Learning to Play the Game

“You’re live now, so it’s a ticking time bomb,” Penny Herscher, the executive chairwoman of FirstRain, a business software company, told Ms. Miller in July. “Can you get enough momentum to get liftoff fast enough?”

Ms. Herscher, who has two and a half decades of experience as a software executive, was introduced to Ms. Miller through a colleague and had agreed to become a kind of mentor. Ms. Miller had unveiled Doxa three weeks before. The site had 820 active users, and 300 companies on a waiting list to be included.

Now it needed money. Ms. Miller had calculated that $2 million in venture capital would enable her to hire the people she needed and keep the company running for 18 months. But time was tight. She needed to start paying salaries.

She had made her pitch to three small, mission-driven funds that wanted to invest in female and minority founders. Ms. Herscher said she should be aiming instead at well-known venture capital firms.

“The thing is, no real investor is going to invest in you because of the mission,” she said. “They’re going to invest in you if they think you’ll make a lot of money.”

“The feedback we’re getting from the big guns is we’re too small now,” Ms. Miller told her.

“They didn’t wait for Google to have a prototype before they invested,” Ms. Herscher said.

The first time they met to discuss Doxa, Ms. Miller had worn jeans and a sleeveless shirt. The look was too unprofessional, Ms. Herscher told her. She should dress like Yahoo’s chief executive, Marissa Mayer (whose uniform is crew neck, knee-length dresses with cardigans). Ms. Miller said that everyone she had worked with at tech companies wore jeans and T-shirts, and surely no venture capitalist cared if Mark Zuckerberg showed up in a hoodie. Ms. Herscher was uncompromising: Like it or not, the standard is different for women.

This time, Ms. Miller wore a dark cardigan over a dark blouse.

Ms. Herscher asked if she had been hit on yet by venture capitalists. She hadn’t. Ms. Herscher told her own horror stories — the investor who slipped his hand under her hair and massaged her neck, the one that rubbed her knee.

Ms. Miller was more worried about the investors’ reaction to her pregnancy. She broke the news to Ms. Herscher.

After congratulations, they plotted strategy. Wait until the second meeting to mention it, Ms. Herscher said. “Then say: ‘I’m pregnant. And I’m so well organized that my baby’s due on Christmas Day, which will be a slow time. I don’t expect it will faze me at all. I’m married to a man who will be a primary caregiver, and this is no different from investing in a man whose wife is pregnant.’”

Then her tone shifted. She wasn’t talking about business anymore.

“Having your first child is just physically hard, emotionally hard,” said Ms. Herscher, who has two children. “I would never discourage you or say you can’t do it, because you absolutely can. Just be very clear why you’re doing it and what price you’re willing to pay, because the price is time with your baby.”

After the conversation, Ms. Miller talked with her husband, who works in advertising and was then a freelancer, about being the primary parent. He was on board. She figured she would take off a few weeks and get right back to work.

The gender issues and sexism that Ms. Miller’s generation faces tend to be different from those of earlier generations. There is still blatant bad behavior, but official reports of sexual harassment have declined in recent years. More often, the challenges are subtler.

At the gender discrimination trial last year against Kleiner Perkins Caufield & Byers, which the venture capital firm won, female employees said they were excluded from a ski trip, denied credit for deals they brought to the firm, and told they both didn’t speak up enough and talked too much.

“I feel like it’s a lot more nuanced and sometimes it’s subconscious,” said Julia Hu, the founder and chief executive of Lark, which makes a health and weight-loss app. “V.C.s are pattern matchers, and they’re just used to seeing men like themselves.”

Many women convey confidence and leadership in a different way than men do, she said. As an Asian woman, she said, she was raised to be humble and quiet and felt uncomfortable promoting her skills. “To try to be who I thought they wanted me to be, which was another Mark Zuckerberg, was actually very difficult for me without feeling inauthentic.”

Later, she realized that describing business partnerships she had made, like one to preinstall Lark on new Samsung phones, was a more effective way for her to demonstrate her leadership skills than boasting about herself.

Social science research supports Ms. Hu’s experience. A series of experiments by Laurie A. Rudman, a psychology professor at Rutgers, found that women who spoke directly about their strengths and achievements were considered more capable, but also less hirable. Self-promotion by men made them more hirable.

In parenthood, too, there is a double standard. Mothers are penalized in pay and promotions because employers assume they will be less committed to work, research shows, while fathers get raises because employers think they will be extra committed to breadwinning.

People in Silicon Valley say new motherhood is particularly difficult, because competition moves at hyperspeed. Ms. Mayer, for example, felt the need to announce that she would be “taking limited time away and working throughout” her leave after giving birth to twins late last year.

‘Speak in Bullet Points’

A few weeks later, Ms. Miller was back at Ms. Herscher’s office, practicing her pitch while Ms. Herscher played the part of skeptical venture capitalist.

Ms. Miller had been working 70 hours a week managing Doxa, recruiting companies, trying to raise money and working nights with the engineers who had day jobs.

Several firms, including 79 Studios, an investment fund focused on female entrepreneurs, had told her they would be interested in investing if another firm led the financing round. “We’re pretty positive on this from a mission point of view and even from a return on investment point of view,” said Saujin Yi, chief executive of 79 Studios — but the firm typically invested only alongside a lead investor.

Though her pregnancy had been relatively easy — at one point she vomited on the sidewalk after meeting an investor, and she was down to a single professional-looking dress that was loose enough to hide her growing belly — she had not told any investors that she was pregnant, though two had obliquely asked if she was planning to have children.

Ms. Miller began her practice pitch to Ms. Herscher: “Doxa is a platform to match qualified people to the right companies. Once this platform exists, we’re going to wonder how we ever found jobs before.” She talked about the team and showed a diagram of how the service worked.

“At this point I have no idea if this is important,” Ms. Herscher said. “You’ve told me there’s a problem but not if it could make money.”

They ran through some more slides, including her go-to-market strategy — aiming at women in tech.

“I’m immediately turned off and lost, because what you’re telling us is you have this fantastic technology and star team, and you’re going to go after this itty-bitty market and a bleeding heart cause,” Ms. Herscher said.

Ms. Miller finished her pitch. It needed to be crisper and more confident, Ms. Herscher said: “It’s an art to speak in bullet points. It takes practice. Sit in the car and say it over and over.”

“O.K., wear cardigans, speak in bullet points,” Ms. Miller said.

A week later, she met with Ms. Yuan at Cowboy Ventures. Her tone was more confident and her pitch faster, and she had broadened it beyond women in tech. “The tools can be used by anyone — the recruiting market is gigantic,” she said. “What people want is not gender-specific, it’s very millennial-specific.”

Ms. Yuan pushed back. “There’s this inherent tension in the way we monetize,” she said. Doxa was asking companies to pay to use the service for recruiting while at the same time the site would publish potentially negative employee comments about the companies’ culture.

“It enables companies to be responsive: ‘Let’s get a maternity policy because we don’t want to be up on your platform without that,’” Ms. Miller said. Smiling, she added, “I love that you’re saying ‘we.’”

Her next pitch was to NEA, a global venture firm. She wore a gray, knee-length dress, cardigan and short heels. She thought the conversation flowed easily.

But a few days later, both venture capitalists declined to invest. NEA said Doxa didn’t show enough traction with users yet. Cowboy said it wasn’t clear that Doxa’s technology was different enough from that of other hiring websites.

“I really thought it was a good idea,” Ms. Yuan said later. “But there were really well funded start-ups in this space, and it was hard to tell because it was so early.”

Ms. Miller told Mr. Meder that she was scaling back her ambitions from raising $2 million and hiring a full team to raising $500,000 for just the two of them. But things had changed for him. He had been given more responsibility at his day job, and it didn’t feel fair to leave for Doxa, with its uncertain prospects.

Ms. Miller canceled her coming pitches and told potential investors that Doxa was on pause. She had talked to more than 40 venture capitalists. But without her co-founder, who was building the technology while Ms. Miller built the business, venture capitalists were unlikely to provide financing.

The flip side of overnight success in Silicon Valley is overnight failure. Start-ups can be so dependent on a single investor or partnership that a turn of events can change their fates.

In 2011, Jason Shen helped found a start-up called Ridejoy, for connecting people who were driving long distances. For a time, it seemed as if it had the golden touch — entry into Y Combinator, $1.3 million in venture capital and traffic pouring in from Craigslist, where it posted its services. Vanity Fair did a photo shoot with the founders, and a writer profiled them for a book.

Then, Craigslist sent a cease-and-desist letter, forbidding Ridejoy to post on the site. By the time Vanity Fair came out, Ridejoy had laid off nearly all its employees and stopped working on the site.

“Now I see companies who raised $10 million, and I’m like, did we just not have guts? Did we just not follow through? Did we just not believe in our thing enough?” said Mr. Shen, who now works at Etsy. “Funding is such a confidence game.”

He is saving his money to try to play the game again.

As her baby’s Christmas due date neared and she approached a year of living off savings, Ms. Miller began to get an unfamiliar feeling: the desire for stability.

She was searching for a new technical co-founder. A few of the investors and companies she had met during the fund-raising process had contacted her about working for them. She began consulting at Code 2040, a nonprofit that matches black and Latino software engineers with internships at tech companies, started by Mr. Walker and Laura Weidman Powers, whom Ms. Miller knew from college.

A couple of months later, Code 2040 offered Ms. Miller a full-time job, as the director of partner programs. She accepted. Building a new business focused on diversity fulfilled some of the hopes she’d had for Doxa. She imagined keeping Doxa alive as a side project, once she had more time.

Ms. Miller’s plan was to take a month off and get back to work. Then, right on time, on Christmas Day, she gave birth to a girl, Zadie Mai, and changed her mind. The baby took over her thoughts. “I feel a mixture of intense love and protectiveness,” she said. “I want to hang out with the baby forever. There are my real physical needs and the physical dependence of the baby, all this stuff I didn’t expect to be so consuming.”

She said she had an entirely new perspective on how undervalued caregivers are, and how people judge women for taking time off work for their families.

She decided to take at least six months off, doing some work from home after three or four months, and Code 2040 agreed. Her husband, meanwhile, had found a full-time job in advertising.

Ms. Miller said the transition from start-up founder to employee and mother had given her a new perspective on success in Silicon Valley and, more broadly, on what her generation wanted from work, something she wanted to address in her new job.

“I wasn’t naïve,” Ms. Miller said. “I knew when I quit Instacart that going on this entrepreneurial journey wouldn’t be like ‘The Social Network.’ ”

“But for me, this was a lesson that it’s not always a straight shot from idea to financing to taking over Silicon Valley and taking over the world,” she said. “Maybe this was just a lesson that being entrepreneurial and taking risks and jumping into new things you’re excited about sometimes is not linear at all.”