Stuck on a Plane? Reading These Books Will Help Boost Your Business.

Stuck on a Plane? Reading These Books Will Help Boost Your Business.
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CEO and co-founder, InsightSquared
5 min read
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Like most entrepreneurs, I spend a staggering percentage of my life on airplanes. While I’ll never enjoy the redeye from San Francisco to Boston, I do appreciate that being stuck on a plane allows me uninterrupted time to read. Reading lets me shift from my usual mode of running my business to thinking about my business -- and that slight change in perspective can be enormously helpful.

Related: 5 Books to Read Before Starting Your Business

If you’re building a startup, here are six books to consider the next time the boarding doors close. They’ve helped me plan, hire and lead more effectively.

1. The Innovator’s Dilemma, by Clayton M. Christensen

The Innovator's Dilemma

Christensen details how smart companies can fail -- even when they appear to be doing everything right. For example, mature companies are naturally pulled up-market in pursuit of bigger deals. Yet ignoring the innovation-thirsty lower end of the market may expose these companies to disruption, which almost always emerges from below.

When I started InsightSquared, we based our model on Christensen’s theory of disruptive innovation by architecting our sales analytics software for smaller companies that had been traditionally priced out of the business intelligence market. In fact, we start every company meeting with Drake’s “Started From The Bottom” as a reminder to maintain our focus on this overlooked audience.

2. Crossing the Chasm, by Geoffrey Moore

crossing the chasm

Buyers at each stage of the adoption curve have a unique set of expectations. For example, early adopters value being first, whereas the next segment, the early majority, shift to a more pragmatic mindset. Leaders that aren’t mindful of shifting customer needs as the market matures risk disappearing into the chasm.

I’ve read all three editions of this book, and most of my company has, too. It’s helped us spot when our early adopters (those who were thrilled to be a part of our growth) shifted to become the early majority (those who demanded proof, such as customer references). This book helps me monitor where we are on the adoption curve, and adjust product development and sales and marketing strategy accordingly.

3. Leadership and Self Deception, by the Arbinger Institute

Leadership and Self Deception


This is a fascinating book that looks at people’s tendency to view others as objects rather than fellow human beings. Interestingly, it’s not just the people being treated as objects who are negatively affected. Those who perceive others in this manner also fail to reach their full potential, because their self-serving tendencies interfere with healthy team dynamics -- thereby limiting the positive impact they can have on an organization.

I believe in the principles outlined in “Leadership and Self Deception” so deeply that I use the concepts to guide my hiring decisions.

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

4. The Hard Thing About Hard Things, by Ben Horowitz

The Hard Things about Hard Things

Horowitz shares his advice on running a startup and offers practical solutions for the kinds of real-world problems that business school doesn’t cover. He encourages entrepreneurs to embrace their struggle, own up to their failures, share bad company news quickly, and always communicate with their team.

As an entrepreneur, I was blown away by how much I could relate to this book. Reading it was a visceral experience. One of my favorite excerpts is when Horowitz discusses how nearly every company goes through life-threatening moments. There’s even an acronym for it: WFIO (“We’re Fucked, It’s Over.”) Every entrepreneur I meet has experienced this feeling at least once, and I appreciate that there’s a common, safe way for us to share that feeling with one another.

5. The Checklist Manifesto, by Atul Gawande

The Checklist Manifesto

According to Gawande, most mistakes occur as a result of ineptitude, not ignorance. By whittling down complex tasks into a checklist that outlines each key step, however, mistakes can be prevented.

Everyone can benefit from basic reminders. For example, our sales team has “put new information into my customer relationship management system after every call” on their checklist. In may seem trivial, but we’ve prevented countless mistakes by checking off this seemingly obvious step.

6. The Elegant Universe, by Brian Greene

The Elegant Universe

This book isn’t about business or leadership. It’s a fascinating read about physics and string theory in which author Brian Greene seeks to explain how the universe works.

I admire the way Greene breaks down incredibly complex concepts in a way that people who aren’t physicists or mathematicians can understand. This book reminds me of that important truth: True experts must be able to explain anything in a thoughtful and accessible manner.

Part of building a startup involves learning how to find the people and resources that can help you along the way. I found these six books to be incredibly valuable, and they continue to guide me as I work to grow my company. Next time you’re stuck on a plane, I urge you to give them a read.

Related: 5 Tips to Read 100 Books a Year

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