12 Lessons I Learned From Donald Trump

12 Lessons I Learned From Donald Trump


I’ve already written about Donald Trump once this year…part of it had to do with his initial splash as a potential GOP Presidential nominee. The rest of it centered on how the stock market reacts to what is referred to as the presidential cycle.

I’m still not a believer that any President wields enough power or influence to change the underlying tide of the U.S. economy. However, election season has a special way of shedding light on the raw emotions of America. Donald Trump has gone from what many considered a political side show to striking a nerve in America and becoming a formidable contender.

Part of Trump’s appeal is his success and zeal as a business leader and entrepreneur. Rather than getting political, I’ll stick to my comfort zone and discuss what I learned during my Apprentice days with the Donald (back in 2004) and the ensuing years following the show, staying in contact with the Trump Organization.

Here are a dozen business lessons that we can all learn from The Donald:

1. The importance of being a great communicator. Being a great communicator takes a certain level of empathy and understanding of your audience. It also takes a great level of honesty and resolve to speak your mind, and Trump is certainly not lacking in either of these areas. He is undoubtedly one of the “great communicators of our time.”

2. Avoid singular dependency. No one is in Trump’s pocket (unlike most politicians). In business, Trump began as a real estate behemoth, but he has diversified well beyond his core real estate business. He now has a presence across multiple industries including golf courses, resorts, casinos, both high end and middle tier real estate, retail, media, model management, book and magazine publishing, etc. This level of diversification gives him a sort of self-reliance vs. dependency on one industry, lender, or segment of the market place.

3. Know and believe in your brand. No one does this better than Donald Trump. While the rose marble, gold monikers, pink ties, luxury real estate, and a prominent hairdo may not be your idea of style, they’ve served Trump well. His sense of personal and business swagger is unmistakable and identifiable. For this Trump is unapologetic. This can certainly work against you, but for Trump this conviction in his own brand has catapulted his success.

4. Be decisive and have a strong conviction in your own principles. This is the underlying foundation for any business owner. Behind every great success lies a set of core values and guiding principles that help shape every decision.

5. Have the courage to take calculated risks. Trump’s success (and billions) isn’t by accident. Yes, he was given a healthy start at a young age due to his father’s success and yes, he lived a relatively privileged lifestyle. But instead of squandering any money he’d been given or taking it for granted, he took risks and built on it. A great example is his first big deal in which he took Manhattan’s highly unprofitable Commodore Hotel and transformed it into the still thriving Grand Hyatt, adjacent to Grand Central Station. Deals like that don’t get done on a whim and don’t become profitable without taking a calculated risk.

6. Surround yourself with excellence. Trump always talks about this network of the best and brightest. He is friends with Carl Icahn, the recently deceased Ace Greenburg, and many others who were and are great business leaders of our time.

7. Have a deep understanding of the legal system and business environment. Trump is famous for lawsuits and several corporate (not personal) bankruptcy filings. While this isn’t necessarily a great thing, his in-depth knowledge of the legal system has undoubtedly helped him out. Like any good business owner he has a solid understanding of business laws, tax codes, etc.

8. Be flexible and open to new ideas. This can be summed up pretty easily: “Hey, Donald, let’s do a TV show called The Apprentice?!”

9. Understand the economy, debt, and healthcare. These are important topics that any business owner, particularly one who basically runs his own empire, should know. Trump needs to know how the economy can affect his different businesses, to the upside and to the downside. He’s got to deal with healthcare for his employees, how to manage debt for his golf courses and real estate deals, and human resources issues that are impacted by all of the above.

10. Why you need to be branding and communicating 24/7. I have to wonder if Trump ever sleeps. If he does, it’s probably not too much. Like other uber successful business leaders of our time like Larry and Sergey from Google, Trump’s steam never seems to run out.

11. Don’t cry over spilled milk- learn from failure. Business doesn’t always comes easy and there will be let downs, even for Donald Trump. He’s had casinos that have shut down, The Apprentice didn’t last forever, he’s been involved in some famous lawsuits, and the United States Football League (USFL) didn’t work. But in true Trump style, he picked himself up, brushed himself off, and refused to let these speed bumps stop him.

12. Love, love, love what you do. And last, but certainly not least – love, love, love what you do. No one can argue with this. Donald Trump loves what he does and it shows. I call this “harness what you have.” It’s marrying your love for an industry or market with your inherent skill set as a business person, whether it’s sales, analytics, creative writing, or finances. If you love what you do and are fully engaged in your business, the possibilities are endless.

I have a feeling Donald Trump isn’t going away anytime soon…

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