Entrepreneurs

7 Books (and Blogs) for the Entrepreneur in All of Us

7 Books (and Blogs) for the Entrepreneur in All of Us
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Whether you are the CEO of a Fortune 500 company, employee number two at a startup or someone who enjoys the challenge of solving problems, there is likely an entrepreneurial spirit in you.

Over the years I have filled the bookshelf in my home office with books that have helped me think through things in different ways. Sometimes what I read validates what I’m thinking, but most of the time the books led me down different paths by giving me a platform to rethink and question how to handle certain problems or situations.

To help anyone who is looking for a bit of light or in-depth reading, here are some books from my personal “bestseller list” (in no particular order).

1. Hard Thing About Hard Things by Ben Horowitz

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Hard Thing About Hard Things is one of my favorites, because it hits on so many important topics (with unfiltered transparency). It was a crucial read for me during my transition from Microsoft to Porch. I was leaving behind a predictable environment for a much riskier endeavor. Part of why I desired to make the change was because I wanted to experience and learn first-hand how to handle some of the more challenging aspects of building a business (and culture) from the ground up. This book discusses many topics relevant to both entrepreneurs and leaders at companies including advice on running a business, managing employees, hiring tactics and developing a CEO mentality. 

What this book taught me:

In a word: perseverance. You are going to make mistakes. Things are going to go wrong. The journey will become unpredictable. You need to prioritize products and people over profits and buckle up when things don’t go according to plan. This book does a great job preparing you for situations that can be very hard to prepare for. Through it all, perseverance to handle the good with the bad is a character trait I constantly keep top of mind.

Related: The Entrepreneur's Ultimate List of 8 Must-Read Books

2. The Score Takes Care of Itself by Bill Walsh

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The Score Takes Care of Itself is a great book by legendary NFL head coach Bill Walsh. When he took over the San Francisco 49ers, they were the worst team in the league with a 2-14 record. Within two years, they were the best team in football, winning the Super Bowl and on their way to becoming a dynasty, winning four titles over the next 10 years. The reason, as the book discusses, has to do with Walsh's leadership and management style. His focus was on people and his philosophy was centered on certain core values, ideals and principles.

What this book taught me:

Walsh was obsessed with execution. He believed that the way you performed in practice to be a precursor for how you performed during the game. He was unrelenting in his pursuit of perfection through repetition. Though his standards were incredibly high, Walsh understood there was a balance between a demanding character and a motivating character. He pressed on people his expectations, but also found ways to praise people in the moment so they could see and appreciate the progress they were making along the way. This technique I have used often throughout my career.

3. Leading at The Edge by Dennis N.T. Perkins

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I was introduced to Leading at The Edge while in graduate school. For those who are not familiar with the story, author Dennis Perkins lays out 10 leadership lessons people can learn from the difficult Antarctica expedition trip led by Sir Ernest Shackleton in 1914. Shackletorn led 27 explorers but after things went awry, the crew was stuck in the sea for two years in life-threatening conditions, limited supplies and little hope that they would ever be rescued. Eventually, they were discovered and all survived.

What this book taught me:

The story of Shackleton is gripping. To hold his team together for so long under such extreme conditions shows you what is really possible when people are tested and pushed to the limits. If you never lose sight of the ultimate goal and focus your energy on short-term objectives, you can get to where you need to go. For leaders, it really comes down to setting a personal example with visible and memorable behaviors that others can learn from and follow. I also learned the power of optimism and how important self-confidence is while staying grounded in reality and respecting the impacts of peril.

4. Here’s Why You Should Care About Holacracy by Adam Pisoni

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Adam Pisoni is the co-founder and former CTO of Yammer and currently the CEO of Always Be Learning. He is also a founder of Responsive.org, a movement dedicated to helping companies become more agile, adaptive and empowering. In his article "Here’s Why You Should Care About Holacracy" Pisoni focuses on the role of empowerment as companies search for ways to fundamentally change the way they work and organize in the 21st century, in particular how methods like holacracy -- a management style where leadership decisions are assigned to self-organizing teams, rather than in a top-down hierarchy -- can streamline the way decisions get made.

What this article taught me:

At Porch we strive towards developing a culture that is transparent, free of silos and allows people to own their decisions. Empowerment is crucial as we want to enable a culture where command and control is replaced by more agile ways of thinking and doing work. This article provides a good framework for how companies can approach such a goal, outlining the questions that should be posed to determine if they are truly building an agile workforce.

Related: The 6 Books Shark Tank's Daymond John Wants You to Read

5. What’s Your Hour in ‘Silicon Valley Time’? (part one and two) by Aaron Zamost

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Aaron Zamost is head of communications at Square. As a fellow communications practitioner, I appreciated the story arc from his great blog post "What’s Your Hour in ‘Silicon Valley Time’?" Zamost discussed how company narratives are like clocks:

"The tone and sentiment about how a business is doing move from positive (sunrise, midday) to negative (dusk, darkness)." It’s a very cool framework that takes into account how a business should think about their story relative to others as they experience different periods of growth.

What this article taught me:

It’s easy for businesses to keep too much of their focus on what others are doing. In many ways companies look at their stories like they are playing a game, and the press are there to keep an eye on the box score. As a company develops its narrative it’s important they keep their attention on what they can control -- the product and delighting customers. Let that be the story and worry less about how you fit into the story arc that others want to place upon you.

6. Onward: How Starbucks Fought for Its Life without Losing Its Soul by Howard Schultz

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Shortly after I completed my MBA I found myself looking for things to read to feed the routine I had developed of reading books about business. Onward was a book that transcended the learnings of a typical “business book”. Schultz outlines how the recession, new consumer behavior and overexpansion led to the company's downturn between 2007 and 2008. I found the book to be a pivotal read as it struck a balance between what it takes to run a business and cultivate a world class culture.

What this book taught me:

This book ties together the role management, leadership and the quest of a brand to connect with their customers plays in the development of a corporation’s culture. The Starbucks brand is more than just coffee. It reflects a desire to play a critical role in the development of the community, and the culture of the company reflects that. Schultz has been able to create a business and a culture where the people who work there fundamentally believe they are part of something bigger than themselves.

7. Made to Stick: Why Some Ideas Survive and Others Die by Chip Heath and Dan Heath

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Made to Stick: Why Some Ideas Survive and Others Die is a must-read book for anyone who is looking to develop the story of their brand. I teach a class at the University of Washington and this book is a core part of the curriculum. It sets out to answer a simple question: Why do some ideas stick while others don’t?

What this book taught me:

This book is as much of a reference tool as it is a fun and interesting read about how to tell a “sticky” story through examples of success and failure. My copy is literally covered with sticky notes (pun not intended!) and highlighted text.

Related: The Recipe for the Perfect Business Book