The Underwriting

The Underwriting

by Michelle Miller


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“A digital-age Edith Wharton . . . hilarious, exhilarating, and so, so clever.” —Kevin Kwan, author of Crazy Rich Asians
A suspenseful, racy, and achingly honest story of the entangled lives of six young women and men as they take Silicon Valley’s hottest dating app public.
Tara Taylor runs six miles every morning, never eats after nine p.m., is the first to arrive and last to leave the office, but is starting to wonder why she bothers. When her old Stanford flame, Todd Kent, asks her to join his four-person team handling Hook’s IPO, the deal of the decade, she sees her opportunity to break through the glass ceiling and justify six boyfriendless years of sacrifices for her career. And the $14 billion dating app might have more in store for her than a bigger bonus. But that kind of money changes people. When the deal is thrown into a tailspin, Tara and five others will each find out just what they’re willing to give up—love, family, integrity—to get to the top.

Product Details

ISBN-13: 9780399174858
Publisher: Penguin Publishing Group
Publication date: 05/26/2015
Pages: 384
Sales rank: 758,144
Product dimensions: 6.00(w) x 8.90(h) x 1.70(d)
Age Range: 18 Years

About the Author

Michelle Miller worked at J.P. Morgan Private Bank and as a consultant in Palo Alto, New York, and Europe before leaving to pen The Underwriting. Her writing has appeared in the Huffington Post, MediumTown & Country, and Redbook. She holds a BA and an MBA from Stanford University, and currently splits her time between New York and her hometown of Asheville, North Carolina.

Read an Excerpt

Wednesday, March 5; New York, New York

“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  awk‑ wardness.

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 unwit‑
ting 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 say anything. 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 some  stupid hookup.”

“Maybe 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 invest‑ ment 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 hap‑ pening.” 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, stepping his six‑foot‑three‑inch, former‑Division‑One‑water‑polo‑player frame under the waterfall showerhead.

The question of whether to bring a girl back to his place or go to her apartment was a perpetual conundrum  for Todd. On the one hand, the expensive minimalism  of his spacious one‑bedroom guaranteed 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 fuck 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, Hermès 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 softly. “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 “Favorites” 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 Cathe‑ rine 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. Fuck managing director—a deal this big might propel him to group head status.

Todd scrolled to the e‑mail signature and dialed 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, looking for a way for L.Cecil to get 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 was 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, they’d 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. Just because Larry had been at the bank longer, did that mean he really 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 to curb insider dealing.

The glass building   stretched  forty‑three  f loors  into the  sky, ref lecting 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  f lowers meant to make it look friendly, but not so friendly that people missed the fact that they weren’t invited in.

Suits f lashed 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 realized, 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 Shit this was huge.

What People are Saying About This

Babe Walker

Reading this book was better than snorting a key bump of Adderall. I hated how much I loved it.
—Babe Walker, New York Times bestselling author of White Girl Problems

From the Publisher

“Michelle Miller's debut novel reads like a salacious, ripped-from-the headlines tell-all of Manhattan's young, wealthy, and uber-successful.  From the very first page, I felt like I'd met these characters in real life: Todd, the hot, rich, d-bag banker; Tara, the striver perfectionist who can't quite please everyone; Kelly, the good girl with a secret, and Josh, the creepy savant genius who just might change the world.  What do they all have in common?  A certain location-based hookup app that alters each of their lives in shocking ways.  Get ready to settle in-you won't be able to put down this book.”
LAUREN WEISBERGER, New York Times bestselling author of The Devil Wears Prada

“Reading this book was better than snorting a key bump of Adderall. I hated how much I loved it.” 
—BABE WALKERNew York Times bestselling author of White Girl Problems
The Underwriting offers a tantalizing glimpse into the boardrooms and bedrooms of the young financiers and entrepreneurs behind a Silicon Valley IPO.  Both a corporate thriller and an exposé of two generation-defining worlds, I found it both sexy and smart.  I was hooked from start to finish.”
CRISTINA ALGER, author of The Darlings
"The Underwriting rolls out an irresistible tale about those narcissistic characters you read about who ride the waves between Wall Street and Silicon Valley and inflict us all with their dreams of riches and fame.”
BRUCE PORTER, New York Times bestselling author of Blow 
  "The Underwriting is the best one night stand I've ever had. Witty, sexy and sharp—I'd definitely call the next day. An authentically-hip novel with razor sharp characters which make it (in banking terms) a STRONG BUY."
TURNEY DUFFNew York Times bestselling author of The Buy Side 


Kevin Kwan

Reading this book was such a thrill, I was as sleep deprived as Michelle Miller's Adderall-fueled characters but having way more fun. Like a digital age Edith Wharton, Miller brilliantly chronicles the clash of cultures between high finance and high tech with perfect intricacy and nuance. Hilarious, exhilarating, and so, so clever, I'd rate The Underwriting a STRONG BUY! --Kevin Kwan, bestselling author of Crazy Rich Asians

Reading Group Guide

   1. How are the worlds of San Francisco and New York City similar in the novel, and how are they different? Do you agree with the author’s portrayal of each? Do these cities shape the narrators that live in each city?
   2. While many women in the novel hold vital positions at L.Cecil and other companies, they seem to come up against a very different set of expectations than the male characters. How is the world of finance different for women than for men? What about the world of tech? Do the women in The Underwriting confront or conform to these different standards? Do the characters’ experiences reflect your own?
   3. Has reading The Underwriting changed your views on privilege, its benefits and potential drawbacks? As a reader, do you respond differently to each of the six narrators because of their different levels of privilege? Why or why not?
   4. How did you feel about the portrayal of the finance and tech industries in the novel? Does it seem accurate? In what ways have these two industries shaped the millennials that Miller depicts?
   5. When Rachel and Tara get drinks in San Francisco, Rachel claims “there’s a difference between unemotional sex that’s respectful and transactional sex that’s orchestrated by an app. . . . Which is a nuance Josh doesn’t understand” (p. 184). Rachel argues that Josh created Hook to make women feel cheap. Do you think the women in the novel experience Hook differently than the men? How do Hook and online dating shape the way the characters interact? Has technology changed the nature of dating?
   6. Have you faced challenges similar to those that Tara faces in The Underwriting? Do you think that Tara made the right choices? Why or why not?
   7. Miller’s characters at first seem like stereotypes—Todd the playboy, Nick the wannabe, Tara the alpha female, Juan the do-gooder, Amanda the ditz, and Charlie the activist—but ultimately each is more than a stereotype. How does your understanding of these characters change throughout the novel? Do you think these stereotypes are challenged as the story progresses? Do you feel differently about each character at the end?
   8. Michelle Miller has been called a “digital age Edith Wharton” and lists Wharton, who was lauded in the early twentieth century for her incisive novels about the privileged classes of New York, among her influences. In what ways does The Underwriting comment on New York society?
   9. At the end of the novel Charlie thinks that Tara “looks different than when he’d seen her on the news” (p. 341). Why and how has Tara changed? How did you respond to her relationship with Todd, and then her relationship with Callum? Do you think Tara will live her life differently moving forward?

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The Underwriting 4.8 out of 5 based on 0 ratings. 5 reviews.
Anonymous More than 1 year ago
Clever plot, distinct characters, great fun yet offers wickedly astute cultural observations.
Anonymous More than 1 year ago
Enjoyed reading this novel! Very fresh, modern, & relatable. Can definitely see this becoming a motion picture.
Anonymous More than 1 year ago
I'm a sucker for jackie collins. Although this is milder it is a good read to the introduction to books about money sex and power.
Anonymous More than 1 year ago
BrainyBookBabe More than 1 year ago
Could NOT put the book down for the life of me. Sort of a Devil Wears Prada in the tech industry. This book was awesome. The worst part was getting to the end and finding out that we have to wait until the spring for the sequel to find out what happens to everyone! Plan on staying up all night with this one!!!