Why Silicon Valley has “Open Secrets” and What We can Do About It

I don’t know Justin Caldbeck personally, though we have a number of friends in common. I was not aware of what is now being referred to as the “open secret” about him — despite being a woman who founded a company in Silicon Valley in 2012 . But, I am familiar with the dynamics that enabled his behavior, and I’m not surprised it took Niniane Wang seven years to get the story out.

Both Caldbeck and his Binary Capital former partner Jonathan Teo have now publicly acknowledged that Caldbeck acted in appropriately with women in a professional context though as a number of people have pointed out the multiple statements come off as tone deaf. It is clear from the admissions that Caldbeck crossed the line in ways that are unethical and certainly damaging on all sorts of levels to the women who were targeted. But lets not be seduced by the idea that this is a rare example or that it is the result of just one (or a few) bad actor(s).

I’m grateful for the women who chose to stand up publicly, and my heart goes out to all the others that did not share their story nor name. There are surely many such women: People typically exhibit *predatory* behaviors many times before they get caught. Since this story broke I have been contacted privately by a number of women who would like to speak out about their experiences but can’t due to NDA’s or the emotional or professional consequences of doing so.

Despite working for years in Silicon Valley, I have been fortunate to have not directly experienced actions that are as overt as those described. I have had hundreds, maybe thousands of business meetings over the years, and I have not been groped nor propositioned for sex — this doesn’t mean it doesn’t happen, perhaps it just makes it easier for me to speak up.

I have however experienced far more subtle actions and implications many, many times that contribute to making the industry more hostile toward women. So has every female founder I know. This includes being invited to a conference or networking dinner “because we need more women”…. being told by an investor that “I only invest in two young dudes in a garage”… hearing about how a friend was able to secure his funding by “going to the strip club with partners after work because that’s what they like to do”… having investors continuously direct questions to the male in the room even though I was the one pitching and had more information about the product and business… being told that I should dress a certain way to get more (or less) attention… being asked to coffee or lunch thinking it was purely business or networking and hearing from someone else later that they actually just wanted to date me… hearing from women who pitched for B and C rounds of funding without coming across a single woman on the other side of the table… knowing countless stories involving women being bullied out of what they deserve (equity, leadership, respect, etc.) because someone with more power feels entitled to do so.

I have learned to deal with this dynamic in my own way over the years. Sometimes I’d wear (fake) glasses to pitch meetings… I’d dress up or down, hair up or back, shoes high or low depending on what I thought their particular perception of women would be and how I could best counteract it to be taken seriously… I’d avoid dinner and drink meetings whenever possible although this is a common way to do business in Silicon Valley and networking is paramount… sometimes I’d wear a ring on a certain finger to imply that I was not available… I’d err on the side of avoiding response to certain introductions or requests if I though there was any chance of interest being other than professional even when this is not stated directly… and I’d try to always ensure that within 30 seconds of meeting a man professionally in any situation I’d have them engaged in a conversation that showed I was very smart and serious, and in doing so somehow signal that I was not open to any funny business.

Being an entrepreneur is tough enough. Being a woman entrepreneur in Silicon Valley is like walking a tightrope to catch a flying trapeze, blindfolded with a scalding pot of molten lava balanced on your head. You are hyper aware of the dynamics running in the background that are ready to trip you up at any time. Yes, it is a privileged position to be able to start a company in the first place, but that doesn’t in any way mean women should have to excuse the type of behaviors that occur.

Without diminishing the gravity of Caldbeck’s actions, or those of anyone else who has been called out publicly for behaving in this way, it is important to note that this problem, to varying degrees, is widespread and common in tech. I can’t even count the number of stories I’ve heard whispered to me about experiences women have in the industry. If there is any “open secret” it is that women are harassed in ways subtle and overt all the time. So much so that that it doesn’t feel like there is any path for recourse or change and we just learn to put up with it and wonder what else we can do to avoid being seen “as a woman”. These actions are wrong, unethical and in some cases almost certainly pathological, and they hurt both individuals and the ecosystem in ways that are difficult to quantify and long-lasting.

Again, Caldbeck’s harassment was referred to as an “open secret”. He is friends with some of the most connected and influential people in Silicon Valley. They had to know about his behavior. Why did the endorse it? Why did they back him with capital, connections, influence? His fund, Binary Capital, was one of the most successful ever to raise capital as a first-time fund in 2014 with a $125M raise closed in record time and a second $175M fund announced toward the end of 2016 and at least $75M more that had reportedly been expected to close this week. I applaud the investors that are speaking out now about this behavior, but I have to wonder, why just now? They have to have known this sort of thing has been going on for years.

Why? Because in the current climate power trumps all, and power in Silicon Valley means money and connections both of which Caldbeck seemed to access with ease. So a lot of people wanted access to him. Simple as that.

Why do motivations matter? Because if we really want to drive change home, we need to ensure that our words and actions are not just tied to seeking power. It is becoming acceptable and maybe even respected to speak up for women — that is great because it will help amplify women’s voices, but things won’t change until we are also willing to speak up when it is unpopular. Until male VCs realize that it is not just asking a woman to a hotel room for sex during a pitch meeting that is “crossing the line” but that all of the more subtle bias encountered by women every day is equally damaging over the long run, efforts to get more women into the industry are going to fall flat.

I appreciate that Reid Hoffman spoke out with a thoughtful and heartfelt post along with a request to create a #decencypledge and HR-like function for the industry. Given his influence it legitimized the path for others to speak out in support of change, which is great.

However, it still feels like we’re missing the mark with a big and important lesson here. The issue at play comes down to power dynamics. In particular in the instance with Caldbeck: a man with money to disburse (venture capitalist) and women seeking funding for their endeavors (entrepreneurs). It is clear he took advantage of this power dynamic. What’s unclear is whether he (or those around him) realized that there was actually anything wrong at the time and if they did why they didn’t speak up sooner.

The power dynamics in Silicon Valley leave the door open for abuse, and the culture has permitted this with a tacit stance of “that’s just the way it is.” Until we can get real with all of this, a politically-correct statement against gender-based harassment isn’t going to change much.

I saw a Facebook comment to Read Hoffman’s LinkedIn post that indicated the person was a bit perplexed by the need for a decency pledge simply because it should seems so obvious that we should be decent to each other as human beings without needing to pledge to do so.

The truth is, in Silicon Valley, entrepreneurs of both genders are taken advantage of by investors and also sometimes by better known (or more resourced) entrepreneurs. Yes there is a huge problem with getting more women into the industry and ensuring they are treated more fairly. This needs to be addressed — I know firsthand — but that also isn’t going to happen until we are willing to look at abusive power dynamics more broadly, between other types of actors and in more subtle ways.

People are piling onto Caldbeck because he did something wrong, but the reason they are piling on NOW is because he is toxic. He has lost his “power” because women were willing to come forward on the record and put their reputations at risk to do so — also because someone as influential as Hoffman backed up the story with his endorsement. It’s also a pretty clear cut “wrong” once you the see the story in black and white.

Its not so different from people piling on Travis Kalanick and Uber once it became fashionable to do so thanks to the visibility Susan Fowler was able to place on gender issues and to other incidents that became very public like the video of Kalanick’s argument with a driver.

In a sense these two guys — Caldbeck and Kalanick — have become lightning rods for issues that were just accepted as “the way business is done”, but they are not the only ones deserving of negative attention, and there are many, many people who endorse this sort of behavior in various ways for profit or influence. Or they perpetuate the more subtle behaviors that are equally damaging on a systemic level.

Countless other stories will never be known — and consequently many offenders will continue offending — because most often people decide it’s just not worth it to fight and the ones that do almost always get skewered by individuals and the press — unless they hold enough power or are endorsed by those who do. I’ve heard influential people warn against ever going up against an investor for wrongdoing because “in the history of Silicon Valley an entrepreneur has never won against an investor, justified or not.”

Perhaps the tides are turning, and in this instance and that of Susan Fowler with Uber, I’m glad to see that we are paying attention, however let’s not be seduced by the idea that there are just a few bad actors that we need to catch with an HR function. So much of what is wrong in the industry is much more subtle than this.

And the consequences for letting these behaviors continue are serious. They range from countless women being downright discouraged to serious mental and physical health impacts for entrepreneurs that are bullied and an unknown number of talented people that drop out of the industry altogether. All of these result in an ecosystem that is drained of some of its best potential, and given the pervasiveness of tech, a broader culture that is being influenced negatively by these values as well.

So how can we each start contributing toward change? Here’s a good start:

→ When you have the opportunity to work with, recommend, invest in or take money from someone, take the time to do due diligence on them, even if its a simple Google search with keywords like “fraud” or “harassment”. While we shouldn’t immediately believe everything we read, it can be a starting point to dig deeper, and as more people start speaking up, this type of information will be come easier to find. If it is clear the person behaves ethically, with good intention and doesn’t abuse their power, then consider proceeding. If not, then walk away regardless of how much money or influence they have or how much it would help you.

→ When you are first-hand witness to or are told directly about unethical behavior that abuses power dynamics, be brave enough to stand up in support of the person that is being disadvantaged. This can be by supporting them privately or publicly but whatever you do, don’t ignore it and certainly don’t stand against them, even if it means the opportunity increase your own power (money, influence, etc.) or if it risks your power to support them (reputation, etc.). Doing so only contributes to perpetuating a bad system and makes you part of the problem.

→ If you have a friend, colleague or acquaintance who is behaving unethically or has done so in the past, call them out directly in a one-to-one conversation. If someone reference checks them with you be honest in the most appropriate and ethical way. Even if you think it means losing them as a “friend”. It doesn’t. If the bad actor is willing to listen to you and work toward changing, they were worth having as a friend. If they aren’t, they weren’t worth having as a friend to begin with, no matter what social/professional credibility the “friendship” gave you. You would be doing both the person and the friendship a disservice by staying quiet. We can’t always see our blind spots or bad deeds on our own, and it is invaluable to have friends who will help you continue to learn and grow.

I can’t say I’ve always done all these things perfectly — I wish I would have helped surface these issues more publicly sooner, but the media firestorm around this shows that change are coming. If you are a friend of mine and think I miss on one of these at some point, please talk to me about it.

And, for those who are genuinely wondering how to play more fair in Silicon Valley and learn how to better recognize conscious and unconscious instances of bias and unethical power plays, please feel free to reach out. I’m happy to dedicate time to support…


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