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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.

Is Their Company Name a Core Value Or Marketing Spin

You learn a lot when buying a first home. I learned that there are principal agent issues with your realtor exacerbated by the transactional incentive model. I learned that disclosure statements can be worded in a very specific manner that doesn’t truly describe what happens to your basement during rainy season. And I learned that the origin of a neighborhood’s name will reveal whether or not it’s descriptively accurate. What do I mean by this last point? Well, right next to where I live is called ‘Sunnyside.’ If it was given this label by the land’s indigenous peoples then it almost certainly is sunny. But if it was coined ‘Sunnyside’ by the real estate industry you can assume it’s foggy AF. [spoiler, in my case it’s foggy]

Hearing a company’s brand name always brings me back to this point. Was it coined because the promise provides a true north to its identity? A goal for every employee to live up to every day when they think themselves as representing the organization? Or was it a feint? Something that reassures each time it’s spoken but with no actual deep roots. A plastic flower instead of a living blossom.

I think of this every time “OpenAI” is mentioned. And these days OpenAI is mentioned a lot! The technology betas released by this group have been some of the most compelling, exciting, and energizing experiences our industry has shared in years. And I applaud them for moving quickly towards ‘general availability’ (although one can assume that the usage data becomes its own moat). Their work has entered my Top 10 of personal “isn’t software amazing” moments. But I then pause and wonder about the name.

What does ‘Open’ aspire to in this case? In their 2015 introductory blog post, the group said

We’re hoping to grow OpenAI into such an institution. As a non-profit, our aim is to build value for everyone rather than shareholders. Researchers will be strongly encouraged to publish their work, whether as papers, blog posts, or code, and our patents (if any) will be shared with the world. We’ll freely collaborate with others across many institutions and expect to work with companies to research and deploy new technologies.

My assumption is that Open was juxtaposed against a potential future ‘owned’ (and siloed) by Google, Apple, etc and the promise was you needed a fundamentally different structure to support this noble goal. But three years later, the organization changed into a for-profit, albeit one with capped upside for investors (100x cap. gulp.). The rationale was that the costs of development — talent and especially processing capability — was going to be substantial and OpenAI would need millions and millions of dollars to achieve their technology goals.

Institutions like Sequoia and Khosla, among other VCs, piled in. This was my first moment of HMMMMM. Now I certainly believe it’s possible to do well and do good, but I’ve rarely seen a multibillion dollar VC who was willing to sacrifice ‘well’ for good. Especially when hundreds of millions of dollars (billions?!?) might be up for grabs. Voting structures aside (which I know is close kept to the non-profit Board), how do you prevent a handful of venture capitalists from influencing and benefitting from this organization. The company you keep does impact behaviors, no? Can any transition to a venture-financed for profit be truly Open? Is this a new model or just a new FAANG?

Then you have potential king-making decisions about their technology and their capital. OpenAI led a $23m+ round in an AI powered note taking app via a startup fund also powered by Microsoft (and other?) dollars. Of course they want to see startups experimenting with their technology, pushing it forward the use cases, getting input from the developer community. But is throwing money (and frankly the importance of their brand, which right now is red hot) into startups a lead investor really Open? How Open does that feel to other note taking apps? (I’m not an investor in anything related to OpenAI or Mem, nor have I attempted to invest in either, although I did meet Mem very early on and thought they were nice people).

I’ve only met Sam Altman once or twice but he is clearly intensely curious and interested in future forms of equitable distribution (UBI for example). Maybe that’s why I’ve got really high expectations for this project and am picking on them a bit here. OpenAI seems to really be kicking ass on the AI part of the name. They have a chance to be as special and unique with the Open half — setting new standards as well for how an organization like theirs can create amazing technology AND broadly inclusive outcomes.

Leading Funding Rounds Now Requires More Thematic Focus To See, Pick, Win & Service Startups

I’m going to make the case that early stage venture *firms* who want to lead seed/A Rounds can be generalists (in the sense they have a set of GPs who cover a broad set of areas collectively), but that as a VC you, now more than ever, need some degree of focus. This doesn’t mean every partner is so narrow as to invest in just a single type of startup. But it does mean that if you cannot articulate the handful of spaces you are trying to dominate (from an investment returns perspective), you are probably not going to succeed ongoing.

Why do I believe this is now a reality (and I didn’t necessarily when we started Homebrew a decade ago)?

• “Software eating the world” (or my take, “software enabling the world”) means the breadth of problems startups are solving, the range of markets they’re participating in, and specifics of what they’re trying to accomplish during their first few years of operations, are so diverse that you cannot credibly hold evaluative criteria in your head for all startups. You might invest as a generalist but I don’t believe your returns will outperform.
• Similarly, founders of these companies are looking for lead investors who can de-risk their path forward. Being a pure generalist VC makes it very difficult to convince savvy founders that you have the industry relationships, relevant pattern-matching, and density of experience to be their best lead investor. I think this remains true no matter how large your firm’s Operations team is, or how much of a celebrity VC you might be (although both of those can be selling points).
• We’re back in a phase where alpha seems to be coming from technical innovation (crypto, climate, biology, AI) and not just business model application (XYZ but a marketplace!). It’s not just that it takes time to understand these technologies but each of them bring their own new networks and talent to the forefront. You have to be *in* these networks to see the best early stage opportunity, not just wait for intros to land in your inbox.

I’m not the only one noticing this change. Look at First Round Capital’s recent announcement of hiring investment specialists in Health Care and AI.

while we’ve tended to apply a generalist lens to early-stage investing, when you take a step back, you don’t have to squint to see that our investments tend to cluster around a few key areas … we’ve approached the age-old question of whether to be specialists and generalists as a balancing act … But there’s no denying the value in specialized knowledge.

and finally the FRC transformation

we’ve naturally moved a few ticks closer to a more specialized approach over the last five years — especially as we’ve grown as a firm and added to our partnership.

So if you don’t believe me, at least listen to one of the firms that started seed VC 🙂

When Private Companies Take On Nation States

The eggs wouldn’t stay in my mouth. Reading this New Yorker article over breakfast left me gasping so often that whatever I was chewing needed to find another home. So what *is* quantum computing?

Classical computers speak in the language of bits, which take values of zero and one. Quantum computers, like the ones Google is building, use qubits, which can take a value of zero or one, and also a complex combination of zero and one at the same time. Qubits are thus exponentially more powerful than bits, able to perform calculations that normal bits can’t. But, because of this elemental change, everything must be redeveloped: the hardware, the software, the programming languages, and even programmers’ approach to problems.

Now I finally understand the Ant Man movies. But it gets crazier.

At the root of quantum-computing research is a scientific concept known as “quantum entanglement.” ​​Entanglement is to computing what nuclear fission was to explosives: a strange property of the subatomic world that could be harnessed to create technology of unprecedented power. If entanglement could be enacted at the scale of everyday objects, it would seem like a magic trick. Imagine that you and a friend flip two entangled quarters, without looking at the results. The outcome of the coin flips will be determined only when you peek at the coins. If you inspect your quarter, and see that it came up heads, your friend’s quarter will automatically come up tails. If your friend looks and sees that her quarter shows heads, your quarter will now show tails. This property holds true no matter how far you and your friend travel from each other. If you were to travel to Germany — or to Jupiter — and look at your quarter, your friend’s quarter would instantaneously reveal the opposite result.

Basically Amazon and Google (along with some other private companies) are investing big in this research. And so is China. EVERYTHING is a use case.

Quantum computers could be used to develop biodegradable plastics, or carbon-free aviation fuel. … “We have good reason to believe that a quantum computer would be able to efficiently simulate any process that occurs in nature,” Preskill wrote, a few years ago.

But of course there are also some VERY specific use cases of note.

A full-scale quantum computer could crack our current encryption protocols, essentially breaking the Internet.

Just an amazing read. We might be very far from this reality, or within a decade.

Ukrainians Can Destroy a Russian Tank For About The Price of a Nirvana Artifact.

One thing is for sure, I never should have tossed those hair metal concert relics and other memorabilia from my teens. You know, the ones that in the eras before social media you’d buy and wear to school the next day to show off that you were At The Thing.

[Sidenote, my first concert was 1985 Madonna ‘Like a Virgin’ tour w Beastie Boys opening. The t-shirt might have had that old school raised webbing on her bustier top]

“I can think of Nirvana shirts that I sold 15 years ago for $10 that are now worth anywhere between $1,000 and $5,000.” Pop culture clothing apparently has had its own run-up in price during the recent years. If you’re still straining to understand why these things are cool, think of them as NFTs you can wear.

I’ve been sharing the above linked FT article a lot because it’s so relatable to us of a certain age. Perhaps even more than ‘mom threw out my baseball cards!’ (most of which have plummeted in price anyway), almost every I know had some variety of this gear that got tossed, worn out, lost, or traded away. Most of my stuff is gone although I did manage to locate a Grateful Dead Giants Stadium (NJ) tie dye and a Poison tour short (unfortunately later era — by that I mean third album). So it was top of mind when I read about another object which costs just a few thousand dollars.

“War is an economy. It’s money,” said Graf, a stout, bearded Ukrainian soldier in charge of his unit’s drone team. “And if you have a drone for $3,000 and a grenade for $200, and you destroy a tank that costs $3 million, it’s very interesting.”

As the Russian invasion approaches its year anniversary the suffering inflicted is heartbreaking. But the resistance of Ukrainians, and their forced resourcefulness, is quite inspiring. The activities describe above are of course more commonly known as asymmetric warfare and practiced by all sorts of fighters, many of whom are more morally compromised than the men described in the Times article.

To get the grenade closer to the desired weight, his team has been using a 3-D printer to try to make a lightweight casing that can hold the explosives needed to penetrate a tank’s armor. The painstaking task involves experimenting with grenades of differing designs, clasped in a vise in their workroom, and operating around the explosive mechanisms to fine-tune them.

It’s just like my life, only if making an error in an Excel spreadsheet caused my laptop to combust with the force of a land mine.

This blog post doesn’t end with some grand statement of economic theory or judgment about a world where some fashionable people are wearing off the shoulder grunge nostalgia to brunch while others are shaving ounces off of a bomb.

Too Many Existing Companies Merely Delayed ‘Cash Out’ Dates Without Yet Changing Their Fates.

If 2022 was the year of the startup layoff, 2023 is going to be the year of the wind down. It will suck — for team members, for founders, for customers of these companies, and for their investors — but by the end of the year we’ll have gotten through the toughest part of the correction.

I wrote this paragraph because we’re all coming back to work after a holiday break and wanted to preemptively address one of the two questions that seem to be taking 5–10 minutes at the start of every meeting. (Regarding the second question: yes, it was a very nice time with family).

My POV isn’t derived from a sophisticated macro analysis of the financial markets since that’s not my specialty. And isn’t accompanied by any universally applicable strategy that all teams should follow. That’s not how early stage venture is done IMO — each company has its own reality and as investors we should service founders to their needs, not some overgeneralized advice. But asserting we’re heading for increased pace of closures comes from a few on-the-ground observations:

• 2022 Layoffs and cost cutting have preserved already raised capital but in a significant number of situations this has just kicked the ‘are we investable’ ball down the road.
• In 2023 there will be a number of Series A-D companies that cannot clear that bar. And not enough venture investors willing to provide ‘bridges to nowhere’ (low growth, middling margins, no natural acquirers, team attrition ongoing, and so on). Think of it this way: add up all the anticipated 2023/24 capital needs of existing startups not in the top 10% of performance. It’s going to be larger than the ‘dry powder’ private investors are allocating to deploy into second decile performers.
• And there’s still quite a bit of valuation compression that needs to occur in order to reconcile private marks with public stocks. This might not deter all venture investors, but it will deter crossover funds.

I say this all very much being a technology optimist. There are many startups accelerating their growth right now, and founding teams working on ideas that will become the next generation’s defining platforms. But as professional investors we can’t avoid responsibility for managing out the realities of our portfolios. If we avoid these conversations you have no hope of turning a company around, finding them the right home where the work can continue, or assisting executives with the stress and moral choices that come in a struggling business.

Founders in situations where profitability isn’t a near term strategy should be working with their VCs to understand Are There Milestones We Can Hit Where There’s More Capital Available To Us From Existing Investors and What Milestones Do We Need To Hit For Us to Attract New Venture Capital, while also building their own direct relationships (remaining fully dependent on your investors for access to capital markets is always a risk).

VCs should not be afraid to ask their portfolio CEOs whether the current plan gets them to an investable milestone, and are they Spending Existing Capital in a Manner Which Will Build Enterprise Value? In the cases where answer is no, we should not be afraid to try and revise the plan, or suggest that a soft landing or partial capital return is out of the question. Burning through millions of dollars with just fingers crossed rarely benefits anyone. Note, this is different than going down to the wire to try and execute an strategy which, if successful, does change the profile of the company (a big product release, a major customer win, a pricing change, etc etc).

Founders, make the toughest decisions early in this year. If you don’t have the energy left to pivot or cut to profitability, is there another leader at the company who can? Be willing to reset valuations now if the incoming capital is from a good faith partner and it gets you past the next 12–18 months.

2022 is done. 2023 shouldn’t be status quo.

Some link-blogging for the last Friday of the year. Enjoy!

1. The Strange Afterlife of George Carlin (NYT) — Dave Itzkoff

Certain types of humor can be timeless and Carlin, despite having died in 2008, gets recirculated for his incisiveness. Itzkoff looks at why both side of the political spectrum have embraced (some might say co-opted) the comedian’s takes. 

That Carlin’s work endures long after him is not only a testament to his talents; it’s a sign that his frustrations, which he expressed humorously but felt authentically, still resonate with audiences, and that the injustices he identified in American society persist to this day.

2. Vivid by Living Colour (Pitchfork) — Stuart Berman

Thirty four years since its release, the lapsed time provides a perspective on Living Colour’s debut album that wasn’t available to critics in the moment. And it has aged well. 

It’s [“Cult of Personality”] one of rock’s greatest Side 1/Track 1 opening salvos. But given that rock radio was still pumping out pop-metal trifles like Winger’s “Seventeen” and Poison’s “Nothing But a Good Time” in 1988, it’s easy to understand why Vivid’s mainstream incursion moved in slow motion.

3. NFT Tax Loss Harvesting

What to do with those NFTs that you bought at the height of recent mania? The doodles and GANpuke that were going to usher in enlightened decentralized ownership and access to communities? Most people are self-HODLs, because there’s no buyer, no market and no reason to sell. But if you wanted to try and unload them for huge losses in hopes of taking a take write-off, well, there are services to help you. Warning it might not be as easy here in the US. 

4. Whatever Happened To… 

Friends Star Matthew Perry (GQ, Chris Heath)

Movie Actor Brendan Fraser (GQ, Zach Baron)

Two amazing profiles, each with their own types of pain. 

5. The Troubled Investments VC Firms Tried to Erase (The Information)— Kate Clark

If a tree falls in the woods and no one is around to hear it, does it make a sound? Kate Clark covers some examples of investors not just disappearing a startup logo from their website, but removing over-the-top blog posts and other ‘we’re proud to have backed…’ tributes when it turns out that maybe they should have been so proud.

I’m of two minds on this (and appreciate the media holding us accountable). On one hand these websites are marketing vehicles, not newspapers of record. So if you think of it as a storefront and not the New York Times, well of course you’re going to rotate the merchandise and present yourself in the best light. That said, on some of these blog posts I wish that they’d preserve them (even if they remove the active link from the site itself) and write a ‘correction’ intro that talks a bit about what they learned from the failure. That would be really impressive introspection.