What I Think We’re Talking About When We’re Talking About What We Can’t Talk About

It’s no longer worth it to vocalize controversial beliefs. Silicon Valley has become a PC echo chamber. I can’t say what I think without fear of reprisal.

These are not beliefs I personally hold but ones which I’ve heard expressed with increasing volume from people I know well and people I don’t know as well, in public spaces and in private conversations. Often these sentiments are expressed by 30 – 50 year old white men (and women) of economic privilege. I say this not to discredit their feelings or observations but because (a) it does seem to be relevant and (b) that’s the group which dominates my own social circles, which means that my POV is constrained by my own limitations in perspective.

But obviously since you’re reading this, I felt confident enough I had something to say that I’m wading into this conversation. Not to dissect a blog post.

Continue reading "What I Think We’re Talking About When We’re Talking About What We Can’t Talk About"

You Can’t Bullshit a Good VC, But You Can MAKE THEM BELIEVE

It’s the season of giving, so when my friend Nathan Bashaw asked for follow-up on my last post, well, I cracked open WordPress to deliver! Nathan wanted my POV on the difference between bullshitting to investors versus telling a BIG VISION CRAZY STORY.

So here we go…..

Bullshitting is telling prospective investors one story – what you think they want to hear and you’re not really committed to – while telling your team another story. Making Them Believe is articulating what your company has the chance to become, even if it’s dependent on lots of hard work and there’s lots of unknown between now and then. Remember, VCs are listening for what could happen if things go right, not wrong.

Bullshitting is building a spreadsheet with assumptions which

Continue reading "You Can’t Bullshit a Good VC, But You Can MAKE THEM BELIEVE"

To Raise a Venture Round These Days, You Need To Be a Little Crazy

None of our portfolio companies seeking additional dollars in 2017 had a “standard” venture fundraise. You know, the one where you advise the company “plan to take 2-3 months to get one or more term sheets and then another month to close.” Zero. Every one of them were feast or famine. 2-4 weeks to multiple termsheets (sometimes under a week!) or 4+ months of meetings and milestones before finding the additional capital (or in one or two cases, *not* finding the additional dollars) they needed.

The startups which took longer were mostly very solid businesses with quality teams. Companies where we would have certainly done our pro rata in a new round. My partner Satya summarized part of our reaction in this tweet:

Internet Content Moderation 101

Since Facebook, Twitter and YouTube have all been vocal (to various degrees) about staffing up the human element of their content moderation teams, here are a few things to understand about how these systems typically work. Most of this is based on my time at YouTube (which ended almost five years ago, so nothing here should be considered a definitive statement of current operations), but I found that most of our peer companies approached it similarly. Note, I’m going to focus on user generated/shared content, not advertising policies. It’s typical that ads have their own, separate criteria. This is more about text, images & video that a regular user would create, upload and publish.


What Is Meant By Content Moderation

Content Moderation or Content Review is typically a term applied to content (text, images, audio, video) that a user has uploaded, published or shared on a social platform. It’s distinct

Continue reading "Internet Content Moderation 101"

For VCs, “What Could Go Right” Is More Important Than “What Could Go Wrong”

You ever notice how when someone leads off by saying, “Now, I don’t mean to overgeneralize but…” they almost always are overgeneralizing? Now, I don’t mean to overgeneralize but I want to tell you about something that reporters and pundits frequently get wrong when evaluating the venture-worthiness of a failed startup. They focus on the answer to the question “what are all the things which could have gone wrong here” versus “how valuable would this company have been if things went right?”

VCs are in the business of backing companies that have a substantial chance of failing and the earlier you invest, the more likely you are to see a zero return on your capital. What offsets this is that the successes tend to be outsized, returning 20x, 50x, or even 100x+. The notion that tremendous value is created by a very small percentage of startups, and the financiers

Continue reading "For VCs, “What Could Go Right” Is More Important Than “What Could Go Wrong”"

Five Posts I Would Have Written If Someone Else Hadn’t

Flying back to San Francisco, spending some time in my Pocket since I rarely read anything when it’s actually published. Here are a bunch of posts that I enjoyed, most VC or startup related, so if you don’t care about that stuff, skip this.

The Angel’s in the Details – Andy Dunn, Walmart (Bonobos cofounder/CEO)

Andy is a ‘wears it on his sleeve’ type of guy and his writing is always passionate and personal. This post reminded me how much I hate when I hear a leader of any type say something like “well, you can’t expect me to know everything that’s going on” or “that happened below my paygrade” versus accepting responsibility.

Six Ways Great Companies Use Board Decks to Their Advantage – Union Square Ventures blog

Solid meat and potatoes post about good board decks. Board meetings can be some of the best discussions and informative sessions if

Continue reading "Five Posts I Would Have Written If Someone Else Hadn’t"

What I’ve Learned When I Ask For Feedback

Something NEW and TRUE. Every time I’ve asked for feedback from those around me in a structured format I’ve received a gift. A learning that was previously unknown to me (NEW) and, even if I want to deny it, 100% correct (TRUE). My first N&T arrived when I was in grad school as part of a semester long T-group with a dozen or so of my classmates. Here I learned about a way I was unintentionally creating resentment by making people feel judged and discarded. By acknowledging and understanding these reactions I was able to improve myself.

The second N&T emerged during a 360 Degree Assessment that I received upon making Director at Google. You know I heard? That I was actually a pretty shitty manager of people who had different communication styles and motivations than I did. So again, I took it to heart and evolved (and also made

Continue reading "What I’ve Learned When I Ask For Feedback"

Rafat Ali on Media Startups and the Nature of Venture

“1) VC money is not evil. 2) VC money is not sustainable.

Those are not contradictory statements.”

Those are Rafat Ali’s words from a post he wrote Friday in reaction to the cascade of bad news for a bunch of venture-backed new media companies. While Rafat’s expertise is concentrated in media (he started and sold Paid Content and now runs vertical travel startups Skift), the statements above apply generally (we’re investors in theSkimm and Cheddar, so clearly believe there is a place for venture here).

The most challenging aspect of taking venture capital is that it’s difficult to step off of the venture train once you’ve taken too much money, or negotiated too high a valuation, or gone too deep on executing a plan that requires high burn ahead of profitability. But complaining about that or assuming it’s fundamentally “evil,” is like getting married and then complaining it makes

Continue reading "Rafat Ali on Media Startups and the Nature of Venture"

If You Work at Google or Apple, I Need You To Read This Post About Charity & “FlashMobs for Good.”

There are 43 days left in 2017. That’s not many for any of us, but it’s an especially important countdown if you work at Google, Apple or any other tech company which has an employer match program for charitable donations. Have you maxed out your match yet? Please consider doing so and let me give you an idea for a fun way involving your team and colleagues.

During my last few years at YouTube we were able to raise tens of thousands of dollars in just a few hours by creating FlashMobs for Good where we turned charitable giving into a critical mass event. Here’s what we did and I’m hoping some of you will try this at your company:

  1. Pick a period of time (24 – 48 hours work best) and declare it a “FlashMob for Good” during which you’ll track the combined donations going from your company to
    Continue reading "If You Work at Google or Apple, I Need You To Read This Post About Charity & “FlashMobs for Good.”"

“Thoughts & Prayers” Won’t Change VC Diversity But Incentives Will. Supporting Female Founders Office Hours.

I hope some male VCs got scared yesterday, and if they didn’t, they should. Seeing Jess Lee of Sequoia bring together a group of amazing female investors as part of Female Founders Office Hours isn’t just about empowering women. It’s about keeping firms who don’t have female investing partners out of this dealflow. That’s not the stated intent of FFOH, which is about relationships and kicking off a “virtuous cycle of women helping women,” but hopefully a secondary effect of this group. And I think that’s great.

I’ve joked that if VCs found diversity as interesting as crypto we’d make much faster progress on solving gender and underrepresentation in our industry. VCs are market-driven — they’ll move towards opportunity with high velocity. Similarly they’ll seek to solve existential threats, otherwise they’re in the business of offense, not defense. Homebrew, my seed fund, doesn’t have a female GP – it’s

Continue reading "“Thoughts & Prayers” Won’t Change VC Diversity But Incentives Will. Supporting Female Founders Office Hours."

Virtual Assistants Are Still Vital to My Productivity But 2017 Was Ho-Hum

The Consumer Virtual Assistant landscape was pretty uneventful in 2017 but it felt more like business model stagnation than any limit in the longterm technologies. Humans are still involved in much of the supply-side fulfillment and, well, human labor is still expensive. In addition, I wonder if consumers will trust Apple, Google, Facebook and Amazon AI assistants to truly represent their best interests given ongoing investigations into bias in algorithms, designing for addiction (err i mean engagement), and the regulatory conversations occurring around 2016 elections.

My Year One 2015 summary and my Year Two 2016 summary


What Virtual Assistants did I rely upon in Year Three 2017?

Facebook Messenger M: While M moves more towards auto-replies, I believe I still have access to the fuller version of M that more closely resembles the original virtual assistant beta (remember when you could ask M to do nearly anything?).

Screen Shot 2017-11-11 at 11.58.43 AM
Continue reading "Virtual Assistants Are Still Vital to My Productivity But 2017 Was Ho-Hum"

Reinventing Political Ads: What If Facebook Went Further Than Regulators Were Asking

The “Honest Ads Act” is, well, boring. As a bipartisan proposal to evolve the way Facebook and other online platforms treat political ads it checks a bunch of boxes. Publicly available records of ad spend and the viewing metrics associated with the campaigns would be an improvement on today’s black box, but would this fundamentally change discourse in American politics? I don’t think so. And even if it helps limit foreign actors, we already see that many of the most destructive, controversial or half-true campaign ads come from within our own borders!


“Honest Ads” and Twitter’s proposed Transparency Center are like putting bandaids on a patient who’s bleeding out. Why can’t Facebook aim higher than regulators when it comes to putting forth a POV on their own platform? What if Facebook set out to create a new ethical high ground? Enter the Constructive Campaigns Pledge.

One: Create the Carrot. Imagine

pig mud
Continue reading "Reinventing Political Ads: What If Facebook Went Further Than Regulators Were Asking"

Productivity Hack: Read One Chapter of a Book to Get 90% of the Value

Here’s a fairly reliable productivity hack if you’ve picked up the latest self-help, management theory or sweeping sociological interpretation of our times: only read the second chapter because it routinely contains 90% of the book’s value. Here’s how these books usually go:

Forward by Influencer – obviously SKIP

Chapter 1: Author’s Credentials – author introduced themselves, makes case for why they’re qualified, and evangelizes their path to discovery of their new idea

Chapter 2: THE IDEA

Chapters 3+: Examples of THE IDEA in action and/or anecdotal stories to validate the universality of THE IDEA


Note, sometimes Chapter 2 can be Chapter 3, but you can usually figure this out by looking at the Table of Contents.

Happy semi-reading!


My Favorite Instagram Accounts: Coffee and Notebooks

My Instagram feed is purposefully dominated by coffee cups and notebooks (the paper kind). If you like these things too, here are some of my favorite accounts. If you know of other folks I should be following, let me know!





















Notebooks, Notebook Art










Arts, Design






Part 2: How To Not Lose Female Engineering Candidates

Like I said yesterday, I’m thankful for my smart friends. After Paradigm’s Joelle Emerson provided some feedback on how Take-Home Code Projects might impact gender ratios in hiring pipelines, another amazing woman sent me her perspectives. Kieran Synder is CEO of Textio, an innovative Seattle startup which helps companies understand the language of their job listings. Kieran’s email, which she’s letting me publish here:

“We do a take-home project too, longer than 3-4 hours actually. We have not had women pass at a higher or lower rate than men, nor have we had anyone other than one man decide not to move on in the process after seeing the question. We’ve been doing this for three years – and we do take-home projects of similar character for every role (obviously, for non-engineer roles, the project is something other than coding).

They Wanted To Eliminate Gender Bias In Technical Hiring But Ended Up Losing All Their Female Candidates.

One of our most recent seed investments recently posed a question to me. They had designed a technical hiring process to try and eliminate gender bias but were losing all the women midway through their funnel when a take-home project was introduced. What was going wrong?

I reviewed their current approaches alongside Homebrew’s Head of Talent Beth Scheer and we made a few recommendations, but there was nothing glaringly broken. Attention then turned to the take-home project since that’s where the breakage seemed to be most acute. Was there something about this step that was unintentionally sending the wrong signal to female engineers? This wasn’t my area of expertise but I’m fortunate to have smart friends so I asked Joelle Emerson, founder of Paradigm, a leading consultancy providing training and strategy around inclusion. Her response was, not surprisingly, really great and she agreed to let me publish it

Continue reading "They Wanted To Eliminate Gender Bias In Technical Hiring But Ended Up Losing All Their Female Candidates."

How Becoming a Dad Helped Me Become a VC

“Don’t stop asking me what it’s like to be a mom and an executive, just start asking dads the same question.” I can’t recall the conference or, unfortunately, the specific woman, but I remember being struck by this answer (which was in response to some rote ‘so, what’s it like being a CEO and a mom?’ question). This was before I became a parent myself but it felt right. More honest and open than pretending we’re not impacted, in all sorts of ways, by becoming a parent.


Our daughter arrived early in 2012 and she was instrumental in my decision to leave Google and start a venture fund with my good friend and former colleague Satya Patel. Homebrew was about living my most authentic life. Google – still a great job and great company – had become a stable but not always enjoyable place for me and I

Continue reading "How Becoming a Dad Helped Me Become a VC"

What I Learned Backing Female Founders: Every One Has a #MeToo Story


When the #MeToo hashtag broke wide, one of the consistent remarks from men was “wow, feels like every woman I know has been harassed in some form.” And the consistent reaction from women was, “well, duh. Did you not know that?”

My own journey from the Land of Naive Male occurred earlier this decade, and it came from backing enough female founders to see a trend emerge. Homebrew will be five years old in April but we seem to fund companies with a female founder ~3-4x more frequently than our industry as a whole (~15-20% vs ~5%).

Here’s what Hunter thought on Day One of Homebrew: “All female founders know of a female founder who has experienced some form of harassment.”

Here’s what Hunter realized after funding a number of female founders and being trusted enough to hear their stories: “All female founders have experienced some

Continue reading "What I Learned Backing Female Founders: Every One Has a #MeToo Story"

What It’s Like Attending the New York Times “Page One” Meeting

A few weeks back my friend Millie Tran invited me to attend the daily morning News meeting at the New York Times. I’ve been a HUGE Times fanboy since growing up in NY and while I’ve had the chance to visit their offices many times, I’d never seen the inner workings like this. Well, at least not outside of the famous documentary Page One (the morning news meeting *used* to be called the “Page One” meeting during the Times’ more print-centric days).


Scene from the Page One meeting, circa 2003

What I didn’t tell Millie was that I wouldn’t be attending alone. You see, when I travel my daughter gives me one of her stuffed animals to take along and send her back pictures of our adventures together.

bunny times

The News meeting is staffed in-person by all the top editors and called into by the Washington bureau and any other editorial

bunny times 2
daily bugle
Continue reading "What It’s Like Attending the New York Times “Page One” Meeting"

How Tech for Campaigns Has Helped 3,000+ Techies Make a Difference in Progressive Politics

I met Jessica Alter when she was running FounderDating, which helped solo founders discover their perfect cofounders. Like many of us, the 2016 Presidential Election alarmed her, but unlike many of us, she’s doing something more than just rage tweeting. Jessica, along with two cofounders, started Tech for Campaigns, which connects tech volunteers with the campaigns of progressive candidates for skill-based volunteering. Their momentum has been impressive and I’m a donor, so wanted to learn and share a bit more.

Hunter Walk: For folks just learning about this effort, what is Tech for Campaigns? How’d it get started? Where is it now?

Jessica Alter: Tech for Campaigns (TFC) is the digital arm for centrist and progressives. TFC brings digital and tech to down ballot political campaigns – both by building shared technical solutions and by matching our community of 3,000 tech volunteers campaigns. We have 50 campaign projects projects

Continue reading "How Tech for Campaigns Has Helped 3,000+ Techies Make a Difference in Progressive Politics"