” If everyone is going left, look right.” – Sam Zell
Sam Zell’s autobiography, Am I Being Too Subtle?, is as bold as the title suggests. Best known for his huge success in real estate—such as selling Equity Office to Blackstone for $39 billion in 2007—Zell sees himself as more than an investor. Zell is an entrepreneur who applied his skills to different industries. His unusual, contrarian approach has often become standard practice, leaving a lasting impact on many in the world of real-estate and investing.
The book begins with the story of his parents’ escape from Poland to Chicago during World War II. Their journey taught Zell the value of seeking good information, honesty, loyalty, and taking smart risks. These values became the foundation of his career.
Zell’s start in real estate came during college at the University of Michigan, where he managed student properties in exchange for free rent. From there, he rose to the top of the real estate ladder by buying properties others avoided, by improving and turning them into profitable investments. This earned him the nickname “Grave Dancer.” He also pioneered REITs and explored new markets.
Zell wasn’t just different in how he invested—he was unique in how he ran his businesses. He says he invented “business casual” and loved giving out themed T-shirts with slogans like “Stay Liquid.”
Zell also talks openly about his failures, like buying the Chicago Tribune. That deal led to bankruptcy a year later and damaged his reputation, which he valued highly. He also admits that his intense focus on business sometimes came at the expense of family life.
Lessons I Learned
Thinking Like an Entrepreneur
An entrepreneur sees not just the problems but the solutions too. They back their opinions and ideas with action and always reinvest in their business. Owners think long-term. Entrepreneurs must be comfortable with rejection and stay tenacious, believing there is always a way forward. Critical thinking is key, keeping them adaptable and moving ahead.
Dealing with Risk
Challenging conventional wisdom is valuable, but it is crucial to understand the risks and downsides of this approach. The first step in making any deal is calculating the downside. Taking risks is essential for consistently achieving above-average returns. Experience sharpens your ability to assess risk. To manage risk, simplify your goals and steps, as well as gather all available information.
Be Unique, Be Yourself
If you’re great at what you do, you have the freedom to be who you are. Choose authenticity over conformity. Always stay true to yourself.
Reputation
It’s not just what you do that matters, but how you do it. Reputation is a major asset. Being fair, kind, and giving back earns you loyal friends you can trust. There will be times when you need to rely on others.
Thinking Differently
People often get caught up in unwritten social rules. Don’t be afraid to stand out; fitting in isn’t always important. Doing things the same way as everyone else hinders progress. Bold, new ideas can become the norm over time. Think critically, and expose yourself to new people, places, and businesses to avoid getting stuck in your ways. And don’t take yourself too seriously—you need to stay grounded to avoid being swept up by success.
Positive Mindset
Highs and lows are part of any journey. When considering an investment, ask, “How bad can it get?” but also remember to ask, “How good can it get?” You can still fail even if you make the best decision with the information you have. Failure isn’t in Sam Zell’s vocabulary. Dream big, hope high, and work to make it happen. If you have strong conviction, don’t accept defeat. Anything is possible. When you don’t see limits, you’re free to keep trying.
Information Can Save Your Life
Being a good listener has immense value. Gather opinions from everyone, seek clarity, and then choose your own path. If someone offers valuable information, take it into account.
Business
The basics of business come down to supply and demand, cash flow, solid governance, good partners, cost control, and scale. Business is like a puzzle to solve. Limited competition is irreplaceable, even if you’re a genius. Competition skews judgment and increases costs. Where there is scarcity, price doesn’t matter. Respect simplicity. Reinvest in your business. Involve your team in risk-taking to align everyone with a shared goal. Not following the crowd lets you keep cash reserves to act when the time is right. Speed and certainty win deals. A board should be a source of valuable advice, not just a formality. Spotting trends leads to great opportunities. Invest in quality assets with room for improvement below replacement cost. Holding an asset means choosing to buy it every day.
People
The people around you play a huge role in your success. An irreplaceable business partner is invaluable. Listening helps you understand what truly matters to others, and you can learn a lot from them. Trust comes from being honest and competent.
Do What You’re Good At
If you understand something well, you should be able to sum it up on a single piece of paper. Focus on what you do best and let others handle the rest. That’s how you create the most value.