The Bill Gurley Chronicles: Part I

The Bill Gurley Chronicles: Part I

By Alex of the Macro Ops Substack

What if there was a way to distill all the knowledge that someone’s written over the last 25 years into one, easy-to-read document? And what if that person was a famous venture capital investor known for betting big on companies like Uber, Snapchat, Twitter, Discord, Dropbox, Instagram, and Zillow (to name a few)? 

Well, that’s what I’ve done with Bill Gurley’s blog Above The Crowd

Gurley is a legendary venture capital investor and partner at Benchmark Capital. His blog oozes valuable insights on VC investing, valuations, growth, and marketplace businesses. 

This document is a one-stop-shop summary of every blog post Gurley’s ever written. 

Here’s how it’ll look. Each summary will contain the following: 

Date, title, and link to blog post
One paragraph summary
My favorite quote

This piece allows anyone to absorb all of Gurley’s knowledge bombs in the fraction of the time it took me to do it. I hope this piece brings you as much value as it did to me. 

Let’s get after it.

Years: 1996 -1999

October 21, 1996: Backhoes Don’t Obey Moore’s Law: A Story Of Convergence (Link)

Summary: The backhoe improved at an annual rate of 4.4%, falling short of Moore’s Law equivalent improvement of 59.7%. Computers are dependent on telecom to deliver the internet. But telecom is dependent on Moore’s Law failing-backhoes. This means we’re building computer-centric solutions to Internet-based problems without addressing the core problem: laying fiber cables with obsolete backhoes. 

Favorite Quote: Backhoe dependency is really just the simple side of our message. It is our impression that the majority of the players in the computer industry bring a “computer centric viewpoint” (CCV) when analyzing the issues that exist with the Internet. This computer-centric view could prove hazardous. Not only will it lead to disappointed expectations, but it may also lead to a less than accurate vision of the future.”

April 20, 1998: How To Succeed In Advertising (Link)

Summary: There are three reasons why success-based advertising wins the day on the internet: 

Customers want it: Advertisers can quickly see if their programs work and easily predict margins using COGS + “bounty fee” model
Solves excess inventory problems: The best way to reduce inventory is through direct-selling, success-based advertising (think 1-800 ads on cable TV)
Unsold Ad-Space on Internet: As internet population increases, it reduces the CPM per pageview. This causes an inventory glut of internet space and a perfect place for performance-based ads

Also, you can use a DCF to find the LTV of a customer. It’s simply: $ in FCF per customer/year divided by the discount rate. 

Favorite Quote: “The lifetime value of the customer is equal to the future cash flows (not revenue!) expected over the life cycle of the customer, discounted back by a reasonable discount rate. What we are really doing is treating the customer acquisition as an investment and the lifetime cash flows of the customer as the yield on that investment.”

May 5, 1998: Standards: Open For Business (Link)

Summary: Open standards is the idea that companies in an industry operate within a specified set of rules (or parameters). Think of printers and PCs. It makes sense for all PCs and printers to be compatible with one another. This reduces time to market for most products. The issue, however, arises when open standards are applied to tech-heavy businesses without distribution advantages. Software is a perfect example. Distribution is effortless, so the only way to gain an edge in open standards is through sales teams and technical support. And who has the lead in that? Large companies. 

Favorite Quote: Theoretically, you could have a better sales force or better service and support, but these are not typically assets that small innovative companies possess. This means that competing with a completely “open” strategy would offer very little room for differentiation, and there is almost a necessity to have some closed proprietary advantage. It is difficult to criticize companies for trying to innovate in a proprietary manner. After all, survival is instinctive.”

August 17, 1998: Internet Investors: Beware Of The Proxy Valuation (Link

Summary: Investors use proxy valuations to value companies without hard free cash flows (NOPAT – capex). Proxy valuations come in all shapes and sizes, including: P/Revenues, Market Cap / Subscriber, Market Cap / Unique Page View, etc. While proxy valuations are better than blindly picking stocks — it’s not the end goal. Businesses must generate cash flow to survive. This brings us to a few dangers of proxy valuations: 

Symmetry Risk: Not all proxies are created equal (e.g., Price/Sub not the same as Price/Page View)

Assumption Risk: A customer’s value changes. We can’t assume a company will generate $X from each customer over its lifetime

Arbitrage Risk: Companies IPO based on # of customers, revenue stats or subscribers … not cash flows or profitability

Favorite Quote: Another reason to be skeptical of proxy valuations is arbitrage. If Wall Street comes to believe that customers, or visitors, or page views, or even revenues are uniquely valuable (regardless of profitability), than entrepreneurs are likely to rush to market with companies that can achieve these targets quite handily, but may have little chance at producing real value in terms of cash flow. With no focus on costs, it is easy to reach non-financial targets. This is the great thing about cash flow-based valuation, it’s hard to sweep costs under the rug.”

October 16, 1998: The Continued Evolution Of Advertising Or How To Succeed In Advertising Part II (Link

Summary: Traditional advertising is squeezed out of the value chain as ad buyers recognize the difference between pay-per-impression and pay-per-click through. Further, the invention of TiVO (recording shows & content) increased demand for a direct-to-consumer content delivery system. Ideas like pay-per-view TV were born from the idea that you can cut the middleman (networks & advertisers) and directly charge your customer. 

Favorite Quote:  “While this is possible, it ignores the fact that the viewer now has a choice, and that these devices will allow the content provider to push content directly to the end-user, potentially on a pay-per-view basis. If the consumer is willing to pay $5 to watch Seinfeld commercial-free, why should they be denied?”

July 12, 1999: The Rising Impact Of Open Source (Link

Summary: There are six things to know about open source (OS) code. One, open source works. Two, OS can produce business-quality code. Three, OS business models are emerging. Four, OS is a tough competitor (hard to beat free!). Five, OS models are entering the content generation space. Six, OS may be as helpful as a defensive mechanism than an offensive weapon. 

Favorite Quote: Open source as a production model should be appreciated in the same light as Henry Ford’s assembly line or Demming’s Just-In-Time manufacturing process. By taking advantage of the electronic communication medium of the Internet as well as the distributed skills of its volunteers, the open-source community has uncovered a leveraged development methodology that is faster and produces more reliable code than traditional internal development. You can pan it, doubt it, or ignore it, but you are unlikely to stop it. Open source is here to stay.”

October 18, 1999: The Rising Importance Of The Great Art Of Storytelling (Link)

Summary: Storytelling is one of the most underappreciated business skills. Bill Gates admired a man (Craig McCaw) because he was able to convince investors to invest in a capital-heavy infrastructure business. McCaw created new (proxy) valuations to sell the story the company was trying to deliver. Storytelling also gets a bad rap because it’s associated with “hype” — overpromising and under delivering. Recognizing a good story from a bad one helps investors avoid dreams and invest in the future. 

Favorite Quote: As public market investors begin to evaluate younger and younger companies, their valuation tools become limited to subjective notions such as quality of the team and the uniqueness and boldness of the idea.  In other words, if there isn’t enough proof that a business already exists, then they must make a judgment as to whether one will.”

Years: 2000 – 2002

March 6, 2000: The Most Powerful Internet Metric Of All (Link) 

Summary: Conversion rate is the most important metric for internet-based companies. Why? Conversion rate captures total user engagement. It also boasts high leverage. Here’s the big idea: as conversion increases, revenue rises and marketing costs decline. There are five things that affect conversion rate: 1) user interface, 2) performance (slow v. fast), 3) convenience, 4) effective advertising and 5) word of mouth. 

Favorite Quote: “Let’s assume you spend $10,000 to drive 5,000 people to your site, and your conversion rate is 2 percent. This means that 100 transactions cost you $10,000, or $100 per transaction. Now let’s assume your conversion rate rises to 4 percent. The same $10,000 buys you 200 transactions at a cost of $50 per transaction. An 8 percent rate gives you 400 transactions at a cost of $25 per transaction. As conversion rate goes up, revenue rises while marketing costs as a percentage of sales fall – that’s leverage.”

April 17, 2000: Can Napster Be Stopped? NO! (Link)

Summary: Napster paved the way for the free digital music we enjoy today. Here’s how. The software leveraged each user’s computer files and shared music freely between PC devices, not the internet. Napster’s popularity grew, and within six months the software had 9 million users. It took AOL 12 years to get to that figure. There are two important lessons from Napster: 1) the power of community-building and 2) information wants to be free. Connect those two lessons and you have an incredible community-based business. 

Favorite Quote: Remember that the amount of bits it takes to represent high-quality audio is finite. Until the past few years, the amount of space on a hard drive, as well as the bandwidth required to transfer an MP3 file, was prohibitive for widespread usage. However, both bandwidth and storage space are susceptible to Moore’s Law. This means that within six years, the amount of drive space or bandwidth needed to trade high-quality music will be unnoticeably negligible. Emailing an entire album of music to a friend will be no different than forwarding a Microsoft Word document today.”

May 15, 2000: A Return To Demand-Driven Capital (Link)

Summary: There is a huge difference between demand-driven and supply-driven start-ups. Demand-driven start-ups see an area of the market where a need doesn’t have a solution. Then, they create a company to fill that need. Supply-driven start-ups conceive companies on the idea that one day consumers will need their solutions to problems that might not exist yet. The intellectual satisfaction of creating solutions is more appealing than bottom-fishing for long-standing consumer problems. At the end of the day, it’s better to start (and invest in) demand-driven businesses.  

Favorite Quote (emphasis mine): I suspect what’s at work is that Plato-esque idea that creation is much more intellectually appealing than combing the earth for steadfast problems to solve. But keep this in mind: Even a sexy Internet company like eBay was born of demand instead of supply. Founder Pierre Omidyar’s girlfriend wanted a place to trade Pez dispensers online. The company rose after the market voted. I suspect that entrepreneurs and venture capitalists alike would be well-served to return to the boring, but perhaps more successful, world of demand-driven capitalism.”

June 12, 2000: Like It Or Not, Every Startup Is Now Global (Link)

Summary: The rising prevalence of start-up infrastructure overseas poses a threat to US-based start-up companies. US start-ups face two main threats: 1) imitation from overseas competitors and 2) expanding too quickly. Faced with growing competition, US companies might go global before establishing a solid footprint on their home turf. This has devastating consequences as they’ll burn more cash and lose focus on their core markets. There are three solutions: 1) Joint ventures, 2) acquisitions and 3) start-up your own global market.

Favorite Quote: “Ironically, the same courage that leads a start-up to look overseas could cause failure if the company moves too quickly and aggressively or assumes it can get by without local partners. When considering such alternatives, it is important to keep one fact in mind: 50 percent of something is worth a lot more than 100 percent of nothing.”

July 10, 2000: The End Of CPM (Link)

Summary: Echoing Gurley’s 1998 article, 2000 saw the rise of performance-based advertising. The catalyst for such rapid adoption was the outflow of capital to money-losing internet companies. With tight budgets, companies needed ad campaigns that worked. The other catalyst is the proliferation of customer behavior data on company websites. Management can see exactly who is on their site, how long they stay, and if they convert. 

Favorite Quote: “Of course, the biggest catalyst in the past 90 days has been the closing of the IPO market and the subsequent focus in the start-up world on profits and cost controls. This abrupt and refreshing change is a major accelerator that immediately tightens the belt of most Internet marketing departments and targets their spending on the most efficient forms of advertising they can find. Gone are the days when companies indiscriminately bought the “anchor tenancy” on the favorite portal just as a branding event.”

February 19, 2001: The Next Big Thing: 802.11b? (Link)

Summary: WiFi will revolutionize the way we conduct business and where we choose to interact online. While there are critics of the technology, there is no denying its potential to reach critical mass and spread nationwide. The real catalyst for WiFi’s adoption is the move from corporate offices to homes, then to public places like colleges. 

Favorite Quote: “Like other dislocating technologies, Wi-Fi is now working its way from the office into the home. While home networks are still in their infancy, the benefits of a wireless architecture may be even higher than at the office. Who has the capability to rewire their whole house? And although less obvious, the interest in aesthetics at home heightens the benefit of not stringing wires halfway across the room. Also, as we integrate the home entertainment center with the PC, a wireless link is particularly appropriate. Lastly, what if I could carry my laptop home from work, lay it on the kitchen counter and be online instantly? You can today with Wi-Fi.”

June 25, 2001: The Smartest Price War Ever (Link)

Summary: Dell engaged in the smartest price war ever. Their business model, which focused on just-in-time inventory, resulted in positive cash-flows even under income statement compressions. Through five-day inventory, 59-day average payables and 30 days receivables, Dell generated a negative cash conversion cycle. This allowed them to cut prices while their competitors’ models couldn’t allow such maneuvers. Competitors were forced into a lose-lose situation (cut prices and lose margin or not participate and lose market share). 

Favorite Quote: “Much has been written about Dell’s direct model, which removes the middleman, along with his margin, from the sales process. And others have noted that Dell’s incredible five days of inventory allow it to pass on component price declines faster than anyone else in the industry. But perhaps the unique aspect of Dell’s business advantage is its negative cash conversion cycle. Because it keeps only five days of inventories, manages receivables to 30 days, and pushes payables out to 59 days, the Dell model will generate cash—even if the company were to report no profit whatsoever.”

August 13, 2001: Bye, Bye, Bluetooth (Link

Summary: WiFi will eliminate the need for Bluetooth. In its simplest explanation, WiFi works for the internet model whereas Bluetooth works for walkie-talkies. That’s a huge difference. It also shows the power of companies that can quickly cut products/ideas that fail despite tremendous sunken-costs. Bluetooth was a three-year push designed to revolutionize the way computers and devices interacted. Then WiFi came along. Those that quit Bluetooth early not only had a head start on their stubborn competition, they also saved thousands in wasted R&D. 

Favorite Quote: “Even without competition from Wi-Fi, Bluetooth would have major challenges. That’s because the very concept of a cable replacement like Bluetooth is flawed. In a world where every device is connected to a single network (read: Internet), there is no need to connect individual devices on an ad hoc basis. Consider this – a walkie-talkie is a device that supports communication directly between two nodes. A cell phone is a device that supports communications between “any” two nodes because they are all connected to a common network and they all have unique addresses. Blue-tooth is to a walkie-talkie whereas 802.11 connected to the Internet is more analogous to the cell-phone model.”

October 1, 2001: Tapping The Internet (Link)

Summary: After the terrorist attacks on 9/11, many government officials sprang forward, calling for increased surveillance and backdoors on many privacy networks. The main argument was that these terrorists had access to high level technology and software. The reality was less cinematic. Osama Bin Laden used Steganography to spread information amongst his followers. Unfortunately for senators, Steganography uses every day files like images to transmit messages. So it’s not as simple as allowing backdoor access to private channels. 

Favorite Quote: “The government should not give up on computer surveillance. In fact, as a tool that is used to track down a particular offender after isolation and identification, these technologies can be extremely effective. However, we should not be unrealistic about what type of “magic” spy technologies are at our disposal. We are only going to spend a lot of money, waste a lot of time, and create a false sense of security.”

October 29, 2001: When It Comes To Pricing Software, The Greener Grass Is Hard To Find (Link

Summary: The internet allowed software companies to price their product as a subscription service (SaaS) right when companies were facing hardship. The SaaS model eliminates the high-dollar upfront sales pitch and allows the company to generate predictable revenue during the year. However, stretching revenues over months (not upfront) increases short-term operating losses. Those that can withstand the short-term negativity should reap the long-term rewards of the SaaS model. 

Favorite Quote: About this same time, the rise of the Internet gave birth to the idea of an ASP – a model where software would be delivered as a service over the web, and customers would “subscribe” to the software. Analysts raved at the genius of the idea. With this model, the customer would pay an incremental fee each month, therefore eliminating the “start from zero” sales game inherent in the software model. Assuming no loss of customers, the revenue from last quarter is already booked for this quarter – all new sales theoretically represent incremental growth.”

April 3, 2002: It’s Time To Put A Stop To Spam (Link)

Summary: Hackers and spammers always find a way to exploit new technology. Spammers were so bad in 2002 that Gurley had to write about it. The problem lies in time spent deleting spam messages. Time that should garner more productive activities like business. This creates incentives for start-ups to solve such problems. But, the biggest risk facing these spam software companies is a false positive. False positives could delete an email that was legit — potentially costing companies millions in lost revenues. 

Favorite Quote: “Email is fast becoming the preferred communication medium for many corporations. Moreover, email is also the baseline for many new cross-company workflow applications. We simply cannot allow a bunch of Viagra ads to put a dent in the evolution of the global economy.”

Years: 2003 – 2005

January 6, 2003: 802.11 & Cellular: Competitor Or Complement? (Link)

Summary: Gurley explains that WiFi is to 3G as the personal computer was to the mainframe. By understanding the mainframe/personal computing industry, you could “see” the future of WiFi and cellular data. No-one envisioned personal computers operating hundreds of websites or ERP systems. Yet technologists built products on top of the standardized mainframe. WiFi is no different. At the time, a ~$30 WiFi radio and a Pringles can could get you high-speed connectivity at a 10 mile distance. To Gurley, WiFi and cellular data are complementary. Like chips and salsa, with WiFi stealing incremental market opportunities over time. 

Favorite Quote:This exact thing is currently happening with 802.11. This tiny, and increasingly inexpensive radio is already shockingly versatile. The same $30 radio can be used to serve wireless connectivity in your office, connect both you PCs and your multimedia in your home, and provide coverage to a police force across an entire downtown area. Add a Pringles can as a directional antenna (no kidding!), and this $30 radio is capable of providing high-speed line-of-sight connectivity at a distance of 10 miles. In fact, the majority of the volume in the line-of-sight fixed wireless market has shifted almost entirely to low-cost 802.11 radios.”

February 10, 2003: Software In A Box: The Comeback Of The Hardware Based Business Model (Link)

Summary: Software companies might pitch their product inside a hardware offering, going against conventional Silicon-Valley logic. Gurley notes that while pure software businesses generate higher margins with lower capital intensity, it comes at a cost: software-only business models are harder to execute. Gurley saw the software-in-a-box path as the easier option because it addressed seven key issues: 

Development complexity/Quality Assurance
Reliability/Stability/Customer Service

Favorite Quote: “There is a silver lining. The industry has changed in ways that improve the “business model” elements of selling hardware. The key driver is the standardization and general availability of hardware components, particularly those used in generic Intel-based 1U servers. As a result, the hardware is not a proprietary design, but rather a type of packaging. Think of it as an alternative to a cardboard box.”

March 18, 2003: Pay Attention To BPM (Link)

Summary: Business Process Management, or BPM, will change all of business. Gurley was so excited about BPM because it solved four main sticking points in an enterprise’s day-to-day process: 

Codifying current processes

Automating execution

Monitoring current performance

Making on-the-fly changes to improve current processes

For the first time, employees could “hand off” applications to other employees inside the firm. This allowed for faster improvement and implementation of better processes throughout the organization. 

Favorite Quote: “Of course, the real winners here will be customers that embrace BPM to further automate, enhance, streamline, and optimize their core business processes. These processes are the core intellectual property of most businesses. And just as the level of competition in manufacturing increased with JIT, the level of competition with respect to non-manufacturing business processes will increase with BPM. Companies that lead will succeed.”

April 23, 2003: Dot-Com Double Take (Link)

Summary: Many investors threw all “Internet Based” businesses out with the bathwater during the Dot-Com bubble. According to Gurley, that was clearly the wrong approach. Underneath the grime of pump-and-dump schemes, the Dot-com Bubble created durable, profitable businesses (like AMZN, GOOGL, Verisign, etc.). 

Gurley saw four reasons why these left-for-dead Internet companies worked: 

They weren’t bad ideas.

Rationality set in first. 

Quick capacity reduction. 

Internet usage growth is systematic, not cyclical. 

Favorite Quote: Consumer spending may be down 5%, but online spending is still such a small percentage of overall consumer spending that growth results from the continued increase in online usage. With IT expenditures already at 50% of corporate capital expenditures, the opposite is true for traditional information technology spending.”

June 10, 2003: In Search Of The Perfect Business Model: Increasing Marginal Utility (Link)

Summary: Increased marginal utility (IMU) is the holy grail of capitalism. It’s also easier than ever to attempt IMU in our internet-based world. IMU means that for each incremental time a customer uses your product/service, they receive more value than the previous time they used it. You don’t need switching costs in an increasing marginal utility ecosystem. Why? Because switching costs lock in a customer in an “I win, you lose” scenario. In an IMU world, the customer feels left out if they don’t use your product or service. The goal: find companies that produce increased marginal utility for their customers. 

Favorite Quote: “This may be the nirvana of capitalism – increased marginal customer utility. Imagine the customer finding more value with each incremental use. Some may suggest that this concept already exists in the form of volume discounts. However, this offers a vendor no real competitive advantage, as all of its competitors are likely to offer the same discount to large purchasers. Others may feel this is just a buffed-up version of “high switching costs.” On the contrary, increased marginal customer utility preempts the need to impose switching costs, which can be seen as “trapping” or “tricking” the customer. Instead, the customer who abandons increasing marginal customer utility would experience ‘switching loss.’”

July 16, 2003: The Comeback Of The Mobile Internet (Link

Summary: Mobile internet flourished thanks to the growth in cell phones. With cell phones, billions of people could access the internet, purchase items, and engage in content. In fact, cell phones will dominate the war against PCs. There are a few reasons Gurley believes this claim. First, cell phones are everywhere. Billions of people have them. Second, they’re portable, allowing users to kill time on apps and games. Third, people are more likely to purchase over the internet on their phones. Finally, IP addresses make it easy for billions of users to connect simultaneously. 

Favorite Quote: “While a more carrier-friendly split may be good for the carrier’s bottom line, it could drive content providers to more generous carriers, rendering the greedy carriers’ offerings less attractive to users. Interestingly, one of the most successful content platforms, Japan’s DoCoMo service, is built around an extremely generous 91%-9% split, which is more favorable than all U.S. and European carriers’ current deals. The carriers are all walking a fine line between driving revenues and creating a viable ecosystem to encourage publishers to invest in content.”

August 23, 2003: Much Ado About Options (Link)

Summary: People worry too much about stock options and their impact on bottom-line earnings. Yes, there are certain instances where stock options balloon to large percentages of pre-tax earnings. But those are few and far between. Also, it doesn’t really matter whether a company grants options or restricted stock. Both offer employees skin in the game, and both cost the company roughly equal equity. That said, restricted stock incentivizes value retention. Whereas options incentivize value creation. 

Favorite Quote: In addition, restricted stock grants could encourage a form of widespread corporate conservatism. If an executive is granted $2MM worth of stock, he or she might have incentive to help increase the price to say $2.3MM, or 15%. That said, the incremental $300K is peanuts when it comes to protecting the value of the $2MM already on the table. There is a huge difference between corporate sustainability and corporate value creation. GM traded at $38 per share in 1994, and since it is $38 per share today, it has “sustained” value for the past nine years. Is this the type of behavior we hope to encourage?”

October 7, 2003: Beware The Digital Hand (Link

Summary: Digitization is great for consumers, but awful for consumer electronics producers. Semiconductors make electronics faster, cheaper and more powerful. Who reaps the rewards? The semiconductor industry. That’s where differentiation happens. Consumer electronics (CE) companies commoditize, forced to differentiate another way: supply chain. The CE leaders will be the ones with the shortest distance between their product and the customer. 

Favorite Quote: “Digitization is creeping its way across the entire consumer electronics industry, as we slowly remove analog media and components from our lives. While this is good news for consumers who benefit from the low prices that the digital hand ensures, the quid pro quo for businesses is brutal competition.”

December 18, 2003: Cleaning Up After The Ninth Circuit In An Attempt To Save The Internet (Link

Summary: A regulated internet disproportionately hurts these four groups: consumers, IT businesses, American competitiveness, and RBOCs. Regulation hurts consumers in the form of higher prices to compensate for increased taxes. IT businesses hurt because if you slow the speed of internet adoption, you remove the runway for the IT industry. This translates into competitiveness issues as places like South Korea see 60%+ internet adoption. Finally, RBOC’s hurt because it would be a repeat of DSL regulations, which slashed growth and prompted the switch to cable modems. 

Favorite Quote: We should all know by now that rather than increasing competition, regulation typically reinforces monopolies and oligopolies. Startups will not and cannot prevail in heavily regulated industries. They lack the required resources and capital to manage fifty different utility commissions on a hundred different regulatory issues. For this same reason, you will never see a startup deliver an automobile in the U.S. as the regulatory red tape swamps all efforts. Increased regulation will do nothing more than ensure that new competitors and innovative solutions are permanently locked out of the market.”

* * *

That’s about where Substack cuts us off! Stay tuned next week for the next part of our Bill Gurley Chronicles Series!

Tyler Durden
Sun, 06/12/2022 – 15:30

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