“Did I intend to stay there for seven years? Hells no. But man, it’s a tough place to leave.” Five Questions on Startups, Newsletters & Life Post-Airbnb w Lenny Rachitsky

Our friendship began as many do – in a bar a few days after I’d been told that Lenny (a) just left airbnb and (b) was smart. Upon receiving the tip I clicked over to his Twitter profile where I saw that indeed he had left airbnb and that he was clearly super duper smart because he already followed me. A DM-slide and poof! cocktails and product management war stories ensued. In the time since he’s written some really wonderful posts and now a newsletter that’s going paid subscription, so seemed like an opportune time to ask him Five Questions...

Future’s So Bright….

Hunter Walk: So like, we’ve been friends for a year now. I went back and checked and it looked like I Twitter stalked you when you left Airbnb. Before we jump into Present Day Lenny, can you share how you initially got involved with Airbnb and, leading the witness, had you intended to stay as long as you did?

Lenny Rachitsky: I have this memory I’ll never forget of sitting in an early Airbnb all-hands looking at a big ass Airbnb logo (the old one) projected on the back wall, and thinking to myself “wait, how the hell did I end up at Airbnb??”

I was CEO of a little startup (Localmind) which we started in 2011, and things were going great. Growth was up, we were regularly getting featured in the App Store, and we were just about to kick off our seed round. But when Airbnb can knocking, we quickly realized that our most likely long-term outcome was going to be an acquisition, and that we couldn’t think of a single better company to end up at. So we sold.

When our team came on board, I quickly moved into product (I was an engineer up to that point), and held on for dear life for seven years. 

One of my favorite memories from the early days is of Joe talking to an engineer/designer who was working on an update of the homepage literally a few days before a major launch. She was asking for feedback on what she thought was a complete homepage. Instead, Joe offered, “build something the internet has never seen before.” 

And the funny thing is that she did (a sweet parallax’y hero image deal). That moment is actually a great microcosm of Airbnb. Never settling for good enough, always looking for ways to push further, and expecting the very best from everyone.

Did I intend to stay there for seven years? Hells no. When I started, I gave it a few years tops. But man, it’s a tough place to leave.

HW: What’s your decision framework for how you choose to spend time these days? I know you’ve done some advising and angel investing. But there have been some fun side projects too with regards to personal interests.

LR: My simple strategy for this year of exploration (which I’m so incredibly fortunate to have) has been to spend as much time as possible on things that give me energy. And as little time as possible on things that don’t. That’s it.

Though my original plan after leaving Airbnb was to start a company again, through this process, I discovered two things:

  1. What I don’t want to do: Specifically, become a full-time VC (no offense Hunter), write a book, or start a product management training course. These are things that folks keep suggesting I do, but I do not enjoy them and am trying hard to avoid sliding into these default paths.
  2. What I do want to do: I’ve discovered the things I enjoy most, at least for now, are writing, angel investing, and advising. So I’ve been trying to build a life where I can do those things.

As a result, these days, I spend about a third of my time advising, a third investing, and third writing.

HW: Ah yes, your writing. I’ve loved the newsletter and am glad to see you’re really committing to it with a paid subscription tier. I’m sure it was already opening doors for you professionally so what was behind starting to charge? Starting to build an income again? Signaling worth for the content? Challenging yourself to up your game?

LR: Folks seem to think I’ve had a well-thought-out plan with this newsletter. Honestly, I’ve been figuring it out as I go along. 

I first started writing as a way to get learnings out of my head, before I forgot them. Then, as people started asking me smart questions about things I didn’t have great answers to, it gave me an excuse to go learn more myself (and have better answers). So I embarked on some in-depth research projects (e.g. marketplace growth), looped in smarter people on topics I have little experience on, and collaborated with other great publications to reach new audiences.

Why’d I decide to start charging? For a very simple reason: I want to avoid getting a real job. I’m trying to see if I can make a real living doing this eclectic combination of writing, investing, and advising. It’s a life experiment! Plus, there’s a really neat flywheel between these three things that’s become a huge bonus.

HW: Does this also mean you’ll have a budget to get some custom illustrations from your wife? Along this same timeframe I’ve gotten to know you, she published a best-selling book. What has riding along that experience been like?

LR: If only budget was the reason she doesn’t help me with my newsletter design 😂 She’s definitely got better things to do, plus she tries to avoid the tech world as much as possible.

But, I’m glad we’re clear that Michelle is the real star of our family. She’s as talented as she is modest, and I couldn’t be more proud of her. If readers don’t already follow her on IG, you’re making a big mistake.

Watching her publish her book (excellent reading for the sheltering lifestyle btw) was an illuminating experience. It’s partly what convinced me NOT to write a book. For her, it was a life goal, but the economics are ridiculous, and I’m convinced that for what I’m doing, investing that time in a paid newsletter is a much higher ROI use of time.

HW: I’m sure there are new grads and folks early in their tech careers for whom you’re a role model. What’s the advice you’d give someone now – and has any of that been changed by what’s currently going on with COVID19 and what the world might look like on the other side of this?

LR: This may be the first time anyone has called me a role model, so I have to let that process for a few days.

Some timeless advice I come back to when wondering what to do:

  1. Do great work, create value, and good things will happen.
  2. Spend as much time as possible on things that give you energy.
  3. Work at the intersection of (i) things you enjoy doing, (ii) things you’re good at, and (iii) things that other people want.

Beyond that, for people early in their career, I would suggest optimizing for “variety of experiences.” Do as many different kinds of things as you can. Not only does trying a bunch of things help you find what you enjoy doing most, but also later in life you’ll find that many of the things you learned early on will be essential puzzle pieces in the work you end up doing. I’m pretty sure Steve Jobs said something similar, so it must be true. Explore, tinker, and take risks!

And finally, for the post-COVID19 world, my general take is that it’s going to further accelerate software eating the world (if that’s even possible), and so there’s even more reason to guide your career towards tech. At least the early part of your career. That decision early on for me, to get into software development, was the one thing allowed me to have this freedom to take time to explore and new paths. I’ve been so unbelievably lucky.

Thanks Lenny! I’m a happy paid subscriber to Lenny’s Newsletter and recommend you check it out as well (there’s a free tier too).

Privilege & Anxiety Clash, Then Make-Up, In My COVID Brain

Earlier this month I finally reconciled a conflict that challenged me since COVID really crashed our shores in early March. Basically that it’s ok to both feel fortunate that we’re staying-at-home together as a healthy family with more resources than the average American, while at the same time acknowledge and honor the anxiety the situation is causing me.

Wanting to get my daughter back to school where she is able to learn, develop and explore. Wanting to support the founders we backed as people (not just investments) who are confronted now by market forces for sure, but also needing to knit a social and emotional infrastructure to help their teams. Wanting to sit next to my partner Satya at Homebrew HQ, not just Zoom from my dining room. Wanting to not hold my breath when someone walks by me, even if there’s six feet of separation.

For a few weeks any time those needs came into my head I pushed them aside, embarrassed that this was where my mind was going while people lost their jobs, suffered from a horrific virus, or any number of other more substantial dislocations than we’d encountered. So we gave to different charities (support FrontlineFoods) and checked in on friends with difficult situations, because those were good legitimate things to do.

But I wasn’t sleeping well. One night I fought vampires. Then Thursday it was some weird scenario where I left early from a friend’s wedding and couldn’t get back into the venue when I felt ashamed to have ditched. Then there was that one with the tentacle porn… nah, not really that one, just wanted to see if you were still paying attention.

When people would ask “how are you holding up” (or whatever basic inquiry you’d start with before jumping into the meat of the Zoom), my standard response was bravado and apology. “Great, really lucky. I know there are so many people suffering.” And it was true but only a half-reveal. So in one particular conversation I didn’t stop with that explanation but added on, “…still at the same time I don’t want my kid to have a childhood shaped by this experience. And I want to be giving great advice and counsel to our CEOs but in some cases we’re just going to have to figure it out as it evolves. And my puppy peed on the floor and I don’t know if she’s just mad at us or if something is wrong. And…” Well, it didn’t go on forever but you get the sense.

Then my conversation companion paused and shared his own version of what had been troubling him. And it was just as messy, and dumb, and serious, and trivial. And he was happy to be able to shed the “I got my shit together. Wartime CEO.” suit for a second and just be human. And I started having versions of this conversation with more people. And I was no longer battling vampires or missing weddings in my sleep.

“Journalism is built on a foundation of trust and truth. While I have friends who are also sources, those friends know I wear two hats” — Five Questions w Axios’ Kia Kokalitcheva

Kia Kokalitcheva is a San Francisco-based technology and business reporter at Axios. She covers tech, Silicon Valley, and venture capital. We’ve known each other for a while – she was previously at Fortune – and besides appreciating her work, Kia has always struck me as a no BS person who will tell you where she stands. Whether I agree with her or not on an issue, I like the forthrightness. And I’m happy she agreed to Five Questions with me.

Hunter Walk: If “the medium is the message,” how does Axios’ newsletter-first strategy shape the reporting you do and the format it takes?

Kia Kokalitcheva: Our newsletters have evolved over the years but today, we’re constantly thinking about what makes a story good enough to “lead” one of our newsletters. Why should this be the main story a subscriber spends their time on when they open the email? For me, that means either a story with original reporting (a scoop, an interview, an original dive into a subject) that readers can’t get anywhere else. If that’s not possible, then original analysis or arguments about information already out there! 

At the same time, we know subscribers often use our newsletters as the way to get their daily dose of news in one shot, so that also means catching them up on smaller news they may have missed, links to longer stories if they want to go deeper, other information they may want, charts, etc. 

HW: I’ve never quite understood the relationship between editor and reporter. At some publications it seems like editors have to approve story topics, whereas at others, it’s more of a post-submission content review/improvement function but not an approval per se. How have editors played a role in your career across three companies? 

KK: So the thing to know is that there are different types of newsroom cultures, and different types of editors. Some are more driven by editors while in others, reporters take the lead, and some are a mix, varying across the different products they put out (website, newspaper, magazine, etc.). 

Because I’ve always worked in (mainly) online newsrooms, I’ve always had a lot of flexibility and room to use my judgement and write the stories I think are needed, important, or interesting for readers. But editors have also always been a great source of knowledge and wisdom about improving things like sentences, story structure, angles, subject matter expertise, and guidance in getting the necessary reporting done. At Fortune, for example, the range was wide—from self-guided decisions to write a short online story about Uber’s latest big news, to pitching the print magazine’s editors and then going through very heavy-handed (but amazing) editing to get to the final process, and everything in between. 

At Axios, I regularly go ahead and write stories that I know are important for our audience, and get an editor to work their magic on the draft before publishing it. At the same time, I also regularly chat with certain editors like Dan (Primack), who is also my boss, about story ideas I’m thinking about before I start working on them. 

HW: It’s only natural that a technology reporter also develops friendships within the tech community. How do you navigate these relationships when you might be reporting on someone you know (or their company)?

KK: Journalism is built on a foundation of trust and truth. While I have friends who are also sources, those friends know I wear two hats — the professional and the personal — and know that I separate those two. I am pretty good at setting and managing boundaries. Friends know what to say and not to say, and they also know that if we’re hanging out in our off time, I’m not going to burn them if they accidentally blab. 

HW: What’s your take on reporters unionizing at media companies and news startups? And do you think we’ll start to see similar at technology companies (I guess Kickstarter may be the first)?

KK: To be honest, I don’t personally have an opinion on unionizing, so I’ll leave it to others to decide whether it’s a good move for themselves. But I’m not surprised to see a number of newsrooms make that choice — newsrooms have been precarious workplaces thanks to the turbulence of the industry. 

As for tech companies, Google and Tesla have seen some efforts on that front, and Kickstarter did recently vote to become one. Ultimately, it’ll come down to each workplace and how its workers feel vis-a-vis management. 

HW: Over the past few years there has been more open discussion of the ways the tech industry has mistreated women within its culture. Do similar issues occur within journalism and do you personally feel like as a female reporter it’s getting “easier” to do your job outside of this bias?

KK: I think a lot of what’s come out really is what women have to face in the workplace in general because it’s a societal problem. So yes, women in journalism—as in workplaces everywhere—face stereotypes, bias, discrimination, sexual harassment, and so on. 

We’re long past the days when women weren’t allowed to have a byline and could only get “researcher” jobs at news outlets, but I’m also not sure it’s noticeably changed in the 6 years I’ve been doing this. But I do see a lot of encouraging signs! For example, Axios’ original team of tech reporters was majority-female, had a woman as the tech editor, and a woman leading its main newsletter (the team has since expanded and evolved so this has changed a bit, but we still have strong female representation). I also recently noticed that most VC reporters I know or bump into at industry events are women, so like it or not, this industry has to answer questions from one (or many) of us even if we’re still underestimated sometimes 😉 

Thanks Kia – everyone go follow her on Twitter and read her at Axios

What’s Wrong With Tech Folks Who Attack The Tech Media. And What’s Wrong With Tech Media Today.

Lots of mutual bad faith. Reporters I respect indulging themselves in screenshotting and quote dunking tech folks, performative for their tribe. Executives, investors and other prominent SV personalities believing they’re Martin Luther tacking 95 tweets to the doors of establishment media shouting down supposed hypocrisy and calling out errors. I’m a tech industry bro who also is a journalism fanboy, and the above just makes me sad. So let’s do this and get both sides mad at me….

My friends in the tech industry, here are things you do/say about the media that I believe you should rethink:

  1. Not all critics are “haters” and please stop adopting the language of our President to deride reporting. Fake news, online hit job, MSM, a takedown — these glib characterizations (even if you believe them to be true) bring so much nonsense and baggage along with them. Read the negative coverage and decide what’s legit, what’s a misunderstanding and what you want to reject/ignore. Then just move on.
  2. You are not as much of an underdog as you think you are. Over the course of my career in technology, we’ve moved as an industry from scrappy underdog to dominant incumbent. Industrial capitalism has given way to technology capitalism. The largest public companies are tech-related. Many of our skills are in deep demand from labor markets. I know – especially at a young startup – it can feel tenuous and risky, but compared to almost any other industry, in every other geography, we are structurally empowered right now. And we – as an industry – have continued to build some wonderful stuff, but we’ve also had examples of fumbling the football with regards to appropriately understanding and prioritizing the secondary impacts of the work we do. And of looking at the culture of our own workplaces and building spaces that can be healthy and inclusive. So just as you think the media is “punching down” when they critique us, they generally see it as “punching up” and hold power accountable. Sometimes they fuck this up – don’t worry, I’m going to yell at them in a bit too – but you’re not some precious hothouse flower which needs protection, so spare me the “man in the arena” quotes.
  3. You want to content market yourself but then think follow-up questions from the press are not worthy of response? The media isn’t looking at your github pull requests and asking glib questions. They’re reading your blog posts, your tweets, your podcast transcripts. If every individual, VC firm, startup is using these platforms to build their brand and puff their chests out, please spare me the indignation when reporters want to ask you for comment. It doesn’t mean you have to respond – no one owes anyone this – but realize that when you put yourself out there for purposes of self-promotion (and it’s all self-promotion – me included!) that you are inviting a magnifying glass.
  4. Pay for media. You care about reporting? Make sure you are paying for it. Even if it’s not perfect. You think there’s truly a market for “unbiased evidence-based reporting?” Write a $100,000 check to a reporter and let them try to do it. Put some skin in the game if you want to critique journalism.

Ok, my reporter friends. Here are specific things that some of you – or your industry colleagues – do that I believe undermine your credibility in specific instances.

  1. Red Team” yourself into a biased corner. A reporter I know told me that their job is only to Red Team vs tech. I felt sad for them. It’s not that a reporter’s job is to write “both sides” of the story, or to balance their negative coverage with positive stories, but I do fear that over time this type of newsroom (and culture) narrows its perspective. And also applies the same level of Red Teaming outrage equally to very different circumstances. For example, highlighting a young individual who made a stupid tweet or blog post vs truly speaking truth to power.
  2. Overgrant anonymity, especially to direct quotes. I’ve written “you can always find an anonymous former employee to trash the founder.” There’s a school of thought in some journalism circles that anonymity is a precious privilege to be given out only when the information being secured is so important to public good, and the person doing the speaking is putting themselves in such a compromising position, that it’s worth robbing the reader of their ability to judge the information in context of who is saying it. This is the school I subscribe to. Every day I read articles which give full anonymity to almost anyone while also do direct quoting of what they said. “We wouldn’t get the good quote otherwise” some reputable reporters tell me. Well you know what, then maybe don’t get the good quote. If you want to grant anonymity, don’t use direct quotes. And if you must, at least provide context. “…said ex-employee” is meaningless – was this a VP there for eight years with intimate knowledge of the situation? Or a low level individual contributor there for two months and now talking out of their ass? Reporters want to say “well, you need to trust us on this sourcing” but I’m sorry, that’s a lot to give over for 95% of issues. If you can’t get people on the record, maybe it’s not a story. If you can only get a handful of low level people to comment anonymously about a 50,000 person company, maybe it’s not yet a story. Do more work.
  3. Blame the media business model or editor for your content or the headline. “We’d love to do more [longform; sourcing; data gathering; fact-based headlines] but [my editor, the social team, the business model] doesn’t allow us to.” I’ve heard enough variations of this from enough good reporters. And I feel for them. But please, some accountability. I’m sorry if these pressures are putting constraints on how you want to do your job, but you need to own it. And try to change it. Just as you might ask tech workers to not be part of companies or systems which compromise their values, I ask you to consider the same.

So what to do? The tech industry needs to understand that a challenging press is important component of society. And some in the tech press have developed a number of habits/assumptions which I believe weaken their own impact. And I generally wish more reporters could experience the other side of the table – Jessica Lessin’s observations as she went from newsroom to startup have always struck me as the type of self-reflection that I wish we could make more common. Maybe I can figure out how to let a journalist embed in Homebrew for a week….

2/16: Besides some good Twitter chat, two people wrote longerform about this topic: TechCrunch’s Alex Wilhelm’s “Tech, media and what journalism is for” and Chris Anderson’s “The problem with tech media is not that they don’t understand tech. It’s that they don’t understand business.”

2/17: Another good addition from Toni Cowan-Brown called Tech vs. Media: A Simple Solution, But A Difficult Path.

2/20: MG, who has actually been on both sides, writes Both Sides.

How To Open Your Own Public Library

We opened our own public library this week. On our lawn. It’s modest in size but made us part of a worldwide network called Little Free Libraries. Books have played a huge role in my life – always an enthusiastic reader and my first jobs were at a hometown public library and then a local indie bookstore. So when my daughter noticed these curious boxes on people’s lawns all over SF filled with books, we leapt to support her curiosity.

Turns out Little Free Library is nearly 11 years old and started with one guy in Wisconsin! Now there’s a global network of people who buy or build their own, for installation at their home or business. You fill it with books and encourage people to take or leave their own. Some folks are very creative with their designs (Instagram).

Decentralized communities supported by technology – I spent much of my product management years helping to strengthen platforms that encouraged these types of relationships. In an era of political tribalism and ‘glass half empty’ views of the Internet (yes there are some very real problems but…) I find great optimism and hope in observing and participating in these efforts. And now I finally have somewhere to put those copies of Sapiens and Ray Dalio’s book that I never actually read.

Did Employee Startup Equity Change Much in 2019? I Don’t Think So.

2019 didn’t herald any major innovations in how early startup employees receive equity. Which is a shame since, on the margins, the most talented hires deserve more of it. On the positive front, I did encounter more founders making early exercise available to their teams and much less resistance overall to the idea of a 10-15% pool (perhaps because valuations continued to increase so founders themselves were taking less dilution in financings). A subset of startups we worked with also made changes to their equity plans which allowed for longer exercise windows in the case of an exiting employee in good standing (usually who have stayed a minimum of two years at the company).

Perhaps I’m just not looking in the right place for changes – it’s more likely the non-venture backed companies that will explore dividends, profit-sharing and other mechanisms for rewarding teams in building an enduring business. For startups like Carta, this looks more like structured secondary programs.

It’s the second time founders – especially solo founders – who often think most deliberately about these issues. They saw how previous outcomes did – or didn’t – reward teams proportionately. They have people in mind they want to pull into their new venture and know often these folks will be leaving money on the table from current gigs. They are often more aware of what their role requires as CEO (and sometimes their own strengths vs weaknesses). And as they’ve articulated to me, rather than have a single cofounder, they’ll take 20% of the company’s equity and provide real incentive to the founding team and early executives.

Did you see anything interesting in 2019?

How I Calmed The Failure Tiger Nipping At My Heels

For all of my 20s and much of my 30s there was a failure tiger nipping at my heels. No matter how fast I ran, it was still there – hot breath, sharp teeth and a whispered growl promising a bleak future. The beast was born from a mix of personal insecurities and childhood trauma. An idea that I had opted into an industry that was waiting to spit me out as soon as I messed up. And that as I reached my mid 40s, the fall would be inevitable based on hitting irrelevance in an industry that valued youth and code. The stories of similar knocking down of men in other industries, including my own father.

Into grad school, a startup and then Google, I was sure the tiger existed. It drove and motivated me, but also poisoned the accomplishments; played a role in anxiety, sadness and physical ailments. Insidiously, the tiger was able to convince me that its existence was also the only reason I was succeeding. Satisfaction and happiness would become complacency. And complacency would result in failure.

Photo by Mike Marrah on Unsplash

I write to you at the end of 2019, having been free of the tiger for seven years or so. What did it? Becoming a parent and the support of my wife; therapy; and the very material realization that I had saved enough money to create a safety net for my family. [Side note, that’s one reason I support detaching health care from employment and other public sector benefits which give Americans security apart from their work].

If you’re being chased by a tiger, or a dragon, or whatever symbolic metaphor your fear manifests itself as, know that you’re not alone and that it’s a state of being, not a destiny. And if the holiday season is especially hard on you, or 2019 has just been a shit year, you can always email me [hunterwalk gmail] and I’ll try my best to share any useful details of my experiences.

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The Five Most Influential VCs of the 2010s

“Hey Satya, should I write a post about the most influential VCs of the decade?”

“Sure, expect a lot of opinions :)”

Photo by Vitto Sommella on Unsplash

We’re just a few weeks from the end of the 2010’s. Now the calendar-truthers will tell you that the switchover from 2020 to 2021 is more significant because that’s the *actual* beginning of the new decade, but come on, time is a flat circle and we all know moving from a —9 to —0 is a bigger deal. So as reporters and pundits start their “Best of the Decade” lists, I’m turning the gaze inward and asking the question, “Who Were the Most Influential VCs of the 2010s?”

NOW, this isn’t the “best” VCs of the decade. Or the most famous. Or the nicest. Instead it’s just my hot take on who were the handful that had the biggest impact on my industry. This doesn’t even necessarily mean they had the biggest impact on tech (let’s stop thinking that venture capitalists are the butterflies whose wings cause typhoons). But their actions, choices and words did, in my opinion, create changes that cascaded over the investment class. Sometimes in ways they intended and perhaps in some other cases, in ways they couldn’t have even anticipated!

[Deep breathe] In alphabetical order, here are the MOST INFLUENTIAL VENTURE CAPITALISTS OF THE 2010s

Marc Andreessen & Ben Horowitz

a16z played disrupter, launching their first fund in 2009, based on a bold set of statements which, even if they were not individually unique, had never been combined before into a firm. They’d offer services like recruiting, sales and BD help, and marketing to their startups, building out an agency-like model and employing well over 100 team members. All of their partners had to be former founders (since relaxed), sounding the bell that not just operators, but founders, would make the best investors. And since there were only a handful of companies which truly mattered each cycle, you couldn’t “overpay” to get into them, you had to be in them – thus capital and brand would be weapons, pushing other VCs to raising the magical “billion dollar fund” or be left without the dry powder to stare down Marc and Ben.

Now as we enter the 2020s, the majority of large firms have some operating support, core + opportunity funds that tip well past $1b and promote themselves with content and conversation. The message to them was clear – you don’t have to play a16z’s game but you can’t ignore them.

Josh Kopelman

Over the course of the 2010s, seed investing went from a clubby handful of individuals and “micro VCs” to an outpouring of capital and multi GP firms. The institutionalizing of seed financing was driven by the aptly-named First Round Capital which Josh co-founded and for a long while, was clearly the visible frontman of the group. First Round went deep on “platform” far ahead of anyone else in this stage. They are also the first of the early stage seed funds to really plunge into a generational transition, as the initial GPs have started to step back. Will seed VC be a multigenerational game? Remains to be seen industry-wide, but LPs and other firms are looking to FRC as bellwether of how to do it.

The money cannon currently being shot at early stage companies (and funds like mine) owes a lot of its success to Josh’s vision and now the big multistage funds have come down market as well to try and get a piece…

Aileen Lee

Aileen could be on here as an example of large fund GP breaking away to start their own firm – which is clearly another trend of the 2010s – but I’m actually including her for coining the term ‘unicorn’ (companies which have hit $1b threshold in private valuations). In doing so, Aileen didn’t just give a name to a phenomena transpiring, she played a role in catalyzing an aspirational target for companies and investors to hit — “unicorn status.” Funding rounds, press headlines, even recruiting pitches, all sought to declare “XYZ is a unicorn.” The observation of unicorn inflation caused more unicorns to be created! Talk about unintended consequences.

The next few years – maybe even the next decade – are going to be about these highwater valuation marks being tested — by the public markets, by potential acquirers, by common shares under a preference stack. And without a doubt, Aileen’s smart analysis influenced years of investing behavior.

Ellen K. Pao

Ellen’s might have lost her lawsuit but the filing itself started an avalanche. Whisper networks became real conversations and firms up and down Silicon Valley started addressing their “women problems” – basically, that they didn’t have many among the managing and senior partners of their firms. While we’re nowhere near parity – and female entrepreneurs are still dramatically suffering as a percentage of venture-backed dollars – the landscape looks very different than it did before Ellen stepped up. And I can’t imagine it going back.

Hopefully the work of Project Include, All Raise and other groups make the term “underrepresented community” an anachronism before the next decade is up.

You’re Probably Asking the Wrong People For Career Advice

“Hey, I want to pick your brain about a new opportunity I’m considering. Can you grab a coffee next week?” My recoil when receiving these emails isn’t because I don’t want to help – I love aiding talented folks find the roles and cultures in which they can thrive! Rather it’s attributable to my concern they’re asking the wrong people for advice. And this may cause them to make a poor decision.

Photo by NeONBRAND on Unsplash

Here’s what I believe: when considering a specific career path decision or evaluating an offer with a particular company, I’ve found people tend to concentrate mostly on the opinions and inputs of two groups: their friends in similar jobs and the most “successful” people they know within the industry. Seems like a reasonable strategy, right? Depends.

Industry friends and luminaries tend to tell you what *they* would do given your situation, but often aren’t able to see the choice and the trade-offs through your eyes. “If I were you….” is the common opening of a response, which says “I’m not thinking about you, I’m reacting based on my own values and interests.” It’s not that these groups are useless conversations but with them I’d focus on two pieces of information: across both groups is there consistency in the recommendations they make and, especially for the latter group, what questions did they tend to ask themselves when making similar decisions?

Ok, so who do advice seekers usually *undervalue*? (A) People who know you very deeply regardless of expertise in your specific professional work and (B) individuals who have direct experience with the company, role and people you’re considering.

The people who know you well are more readily able to actually see the opportunity through your own eyes and challenge (or confirm) your sense of self. I don’t believe they actually need to understand the specifics of the career, they just need to hear you describe it – what’s interesting about it, what concerns you, and so on. “Knowing what you know about me, am I thinking about these opportunities in a manner which makes sense to you? Am I correct about when I’m happiest and doing my best work? Are there things I’m afraid of which cause me to overestimate or underestimate the risks?” Pick the right people and it’s like holding a truth mirror up to yourself.

Photo by Andre Mouton on Unsplash

As for the individuals with specific experience, but who might not even know you – what you’re seeking there is confirming or disconfirming information about how you’re understanding the role. Let’s say you’re considering a Google PM offer. What you want to do is find some Google PMs and ask “hey, what intrigues me about this opportunity is that I’m interested in learning how a large company runs itself and even though I know it might take longer to ship a product, I want to know that product will have a big impact. Does this correlate with how you experience the role day-to-day?” With this information you can get very specific around the pros and cons of the opportunity — ensure that you are seeing it with realistic eyes to confirm that it’s what you believe it to be.

And that’s it – if you have people who know you and can validate your thinking given who you are as an individual, and if you have people who understand the job deeply and can validate your understanding of the work, the culture, the company, well, you should be in a position to make a good decision.

No, It’s Not “Like a Startup Within a Big Company”

Pushing this into a blog post because my tweets are on rolling 30 day autodelete 🙂

And since a “blog post” should have some value-add over just pictures of tweets:

Ex-MSFT exec Steven Sinofsky turned me onto this thread from Textio cofounder Jensen Harris