How Taking Calculated Chances Built a Business Empire | Michael S. Liebowitz - Serial Entrepreneur
Here are the top 10 key takeaways from Michael S. Liebowitz's interview that reveal how a fearless entrepreneur built multiple successful businesses through calculated risk-taking, strategic leadership, and an unwavering work ethic.
1. Work ethic trumps natural talent
Michael Liebowitz emphasizes that work ethic is the single most important factor for success. He doesn't consider himself the smartest person in the room, but believes nobody will outwork him. This mindset has been the foundation of his accomplishments throughout his career.
His approach to business involves complete dedication. While he acknowledges that people discuss work-life balance, he believes true success requires a life commitment, especially in fields like sales, brokerage, advisory, or when creating a business. This level of commitment becomes the differentiating factor between those who achieve extraordinary success and those who achieve only moderate success.
2. Making decisions based on people, not just numbers
Liebowitz strongly believes that success comes down to betting on the right people. He repeatedly states that "everything is a jockey bet," meaning the person leading the business is the most critical factor in its success. When evaluating opportunities, he prioritizes understanding who's in charge above all other considerations.
This philosophy extends to his investment decisions as well. He shares an example of investing in Meta when its stock price dropped dramatically, not because of the business model, but because he believes in Mark Zuckerberg's leadership and vision. Liebowitz summarizes this approach with the maxim: "You can't do a good deal with a bad guy, and you can't do a bad deal with a good guy." He trusts that the right person will find solutions regardless of business challenges.
3. The power of established brands
One of Liebowitz's most insightful observations is about the value of established brands. When discussing why he took the Douglas Elliman CEO role, he emphasizes how much easier it is to lead a company with an already established, internationally recognized brand rather than building one from scratch.
Having created his own brand in the insurance industry, he appreciates how challenging that process was. He describes joining Douglas Elliman as "starting on third base" because the brand recognition was already in place. This perspective offers an interesting counterpoint to the common entrepreneurial narrative of building everything from the ground up, suggesting that sometimes the smarter path might be leveraging existing brand equity.
4. Learning from failure builds resilience
Liebowitz challenges the notion that successful people avoid failure. He believes that successes are found within failures, and people who have experienced setbacks and recovered become more valuable. He shares a story about preferring to hire someone who had multiple business failures precisely because that person understood mistakes and how to avoid them.
This perspective reframes failure as an essential component of growth rather than something to be avoided. It suggests that resilience and the ability to learn from mistakes are more valuable traits than having a perfect track record. Liebowitz approaches failures with his father's wisdom: "There's a reason they put erasers on pencils" — acknowledging that mistakes are natural and expected parts of any journey.
5. The importance of staying hands-on as a leader
Liebowitz attributes much of his success to being deeply hands-on in his businesses. He makes reference to "A Bronx Tale," noting that being closely involved helps him spot problems early, comparing issues to cancer that must be caught early to prevent fatal outcomes. His approach involves direct communication with all levels of the organization.
In his current role at Douglas Elliman, he personally speaks with agents and employees daily, which has allowed him to identify and address long-standing issues that might have persisted for years. He believes this direct engagement is essential for understanding the real challenges facing the business. For leaders who aren't hands-on, Liebowitz suggests they should "go buy a company that makes tractors" instead, implying that certain businesses absolutely require this level of personal involvement.
6. Focusing on fundamentals drives stock performance
Rather than obsessing about stock prices directly, Liebowitz believes in focusing on fundamentals: treating agents well, supporting employees, and building a strong business. He contrasts this with private equity firms that constantly press for monthly numbers, creating pressure that ultimately undermines performance.
His philosophy is that stock price is a lagging indicator of success, not a leading one. When fundamentals are strong, stock performance naturally follows. This approach allows him to build sustainable value rather than chasing short-term market reactions. It also creates a healthier work environment where employees can focus on building the business rather than constantly worrying about market perceptions.
7. The value of being responsive and accessible
One habit Liebowitz picked up from observing successful people is the importance of being immediately responsive. He notes that even billionaires who don't "need" to be responsive still return calls and emails promptly. This approach builds relationships and creates opportunities that might otherwise be missed.
His accessibility extends to shareholders as well. He contrasts his approach with companies that avoid engaging with investors, noting that he's willing to speak with any shareholder regardless of how many shares they own. This openness not only builds trust but also potentially provides valuable insights that could benefit the company. Liebowitz sees this responsiveness as a simple habit that yields significant returns in business relationships.
8. Avoiding worry and managing anxiety
One of the most personal insights Liebowitz shares is about overcoming worry and anxiety. He spent years studying human behavior and psychology to better understand his own thoughts and reactions. Through this process, he developed techniques to manage anxiety that previously kept him up at night.
His advice for entrepreneurs struggling with anxiety includes meditation, exercise, and finding quiet moments to slow down the mind. He suggests even five minutes of meditation can provide "three more hours of power in your mind." Liebowitz's parting wisdom to his children would be simply: "Don't worry. Worrying is the worst thing you can do." He notes that no one on their deathbed wishes they had worried more.
9. The necessity of adapting business plans
Liebowitz stresses the importance of flexibility in business planning. During his nine weeks at Douglas Elliman, he notes that his business plan has changed fifteen times as he learns new information and meets different people within the company. He sees this adaptability as essential to effective leadership.
He cautions against rigidity, suggesting that only ego prevents leaders from changing course when necessary. This willingness to adapt extends to his approach to acquisitions and technology as well. Rather than building everything in-house, he recognizes that sometimes buying off-the-shelf solutions makes more sense in rapidly evolving markets. This pragmatic approach prioritizes outcomes over attachment to specific methods or plans.
10. The courage to say no
Throughout his career, Liebowitz has developed the discipline to say no to opportunities that don't meet his standards, even when they seem appealing. He notes that 90% of deals never make money, and successful entrepreneurs must be "the no guy" who can refuse enticing but fundamentally flawed opportunities.
This disciplined approach extends to his investment philosophy as well. Before considering potential returns, he always wants to understand the downside risks. This cautious evaluation prevents the emotional decision-making that often leads to poor investments. While acknowledging that business inherently involves risk, he believes in taking calculated chances based on thorough assessment rather than enthusiasm. This balance of optimism and pragmatism has been a hallmark of his entrepreneurial journey.