In The Trenches

A Letter to President Trump

Published on January 23, 2017 Back to blog

Dear President Trump,

Congratulations on becoming the 45th President of the United States. I know that you worked very hard to win and I’m certain that you’ll continue to work hard in the days, months and years ahead.

Admittedly, I didn’t vote for you. But I believe in the democratic system and, regardless of that whole popular vote and Russia thing that everyone is talking about, you won. So now, I can only hope that you will guide America toward the prosperity, equality and security that I think you believe in. Some of your entertaining tweets and remarks may seemingly contradict those beliefs, but maybe that’s because the entertainer side of you hasn’t yet been fully balanced with the new Presidential side of you. I can only imagine how different your life is becoming. 

I heard that President Obama left you a very thoughtful letter as he vacated the White House. But, I also thought it may be helpful to share some advice from a tax-paying (federal and state) small business owner and non-profit CEO here in Boston who has been fascinated by your business and, now political, success for many years. I hope you take a moment to consider these tips.  

1. Words Matter – I know you enjoy the Twitter thing and love to communicate in short, provocative and unfiltered sound bites. Some of the things you’ve said have obviously (I pray) been grossly misinterpreted, while others were never intended for the public. However, now that the entire world, including our children, is hanging on your every word, I ask that you please consider your words carefully. They all matter. And, as President they will have much greater implications than they had in the Apprentice board room (which, by the way, was always very entertaining. Thanks!). 

2. Wealth is not synonymous with intelligence, experience or integrity – You clearly have a very impressive and wealthy group of friends and colleagues. Maybe some of them will even make huge contributions to shelter the homeless, feed the poor, create educational opportunities or lower costs of healthcare. However, as you consider who to listen to for advice and guidance, please put wealth aside and judge them on their merit. There are a lot of brilliant, experienced and wise people in our country (spanning all genders, races and religions) who could provide sound guidance.

3. Winning isn’t everything – Don’t get me wrong. I like to win as much as the next guy. But winning just for the sake of winning doesn’t do anyone any good. A blow-out isn’t always necessary (even Belichick will pull Brady out of the game when a win is secured). And, it’s also nice when everyone wins. (Although, I’m sure you’re with me on that whole “ participation trophy” thing at kids sports competitions. Right?). So, while I know you’re focused on winning, let’s try to make it as mutual for everyone as possible and only pick battles that really matter for America. 

4. It’s OK to put others first – In your inaugural address, you were very clear about putting America first. I think you meant that your #1 job is to make sure America is strong. However, as noted earlier, words matter – I’m not sure everyone took it that way. I’m sure that you agree that it’s OK (and commendable) to put others first sometimes. Not only is it the right thing, but it’s often the best thing. Let’s be sure that we have what we need, but please do not be excessive to the detriment of others. We do well when others do well (in America and beyond). 

5. No one likes a bully – I can’t tell you how happy I was to hear that your lovely wife, Melania, was going to take on Internet bullying as her cause as the First Lady of The United States. This is such an important and relevant topic in today’s day and age. It hurts when people say mean, untrue or harmful things about you – and it can potentially cause backlash when large groups of people are offended. I look forward to watching you and Melania set a new high standard for this one and put an end to this problem.

Thanks for taking the time out of your busy day to read this, as I know you have lots of important things to do, people to see and tweets to post. I hope that this advice is helpful. Just think, if you do a great job as US President, Ivanka would be in a great position to be not only the first female president, but also the first Jewish president. Now, that would be amazing, right?

Take care!

Jeff Freedman, CEO, Small Army (Storytellers for confident brands) and Small Army for a Cause (creators of the Be Bold, Be Bald! annual cancer fundraiser) 

PS. I couldn’t send this email without commenting on your amazing hair. It’s impressive, especially for a man of your age. That said, I would love to see you go bald with me on Oct 20 to show solidarity with those who battle cancer and raise money to help the fight. I’m not asking you to shave your head – just put on a bald cap and go about the day as usual. The event is called Be Bold Be Bald! and we’d be honored to have your support. Just let me know the best place to send your bald cap (i.e., White House, Trump Tower, Mar-a-Lago) and I’ll get a bunch out to you (for you and your entire family and staff) right away. Or, feel free to stop by our offices in Boston anytime.