Essential Startup Reading

Reading books as a startup founder is a great way to develop fresh perspectives, ideas, and insights. I’ve gathered a few of my top suggestions for company founders.

I know… there’s a lot!

Focus on the ones that speak to you and your needs. I’ve explained why I personally liked each book and the value it may add to your startup journey.

Happy reading!

Also — I first tried to be a super-fast reader, go on Blinkist, and get summaries.

Don’t do this.

Slow down and take time.

Entrench yourself in the book.

It’s the only way that I’ve found to really understand what the author is saying.

Let's get to it!

Storytelling

Storytelling is the most important part of running a startup. Your entire job (as a founder) is stitching a cohesive narrative. To your investors, your customers, your colleagues, and your new hires.

Why should you work here, what are you building, why should someone buy your product?

If you can master storytelling, you’ll be able to effectively communicate your startup’s value proposition, mission, and vision, creating an emotional connection with your audience & eventually driving growth.

On Writing, Stephen King.

“Description begins in the writer’s imagination, but should finish in the reader’s.” — Stephen King

In his book “On Writing,” Stephen King emphasizes the value of strong storytelling. The same is true for entrepreneurship. A well-written story can generate inspiration, motivation, and business success. A story starts in your head but ends in your customer’s. You can develop trust and loyalty with your audience by expressing your stories in an emotive way.

The Science of Storytelling, Will Storr.

“Story is what brain does. It is a ‘story processor’, writes the psychologist Professor Jonathan Haidt, ‘not a logic processor’.” - Will Storr

The neuroscience of storytelling and its enormous effects on the human brain and emotion are the crux of this book. Storytelling is essential for our mental health because it helps us understand the world and establish deeper connections with people. By taking advantage of the brain’s inherent propensity for narrative entrepreneurs can drive compelling narratives in your customers, investors, and employees mind(s).

Alchemy, Rory Sutherland.

“For a business to be truly customer-focused, it needs to ignore what people say. Instead it needs to concentrate on what people feel.” — Rory Sutherland

Sutherland highlights how entrepreneurs can leverage psychological drivers behind consumer behavior in branding and messaging to create powerful connections with customers. Sutherland is the vice chairman of Ogilvy, which was actually the inspiration for the Netflix show “Mad Men”, too.

Two interesting points Sutherland makes:

Use psychology to develop persuasive marketing: Develop more persuasive marketing and advertising strategies that connect with your target audience by understanding the psychological factors that influence consumer behavior.

Reconsider traditional economic theories: Human behavior is significantly more complex than these theories imply, challenging traditional economic theories that presume people to be rational actors.

Keep on Keepin on.

Perseverance is key to achieving success. You gotta keep on keepin' on. By cultivating resilience and smashing through setbacks, you can develop the strength to achieve your goals. These next few books are great resources in learning from some of the most successful entrepreneurs.

The Hard Thing About Hard Things, Ben Horowitz.

“The hard thing isn’t setting a big, hairy, audacious goal. The hard thing is laying people off when you miss the big goal.” — Ben Horowitz

The Hard Thing About Hard Things is a crucial read for startup founders. Horowitz provides a candid and honest viewpoint on the difficulties faced by entrepreneurs. How you need to stay flexible, build a solid culture, and stay resilient in the face of failure. Ben talks about his time at LoudCloud where they committed to a $30M lease and he had to make the toughest decision to lay off a ton of people.

The Almanack of Naval Ravikant, Eric Jorgenson.

“Memory and identity are burdens from the past preventing us from living freely in the present.” — Naval Ravikant

Eric has done such an amazing job of putting the mind of Naval in a book. The “Navalmanack” focuses on the importance of cultivating a growth mindset, focusing on long-term goals, building a strong personal brand, and finding purpose in your work. Ravikant really turned me onto meditation and stoicism. I reference a book, Black Swan, which really embraces this concept of “Amor Fati” or loving one's fate. Focusing on this gives founders a sense of peace and overall clarity (it has for me).

I wrote about the Navalmanack back in March 2021, here.

Steal like an Artist, Austin Kleon.

“Every new idea is just a mashup or a remix of one or more previous ideas.” — Austin Kleon

Borrow and remix existing ideas! Kleon talks about utilizing books, other industries, and finding inspiration everywhere. Embrace the concept of “stealing” ideas and remixing them in new and exciting ways, and you can unleash your creative potential to interesting solutions.

I also wrote about Kleon here.

Management.

These books offer both general and practical advice on leadership, team building, and organizational management. Naval recommended the Black Swan, and Jarie Bolander recommended Loonshots. Lastly, John Doerr masterfully explains how to build a cohesive objective structure in Measure what Matters.

The Black Swan, Nassim Nicholas Taleb.

“I know that history is going to be dominated by an improbable event, I just don’t know what that event will be.” — Nassim Taleb

In “The Black Swan”, Taleb explores the concept of rare and unpredictable events and their impact on the world around us. Being prepared for unexpected challenges and opportunities, and developing the ability to adapt and pivot in response to changing circumstances is the centerpiece of being an entrepreneur. Taleb talks about how managers can develop more resilient and agile strategies that are better equipped to weather uncertainty. A black swan event is an unpredictable and rare event that has a major impact on the world around us. Some examples are World War II, the 9/11 attacks, the 2008 financial crisis, the COVID-19 pandemic, and the Silicon Valley Bank crisis.

Loonshots, Safi Bahcall.

“As teams and companies grow larger, the stakes in outcome decrease while the perks of rank increase. When the two cross, the system snaps. Incentives begin encouraging behavior no one wants. Those same groups — with the same people — begin rejecting loonshots.” — Safi Bahcall

As you begin to grow your company, building a diverse and multidisciplinary team that brings different perspectives to problem-solving becomes more important than ever. Bachall argues that diverse teams are more likely to generate loonshots, as they are able to draw on a wider range of experiences and knowledge (it’s Taleb’s Black Swan redundancy idea). Bachall has a handful of real examples such as the development of radar technology during World War II, the creation of blockbuster drugs, the success of Pixar Animation Studios, and the failure of PanAm (the airline).

Measure what Matters, John Doerr.

“We must realize — and act on the realization — that if we try to focus on everything, we focus on nothing.” — John Doerr

This is another essential read for any startup founder. John provides a detailed framework for setting and achieving ambitious goals, using the Objectives and Key Results (OKRs) methodology. By designing and implementing OKRs, entrepreneurs can align their teams and drive progress toward their goals. OKRs stand for Objectives (the O) and Key Results (the KRs). This framework utilizes SMART (specific, measurable, actionable, relevant, and time-bound) metrics to make sure you’re working on the projects that you should be, when you should be, and getting the outcomes you hope to.

I wrote about how we use OKRs at Sutro, here.

Life and Understanding the World.

Understanding yourself and the world around you is paramount to getting new ideas and perspectives. These next books focus on just that: how we sleep, what the world looks like to other creatures, and how our interaction with fungi (potentially) played into evolution.

Why We Sleep, Matthew Walker.

“Sleep is the single most effective thing we can do to reset our brain and body health each day.” — Matthew Walker

I couldn’t recommend this book to founders more. If you’re looking to optimize your day as a leader, sleep is probably one of the most important things you’re missing out on. Living in our startup “hustle culture” means that you can stay resilient and be ready to go each day, not show up hungover and tired. Matt explores the science of sleep and the critical role it plays in our physical and mental health, as well as our cognitive abilities, creativity, and decision-making skills. Getting enough high-quality sleep is essential for peak performance and success.

I also wrote a deep dive here.

Entangled Life, Merlin Sheldrake.

“A mycelial network is a map of a fungus’s recent history and is a helpful reminder that all life-forms are in fact processes not things. The “you” of five years ago was made from different stuff than the “you” of today. Nature is an event that never stops.” — Merlin Sheldrake

Fungi play such a critical role. You’re probably wondering why should you care as a founder? It’s interesting to see fungi’s collaboration, interconnectedness, and symbiosis. By understanding the intricate and interconnected nature of the fungal world, I personally gained new perspectives on business and innovation.

An Immense World, Ed Yong.

“It tells us that all is not as it seems and that everything we experience is but a filtered version of everything that we could experience.” — Ed Yong

An Immense World is a book on how animals and their senses perceive the world. Ed takes us on a journey through the hidden realms of animal senses, from the echolocation of bats to the magnetic fields of turtles. He reveals how animals perceive the world around them and how their senses have shaped their evolution. For founders, it not only shows you how we’re only one window in a house perceiving the outside world , but that every animal has it’s own interesting way they ‘see’ the world.

If you have any more books, just comment below! Hope this helps.

Music I was listening to while I wrote this

Was on a lofi kick this evening, and listened to Astro Chill by The Experience.

This is day 36 of my #90DayOfProse challenge.

The meta image was generated via Midjourney via the prompt “a person reading a book with many books around them”.