Jun 2, 2016 · 20 minutes

If you want a nice, easy story on gender discrimination in Silicon Valley, look elsewhere than Floodgate’s Ann Miura-Ko.

She’s had opportunities, mentors, and step-skipping that even the best connected dudes would envy. She’s had luck too: Entering venture capital in 2008, just as the institutional seed fund trend was building to fill a hole in the early stage funding market, and just as plenty of cash-strapped entrepreneurs were willing to take a risk on a new VC who’d never built a company before and never served on a board.

Even an unknown VC who was deep in her third trimester and supposed to be home on bedrest when she did her first deals.

As a result of the opportunities, mentors, and luck-- and of course her unquestionable skill-- she’s now got a track record too. Between investments in consumer companies like TaskRabbit, Lyft, Refinery29, the recently acquired Xamarin, and more sciencey names you may not have heard of like Ayasdi, her partner Mike Maples says she’s consistently made at least one investment in each of Floodgate’s funds that have the potential to return the entire fund.

Maples has been trying to persuade me-- and no doubt others-- to do an in-depth profile on Miura-Ko for some time, insisting “Ann is the one with the hot hand.” Trouble is, she doesn’t like to court attention.

I’ve asked her to speak at multiple Pando events-- including the upcoming Pandoland-- and she’s declined due to family obligations. When you corner her, she wants to talk about one of her companies more than herself. And her social media presence is more about poking fun at herself or her life as a mom-- like a video of her waking her young kids up to booming Flo Rida-- than it is trumpeting her latest industry “thought piece.”

Google her and you find surprisingly little. A transcript of a Stanford interview, a Forbes blog post calling her the most powerful woman in tech before she’d actually made a single investment, and of course, recent news that she was named to the incredibly prestigious board of Yale’s investment committee.

Still lucky breaks, timing, and an Ivy League education aside, the fact remains: Miura-Ko is a woman. Yale’s investment committee-- the envy of the private equity world-- doesn’t just throw any old VC onto its board. And women in the Valley don’t simply luck into careers like this.

Miura-Ko is more like a duck than she lets on, furiously paddling below the water to get where she is.


You could describe the breaks that got Miura-Ko into the business of venture capital and startups as a Cinderella story if that weren’t such a horrifyingly gendered term.

First off, being the daughter of a NASA Rocket Scientist and growing up in Palo Alto didn’t hurt.

Then there was the time when she was an undergrad, and she was giving a man a tour around Yale. She mentioned she was from Palo Alto, and the man asked what she was doing for spring break.

“How would you like to come visit me and see what I do for a living?”

“OK, what do you do for a living?”

“I’m the CEO of Hewlett Packard.”

That’s how Miura-Ko spent a Spring Break shadowing Lew Platt. Afterwards, he mailed her a photo of herself sitting in a chair in his office talking to him, and a photo of Bill Gates in the exact same spot.

Here’s how she broke into venture capital: A casual meeting with CRV’s Ted Dintersmith in which they mostly talked about a mutual love of opera, classical piano, and books. In the middle of the meeting he said, “Hey, I’m thinking of hiring an analyst do you want to come work for me?” She said yes on the spot even though it meant a move to the East Coast.

Later, when she was working on her PhD in math modeling of computer security at Stanford she was asked to teach a course on venture capital. The students were divided into teams and had to create viable business plans with the help of mentors like Diane Greene, Gordon Eubanks, and -- her future partner-- Mike Maples.  

Maples’ team was constantly fighting, in and out of Miura-Ko’s offices asking her to mediate their dysfunction. She’d had it. She didn’t give a fuck that she was an unknown PHD student or who Maples was, so she emailed him the following:

Your team is not doing well they are on the verge of failing, and it’s your job to get them back on track. You are not doing your job.

Maples was taken aback, but called her and admitted he’d screwed up. Fast forward to 2008 and Maples was recruiting Miura-Ko to be his partner. A role that was so coveted, it was the entire basis for Forbes calling her the “most powerful woman in tech”:

This week, Maples Investments announced that it was reforming as Floodgate, a “super angel fund” consisting of founding partners Mike Maples and Ann Miura-Ko.

Mike is well known. He’s one of the most successful angel investors in tech, having taken an early stake in Twitter, Digg, and other successful startups.

But who is Ann Miura-Ko? Partnering with Mike makes her one of the most powerful angel investors in the Valley. That makes her one of the most powerful women in tech.

Yes, Forbes really did suggest that a female venture capitalist’s power stems from the man she is standing next to. Still, inside the sexism there was a good point trying to get out: This is the world VCs operate in and Maples certainly could have picked thousands of better known men. The appointment of Miura-Ko made people sit up and take note.

The right DNA, right place, right time career of Ann Miura-Ko. If she wasn’t so damn likable, you might just hate her.

Of course, none of those stories do Miura-Ko the justice she deserves. Platt clearly didn’t offer every kid he met an opportunity to shadow him, and Dintersmith clearly saw something in the way Miura-Ko’s mind worked that he appreciated. Maples appreciated her honesty and no-nonsense bullshit detector. And all of them likely appreciated her smarts: There aren’t many female VCs-- the number has actually declined since the dot com bust-- and a smaller percentage still have math PhDs from Stanford.

There’s also the fact that she seized each of these opportunities. She didn’t do that “Lean In” thing of worrying about how a high powered career might affect her “work life balance.” She was present. She was visible. She helped create her own luck and then took advantage of it.

She advises female students at Stanford who want to work with startups to get into mixed gender study groups. A lot of startups start out all male because those are the guys sitting around the dorm room when they start, she argues. “It doesn’t just occur to them to have a woman,” she says. “They have to know you exist.”

She’s walking proof that’s good advice.

And as one of the more successful female VCs in the Valley, they were also all right to see something in her.


There’s one way Miura-Ko’s gender may have actually helped her: Maples had decided early on he wanted his partner to be a woman. As he discussed at length at Pandoland last year, Maples believes gender balance leads to better returns. There are certain skills, talents and orientations women tend to have and ones that men tend to have. Having both is an advantage. He also argues when a partnership is all male there’s a testosterone-filled room where men argue an entrenched position for the sake of being right. More balance creates an environment where he might say something one minute, but have the humility to say “Oh wait, I was just talking out of my ass…” five minutes later.

And there’s this: Floodgate sees way more deals as a result of having a female partner. (More on that in a bit.)

Miura-Ko gradually eased into being a VC, starting out as the firm’s CFO and helping Maples with due diligence before she did her own deals. The two have a similar folksy/dorky/don’t-give-a-shit sense of humor.

When he handed her all his passwords and access to all of the firm’s accounts, he said only this, “If you run off with all the money, I’m going to find you with Russian mobsters and not your ordinary Russian mobsters. The mean ones.”

Not one to let a joke drop, Miura-Ko explained later to their auditors that this was Floodgate’s official fraud prevention technique.

“I never ran off with the money,” she says.

“Pretty good program,” says Maples.

The two also love to pull increasingly elaborate practical jokes on one another. Like the one where Miura-Ko said they were making a cameo for First Round Capital’s annual holiday video and hired a choreographer to teach the gangly Maples the “Watch me whip” dance. He practiced in the firm’s glass encased conference room for nearly an hour (captured on video, natch) before she passed him a piece of paper with Ashton Kutcher’s face on it.

Silly, yes. But to Maples’ point, it’s an ease that you can’t imagine in an all-male office.

Maples has worked to help make Miura-Ko a star. “If you are going to be successful as a VC, I think the secret is to have a fast start in your first five years,” Maples says. “You have to be associated with awesome companies immediately.”

Maples absolutely fetishizes the staying power of supremely dominant venture firms like Benchmark and Sequoia, noting they work to get a new partner on the Midas list as soon as they can rather than creating dynamics of one super partner. “If we’re trying to build a firm here, we have to increase the likelihood of partners getting lucky in the first five years,” he says.


That said, Miura-Ko had to fight for her first deal under less than ideal circumstances. She swiped a check out of his desk without permission to fund another one.

The first one was ModCloth. She was still finishing her PHD, allowing some students to shadow her while she heard pitches, and sneaking out of her house eight months pregnant with her second child, where she’d been ordered to be on bedrest.

“Are you supposed to be here?” Maples would ask.

“Not really,” she’d say, still working.

On this particular day, she had three fashion related pitches in a row. They were not going well. The second one was an iPhone lookbook for high fashion magazines. Miura-Ko remembers them as “two Indian engineering guys from Stanford”-- not exactly consumers of high fashion lookbooks.

“So your customer would be a high fashion magazine,” she said. “Name a few.’”

“Vogue,” they said.

“Name another,” she said. They couldn’t.

“You could see the terror in their eyes because they had no idea what they were talking about,” she says.

The next in the pitch room were Eric and Susan Koger of ModCloth. “They came in and they are from Pittsburgh, and Susan is telling this story about doing vintage clothing shopping since she was 13. How she used to do it with her Grandmother, and eventually was buying all this stuff she didn’t even fit into, until Eric helped her put up this online store,” Miura-Ko recalls. “She told this very organic story of the development of the business and why they were doing it. That was the hook for me.”

She went to Maples and told him she had her first deal: A husband and wife team from Pittsburgh doing a fashion ecommerce company.

“You are hormonal,” he said. “Go home. You don’t have to do a deal right now.”

She forced him to take the meeting. And fifteen minutes into their pitch he interrupted them and said, “I don’t mean to be rude, but I think we’ve decided we want to do this. Can Ann and I go next door and figure out what offer we want to make?”

Maples’ “hormonal” line may offend some people, but Miura-Ko doesn’t pretend this wasn’t an emotional time in her life or that these early deals weren’t emotional. “I needed someone to take a bet on me too,” she says. “If I was starting in this economy with dollars going everywhere? It would have been a lot harder for me. Back then entrepreneurs were pretty desperate.”

Floodgate invests “too early, way too early, or ambiguously legal too early.” Sometimes that means the Postmaster General just shuts a company down, as was the case with an investment that sought to ban junk mail. But time and time again, we’ve interviewed entrepreneurs at PandoMonthlys or in Pando videos who’ve talked up Miura-Ko getting what they were doing before nearly anyone else: TaskRabbit’s Leah Busque, Lyft’s Zohn Zimmer, and the Refinery29’s co-CEOs too.

It’d be easy to stop at those examples and see Miura-Ko as a typical female VC who does deals aimed at women. But this is the twist in her track record. She also does enterprise deals. She does so called “science projects”-- a derisive industry term for cool science that may never be commercialized. One company, Inscopix, has made a microscope for the brain. “It’s a whole new way of visualizing brain surgery,” she says.

If her first three consumer deals were emotional, her first emotional science deal was Ayasdi. The chair of Stanford’s math department asked her to read a math paper that was pretty much the entire foundation of the “company” back then. There was no money, no business plan. Just a new kind of math outlined for crunching companies’ data into “high give a shit” insights.

She was still finishing her thesis and reading a lot of math papers. She remember thinking to herself “If this becomes a company, it is meant for me to fund because no one else is going to read this.”

She hunted down the co-founder and CEO Gurjeet Singh. She literally stood outside one of his Stanford classes waiting on him with a check in her hand. It was made out to Ayasdi for $1 million, and she’d signed it. “I don’t even think I had check signing privileges at the time,” she says. “I just grabbed one from Mike’s desk.”

She said to him: “Gurjeet, I would die if you took money from anyone else.”

It took her nine months to convince him he was a CEO and Ayasdi was a startup that needed her cash. (More than $100 million in subsequent venture capital would later agree.)

Success in companies like these may not make Miura-Ko a household name, but they may do more to help the image of female VCs as more than just investors in ecommerce.


Ecommerce may be the blessing and the curse of women in startups and venture capital. Women have genuinely unique insights in ecommerce that men don’t, and that’s lead to companies like Birchbox, NastyGal, Stella and Dot, RentTheRunway, and venture careers of women like Aileen Lee and Kirsten Green. The so-called “I have to ask my wife” deals.

But it’s also lead to an ugly stereotype of the types of deals “women do.” The biggest problem is what a devastating category ecommerce is. If that’s the sandbox where women are “allowed” to play, we aren’t going to see a “female Mark Zuckerberg,” Maples argues.

“We need more people like Diane Green,” he says. “We need a female entrepreneur to have a $50 billion exit, and that isn’t going to happen in ecommerce. It’s going to happen with something really technical. It’s a shame Diane sold that early because it would have been worth tens of billions and that would have been really huge.”

If that female founder comes along the odds are good that Floodgate will see the deal. Maples says about 20% of their pitches come from female founders-- a stat that larger venture capital firms simply, flat out don’t believe. Many of them tell him they see 1% or 2%. The myth of the “pipeline problem” in funding women.

Miura-Ko adds that she was recently talking to a very large firm with ten partners and over $1 billion in management about the number of pitches from female entrepreneurs they see in one week. She was stunned that she was seeing the same number as one partner at Floodgate.

Their best guess to explain the discrepancy is as a gender mixed firm that’s backed a healthy percentage of women, they tend to see all of them and that the pitches fragment when it comes to other firms. Women talk to other women about negative pitch experiences they’ve had, as we’ve detailed before.

It’s frustrating that there aren’t more female VCs, but it also makes Miura-Ko disappointed in the entrepreneurs that they don’t more aggressively pitch all-male partnerships. “If you are going to play this game, you also have to win against the guys,” she says. “I do think there’s gender bias if you are talking about selling dresses to an all male partnership, they aren’t going to get the problem. But I’m pissed that the top of the funnel is so bad. If other firms saw the number of deals we do, and we still had the same numbers, then we could argue it’s all a gender bias problem.”

As she advises her students: They have to know you exist.

And so we came to the point in the interview, after hours of hearing about the almost never-reported career of one of the more successful female venture capitalists, where I ask the question many would have started with: Have you experienced sexism in your career?

She thinks about it. Miura-Ko is well aware she’s gotten plenty of breaks most women haven’t. She’s well aware she’s had male mentors who saw something in her that she wasn’t totally sure of herself. She’s well aware that a lot what got her here was simply saying yes. And she’s also well aware her experience is utterly atypical.

But, yes, sexism is always there. The landlord who barks, “I want to do this deal with Maples!” The condescending VC who said during a contentious negotiation, “Look, you are a woman VC and she’s a female CEO. You guys should really come out of this supporting one another.”

That’s one of a thousand well-meaning sexist comments that even the most successful women hear everyday. “He would never say to Mike, ‘You’re a VC out of Texas and that guys is an entrepreneur from the South’... He would never say that,” she says.

She thinks for a while about the question of sexism and then offers this.

“So when I was at CRV I had this experience that stayed with me for a while,” she says. “An electrical engineering undergrad walked into a meeting and sitting next to me was a guy my age who was also an analyst and he was an international relations major. And this entrepreneur walks in and sits down in front of us and asks me for my background, and he never asks the guy next to me. I think it influenced me in actually finishing my PhD.”

Maples, and other male mentors, had told her she should quit midstream to be a VC full time. But another female mentor told her this: “You have to finish that PhD. I don’t care if you use it, you’ll use it.”


I had to ask Miura-Ko about how becoming a mother as she got her degrees and started her career as a venture capitalist impacted her. She had her first baby during her PhD, the second one four months after starting at Floodgate, and the third a few years later. The second was unquestionably the hardest.

“Defending my thesis, launching this fund, trying to get my first investments, when I had this huge belly,” she says. “I was stacking the odds against myself.”

She says at first she probably wouldn’t do it that way again if she could go back. But then reverses herself and says what I’ve heard from so many women in the Valley: That the extreme level of chaos and multitasking made her so much stronger.

Maples adds this is one reason he wants more women in his firm. One of his old saws about the venture business is the difference between “whiners and warriors.” People who complain when they run up against a brutal obstacle, and those who just get it done.

He likes to tell the story of when he was at a company and had one hour left in the quarter. They needed to find another $1 million in sales or they weren’t going to be able to go public. He called a CIO who had the budget and loved whiskey. “If you call me back in the next ten minutes, I’ll give you a bottle of Macallan single malt scotch,” he said. He closed the deal in time.

“Some people just get real clear on what needs to happen in those situations,” he says. “Who has $1 million and how do I get him to call me back? A lot of the women I’ve seen just act that way all the time. They don’t have time to think about it, they just know what they have to do right now. They don’t have time to think about whether they have it all. They are the equivalent to what James Bond is on the male side. How he can call up his talent at will. Women who can juggle families and careers have that same quality.”

Making his point, Miura-Ko puts the same thing in simpler terms: “I was out with my kids recently and one of them got sick. I literally had to catch his vomit in my hand. That’s how we have to roll.”