Advice/Truisms the book provides loud and clear

Psychology / Social Dealings

  • High-level decisions, in business or government, that affect thousands of people and millions in revenue, are made eventually on:
    • Gut feel
    • Residue of historical politics
    • Persuasive messages (or the lack of them) catered to an audience that was Busy, Impatient and Disinterested.
  • Never trust the survivor of a massacre until you know what he did to survive.
  • Every real problem in a startup is a people problem, and as such, they are the hardest to solve, since they don’t often have a real solution.
    • Startups are experiments in group psychology.
  • In a world where superficial relationships and glib bullshit are the rule, there’s nothing more fearsome than to see true loyalty at work.
  • To have influence in the world, you need to be willing and able to reward your friends and punish your enemies.
  • Cash is the poor man’s credit.
  • The secret of great fortunes without apparent cause is a forgotten crime, as the crime was properly done.
  • America still loves an underdog. You will be surprised at how much help you get when you are the underdog in the fight.
  • Anyone fights to death when their back is against the wall. Try not to compete against folks in that position.
  • Information asymmetry doesn’t just come from you having more information than the other side of the table. It also comes from knowing what the other side of the table cannot access. The author showed this making a bluff about Google, that Amin Zoufonoun, a then-recent defect from Google to Facebook, could not verify.
  • “There is no knowledge that is not power” – this is especially true in the people-space.
  • Total commitment, like unconditional love, is the only type that matters.
  • “It’s love due to surrender via enchantment.” Past a certain point, it’s you the buyer who is seducing yourself into the acquisition.
  • Cognitive dissonance effects – what do people do?
    • Skirt situations that aggravate realization that realities are contrary to your most deeply held beliefs.
    • Ignore data that make their mental contradiction more apparent.
  • All ambitious men either want to please their father or avoid becoming them.
  • Truth in the world only resides in mathematics proofs and physics labs. Everywhere else, group opinion becomes the capital T truth. Most people who make a big show of being attached to the truth are deceiving themselves.

Startups

  • Sign that a startup is bad – employees have fallen prey to Stockholm syndrome.
  • A counter-intuitive sign that a startup is bad – it makes gobs of money that hides the problem or causes folks involved to overlook them. Several ad-tech startups made upwards of $5 million a month. Unless you knew the space thoroughly, you’d be misled.
  • Most important step in a startup, as in life, is picking a partner.
    • With the right team, no man or org. can stand against you.
    • With the wrong team, internal problems will cause premature death.
    • To-do for a startup – have one captain with > 51% equity.
    • Join a startup where you can trust the captain to navigate the ship better than you would and then fall in line to them.
    • 12 of 30 YC companies in author’s batch had founder disputes and died due to infighting.
    • Only CEO title matters, rest is BS.
    • Contain the fund-raising begathon to the CEO. Firewall the rest of the company away from acquisition and other mess.
  • Angels are rational (mostly), will not expect 100x return. VCs will.
  • “Investors like to feel you’re their bitch or their boy when they wire you a bunch of money. Some other pack of moneymen also having you by the short-hairs mutes that sense of ownership.”
  • The story of pretty much every startup is peppered with tales such as that of the author.
    • Backroom deals negotiate via phone calls to leave no legal trace.
    • Behind the back betrayal of investors or cofounders.
    • Seductive duping of credulous employees so they work for no money.
  • “Starting a company is like eating glass and staring into the abyss of death.” -Elon Musk
  • What startups are most comprised of, between the few and short-lived happy moments –
    • Gnawing doubt
    • Nauseating anxiety
    • Endless toil
  • What distinguishes startup-founders? (Not raw intelligence or technical ability)
    • Ability to maniacally focus on one thing only.
    • Ability to take and endure endless amounts of shit.
  • Things for a startup founder/employee to think through –
    • Big companies do M&A to inject new DNA and hybridize.
    • What would make you valuable DNA material?
  • Being part of a hot startup is the new union – that will get you access to better working terms!
  • A startup is really a leverage to score a better job offer. Corporate M&A in most large companies is glorified recruiting.

Tech Industry / California

  • New media emulates the forms of the past, in the early stages. Ads on the internet emulated in-the-mail ads. Early TV was radio with an image, poorly utilizing the new medium. (KR notes: To some extent, this is true of UI/UX as well. Early mobile UX was just desktop ported badly. For what other areas is this observation true?)
  • The valley is radically different from NYC, for individual social standing
    • In the East, it takes time to rise, and time to fall. In California, “any hustler who can make superficial friends of the California variety and publish a few blog thought-pieces is as much a part of the ecosystem as the old folks.” Standing/cred falls easily as well.
    • California is presented as “The Land of The Stateless Machines”.
  • (KR notes: not very convincing. We’ll see where recent scandal subjects end up 2 years from now in California. East Coast isn’t as stateful as author claims either, else Jamie Dimon should have been out of a job and in jail now?)
  • Ironical that the person the author loathed was punished for his one iota of kindness.
  • A good reminder for what “swimming with sharks” means –
    • “We would bleed $20k a month in legal fees, and between that and salary and other expenses, we’d be dead in 9 months.”
  • There are 2 weak points for any tech company, no matter how large –
    • Investors
    • Potential business partners.
  • So many men abandon their purpose when close to the goal.
  • Only in Silicon Valley, one can mobilize an army of lawyers, accountants, engineers, PR people, public company wheeler-dealers, partner relationship people – without actually having to meet them. Emails/phone calls with work.
  • “Narrative fallacy increases our impression (illusion?) of understanding.” – NNTaleb
  • Think of any interview, whether interviewer or interviewee, as a jump start on team bonding.
  • The author added Google Alerts on all companies he was following or interested in. Makes perfect sense.
  • Hybrid deals often happen in the valley. “We want A and B from the company, but not C, and we want the company’s tech/IP.” They are just not spoken about much.
  • In 2011 (a year before IPO), Facebook Ads was 30 engineers and 1 designer, spread our 12 products. Let that sink in for a bit, you who thought highly of FB in 2011/2012.
  • What makes a tech company like FB succeed?
    • Bold, unconventional experiments. Most failures, tiny fraction notable successes.
    • Immediate course correction to prune the failures.
    • Internalizing the experience and the learnings via the culture.
  • Nature of valley success:
    • Try 10, 7 flop, 2 mildly OK, 1 is a thundering success.
    • You can explain the OK and the success only after the fact.
  • “At their extremes, capitalism and communism become equivalent.”
  • There are more blind-spots to Silicon Valley firms than meets the eye (e.g. FB circa 2012). The key is to find these and make an opportunity of those.

Career Gems

  • When the stakes are high, things settle and converge fast. FB ads, as per author, settled from 2011-2014. This explains up or out – you are either on the right side of history or omitted from it (unless you write your own).
  • Don’t compete with someone who has their back against the wall. You’ll lose.
    • Facebook had Paul Adams, a former G+ guy explain to them public-facing aspects of the product after it launched.
    • Facebook was working Sundays during the FB-G+ face-off, while Google was not and Google was making up metrics when none existed.
    • It was clear which company was fighting to death.
  • As in life, so in business, maintain a bias for action.
  • “It was a terrible assignment for anybody who wanted to make his or her mark at Facebook (and it would take me months to scheme myself out of it).”
  • Learn to spot bad assignments.
  • What made Sheryl an effective manager –
    • Picking up subtle psychological cues from an off the cuff remark here or there.
    • Unearthing a lingering issue that lay dormant (had context in her head/notes)
    • Making sure every voice was heard, but no voice heard too much
    • Tempering down irrelevant drama and ensuring progress was made.
  • “Act like you belong there, even if you don’t” – Holds true for any fast-paced, competitive workplace.
  • “No speed limit” passes are issued only by Zuck (or your manager) – everyone else races ahead at peril to their careers.
  • Author promised $100mn in revenue that year to get 3 eng + 1 PM in resources (~$4mn in allocation).
  • “I’ll either hire you right now or a year from now, I’ll hire you to work for the guy whose job I am offering you right now.” No prize for guessing which valley celeb said this.

Ad-Tech

  • The Ads circle of life goes such: Money funneled into product and ads development, transfers to attention in someone’s mind, that attention is tracked and monetized via ads development, transfers to at least 10x the original money.
  • In ad-tech, the ad-server is the oracle. Nobody else in the chain involved trusts anyone else they are talking to.
  • Learnings from the ad-tech space:
    • Identity join is what everyone is (or was?) after.
    • Big Brother is actually unknown companies – Acxiom, Experian, Epsilon, Merkle, Neustar.
    • How offline data helps – pulled from CRM -> analysis -> carefully created and curated segments.
    • In-the-mail ad usage shows there is more offline money waiting to be converted.
    • Datalogix and Neustar buy online real estate anywhere where personal data like name and address meets a browser tab.
  • If FB lasts a few decades, it could become a primary key to buying behavior and commerce history?
  • Why mobile is different from browser cookies – device ID lasts forever.

Questions that the book provokes

  • What is my ability to survive random failures, the ones created by Chaos Monkeys or FB-like environments around me?
  • How good am I at correcting mistakes before they actually occur, like the chaos-monkeys and other automated tests deployed in tech infra?
  • Is what is happening in the valley today comparable to the industrial revolution? If yes, what is my role in it? What are the roles up for grabs? Which roles are being played well, and by whom?
  • Look at the volume of work the author got done in 4 years and 8 months. How do you compare?
  • ‘Is your life’s work worthy of a memoir’ seems like a good question to start with while evaluating what you are doing?
  • Good advice gotten in the past – identify the good people and go where they are. Who are the folks in this story worth following, for someone in ads?
  • Elliot Schrage was in his fifties and at Facebook as an early employee during this story. What kind of open mind does it take to join a company like nascent-Facebook (madness!) in your fifties – are you cultivating that openness?
  • What did it take for Sheryl to have middle-aged folks follow her to where she was going, subverting their career direction for a then unknown result?
  • How do the number of monetization failures Facebook saw compare to the new kids on the block (Quora, Snapchat, Pinterest), what are the similarities and obvious differences?
  • What finally improved the targeting and delivery of FB ads, if at all anything did?
  • On persuasive messaging – what’s the most effective summary of your work that you can provide?
  • Is there a good summary of the state-of-the-art in retargeting today?
  • The author has an immense grasp of human psychology, some of it obtained in easy-to-figure-out ways e.g. profession based – police folk having strong binary views of people as either good or evil. What are other such easy to spot phenomena?  
  • First party advertiser data is more valuable than any publisher data. Why was this said? Is this still true?
  • Your attention is valuable enough that there are 200 bn+ (yes, with a B) and growing industries competing for it. What have you done to value, protect or harness it?
  • When have you fallen prey to Stockholm syndrome and why?
  • Content Marketing propped up AdGrok. What does this imply for the aspirational individual or startup? Is it generally a waste of time?
  • Author portrays Silicon Valley as a ‘chaos monkey’ for society – where will it succeed the most? Author talks about having the ability to detect human weakness like fresh dog shift on a man’s shoe – how does one safeguard oneself from people like the author?
  • Potential career advice – be a nice person and work with nice folks so one doesn’t have to worry about any of the nastiness the author describes?
  • How does David get Goliath? By employing every possible resource he has skillfully. The author exemplifies this well at places.
  • Author – “half my friends I keep around only to see if my initial suppositions about them and how their lives would develop were right.” How many of your friends think the same way about you?
  • The author shows the dhandho spirit when he calculates “5mn for 3 hires – 2 eng + 1 PM, plus YC bling, plus thought-leadership from the blog isn’t enough”. Interesting how there are “value” calculations underlying the speculative valley?
  • How did Jessica Livingston, YC’s character gatekeeper, pass the author?
  • Boland threw all of FB a curve-ball and managed to buy Atlas over multiple trips to Seattle. How?
  • Spoken for Gokul, why? – “If you are clever than most middle managers, you’ll work at building your personal brand in a way that both augments your prestige and reflects well on the organization.”

Random Observations from the book

  • Zuck thrived on lemon-lime Gatorade. Interesting detail for someone who controlled and affected (mostly negatively) the productivity levels of a few hundred million humans.
  • Even if Like buttons were a good source of monetizable data, it wouldn’t have meant much anyways, since they weren’t exclusive. G+, Twitter, Digg etc were also featured.
  • Reminder that things don’t have to be perfect. This was a company that was close to IPO and was stilled a walled garden, not by choice, and had several monetization nuts pending to crack.
  • Think about how fast the valley moves – the first programmatic media buying startup was bought in 2007. Circa, 2012, we had billions in revenue from that source, as an industry.