Hopping over the Rabbit Hole: How Entrepreneurs Turn Failure into Success

by Anthony Scaramucci, Peter Diamandis (Foreword), Tony Robbins (Introduction)

Develop the Scaramucci mindset that drives entrepreneurial success Hopping over the Rabbit Hole chronicles the rise, fall, and resurgence of SkyBridge Capital founder Anthony Scaramucci, giving you a primer on how to thrive in an unpredictable business environment. The sheer number of American success stories has created a false impression that becoming an entrepreneur is a can't-miss endeavor--but nothing could be further from the truth. In the real world, an entrepreneur batting .150 goes directly to the Hall of Fame. Things happen. You make a bad hire, a bad strategic decision, or suffer the consequences of an unforeseen market crash. You can't control what happens to your business, but you can absolutely control how you react, and how you turn bumps in the road into ramps to the sky. Anthony Scaramucci has been there and done that, again and again, and has ultimately come out on top; in this book, he shares what he wishes he knew then.

Your chances of becoming an overnight billionaire are approximately the same as your chances of being signed to the NBA. Success is hard work, and anxiety, and tiny hiccups that can turn into disaster with a single misstep. This book shows you how to use adversity to your ultimate advantage, and build the skills you need to respond effectively to the unexpected.


Learn how to deal with unforeseen events Map a strategic backup plan, and then a backup-backup plan Train yourself to react in the most productive way Internalize the lessons learned by a leader in entrepreneurship For every 23-year-old billionaire who just created a new way to send a picture on a phone, there are countless others who have failed, and failed miserably. Hopping over the Rabbit Hole gives you the skills, insight, and mindset you need to be one of the winners.

Genres: Business, Self Help, Entrepreneurship, Nonfiction, Management

208 pages, Hardcover

Published October 31, 2016

About the author

Anthony Scaramucci is an American financier, entrepreneur and political figure. He is the founder and co-managing partner of SkyBridge Capital, a global alternative investments firm.
As part of the first generation of his family to attend college, Scaramucci graduated from the Tufts University and Harvard Law School before embarking on a successful career in the financial services industry. In November 2016, Scaramucci was named to President-Elect Trump’s Presdential Transition Team Executive Committee. In June 2017, he was named the Chief Strategy Officer of the Export-Import Bank. He served as the White House Communications Director for 11 days in July 2017.
In 2016, Scaramucci was ranked #85 in Worth Magazine’s Power 100: The Most Powerful People in Global Finance. In 2011, he received Ernst & Young’s “Entrepreneur of the Year-New York” Award in the Financial Services category. He is a member of the Committee on Foreign Relations (CFR).
Scaramucci was born and raised on Long Island, New York, where he still resides today.

Reviews

[Jaak Ennuste · Rating 3 out of 5]

The only thing I knew about Scaramucci was that he was Trump's press secretary for 10 days. It is easy to form an opinion from such thin evidence.

Reading his book changed my mind about him (there was not much needed, since I knew so little). In the end, Hopping over the Rabbit Hole is another business book that provides guidance on how to build a team and a business. Still, there are original insights, and the author is more candid than the average entrepreneur-turned-author. Anthony owns up to his mistakes and admits when he wasn't good enough. In the end, the message is that everyone feels that way, but few are willing to power through.

Scaramucci ran an investment firm, but you almost couldn't tell from reading the book. There is virtually nothing about how to be an asset manager. Most lessons are about building relationships and a strong brand. What does that say about fund management in general? Nonetheless, he found out what he was good at, and he stuck with it.

Hopping over the Rabbit Hole is an easy and entertaining read. His story might provide you a few ideas on how to experiment or take advantage of failures in your own company.

[Page · Rating 1 out of 5]

Scaramucci is a key Trump advisor who wants to get rid of Wall Street regulations and financial advisor rules to put the client first so he and his hedge fund/investment banking buddies can go back to fucking over the average American and our economy.

[John of Canada · Rating 3 out of 5]

More of a motivational type book than a description of how he did things.The second half was much more interesting.He explained in a few paragraphs why president Trump does and says a lot of the things that he does and says.

[Nicholas Desantis · Rating 4 out of 5]

Better than expected. Good read for anyone trying to better their career.

[Ietrio · Rating 1 out of 5]

The first red flag: the long introduction. An introduction that does not really speak about the contents, but rather gives social proof about the author.

The second red flag: flaunting the experience.

In the end it is a stereotype story about the old man talking how audacious he was when young and how he overcame the problems in miraculous ways. If you take this as some sort of a biography, it might be passable. As a story "how entrepreneurs" do something, it's a waste of paper.

[M P Waller · Rating 5 out of 5]

Excellent - inspirational, informative, and pragmatic from the heart of somebody who walks the talk

This is an easy read packed full of practical solid advice and words of wisdom from somebody who is walking the talk and already accomplished a great deal. There are many many "big questions" touched on, answered with an authentic vulnerability to teach and educate the reader - that all entrepreneurs ask at some point on their journey; and this book gives back to those who follow along the path - in the true spirit of taking your passion and making your journey to a better outcome, less risky and more fun - by taking practical guidance and learnings from an already accomplished entrepreneur.

This book is written almost in the style and spirit of "writing this to my younger self" if I had the knowledge experience and hindsight I have now - what would I want to know at the start of my journey. For this reason it's probably one of the most valuable reads anybody on the path but with more to do - can take something - a little or a lot from.

[Naomi · Rating 3 out of 5]

As a new entrepreneur, but a long time MBA/business person, I had mixed feelings about this book. A chunk of this stuff was no brainer to me. That is not to say that I didn't do a whole lot of highlighting in it, but I didn't feel like I walked away feeling satisfied with paying for a $20 business book. I must admit that another thing that irked me was that the author used personal experience more heavily in the book vs. true business lessons. He also focused on using his own experience vs. bringing in others who have been in turnaround or preventative measures. This is definitely a book that is read and will simply go into my business library never to be cracked open again. My suggestion...get it from your library first. If it is a winner for you, then buy it.

[Fabian · Rating 3 out of 5]

Nothing new when it comes to business knowledge for me personally. That doesn’t not mean that the book is bad at all rather that the principles in this book are echoed by many entrepreneurship that went trough the hardships of building a business from nothing.

[GreenTieRationalist · Rating 5 out of 5]

Fantastic!

Short and sweet.

Both enjoyable and insightful

[An Nguyen · Rating 4 out of 5]

In Hopping Over the Rabbit Hole, Anthony Scaramucci, founder of SkyBridge Capital and host of the SALT Conference, offers an inside look at the rollercoaster world of entrepreneurship, finance, and resilience. The book’s central idea is that success isn’t about avoiding failure—it’s about surviving it. Scaramucci uses his own experiences—his early career at Goldman Sachs, founding and losing companies, and rebuilding stronger—to illustrate how persistence and adaptability matter more than perfection.

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Key Lessons & Takeaways

1. Embrace Setbacks as Part of the Process

Entrepreneurs inevitably fall into “rabbit holes” of failure, fear, and uncertainty. The key is learning to hop over them—by facing mistakes head-on, extracting lessons, and moving forward without ego.

2. Reinvention Is the Secret Weapon

Scaramucci emphasizes the importance of evolution in business. Industries change fast, and those who cling to old models or identities get left behind. Reinvent yourself and your business before the market forces you to.

3. Culture Over Everything

Building a strong company culture—where employees feel valued, empowered, and aligned—is more important than chasing short-term profits. Sustainable success depends on trust and shared purpose.

4. Stay Humble, Stay Hungry

Scaramucci reminds readers that humility and curiosity are essential for long-term success. Confidence must be balanced with openness to feedback, and even failures can fuel future breakthroughs.

5. Emotional Intelligence Beats Technical Skill

In leadership and investing alike, emotional awareness—how you react to stress, how you treat people, how you recover—often determines who wins when things get chaotic.

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Why It Works

✅ Engaging storytelling with real-world business lessons
✅ Practical mindset advice drawn from high-stakes experiences
✅ Encourages resilience and authenticity in leadership
✅ Balanced mix of finance, psychology, and personal reflection

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Weaknesses

❌ Some anecdotes focus heavily on Scaramucci’s own career and can feel self-promotional
❌ Less tactical “how-to” content for readers seeking specific entrepreneurial frameworks

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Final Verdict

Hopping Over the Rabbit Hole is a motivational, fast-paced read for entrepreneurs and professionals navigating volatile industries. Scaramucci delivers an honest message: failure is inevitable—but it’s not final. What separates winners from quitters is the ability to learn, adapt, and keep hopping.

[Quinns Pheh]

As an entrepreneur, you are far more likely to end up going out of business than you are to be a huge success. However, there are plenty of things you could perform to increase your chances of making a name for yourself. According to this book, these include adapting to dire situations, taking personal responsibility for your actions, assembling a high-quality team, and fostering your relationship-building skills. Above all, believe fervently that you really can succeed. Also, make use of unconventional marketing strategies. This book encourages you to determine the factors that set you and your business apart from your competitors. Do not be afraid to challenge the status quo.

[Zhivko Kabaivanov · Rating 4 out of 5]

Hopping over the Rabbit Hole (2020) is an honest, straight-talking look at what it takes to be a successful entrepreneur. The brutal truth is that the vast majority of businesses fail – yet many budding entrepreneurs still operate with their rose-tinted glasses firmly in place. But by following a few crucial tips – drawn from a successful business career with its fair share of mistakes – you’ll be more likely to survive, rather than succumb to failure.

[Chintushig Tumenbayar · Rating 3 out of 5]

Итали гаралтай Антони, Америкд өсөж өндийж эдийн засгийн өндөр мэдлэг эзэмшсэн ч ажил карьер нь нэг л амжилттай болж өгөхгүй л байлаа. Үнийгээ өөрийн алдаа нь дээрэс үндэслэн бусдад ойлгуулах сэнхрүүлэх тал дээр агуулга болгон бичжээ. Энэ номноос баг хамт олноо хэрхэн бүрдүүлэх тал дээр хэд хэдэн perspective таниж авлаа.

[Bhanu · Rating 4 out of 5]

"Rabbit holes are inevitable. It's how you hop over them that will define your success."

Anthony Scaramucci is the founder of SkyBridge Capital and briefly served as the White House Director of Communications. In his candid book, he shares his lessons and inspires you to pursue entrepreneurship.

[Ivan Kuznetsov · Rating 2 out of 5]

Poor content, style and attitude.

[Mariano · Rating 4 out of 5]

It started very strong but quickly tailed off. I wish he wrote more about his struggles in the business.

[Girish Shivakumar · Rating 4 out of 5]

Candid account of failures and how he turns them around - a real entrepreneur story.

[Kei · Rating 5 out of 5]

https://glasp.co/books/p/hopping-over...

[MEHEDI HASAN · Rating 5 out of 5]

I really enjoyed it! Shared some insights which is really important not only in maneuvering business but also in managing personal life!
Loved it.

[The 99th Edition · Rating 4 out of 5]

Blinkist
Brilliantly stacked up actionable life advice.
A maybe to re-read in full.