• What’s past is prologue

    What’s past is prologue

    “[W]hat’s past is prologue, what to come
    In yours and my discharge.”

    William Shakespeare, The Tempest. Act 2, Scene 1.

    My favorite movie President of all time is Jeff Bridges in Rod Lurie’s The Contender. (I’m in good company: a far-more-qualified authority than me feels the same way: Barack Obama. Fortunately, I was on record as early as 2002 praising Bridges’ POTUS – I’m no bandwagon fan!)

    In the more than two decades since seeing the film the first time, it turns out my favorite scene isn’t even in the movie: it’s one of the deleted scenes, included on the DVD:

    (Deleted scene from The Contender. A full transcript of the scene is here; I’ve been obsessed with this scene for decades.)

    You see variations on this behavior in lots of places: “we do things this way because this is how we’ve always done them.” Sure, I’ve seen this in government – but it’s no less evident in the private sector. For better or worse, teams come to the same conclusion that Shakespeare did all those years ago: past is prologue: that’s how we did things before, it’s how we’ll do things now.

    It shouldn’t be a surprise to anyone reading this blog that I agree with Bridges on this one: if your actions today are entirely defined by what others did before, the best you could hope to achieve is exactly the same outcome as before. (The worst part of President Evans’ anecdote: noone had any idea why they were doing things the way they were: it was just how things were done.)

    In a world where we simply let the past be our prologue, the outcomes almost never matter – and any successes will be accidental at best. If you instead focus on the outcomes – what you’re trying to achieve – then the tactics (how you’ll get there) will present themselves.

    Don’t be an ape.

    PS: the featured image for this post is by none other than the Dude himself, Jeff Bridges, taken on the set of The Contender with Gary Oldman. If you weren’t aware that he is an accomplished photographer – and publishes photos from nearly every movie set he’s been on – you should check out his prints.

    Photo by Jeff Bridges, at jeffbridges.com
  • Binary: Good for code, bad for OKRs

    Binary: Good for code, bad for OKRs

    (Each week, I write a post about OKRs. You can see the series of posts here; if you have a question about OKRs you’d like to see me cover down the road, drop me a line.)

    macbook pro beside black speaker
    Photo by Ricardo Ortiz on Pexels.com

    A founder I’ve known for several years reached out recently. They had just raised a round, they’d onboarded a number of new team members, and he wanted to ensure his growing team was as aligned as possible. Attached to his email was their draft Q1 OKRs; he asked if I had any feedback.

    It takes at least two to four quarters for OKRs to really stick in an organization. Like learning any new skill, it takes time to develop the muscle memory. Teams need to see what success looks like, but also to see how the organization responds to failure: when a low score on an OKR isn’t stigmatized or penalized, it reinforces the idea that failure is data, and can contribute to future successes.

    Back to the founder: their first quarter’s OKRs were quite good: they had metrics associated with a number of their goals, they didn’t over-commit to too many company-level objectives, and there was clear alignment across teams. For a first effort, it was pretty impressive! But there was one big issue – a common mistake that many teams make early in their implementation of OKRs: a series of binary key results.

    What do I mean by binary key results? Things like “launch v1 of [product]”, “develop roadmap for [other product]”, “decide what to do about [issue]” – these are initiatives that have only two possible outcomes: you either did the thing, or you didn’t. When it comes time to score these “OKRs”, you either get a zero or a one.

    What if you launched v1 of the product and it sucked? What if you develop a roadmap for some big idea and… nothing happened? The fatal flaw in committing to OKRs like these is that you can get a great score on the OKR when it’s time to grade yourselves, and fail to achieve much (or, worse: actively do damage to your organization).

    Baked into many of these binary goals is a hypothesis: if we do this [ship/decide/develop], then this [other good thing] will happen. What you and your team should do is try to articulate what that other good thing is, and build your OKRs around that. When you do that, you’re focusing your team on the outcome you’re trying to provoke, not the tactic that you think might produce that outcome. (You could be right! You might be wrong. Ultimately, it doesn’t matter: it’s the outcome you should care about.)

    By avoiding a binary OKR, you’re helping the team appreciate that the point of adopting OKRs is to get better at tying the work they do to the outcomes that matter. And you’ll avoid situations where good grades on the OKRs aren’t well-calibrated to the organization’s performance overall – among other things, good scores that nevertheless produce bad outcomes can teach a team that OKRs don’t work.

  • “I am not a racist”​ is not the same as “there is no racism”​

    “I am not a racist”​ is not the same as “there is no racism”​

    (This is a slightly-edited repost of an essay I originally posted on LinkedIn in 2020.)

    For the longest time, I thought about racism in an individual context: if I didn’t express racist feelings, or see them expressed, it was hard to imagine that “racism” was widespread, or if it was real, that it was my responsibility to address it.

    But “I am not racist” can be true and “racism is widespread and a problem” can also be true. As my former co-worker Terri Burns so eloquently put in the BLCK.VC event in 2020, systems in the US aren’t broken, they are working as intended. I, as a white person, have benefited from racist systems. For example: 

    When my Grandparents bought their first house in the early 1940s, they were beneficiaries of relaxed lending practices made possible by the National Housing Act of 1934. A precursor to the Fair Housing Act of the 60s, the NHA established a practice that would later become known as redlining – making it possible for White home buyers to secure mortgages, excluding Black Americans from doing the same. For decades.

    The single biggest contributor to generational wealth in America? Home ownership. By explicitly enabling White Americans like my Grandparents to buy homes – starting in the 30s and 40s and carrying through to the 80s – the federal housing system significantly contributed to the disparity in net worth between Black families and White families (today, that gap is roughly 10x).

    When Americans like my Grandfather returned from WWII, Congress created the GI Bill to help soldiers afford college (second biggest contributor to a family’s net worth? A college education!) and buy homes. To get it passed into law, the Bill’s sponsors made concessions to Southern politicians that ensured many of the GI Bill’s benefits would be unavailable to Black soldiers. The result? White soldiers saw their future earnings grow and were able to buy homes at rates that dwarfed those of their fellow Black veterans, accelerating the wealth gap even as the Civil Rights era appeared to create new opportunities for Black Americans.

    Sticking with education: K-12 schools in the U.S. are disproportionately funded by local property taxes, which itself only serves to compound disparities between neighborhoods. Those same neighborhoods that had previously been punished through redlining today face dramatically lower school funding – which only serves to widen the achievement gap between wealthy (often White) and poor (often Black) communities. And when those students graduate from high school and apply to college, they’re penalized a second time, as their admission to college is almost always influenced by their standardized test scores – which reveal ongoing, systemic racial gaps between White and Black students.

    Richard Nixon’s “law and order” strategy in the 70s, Ronald Reagan’s war on drugs in the 80s, and Bill Clinton’s “three strikes and you’re out” policy in the 90s: all together, by 2010 the United States incarcerated a larger percentage of its Black population than South Africa did at the height of Apartheid. With less than 5% of the world’s population, we had 25% of the world’s prisoners. Not only had we denied economic opportunity through housing and education policy for generations, we then put nearly 8% of Black Americans under criminal supervision – limiting their eligibility for housing, food, and job assistance, among many others. Those under criminal supervision also lose their right to vote – depending on the state, some convicted of a felony lose their right to vote permanently. Denied access to opportunity, denied assistance that might help them get back on their feet – even after paying their debt to society – these citizens are then denied representation by prohibiting them for voting for their elected officials.

    None of this addresses the ongoing, post-Reconstruction campaign of racial terror carried out by Whites towards Blacks, but it must be mentioned: while these policies and systems were denying fundamental rights to Black Americans, between 1877 and 1950, over 4,000 Black Americans were lynched by Whites. Of all lynchings carried out after 1900, just 1% of those murderers were convicted of a crimeMany lynchings were announced in advance. In newspapers. Carried out in public, before crowds of hundreds or thousands of White Americans.

    It was only as I came to acknowledge these tragic, deeply uncomfortable facts, and accepted that I had – directly or otherwise – benefited from them, that I grew motivated to change them. I am not a racist, but there is racism. Facing this reality – understanding the deep, fundamental nature of the systemic barriers we as a nation have placed over generations, some of which, like mass incarceration, played out in my lifetime – is why I decided to commit more of my own time to (a) acknowledging and calling attention to injustices when I see them, (b) advocating for change with elected officials, and (c) investing time and money with organizations actively working to dismantle these systems.

    Black lives matter.

  • Leaders: stop making decisions

    I adore this observation over the weekend from my friend Punit Soni:

    A practical way to become a better leader is to review at regular intervals all the decisions that need to come to you. And cut them by 50% through either delegation or automation.

    I’ve never heard this notion captured in this way (though it’s a spiritual cousin to my old boss’s maxim that CEOs need to constantly fire themselves), and I like what Punit is getting at. Following up on last week’s OKRs post, the best leaders find ways of pushing decision-making down into the org – if their teams know what’s expected, and how to evaluate options, they’ll be able to act on the leader’s behalf without her being involved in every decision.

    What I like so much about Punit’s approach is the intention behind it: capture the decisions you’ve made as a leader over the last quarter, and then think about how you’d avoid having to make a similar decision in the future. Note: this isn’t the same as avoiding the decision getting made: the goal is to avoid the leader becoming the bottleneck to the org’s execution. The fewer decisions the leader needs to make, the faster all decisions get made. The more predictable the leader’s approach to prioritization and alignment, the more consistent and complementary those decisions are – across the org.

    Later in his post, Punit puts some metrics to how to approach this:

    People think being a CEO is 50% decision making, rest inspiring and recruiting or other strategic tasks. It is actually 5% decision making, and then the rest.

    Spending time really fine tuning that 5% is critical. Giving up control (not oversight) on the rest is as critical.

    Looking forward to applying this to my own approach to decision-making in the future.

  • Throw away the rabbits

    Throw away the rabbits

    (Each week, I write a post about OKRs. You can see the series of posts here; if you have a question about OKRs you’d like to see me cover down the road, drop me a line.)

    Earlier this month, Kara Swisher interviewed my old boss Dick Costolo on her podcast, Sway. The entire episode is worth listening to:

    Twitter’s Former C.E.O. Has a ‘Too Bad, So Sad’ Approach to Content Moderation
    Sway, 1/3/2021

    Something in particular Dick said really struck me:

    [Your managers] have to understand what you understand.

    This is the same point I made in my MIT Sloan Management Review interview last fall with Chris Clearfield:

    As a leader, you want to be predictable. You want people to understand where you’re trying to lead the organization and why.

    OKRs are all about creating a shared framework, a language, for understanding what the organization prioritizes, how it prioritizes, and why it prioritizes some things above others. In the absence of a framework like OKRs, picking some things to work on (and not others) can feel political, even mercurial: is the CEO picking that project because she likes the person who suggested it better than me? Why aren’t we working on this other thing, that seems more important to me?

    When a team implements OKRs, the what, the how, and the why all come into focus. There’s a method to what the org cares about, a consistency to how the decisions get made, that resonates. The team doesn’t have to always agree with those decisions, but they should always understand those decisions. Teams that understand why their CEO made the decisions she made will, in my experience, trust her. They’ll execute more consistently, and more quickly. They’ll be aligned.

    That’s what Dick was getting at with Kara. When I worked for Dick at FeedBurner all those years ago, we knew what business we were in and why. He even wrote about this for Brad Feld and David Cohen in their book Do More Faster:

    When FeedBurner was starting to become popular in 2005, and we’d hired our first director of business development, Rick Klau (now a partner at Google Ventures), he would occasionally come to my desk and say, “Company X will pay us an extraordinary amount of money to do this thing with their feeds. We’ve never really talked about that before, but it could be a good opportunity and it’s really a ton of money.” My reaction, which eventually became Rick’s reaction, was “Do we have all the feeds yet? No? Okay, then let’s just focus on getting all the feeds. Step one is to get all the feeds. Don’t bring me a rabbit; bring me more feeds. Throw away the rabbits.”

    Teams make dozens of decisions a day about what to do, how to do it, and what not to do. The more dysfunctional the organization, the more those decisions get bumped up the ladder, asking for someone more senior to decide – either because they don’t believe they have the authority to make it themselves, or because they just don’t know what their leadership would do. Leaders who help their teams understand what they care most about – and why – empower their teams to make those decisions. The team won’t have to ask for permission: they’ll understand what the CEO would say if she’d been in the room – and they’ll have the benefit of moving more quickly in the process. (Not every decision is clear-cut: those can and should get escalated.)

    It’s not just the team trusting the CEO. The leader who knows that her team has internalized this framework – who understands that for now, their job is to throw away the rabbits – will trust her team to consistently execute on that shared vision. She won’t second-guess the decisions that are getting made day-to-day, that she’s not included in.

  • Let’s stop saying these two things

    In a recent team meeting, I said what felt like a pretty innocuous statement about an upcoming goal. But in the days since, I’ve heard from several folks on the team that they heard what I said very differently than I’d intended. Not because they don’t trust me (thankfully), but because they’ve been on the team longer, and their history with the team informed how they interpreted what I said. I was grateful for the feedback, and am glad to have had the reminder. What you say isn’t always what people hear – and while that doesn’t necessarily mean you’re responsible for how they hear what you say, it can still result in diluting the impact of your words, or worse, lead people to tune you out.

    With that in mind, there are a couple phrases that I hear on a regular basis that I know people don’t intend me to hear the way I hear them. In both cases, there are easy alternatives to the phrases that would preserve the speaker’s intent, and eliminate any potential negative association. And in both cases, the negative association is really negative.

    Drinking the Kool-Aid. We’ve all heard this, countless times, as a generic expression of “I’m in!” I kept count: I heard it three times last week, in three different meetings, about three different initiatives. In each case, the speaker was conveying enthusiasm, and an endorsement of the person advocating for the idea. To a person, they meant well.

    But I don’t hear that. When I hear “drinking the Kool-Aid”, I think about Leo Ryan, Jackie Speier, and 900+ dead followers of Jim Jones.

    Leo Ryan was the US Congressman representing much of San Mateo county. A number of his constituents had family members who’d joined Jim Jones’ People’s Temple and followed Jones to Guyana, where the families had lost contact. As his constituents’ concerns grew, and Les Kingsolving’s 4-day SF Examiner investigation made clear that all was not well with the People’s Temple, Ryan committed to visiting Jonestown to see for himself. (An aside: this was not Ryan’s first experience with directly observing a situation to form his own opinion. From his Wikipedia page: “In 1970, using a pseudonym, Ryan had himself arrested, detained, and strip-searched to investigate conditions in California’s prisons. He stayed for ten days as an inmate at Folsom State Prison while presiding as chairman on the Assembly committee that oversaw prison reform.” Damn.)

    Ryan’s delegation – which included future Bay Area Congresswoman Jackie Speier – was ambushed on an airstrip. Congressman Ryan was assassinated, shot 20 times. Four others – three journalists, and a defecting cult member – were also killed. Ryan’s aide (Speier) and eight others were wounded. That evening, convinced the US government was about to attack, Jones provided his congregation with cyanide-laced Flavor Aid. Many consumed it willingly; those who didn’t were injected with cyanide, or shot. In all, more than 900 were dead by morning. 300 of those dead were children. It was, until 9/11, the greatest single loss of American civilian life in a deliberate act.

    When I hear “drinking the Kool-Aid”, I can’t help but think of the horrors of that evening, the impact it must have had on the Bay Area at the time, or what must be horrifically painful memories for the families who lost loved ones 43 years ago. (On this, I highly recommend Season of the Witch, a compelling narration of San Francisco from the late 60s to the early 80s.) There are so many better ways to say you’re excited about something.

    Grandfathered in. Another common phrase, it means that the terms of a previous policy are being applied to a current scenario, even though the current policy would handle the scenario differently.

    What’s so terrible about this phrase is which policy it originally referred to: the Southern states’ reaction to the passage of the Fifteenth Amendment in 1870, which prohibited racial discrimination in voting. In response, a number of states passed laws that created various, non-racial obstacles to registering to vote (literacy tests, poll taxes, etc.) – simultaneously waiving those obstacles if an individual had been eligible prior to 1867, or were lineal descendants of voters at that time.

    In other words: if your white grandfather was eligible to vote prior to the passage of the Fifteenth Amendment, you were eligible to vote. When you talk about being grandfathered in, that’s what you’re referring to.

    Call it a legacy, an exemption. PracticalESG has some other suggestions. Just don’t explicitly recall the disenfranchisement of Black Americans in the South that lasted for nearly a century after the Constitutional Amendment explicitly designed to enfranchise them.

  • Gender, promotions, and the stratosphere

    Several years ago, my oldest son was in an engineering class at his high school. His teacher knew I worked in venture capital, and asked if I’d speak to the class about my work. With my son’s permission, I agreed. As much fun as I had – the kids asked great questions – it was depressing to see that in an engineering classroom of 30+ students at this public high school, the chairs in the room were filled by 90% boys. I’ve written before about my focus on gender equity, and it was frustrating to see some of the same dynamics laid out so plainly in an entirely different setting.

    My wife and I set out to do something about it; we met with the school district, and asked if they’d be open to partnering with us to address the gender balance in high school STEM classes. This post isn’t about that work – that deserves its own post (or two!). But during an annual update call with the school district today where they presented their progress and invited feedback, I was reminded of an episode in Google’s history that I’m always surprised more people aren’t aware of.

    The gist of the issue (from a 2014 Washington Post interview with Laszlo Bock, then Google’s SVP / People Operations):

    Four years ago, Google was confronted with a troubling stat: Its male engineers were raising their hands for promotions at higher rates than women. Google couldn’t understand why women weren’t going for better titles and higher pay when it had a system where anyone could apply for a promotion.

    Laszlo and his team were aware of compelling research on gender inequity that surfaced two relevant facts:

    1) Girls don’t raise their hands as often as boys when answering math problems, even though they have a higher rate of accuracy when they do.

    2) Women don’t offer up their ideas as often as men in business meetings, even though observers say their thoughts are often better than the many offered by their male colleagues.

    So they tried a nudge to see if they could improve the top of the promotion funnel problem:

    Bock tried an experiment. Alan Eustace, one of the heads of engineering, sent an e-mail to his staff describing the two studies and then reminding them it was time to apply for promotions. Immediately, the application rate for women soared and the rate of women who received promotions rose higher than that for male engineers. Every time Eustace sent the same e-mail reminder, female promotion rates climbed.

    There’s a lot more in the interview that’s worth reading (including the explicit acknowledgement that Google’s record on gender equity was mixed – at best).

    By the way: that fall, the same Alan Eustace took a sabbatical, and set a world record in the process.

    Alan’s spacesuit.
    photo by: Balon Greyjoy, CC0, via Wikimedia Commons

    While on sabbatical, Alan didn’t send that email. You can guess what happened to promotion rates. In subsequent years, Google formalized this communication, and while I wasn’t always privy to the nudges the people ops team used – I was at Google Ventures, which was not actually part of Google, but a sister company that was part of Google’s parent, Alphabet – I heard from them on occasion about ongoing efforts to use data to drive decisions with the goal of driving outcomes they could be proud of.

    This approach – look at the data, understand the circumstances that produced the data, create thoughtful goals that reflect the outcomes you want, then get creative about what you can do to make those outcomes more likely – is completely portable to any number of other situations. Laszlo’s book – Work Rules! – is excellent if you want to dig in further.

  • What my OKRs video got wrong

    (Each week, I write a post about OKRs. You can see the series of posts here; if you have a question about OKRs you’d like to see me cover down the road, drop me a line.)

    When I resurrected this blog, Michael was one of the first commenters who asked:

    Any chance you could do a follow up post on OKRs? I would love to know whether you discovered something new about OKRs since publishing the GV post on Medium.

    The Medium post in question is here; there’s not much to the post, other than the embed of the video I originally made in 2012 that now has over 1M views on YouTube. (If you don’t know what OKRs are, starting with that video isn’t the worst introduction. Though note that the purpose of this post is to update some things I think could be better.)

    A while back, I wrote on Twitter about a few things I would do differently if I were recording the video today; it’s been a few years since then, so consider this my periodic update to the video:

    1. What you and your team say no to is at least as important as what you say yes to. This is (at best) implicit in the video, as I talk about the importance of setting a few objectives (and, by extension, saying no to others). But the more time I’ve spent with teams who are implementing OKRs, including the last couple quarters with my current team, it’s clear to me that one of the biggest near-term values of committing to this framework is the permission to your team to say no to lots of good ideas. (This deserves its own post; I’ll flesh this out in the weeks ahead.)
    2. If you’re implementing OKRs for the first time, or the team is still learning how to work with OKRs, ignore individual OKRs. There just isn’t enough difference between what the group is committed to delivering and what the individual’s contribution to that commitment is for individual OKRs to add a lot of value. They end up confusing / frustrating people, or they feel redundant – which can give people a reason to write off OKRs altogether. Give the team a chance to see OKRs work well at aligning the teams across the org, and seeing the kind of larger impact that’s possible when those commitments produce compounding impact, before you worry too much about encouraging individuals to spend much time thinking about their individual OKRs. (And even then, maybe make them optional.)
    3. When identifying metrics for your key results, make sure they quantify impact and/or outcomes, not progress. Metrics that just capture the work in progress – the number of tasks, the lines of code, the incremental effort – but which are disconnected from the actual goal are ultimately unhelpful, and may even be counterproductive. Metrics that suggest momentum and progress, but which fail to lead to the ambitious outcomes the team committed to, can really kill a team’s confidence. (It should be noted: some of the example OKRs I included in the video are, well, not great!)
    4. OKRs should not do double-duty as your performance review system. I noted this in the original blog post about the video, but it really needs to be shouted from the rafters: if you use OKRs as a performance review (which often has a compensation component tied to it), you’re going to encourage your teams to sandbag their OKRs, and set entirely achievable goals so they can get their bonus. You’ll punish ambition – only the people who get 100% of their targets will get 100% of their bonus. That is entirely counter to the idea that OKRs (at least as embodied at Google, and as I embraced them in this video) should reflect ambitious goals, goals that you’re not at all confident you can achieve (but if you did achieve, would be amazing). Sure, an individual’s contributions to a team’s accomplishments (as captured in their OKRs) can and should be an input to their overall performance review. But if they’re toxic in the workplace, if they demean coworkers, if they fail to uphold the organization’s values as they deliver those results? Your performance review approach has to have the ability to capture those counter-productive contributions to the overall organization, or your hands will be tied and your culture will suffer.

    While I’m on the subject of what the video got wrong, I can’t end this post without pointing you to Felipe Castro’s suggestion that the video needs to be retired altogether. Felipe said my tweetstorm linked above should have been a blog post, which… here I am! Better late than never. 😂 Kidding aside, Felipe raises a number of solid points – including that the football example I included in the video is too rigid. (In my defense, I was showing the original slides John Doerr had presented to Google’s leadership in 1999 to anchor everyone on how OKRs were introduced to Google – but yeah, looking back on it, I didn’t exactly put together original content to capture 13 years of evolution in how Google applied OKRs. A missed opportunity.) Thankfully, John updated his football example in his book Measure What Matters, one of many good reasons to read that if you haven’t already. Bottom line: there are far more rules and structure in a football game than there are in a company’s journey. The analogy breaks down pretty quickly. Anyway, give Felipe’s post a read.

    In the nearly ten years since I recorded that video, I’ve talked with hundreds of founders and leadership teams about implementing OKRs. I helped a number of Google Ventures portfolio companies implement them, and we’re in the process of adopting OKRs on my team at CDT. In the months ahead, I’ll write up the answers to the questions I get the most often, examples of what it looks like when they’re working well, and more. If you have a question about OKRs you’d like me to cover, drop me a line.

  • “A Triumph”

    “The fact that the system exists in any form is a triumph for a loose coalition of technologists, nonprofit groups and mostly Democratic states that championed the development of a digital vaccine card even before the first coronavirus shots were administered.”

    David Ingram, NBC News

    This article is a great overview on the progress to date on SMART Health Cards, something we’ve worked very hard on in California, alongside a number of other states, technology companies, health care providers, and pharmacies. It’s thrilling to see this take shape.

  • I owe my career to the Dean Campaign

    A couple years ago, the Dean of the Robbins School at University of Richmond invited me to campus to participate in the Robins Speaker Series. (I’m a Richmond Law alum.) I had a great time, especially with a series of excellent questions asked by students in the second half of my talk. But I want to talk about the first 20 minutes or so of the talk, where I talked about a series of entirely unpredictable events that started with a voicemail I left with a long-shot presidential campaign in Burlington, Vermont, and how it led to a career in product management at Google, then led to nearly a decade in venture capital. (Even later, after this talk: I can trace getting appointed by Governor Gavin Newsom to be the Chief Technology Innovation Officer for the state of California directly back to that phone call.) First, the talk (relevant portion starts around the 6 minute mark and goes to around the 25 minute mark):

    About that voicemail. Less than a year after I started this blog, I read an article in the Economist about a little-known Governor who was saying things that piqued my interest. (I checked: sure enough, I blogged about it here.) Soon after, I called directory assistance (!) to get a phone number for the campaign – ironically enough, the campaign that would become synonymous with the Internet didn’t have a website yet. The operator actually laughed at me –everyone in Burlington knew the governor, and the thought of him running for President tickled her to no end.

    I got an answering machine – it didn’t seem likely that I’d hear back. Surely they had more important things to attend to? But a week or two later, I got a call back from none other than Gov. Dean’s campaign manager, Joe Trippi. I had no way of knowing at the time, but every major step in my career would track back to that phone call. (Farhad Manjoo, writing for Salon at the time, wrote up a good account of those early days.)

    Volunteering on the Dean campaign was a phenomenal experience. I worked (virtually) alongside Gov. Dean’s tech team for more than a year; for my birthday in 2003, I gave myself a flight to Burlington and spent a long weekend working out of campaign HQ. After the Dean campaign imploded, some of that team got hired by a state Senator who was a long-shot candidate for US Senate in Illinois, Barack Obama. Because I was in Illinois and the tech team was in DC, the tech team asked if I’d consult; you know how that Senate race played out. Many of the folks – staff and outside consultants – would reassemble in 2008 when Sen. Obama announced he was running for President.

    By then, Google had purchased FeedBurner, the Chicago-based startup I’d been working for for three years. Google moved me to California, thwarting my goal of spending every waking hour in Obama HQ in Chicago. After a call with some of the friends on the Obama ’08 campaign (who I’d met on the Obama Senate campaign), I built the superdelegates.org site… which ended up getting featured on CNN by Abbi Tatton:

    Ginny Hunt – a friend from the Dean Campaign – was by this point working in Google’s DC office. She saw the CNN piece, and mentioned in passing to her colleagues on Google’s policy team that the Rick Klau mentioned in the story actually worked at Google on the main campus. A week later, Larry Page (yes, that Larry Page) demoed my side project at TGIF in front of the entire company.

    That’s how I ended up with a 20% project of my own – managing Google’s partnership at the Democratic Convention in Denver. It was there I met Katie Stanton, at the time a PM at Google, who was also a political junkie. We hit it off. I’d known from the day I started at Google that I wanted to be a PM – but I also knew that my lack of a computer science degree meant that was an all but impossible goal.

    Months after the convention, Katie IM’d me out of the blue and told me her friend Joe was looking for a PM on Blogger. I was of course deeply familiar with the product – as mentioned last week, I started my blog on Blogger in 2001. Working on Blogger would be a dream job! But the lack of a CS degree seemed to mean it would be a non-starter. She insisted on introducing me to Joe Kraus, then the VP in the department where Blogger lived. Joe and I met, and not long after, Joe asked Sergey Brin to make an exception to the CS requirement (amazingly, he did), and before the end of the year, I was a PM. Running Blogger. 🤯

    Not quite three years later, Joe and I met for lunch. I’d joined YouTube in January to be the PM on YouTube’s homepage, and after I finished telling him how much I loved it, he apologized and said that I needed to join him at Google Ventures. (One more small world connection: while at YouTube, in prep for a product launch, I met with the comms team to do some media training. Leading that training? Abbi Tatton – the same Abbi Tatton who’d profiled superdelegates.org when she worked at CNN years earlier – was now part of YouTube’s communications team. The interview I was prepping for? It was with Farhad Manjoo, the journalist I’d first crossed paths with when he was writing about the Dean campaign.)

    2022 Update: I gave the talk above in 2018, when I’d been at GV for just over 7 years. I stayed at GV another two years before leaving… but the Dean campaign wasn’t done with me yet.

    In 2012, a friend from the Dean campaign reached out to introduce me to Jen Pahlka, who’d founded Code for America a few years prior. I’d actually met Jen (briefly) at an Obama fundraiser a month before this outreach, but the follow-up introduction was the nudge I needed to get to know her. We became friends. I got involved in CfA as a mentor, and stayed in touch with Jen over the years. After I left Google Ventures, I pinged Jen to let her know that while I had some time off, I was eager to volunteer with anyone who could use help. That evening, Jen connected me to Amy Tong, then the CIO at the state of California. I was on my first call at 7am the next morning; after 6 weeks of 18 hours/day / 7 days/week volunteering on the state’s vaccination effort, I was appointed by Gov. Newsom to my current role. I’ve been here since.

    If I don’t make that phone call to Burlington, I don’t meet Joe, don’t volunteer for the campaign, don’t meet the Dean tech team, don’t work on the Obama Senate campaign, don’t volunteer on Obama’s ’08 campaign, don’t manage Google’s partnership at the DNC, don’t meet Katie, don’t meet Joe, don’t go to Blogger, then GV, don’t meet Jen, don’t meet Amy, don’t get appointed by Gov. Newsom.

    Who knows what your next phone call could lead to?

    Thanks to Tim Urban for the inspiration behind this post: