Checking In With Stephen Cloobeck

Book Origins and Core Philosophy

• The book, Checking In, is structured around Klubeck's personal and business journey, emphasizing that its lessons apply to any industry.
• The core philosophy is "checking in," defined by the mantra: "Be sweet, have compassion, and take care of your team."
• Klubeck argues that protecting employees from abusive customers builds "tremendous team trust," creating a reciprocal culture where the team protects the company's standards.
• The book contains one intentional error regarding Klubeck's education: it claims he attended UCLA, whereas he actually attended USC, Harvard, and Brandeis.
• Klubeck views dyslexia as a "gift" for entrepreneurs, noting that many great leaders are dyslexic and rely on oral communication rather than reading and writing.
• He attributes his success in complex areas like science, IT, and finance to a photographic memory for numbers and data, rather than traditional business education.

Business Operations and Management Decisions

• Klubeck built a real-time IT system allowing him to view operational numbers every three to four minutes across 420 properties in 35 countries.
• His acquisition strategy involves buying broken companies, operating on the principle that getting "80% of the way there" is sufficient if the final 20% can be fixed later.
• He advocates for a "settle, settle, move on" philosophy in contract disputes to avoid costly litigation and preserve business relationships.
• Klubeck maintains a "gentleman's handshake" as a primary contract enforcement tool, relying on trust and communication rather than excessive legal detail.
• He enforces a "zero-tolerance" policy for finger-pointing, having terminated employees who shifted blame rather than taking responsibility.
• As a leader, Klubeck insists on raising his hand to take responsibility for any failure within the organization, refusing to allow others to do so.
• He hired Diamond Resorts' current President and CEO, Mike Plasky, based on a 30-to-45-minute interview, prioritizing gut instinct over extensive due diligence.
• Klubeck implemented strict communication rules for executives inherited from a failing public company, requiring a 24-hour response time to all internal and guest inquiries.
• He established a "Global Address List" (GAL) mandating that all staff provide home phone numbers to ensure 24/7 command and control access.
• He fired a resort manager at 3:00 AM for refusing to answer his phone, setting a precedent that leadership requires absolute availability.
• Conversely, Klubeck personally paid for the funeral of a front desk clerk's deceased son using his own credit card to demonstrate deep empathy and care.
• He created a "Do Not Come Back" list, famously ejecting a guest from a property for using a slur against a staff member, a practice Klubeck notes was revolutionary in the industry at the time.
• He introduced the "Meaning of Yes" concept, giving guests the right to a full refund even for faults they did not cause to build long-term loyalty.
• Klubeck placed his personal business card with his live phone number and email at every front desk, receiving 600 emails daily to force accountability across his management team.
• He implemented a salary cut for all executives, including himself, during the 2008 financial crisis; every executive chose to stay rather than leave.
• He transitioned his business model to a cash-based system during the 2008 crisis when securitization lines vanished, allowing the company to survive while competitors failed.
• Klubeck bought multiple distressed hospitality competitors during the 2008 downturn at prices of one times EBITDA or less.
• He terminated an operations executive who walked away from a $1.2 million retention bonus during the crisis, viewing it as a lack of loyalty.

Industry Trends, Workforce, and Technology

• Klubeck critiques the hospitality industry's over-reliance on technology, citing examples of poor customer service in telecommunications, academia, and politics.
• He identifies the hospitality industry as "mark-to-market every day," making it uniquely difficult due to daily customer dependency.
• He believes the future workforce will complement AI and big data rather than compete with it, maintaining that personal interaction and eye contact are irreplaceable in sales.
• Klubeck disagrees with the narrative that Millennials are hard to manage, citing examples of 18-year-old sales associates who are aggressive and effective.
• He notes a shift in consumer behavior where Millennials prefer not to own assets (like retail or homes) and are driving demand for apartment living over traditional retail.
• Klubeck suggests real estate developers should convert large retail boxes into apartments to adapt to changing ownership preferences.
• He believes the nature of employment has changed due to technology disintermediating tasks like scheduling and letter writing, allowing for leaner teams.

Reputation, Media, and Public Service

• Klubeck participated in the "Undercover Boss" reality show twice, a unique distinction, to elevate the brand and build a human connection with the public.
• During the first taping, he quit after one day due to heat and lack of water but returned after an intervention with the producer.
• He altered the show's standard format by revealing his identity in an outdoor setting (a beach house) rather than a boardroom to avoid pre-packaged charity tropes.
• Klubeck's improvised gesture of paying a worker's $150,000 mortgage became a viral moment that significantly improved Diamond Resorts' brand reputation.
• He argues that a company's reputation is more valuable than its branding or marketing efforts, as reputation is defined by external perception.
• Klubeck led a corporate collaboration to plant palm trees along the Las Vegas Strip, securing a petition signed by 80% of the Strip's businesses to bypass public hearings.
• He created "Brand USA," a public-private partnership to market the US as a tourist destination, relying on non-partisan relationships with both Democratic and Republican leaders.
• Klubeck criticizes the current political climate for threatening the decline in international visitation, which he estimates costs the US "billions and billions of dollars."
• He has engaged in direct, confrontational advocacy on Twitter against politicians he perceives as hostile to hospitality and public-private partnerships.
• Klubeck expresses a desire to implement pragmatic governance reforms if elected governor, including removing bureaucratic lines at the DMV and redefining gun control debates.
• He identifies himself as a pragmatic Republican who crosses aisle lines to achieve results, noting that he has earned the right to speak bluntly to leaders due to his contributions.