My views on the market, tech, and everything else


A Dozen Lessons on Building a Business from Sarah Tavel

  “Ultimately when evaluating an early stage company, I say it’s a combination of art and science. The art is understanding how products work, the science is knowing how to measure it. The earlier the company, the more it is about art, which in this case is assessing what I think of the product and the use case.”  Tavel is a great fit for Benchmark since the firm has always […]

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The Dot-Com Boom and Bust

  “Most of the entrepreneurs today weren’t around in ’99. They have no muscle memory of it whatsoever.” Bill Gurley (September 2016) Unlike the entrepreneurs Bill Gurley is talking about, I have a lot of muscle memory that resulted from the Internet bubble. There is no way you can fully convey in words the experience being in the lead car as an investor in that roller coaster. Looking at the […]

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A Dozen Lessons on Finance and Business from Ambrose Bierce

Ambrose Bierce started his career as a printer’s devil (apprentice) at an Indiana, paper after he completed about a year in high school. In 1861 he enlisted in the 9th Indiana Volunteers and fought in a number of American Civil War battles, including Shiloh and Chickamauga. He was seriously wounded in the Battle of Kennessaw Mountain in 1864 and served until January 1865.  After the war he worked as an […]

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How to Make Decisions like Ray Dalio

What is most interesting to me about Ray Dalio is his decision-making process. This blog post is limited to a discussion of that process and not Bridgewater’s philosophy generally. If you are interested in understanding Bridgewater and Dalio more broadly, Dalio has a book coming out this fall which expands on his widely circulated “Principles” document.  I have written a more general blog post about Dalio on this blog, which […]

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The Rise of the Freemium Business Model

  Freemium describes a business model in which a business gives one product away for free or at a subsidized price and then either: (1) sells another profitable product to this user base; or (2) sells access to that user base to third parties (e.g., advertisers). Three versions of the Freemium approach are: Available Forever- No premium versions are made available. Google and Facebook are examples that monetize with advertising. […]

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A Dozen Lessons about Business Valuation from the Iridium Debacle

  One of the best illustrations of the many ways a business valuation can go wrong is the pre-bankruptcy story of mobile satellite service Iridium. I knew Iridium  well since I did potential acquisition due diligence on Iridium several times and because people who worked for Craig McCaw had a long history with Motorola. We (Eagle River) always passed on buying Iridium no matter how low the price dropped. The […]

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A Dozen Lessons about Business, Investing and Money from Lil Wayne (Weezy)

  1. “They can’t put no more Weezy baby out. That’s that cash money vasectomy.” From the song: Grateful. That there was a feud between Lil Wayne and Birdman and another feud with the record label which has distributed Weezy’s music is well known. The core of the issue is “wholesale transfer pricing” (WTP).  Simply put:  WTP is the bargaining power of A that exclusively supplies a unique product X to B […]

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A Dozen Beliefs About Business, Money and Life that Kanye West Shares With Other Great Entrepreneurs and Investors

1.“For me, first of all, dopeness is what I like the most. Dopeness. People who want to make things as dope as possible, and, by default, make money from it.” As everyone who is dope knows, “dopeness” is an adjective used to describe the awesomeness of a person, place or a thing. In these sentences Kanye is in effect repeating the Y Combinator motto as stated by Jessica Livingston: “Make […]

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Core Product Value and Entrepreneurial Success

  I have previously written about Minimum Viable Product (MVP) and Product/Market Fit (PMF). These are important processes based on the scientific method that can be used to test a value hypothesis. That hypothesis does not just appear via spontaneous generation. Andy Rachleff describes what should be included in a value hypothesis as: “the features you need to build, the audience that’s likely to care, and the business model required […]

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