500 Days In The Trump White House

Cliff Sims
Former White House Senior Aide

New York Times Best Selling Author of Team of Vipers

What’s it Like Working for President Trump?

The first honest insider’s account of the Trump administration. If you hate Trump, you need the truth; if you love Trump you also need the truth.” – excerpt from Cliff Sims’ book Team of Vipers


This episode is not about political beliefs or who you voted for in the last election. If you are looking for that, you are in the wrong place because this is as middle-of-the-road as it gets when it comes to political affiliation. However, it is the furthest thing from center when talking about the most powerful person in the world. This is a behind-the-scenes account of what makes President Donald Trump tick, what motivates him, and most importantly, gives us the method behind the madness from someone who sat at his right hand for 500 days.


Our guest this week on The Secrets to Winning is former White House Director of Message Strategy and New York Times Best Selling Author Cliff Sims. Recently, I sat down with Cliff at his new gig as President of Telegraph Creative to get a first-hand account of what really happened during his 500 days in the White House.


For Donald Trump, the greatest high he has ever experienced in his life was the night he was elected President. I was there. For him, the high of winning the Presidency has never been repeated by being the President.


After standing at Donald Trump’s side on Election Night, Sims soon joined him in the West Wing. He quickly found himself pulled into the President’s inner circle as a confidante, an errand boy, an advisor, a punching bag, and a friend. Sometimes all in the same conversation.


As a result, Sims gained unprecedented access to the President, sitting in on private meetings with key Congressional officials, world leaders, and top White House advisors. He saw how Trump handled the challenges of the office, and he learned how to view the world from the President’s perspective which allowed him to better understand the methods behind such a polarizing figure.


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For five hundred days, Sims also witnessed first-hand the infighting and leaking, the anger, joy, and recriminations. He had a role in some of the President’s biggest successes, and he shared the blame for some of his administration’s worst disasters. He gained key, often surprising insights into the players of the Trump West Wing, from Jared Kushner and John Kelly to Steve Bannon and Kellyanne Conway.


Throughout this conversation, we peel back the curtain on what makes the most powerful man in the world successful and what are his secrets to winning!



03:05 – What is President Trump’s Winning Formula?


04:30 – Why there is no “win-win” for Trump


06:30 – Does Trump have a moral compass?


07:50 – “Fire and fury the likes of which the world has never seen before”


 09:30 – Why Trump creates chaos in certain instances


12:30 – How in the world did this guy get elected as President of The United States?!


14:20 – Creating the messaging for the largest tax reform plan in American history


17:20 – The proof and optics behind why the most likable candidate always wins the Presidency


19:00 – Trump approaching the White House as the greatest stage on earth and why


20:10 – Why do people hate Trump so much?!


22:40 – What does Trump worry about? What keeps him up at night?


25:40 – When Trump began his Presidential campaign, did he actually believe he could win?


27:00 – What were the first words out of Trump’s mouth when he realized he was about to be elected?


27:55 – Was Trump’s work culture toxic?


28:35 – Insight into Cliff’s book, Team of Vipers


30:20 – Pros and cons of the diversity of opinion in the West Wing


33:20 – “Proximity to power is intoxicating”: How the White House was like the show Survivor


39:10 – How Cliff’s 500 days in the White House have changed him personally


41:00 – Story about Secretary of Defense Jim Mattis’ Personal Development Plan


45:00 – “You only know the world which you have been exposed to”


48:00 – Is there one thing that Cliff wishes Trump would do differently?


50:40 – Cliff’s conversation at the White House with Nick Saban after the National Championship visit


53:50 – Cliff’s observation of servant leadership from Clemson Head Coach Dabo Swinney


55:50 – The final call to action from Cliff Sims


There is no concept of ‘win-win’ with Trump. When you're a real estate guy in Manhattan, there is only so much real estate. It’s a zero-sum game. Either I get it or you get it. There are no deals. And he was going to do what it took to win.
Trump flouted norms, not laws. There is a big difference between those two.
Trump creates chaos because he bets that he is more comfortable in the chaos than whoever his adversary is.
“In negotiation, the quickest way you will lose is if you’re scared. And I ain’t scared.” – Trump on negotiations with North Korea
Trump adheres to a very smart brand philosophy which is: Your brand should piss somebody off because the worst thing you can be is vanilla.
The moment when Trump realized that he was going to be President of The United States, the first thing he said was ‘When I get to Washington, I’m going to shove it up John Kasich’s (blank)’

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