Entrepreneurial lessons from Donald Trump

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...and 3 lessons they shouldn’t!

Love him or hate him, Donald Trump has always been a polarizing figure. As a real estate mogul, businessman, and now 45th president of the United States, there’s a lot to learn from Trump.

After all, he’s accomplished the seemingly impossible.

At the same time, Trump has made more than his fair share of mistakes. So, here are the lessons, as well as mistakes, that entrepreneurs should learn from Trump…

1. Establish your brand early

Throughout his career as a businessman, reality show star, and politician, Donald Trump has done an excellent job of branding himself. His name in gold lettering is synonymous with hotels and real estate. He had his own catchphrase. And, those red “Make America Great Again” hats helped spread his political message and set him apart from the other candidates.

Like Trump, all entrepreneurs need to develop a strong branding strategy to gain traction, set themselves apart from competitors, and prove that they’re an authority figure in the industry.

2. Be confident

If there’s one thing that we can all agree on when it comes to Trump, it’s that he’s extremely confident in himself. In fact, Trump is the epitome of believing in oneself. He believed that he was going to change the skyline of New York City. Trump believed that was going to win the 2016 presidential election. Even when people said this was impossible, Trump had so much confidence — that he proved otherwise to everyone.

Being an entrepreneur means overcoming self-doubt and not listening to the naysayers. When you wake up every morning knowing that you’re going to succeed, even if it’s accomplishing a small goal like gaining 10 new email subscribers, you will take your success to a whole new level.

3. Patience and persistence

In the early 1990s, Trump was in trouble. He was some $9 million in debt and was forced to go into bankruptcy. Did those setbacks end his career? Obviously not. Instead of throwing in the towel, Trump kept going forward through patience and persistence. And, he came back stronger. As he once said, “Sometimes by losing a battle you find a new way to win the war.”

Losing a battle in your startup or business could be one of the most valuable lessons that entrepreneurs need to learn. You’re going to have setbacks. You’re going to fail. Instead of reverting to your comfort zone and giving up, you need to learn from these mistakes so that you can bounce back every time — and sometimes even better than before.

That doesn’t mean Trump is a role model for everything. Here are three Trump mistakes entrepreneurs should learn from…

1. Letting your ego run the show

Confidence is a good thing. But, too much of it can be a bad thing. As Jeffrey Kluger, author of The Narcissist Next Door: Understanding the Monster in Your Family, in Your Office, in Your Bed — in Your World, writes:

The problem with being Trump is the same thing that explains the enormous fame and success of Trump: a naked neediness, a certain shamelessness, an insatiable hunger to be the largest, loudest, most honkingly conspicuous presence in any room — the great, braying Trumpness of Trump — and that’s probably far less of a reveal than it seems.

Kluger adds that instead of using superlatives, Trump’s products should speak for themselves. “If it can’t, maybe it ain’t so great.” There’s also the compulsive promotion of his name. “There is no GatesWare software, no; it’s not Zuckerbook you log onto a dozen times a day.” And, that’s not even diving into the public feuds and never admitting that you’re wrong.

Successful entrepreneurs aren’t just aware of their strengths and accomplishments. They’re also conscious of their weaknesses, failures and they own up to their mistakes. They admit when they don’t know something. And, they consider the point of views of others.

2. Doubling down on bad bets

Entrepreneurs know when to fight and when to walk away. That’s not necessarily something that Donald Trump knows how to do. For example, when Univision canceled plans to air the Miss USA pageant in 2015, because of the disparaging comments Trump made about Mexican immigrants, Trump should have apologized and moved on. Instead, he decided to sue Univision and continue the feud. It was a PR nightmare and was another example of his ego getting in the way.

3. Going crazy on social media

Social media can be a great tool to interact with customers, exchange ideas with influencers, keep your audience up-to-date, and spread your brand awareness. However, badly used it’s also distracting, damages your reputation and severs relationships with customers and investors.

As you know, Trump is more than obsessed with Twitter. He’s had public feuds and seems to be more worried about Saturday Night Live’s ratings than running the country.

Again, Twitter is a great medium, but sometimes you just need to take a step back from it and focus on developing the best products and services around. Trump may do well to let a PR person tweet for him — PR style, for once. But then, that takes us back to No. 1 of the mistakes of Trump, and we probably won’t see those changes anytime soon.

Keep in mind that you can learn just as much from a poor example as you can from a good example. Watch, really watch, as the next few years roll past. When you notice a gigantic Trumptonian mistake — and you know we will see them — ask yourself, “How can I apply this knowledge to my business or my new startup?”

You may have more guidance for your business at this time in history than you ever will have again.

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Meet the Author

John Rampton

John Rampton


Rampton is an entrepreneur and connector who advises several companies in the Bay Area.


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