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Guest Blog: 8 Entrepreneurial Must-Reads NOT About Business


Guest Author: Scott Fenstermaker

Good founders constantly seek to improve their technical and business skills. But they also work 15-hour days, after which it is tedious to try and force oneself to consume even more tactical business content. I know that I find it nearly impossible to keep reading about business techniques during my precious few hours of downtime. I crave respite. 

As a start-up mentor, most of the key ideas I pass on to founders don’t necessarily come from business books. In fact, I have found that my most profound shifts in business thinking have come from reading specifically non-business books, or at least books that don’t promise “5-minute” business success.

The best books for founders are the ones that, regardless of their domain, teach you to value counterintuitive and contrarian wisdom, to test rather than to assume, to clarify your position in the world through effective writing, to tinker, to cultivate the feedback you are most afraid of hearing, and to understand how our world is influenced by randomness.

Here are the best non-business books for shaping the minds of start-up founders:

Fooled By Randomness - Nassim Taleb

I recommend Taleb’s Fooled by Randomness to anyone who will ever look at analytics (this includes all founders by definition). The first rule of looking at any data is to be able to distinguish between a real effect and an artifact of randomness.

This book opens one’s eyes to the surprisingly disproportionate effect of randomness on our lives, and how we tend to invent unsupported narratives to fit essentially random outcomes.

Alchemy: The Surprising Power of Ideas That Don't Make Sense - Rory Sutherland

This book is not so much an instructional manual as it is a manifesto on moving beyond our infantile attachment to logic.

Rather than come up with a marketing successful campaign on the logic that “mothers will respond to X”, or “middle-aged businessmen will respond to Y”, Sutherland tested options that made sense and other options that did not make sense. Instead of trying to tell the market what he thought it should want, he experimented.

Sutherland quotes his company’s famous founder David Ogilvy, “...people don’t think what they feel, they don’t say what they think, and they don’t do what they say.” Asking people what they want won’t get you there. You have to test a million things and follow the response. Ground up, not top-down.

Think Twice: Harnessing the Power of Counterintuition - Michael J. Mauboussin

To process as fast and effectively as they do, our brains work as simplifying machines. Because of this, our sense of how the world works is predictably divergent from reality: we think our situations are more unique than they are, we rely on experts uncritically, we superimpose cause/effect relationships, etc.

Founders are that rare breed who specialize in a world of counter-intuitive wisdom; start-ups are nothing more than proofs-of-concept that the market is somehow different from how people assumed. Founders understand that their gold lies in digging into a surprising result to find the distinction that others are not yet making.

Letters to a Young Contrarian - Christopher Hitchens

Hitchens is my model not only for writing, but also for critical thought. Opinions do not count for anything, he maintained. The truth lies in “not what you think, but how you think.”

Founders are contrarians. They’ve chosen a more solitary, more long-odds profession over muddling along with the Middle Management Masses. Hitchens understands what that position feels like. He understands that contrarians can be among the most valuable of society’s gems; if you have worked out a truth that is not easy for others to accept, your road can be simultaneously urgent and lonely.

Antifragile: Things That Gain from Disorder - Nassim Taleb

What if you could build a business that was not only impervious to volatility but actually gained strength from disorder?

Antifragile is, in my option, Taleb’s most interesting and consequential book. Taleb is a probabilist who specializes in asymmetric risk: events with consequences that scale disproportionately to the system itself. A Richter-6 earthquake, for example, does exponentially more damage than a Richter-3 earthquake. Adding 10,000 cars to a city’s streets slows traffic exponentially more at rush hour than it does early in the morning. The greater the exponential curve, the more “fragile” we are to things like earthquakes and traffic.

But some things, particularly organic things, are not just robust but antifragile. The cells within an organism are trial-and-error machines; the successful ones replicate, and the unsuccessful ones are cleared away. On a macro-scale, Darwinian evolution works on the same principle relative to a species.

What if a founder could build their company like an organism? Something that could respond to disruption and strengthen itself as a result?

On Writing Well - William Zinsser

On Writing Well is a short, entertaining overview of good (cross-domain) writing.

I’m not recommending this book because I think you’ll write a blog. That’s the least of it. Clear writing is clear thinking. Clear thinking leads to a clear company mission, a clear value proposition, a clear vision for your customer as to how their life will be better with you being part of it.

Influence: The Psychology of Persuasion - Robert Cialdini

Cialdini’s seminal work covers six factors that affect whether or not we will do something that someone else wants us to do.

Every founder is trying to find a customer base. Every articulation of value to those potential customers will include some or all of Cialdini’s famous six “weapons of influence”.

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph - Ryan Holiday

I originally read The Obstacle Is the Way during a bleak time in my own life, and I found it to be a very welcome introduction to Stoic thought.

Stoicism is very useful for founders, but Seneca or Marcus Arrelious might be slightly unapproachable. Holiday’s work is a well-written primer, accessible to anyone and filled with insights on the resilience and emotional context that can bolster a founder’s state of mind.

About Scott Fenstermaker

Scott Fenstermaker is the Digital Director of Riskonnect, and a marketing and analytics mentor at 1871. As a marketing strategist, he has over 20 years of experience growing digital agencies and early-stage tech/SaaS companies. Find him on LinkedIn, or schedule a mentoring session through 1871.

Read the 1871 Blog for news about the Chicago technology and entrepreneurship community, as well as helpful tips, guides, and insights into the startup and investment world.

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