Category Archives: Strategy

Bureaucracy, Wokeness, and Sabotage

Originally posted as a Twitter thread on July 29, 2021


In 1944, the Office of Strategic Services, the predecessor of the CIA, produced a (real) guide to “simple sabotage” that spies and ordinary citizens could use to hurt the Axis powers. It’s remarkable to read given some of the Woke things happening within companies today…

The full declassified guide is here (https://www.gutenberg.org/files/26184/page-images/26184-images.pdf). The first 30 pages are devoted to physical sabotage, but page 32 is where the “wait this is really happening in 2021” starts.

If you’re building a startup, read this — don’t let this happen at your company 🙂

“Silicon Valley Does X”

Originally posted as a Twitter thread on January 08, 2019


“Silicon Valley Does X” — what does it mean? It *DOES NOT* (or should not) mean “same thing HQ’d in high cost of living SF.” It means a true first principles approach to re-inventing a stagnant industry, process, and way of thinking.

The philosophical burden of proof is often described as “he/she who brings the claim supplies the proof” (or this, by Carl Sagan: “extraordinary claims require extraordinary evidence.”) This is *very* relevant for “Silicon Valley Does X.”

There is often little evidence for *current* positions (outside of precedent) and consequently “Silicon Valley Does X” is pilloried for bothering to re-examine and re-think orthodoxy.

Any industry trusting random humans to make uniformly optimal decisions with little or no feedback loop — now THAT is an extraordinary claim, requiring extraordinary evidence! So industries like real estate, medicine, investing, lending, etc

Real estate: “this agent knows the best stager and it will make your house sell for more” …proof?

Medicine: “don’t screen for X, too many false positives” (best way to solve that is to…collect more data! look at longitudinal changes!)

Education: “you can’t learn from a computer screen / credentials are everything”…really?

“Silicon Valley Does X” is about challenging assumptions, and often exposing that those assumptions are themselves not evidence based. And guess what? Sometimes the orthodoxy is right…

…but we should be grateful that there are entrepreneurs willing to risk failure and challenge it.

Don’t Just Sell to the CEO!

Originally posted as a Twitter thread on January 13, 2018


There are a broad range of products/services that you CANNOT sell to the CEO or senior exec of a company — too irrelevant to them. You either need to figure out how to position your service against EXISTING top priority to CEO, or you are better off selling “lower” in org

But sell too low, and at a company where the principal-agent problem is at its peak (employees are agents, corporation is the principal), and “saving the company money” or “making the company money” are totally irrelevant.

So for most products and services, you need to find somebody in the “middle” and figure out how to make the agent, not just the ethereal principal, win.

Some of the most valuable companies operate in the “zone of irrelevance” because there is no impetus to switch them out (think: payroll, janitorial services, etc) and costs are not SO high, so not as much margin/competitive pressure

In many cases you need to wait for a fundamental shift to challenge one of these companies, or get very, very creative (and very determined) selling into “the middle.” But it’s ironically much stickier to be in the “zone of irrelevance, yet necessary” for clients

Distribution v Innovation

The battle between every startup and incumbent comes down to whether the startup gets distribution before the incumbent gets innovation.

The TiVo Problem

In 1999, ReplayTV and TiVo invented the Digital Video Recorder (DVR). It was an incredible innovation — allowing you to “pause” live television.

But TiVo had no value without “content” to pause. That content, by and large, was distributed via cable and satellite TV networks.

And because TiVo was separate from your cable box, using it was far from simple. If you wanted your TiVo to “know” what shows were on (and consequently record them), you’d have to have it connect (via modem/phone line — remember, TVs were not placed near phone jacks) to a TiVo server to download them.

Clearly TiVo had an enormous channel opportunity. What if Comcast, Adelphia, Cox, and other large cable companies simply distributed TiVo to their customers? Wouldn’t that be a home run for TiVo and the cable companies — a new service that would delight customers with a massive new revenue stream to boot? And, integrated with the cable box, the TiVo product itself would get better, too.

But — and this is what I call the TiVo problem — that doesn’t normally work out well, and if you look at your cable box today (with a generic DVR function, I would bet, built-in), you know how this story ends.

If you’re TiVo trying to cut a deal with a Comcast, one of the below normally happens:

  1. You partner with Comcast, but Comcast dominates the economics of the deal, in some cases restricting your cooperation with its competitors. (rare to partner)
  2. You sell your whole company to Comcast, but you’re not selling a company, you’re selling an awesome product…and somebody else might have an awesomer product (or a worse one that is deemed better by the technology team at Comcast). Moreover, if you already have commercial deals with Comcast, Adelphia, Cox, et al…, Comcast won’t value your ex-Comcast revenue (because it will disappear upon acquisition by Comcast!), dramatically reducing your independent valuation. (rare to sell)
  3. You get screwed by Comcast. Comcast builds a crappy version of your product, but because they have the distribution, they can and will beat you. (common)

TiVo did not fail, but it became a patent troll of sorts. It has a market cap of less than $1B today, despite having collected more than $1.6B in patent settlement funds from the “Comcasts” of the world.

The Winning Strategy: Go Boring

Given that the common outcome to the “TiVo problem” is getting clobbered by Comcast, how do you deal with this situation?

The answer is often to “go boring and be patient. This was a big mistake I made at TrialPay, which put relevant offers around the payment flow. We built a great product/service/business on top of payments, but it wasn’t core — merchants didn’t start off looking for or needing our product. They started off looking for what I thought was boring, cheap, commoditized payment processing. Going back to the analogy: Consumers want/need Comcast more than they want/need TiVo. Or at the very least, the chronology starts off with Comcast.

In 2006, I thought “Why build a ‘boring’ commodity payment business like Stripe or Square (that did not yet exist), when we could build the lucrative feature missing from all the commoditized payment processors?” We had insanely better unit economics than they did.

But these payment processors had the customer relationships, and they had the starting product that the customer wanted. Eventually we sold TrialPay to Visa, and I think a lot of value will be created for Visa from that deal, but not nearly as much for TrialPay shareholders had we owned the channel.

This is the flaw with looking at Square and Stripe and calling them commodity players. They have the distribution. They have the engineering talent. They can build their own TiVo. It doesn’t mean they will, but their success hinges on their own product and engineering prowess, not on an improbable deal with an oligopoly or utility.

Being Judged on the Present

There are two ways somebody can interpret this video.

-“I’m much better than that kid at golf! [says a 33 year old]. I have a 12 handicap and can outdrive that joker by 200 yards!”

-“Wow, that’s remarkable for somebody of that age…if he continues like that, he could someday win 14 Majors.”

Both assessments are logically correct. But as a young company selling into enterprises, you will often get the first reaction.

In my experience, a lot of larger corporations (and people who work at them) can generally only see the present — the present capabilities, the present revenue (or trajectory), the present limitations. In startups, you need to see the future. Not as a fortuneteller would (impossible) but to judge teams and ideas on their future potential / adjacencies.

There is a natural lesson here for an entrepreneur — which is to beware showing “leanness” of product when interacting with a large company. Saying “we can/will add that later” unfortunately lacks credibility, because large companies are often incapable of building anything quickly, and hence their employees tend to doubt this statement. “Blockers” in the large organization will try to scrap any deal with a “deficient” startup.

The right way to build a typical startup is “lean.” Overbuilding before product-market fit can be catastrophic; building sophisticated management and operational processes before you need them is normally a vast misallocation of resources and actually prevents learning of what the market wants.

But present your lean startup to a large company and you’ll hear “where’s the beef?” When selling a product to a large company, or even selling your OWN company to a large company, you’ll be thoroughly evaluated on the present — which sometimes is good in, say, M&A when you are on an unsustainably high growth rate. The hard part of a company is generally making the whole thing work; it’s not the sophistication of a set of algorithms, but having the whole product perform at scale with an organization that can support it.

I saw this firsthand at TrialPay, which was, at its simplest level, an advertising technology company. An early potential deal with a large company did not materialize because said company was displeased with our optimization systems, even though we could add a better optimization algorithm in a few days (GitHub shows 329 collaborative filtering projects). But we were judged on the present, and if we had the opportunity to do it over, I would have actually invested those few days to look “fatter” — even if it had no impact on our business.

The Danger and Opportunity of the Intermediate Metric

Are social media companies overvalued? The question is not just a matter of revenue multiples (low or high), but rather whether that revenue is actually generating new sales for advertisers. Google convinced the world to believe in the click, Facebook has done the same with the Like, Twitter with the follower, and Pinterest is planning on unveiling the same with the Pin. Creating these “intermediate” metrics between impression and ultimate purchase is a great move to boost revenue, but must stand up to scrutiny as software eats the marketing funnel. For startups seeking to build a valuable advertising business, creating an intermediate metric is crucial, but so is ensuring that that metric holds up to scrutiny.

Let’s rewind a bit, though. Without commerce, without transactions, there would be no advertising. The point of an advertisement is to generate sales. Full stop. Brand building, goodwill, mindshare, buzz, and a lot of other niceties might come about, but even those are meant to eventually lift sales. Without a transaction at the end of the line, advertising has no raison d’être.

The challenge, though, is that it’s often difficult to draw a straight line between “person sees an advertisement” and “person buys a product.” Impression and transaction are the two endpoints of the advertising-commerce lifecycle.

And, the chronological delta between impression and purchase can be wide. A 15-year-old might be bombarded with BMW advertisements for 10 years before she finally pulls the trigger on a fancy, brand-driven car purchase. Deciding to buy Advil vs. Tylenol might take years of external inputs and supermarket trips.

Enter the intermediate metric, which is anything that falls on the continuum from impression to purchase: clicks (the Internet’s first intermediate metric), likes, bookmarks, views, shares, app downloads, recall, followers, retweets, mentions, pins, etc. Intermediate metrics help publishers (e.g., Google, Facebook, Twitter, Yelp, Pinterest, etc.) attempt to show their impact when sales are not readily measurable — either because of chronological disconnect or because the transaction data is not readily accessible. Or, cynically, and in some instances, because there are no downstream sales — making the intermediate metric the best way to obfuscate while purportedly showing performance.

intermediate metric

Intermediate metrics help advertisers show internal and external stakeholders that they’re doing a great job. It’s hard for Clorox’s marketing team to be given an instruction of “sell 20 percent more bleach this quarter and you get a big quarterly bonus!” A national “must wear white to participate” tomato fight might increase sales of Bleach without Clorox lifting a finger. So many advertisers will compensate and reward their teams for the achievement of intermediate metrics.

  • “Your goal for the quarter is to get 10 million Facebook Likes, and to get a 15 percent increase engagement on Twitter.” (This must increase sales, right?)
  • “Twenty percent of your bonus this quarter will be based on getting 100,000 mobile app downloads.” (Mobile is hot and people are using mobile phones everywhere, so it must drive revenue!)

The greatest intermediate metrics allow for the broadest attribution tracking possible (accounting for marginal intent generation), while being somewhat unique to the medium. At scale, Quora might charge for a promoted corporate answer; Gmail might charge for a bolded email; Waze might charge for a “route added.” These would all be intermediate metrics, knowing that none of these actions yield an immediate purchase but hopefully contribute to one. Without an intermediate metric, there would be a publisher-advertiser marketplace failure, since immediate “transaction” tracking would undercount efficacy and cause metrics-driven advertisers to abandon the platform.

The greatest intermediate metrics allow for the broadest attribution tracking possible while being somewhat unique to the medium.

The smartest thing that Google did was charge for the click, not the sale, because it isn’t Google’s fault if your site converts poorly (or if a sale/action is not relevant, as it is for, say, auto research).

The smartest thing that Facebook did was define the like not just as an intermediate metric, but as a quantum of self-worth. Watching Samsung hit 20 million Likes must have made HTC mighty jealous and want to respond accordingly. When I asked a large restaurant chain where they spend most of their money online, the president said “Facebook. We get a lot of likes, and that must be better than not a lot of Likes.” A click — Google’s classic intermediate metric — isn’t too relevant for a restaurant that doesn’t deliver or allow online transactions. Facebook has a potentially broader audience, yet less transactional intent — so ultimately those likes will need to turn into revenue.

As Twitter goes public, it probably needs a stronger intermediate metric that can resonate with the long tail of advertisers. It might not make sense for regular people to “follow” an advertiser like Oreo in the same way they might follow their favorite moviestar, thus making followers a poor metric; in fact, The Bronx Zoo’s Cobra (an actual snake) has more followers than Oreo. The famous Oreo Superbowl tweet was retweeted only 16,000 times. The most retweeted brand advertisement on Twitter (from Nokia) has yet to top 50,000 retweets. Yet perhaps Oreo was seen by millions of people on Twitter, yielding a spike in supermarket sales, and thus followers and retweets — the intermediate metrics with which pundits seem to be measuring Twitter, are the wrong intermediate metrics.

The danger of intermediate metrics is that they feel quantitative — these are numbers, people! — but they might actually be meaningless. Ironically, both parties, advertisers and publishers, often have a vested interest in separating them from sales — for the short term — lest the music stop. Separation allows for “quantifiable metrics” when sales are just too hard to perfectly measure, so advertisers can keep spending and publishers can keep charging.

If a company’s revenue is based on selling questionable intermediate metrics, be cautious — no matter how quickly that revenue is growing. Sometimes metrics are purely about internal vanity and do not last. As an example, “number of app downloads” feels like a key performance indicator, whereas for many companies (Supercuts has an app?!), “apps” make little sense as a paradigm. Depending on how this intermediate metric (app downloads) stands up against actual incremental sales, the whole app download market could suffer. The same goes for many other intermediate metrics. When advertisers start thinking of the intermediate metric as the final action (the R in ROI = achievement of intermediate metric), the market is inflated.

For any company — whether buying traffic or selling it — intermediate metrics are often a crucial strategy in building a broad revenue model and in having a metrics-driven approach to customer acquisition and retention. But it is unwise to divorce the intermediate metric from the final, and crucial, metric of the transaction — to ignore it, or to exaggerate it, is penny wise and pound foolish. Plenty of startups and established industries (television advertising!) will be obliterated when data finally lights the path from impression to transaction and, in some cases, reveals it to be seldom traveled.

Payment Data Is More Valuable Than Payment Fees

We are in the midst of a great revolution in the payments space: anyone with a phone can now accept credit cards; online-to-offline commerce is allowing online payment for offline purchase and significant friction is being removed from the consumer purchase experience thanks to mobile. All of this innovation (read: competition), combined with government intervention, means that payment fees are falling, threatening revenue streams for incumbents and startups alike in the payments space. But a broader opportunity exists: using the data of payments to build a more valuable, more defensible business model, one not dependent on fees. The result will revolutionize offline commerce and online advertising.

Today: It’s All About Fees, and They’re Heading Towards Zero

Payment companies make money by charging fees to “process” a payment from buyer to seller. Square charges 2.75% (or $275/month for volume up to $250K/year). PayPal Here charges 2.7%, as does Intuit GoPayment. Groupon and Amazon are both supposedly working on their own dongles, and prices will continue to fall, especially as these new devices create “one-sided” networks without significant defensibility outside of switching cost and inertia. “Pay with Square” is a potential game changer, as the millions of Square user accounts can ONLY be used with Square. But basic “acceptance of credit cards” is becoming a commodity where prices will keep going down.

Competition between payment companies is only one leg of inevitable downward pricing pressure. Government intervention is the other. Not too long ago, the Australian government decided that payment fees were too high, so now most Australian merchants pay less than .5% for credit card swipes, a fraction of the cost here in the US. The European Union is likely to enact similar legislation. The Durbin Amendment of Dodd-Frank and the $6B+ (pending) Brooklyn Settlement are US-based government and civil attacks on the business of payment fees. Many of these fee-cutting regulations help intermediaries like PayPal and Square short term, by reducing their cost (owed to the Visa/MasterCard infrastructure), but eventually it limits what they can charge, too.

Wherever fees end up, most merchants will still dislike paying them. They are a “cost of doing business” that every merchant has an incentive to bring down. Payment companies generally aren’t delivering new customers; they’re taxing the flow of existing ones. Google effectively charges 20-30% to deliver a customer (if you back out the cost-per-click to percentage of realized sale) to an ecommerce merchant, yet merchants are competing to hand Google more money because each dollar “in” produces more than a dollar “out.” Payment companies charge a fraction of Google, but are often despised (witness the lawsuits and legislation) or treated with promiscuous disrespect.

It comes down to something rather simple: Connecting the bank accounts of buyers and sellers will never be as valuable nor defensible as connecting buyers and sellers. Google delivers customers at the top of the funnel, and payment companies serve the prosaic, but necessary, task of shuffling funds at the end.

Tomorrow: Payment Data Will Revolutionize Commerce & Advertising

As society goes increasingly cashless, payment companies will have a larger business, and a more valuable one, in closing the loop for offline transactions and helping deliver customers. The data they possess is without equal; did somebody buy something? How much did he spend? What did she buy? Paper money cannot be tracked in this manner. In order for Online-to-Offline commerce to take flight, every merchant needs an ability to track online/mobile action to offline purchase, and PayPal Here, Square, GoPayment and others could provide just this for a whole new class of small merchants.

Imagine that Wendy’s, or even a local handyman, wants to advertise on the Internet. What’s the point? What does a click, or an impression, really mean? It’s clear what it means online, since every click can be measured to “action” (e.g., purchase) for an ecommerce company. Who can tell Wendy’s, or the local handyman, if that online advertisement worked?

In an increasingly cashless society, the answer is pretty clear: the payment infrastructure. Tracking that purchase back to the originating source (Google? Yelp? Patch? etc) is known as “closing the loop” and will revolutionize offline commerce and advertising alike.

The million-plus merchants walking around with Square, PayPal Here, and GoPayment dongles want more customers, and these dongles provide a means to “close the loop” and let those merchants acquire more customers, remarket to those customers, understand those customers, and do everything that ecommerce companies have taken for granted for over a decade. Legacy POS systems were poorly integrated and insufficiently verticalized, often requiring a merchant to have separate relationships with every player in the payment chain (hardware vendor, merchant bank, CRM system, etc); moreover, they were priced out of reach of the sole proprietor.

Beyond closing the loop, payment companies can utilize data from existing transactions to generate more transactions. Companies who maintain a direct relationship with the consumer — such as American Express, PayPal, Square, Discover, etc — are in the perfect position to serve as an Amazon recommendation system for “everything.” You bought a tennis racket at Sports Authority? How about tennis lessons with Saul the tennis pro, at a discount thanks to your purchase of a tennis racket, only redeemable with the same payment instrument? You weren’t searching for Saul, and you wouldn’t want an unsolicited email from Saul, but seeing an advertisement for Saul shortly after buying a tennis racket (say, on your purchase receipt) would likely produce a response. It’s a way topreeempt search for a large class of “secondary” purchases (e.g., charcoal after buying a grill; tennis balls after buying a tennis racket, etc), in a “pull” based way.

None of this is to say that the fees charged today are wholly unreasonable and unconscionable; they’re just not long-term defensible as more parties offer the same conduits to existing credit card infrastructure. I have $40 cash and five credit cards in my wallet right now, so any merchant wanting to charge $100 for some widget can either get 97.25% of $100 (if using Square), or $0. That’s an easy decision and shows why things like Square and PayPal Here are hugely beneficial to merchants and consumers alike. But longer term, as those fees continue to compress to the benefit of merchants, the larger business will be in applying the data of payments to the benefit of merchants, consumers, and payment providers alike.

Service as a SKU

(Originally guest-written for TechCrunch)

The biggest ecommerce opportunity today involves taking offline services and offering them for sale online (O2O commerce). The first generation of O2O commerce was driven by discounting,push-based engagements, and artificial scarcity. The still-unfulfilled opportunity in O2O today is tantamount to tacking barcodes onto un-warehousable services by standardizing and normalizing the units being sold, something I call “Service as a SKU.” Just as Amazon figured out how to build the best warehouses and technology in the world for delivering boxes, somebody will do this for “unboxed” services, with customers driven not by discounts or scarcity, but rather by the Internet’s hallmarks of customer experience and convenience. And unlike how “ship stuff in a box” ecommerce seems to be gravitating towards a few winners, Service as a SKU is still a wide open playing field.

The idea is to turn every service, or unit of commerce, into what retailers typically call a SKU (Stock Keeping Unit). Imagine the following as “items” you can buy, and have “delivered,” with a simple click or tap:

“1 Unit of Plumber-Fixes-Your-Leaking-Toilet”
“1 Unit of Dentist Fixes Your Crown”
“1 Unit of 12-Inch Hole-in-Roof-Is-Fixed”
“1 Unit of Piano Tuner Tunes Your Piano”
“1 Unit of Set Up a Home WiFi Network”

Groupon and LivingSocial, early leaders in O2O commerce, started a wave I wrote about a few years ago, but have historically focused on discounting and creating demand by artificial time or quantity scarcity. There are two main problems here:
-Adverse selection: Groupon et al tend to attract customers looking for deals. This is not what Amazon does, and not how most consumers shop for necessities (e.g., fix my toilet!).
–Push v Pull: Groupon et al tend to rely on “push” (e.g., email) to drive a tremendous amount of sales. Unlike Google, eBay, Yelp, or Amazon, people don’t tend to go to Groupon “unprompted.”

To successfully create a SKU for every service, you need to normalize both the service provider (price/quality) and the service being rendered. It’s more like buying produce than buying something mass-produced in a factory. Or, perhaps more accurately, it’s more like booking a hotel reservation, where the rooms are anything but identical, there exist varying degrees of quality, but there are also quite a few commonalities.

The company that pulls this off will need to have the following:

-A seamless scheduling system, deployed at various service providers, to allow real-time inventory management. OpenTable does this for restaurants, and hence can provide a marketplace for “tables” at opentable.com. You can’t sell boxes without knowing how many items are in your warehouse; you can’t SKU-ify a Service without knowing how many hours are available.

-A trusted ratings system to allow for normalization of services and parsing of consumer feedback. How do I compare a $100 “fix my toilet” plumber to a $175 “fix my toilet” plumber? Ideally this will work like hotels: every service provider has a “star rating” and an associated cost. Hotel rooms are reasonably similar; consumers can choose between a 5 star hotel or a 2 star hotel, and even different star levels have significant variance. Yelp and Angie’s List have tremendous assets in their community-based feedback, although payment companies like PayPal and Square have perhaps an even better potential asset on their hands (chargeback rates are a good proxy for merchant quality, every completed transaction can solicit quality feedback and not just from aggrieved/fanatical customers, etc).

-A no-discounts, no-push site. OpenTable gets people looking for restaurants, and needs neither emails nor discounts to make that happen. Yelp, Google, eBay, Angie’s List, and Amazon are all contenders as they all have consumers “coming back” unprompted. If the product and site are sufficiently convenient, this often happens organically; having a well-designed and convenient search, shopping, payments, and redemption experience avoids the need for push marketing.

-Relationships with offline service providers. Despite the flash nature of Groupon and LivingSocial, their merchant relationships are significant. Yelp has virtually every business profiled but perhaps not every business engaged in an economic relationship.

It’s important to note that Service-as-a-SKU is not lead generation for offline services, nor is it just a glorified scheduling platform. “Leadgen” has been around since the beginning of the internet, but there is no standardization or normalization, not to mention the convenience of “one-click” purchase. There are leadgen services for housing relocation, laser eye surgery, insurance, etc, but none let you actually make a purchase online. The hard part is in “normalizing” to create a single “service item” that can be scheduled, paid for, and “delivered” with a mouse click or smartphone tap. As an example, Uber has done this for black cars, and EXEC is fixing hourly prices and limiting SKUs to low-wage labor services.

At 8:01 AM on June 26, 1974, a shopper named Clyde Dawson bought the first item — a 10-pack of Juicy Fruit gum — to ever be scanned with a UPC (universal product code). Today, barcodes are a part of every mass-market product bought and sold throughout the world. You won’t see plumbers, dentists, limo drivers, or gardeners walking around with UPCs on their backs, but we are poised for another shopping revolution of equal magnitude.