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The Bill Gurley Chronicles: Part 3

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 past two to the one-stop-shop summary of every blog post Gurley’s ever written, part 1 can be found here and part 2 is here.

May 29, 2009: Will Apple Make An Actual Television? Makes Sense To Me (Link)

Summary: The thought of Apple (AAPL) making a physical TV seems wild. Yet according to Gurley, there are six reasons why this wasn’t such a farfetched concept. First, TV is a commodity business and AAPL excels at charging a premium on an otherwise commoditized product (i.e., MP3 players). Second, AAPL already makes large iPads that people love. Creating an even larger piece that AAPL fanboys would love to hang in their home makes sense. Third, TV will add an internet stack and AAPL might have to make their own hardware to support that. Fourth, It’s a huge market (Gurley estimates ~$2.5B in sales). Fifth, the TV would integrate with the Apple iOS, creating a seamless experience. Finally, AAPL has the retail footprint to sell its physical TVs. 

Favorite Quote: For Apple, the fact that the TV business has become a commodity business will not be a roadblock. In PCs and MP3 players, they have proven they can charge a huge premium and extract enviable gross margins even where others have starved.”

June 2, 2009: A Really Interesting Online Education Company In Korea: Megastudy (Link)

Summary: Education feels like one of the last industries not hit with the capitalist bug. Maybe it’s the massive bureaucratic red tape or the incumbent teacher’s union. Regardless, Gurley showcases a South Korean company that’s turning to capitalism to give teachers better pay and students better education. The company is Megastudy. There are a few reasons Gurley loves the business: 

  • Subscription service for each course
  • Easily scalable for teachers as they teach once to as many students as they want
  • Teachers get ~23% of revenue from the course sales (this created $1M for teachers)
  • Incentives hinge on how engaging, productive and informative teachers are to students

Gurley said he invested in a company trying to do something similar in the US, Grockit. The company was eventually bought by Kaplan in 2013. 

Favorite Quote: Many here argue that U.S. teachers are underpaid, so in that sense it should be a huge welcome.  That said, I don’t think any teacher union in the U.S. would support the “eat what you kill” business model in use at Megastudy.”  

June 8, 2009: Amazon’s AWS Strategy Becomes Clearer Every Day (Link)

Summary: Amazon’s strategy when they entered the cloud business was simple: offer the lowest-cost cloud infrastructure and obsess about the customer. The second part is reminiscent of their retail business, and a meme from an old Jeff Bezos video. This comfortability in running a low-margin business allowed AMZN to move first in the space before IBM, MSFT, etc. Second, Gurley notes that no other cloud company listens to their customers like AMZN. It’s also fascinating to see how AMZN grew their cloud business: via rogue/small developers. While most saw this as a bug, insiders knew that’s exactly how you want to grow that business (i.e., bottoms-up growth). 

Favorite Quote: Many in the IT world are quick to point out that its only small businesses and rouge developers in large organizations are using AWS.  This is exactly how these markets develop.  Amazon is simply selling to the innovators and early adopters in the market — the exact customers that are prescribed in Crossing the Chasm. These are the customers that others will follow, and by the time the laggards come into the market, the game will be over.”

July 15, 2009: Bill Gurley On The “Free” Business Model (Link)

Summary: The freemium business model is one where a company offers a product or service for free (or marginally zero cost) to its customers. On one hand, it’s a great way to disrupt an industry, and a “simple form of the innovator’s dilemma strategy.” Yet Mark Cuban and Malcolm Gladwell disagree with the “panacea” of the freemium model. The bottom line is that if you have highly differentiated content, you should charge for it. 

Favorite Quote: “Basically, there is always a cost to delivery, even if it’s really low on a marginal basis, and in volume, it can get quite expensive on the cost side. He also, appropriately highlights that “Free” is not a panacea of a business model. It doesn’t always work.”

July 27, 2009: I Do Not Believe That Zappos Was “Forced” To Sell (Link)

Summary: The hot rumor in July of 2009 was that Zappos was forced to sell to Amazon by Sequoia Fund (an investor in Zappos). Gurley thinks that wasn’t true for three main reasons: 

  1. Tony (Zappos CEO) could have withheld his vote at the BOD level, or even dissented. 

  2. For the exact same reason, Tony could’ve withheld a positive shareholder vote from his common shares. 

  3. Tony could have informed Jeff Bezos that he does not want to sell. 

Favorite Quote: Personally, I think it’s a great match and a great outcome for both companies.  They have a shared mission and very similar service-oriented customer brand.”

July 29, 2009: Counterpoint To Calacanis On Yahoo-Microsoft Deal (Link)

Summary: Obsessing over what competing businesses are doing is a sure way to destroy economic value. Nowhere is this best seen than when companies tried to mimic Google’s offensive search-based ad playbook. Gurley reasons that “laying chase” to an increasing returns business (like GOOGL ad network) is a waste of time. On the other hand, AMZN is a great example of a company recognizing the desire to clone, and doing the opposite. Instead of plunging into search and ad-based models, AMZN created AWS where they can control the pace of the game. 

Favorite Quote: “For all their efforts, it’s unclear to me that Yahoo or Microsoft have created any positive equity value whatsoever based on their obsession with Google. I do not have access to the specific numbers, but from a cash flow perspective it would be easy to imagine that its a net negative for both of them.” 

August 4, 2009: More IPO News, Ancestry.Com Files S-1 (Link)

Summary: According to journalists, 2009 was a doom-and-gloom year for IPOs. Gurley’s take sounded much different. There were five IPOs during the year (up until this post) and all of them were doing well. At the same time, Ancestry.com filed their S-1. The company opened around $13/share in 2009. They were later bought by a PE firm for $32/share. Not a bad return for the pessimistic IPO market of 2009!

Favorite Quote: I wonder how many successful IPO’s we need before people will stop saying the window is closed.  Looks perfectly open to me.”

August 20, 2009: A Real Time Free Vs Fee Example: Rosetta Stone Vs. LiveMocha (Link)

Summary: LiveMocha is a free online language learning website with an incredible community of learners and contributors. These contributors often create courses and open the site to new languages for free. Of course, LiveMocha isn’t guaranteed a seat at the profitability table anytime soon. The company doesn’t have a clear monetization strategy, and we don’t know how sticky the consumer brand is compared to the household name, Rosetta Stone. 

Favorite Quote: If you read our previous thoughts on the free business model, we made one key point. Free is not necessarily a game plan, or a guaranteed model for success, but rather a market reality. Someone may be able to do what you do for free.  Does it guarantee they will be wildly successful? No, but it still may be a massive threat.  Microeconomics is not a zero-sum game. It’s perfectly reasonable for all the players in a market to not generate excessive (or any) profits.”

August 24, 2009: What Is Really Happening To The Venture Capital Industry? (Link)

Summary: The VC industry was under heavy pressure in 2009 due to underperformance and bloating AUMs. Gurley suggested the problem stemmed not from VC itself, but from its source of funds. VC firms receive most of their capital from pensions, endowments, and foundations. These are the largest pools of capital in the world. Over time, most of these pools of capital have increased their allocation to VC-based alternative investments. As such, the size of the VC industry ebbs and flows with how much money institutions decide to invest. 

Favorite Quote: “There are many reasons to believe that a reduction in the size of the VC industry will be healthy for the industry overall and should lead to above average returns in the future. This is not simply because less supply of dollars will give VCs more pricing leverage. We have seen over and over again how excess capital can lead to crowded emerging markets with as many as 5-6 VC backed competitors. Reducing this to 2-3 players will result in less cutthroat behavior and much healthier returns for all companies and entrepreneurs in the market. Additionally, at a stabilized market size of well over $15B a year, there should be plenty of capital to fund the next Microsoft, Ebay, or Google.” 

September 29, 2009: Want To Know More About The Future Of Internet TV?: Let’s Look To Korea (Link)

Summary: Studying countries with faster technology adoption is a great way to spot potential trends. Korea was that country with over-the-top (OTT) Internet-based video streaming. The top three South Korean OTT providers passed 800K subs during the year with 90% broadband penetration rates. While that seems high, Gurley notes that estimates a few years back called for millions of subscribers. 

Favorite Quote: “One way to have an advantage in “predicting” what will happen is to look at other countries that are further evolved in terms of broadband. The most obvious of these, with over 90% broadband penetration, is South Korea.”

October 29, 2009: Google Redefines Disruption: The “Less Than Free” Business Model (Link)

Summary: Google licensed its map data from two main companies: NavTeq and Tele Atlas. As such, the data-based companies had an economic advantage over Google. That was until Google deployed its own cars and created its own turn-by-turn GPS application. Then Google did the unthinkable, they gave it away for free inside its Google Android OS. In one move, Google went from price-taker to price-maker.

Favorite Quote: “This is not just incredible defense. Google is apt to believe that the geographic taxonomy is a wonderful skeleton for a geo-based ad network.  If your maps are distributed everywhere on the Internet and in every mobile device, you control that framework.”

January 5, 2010: Android Or IPhone? Wrong Question (Link)

Summary: It was easy to think Apple and Android fought head-to-head. But that wasn’t true. The iPhone partnered with AT&T, demanded wild economics (upfront payments & revenue shares), and closed its user interface/ecosystem. Google made Android open-source and paid cellular carriers via advertising revenue shares. The result? iPhone captured the high-end of the market while Android flooded/dominated the lower-end where basic smartphones were 10x better than a consumer’s existing option. 

Favorite Quote: This is why the two products do not compete head to head. With its super aggressive model, Android will be the choice of the masses, and with its sleek design and non-compromising price point, Apple will rule the high end.”

February 8, 2010: Virtual Goods, Accounting, And The Power Of The “Rental” Model (Link)

Summary: In the virtual economy, renting is a better business model than ownership for six main reasons: 

  1. Items become obsolete as a player levels up
  2. Users experience substantial inventory glut 
  3. Allows for more marketing opportunities when item needs to be replaced
  4. Price segmentation based on length of rental (i.e., 1 day, 7 day, or 30 day rental pricing)
  5. Creates recurring revenue business vs. one-time purchase
  6. Simpler accounting as there is no “durable” virtual good

Favorite Quote: “American journalists and corporate executives have been slow to appreciate the beauty, brilliance, and consumer allure of the virtual goods business model.”

April 28, 2010: When It Comes To Television Content, Affiliate Fees Make The World Go ‘Round (Link)

Summary: If you want to understand the cable/media industry, follow the money, or in this case, the affiliate fees. Affiliate fees were a $32B business in 2010. ESPN is a good example. Content providers like ESPN “charge” $2.00/sub/month to cable companies for the right to stream ESPN content on a cable channel. Gurley notes that affiliate fees affect every aspect of the TV business, from operations to content production to financing/packaging. That there is so much money on the line ($32B) means it’ll be challenging for technology to disrupt the incumbent model. 

Favorite Quote:  “The final and most significant reason is that this is a massive, massive business, and it is critically important to understand where the money flows (most people don’t). You can spend plenty of time talking about other issues, but when it comes to understanding the key factor at play in nearly every major business decision in television, you will find affiliate fees – all $32 billion of them.”

July 8, 2010: Google Acquires ITA: Will Deeper Vertical Integration Lead To Higher Revenues? (Link)

Summary: GOOGL can’t easily penetrate new verticals for two key reasons: competition and LTV-based assumptions. Existing verticals (like travel) offer a significantly better consumer experience, often due to community-based user-generated content (UGC) and hyper-specific datasets. GOOGL cannot easily mimic these advantages. Second, GOOGL’s CPC charge would switch from an “investment’ in Lifetime Customer Value (LTV) to a repeat transaction (or fee) in the eyes of company marketing departments. 

Favorite Quote: “If you are searching for a book or an author you go to Amazon, or at the very least you do a search like “Man in Full Amazon” so that you go directly to the page you want on Amazon. The same is true for hotels with TripAdvisor and for restaurants with OpenTable. These sites offer deeper and richer experiences for a vertical searcher precisely because they incorporate deep meta-data, faceted search, transaction connectivity, and typically a form of community or UGC (user generated content).”

July 15, 2010: On Google, Growth, Pricing Power, And Valuation Multiples (Link)

Summary: GOOGL traded at ~18x 2010 earnings at the time of writing. Why were they so cheap? It wasn’t competitive positioning, as nobody could successfully dethrone GOOGL’s search engine dominance. And it wasn’t lack of growth as GOOGL was generating 20%+ top-line revenue growth. According to Gurley, GOOGL traded at a discount because its business model was “too good.” It grew reached $10B 3x as quickly as GOOGL. However, GOOGL didn’t possess MSFT’s massive embedded pricing power, so Gurley saw little operating leverage inside GOOGL’s business. 

Favorite Quote: With its ad optimization engine so amazingly efficient, Google has no obvious pricing power against its current installed base. There is simply no way to “double” the amount of spend from each customer, much less a way to take it up 20X. Additionally, they have not yet identified a product that would represent Google’s version of Microsoft Office in terms of revenue leverage.” 

November 15, 2010: Silicon Valley’s IPO Anxiety (Link)

Summary: Anxiety about going public is a self-fulfilling prophecy that leads to fewer IPOs, thus fewer new “merchandise” for investors to purchase. Gurley notes that in 2010 most IPOs came outside of Silicon Valley, reaffirming the self-fulfilling prophecy. Sure, Sarbanes-Oxly makes it more expensive to go public. And yes, there are more short-term oriented investors in public markets. However, companies assume those risks for the potential to capture sales/earnings multiples they’d never see if they stayed private. 

Favorite Quote: “To this point, and perhaps ironically to some, most of the people I know that work in high tech mutual funds and hedge funds would like to see more IPOs not less. They are tired of trading the same large technology names that are showing limited equity returns over the past 10 years, and have very low growth opportunities/ambitions.”

March 24, 2011: The Freight Train That Is Android (Link)

Summary: Android and Chrome aren’t business “products”, but a strategy of expanding GOOGL’s existing economic moat. GOOGL removes the layer between itself and its end-user by offering free (or less-than-free) software products (like OS, Search Engines, and Maps). The Search Engine funds this expensive “scorched-Earth” moat expansion policy via its Advertising business (its castle). In essence, GOOGL wants all the market share, but none of the economics. How can one compete against that defensive model? It’s simple, you can’t. 

Favorite Quote: “This is the part that amazes me the most. I don’t know if a large organized industry has ever faced this fierce a form of competition – someone who is not trying to “win” in the classic sense. They want market share, but they don’t need economics. Imagine if Ford were faced with GM paying people to take Chevrolets? How many would they be able to sell? What if you received $0.10 for every free Pepsi you consumed? Would you still pay $1.50 for a Coke?”

May 24, 2011: All Revenue Is Not Created Equal: The Keys To The 10X Revenue Club (Link)

Summary: Only a select few companies can (and should) trade at 10x Price/Sales. The reason is that revenue (and revenue growth) isn’t created equally. There are good and bad flavors of growth. Gurley reveals the ten most important criteria for Revenue Growth Quality by asking 10 questions: 

  1. Does the business have a competitive advantage (Buffett’s “moat”)?
  2. Does the business possess network effects? 
  3. How predictable/visible is the company’s revenues? 
  4. Are there high or low switching costs? 
  5. Is this a high or low gross margin business? 
  6. Does the business generate positive marginal profitability?
  7. How concentrated is the company’s revenues? 
  8. Does the company depend on 1-3 key partners? 
  9. Does the business grow via advertising or organic word-of-mouth? 
  10. How fast is the company growing revenue? 

This is not an exhaustive list, but it’s a great starting point in determining if a business has what it takes to (potentially) trade at 10x Price/Sales. 

Favorite Quote: What drives true equity value? Those of us with a fondness for finance will argue until we are blue in the face that discounted cash flows (DCF) are the true drivers of value for any financial asset, companies included. The problem is that it is nearly impossible to predict with any accuracy what the long-term cash flows are for a given company; especially a company that is young or that might be using an innovative and new business model.” 

September 14, 2011: On IPOs: If You Are Going To File, Make Sure You Price (Link)

Summary: Companies that file an S-1, only to pull the filing, sow seeds of doubt amongst investors, bankers, and internal employees. Pulling an IPO filing begs many questions, like “Was their valuation too high?” or “Maybe there isn’t enough demand for the stock?” Or even “I wonder if the company’s growth is slowing down and they don’t want to publish those figures?” Regardless of the reason, companies that file S-1s should have the courage to see it through. 

Favorite Quote: “An open IPO window attracts two types of companies – those that should go public, and those that “need” to go public for capital reasons. Portions of the “need” group will always fail to find supporters, and therefore you should not view delays and withdrawals as signs of a weak IPO market.” 

September 18, 2011: Understanding Why Netflix Changed Pricing (Link)

Summary: Hollywood forced Netflix to change its pricing. Netflix’s original business model formed around the 1908 “First Sale Doctrine” Supreme Court Ruling. The ruling allowed NFLX (or anyone) to rent a DVD the same day of purchase. In this model. NFLX has relatively fixed costs and unlimited “streaming” rights. However, digital is the opposite model. Hollywood demanded an affiliate fee-like pricing model, where NFLX paid Hollywood per subscriber per month for the right to digitally stream its content. Digital now became a fixed rights distribution with unlimited potential costs. NFLX had to increase prices to make its digital model work. 

Favorite Quote: Netflix could not afford to pay for digital content for someone who wasn’t watching it. This forced the separation, so that the digital business model would exist on it’s own free and clear. Could Netflix have simply paid the digital fee for all its customers (those that watched and not)? One has to believe they modeled this scenario, and it looked worse financially (implied severe gross margin erosion) than the model they chose.”

November 15, 2011: You Don’t Have To Tweet To Twitter (Link)

Summary: Twitter doesn’t compete with Facebook or other social media platforms. Instead, it competes with other news sources, like print/TV media, blogs, and other websites where users publish information. The great thing about Twitter, too, is that you don’t have to tweet to recognize its value. Users get tremendous value from following other people without the need for others to follow them. Plus, Twitter’s strong-form network effects grow with each new user on the platform as more users amplifies any one person’s potential to share information at scale. 

Favorite Quote: Much like Google, Twitter points out to the world. It’s a “discovery engine” and an “information utility” rolled into one. With Twitter, you get news faster, you see updates from your favorite artists, you hear directly from key politicians, and gain insights from influencers in a wide variety of specializations. Just as Facebook is symmetric in terms of its poster-reader relationship, Twitter is highly asymmetric. The majority of the tweets on Twitter are posted by a small sub-set of the users.”

Years: 2012 – 2015

January 5, 2012: Thinking About Diets And Other Complex Matters (Link)

Summary: Whether it’s diets, stock prices, or weather changes, humans love finding patterns for complex matters. If something is too complex for our feeble human brain to comprehend, fear not! We simply create a causation or a pattern so that our minds can somehow understand it. The lesson? Watch out for those that spew “certainty”, those that avoid fresh perspectives or people who won’t / can’t change their minds. 

Favorite Quote: When it comes to not fully understood complex systems, it is easy to get things wrong. In fact, its easy for everyone to get them wrong. Don’t fear the new idea or the fresh perspective, and don’t believe something just because everyone else does. But watch out for the preacher with certainty — the ones that are spewing hellfire and brimstone. They are the ones most certainly to be wrong.”

February 1, 2012: Why Facebook Clearly Belongs In The 10X Revenue Club (Link)

Summary: This was one of my favorite Gurley posts as we became a fly on the wall, listening to how Gurley analyzed Facebook (FB) at the time of IPO. Gurley runs FB through his 10x Revenue Club Criterion and determines that the company firmly belongs as a card-carrying member. Gurley ended up valuing FB around $96B market cap. As of this writing, it trades at $540B. 

Favorite Quote: “With all the hype, assume a 12x multiple on the $6, and you end up right at $72B. You can double-check this with earnings. As operating margin is stable, 60% growth would result in $1.6B in after-tax earnings. At $72B, this is a 45 PE ratio for a company growing at 60%. At a 60 PE, you would have a $96B market capitalization.”

February 23, 2012: Why Dropbox Is A Major Disruption (Link)

Summary: Gurley saw Dropbox (DBX) as a major disrupter because it took something highly complex (file synchronization) and made it “brain dead simple.” However, it’s not in making something formerly complex, simple. It’s the fact that DBX now eliminates dependence on specific computer hardware and software. Who cares if you use iMac or Windows? And who cares if you lose your laptop or phone? If everything’s stored on DBX, you haven’t lost anything. DBX, in essence, commoditized computer hardware and software. 

Favorite Quote: Once you begin using Dropbox, you become more and more indifferent to the hardware you are using, as well as the operating system on that device. Dropbox commoditizes your devices and their OS, by being your “state” system in the sky.” 

April 19, 2012: My Life With Bing (Link)

Summary: Gurley switched his default browser from Google to Bing for two months. His findings were interesting. He noticed that on “core search” functions, Bing was on-par with Google. However, the biggest difference Gurley noticed was how conditioned he was to Google’s UI/UX. Moreover, he noticed how frustrating it was trying to navigate (read: learn) a new UI/UX in Bing. In other words, customer lock-in doesn’t have to come from product superiority or barriers to entry. It can come from familiarity with navigation and the power of personal routines. 

Favorite Quote: At the end of the day, for me, my user “lock-in” is associated not with the quality of Google results, but rather with the understanding of the UI features and levers.  More like a traditional software application.”

April 27, 2012: Intuit To Acquire Demandforce For $424MM (Link)

Summary: Demandforce is a case study on two important company-building topics: focus and local networks. Gurley frequently mentioned that Demandforce flew under-the-radar from the media, and instead focused all their efforts on their customers and product. Additionally, Demandforce operated in the Local Internet world of small business. Demandforce gave local businesses access to enterprise-level SaaS “front office” tools. In effect, the company leveraged the power of the Internet with the pervasiveness of smartphones to service a $125B+ industry.

Favorite Quote: “In a day and age of social media, where many companies project a persona much larger than reality, Demandforce chose instead to focus on its customers and its products. We never even announced Benchmark’s funding of the company, which I believe is unprecedented. The Demandforce team always felt that the attention should be focused on the customer rather than the company.”

June 25, 2012: Social-Mobile-LOCAL: “Local” Will Be The Biggest Of The Three (Link)

Summary: Local is a massive and exciting market opportunity for startups to build the next billion-dollar business. There are a few reasons for this belief. First, smartphones have given startups access to billions of people’s locations, allowing them to build hyper-local products and services (think Nextdoor, etc.). Internet adoption rates also remain historically underpenetrated for local small businesses. Finally, local graphs incentivize startups to go deep into specific verticals (like travel, accounting solutions, table reservation), insulating itself from larger incumbents like Google.

Favorite Quote: But the really exciting part is that we are still really early in this process of transformation away from listing/directory advertising to a local Internet.  By way of comparison, in the fourth quarter of 2011, Southwest Airlines reported that 86% of its revenue was booked online.  By comparison, only 12% of US restaurant reservations are booked online. Only 15% of dentists are connected to customers through services like DemandForce.  Only 3% of takeout orders are processed through online offerings like GrubHub. And less than 1% of realtors are premier agents on Zillow.”

Tyler Durden
Sun, 07/17/2022 – 16:30
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