Succeeding in Venture Capital as an Introvert

How a year of virtual living made me appreciate people more

When I tell people I’m an introvert, reactions split into two camps. For those who know me well, it’s pretty much, “Yeah, duh.” But for those who have only been exposed to me in public settings, or online, there’s usually more surprise that a venture capitalist like me could be an introvert. People sometimes mistake introversion for shyness or lack of confidence. But it’s really about whether being with people gives you energy or takes energy away. I love people, I just need adequate amounts of time to recharge, usually spent by myself.

If you’re reading this I’ll assume you’re human, which means the past 12 months were probably pretty tumultuous for you. My family has been incredibly fortunate and hopefully, the long-term consequences are going to be minimal. Lately, I’ve found myself mostly trying to figure out what lessons my daughter should learn from this time, and what lessons we specifically don’t want her to carry throughout her life.

This has given me a chance to redefine my own habits as an introvert — especially those related to how, where, and when I spend time with people.

When it comes to my job, after practicing venture capital for seven years under normal circumstances, it was instructive to get thrown into this new scenario, because I don’t think we’ll ever fully “return to normal.” Instead, we’ll blend aspects of pre-2020 and our experiences from the past year into a “new normal.” This has given me a chance to redefine my own habits as an introvert — especially those related to how, where, and when I spend time with people. It’s a work-in-process but here’s what I’m thinking:

Group events

In the past, these would always trip me up. I would experience some social anxiety mixed with generally feeling overwhelmed by my own internal scorecarding and thoughts of, “Am I networking enough?” Now on Zoom, I can just fall back to audio-only, or drop off the gathering when I’m ready to leave. (What’s the “turn off video” equivalent for me when being at a large event? Probably peeling away with a person or two for the ol’ walk and talk.) Going forward, I think virtual events will continue to evolve beyond the Zoom room and into formats like Icebreaker. I can’t say that Covid-19 has made me rethink the personal utility of the really big conferences (I don’t attend many), but it does make me miss the curation of smaller groups. The events where hosts put effort into bringing together people with a high degree of purpose and work hard to ensure mixing, those are wonderful. My 2022 will hopefully include a return to events like these.

Working with founders

This is what I really have missed. You might think I’m referring to the time spent with a founder before deciding to make an investment in their startup, and certainly, there are moments where an in-person conversation can be the difference between Deal or No Deal. But I don’t think we’ll ever go back to 100% in-person pitching, especially in the earliest stages of getting to know someone. It’s just too mutually efficient to make a first pitch into a call or video, especially if the founders prefer it.

What I really do miss are the post-investment moments that are so much better in-person — the types of relationships that get built over meals, over walks, and on a whiteboard.

But what I really do miss are the post-investment moments that are so much better in-person — the types of relationships that get built over meals, over walks, and on a whiteboard. Not the perfunctory showing up in person for a board meeting (although sometimes being there is important), but rather the stuff which requires as much EQ (or emotional intelligence) as IQ. And I’m anticipating doing a lot of this in the places our portfolio companies are scattered: the Bay Area, New York City, Los Angeles, Atlanta, Toronto, Portland, San Diego, Boston, Salt Lake City, Mexico City, Buenos Aires, and so on.

For what it’s worth, I sense lots of startup teams are ready to get back into offices as well or at least have the flexibility to work in-person for the periods where collaboration and culture-building are most essential. If I were early in my career, it would absolutely be my preference to work for a company with an in-office culture (either full-time or hybrid). There’s just so much community and learning-by-osmosis (or serendipity) that comes from being together. So while our VC firm Homebrew definitely invests in companies that are 100% remote/distributed, we also espouse being intentional about what it means to do so and not underinvest in the infrastructure, travel, and skill-building it takes to succeed in this model.

Work-life balance

Do we still call it this? How about just happiness and sanity? I’ve found that I really enjoy driving my kid to school on Friday mornings. I’ve found that playing backgammon with my wife over lunch is nice when our mutual schedules accommodate. I’ve grown increasingly fond of just talking on the phone with a founder for five minutes when they need some help (versus going back and forth over email). Optimizing as best I can for flexibility has been a delight and a privilege, one I hope to maintain. My weekdays are basically 80% Homebrew, 20% family, with my weekends being the reverse. So far it’s worked out pretty well, except I think my dog is going to be shocked when we’re not in the house with her 24/7.

Optimizing as best I can for flexibility has been a delight and a privilege, one I hope to maintain.

Homebrew closed its office in San Francisco’s SOMA neighborhood last March, and we’ve only been in there a handful of times since. Our lease runs until spring 2022, and I have no idea if we’ll renew it or not. It’s a great space that accommodates our five-person team quite comfortably with flex-desk room for another four to six people. My best guess is that we’ll retain the office — or something like it — but hopefully, see the benefits of a city in transition realized in slightly lower rents. Or maybe not. Perhaps San Francisco rents are positively correlated with VC’s internal rate of return!

I do miss being near my business partner Satya. During the social distancing era, we’ve found ways to safely get together but, to be honest, it’s not frequent enough for me to be optimally happy. Years ago, before we started the firm, my wife and I casually looked at buying a house two doors down from his. Maybe if we’d pulled the trigger I could have had a true Homebrew pod! (Although I’m not sure what the rest of our families would say about this?)

There’s still a lot to figure out over the next few months, but here’s to vaccinations! I hope you all get through the next few months healthy, supported, and thriving.

Why Facebook’s Responsible A.I. Team Needs to Be Able to Lose Money in Order to Do Its Job

‘Oh, your algorithm update lowers revenue and decreases usage? Ship it!’

Photo: Solen Feyissa/Unsplash
 

“Measure what matters and what you measure matters.” There are any number of similar quotations that talk about how the very act of tracking a KPI in an organization causes people to focus on it more, let alone if you’re linking an explicit incentive structure to goals. It’s why, for example, if boards care about ideals like diversity and culture, they should work with CEOs to make sure those stats are first-class citizens on the company dashboards alongside revenue and profit.

It’s even harder when you can’t agree what the right metric should be. As I’ve written before, one of the problems we face as an industry is largely trying to measure current day Web 3.0 with Web 2.0 dashboards. Misinformation, trolling, harassment, polarization, and the resulting negative implications — none of these are as simple to define as CTR or CPM. I myself fell victim to this during my time leading the consumer product team at YouTube. When Google leadership asked us to shift from focusing solely on user growth to also increasing monetization, the team we destaffed to fund the new effort had been working on the comments system. Yup, YouTube comments, which most often resulted in a lot of name-calling, profanity, and worse. We all wanted it to improve, but why did I sacrifice this project in the near term? Because it wasn’t connected to a first-tier KPI, like revenue, uploads, or playbacks. So it had to wait.

But what if you have the right metric to measure—say, the negative externalities of a product—but it turns out that number is loosely negatively correlated with your business KPIs? Like, for example, if polarizing content leads to more short-term engagement, which leads to more active users, which leads to more ad revenue? It’s not crazy to wonder this, and while I don’t believe that it’s a true correlation or that our social platforms are intentionally running at the efficient frontier of anger and profits, I do always wonder what margin pressure does to, say, adequate investment in trust and safety.

Casey Newton’s Platformer article about Facebook’s Responsible A.I. team provoked a combination of eagerness and skepticism. My fear is that even if these teams are actually equipped to study and challenge internally held beliefs about their products, they will be forbidden from making changes that negatively impact business metrics. That is to say, we want responsibility but only when it doesn’t put the stock price at risk. I say this not just (or specifically) about Facebook, but more generally about the complexity of incentives within a corporation. Also, yes, it’s true that companies already make decisions to balance user experience with monetization. During my time at Google and YouTube, there were plenty of experiments with ad load, placement, and so on, and the company never maximized immediate dollars if there was a disproportionate negative impact on, say, user engagement or advertiser ROI. Long-term greedy, I guess, not short term.

But back to this question of how to give a team like Responsible A.I. the ability to decrease dollars, engagement, or growth if they believe it has a positive impact on fairness, responsibility, or whatever other metrics they’re responsible for managing. I’ve got an idea: a budget.


 Yes, a budget! Teams like this should be entrusted to “spend” money up to an annual prespecified amount. It doesn’t mean they have to spend it. Indeed, many gains might be, in this example, revenue neutral or even revenue positive. But let them make decisions consistent with their mandate without having to implicitly (or explicitly) defend why they’re causing the company to leave dollars on the table.

Look, I know this is a weird concept and has all sorts of potential secondary effects: Other changes are made elsewhere in the company to recover the “lost” revenue that turn out to have a different set of negative externalities. It reinforces the idea that fairness comes at the expense of revenue, perhaps giving other teams the ability to give up their “responsibility” and just let this separate A.I. team “fix” everything. Maybe we’ll get to a point where it’s more like carbon offsets, where each product team has to manage their own responsibility budget, and there’s an internal market to trade responsibility points. New challenges require new solutions, and in these cases, I think you’ll need to navigate corporate anthropology, not just corporate algorithms.

Turntable.fm Reminds Me How Much Fun the Web Can Be

What happens when your favorite dead product rises again

Turntable 2021, pretty much the same product (for now).

Usually the first email I open in the morning doesn’t make me scream out “HOLY SHIT!” But “Hey! I plugged in the Turntable servers” will do that to you. It was Billy Chasen, Turntable’s OG founder and CEO, and the email included a password, which I immediately mashed into my web browser. You see, Turntable.fm was the Clubhouse of a decade ago: a bunch of social features that nailed the serendipity of being together in a novel manner while breathing life into a familiar format.

Music, as it became digital, also became lonely. The trade-off in having all the world’s recorded tunes up in the cloud was that a communal experience transformed into a solitary one. Single-player mode. Not because of consumer preferences but because of DRM, label negotiations, and dollars. Turntable immediately brought back the listening party. And it was super fun.

It was spring 2011 and the links started getting passed around. Join me here, now—a late Friday night with just some nerds spinning old-school hip-hop songs from our teenage years. Then some more people. And some more people. And some more people. And before you know it, Union Square Ventures is leading a round and I’m an angel investor in my favorite new product.

Music, as it became digital, also became lonely.

It didn’t work as a business. Labels were not ready to engage in a collaborative discussion. The team was not always rowing in the same direction together. And Turntable eventually went dark. Billy and I stayed lightly in touch as he, and I, grew older and saw and did more things. He has always been able to see around corners and turn human needs/interaction models into products. Sometimes just a bit early. But like with most fun projects, the relationships outlast the startup. (To that point, fun side story: Turntable was also how I met Sahil. He was this young kid who had just built Pinterest’s mobile app and there was an all-out effort to get him to join Turntable. Sacca sold him hard. So did I. He turned us all down because he wanted to do his own thing, which turned out to be Gumroad. Small world.)

Periodically there’d be a Twitter thread about Turntable nostalgia and we’d all reminisce about products long gone that haven’t been adequately replaced (Google Reader, RIP). Someone would chime in with a link to some collaborative playlist tool but that was never the magic of Turntable.

So now I’m hanging out in the iconic I ❤️ the ’80s room, just like back then. It feels comfortable, warm, lived in. The way a good consumer product can. Some startups struggle to find product market fit; Turntable had it, went dark for nearly a decade, and then just turns itself back on with the same PMF. Wow.

What now? Will Turntable become a “company” again? Is it just a joyous few weeks before the server bills become too expensive, or the code too janky? I don’t know and that’s part of the fun. Because right now it’s 2011 baby, and I’m waiting for a DJ spot to open. Gotta get my monkey avi back…

The Baddest Band In Town

In a pre-RATM band, guitarist Tom Morello was shamed by a musician friend about how his guitar strings ran long off the head of the instrument (a now iconic look for him).

“‘Cut your strings! What, you think you’re the baddest band in town?’

And I was like, I’m definitely not the baddest band in town so I cut my strings.

Years later, in Rage Against The Machine, I was in the baddest band in town and so I let my strings go”

A Year of Zoom Genitals, Bourbon Bottles & Child-Rearing

Five Memorable URLs from COVID Season One (aka the last 12 months)

March 11th was “COVID Day One” for many folks, or at least when it crossed from “will this be a big deal?” to “this is a big deal” for America. While much of Silicon Valley was already curtailing travel and starting to work from home, zeitgeist watchers note a perfect storm of the NBA suspending their season, Tom Hanks being diagnosed as positive, WHO declaring a global pandemic and He Which Shall Not Be Named implementing a travel ban (actually a good idea) as the starting point for “this isn’t just the flu.”

Reading Maya Kosoff’s ‘Lost Year’ essay as part of Medium’s Pandemic Reflections made me consider my own past 12 months. Because of my love for this thing we call the World Wide Web, I’m going to do my own reminiscing via Five Links.

The COVID Tracking Project

An oasis in a misinformation desert, the COVID Tracking Project started very ad hoc but was always authoritative and reliable in trying to understand the illness’ spread. Good data helped put so much in perspective: that this thing was running wild, that it was disproportionately impacting vulnerable communities and geographies and that outside of vaccines, the spread *could* be managed via safety practices.

As the numbers got larger and we almost numbed to the milestones, I stopped focusing on the quantitative and transitioned to the qualitative, namely how to emotionally support my family and my community. The COVID Tracking Project will discontinue updating on its first anniversary (March 7, 2021) but it was one of the URLs that defined my first year of COVID.

When Casey Newton & I Got Zoombombed

Early on this whole WFH thing was kinda silly and fun in the tech industry. People were adjusting to a life of video conferencing (remember when dogs and babies jumping into the frame was novel!), and along with my friend Casey, there were two weeks we ran 5pm Zoom Happy Hours with guests and fun and surprises.

One memorable happy hour involved a Zoombombing where, because we’d left the event link public, some troll took control of the screen and started showing really graphic porn videos. Subsequently Zoom ended up changing a bunch of meeting defaults to prevent this sort of misbehavior and I turned down all the news requests to come speak about our experience. My mantra is “control your first page of Google results” and I wasn’t sure I wanted my above-the-fold vanity search to produce evergreen dick pics.

Now a year later, it’s clear why virtual event platforms, gathering spaces like Clubhouse and other social apps have boomed. We’re primates and we need to be together!

Raising a Kid During COVID

This is my own post from last April, about what lessons do I want my daughter to learn from this last year vs what do I not want her to overlearn. We’ve been so fortunate to have resources and be in a personal situation that supports the flexibility to work from home relatively easily. And while I know this has protected our family from certain hardships, I don’t pretend that it’s an impervious shield against socio-emotional distress. When a quarter of her school-age existence has been spent in lockdown it would be nuts to assume there’s no impact. So we focus on resilience, and expressing our feelings, and being kind to each other. And being very excited for when she can act upon the desire to see and hug her friends without flinching and stopping herself.

The K-Shaped Recovery

“The stock market is not the economy.” I heard this a lot in 2020 when trying to reconcile the overall growth in the public markets, and hypergrowth in tech, compared to the pandemic reality for so many Americans. I got to say things like “I’ve never ordered so much Goldbelly!” while others lost paychecks and family members. My friend Nikhil summarized so many of my thoughts in his essay A Widening Gap.

A widening gap. A gap between the “haves” and the “have nots,” between those with disposable income and those that don’t have jobs. A gap between fact and fiction, between those that have access to the truth and those that are fed lies non-stop. A gap that’s been exacerbated by the pandemic, certainly, but also by the forces of technology, media, and politics, not just in the last four years, but for the past decade.

It will take considerable work, across technology, media, and government, to reverse this course. There isn’t a simple solution that will be the next big thing in 2021; instead, it’s going to take years of effort.

What I appreciate about Nikhil’s blog post was that it’s not just about tech’ing our way out of this dynamic, but about empathy, caring and even some sacrifice. “Do Things That Don’t Scale” is classic startup advice and I feel the same way about the beginnings of what it takes to reverse these inequality dynamics. Beyond structural change, if we each just cared for a handful of other people in a way that extended beyond our immediate circles, we’d make so much progress. It’s why I love direct action nonprofits such as Human Utility.

My Virtual Drinking Buddies

For years when people asked what my hobbies were I’d kind of shrug my shoulders. There were activities I enjoyed (movies! friends! work!) but nothing that I’d consider a ‘hobby.’ Maybe I’d been overly influenced by the people around me who, when they pursued something, did so with a focus that turned “jogging” into “complete marathons on all continents” and “cooking” into “I’m spending the summer in France as an apprentice pastry baker.” If a hobby equated to something you spent too much time and money on, then my only hobby was therapy!

But I’d gotten tired of not having an answer and started telling folks my hobbies were coffee and notebooks (the paper note-taking kind). These were honest answers as I do enjoy researching, purchasing and consuming both of these, but there’s only so far you can go with notebooks and on the coffee front, I cared more about good beans than necessarily experimenting with every prep method, which meant the subreddits were a bit too much for me.

Fast-forward to the beginning of 2020 and the whiplash we all experienced with travel stopping, restaurants closing and our homes becoming work, play, live 24/7. We’ve all adopted new coping mechanisms and found new aspects to our relationships. Some even used the time to reconsider where they work or move to new cities. Me? I got into whiskey.

Before sharing more I want to acknowledge that alcohol as a “hobby” can be jarring for many. People close to me have dealt with various addictions, including alcohol, and many more have removed it from their lifestyle in the interest of health, mental clarity and other benefits. Fortunately I’m not prone to over-consumption and my interest has been as much about the history, business and people around the spirit as actual consumption (I’m basically a 1–4 oz type of guy — for reference, the average 750ml bottle is roughly 25 ounces).

I’d previously been whiskey-curious, buying a bottle every now and then, trying different bourbons in a bar and so on. But about a year ago I joined a local Bay Area whiskey group that I’ve enjoyed learning from, sharing with and doing virtual tastings. It’s fun to have a space that’s not about tech, not about politics and just about guys and gals with a passion. Thanks also to Caroline and my daughter for giving up some shelf space in the basement for my “hobby.”

Ok, so those are five links that have been important to me through the first 12 months of COVID. Here’s hoping all the graphs continue to head in the right directions and we’re able to help and celebrate one another in-person soon!

Notes and More

The first two months of 2021 are gone! I’ve tried to be very intentional, greeting my family and friends with statements like “welcome to the third Thursday of February” (or similar). 2020 was such a weird blur of speed and slowness that I’m trying this year to be more aware. Probably as a coping tactic!

📦 Things I’m Enjoying

Etta + Billie soapsSmartSweets Sugar Free Gummy Bears. Taylor Swift’s re-recordings.

🏗 Highlighted Homebrew Portfolio Jobs

Plaid is a developer-first company making it easy for financial data to move between apps. They’re hiring in a variety of roles across US, Canada, Europe and Remote.

Why There’s No Such Thing as a ‘Startup Within a Big Company’

You will never be able to take the brand risks, the legal risks, or the partnerships risks that a true startup can

Noam Bardin of Waze. Photo: Nicholas Hunt/Getty Images

I’d exchanged DMs with Waze co-founder and CEO Noam Bardin a few weeks back to ask about learnings from his last few years inside Google. Waze is the $1 billion-plus acquisition that people, well, forgot about despite its size and growth. I mean, in all the “Big Tech” regulations discussions we regularly hear about Facebook/WhatsApp/Instagram and Google/YouTube, but Waze just kind of flies under the radar. Bardin replied that he was leaving Google at the end of January and would do some sharing after. Boy, understatement.

Today, Bardin published a personal essay titled “Why did I leave Google or, why did I stay so long?” and it’s a really telling, thoughtful, honest post. You should read it all but let me share a specific paragraph here:

I took the acquisition as a personal challenge. I believed that I could build out Waze within Google, breaking the myth about what happens to companies after being acquired by large corporations. Looking back, this reminds me of the Western CEO and China. Every Western CEO thinks she or he will be the first to be a successful Western brand in China and many try and launch a service there. The Chinese are used to this Western arrogance and welcome the foreigners. Many quarters and dollars later, the Western CEO leaves with some China experience and the Chinese partner keeps the IP, money, business… You cannot fight the nature of the beast, this is China. Same thing happened to me in China pre acquisition… So, to complete the analogy, I was the naive startup leader believing that I can build out Waze within Google to its full potential and conquer the beast, regardless of its nature. This irrational belief is critical for a startup leader but challenging in the corporate environment.

There is no such thing as a startup inside a big company. There’s various leash lengths to your freedom, but you’re no longer a startup. You get a bunch of things in return and, for many people, it can be a wonderful outcome, but you’re no longer a startup. I love that Bardin took this challenge and stayed well beyond when he needed to in order to set up a management team who could carry the product forward, as a business unit.

I got to see the YouTube acquisition firsthand and I think, for at least the first few years, we were the best version of “independent” you could ask for. Two people are primarily responsible for this: Chad Hurley and Eric Schmidt. Hurley, and his co-founder Steven Chen, had gone through the PayPal/eBay merger so they were the proverbial “wise beyond their years” when it came to what being bought meant and all the trade-offs that came with it. Schmidt had promised a high degree of autonomy and kept his word. We did deals with Apple, Facebook, and Twitter. We hired people directly into YouTube. We made acquisitions. I even got to route around some of the stuff Bardin pointed out as being especially frustrating with regards to PeopleOps (firing folks, optimizing bonuses for high performers).

When Tumblr was acquired by Yahoo in 2013, I shared some of my advice with the team, first publicly in a blog post and then in a private conversation with some Yahoo folks who read the post and reached out. We all know what happened there and I’m glad Tumblr is now with Automattic.

This stuff all works in reverse, too: When someone tells you that there’s an opportunity to “build a startup within a big company,” don’t believe them. It’s just not true. You can work on experimental products in a mechanism that tries to counterbalance some of the gravitational pull and processes that a big company otherwise uses to manage itself, but it’s not a startup. You will never be able to take the brand risks, the legal risks, or the partnerships risks that a startup can. To paraphrase someone I know who tried to lead one of these projects at Google (and had done an actual startup themselves): It can never be like a startup so long as my team has the Google badge on their belt and walks into the fancy cafeteria every day.

This wasn’t a comment about co-location; it was a comment about the working style, the expectations, the flying without a net, that high performing startups require and the people they attract. It’s not that those Googlers were “better” or “worse” than startup hires, but just that startups are completely different.

You can find experimental groups within larger companies — Area 120 at Google and NPE at Facebook — but they’re not startups.

If you want to be at a startup, join a startup. As Bardin says, “I am confident that the Waze acquisition was a success. The problem was me — believing I can keep the startup magic within a corporation, in spite of all the evidence showing the opposite.”

Three Types Of Startup Advisors You Might Not Have Thought About (But Will Help You Win)

Advisors can be so much more than social proof and tactical advice

“Can we put you as an advisor in our deck? You don’t even need to do anything and we’ll give you equity. It would be a big help for our fundraise.” This was the proposition offered to me surprisingly frequently during my pre-Homebrew days. You see, the demand for “startup advisors” were going through a little bit of a boomlet.

AngelList had just started and their company profile page had a bunch of “Advisor” slots to populate that were displayed in the same visual design as investors and team members. This subtly started to create social proof pressure to fill out those available spaces in the most impressive way possible. Never underestimate the power of defaults!

Anyhow, fast-forward to 2021 and it almost feels like startup advisor roles have fallen a bit out of fashion as everyone scrambles to be an angel investor, a scout or solo capitalist. Many of the people who previously might not have had access to capital are now able to invest their own dollars, or someone else’s, and this has much greater social proof for both the company and the individual. Most of the companies we back figure out how to use advisors in compelling ways, it’s just not as public as it used to be.

That said, there are three types of advisors that I don’t see as commonly utilized by early stage startups — at least the ones we’re not advising 😉

The “I’m Going To Recruit You Down the Road” Advisor

Great founders are always recruiting. Often for open roles but also playing the long game, building relationships with passive senior candidates who either aren’t ready to leave their current job, or are more interested in the opportunity once you’re a bit further along. Rather than just making a note to ‘grab coffee’ every once in a while, I suggest looking to bring them on as advisors. It doesn’t have to be a huge commitment on their part (or significant equity), but just start giving them some tie to your startup and some incentive to maintain the relationship. Obviously this won’t work if they’re current employed at a competitor but otherwise it’s a half-step in the right direction. Mutual try-before-you-buy and gives them a chance to better understand the company.

The “Set Up My Functional Leads for Success” Advisor

I’m a big proponent of startups hiring talented high-ceiling people who are earlier in their careers and haven’t necessarily yet done the job they’re being recruited for. For example, if you meet someone who has been a PMM at Google for a few years on a high performing team and is itching to get into a role that allows her to spread her wings more, grab her. Don’t worry that she hasn’t had a senior title or whatever. Just get her on board and set her up for success. And one way to help her is to make sure she has a mentor. Not just inside of the company but outside.

Ask her if there’s someone senior in her career that’s been a great manager, and if so, bring them on as an equity-compensated advisor to your company. Don’t make it her job to convince them to support her ongoing, give them some skin in the game. You’ll be setting the new hire up for success and this should pay off in multiples. I’ve also found that during recruiting process telling a candidate like this that they’ll get an ‘advisor equity budget’ to bring people closer to the company who can be useful is a signal of trust and agency that helps close them.

The “Customer Council” Advisor

This works especially well when you’re selling into a non-tech industry because getting a bit of equity in a startup is even more novel and exciting. A sales and marketing tactic as much (or even more) than a customer development one, try setting up a Customer Council Advisory Board. For relatively small amounts of equity you can create a group of 3–12 folks from your industry who feel a mutual obligation to help make you successful. It’s a great group to use for networking, press quotes, product feedback and such. Of course avoid direct conflict of interests — i.e. these people can’t be your current buyers (most of the time) but they can certainly be from customer organizations (their own policies permitting) and from larger customers that you’ll be targeting a few years down the road.

So hopefully you can make use of advisors in new and interesting ways! Remember, the standard agreements are two years in length, have a 3–6 month vesting cliff (with monthly thereafter) and preserve right of either party to terminate. Have you had success using advisors in a nontraditional manner? Let me know!

Notes and More

Give everyone the vaccine! Try and prioritize the vulnerable first of course, but let’s focus on speed of rollout too. Everyone who gets vaccinated makes it safer for everyone else.

📦 Things I’m Enjoying

Etta + Billie soapsSmartSweets Sugar Free Gummy BearsThis essay about the widening economic gap between tech and most everything else.

🏗 Highlighted Homebrew Portfolio Jobs

Plaid is a developer-first company making it easy for financial data to move between apps. They’re hiring in a variety of roles across US, Canada, Europe and Remote.

This Is The Single Most Important Page On The Web (If You’re a Human)

Cognitive Biases Shape Us Beautifully And Tragically

If you could only access a single URL on the web what would it be? Not something like Google or YouTube but actually a single static url — so youtube.com/[some specific video]. I was thinking about this earlier today and my initial framing was “what page is performs the most complex task that I couldn’t do myself,” imagining that optimizing for absolute computing power would be the right angle. It took me a minute or two but I realized this was completely backwards and that I should be trying to figure out what content would be most impactful upon a different type of computing power, namely my own brain.

That flip led me back to a page that I absolutely love, and try to visit quarterly or so, when I want to laugh at myself: Wikipedia’s List of Cognitive Biases.

Example from the Cognitive Biases Page

“A cognitive bias is a systematic error in thinking that occurs when people are processing and interpreting information in the world around them and affects the decisions and judgments that they make.” — VeryWellMind

Reviewing this list periodically (as well as reading Robert Cialdini’s Influence, one of my favorite books) always makes me slap my forehead at the ways we are beautifully and stupidly human. Anchoring Bias? Guilty (maybe this very post is an example!). Survivorship Bias? Twice last week that I can remember. And it goes on like that.

Then I shift to wondering about the role of technology in helping us with these biases, and two different paths to doing so. The first is essentially giving up more of our agency and outsourcing an increasing number of our decisions to AI. The second is some sort of listening device (our phone, our watch, our nerd AR glasses) that notices when we’re saying something that fits a cognitive bias and sends an alert to help us reconsider. Frankly *both* are a little freaky to me, but is it really any weirder than me frequently re-reading this Wikipedia list and trying to manually break myself of these biases?

I’m sure we all have a personal redline about things we’d automate and things we wouldn’t. Maybe we like the idea of control over the ‘last mile’ — for example, happy to let a dating app give us top 10 profiles they think matches for us, but we’d prefer to pick the ones we want to connect with versus the same app setting us up with one of the 10. I wonder if these ‘redlines’ are generational (ie younger folks trust the computer more or less than I do), cultural, demographic or more fixed. At the end of the day, we’re all the sum of our cognitive biases.

Notes and More

It’s inspiring to see vaccinations starting to roll out but part of me wonders whether the prioritization framework is actually slowing us down. Whether ‘risk group’ should be accompanied by goals for absolute number of shots given and fastest path to herd immunity. I’m not advocating for myself — I’d gladly be in the last cohort of shots if we could get there as quickly as possible.

📦 Things I’m Enjoying

Finished HBO’s Watchmen, which was great. What should I watch next? Goldbelly is totally my social distancing MVP — we order BBQ from a different place every few weeks. These are the KN95 masks I’ve been using, although there’s now thankfully a bunch of different ones in stock. Mask up!

🏗 Highlighted Homebrew Portfolio Jobs

Tia is healthcare designed for women from the start, combining IRL clinics with URL telehealth. They’re a well-funded post-Series A startup that’s growing quickly to meet the needs of their clients. If you’d like to join the Tia team and build the future of care, they’re hiring.

Don’t Just Stand With Someone Being Harassed. Stand In Front Of Them.

Lessons on Allyship and Community

✅ IRL Friend. That’s the tweet I employ to signify that I’ve finally met up with someone previously only known to me online. Of course 2020 hasn’t had much of that interaction but I know that when we’re all hugging it out again, Danilo Campos is one of the peeps I’m looking forward to seeking out.

Danilo combines calling me out on my bullshit with a recognition that intent matters; we’re all learning; and the willingness to throw more than 280 characters towards our conversations. One such back and forth occurred on the day after the domestic terrorist attack on the US Capital. Much of the timeline was outraged and narrative was we all stand together. For Danilo that wasn’t the whole story.

I know when I see my DM indicator light up in the middle of a Twitter thread that something requires a backchannel. And this one came from him. And it came with links.

It shared a story that I was lightly familiar with but lost track of after its initial coverage. On Long Island, the region where I grew up, a Black woman homeowner, new to the neighborhood, started getting harassed in disgusting ways. Her reports to police went ignored and the threats became more severe. Authorities starting paying attention once the story went viral of course, but why did it take that sort of pressure?

Danilo also shared a DESUS & MERO clip where the homeowner told her story, including one young man who rose to the occasion. He came over each night and started watching her house, Periscoping the whole thing in case anything happened to her or him. The idea was, I’m here for you and willing to put myself at harm to prevent yours.

My takeaway was, sometimes you need to stand behind someone. Sometimes need to stand with them. And sometimes you need to stand in front of them. They’re all forms of help, but those of us who are most able and privileged can practice the “standing in front” more often (with permission and grace) if we’re going to be really friends.

I Just Got Paid For Work I Did 20 Years Ago.

Startups Should Work To Make Their Employees Wealthy Not Just Their Founders And Investors

Earlier this week a modest deposit appeared in my checking account, one I honestly never expected. You see, it was for work I’d performed from 2001–2003 at a startup called Linden Lab, the company behind virtual world Second Life. And when that company was acquired in late 2020 by another private party, my stock purchased in 2004 turned into cash. The transaction size was small compared to the IPO and SPAC headlines from the past few months, but I had the benefit of being an early, single digit employee, and hence a stock value of around .04/share if I’m recalling correctly. That low price was part of what enabled me to purchase my vested options when I left, a conundrum that exiting employees often face.

Thinking about this outcome, and jumping into a Linden Lab alumni Zoom over the weekend, swirled a bunch of feelings. So much has changed since those years trying to build an online community with a small group of people in Hayes Valley. I subsequently joined a larger startup that got really big and then cofounded a venture firm with a close friend/former colleague. I tried to outrun failure only to realize I need to embrace it. And I achieved ‘Silicon Valley Middle Class’ wealth status.

But the real takeaway was that if you want to work at tech startups and can find one you’re excited about that is both (i) A+ people and (ii) treats you fairly with regards to compensation, including equity, take the job. Don’t overthink it. This is also where I acknowledge we’re talking about being privileged enough to take a job with a startup in the first place, to have even a small amount of savings to risk on the equity and the structural issues which prevent many people from realizing these outcomes. Consider that an asterisk as you read forward and commit to creating opportunities for others, not just yourself.

While I’ve said before that one should approach these situations with eyes wide open [“Sorry Startup Employee #100, Your Equity Probably Won’t Make You Rich”] I also firmly believe ownership is the key to wealth. A career in technology is a very good path to financial stability and stock equity has been a meaningful contributor to that for me and many others. It’s always why, in my venture role, I get so excited when I see an outcome large enough to benefit an entire team, not just the executives and investors. It’s also why I support making early exercise available to your seed/A employees at the very least. And extending exercise windows for longer than 60 days to employees who leave on good terms. And why we work with the founders we back to make sure there’s enough equity set aside to make great hires.

FWIW, we also back up this belief with actions ourselves. Everyone on the Homebrew team receives carry in the fund. What that means is that in addition to salary and bonuses, when Satya and I get profits back from the fund, so do they. You can’t preach ownership mentality outside your firm and do something different internally.

Notes and More

📦 Things I’m Enjoying

Here’s my annual recommendation for the easiest way to make hard-boiled/poached eggs. And I just started Watchmen on HBO — no spoilers please!

🏗 Highlighted Homebrew Portfolio Jobs

Tia is healthcare designed for women from the start, combining IRL clinics with URL telehealth. They’re a well-funded post-Series A startup that’s growing quickly to meet the needs of their clients. If you’d like to join the Tia team and build the future of care, they’re hiring.