Hopping over the Rabbit Hole

Hopping over the Rabbit Hole Plot Summary

Introduction

Have you ever faced a moment when your business seemed on the verge of collapse? When the market shifts beneath your feet, clients start disappearing, and the financial ground you once stood upon crumbles away? These critical junctures—these rabbit holes—define entrepreneurial journeys far more than moments of triumph. What separates successful entrepreneurs from the failed ones isn't avoiding these holes altogether, but rather developing the resilience and creativity to hop over them when they inevitably appear. The entrepreneurial path is fraught with uncertainty. Statistics tell us that half of all businesses fail within their first year, and a staggering 96% collapse before reaching their tenth anniversary. Yet amid these sobering odds, certain leaders consistently transform potential disasters into unexpected opportunities. They recognize that failure isn't final, but rather a pivotal moment of reinvention. Through intimate stories of near-catastrophe turned to triumph, readers will discover how the most resilient entrepreneurs embrace vulnerability, pivot quickly when strategies falter, and cultivate a mindset that transforms obstacles into opportunities. The journey reveals that success doesn't come from avoiding mistakes, but from responding to them with authenticity, boldness, and unwavering optimism—the true hallmarks of entrepreneurial resilience.

Chapter 1: The SALT Conference: Creating Opportunity in Crisis

"You may not realize it when it happens, but a kick in the teeth may be the best thing in the world for you." This quote from Walt Disney perfectly captures the entrepreneurial spirit behind the birth of the SALT Conference—a venture born from desperation during the depths of the 2008 financial crisis. It was March 2009. The S&P 500 had hit rock bottom. The world seemed on the verge of economic collapse. SkyBridge Capital, a hedge fund seeding business founded just four years earlier, faced an existential threat as redemptions flooded in. The founder and his partners knew that without a proactive, aggressive strategy, their company would soon become "NoBridge"—gone forever. In this moment of terror, a business partner approached with what seemed like an outlandish idea: throwing a hedge fund conference in Las Vegas at the height of the financial crisis, when most financial institutions were canceling events and cutting travel. "What if SkyBridge threw a hedge fund conference in Vegas?" the partner suggested. "We'll call it the SkyBridge Alternatives Conference, or 'SALT'." The founder was incredulous—a conference in Vegas during an economic meltdown? With clients fleeing and the business barely making payroll? It seemed absurd. But in that moment of crisis, the contrarian spark ignited. If the company didn't change direction, it wouldn't survive. Playing offense while everyone else played defense might be their only chance. With just two months to prepare, the team secured prominent speakers including Michael Milken and Steve Wynn, sold 500 registrations, and pulled off what would become the inaugural SALT Conference. Though initially underwater financially, the event positioned SkyBridge as optimistic industry leaders while everyone else retreated. More importantly, it connected the struggling firm with potential investors, managers, and partners who would ultimately help save the business. The SALT Conference teaches us a fundamental lesson in entrepreneurial resilience: crisis creates opportunity for those willing to see differently. When markets collapse and competitors retreat, bold entrepreneurs can gain market share, build relationships, and redefine their business model. This requires seeing beyond conventional wisdom and having the courage to act when others freeze. As the founder later reflected, they weren't merely trying to survive—they were sending a message of confidence and optimism when no government official or bank was willing to do so. This strategic pivot became a business-saving revelation. Rather than spiraling down the rabbit hole toward an illogical, nonsensical demise, they strategically took control of their future by embracing potential failure and transforming it into potential success. Sometimes, entrepreneurial salvation comes not from doing what seems logical, but from making the brave, contrarian move that others are too afraid to attempt.

Chapter 2: From Peril to Pivot: Acknowledging Mistakes and Moving Forward

"You don't learn by following rules. You learn by doing, and by falling over," said Sir Richard Branson. This philosophy was severely tested during SkyBridge's expansion into Asia, when a seemingly minor oversight nearly derailed years of hard work and reputation building. Victor Oviedo, a senior partner at SkyBridge, called with devastating news just three months before their planned 2014 SALT Asia Conference in Singapore. "Have you ever heard of Deepavali? The Festival of Lights? It's a holiday celebrated in Southeast Asia," he began ominously. The Monetary Authority of Singapore had just informed them that this major holiday had been rescheduled due to the lunar calendar—directly conflicting with the conference dates. After two successful years in Singapore, with speakers, sponsors, and venues already contracted, they faced a catastrophic scheduling error that threatened both the event and their relationship with Singaporean authorities. "How did we miss this?" the founder asked, dismayed. Victor sighed heavily. "Although it is no excuse, the observed holiday falls on a different day every year. We messed up. Plain and simple." This scheduling conflict was just one of several problems—Singapore had also discontinued its nonstop flight from the United States, potentially restricting North American participation. The situation looked dire. Rather than denying the mistake or shifting blame, the team made the difficult decision to respect the Monetary Authority's suggestion and postpone the event. "We need to pivot," the founder declared. "We need to adapt. It is time to brainstorm." Within hours, they had informed all stakeholders—the venue, confirmed speakers, sponsors, and media partners—of the postponement. But instead of surrendering to failure, by sunrise they had begun working on the SkyBridge Global Symposium. This pivot transformed potential disaster into opportunity. Rather than attempting a large conference in a challenging environment, they created an intimate, high-value symposium in Tokyo focused on 150 carefully selected Asian investors. In less than six weeks, they welcomed 120 institutional investors to hear former Federal Reserve Chairman Ben Bernanke and other investment icons speak. The format provided these potential clients with personal access to top financial minds while learning about SkyBridge's offerings—ultimately strengthening their position in the Asian market. This case illustrates three crucial principles for entrepreneurial resilience. First, identify mistakes and acknowledge errors promptly. As the founder noted, "You will never be able to move forward if you are unwilling to identify your mistakes, put your ego on the floor, and admit your failures." Transparency and honesty are essential to long-term success. Second, pivot decisively. After admitting a misstep, don't sulk or proceed stubbornly out of pride. Devise a strategic action plan to transform potential disaster into opportunity, distinguishing between "sunk costs" and "salvageable investments" that can be incorporated into your new direction. Finally, reflect and learn from the experience. "Mistakes and failures can be the most valuable resources for an entrepreneur," the founder observed. Success often glosses over weaknesses, while adversity exposes them and provides opportunity for growth. If you're not making mistakes, you're probably not pushing yourself far enough. The SkyBridge team turned what could have been an unmitigated disaster into a strategic opportunity because they followed this resilient playbook—acknowledge, pivot, and learn.

Chapter 3: Partnerships That Persevere: Building Trust Through Adversity

The email must have taken hours to craft. It was almost like an ancient text, with the "f-bomb" appearing in the exact same spot in each sentence. It concluded with the simple line: "You are a **** [insert four-letter word] and a lowlife." This masterpiece of profanity came from Eytan Sugarman, a business partner in a restaurant venture with the author, and signaled what appeared to be the end of their partnership. The two entrepreneurs had successfully launched Southern Hospitality, a barbecue restaurant with Justin Timberlake among its partners. Emboldened by this success, they had set out to open a second restaurant—the Hunt & Fish Club, a concept inspired by John Gotti's Bergen County Hunt & Fish Club. The problem was they were $500,000 short of the $3.5 million needed to open. The anxiety of entrepreneurship had caused them to project stress onto each other, pointing fingers and assigning blame. In a moment of frustration, the author had sent a passive-aggressive email detailing everything he perceived Eytan hadn't done. The response was the carefully crafted f-bomb masterpiece that arrived eight hours later. Usually, such an exchange would sever all ties, but something remarkable happened. After several deep breaths, the author did the most difficult but important thing in any relationship: he apologized. "Eytan, it's Anthony. I apologize. I was wrong. And I'd like to move forward if you are willing." Eytan accepted the apology, and they immediately buried the hatchet. This moment illustrated a fundamental truth about entrepreneurial partnerships: you can be right about everything, or you can be in a partnership—not both. In another illuminating partnership story, the author describes his relationship with Richard Howes of Australia's Challenger Life Company. After numerous conference calls, Richard had agreed to invest $200 million in SkyBridge's second seeding fund. But when they finally met in person to finalize the deal, Richard surprised him by saying, "I was expecting a short, fat, bald Italian guy!" The author responded with profanity and a grin, which broke the ice perfectly. Just three months later, as the 2008 financial crisis intensified, Richard called with what seemed like inevitable bad news. But instead of canceling the deal entirely, he reduced the commitment to $100 million—still a lifeline when SkyBridge desperately needed it. "Richard, from the bottom of my heart, thank you," the author responded. "You are a man of your word." Despite having only signed term sheets, Richard honored the agreement when most investors were fleeing the market. These experiences reveal three vital principles for successful partnerships. First, you don't need to be right all the time. The best relationships have reciprocity and find common ground when disagreements arise. Second, communication is key—people can't read minds, so having honest conversations, especially uncomfortable ones, is essential. Finally, relationships require constant work. As Stephen Lessing, a former managing director at Lehman Brothers, observed: "Relationships are never stagnant. They are always moving, either forward or backward." The author emphasizes that partnerships don't require best friendship, but they do demand mutual respect, honest communication, and the willingness to subordinate ego for the betterment of the business. In times of crisis, true character emerges. The people who honor agreements under imperfect circumstances are the ones you want beside you when challenges arise. These face-to-face relationships, built on trust and perseverance, often become the lifelines that save entrepreneurial ventures from catastrophe.

Chapter 4: Bold Marketing: Standing Out by Taking Calculated Risks

The assault boat hit the shore. The doors dropped and the bedlam of war began. The air turned pink as blood rained down. This wasn't a scene from a movie—it was D-Day, June 6, 1944, when the author's uncle Anthony Defeo stormed the beaches of Normandy as a 19-year-old soldier. Facing death at every turn, Uncle Tony made split-second decisions that saved hundreds of lives. After the war, he returned home to work at a local A&P supermarket for 40 years until retirement in 1990. What does this war story have to do with entrepreneurial marketing? Everything. Bold marketing requires the courage to make unconventional choices when competitors play it safe. The author illustrates this principle through several compelling examples, beginning with the Aflac duck. In 1990, when Daniel P. Amos became CEO of American Family Life Assurance Company, only 2% of Americans recognized the brand. After shortening the name to Aflac, Amos faced a crucial marketing decision between two ad concepts: a safe commercial with popular sitcom star Ray Romano, or a bizarre concept featuring a duck repeatedly quacking "Aflac." While the Romano ad tested reasonably well, with 20% recall, the duck commercial tested off the charts—everyone remembered it. Despite hesitation from his team, Amos chose the bolder option, debuting the Aflac duck on New Year's Day 2000. The results were astounding: web traffic skyrocketed, sales jumped 29% within a year, and name recognition soared 67% within two years. The seemingly ridiculous duck transformed the company's fortunes because Amos had the courage to make an unconventional choice. The author applied similar boldness at SkyBridge Capital, challenging the financial industry's tradition of avoiding press attention. "If you become a meaningful player in the industry, the press is going to cover you one way or another," he explains. "Define the narrative; don't let it define you." Rather than hiring PR firms to keep them out of the news, SkyBridge actively engaged media, sought out publicity, and created newsworthy events like the SALT Conference. This approach extended to unconventional marketing initiatives. Instead of traditional advertising, SkyBridge sponsored a public bike-sharing program in West Palm Beach and revived Wall Street Week, the iconic financial television show. "The competition is fierce," the author notes, "and at the end of the day, you need to convince someone why your firm is different and worth their money." The chapter concludes with four essential rules for bold marketing: First, get out there and talk to the press—shape your narrative rather than hiding from coverage. Second, focus on what makes you different—turn perceived weaknesses into strengths that distinguish you from competitors. Third, use nontraditional marketing tools to get your message out—create experiences that engage audiences in unexpected ways. Finally, take a portfolio manager's approach to marketing—diversify efforts across traditional and nontraditional strategies, recognizing that not every initiative will succeed. The lesson is clear: in crowded marketplaces, playing it safe is often the riskiest strategy. Like Uncle Tony on D-Day, entrepreneurs must sometimes make bold, counterintuitive decisions that others find too frightening. The companies that stand out aren't those with the biggest budgets, but those with the courage to market differently.

Chapter 5: The Negotiation Advantage: Leaving Money on the Table

"For all sad words of tongue or pen, the saddest of these: It might have been!" This quote from John Greenleaf Whittier captures the regret many feel after failed negotiations. When most people think about negotiating, they anticipate conflict—a zero-sum game where one person's gain is another's loss. However, the most successful entrepreneurs approach negotiations differently, seeing them as opportunities to build long-term, mutually beneficial relationships. The author describes three distinct approaches to business negotiations. First is the "Hammer & Chisel" approach—the old-school tactic of applying relentless pressure and intimidation to extract maximum value. People who thrive on this style are "hardwired for conflict and predisposed to enjoy psychological warfare," often becoming "rich but always miserable." The second approach comes from Roger Fisher, the late Harvard Law professor who taught the Harvard Negotiation Project and wrote Getting to Yes. Fisher advocated separating people from problems, focusing on interests rather than positions, and finding objective criteria for mutually beneficial outcomes. His concept of BATNA (Best Alternative to a Negotiated Agreement) helps negotiators understand their leverage and walkaway point. However, the author's preferred approach comes from Li Ka-shing, Asia's richest man with a net worth around $30 billion. Despite humble beginnings, Li built an empire based on a seemingly counterintuitive principle: always leave money on the table for your partners. "Creating partnerships and getting like-minded people to pull in the same direction is the smartest way to build a fortune," the author explains. "If you allow your partners to benefit handsomely from every deal, they will always come back and want to do business with you." This philosophy proved decisive when SkyBridge acquired Citigroup's Alternative Investments unit in 2010. After being bailed out during the financial crisis, Citigroup was divesting its hedge fund advisory, seeding, and fund of hedge funds units. For SkyBridge, then managing just over $1 billion in assets, acquiring Citigroup's $4.2 billion alternatives unit represented an extraordinary opportunity—if they could structure a deal that satisfied Citigroup's complex requirements. Citigroup wasn't simply seeking the highest bidder. They wanted someone who would preserve jobs, maintain performance for clients, and keep distribution agreements intact—essentially forming an arm's-length partnership rather than a traditional sale. Where other potential buyers took a hard-line approach, trying to extract maximum value, SkyBridge embraced Li Ka-shing's philosophy of mutual benefit. "In the end, despite several competing bids, we won out because of our willingness to give and take," the author recalls. SkyBridge made the senior Citigroup employees equity partners in the new organization, ensuring cultural integration and shared success. The transaction instantly quadrupled SkyBridge's size and transformed its trajectory. The lesson is clear: short-term transactional thinking rarely builds lasting success. By approaching negotiations with generosity and a long-term perspective, entrepreneurs create the trust and goodwill necessary for enduring partnerships. As the author concludes, "The man who tries to squeeze every last nickel is never truly happy... Don't look for the last nickel in a short-term one-sided transaction. Make sure both sides are winning when you are negotiating." This approach doesn't just produce better deals—it produces better relationships that become the foundation for future opportunities.

Chapter 6: Building the Right Team: Hiring Linemen, Not Quarterbacks

"There is no limit to what can be accomplished if it doesn't matter who gets the credit." This quote from Ralph Waldo Emerson perfectly captures the teamwork philosophy that transforms ordinary companies into extraordinary ones. The chapter opens with a vivid scene from the 1991 press conference before Super Bowl XXV, where New York Giants coach Bill Parcells was asked if his team could possibly stop the Buffalo Bills' high-powered offense. After an awkward silence, Parcells smiled and simply said, "If you can physically dominate, that's difficult for any opponent to deal with." His confidence came from understanding that great teams exceed the sum of their parts. Though lacking superstars, the Giants had built a cohesive unit where players sacrificed individual glory for collective success. They controlled the ball, avoided mistakes, and executed fundamentals perfectly—ultimately defeating the favored Bills. "Building a business is no different," the author explains. "You can take a team of modestly intelligent people and achieve more than the work of a group of extremely smart individuals pulling in different directions." At SkyBridge, this philosophy translated into a lean, adaptable organization where everyone contributed beyond their formal roles. When the annual SALT Conference approached, every employee pitched in regardless of position or seniority. The author shares four essential guidelines for building a winning team. First, get people physically close—what Michael Bloomberg called the "swamp tank" model. Rather than isolating executives in corner offices, SkyBridge's founder rarely used his office, preferring to sit among employees where he could "see and hear everything that's going on in order to keep my finger on the pulse of the performance, culture, and morale of the firm." Second, don't hesitate to remove toxic elements. "If you allow unethical behavior to become insidious within your organization, it becomes very hard to root out," the author warns. While admitting his own tendency toward leniency—"I'm a softie"—he learned that tolerating divisive personalities ultimately damages both the organization and the individual. As his friend Jim McCann, founder of 1-800-Flowers, advised: "I have never benefited from waiting to fire someone." Third, hire entrepreneurial people regardless of role. As Steve Jobs said, "The secret of my success is that we have gone to exceptional lengths to hire the best people in the world." At SkyBridge, the founder sought self-starters who could adapt to changing business conditions rather than rigidly following established procedures. In his words, "If you want to run a successful organization, you have to find things other than money to motivate your employees." Finally, learn from elite organizations—particularly the U.S. military. Through involvement with Business Executives for National Security (BENS), the author gained firsthand appreciation for military leadership principles. Service members embody moral exceptionalism, running toward danger while subordinating self for team and mission. "Complete subordination of self for the benefit of the team and mission? Check. Physically and mentally prepared beyond anything you could imagine? Check. Calm and assertive in the face of adversity? Check." The chapter's central message is that business success requires collective effort over individual brilliance. Like Parcells's Giants, the best companies aren't necessarily those with the most talent, but those that harness diverse abilities toward common goals. As the author concludes, "I can't imagine a better model to learn from in order to build a great business and foster a culture of collaboration and teamwork."

Chapter 7: Authentic Networking: The Triangle of Trust, Reciprocity, and Karma

"There is no royal road; you've got to work a good deal harder than most people want to work." This quote from Charles Wilson captures the essence of effective networking—not a shortcut to success, but a deliberate practice requiring authenticity and persistence. The chapter opens with a painfully relatable scene: a young, insecure professional at a Goldman Sachs networking event, too intimidated to make meaningful connections despite being surrounded by influential people. "By the end of the event, the number of contacts I made was a big fat zero," the author confesses about his younger self. Though he introduced himself to a few people, he gravitated toward familiar faces (mistake #1), talked strictly about business (mistake #2), and failed to hand out a single business card (mistake #3). That night, disappointed by his wasted opportunity, he promised himself to do better. For entrepreneurs, networking isn't optional—it's essential. "I owe everything I have built in my career to my ability to forge genuine, reciprocal relationships," the author explains. "Networking opens doors—both personally and professionally." Yet many professionals avoid networking out of fear, discomfort, or misconceptions about its purpose. The author offers practical strategies for effective networking, beginning with the courage to initiate contact. "Train yourself to go first," he advises. Rather than waiting for others to approach, overcome anxiety by making the first move with a simple introduction: "I'm Anthony Scaramucci. I work in equity sales. It's really nice to meet you." Most people feel equally uncomfortable in networking situations, so breaking the ice often brings mutual relief. Counter-intuitively, the author recommends avoiding business topics initially. "Conversations about work rarely allow you to build the kind of personal relationship that will grow and last," he explains. Instead, find common ground, meet in relaxed settings, and ask for advice—people love sharing expertise and feeling helpful. The core of authentic networking is what the author calls the "Triangle of Intimacy"—trust, reciprocity, and karma. Trust forms when people display vulnerability and authenticity. The author shares a deeply personal example when his daughter needed complex surgery for a tumor. By reaching out to a business acquaintance for medical referrals, he revealed vulnerability that deepened their relationship beyond transactions. Reciprocity, the second point of the triangle, involves mutual exchange—not necessarily financial equality, but effort from both parties. "The beginning of a reciprocal relationship requires one person to go first," the author notes. "If I do you a favor, you are much more likely to help me in the future." The final point, karma, means consistently treating people well regardless of their position. The author tells a remarkable story about developing a relationship with a Harvard Club waiter who later approached him about investing $35 million from a medical settlement. Though the author referred him elsewhere, the incident perfectly illustrated his principle: "Everywhere you go in life, leave a trail of good karma. Litter the world with people for whom you have done favors without expecting anything in return." Throughout the chapter, the author confronts the insecurities that often hinder networking—the feeling of not belonging or measuring up to others. He shares his own journey from anxiety-ridden junior employee to confident professional, realizing that "everybody's shit stinks" and "we're all the same." This democratic attitude enables authentic connections across status lines, allowing entrepreneurs to build the relationships that sustain them through inevitable challenges. The networking philosophy presented here isn't about collecting business cards or manufacturing false rapport. It's about genuine human connection—being your authentic self while helping others achieve their goals. As the author concludes, "If you can embrace the fact that people are equal, you'll enjoy life and be more successful. You won't feel intimidated. You'll meet more people. You'll feel more confident."

Summary

The entrepreneurial journey isn't about avoiding rabbit holes—it's about developing the resilience, creativity and vision to hop over them when they inevitably appear. The most successful entrepreneurs transform potential disasters into opportunities by acknowledging mistakes promptly, pivoting decisively, and building relationships based on authentic trust and mutual benefit. They approach negotiations with generosity rather than greed, assemble teams that prioritize collective success over individual glory, and network with genuine curiosity about others rather than self-promotion. When facing your own entrepreneurial challenges, remember that bold action in times of crisis often yields unexpected rewards. Don't hide from mistakes—acknowledge them quickly and use them as catalysts for reinvention. Build partnerships where both sides win, and resist the temptation to extract every last dollar from transactions. Create a team culture where humble collaboration trumps ego, and approach networking as a practice of giving rather than taking. Most importantly, believe in your own ability to overcome obstacles. As one entrepreneur discovered through his daughter's triumph over stage fright: "At the end of the day, I know that I am enough." That confidence—the belief that you possess the resilience to overcome whatever challenges arise—is perhaps the entrepreneur's most valuable asset.

About Author

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Anthony Scaramucci

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.

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