The Boldness of Bezos

This weekend, I spent some time reviewing my notes on The Everything Store, written about the rise of Amazon – a story that’s inseparable from the rise of Jeff Bezos. Similar to Apple and Steve Jobs (through 2011, at least), the company and the founder are both one and the same. After having read Warfighting recently, one defining characteristic of Bezos that clearly resonates is his boldness. Bezos is nearly always willing to take risk to strike a decisive blow or innovate. This willingness is apparent in the very beginnings of Amazon; he left a high paying job at a quantitative hedge fund because he saw a massive paradigm shift – the rise of the internet – and decided he couldn’t be left behind. Not only does he decide he wants to participate in the rise of the internet, but he creates a vision of “The Everything Store”, with limitless selection and personalized service – a very small vision, indeed.

Examples of his boldness abound in the history of the company, on both the success and failure sides of the ledger. The Kindle (e-reader + tablet), AWS, Amazon Marketplaces, user generated reviews, personalized purchase recommendations, along with the core retailing business were all major successes. The Fire Phone, Amazon zShops, Amazon Auctions, the multiple massive distribution centers that were closed during the bubble, raising $2B+ of debt for poor acquisitions, and venture investing in a number of category specific e-commerce flameouts register as failures. All told, Bezos probably failed more than he succeeded. But his successes were orders of magnitudes larger and more impactful. AWS, which now pulls in $6B and growing in revenue, is proof enough.

Bezos is constitutionally unafraid to take big swings – the kind of swings that change the outcome of a battle, or drastically lower the costs of starting a technology business, and thereby enable a wave of innovative companies. The kind of swings that are exciting, both as an investor and a human being.


Startup strategy – as taught by the Marines

While in transit to Gambia last month (24+ hours each way), I got the chance to catch up on some reading – including Warfighting, the US Marines’ manual / manifesto for conducting and preparing for conflict (recommended by Keith Rabois, a veteran operator from Paypal & Square). Though not written with startups or personal development in mind, the book ends up being very relevant to both. Startup and war analogies are extremely common (e.g., competitive battles, fighting to survive), but the application of military strategy to startups is, if anything, undervalued.

One of the concepts I found highly applicable was how the Marines deal with uncertainty.  Like operating in an emerging market or disrupting an old one, nearly all decisions in battle must be made with incomplete information.  Teams (and especially their leaders) must be comfortable operating and executing effectively, knowing that their initial understanding of the situation is missing important detail.  The marines try to mitigate this lack of information through four strategies, all of which sound similar to what has become standard startup advice:
– Developing simple, flexible plans that allow for disorder and uncertainty
– Planning for likely contingencies
– Developing standard operating procedures that allow for trust to emerge between commanders and junior officers, without explicit, top-down orders
– Encouraging initiative amongst their subordinates. More specifically – they expect their junior officers to use the informational advantage on the ground to make quick decisions and exploit enemy weaknesses.  This doesn’t mean junior officers aren’t held accountable for their decisions; but the graver sin is unwillingness to take action.

This is only the tip of the iceberg; the book is littered with insightful takes with clear applicability to an early stage business. If you’re looking for a short, good read I’d definitely recommend Warfighting.

Looking for reading buddies

Reading is my favorite hobby – but this year, I’ve cut back the volume of books to allow myself more time to explore new hobbies, build my network here in Chicago, take on interesting projects (like this blog!) and create room for serendipity.

One activity I’d like to begin is having more discussions around the books I do read. I didn’t realize what a privilege it was to have group discussions with smart people who have read the same material in college, but I wish I had more of them nowadays. Having those conversations always forced me to examine the core arguments more closely, develop an opinion and weigh it against others’, and ultimately retain more knowledge. In short, I left the discussions smarter.

So I’d like to use this post to share some of the books I’m planning on reading this year, in the hope of finding someone (or multiple people) willing to read them along with me and discuss them. Most are related to startups or business, and the conversation can be in person (if you’re in Chicago), via email, or whatever other medium works best. Here’s the current list for 2015 (open to suggestions):

If you’re interested in reading / discussing any of these with me, send me a tweet and we’ll figure out the logistics. Hope to hear from you soon!