Things I Learned From a New Yorker Article and How I Got Over My Own Insecurity

Good writers aren’t just skilled in their prose, they have a nose for interesting topics. “Why Everyone Feels Like They’re Faking It,” an article about imposter syndrome in a recent issue of the New Yorker, is an example of a GREAT subject. The type of read where you pause between sections to chew on what you just finished.

The Imposter Phenomenon, as the original researchers called it (the fact it’s mutated to a ‘syndrome’ is part of its questionable evolution and ubiquity), has been coming up in my communities, mostly as a result of the tech economy struggles. The belief that perhaps you weren’t good at your job, it was just the markets going up, or, even more insidious, that you were never good at your job so now that a bull market isn’t masking that fact you’re about to be found out, are two oft-repeated confessions.

Regardless of how it’s being felt, I have my own empathy for people dealing with these internal snickers of doubt. For a long time my version of imposterdom was fueled by “I think I belong in this room but just barely, so I need to hold on tightly and/or constantly prove it, less I get kicked out.” As a result it was more difficult to be pleased by individual or team success, which only served as a reminder that the next race was beginning. And in hindsight, the perilous nature of my own perch probably made it more difficult for me to see conflict as a ‘fight or flight’ challenge, rather than an opportunity to build connection and shared understanding.

Thankfully, besides just getting old, I created hacks to retrain my defaults. They’re more fully detailed in this previous blog post (“How I Calmed My Imposter Syndrome with These Two Tricks”) but in summary:

What Would 18 Year Old Hunter Think About Where You Are?

Are You So Good That You’re Fooling All These People?

So back to that New Yorker article. First off, the research dates back to two women [Pauline Clance, Suzanne Imes — Oberlin College colleagues] in the 1970s who brought their own personal expereinces together, and then expanded to a broader conversation

The pair spent five years talking to more than a hundred and fifty “successful” women: students and faculty members at several universities; professionals in fields including law, nursing, and social work. Then they recorded their findings in a paper, “The Impostor Phenomenon in High Achieving Women: Dynamics and Therapeutic Intervention.” They wrote that women in their sample were particularly prone to “an internal experience of intellectual phoniness,” living in perpetual fear that “some significant person will discover that they are indeed intellectual impostors.”

Once their study was published in 1978 it set off a rolling thunder-like spread. Particularly charming was this reminder of how things went ‘viral’ before the Internet.

The paper spread like an underground zine. People kept writing to Clance to ask for copies, and she sent out so many that the person working the copy machine in her department asked, “What are you doing with all these?”

Then, nearly 50 years later, two other women coalesced around the idea that Imposter Phemoneom was capitalist gaslighting and a form a priviledge that focused on convincing yourself you belonged to the structure versus interrogating the very real barriers.

In “Stop Telling Women They Have Imposter Syndrome,” published in the Harvard Business Review, in February, 2021, Ruchika Tulshyan and Jodi-Ann Burey argue that the label implies that women are suffering from a crisis of self-confidence and fails to recognize the real obstacles facing professional women, especially women of color — essentially, that it reframes systemic inequality as an individual pathology. As they put it, “Imposter syndrome directs our view toward fixing women at work instead of fixing the places where women work.”

You should read the article, especially because it weaves the lived experiences of these four women together.

And remember how at the beginning I mentioned that a good writer chooses good subjects? Well this author, Leslie Jamison, also did one of my favorite 2022 New Yorker articles about the Choose Your Own Adventure series of books. Leslie has a nose for bangers!

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It’s Very Likely That Artificial Intelligence Will Be Worth More In Aggregate Than is Currently Being Invested (Just Unevenly Distributed)

In kindergarten my daughter learned to not ‘yuck’ someone’s ‘yum.’ That is, just because you don’t like something there’s no reason to share that in the moment with another person enjoying it. There’s a lot of yumming AI right now and it’s of course perfectly fine (often helpful!) to challenge this excitement on technical grounds. Or ask questions about responsibility and legality. Or question business models. But to respond to the current state of affairs but just shouting “BUBBLE” isn’t just valueless Yucking, it’s likely incorrect.

During the Installation Phase of a new technology (HT Carlota Perez) there’s a bubble phase that coincides with the frenzy ahead of deployment. It’s when it feels like the New Thing has limitless upside, that “anything is possible and everything before will be disrupted” mindset. This is largely a feature, not a bug, of our industry (and of venture investing). The challenge of course is to not blindly anoint any fad as the New Thing, and to defensively protect the New Thing from any criticism. Both of those lead to fake or inbred New Things.

But from an economic point of view, let’s better understand what a ‘bubble’ actually means, because it’s often expanded and abused beyond the classic definition.

Bubble, in an economic context, generally refers to a situation where the price for something — an individual stock, a financial asset, or even an entire sector, market, or asset class — exceeds its fundamental value by a large margin. — Investopedia

So to suggest we’re in an AI Bubble is to say that the total enterprise value of AI that can/will be captured by private companies is less than the capital being invested into them right now. If you truly believe this, then yeah, shout Bubble from the rooftops, but I’d take the other side of this bet all day long.

Of course this doesn’t mean that all the value created will accrue evenly or the way investors expect it to. Quite clearly there will be ‘winners’ and ‘losers’ — maybe even some spectacular failures — but this doesn’t mean Bubble.

When a New Things cycle runs its course we end up with one of three realities:

I. Total Value Created < Total Investment Capital Deployed (Bubble 101. Perhaps scooters and other micro mobility startups of the last decade are an example of this?)

II. Total Value Created > Total Investment Capital Deployed *But* Highly Concentrated Winners (the last 15 years of ride share fit this bill? Can still feel like a Bubble even if not the classic definition)

III. Total Value Created >>>> Total Investment Capital Deployed & Multiple (But Not Necessarily Equal) Winners (this is the outcome of truly revolutionary and disruptive technologies. SaaS and Cloud perhaps?)

At a macro perspective, I currently believe this cycle of AI is much more likely to be II or III than I, with a bias towards the more distributed view of III (because I’m an optimist). But my thinking on where value will accrue is still formative and probably requires a separate blog post.

But it’s definitely not a Bubble 🙂

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An Economic Vehicle With a Societal Mandate, Screendoor Backs Emerging Managers from Underrepresented Groups

My hope for Screendoor is clear, if not simple: we’re going to be the largest, and most impactful, investor in emerging managers. Our strategy for accomplishing this is to focus on new firms led primarily by underrepresented VCs, back them meaningfully, and support them via a community of peers, advisors, and institutional LPs.

When 10 of us founded Screendoor in 2021 this was the plan. Almost two years later we’ve backed 11 managers with over $40 million of commitments, reviewed applications from 500+ funds, and, most recently hired our first Managing Director to help lead Screendoor into its future. Lisa Cawley joins us from the LP side of the table, already having experience evaluating and investing in emerging managers as well as a broad set of venture models. In her own words:

Screendoor’s role as an LP of GPs is the needed connection between underrepresented emerging managers and the institutional investment community, with our GP advisors who have ‘been there, done that’ recognizing what it takes to build a firm in the absence of a long track record. I’ve never had more conviction that investing in first-time funds led by underrepresented emerging managers isn’t just a societal impact initiative. In today’s vast venture capital landscape, it’s ALPHA!

It’s not enough to change team compositions with a few new hires or add supplemental pools of capital (all of which are still important and necessary efforts to continue). We need targeted action that accelerates the impact of these collective endeavors. I’m elated to now fully focus my time and effort to lead Screendoor to capture this incredible economic opportunity for our phenomenal LPs and the communities they serve, act as a source of catalytic capital and counsel to the next generation of leading fund managers across all backgrounds, and change the face(s) of venture capital!

We’re proud and thrilled that Lisa saw Screendoor as a platform at the intersection of incredible financial opportunity and industry evolution. The idea that these two goals are potentially incompatible is a relic of the past. We intend, with a coalition of the likeminded, to be the future. Onward!

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Second Life, Minecraft, Roblox Collectively Taught More People To Code Than America’s Top Universities Have

Almost all my Gen X peers had some lightbulb experience as a child with their first personal computer. Whether command line, or graphic design, or playing a game and wanting to know what made it work that way, the beige box transformed our lives. How fortunate to be born at a specific time and place and privilege!

Across generations there’s also a cohort who got pulled into technology by participatory virtual environments — from the earliest text-based environments to the successive user-editable immersion of Second Life, to Minecraft, and now Roblox. You don’t even have to squint too hard to see MySpace and Tumblr as 2D worlds, and the kids who designed background, templates and the like for those.

When I think about all this it’s not just nostalgia, it’s optimism. Software is the most powerful tool we have and while access is certainly not equal, it’s more available than the high walled professions that used to be drivers of social mobility. And so I still get wet eyed a bit when I hear stories of ‘coding changed my life,’ even more so when it happens to involved a product that I worked on personally.

Danilo Campos has a lovely post about his own ‘learn to code’ moment via Second Life (where I worked out of grad school). As builders we have choices in our products and Danilo talks about how the developer experience of Second Life was ultimately responsible for his career. The things he calls out, such as ‘co-created living documentation’ and ‘frictionless sharing’ should be aspirational in all of our designs. I’m going to quote some passages below, but you really should read the whole thing.

I have the career I do because eighteen years ago, by accident, I learned to code in Second Life.

What began for me as a series of experiments with scripted 3D assets evolved into my first business and my first software products. I made enough money selling content in Second Life to pay my real life rent, for months. With this experience in hand, I was prepared for the iPhone’s App Store indie developer revolution, which rocketed me to a career in Silicon Valley startups.

There’s immense gratitude I feel for this experience. I’m a first-generation knowledge worker. The leverage of a technology career isn’t something I grew up anticipating. I didn’t even think writing code was for “someone like me.” What a joy, to surprise oneself this way.

And after building some items to sell in Second Life

What a revelation this was, discovering firsthand that you could make money through the internet. My working class roots had nothing even remotely analogous.

I still remember the night my third robot launched. The money kept pouring in. Every few minutes, another notification would slide down, another jingling coins sound effect. While it was great to clear a month of rent in a weekend, what was even more exciting was more than 18 months of passive income. The robot sold steadily, until everyone who wanted a science fiction robot appearance had found and paid for it and the cash petered out.

Forever after, I would see the world differently.

And his hopes for the future (written Fall 2022)

As this technology cycle sputters to a close, a new one lurks around the next corner. I’ve always carried the hope that a new platform like Second Life could emerge.

Whether or not we find a worthy, broadly-adopted metaverse in our future, I think these lessons can help any developer tools project find some leverage for growth, positive impact, and creative power.

Thanks Danilo!

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Claire Hughes Johnson Joined Stripe in 2014 After a Decade at Google. Her Management Tips Are Legendary. Now They’re Published.

Imposter syndrome manifests itself in different ways. In my early career, it was primarily feeling that I *did* belong in the room (but just barely), and then trying to prove this to others around me. Eventually I relaxed a bit and got to just enjoy learning from my smart colleagues versus seeking approval. And what I found out was that some of them were really, really good at what they do. Claire Hughes Johnson belongs solidly in that cohort.

We overlapped at Google where she was a VP on the business side of the house but more notably she left the Plex in 2014 to join Stripe as COO when it was just a few years old. Claire got to experience, and played a large part in, Stripe’s proverbial rocketship, blossoming into thousands of employees, generating billions of dollars in revenue and valuation. While at the company — and especially once she departed — Claire became one of the people I always hoped to add to a cap table or startup board. There were just very few people who had the practical experience and framework-driven thinking she could bring.

But the truth is that human Claire can’t possibly scale to all the wonderful companies and teams that called on her. So instead she wrote a book, coming out March 7th, and available for pre-order now. Scaling People: Tactics for Management and Company Building promises to be one of the best reads in 2023.

Probably the best preview can be found in an interview she did with Elad Gil for his own book the High Growth Handbook (also a must have). For example:

On her viral ‘Working With Claire’ guide

I think that founders should write a guide to working with them. It would be one of the pieces I’m describing, to clarify the founder’s role: “What do I want to be involved in? When do I want to hear from you? What are my preferred communication modes? What makes me impatient? Don’t surprise me with X.” That’s super powerful. Because the problem is, people learn it in the moment, and by then it’s too late.

On decision-making, and consensus

When I’m leading through a tough decision, I try to say, at the outset, “I want all of your opinions, but I’m going to be the one who ultimately makes the decision.” Or in some cases, I will say, “I don’t know if I’m the right decision- maker. I need help exploring what the decision vectors are, and I need all of your help. And then I will let you know how we’re going to make the decision once we’ve talked about it.” If you don’t give people that guidance, which is I think a common mistake, you’re likely to run into trouble.

On the value of ‘founding documents’

Then the other thing you have is your operating principles or your values or whatever vocabulary you choose. You need to codify a set of principles and behaviors and then cohere to them, culturally. And those founding documents shouldn’t change very often. We refresh those operating principles every year, but they don’t change that meaningfully. I don’t think founding documents should change frequently.

I cannot wait for Claire’s book and predict it’ll become the next Radical Candor, Principles, Build, etc for the tech community. Congrats CHJ!

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What To Look For When Reference Checking Polarizing Entrepreneurs

There are certain words I don’t want to hear when doing backchannel references on a startup CEO. Sketchy would be one. Unmotivated another. Or those special little bombs of a phrase like “enjoys playing founder more than being one” and “tells a good story but no follow-through.” These come up — once is a warning, twice is a goodbye — and I’m not making the investment. But there’s another characteristic that on the surface could seem disqualifying but actually deserves analysis, and that’s “Difficult.” Are we talking abrasive, egotistical, read the Steve Jobs bio and thinks yelling was the key? Or the opinionated, driven, strong-willed, fast twitch muscle type? Because while the former might have big time Life Is Too Short energy, the latter perks my considerably sized ears. But you need to go deeper and unpack the ‘Difficult’ a bit.

Difficult can mean polarizing, not necessarily an absolute negative. If you combine this with self-awareness, you get a powerful combination for an early stage CEO. The things they are particular about — the stuff that makes them Difficult — they actually need to be good at, not just forceful. Is it a gruff exterior but with just a desire for excellence and impact, versus the difficulty being ultimately self-defeating to themselves and their companies?

Do they have a cofounder who can balance them out? Pair a Difficult CEO with a COO/CTO/CPO who knows how to manage alongside and whole just might be greater than the sum of its parts. Make sure to talk with this person as well. They can give their own unique insights into why they fit together, or share their own mounting exasperation.

Do they inspire zealots in addition to detractors? And do even the detractors say things like ‘hey, I wouldn’t want to work with him again at this stage of my career but I’d invest in something he founded without reservation.’ 🤩

For an investor, partnering with Difficult Founders also comes down to how you both think about relationship building. Are they Difficult but know what they’d be signing up for with you? Do you feel like it would take effort, but you could build a relationship? Do you trust them?

And what happens when you ask them about their reputation for being Difficult? The folks who recoil from these conversations or get defensive or blame others for every failure, that’s 🚨. But taking more of a learning mentality — believing that great companies *are* polarizing, but also talking about how building a great company will take more than just them, how their cofounder is a 1+1=3 situation, etc = ⭐⭐⭐⭐⭐

So net net, Difficult is definitely not disqualifying for us, but they do cause a second set of questions to understand whether the person can be a great leader/CEO and whether we’re going to be the best investor for them.

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Got a Cold Email Asking This Question. Here’s How I Answered

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Why Pairing Junior Executives With External Mentors Can Accelerate Your Hiring and Their Professional Development

Often at a startup it’s better to hire for talent, ambition, and commitment, than years in role or ‘did they have the job already somewhere else.’ For example, imagine a high-performing Operations IC at Stripe, with relevant experience and an itch to get into a role that allows her to spread her wings further. My intuition? Hire. Don’t worry that she hasn’t had a senior title or whatever. Just get her on board.

And then build scaffolding around her. Success isn’t her merely a signature on the offer letter, it’s making sure she excels as part of the team. And one way to help is with mentorship. 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. If there’s someone in industry she really admires but doesn’t yet know, reach out to them on her behalf. Or ask your cap table who is the best “XYZ” that they know and give them some skin in the game. Monthly 1:1s and as-needed tactical advice, introductions, and so on.

What should your relationship (as a founder) be with this person? They [mentor and mentee] need to have safe space together— neither can feel like you’re asking the advisor for performance feedback all the time because if so it’s less likely they’ll have honest, open conversations. But it is ok to keep open lines and ask for periodic feedback on how you can best help the team member grow, and/or pass your thoughts to the mentor on growth opportunities. Remember, the idea is that you’re all in this together on behalf of the company, and your employee.

I’ve also found that during a recruiting process telling these types of candidates 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. You can even present it as part of their ‘comp’ — an equity grant they have ability to distribute (with your approval).

Sometimes founders will question whether it’s truly a ‘good hire’ if they need to throw extra equity at an outside advisor. My POV is:

a) You’re hiring the type of person with very high ceiling before the rest of the market potentially realizes it. This is like getting a great athlete on their rookie contract. Their success will not just pay direct dividends but they are likely to be talent attractors going forward.

b) By bringing on someone a more junior into the role, you are probably giving them an initial equity grant a bit below what it would take to recruit a ‘been there, done that’ exec. Think of the advisor grant as coming out of that delta. You’re still ‘saving’ equity from the pool.

c) The advisor might have benefit to your startup beyond just directly helping the team member. They become another recruiting/networking vector for you to tap judiciously.

So that’s my argument for this type of hire and the secret way I share with founders to make it work. Good luck!

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12,000 Tech Workers Woke Up Friday To Find They Were No Longer Employed. Looking Back At My Own Departure in 2013.

Google was about 1,000 people when I started in 2003, which means last week’s layoffs were more than an order of magnitude larger than the entire company I’d originally joined. Even though I’ve been gone for a decade now and don’t know the majority of now Xooglers impacted, there were a number of 15–20 year vets included in the separation. While I understand the decisions to cut headcount and costs, hearing about these folks in particular made me sad. High performers and culture carriers for years — terminated via email and without the opportunity to celebrate their time with their teams.

It was easy to merge your identity with your employment at Google. Heck, they encouraged it. Googlers being Googley and eating, drinking, partying, celebrating, dating, marrying, etc together. The Mountain View campus was originally built to feel like a university.

As a result, abrupt separation can be really difficult for people who prioritized their work and their badge. Leading up to my departure in 2013, and after, I too feared the impact of losing that part of my self-worth. And I shared that anxiety in a blog post, reprinted below.

Originally Published June, 2013 [and lightly edited/updated]

hunter@google.com: From 2003–2013, it was a pretty powerful email address for me. I was the first “Hunter” to work at Google, so I got the six-letter name (the second Hunter went for retnuh@ — “hunter” backwards. Obviously he’s an engineer). And for that decade, sending something from @google.com pretty much meant any recipient would at least open the email, even if they had no idea who I was. Since I’d joined Google from a lesser-known startup the automatic relevance was especially pleasurable.

Often it wasn’t just an email address that drew attention. In the earliest Google years I had to be thoughtful about wearing logo gear outside of work. People would stop me on the street to tell me their Google search stories of triumph or failure, ask me about their website ranking, and, around the time of the IPO, make wild assumptions about my net worth.

When I started at YouTube (along with an even hipper hunter@youtube addy) in 2007, the attention continued (it just shifted younger and to more aspiring rappers than webmasters). Everyone always had a favorite video to tell you about. And they assumed you knew it among the hundreds of millions of videos on the site.

The braggadocious email identities and random interactions with strangers were cool, but the really sweet nectar came only as I started to take on more responsibility on YouTube’s product team. The role connected me with notable technologists, investors, and media industry figures. YouTube founder Chad Hurley was also very generous including me in stuff, which resulted in invites to parties, meetings, and meals above my pay grade.

I started thinking about leaving YouTube in late 2010 once Chad announced that he was stepping down from the CEO role. I knew a phase of YouTube’s evolution was coming to a close and that it was likely best for both the company and myself that a different leader commit to the next part of the journey. But one of the things that kept me from making this change proactively was ego — the joy of being relevant because of my role. It certainly wasn’t just this feeling; I loved the team and the community, too, but in hindsight, there was definitely an insecurity that kept me from stepping away.

As the saying goes, “Man plans, God laughs,” and not too much later in the summer of 2011, a combination of things — some under my control, others not — caused me to leave my position [I can be more clear now in 2022: Basically removed from my role when I was topped with another layer of management above me. On top of that, after suffering from four years of repetitive strain injury and no longer being able to use a keyboard without pain, it seemed like a good time to take a break and heal].

All of a sudden, the question I had asked myself — “Do I matter because of my job?” — was going to be answered against my will. After taking the summer off, I came back to YouTube in a capacity of my own creation, working in an area that had always been important to me: how YouTube is used as a platform for education, social change, and activism/free expression. This was the role I kept until I left Google roughly 15 months later (with another brief absence for paternity leave in 2012. Yippee!).

What happened once I vacated my throne? Did all of those folks who used to invite me to baseball games, dinner, and screenings disappear? The truth is that some did — most not because they were purely transactional relationships, but probably we just didn’t have as much reason to spend time together. Of course there were some folks who now totally blew me off because I was no longer the gatekeeper to what they wanted, or had the fancy title that they could brag attended their event, but I emerged on the other side realizing that I had plenty to offer without the @google email address. And that confidence, plus some other serendipity, is what caused me to finally decide to leave and pursue what became Homebrew with my friend (and also Xoogler) Satya Patel.

So why am I writing this now? Not nostalgia for Google — I continue to admire the company tremendously and care about many of the people but have no interest in returning. Rather, I want to acknowledge my own struggles with separating “where I work” from “why I matter” and self-worth.

You are not your org chart, your department budget, or your title.

Careers are sets of decisions where you have the chance to emerge from the chrysalis every so often and show the world, show yourself, how you’ve evolved. You are not your org chart, your department budget, or your title. Don’t let success at a company prevent you from pursuing scary and wonderful new opportunities to build. It took me a little longer than it should have, but from the other side, it’s pretty awesome.

Great Podcast on the Marketing of M3GAN with CMO of Universal Pictures

While I haven’t yet seen the movie M3GAN, I have seen the TikToks, the YouTube videos, and the box office numbers. And played my willing K-factor role sharing one of the clips with my wife (she wasn’t as amused as I was). When some piece of content breaks big this way on social it’s always interested to see if the business results follow, which often is not the case in our meme of the moment culture. Well, this one did, breaking $100 million in two weeks.

Media reporter Matt Belloni spoke with Michael Moses, the Chief Marketing Office of Universal Pictures, about how his team build the campaign for M3GAN and turned out an audience that was 50% under the age of 25. Numbers to DIE FOR….

I recommend you listen to the whole thing but here are some great excerpts.

On virality

I can certainly try to say that there is a science to it, but it’s not a business plan.Trying to bet on virality is just, it’s not, it’s something you can prepare for, but you can’t actually create, you can’t all the consultants and all the agencies out there in the people who purport to say, I can get your Tweet in front of six million people by tomorrow.

None of that is real. It’s all BS. Look, they can get it but then what happens, you know, things that Fascinate, the internet have a very short shelf, life and so it needs to be something that that that that the internet itself decides to kind of adopt and make their own and, and extend its life expectancy.

The Dance

So look, we knew we have this dance.And and when you look at the language of TikTok dance is just fundamental to to what happens there from music, but also movies, and TV shows what’s happened with the Wednesday Addams, dance, and the Matilda dance, these things.

Why Gen Z Fell Hard for M3GAN

I think this is also a case of this is this Generations first homicidal doll movie Every Generation tends to have them.

It’s been a moment, such a moment for all of us.It’s a classic but it’s almost 10 years since since Annabelle and it’s longer since Chucky.And you know this, A repeatable refreshable thing.

More gold in the podcast about timing of campaigns, Minions and Netflix maybe starting to understand marketing.