off, his patience exhausted. 'You contacted me, drunk, at a bar at two a.m. after you put your profile on a location-based dating app. What did you expect?'

She didn't break her gaze. 'Hook is a tool for meeting people. You're on it, and you're presumably normal. Why does my being on it make me a slut?'

'I didn’t say you're a slut. I said you sought me out in the context of a late-night booty call, and that's the implicit arrangement we’ve got.'

'But that was four times ago,' the girl protested.

Todd didn't want to hurt her, but he also really didn't have time for this kind of drama. All of his focus needed to be on his career. Having just celebrated his thirty-second birthday, Todd was all too aware that he had twelve months to make a serious deal happen at L.Cecil's investment bank if he still wanted to reach his goal of being the youngest ever managing director in the prestigious Wall Street firm.

'We've gotten to know each other since then.' She kept talking, refusing to let it go. 'We talked about your job and I told you about my family and I was late to work last week because I know you like morning sex.' Her lip was trembling.

'I didn't ask you to do that.'

Her cheeks went red, knowing it was true. 'I can't believe this is happening.' She turned and finished dressing, abandoning the search for her thong.

Todd continued watching the television, where it was agreed that, while not illegal, the fact that L.Cecil traders knew that what they were selling was crap made it unethical and worthy of fines. It was a bullshit argument— the role of a trader was to facilitate trades; it was up to the investor to determine whether or not the trade was worth putting his money behind.

Todd waited for the front door to slam and got out of bed, expensive minimalism of his spacious one-bedroom guaranteed that any girl he brought back would have sex with him, even if she'd been committed to prudishness up to that point; on the other hand, away games had the advantage that he could leave on his own terms. He should have gone to her place last night, given he knew she'd f*** him, but he'd had one too many tequila sodas at Monkey Bar and wasn't thinking clearly when he'd written her a message on Hook.

Todd shaved and put on his standard uniform - bespoke suit, Hermes tie, Armani socks, Gucci loafers. He used the Uber app on his phone to order a car and glanced approvingly in the mirror before heading downstairs.

When he exited the front door of his apartment building the girl was standing by the door, blowing into her hands to ward off the March breeze. 'Jesus Christ,' he whispered under his breath.

She saw him and bit her lip apologetically.

'I'm sorry,' she said. 'I really didn't mean to be dramatic, it's just I think this could be more. I mean, I could be more - I am more - than that girl in the Hook profile.'

He put his hand gently on her hip and kissed her cheek gently. 'It's okay,' he said, 'but I've got a lot going on, and what we've got now is the most I can do. If you want more, I respect that, but I can't give it to you.'

She nodded and looked at the ground.

'Will I see you again?' she asked softly, without looking up.

'I'm not going anywhere,' he said, dodging the question. 'Can I help you find a cab?'

She shook her head. 'No, I'll walk.'

'Okay. Have a good day, all right?' he coaxed, making his blue eyes smile.

'Okay.' She headed down the street, her four-inch stilettos and tangled hair a scarlet letter on the Wednesday morning sidewalk. Todd climbed into the black car and navigated to his list of 'Favourites' on Hook. What was her name again? A‑something. Amy? Allison? Amanda. Right. He found her, and promptly deleted her profile.

Block user? the app asked. He tapped Yes.

Leave a review? No. She wasn’t worth any more of his time.

The BlackBerry he used for work buzzed in his pocket and he exchanged it with his iPhone, scrolling through the twenty-six new e‑mails he’d received overnight. There were the normal morning blasts: the Asian market update, the FX daily forecast, an e‑mail from Catherine Wiley, the president of the investment bank, providing a compliance-approved stock statement to feed to clients who asked about the L.Cecil trading scandal.

And then: an e‑mail from

Todd—Have decided to go public. Want you to do it. JH

Todd almost choked; he read it again. He looked up at the driver, as if the man might understand the significance of what Todd was holding in his hand. Todd could feel his heart racing: Josh Hart was CEO of Hook, the app that had not only made his sex life considerably more efficient, but which was also the hottest company in Silicon Valley. An IPO on that app wouldn't just make a lot of people a lot of money, bringing it into L.Cecil would solidify Todd’s promotion. F*** managing director - a deal this big might propel him to group head status.

Todd scrolled to the e‑mail signature and dialled Josh's number.

The phone rang and he glanced at his watch, realizing it was only six fifteen in San Francisco, but Josh Hart picked up on the third ring. 'Hello?'

'Josh!' Todd exclaimed a bit too enthusiastically. 'Josh, it's Todd. Todd Kent. I just got your e‑mail and - I'm sorry, is this a good time?'

'It's fine.” Josh's voice was like a robot's.

“Listen, I’m ...” Todd struggled to find his composure

He raced to remember the last time he’d actually talked to Josh Hart: it was two years ago in Las Vegas, at the Consumer Electronics Show, when they’d met at a strip club. Josh was a pasty-white computer dork with dark circles under his eyes and boyish curls that clung to his head. He’d been wearing a hoodie and pleated khakis. Todd had spotted him across the room and beelined for him - for a guy to get into the club looking like that, he had to be important - and invited him to his table. Josh had sat studying the dancers as if they were aliens, twitching every time Todd tried to talk to him about his financing strategy, as he angled to get L.Cecil involved.

At the end of the night, Todd had given Josh his card and never heard from him again. But he must have said something right, Todd assured himself, for Josh to contact him, two years later, with the biggest deal of either of their lives.

“I just wanted to see what you were thinking, in regards to us working together on financing Hook,” Todd finally said.

“I told you in my e‑mail.” Josh sounded irritated, as if his one-liner were more than sufficient to set an IPO in motion. “I’ve decided to take Hook public and I’ve decided you should underwrite it. I’d like to raise 1.8 billion dollars at a 14-billion-dollar valuation.”

Todd blinked. Hook still hadn’t turned a profit, and Wall Street was starting to question the value of social media apps. Then again, Wall Street had doubted Facebook and its share price was soaring. Now that he thought about it, if Facebook was worth one hundred fifty billion, Hook was probably worth more than fourteen billion.

“Those numbers seem right. So the typical process is to do a bake- off, where different banks pitch you and - ”

“I don’t want a bake-off. I want you to do it.”

Todd’s brain whirred: there was always a bake-off. Was skipping it even allowed? “That’s great, I mean, that saves us a lot of time,” he said.

“So I’ll talk to my boss, Larry, he’s the one who will be in charge of the - ”

“No,” Josh corrected. “I said I want you to do it. You.”

“What? Me?”

“Yes,” Josh said. “Isn’t this what you do? Oversee deals?”

“Well, yes, I’ve worked on dozens of deals, but this is really huge, Josh, and there are a lot of more senior people who - ” Todd stopped himself. Larry had been at the bank longer, but did that really mean he knew more than Todd? Larry was also forty-five and married: what did he know about a location-based dating app whose primary users were millennials? And if Josh, who was thirty, could create a company like Hook, Todd could surely lead its IPO.

“Yeah,” Todd corrected himself to the phone, “I can absolutely lead this deal for you.”

“Good,” Josh said. “We can meet here tomorrow to finalize.”

“Tomorrow?” Todd sat forward. “I still need to get the contract together and - ” He thought quickly: what else did he need? “And I’ve got to determine the right team.”


“Well, yeah, we’ll need to loop in a couple analysts and an associate from my group, plus someone from Equity Capital Markets to advise on market conditions and the road show, and we probably - ”

“Three. You can have three more people, max.”

Todd laughed. “Josh, for a deal this size, you’re going to want - ”

“Let me be very clear about something, Todd.” Josh cut him off. “I hate Wall Street. You are all morons who do nothing but insert yourself into processes in order to profit from the inefficiency you create. If I could raise 1.8 billion dollars without you, I would, but I don’t have time in the midst of creating a company to also fix the financial services industry.”

Todd’s jaw unhinged. He knew from growing up in Northern California that tech guys didn’t like Wall Street, but it took a lot of nerve to buck a system that had been thriving for hundreds of years.

“So you can have three people on your team,” Josh continued, “but any slick dicks and the deal is off. Is that clear?”

“Yeah, sure.”

“Fine. See you on Friday, then.”

“Friday.” Todd nodded. That at least gave him a day. “We’ll see you on Friday. Really excited to - ”

He heard the phone click off and looked at it. Had that really just happened?

“We’re here,” the driver said from the front seat as Todd hung up the phone.

Todd looked up, coming back to the moment, then looked out the window and saw L.Cecil’s Park Avenue headquarters. He’d spent every weekday and most weekends of the last ten years there, save the annual two weeks’ vacation regulators forced bankers to take in a worthless effort to curb insider dealing. The glass building stretched forty-three floors into the sky, reflecting the morning light in its mirrored-glass windows. The brass letters L.Cecil hung above the revolving door entrance, set back from the street by a wall topped with flowers meant to make it look friendly, but not so friendly that people missed the fact that they weren’t invited in.

Suits flashed their security badges as they streamed into the building, all of them hoping that today would be the day a deal would come that would take them from being a cog to designing their own wheel. Today, Todd realised, was his day. Josh might be an arrogant prick, but he was going to make Todd one of the most powerful investment bankers in history. Holy s***, this was huge.

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