Best Books, Podcasts and Streaming Shows for Entrepreneurs This Summer

Our contributors recommend the best content to help unwind - and maybe even pick up some helpful business pointers from - over the rest of this, or any, summer.
Best Books, Podcasts and Streaming Shows for Entrepreneurs This Summer
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14 min read

In case the oppressive heat and hurricane warnings haven't made it plain, we are officially in the throes of summer. But it isn't just any summer. Most of America is emerging from a year and a half of inactivity amid the pandemic, and people have been hitting the highways and airport terminals in record numbers to reunite with loved ones or simply get off the grid. 

That also means there's millions of Americans looking for relatively light content to help pass the time while in transit or simply serve as pleasant company while they relax and restore. 

Fortunately, our Entrepreneur.com contributors have plenty to recommend. Below, we gathered some of our regular voices' most enthusiastic suggestions for what books to read, podcasts to download and TV shows to stream between now and Labor Day — whether the goal is to escape the everyday, sneak in a bit of insightful business expertise or both. 

Happy unwinding! — Kenny Herzog

Related: 10 TV Shows Every Entrepreneur Should Watch on Netflix

Books

Image credit: Portfolio

Happy Work: A Business Parable About the Journey to Teamwork, Profit, and Purpose by Chris Reimer 

I had never read a business book that was told in a narrative storytelling approach before reading Happy Work. It immediately captivated me, and I couldn't put it down. I finished it in about three hours on a bus ride to a tourist stop while on vacation. It's got an inspirational message for business owners wrapped into an entertaining read. Loved it! — Jason Falls

The Practice: Shipping Creative Work by Seth Godin 

Clipped, quippy, thoughtful, memorable, zero fluff. I love books where you can open at a random page and, with zero context and minimal effort, feel a little smarter. That's The Practice in a nutshell. If you're looking for a prescriptive manual on how to be creative, this isn't it. If you're looking for a book that inspires you to be more creatively generous, pick this one up. It's a fast one! — Iona Holloway

The Lifestyle Investor: The 10 Commandments of Cash Flow Investing for Passive Income and Financial Freedom by Justin Donald

Ever wished you could generate passive income that would allow you to fund your ideal lifestyle? Most entrepreneurs are so focused on scaling their business to generate active income that they sometimes neglect to invest time learning how to create passive investment income. Justin Donald teaches the strategies and principles that helped him transition from entrepreneur to full-time investor, which provides a life of financial freedom. It's not as easy as it sounds, so this book is a must-read to get experienced insights on how to do it for yourself.  One of the reasons I recommend the book are the actual investments that Justin has in his portfolio, including how he negotiated and structured the deals. — Eric "ERock" Christopher

The Road Less Stupid: Advice from the Chairman of the Board by Keith Cunningham

Most entrepreneurs don’t have anyone around them to ask hard questions about them or the business. So when smart entrepreneurs make decisions without seeking counsel, they can make dumb, unnecessary, mistakes. If you want to improve your business, you need to improve the questions being asked (or considered). Since not every business owner can afford or has access to smart mentors, Keith’s book is full of great questions that will force an entrepreneur to really think about what’s really important. I read through it every summer. — Nigel Green

The Energy Switch: How Companies and Customers are Transforming the Electrical Grid and the Future of Power by Peter Kelly-Detwiler

Even businesses that don’t think they are related in any way to the energy business will learn from this book. In layman’s language, Kelly-Detwiler explains what’s really going on around us, which to me opened up a whole new way of not only looking at my business’ energy consumption, but also at ways to begin generating passive revenue from clever energy strategies that will also set up my company for long term savings. I was surprised by what’s possible now. — Wendy Keller

You Can't Teach a Kid to Ride a Bike at a Seminar: The Sandler Sales Institute's 7-Step System for Successful Selling by David H. Sandler and John Hayes PhD

When I assist entrepreneurs and startups, I always suggest this book. Sandler's straightforward techniques of properly selling have helped train the sales force for countless businesses and industries. While many new companies sometimes focus too much time and effort on building out the back office, processes, marketing and other areas, Sandler reminds us of the importance of selling and selling proficiently. — Adam Horlock

Drug Use for Grown-Ups: Chasing Liberty in the Land of Fear by Carl Hart
Columbia University professor of Carl Hart advances a radical and controversial idea: that most drugs are not inherently dangerous, and rather society has created a culture of danger around drug use by virtue of its being illegal, stigmatized and criminalized. Not only can drug use be safe, Hart argues, but when done responsibly, can actually lead to a happier and more productive life. Hart supports his thesis with both research and personal experience, poking holes in the pervasive ideology behind the “war on drugs” that the U.S. government has been waging for decades. Regardless of their personal habits around the consumption of illicit substances, readers will undoubtedly learn a new thing or two about psychology and history from Drug Use for Grown-Ups. — Danielle Sabrina

Mentor to Millions: Secrets of Success In Business, Relationships, and Beyond by Kevin Harrington and Mark Timm
Every entrepreneur should read this best-selling book written by Shark Tank's Kevin Harrington and Mark Timm to learn about the power and importance of . If you want to get somewhere faster, stop trying to do everything on your own. A mentor can more importantly help you learn how to win in business and in every area in life. — J.J. Hebert

In the Company of Women: Inspiration and Advice from over 100 Makers, Artists, and Entrepreneurs by Grace Bonney

This is an incredible collection of more than 100 stories of women from so many different backgrounds and abilities who all work for themselves; architects, chefs, hoteliers, media titans, tattoo artists and more. I love reading about fashion legends like Eileen Fisher and about those who are just launching their careers. It’s an incredible source of inspiration, with these women sharing the mistakes they have made, the lessons they have learned and what they are most proud of.  — Mita Mallick

Think Again by Adam Grant
 
Grant's book reminded us how we often only want to know what we want to know. Many entrepreneurs, including myself, start something out of passion, assumptions, and beliefs that we are confident in. But often, realities require us to REthink about those assumptions and beliefs. It is the highly calibrated confidence that ignites intellectual curiosity and the joy of questioning. The kind of thrill was exactly what I had when I intentionally went against almost every single piece of advice a fashion consultant who cost me $8,000 gave me. I was not self-sabotaging. On the contrary, I was rethinking and decided to destabilize stereotypes and cookie-cutting approaches to building a fashion brand. Grant's book will give you the psychological tools you need to an updated and reopened mind towards your business and your life. — Elle Wang, Ph.D.
 


Podcasts

Image credit: My Favorite Murder

My Favorite Murder, hosted by Georgia Hardstark and Karen Kilgariff

In the world of podcasts, true crime is a saturated field, but My Favorite Murder sets itself apart from the rest. The hosts’ synergy and propensity for banter make you feel like an active participant in an engaging conversation among old friends rather than an external listener. Importantly, Georgia and Karen don’t just relay the macabre details of the crimes they describe, but also look for the social implications behind them, which are often as relevant today as ever. They’ve also cultivated a veritable community around the (the members of which are called “Murderinos”), which is one of the major reasons why My Favorite Murder has been among the most popular true-crime podcasts and outlets for audible escapism since its inception in 2016. — Danielle Sabrina

Climbing Gold, hosted by Alex Honnold 

Alex Honnold is "that guy" who climbed El Capitan, the 3,000-foot-high sheer granite monolith in Yosemite National Park, with bare hands and no rope. While his 2017 feat was a little unrelatable for mere mortals, his new-ish podcast, Climbing Gold, is the opposite. With powerful throughlines on creativity and bravery, episodes are jammed full with fascinating guests and laser-beam insights with a nice sprinkling of humor to set everything off. Even if you know nothing about climbing, you'll struggle not to be inspired by the stories of people who defined climbing culture and pushed out the boundaries of what was considered possible. (The "Invisible Chord" episode was my favorite.) — Iona Holloway

Your First Thousand Clients, hosted by Mitch Russo

Mitch Russo achieved legendary status when he led a company he co-owned with Anthony Robbins and Chet Holmes.  Now he’s the host of a compelling, don’t-miss-an-episode business podcast. Podcasts are not generally my thing, but Mitch has access to a level of guest that most others only dream about, and his clear, concise focus on business building by generating clients helps me and probably other owners think about their strategies for client attraction in supremely unique and cutting-edge ways.  I find myself taking notes while I’m listening and configuring how I can adapt his genius and his guests’ to my business’ growth. Brilliant. Worth every second. — Wendy Keller

Social Geek Radio, Various Shows hosted by Jack Monson

Monson, one of my favorite podcasters, actually does a few different shows focusing on the franchise industry. He knows everyone and gets some of the top franchise players in the industry to come on as guests, including CEOs, marketing experts, authors and many others. Monson himself works in franchising and attends industry events all year long, so he really has his ear on the ground to what’s happening. And unlike a lot of business podcast hosts who are really there to promote their own services, Monson keeps it about the guest. He’s very conversational and has a voice made for radio and podcasting, so it’s always an informative and engaging listen. — Scott Greenberg

The Deep End, hosted by Marshall Kosloff 
In-depth conversations with leaders in industry, art, politics, technology, science, education and more help illuminate creativity, critical thinking and success. Explore what creates successful seed rounds for health tech startups. Find out what goes into a mayoral campaign in the greatest city in the world. Learn how an independent media company outpaces its own goals in record time. Hosted by Marshall Kosloff, The Deep End produces long-form podcast content that's engaging, intelligent and compelling. If you're intrigued by deep dives into ideas that matter, The Deep End is a podcast you'll want to explore. — John Boitnott

Hidden Brain, hosted by Shankur Vedantam

While Hidden Brain is one of the most popular podcasts out there, I personally can't wait for each new episode because it satisfies an intellectual fetish for me: Understanding how people think. The insights about why people behave the way they do is extremely useful for anyone trying to understand their customers better. It's not always focused on business, but it is focused on consumer behavior, which is critical. — Jason Falls

Related: Top 25 Business Podcasts for Entrepreneurs

Streaming TV Series

Image credit: Michele K. Short/HBO

Younger, available on Hulu

I was absolutely obsessed with this show, which follows a woman in her 40s as she pretends to be a millenial to get a job at a publishing house. As someone who previously ran a self-publishing business, I found it fascinating. I mean, are you really an entrepreneur if you don't watch TV and create businesses at the same time?! If you want a glimpse into book publishing and the stilts it's currently standing on, absolutely watch this Hilary Duff-starring gem. — Gabrielle Garrett

Mare of Easttown, available on HBO Max

This crime drama stars Kate Winslet as a small-town detective investigating a local murder. The limited series is a reminder of how we all endure and can survive rejection, loss and grief. It unfolds in an America that doesn’t often get highlighted, an unglamourous community where poverty and the opioid crisis are chipping away at families. Winslet herself summed it up best in a New York Times interview,, describing what draws us to the main character:  “She's a fully functioning, flawed woman with a body and a face that moves in a way that is synonymous with her age and her life and where she comes from. I think we're starved of that a bit.” — Mita Mallick

Abstract: The Art of Design, available on Netflix  

Every entrepreneur needs to at least have an appreciation for and understanding of design, in all its forms. This series (two seasons in so far) looks at design in all its various forms (architecture, furniture, art, user experience) which helps us understand how the right design can actually lead to better business success. It is one of the most informative shows I've ever watched. — Jason Falls

Shrill, available on Hulu

Historically in movies and TV, overweight women are portrayed either as laughable (think “Fat Amy” from the Pitch Perfect saga) or evil (think Ursula from The Little Mermaid). Aidy Bryant’s Shrill provides viewers with a long-overdue reprieve from this hackneyed media trope. The sharp, biting comedy chronicles the day-to-day life of Annie, a young Portland-based journalist, and offers a fresh perspective that elevates a plus-size woman’s story rather than reviles it. Bolstered by tight writing as well as a brilliant and diverse supporting cast, Shrill hilariously and often poignantly captures the struggles of being an unapologetically fat woman in America. — Danielle Sabrina

Suits, available on Amazon Prime Video

Truthfully, I don’t watch much TV, but Suits is an all-time favorite show of mine. The series follows the lives of two corporate lawyers in New York City, Harvey and Mike. Harvey, Mike's boss, is revered by some as one of the best closers in the city. In some ways, he represents the qualities of a successful entrepreneur; he's cunning, confident and adept at his craft. Harvey is unapologetic about who he is, which I find admirable and refreshing. Ultimately, I think there's something that any young businessperson can learn from unconventional thinking, and Suits portrays this perfectly. — Ryan McGrath

Workin' Moms, available on Netflix 

I rarely laugh out loud at anything that isn't British; Workin' Moms is the exception. The humor is so dry and dark it makes everything pucker. I am not a mom, but I see pieces of myself in every slightly bedraggled, imperfect, messy, brilliant woman on this Canadian sitcom. If you're over the perfectly curated presentation of "the working woman," you'll feel very seen by this series. It's fun to watch the head of a PR company stealing the creative concepts for "Rat Girl" from a toddler, or watch as a mother who wrote a book on parenting fails to spot her daughter boarding the Quanon train because she's away on a podcast tour. The only disappointing part is that episodes are 23 minutes long. Seasons disappear into all-to-thin air. — Iona Holloway

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