2020 Winter Startup Reading List

I love reading books about startups and business. I thought I’d share some good ones I’ve read in the past year or two with a quick blurb about why you might like them if you are looking for something new and interesting or are in a rut. This list got kind of long as I was writing it. I really enjoyed all of them so I would have felt guilty leaving any out.

The Outsiders by William Thorndike

This tells the story of eight different CEOs at large companies and provides insight into their decision making process. I personally like this one because coming from the startup world I reflexively viewed the world from a different lense (more product and sales oriented, less financial). This one opened up a new perspective for me in terms of thinking about businesses from the vantage point of capital allocation decisions. That was really helpful. Most startup founders probably aren’t thinking about making acquisitions, but this book got me thinking about situations where that might make sense as well.

The Hard Things About Hard Things by Ben Horowitz

This one is something of a Silicon Valley classic. It is a fun read about Ben Horowitz challenges during the dotcom period. He is now a prominent VC but this shares the ups and downs he faced running a company during that volatile time. There are some great tidbits of wisdom in there (like the famous essay about what makes a good PM) but mostly it’s a fun story. I’m not sure this one will necessarily make you feel better about your own struggles but it can help you realize even companies that have raised a lot of money aren’t out of the woods yet and those founders still face immense (but different pressure).

How I Built This (Podcast)

This is a great podcast where founders tell their story about how they built their company. There is a lot of great information and practical wisdom since every story is different. Great for when you are walking, driving, exercising, etc. Highly recommend.

Bad Blood by John Carryou

This one is awesome. John Carryou is a WSJ reporter who did an amazing investigative job telling the story of Theranos. Its CRAZY! And no matter the state of your business, you will probably think “damn at least I didn’t do that”. Scumbag city. But also goes to show how even smart people can get tricked by a charismatic leader. This is probably why some people joke that psychopaths are the best at raising money.

The Everything Store by Brad Stone

This book tells the story behind Amazon, its origins and its quest for global domination. It provides a lens into what makes Amazon such a unique and incredible company. Tidbits like how when trying to get approval for launching a new product, a manager writes a mock press release rather than a PRD are great pieces of wisdom that you can take with you and apply in your own career.

The Third Door by Alex Banyan

Alex Banyan was a student at USC and wanted to interview the wealthiest people in the world (specifically Bill Gates) to find out their secrets to success. This book tells his story and the awesome, crazy journey he went on to actually make it happen. It’s called “The Third Door” because of a theory he shares in the book that most people follow one of two conventional paths in life where they wait in line for access or a slow rise to “success”, but that people at the top avoid this slog completely and find a side door to get what they want much more quickly. Great story and if you are a founder I imagine this will be helpful in giving you mental permission to try some unconventional tactics.

The Lean Startup by Eric Reis

Over 10 years old by now but a modern classic. Eric Reis talks about his experience building IMVU (a company that let people make their own avatars in a virtual world) and lays out the “lean startup” framework that has become very popular. The core idea is to fail fast and iterate quickly; that you learn the most by doing and not to fixate on making products or services perfect before you launch them. I am a big fan of this approach (as long as we aren’t talking about airplanes, medical equipment or Robinhood offering uninsured high yield savings accounts).

The Upstarts by Brad Stone

This tells the story of AirBnb and Uber. They are obviously examples of huge successes in the second wave of internet companies and the “sharing economy”. Aside from being really interesting, it’s good food for thought in terms of thinking about what the next evolution of tech will be and how to get in front of it. A lot of people believe it will involve IoT and the connectivity of everything. But maybe you’ll have a different opinion. This one also provides a close look at specific founders and their personalities which is always fun to read for me.

Shoe Dog by Phil Knight

Fun book. I live near Portland now so this one was cool for some local history. I also had no idea about the history of Nike and how scrappy its origins were. I loved the fact that they literally just started selling shoes out of the back of a car. This story is an ode to not over analyzing and just getting the hell out there and doing something.

Disrupted by Dan Lyons

Dan Lyons was a newsweek reporter who was laid off and decided to work at a tech company. He ended up getting a job at Hubspot doing content marketing. This is a cynical and satirical look at the startup world. It was funny for me to read about the tech world from the perspective of someone who has not been immersed in it for so long. You are reminded how ridiculous and “douchie” it can be. If you want something light and a good “guilty pleasure” read this is a nice one.

Leading by Alex Ferguson and Wooden: A Lifetime of Observations by John Wooden

These aren’t really startup books but they offer a lot of great insights. I am a big fan of both of these guys and reading about their leadership style and how they approach management decisions was very useful for me. For example, Alex Ferguson talks about dealing with superstar players and making sure that no one is ever above the team. I’m sure we have all dealt with a very talented employee we are afraid to lose but who is also a really negative influence on the team. “Fergie” has the answer for you.

Radical Focus by Christina Wodtke

I wouldn’t really call this one fun. But it’s short and has useful information. There has been a big movement over the past decade to develop a better system for setting goals and creating accountability. This book talks about OKRs as a goal setting framework and shares some examples. You can probably read the whole thing on a flight and you’ll have a new tool in your arsenal. I read this when I had a meltdown about being a terrible manager.

Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days

I love this one because it lays out a step by step guide to running a 5 day design sprint. This is the framework allegedly used by Google Ventures as well. Even if you don’t have 5 days, you can adopt these steps into shorter sprints or borrow elements of this for productive brainstorm. Definitely valuable for me.

Positioning: The Battle for your Mind by Al Reis and Jack Trout

This is about branding. It’s a bit older but shares a number of good examples of successful marketing campaigns (ie Avis “We are Number Two so We Try Harder”). You’ll learn a lot of practical tactics and frameworks for thinking about how to position your company. I found this book to be intriguing. “Branding” and “positioning” can be so abstract and vague to a lot of people. If you are one of them, this should help!

I hope you like the books on this list as much as I did!

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