The Other Woman: Business and Friendship at a Silicon Valley Startup -The Toast

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I used to have a hard time understanding the intimate friendships between other women. They talked multiple times each day, texted encouragements like, “You got this!” and shared emotions more intimate than romance. I couldn’t help feeling both envious and smug. An engineer and Silicon Valley entrepreneur, I had adapted by deriding the girlish sentimentality I couldn’t seem to understand. My friend Amy, in constant contact with her best friend Alyssa, tried to explain it to me once. “Things don’t seem real until I tell her, she said.” Pshaw, I thought. I had never had such a friend. Not until I became business partners with Philippa.

We met in 2006 through our investors, Dan and Samir, who found us through our husbands on LinkedIn. Three years later, Philippa and I left them in a conference room and collapsed into two cubicles in their shabby San Mateo office. Dan and Samir had given us an ultimatum. We needed to pivot again, start a new company—a third—to try to make back what we had spent. Dan said our current business, like the one before it, was “nifty for two mompreneurs who are not co-located,” but would never be profitable enough for impressive return.

“I’m not a fucking mompreneur,” I said to Philippa. “He might as well have slapped us each on the ass.”

Seriously,” Philippa laughed. Intricate irony, chipper but slightly tart, played around the edges of her beautiful British accent. Her voice made me feel adventurous and worldly. Philippa reclined in the plastic chair beside me, her hands clasped behind her head. Her long-sleeved, fitted white t-shirt was inside out. I should tell her, I thought. But I didn’t: her careless attractiveness endeared her to me. This former lead HBO attorney dressed inside-out and I was not only charmed by it, I respected the way she could look casual and think elaborately.

We were a team that had demonstrated we could get shit done, even when we were 3,000 miles apart. We had an ongoing symbiotic relationship, mostly via phone and Google chat, congratulating each other on being productive, admitting our mistakes, and making decisions. We were co-founders. I was the CMO and Philippa was the CEO.

Philippa Smith. Her father, deceased, had been a roving British diplomat. My father, retired (which seemed a lot like being dead to me back then), had been a U.S. Health Department employee who, in forty years, took only one business trip. I believed that the entire time I’d been eating hot dogs and playing Red Rover growing up, Philippa had been eagerly supplying humanitarian aid and studying Latin in an ironed blue schoolgirl uniform. Philippa had been a Barrister-at-law in London, I, a mortgage loan agent in Fremont. My life had been ordinary. Hers had been extraordinary.

And yet we were immediately compatible. More, I had never felt so much like the real me as I did when we were working together. But we weren’t BFFs; we were business partners.


Dan and Samir’s demands were fair—we had come to the same conclusion ourselves about a pivot—but we resented some of the terms involved in heeding them. To start up again, we’d need money. Some would come from Dan and Samir, a small bridge loan in exchange for more of our already depleted equity. But we’d need more. We’d have to put on fancy pants and again visit the venture capitalists on Sand Hill Road and University Avenue, and talk to more angels in Mountain View and Manhattan. Not to mention create real work. We needed to conjure up another company.

Down the short hall, we could hear our investors leave the office. Lunchtime. All our officemates—the twenty-something male entrepreneurs who’d been funded by our investors to develop gaming appswere out eating pho or curry. Philippa removed the brown elastic band that rode around her wrist when it was unemployed, using it to tie up her long dark hair in a chic, messy bun. I grabbed an energy bar and began to unwrap it as I watched her and waited, because she began things, and I finished them.

Frequently, after hours of discussion, she would suggest something especially smart in a haphazard way. I would slap my desk in rapturous agreement and say, “That’s it. You nailed it.” She wouldn’t realize it, and usually she’d question its viability. I would go off and dress up the idea, make it an actionable plan and present it to her. “Brilliant,” she’d rave. “This is incredible, Sarah!”—honestly unaware that it was originally her idea. Philippa was good at running the business, pacifying our investors, identifying possibilities. I was good at telling the story, inspiring our employees, making things happen. I was confident in her ability, and she in mine. And I was in love with the fact that she liked and respected me.

“Well,” she said, “where do we start then?” Her eyebrows rose and we laughed, imagining the slog of toil, but also the whiz-bang hum of collaboration. Then she cocked her head and said, “Sarah. Can we really do this again?”

So far we’d run a video production company and a blog ad network. And now, another startup and all that came with it—the sleeplessness; the juggling of schedules between our company and our clamoring, cuddle-hungry, technology-obsessed young sons; the indignity of competing for investor face time with twenty-something boy entrepreneurs; the humiliation of asking for more money from middle-aged billionaire men; the sheer frustration of building and caring for a team, a company, a family, and lastly, ourselves. But we had known the giddy adrenaline of production, of hope, of being busy and knowing who we were and why we were there, of deeply rewarding collaboration and intimacy.

Can we really do this again?

What is a life for? And so I told her, “Yes. We can.”


Yes. We can. Sometimes I think I said it too freely. For five years it slipped out effortlessly, as nonchalantly as thank you-gotcha-will do-of course-you’re welcome. We got this! It was my ritual response to whatever Philippa wondered.

“Can we really launch a market with such a small budget?” Philippa would ask.

“Yes. We can,” I’d say.

“Can we change our minds about that new CFO hire last minute?”

“Yes. We can.”

“Jen’s not working out. Can I really manage the entire engineering team on my own?”

“I’ll help you.”

“Sarah. You’re not sleeping. My childcare situation is a shag. The guys aren’t listening to us. We can’t keep going like this.”

“Yes. We can.”

We were lucky: we had a choice. We could have said, “No. We can’t,” and walked away. Staying home with the kids was an option for both of us. But we chose to work.


We launched daily deals because Groupon was on track to do millions in revenue through billions of clicks of little green “Buy Now” buttons. We targeted moms because we had a million-mom audience already, and they were the largest deals market.

“Your button could be pink,” Samir had suggested in the conference room.

“Oh, hell no,” I’d said. We made it orange. 

Although our product was a clone, Philippa and I thought we had made our company unique. We created it in our image and tried to run it like a family. We studied Groupon’s professional in-house sales model, then built a distributed part-time sales force instead. Our motto was “Save Local,” and we went after press that lauded us for battling the big guys.

It worked. USA Today ran an article about us titled “GroupMom.” We met in places like DC and LA for summits and sales gatherings, and held weekly All Hands meetings in the biggest conference room—named “Athena”—for our multiplying numbers of predominantly female employees. For a time, new hires, like rabbit kits, seemed to crop up in the cold burrow of that conference room unbidden. And each day I knew my actions would be vital to something—our company—and to someone—Philippa. To us.

We were entrepreneurs and mothers. “Raising kids,” some mothers said, “is the toughest, most important thing.” We believed this to be true: our children’s happiness, to the extent that we could induce it, was the ultimate achievement. But motherhood was not a career. We believed we could best determine our children’s happiness by giving them a mother who wasn’t always with them or in constant conversation about them, who had a vivid life and accomplishments, and who could circle back with her own sense of self through the prosaic fog of carpools and grocery shopping to meet them for dinner, homework, and bedtime, buzzing. We believed we could best advance it by showing them our own successes, not by hovering over the potential of theirs.

Studies show working mothers spent more time with their kids in 2009 than stay-at-home moms did in 1959. Philippa played Risk and Minecraft with her sons, cooked with them and read the entire Harry Potter series. I took my boys on field trips and beach vacations and coached teams and taught Great Books. We cared for and loved them. 

Still, for five years, we spent more time talking with each other than with our husbands, our mothers, our friends, or our sons. Philippa became as close to me as a spouse. Maybe closer. We shared a business, and also beliefs. This propinquity bred my most intimate friendship. It was a heady relationship, a female platonic bond that was nonetheless romantic and true. My other friendships, my motherhood, and my marriage thrived in the wake of this fulfillment. I was my best in Philippa’s eyes, and I adored it.

But most startups fail.


I have a picture of us at the party we threw in our new offices around the time of our second anniversary. 2011. In it we are shoveling huge chunks of what looks like bright pink wedding cake into one another’s open, smiling mouths; in the background, employees and friends, and my husband and sons are blurrily baring teeth tinged pink with frosting, juice, and wine. I remember walking around that night, accepting accolades and purring with humble magnanimity. My mom missed it, waylaid by a broken hip. I reassured her: there would be more parties. Our company was climbing.

But six months after the party, the deals trend began to die. Our subscriber base shrank. We had been hiring continually, and now our burn rate became untenable. We laid off ten people and identified twenty more, a process that afforded me an experience I’d only seen in movies. I wasn’t sick the day we let them go, but I was violently ill in the hallway bathroom just before I started firing people. I knew they’d be okay—get new jobs—but would I?


Three months later, on a Friday, Philippa and I were on the phone and in our second hour of debriefing about the day and the coming week. I was in the Menlo Park Walgreens, picking up my birth control prescription and avoiding the office, where I had just laid off ten more of our employees. My chest hurt. I made my way through the feminine products aisle, and then to cosmetics, where I grabbed an unneeded pale pink nail polish because its color and frivolousness somehow cheered me. The previous month, when we laid off the first round of ten people, Philippa had been here. This time, our investors insisted that flying her out yet again was redundant. Right, I suddenly thought. It would have been ridiculous.

As I headed for the pharmacy, Philippa said: “Sarah? Can we do this again?”

I wanted to say it. Yes. We can. Instead, I flinched and shook the nail polish, wondering if she could hear the small clacking of the metal mixing balls. “Well, we…” I said, then paused. Had she detected the break in my voice?

“You know what?” She waited for a long moment to pass. “Maybe we can’t. Monday would be the ideal time to fire us.”

“Holy shit.” I looked up past the blush and foundation and into the mirrored rim of the cheap slanted ceiling where I found my reflection, wired up in my headset, alone. Instinctively, I grabbed a pair of false eyelashes. “They’re going to fire us.”

We said us but we were talking about her. We believed I was too visible and integral to remove yet, because the company was here and I was physically present in it. But in our vernacular there was only us and our. Our company. Our partnership.

It had been clear to me for a good while that we were in trouble. Many times in the past few months we had discussed stepping away, going part-time, or just quitting, both to help with the burn rate and to save face. But the time was never right to leave together, so I couldn’t do it. I could not voluntarily leave what we had built. I couldn’t leave Philippa. More to the point, I couldn’t leave who I was when I was with her.


At eleven on Monday, Philippa called. “That’s it,” she said. Her usual accent, so lovely it seemed to alter the air, was undetectable. “I’m out.” 

“What?” I was sitting in a cubicle near the operations team, which we had kept nearly intact to continue running our website and processing orders. My entire marketing group was gone. No one was close enough to hear me whisper. I stood up and speed-walked, chest leading as if across a finish line, toward Athena and shut the door.

“I just got off the phone with Dan. I was right,” she said, as if the fact that our prediction had been hers made it easier to take. Actually, I knew it did. She hadn’t preempted Dan, but at least she saw it coming. I had seen it coming, too, along with her. In many ways, this was what mattered.

“You there?” she said.

There is no more we, I thought. 

“Fuck!” I said. “I can’t believe it.” I was having trouble processing the situation, even though I’d been wise to it. “What’d he say?”

“They need new leadership to get new money, I’m not there anyway, can’t help raise, don’t really have ‘defined responsibilities’…”

“Other than doing everything related to running the business financially, legally and operationally, you mean?”

“Right. But not well.”

“Please,” I said, “don’t.”

Philippa laughed. It sounded bitter. Different. She did everything better than anyone gave her credit for—except fight back. The guys had often told her she didn’t do enough. I’d often told her she was too nice, too willing. They had walked all over her. Had she let them? Was I distancing myself already? Without her, I would be the widow. I would also be the other woman, the one they kept.

“You okay?” I asked.

Silence. And then she said, “I did think I was more prepared.”

“Me too,” I said. We did not cry or tell each other it was okay. We weren’t criers, and it wasn’t okay.

“I’m sorry,” she said. “I failed you completely.”

“Stop it.”

“I can’t.”


I went back to my office and sat, dumbstruck, staring past the computer and into the modest neighborhood out my window. In the past, almost nothing happened unless I first chatted with her about it. And now I wasn’t sure what to do with myself. I fondled the gold coin and stone around my neck, a company charm we both wore and had given to employees as well. Should I leave the office? Go home? Go to Nordstrom and buy something, like a new necklace with a skull and crossbones on it? Where was the nearest tattoo parlor?

Grandiose gestures. And hollow. What I did was stay. I walked to the deli across the street but could only stomach a banana, and then I came back to my desk. I texted my mom, my husband Noah, and my best friends to tell them the news. They responded with condolences, texts like, “No! I’m so sorry. What can I do?” and, “OMG you must be devastated.” They knew that a huge part of me was still wrapped up in Philippa, and now I was losing it.

At two, I walked into a meeting with Dan and our CFO, Joe, and said “How could you?” even though I didn’t expect an answer and didn’t get one. I announced that after the meeting I’d be working from home for a while. Joe rushed us through the meeting and presented the new product pricing. Foolishly, I agreed to it. The truth was, I didn’t care. Immediately, I felt less—almost nothing—without her. I wanted to quit.

And yet I was still there, leading our company. The big part of her that was wrapped up in me would survive as long as I stayed. So I did.


Eighty-six days later they fired me.

A cloudless day in March. I had just completed the lackluster branding for the new product launch. (In the aftermath of Philippa’s firing, I was unduly mawkish and intellectually uninspired.) At ten I sent the PowerPoint file to Dan and Samir. Ten minutes later I began refreshing my email for their feedback. It never took them long to reject things. Twenty minutes passed. Maybe they actually like it? I thought. Maybe I can save us.

Dan’s message came through at 10:33. “Hoping to swing by today and discuss the state of fundraising and future of the business with you. Are you around? Say, 1:30 PM?” In five years, Dan had never traveled across town to see me alone to discuss funding, the state of our business, or anything else. So I knew.

I group-emailed Dan’s message to my partner and my husband and said, “Well, here we go.”

Philippa didn’t respond. I knew she was working in her son’s preschool class, where she had often reported she was tortured by four-year-olds making papier-mâché eggs and demanding Dixie cups of organic apple juice. But her silence still felt like abandonment.

Noah was down the street managing his own burgeoning startup. “Shit,” he texted me within minutes. “Love you.”

At 1:20, as I trudged down the hallway, I thought, Maybe this is all a great misunderstanding. Maybe Dan wanted to prep another VC pitch with me, or let me know that VeriStreet had decided to buy our sales force, which I would then be called upon to inspire. “They can’t lose you,” Philippa had said on numerous occasions over the past three months. “You are the company.” I’d let myself partially believe her.

I sat waiting for Dan in the center of Athena, facing the door, my back to the bright afternoon sun. My iPhone was cradled in my lap: an entire support group and production center. Messages were light that day, that month. In the thirty minutes I waited, not one email came through. No one texted me.

When he came, Dan’s shadow moved along the back wall just as his body did—tall and square-shouldered, mechanical. I looked up just after he closed the door, another signal of what was coming, and offered him my attention, careful not to look worried although I was terrified.

He gathered himself in a chair across from me. “How are you?”

“Fine. Great.”

“Good. Glad to hear it. That’s good.” He leaned back, forward, then clasped his hands together between us on the table. “As you know, you’ve lost a lot of money.”

Each time I laid off an employee I had been instructed to stick to a script, keep it impersonal, and insist, “This is a reorganization and has nothing to do with job performance.” Edging down the hall a half-hour earlier, I had dreaded the same insincerity, and had prepared myself to pounce on it and call bullshit.

But Dan’s candor was a relief, refreshing even. I did feel like a failure—I knew I had failed Dan and Samir by not making a huge return on their investment; failed my employees; failed my customers. I was ashamed of that.

“So we need to make a change.” Dan’s salt-and-pepper hair didn’t move beneath the air conditioning. His face didn’t emote. “Philippa has already stepped away.”

“Um, seriously?” I coughed. “You pushed her off a ledge.” When they fired her, she was allowed to keep her health benefits, which her family of five depended on, in exchange for announcing that she was leaving voluntarily. I forced an ironic laugh to let Dan know I didn’t plan to lunge at him, and also to prevent myself from crying.

“I wouldn’t put it like that.”

The conversation was threatening to get out of hand. I needed to wrest back some control and dignity before he could continue. I needed to remember that this was about me, not Philippa. But it wasn’t easy.

“I had come to the same conclusion myself,” I said. I was just about to break up with you anyway. “It seems the business might be better off without my involvement going forward.”

Dan nodded. I wondered: was he confused by my immature attempt to dump him before he dumped me? “You might want to stay involved in some capacity as a founder.”

“No, no.” I smiled. “I don’t.” We will not be friends.

“We all wish this would have worked out differently.”

I wished his head would explode and I wanted to wail. I said, “I want my name off the website.”

“Come on, Sarah,” Dan tried. “You built something. You can’t erase that.”

“Yes. I can.”

“I see.” He shook his head. Then he leaned back and closed his laptop with a snap. “Stay for a week. Work on transferring all your knowledge to Joe.”

“Right.” They’d get nothing from me. But it wasn’t because I was petty. It was because I had nothing left to give. “Understood.”

And then he was gone. For a few moments I felt anesthetized. I wondered what I would do the following week, what I would tell people. Would I admit I was fired? Would I slip into denial and tell them I left willingly? What had Philippa done? She hadn’t told me.

I grabbed at the phone and called her. No answer. Was she still at the fucking preschool? Or was she picking up Liam from practice? Roasting a chicken? Banging her head against a wall while the kids played XBOX? I slapped both hands on the table, then snatched the phone again and threw it, watching it skitter across the table to finally rest in the place where I wished she was sitting.

I threw my back against the chair and slumped down. And then I thought: As long as I sit here I will keep the last piece of our partnership together. I crossed my arms and hunkered down. But I couldn’t sit there forever. Eventually someone would come into the conference room, or I would…what? Toss my phone into the wall? Call everyone I knew and begin crafting my story? 

I stayed for ten or fifteen minutes, doodling words like “failure” and “over” on my notebook just to look busy in front of the few remaining employees who could see me through the glass walls of the room, like a middle-schooler tracing her ex-boyfriend’s last name in maudlin cursive during an English lecture. And then I stood up, collected my things, and went home. Philippa called me as I pulled off Highway 280 onto Sand Hill Road, where we’d once pitched our lost partnership. “That’s it,” I said. “I’m out.” I told her what happened. The loss of our company was complete.


But my relationship with Philippa was redirected, not lost. How could it have been lost? We were so close. Though we don’t talk often and we haven’t seen each other since we were partners, Philippa and I will always be intimate. I can ask her for anything, depend on her for everything, and will confide in her always, the way that sisters pick up wherever they last left off. It is true that partnering with Philippa exhilarated and changed me, and that losing the partnership slayed me almost as much as recognizing my own failure. But it is also true that through our work, I have seen beyond the trivial to the ritual of symbiotic twosomes, past the sororal and girlish-seeming acquaintances to what I now know are true female friendships, life-affirming and deep. And now, how can I ever belittle or disparage the close friendships that bind the women around me?

I don’t. I admire them. I hadn’t known before that a friend could reflect and enhance a woman’s sense of self-worth so intensely. I was my best in Philippa’s eyes, and I adored it.

The other day an email arrived from Philippa, who is working at her own startup in Manhattan as I write our story in Menlo Park. I hadn’t heard from her in months. “Help!” read the subject line. There were ten images attached. “Which logo?” she asked.

“The second one!” I wrote back.

“Bingo,” she replied.

I knew what she meant. The image I chose had been her favorite, too.

“I miss you,” I typed. I didn’t hear back from her, but I didn’t need to. I knew.

Sarah Eisner is a Silicon Valley native, mom of two, and recovering entrepreneur turned essayist. Her essays have been published in The Rumpus, Salon, and Stanford Magazine.

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