The Best Books On How To Start A Side Hustle

The Books I Picked & Why

Hacking Sales: The Playbook for Building a High-Velocity Sales Machine

By Max Altschuler

Hacking Sales: The Playbook for Building a High-Velocity Sales Machine

Why this book?

Max is one of the thought leaders in modern sales development and acceleration. His book is full of actionable advice for the modern sales rep – and entrepreneur – to blast through the building and closing of a sales pipeline. Since entrepreneurship requires selling, I highly recommend this book.


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Sam Walton, Made in America: My Story

By Sam Walton, John Huey

Sam Walton, Made in America: My Story

Why this book?

Sam Walton didn’t have a side hustle, but he was certainly a hustler. He fell in love with retail outsmarted his competition. It’s a fascinating read and takes the story of Walmart, one of America’s most successful companies and largest employers, all the way down to a competition between five and dime shops across the street from each other in a small town in Arkansas. If you think of each store as a stand-alone business (as Sam did), then Sam Walton was perhaps the most successful parallel entrepreneur in history.


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The Art of Profitability

By Adrian Slywotzky

The Art of Profitability

Why this book?

This book came by recommendation from Jonathan Siegel, the brains and brawn behind Xenon Partners, a private equity firm that I joined in 2018. This book summarizes several profit models presented by a fictional mentor coaching a business executive. It’s clever, poignant, and was helpful to me in thinking about other profitable business models. For example, in my side-hustle life, I use the Profit-Multiplier Model: running multiple small SaaS businesses in parallel using the same tech stack (make money off the same good or skill in different markets).


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Russell Rules: 11 Lessons on Leadership From the Twentieth Century's Greatest Winner

By Bill Russell, David Falkner

Russell Rules: 11 Lessons on Leadership From the Twentieth Century's Greatest Winner

Why this book?

A great book about leadership and business. I pick it because it’s on the reading list suggested in The Art of Profitability. I learned that focus is important. Bill Russell was one of the greatest basketball players of all time because he worked harder and played smarter than everyone else. However, he also recognized that he doesn’t play every position. He needs to have a great team, one that adapts to the competition. He needs them all to play at his level and he was able to do that, winning the NBA Finals a record-breaking 11 seasons. One way to build a successful side hustle (or portfolio of side hustles) is to recruit a great team to help you.


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Skip the Line: The 10,000 Experiments Rule and Other Surprising Advice for Reaching Your Goals

By James Altucher

Skip the Line: The 10,000 Experiments Rule and Other Surprising Advice for Reaching Your Goals

Why this book?

James Altucher has produced a gem. It is full of discrete shortcuts that anyone interested in finding success in business can apply to get where they’re going faster. I learned to brainstorm every day, to read often, and to work on ideas in parallel. I also appreciate that he recommends publishing early and often rather than overthinking and agonizing over every blog post and tweet. Just let it go, but have a plan, and be strategic. If that sounds contradictory, then you too should read the book. The beauty is in the nuance.


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