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A Political Kingmaker Reveals His Life Rules

Roger Stone mastered his political craft at the knee of impeached President Richard Nixon. He’s worked for several Republican presidential campaigns, spanning from Nixon to Trump, and waged a war of words against the Clintons. Needless to say, the man is hated by the left (which he views as a badge of honour), revered by many on the right, and questioned by centrists. He’s best known for his scrappiness in the political arena and becoming an entrepreneur by creating a lobbying firm with former business partner Paul Manafort, who is currently cooling his heels in a prison cell awaiting trial relating to a questionable investigation by special prosecutor Robert Mueller. To boot, Stone’s timeless style keeps him near the top of DC’s best dressed. Oh yeah, and he’s a former bodybuilder with a tattoo of Richard Nixon on his back…

Roger Stone Mixes Entrepreneurship with Politics

To label Roger Stone ‘controversial’ is putting it mildly. Maybe that’s why I find him to be a fascinating character. I feel that if I follow his activities long enough, something dramatic will happen or a salacious political scandal will be revealed (he dishes a lot of dirt).

Stone always seems to be in the middle of political scuffles, or at the very least has the inside scoop on the latest D.C. drama. He’s theatre for any political junkie, which is likely why the Netflix special about him, ‘Get Me Roger Stone,’ was a smashing success shortly after Trump was elected President. Stone has been friends with the President since the 80s and was one of the critical people who urged Trump to run.

To top it all off, Stone is a New York Times Bestselling Author… Which brings me to the point of this blog – his latest book. It’s called Stone’s Rules: How to Win at Politics, Business, and Style.

The book provides a unique perspective on life, one only a successful and cunning political lobbyist with decades of experience in Washington D.C. can articulate. Stone has a gusto for life in general, and specifically business and politics. The book is humorous, but also gives some novel and useful advice about entrepreneurship.

Of Roger Stone’s 140 rules to winning at politics, business and style I’ve pulled out three of my favorites:

Roger Stone’s 3 Best Rules For Entrepreneurs

1. The bigger the score, the longer the gestation: How true it is. Stone states, “True entrepreneurialism requires patience to achieve great wealth.” And the most lucrative deals, the ones with significant lifelong impact, are often highly complex and require countless hours of negotiations and iterations. If a deal is taking a long time to close, it’s most often worth the extra effort. 


2. Never hold a meeting unless you know what result you want out of the meeting: It’s incredible how many people will book a meeting without a set agenda and time limit. I’m surprised how much time busy people are willing to commit to a whimsical conversation during the workday. I think it’s because people, even some entrepreneurs, feel productive just merely being in a meeting.  

When booking your next meeting, know that many people inherently waste time. So have a purpose and a measurable outcome, with a set time limit, going into it. Just don’t be one of these schmucks who announces upon entering the meeting how limited they are on time – that’s just disrespectful.

One of my business partners in the past, a fantastic guy, was the worst to have meetings with. He would chat for two, sometimes three hours, basically killing an afternoon. And I’d leave the meeting with no measurable outcome. This went on for several months before I finally had enough and told him we can’t have meetings longer than 15 minutes. Inevitably the meetings still carried on for about 30 minutes, but they were more productive, and he learned to be sensitive to the clock on the wall. 

Stone states in his book, “A strong leader meticulously plans and methodically orchestrates meetings in order to achieve a desired result, or he doesn’t hold them.” 


3. If you are engaged in any business or profession, you are more likely to succeed if you are well dressed than if you are badly dressed: Fact. You are judged instantly by how you look. Don’t kid yourself. And it’s not vain. It’s human nature. This doesn’t mean you have to put on a three-piece suit for every meeting. What it means is you need to look sharp. I understand the casual attire commonly worn in meetings nowadays, but that doesn’t mean you don’t iron your shirt, wear well-fitting clothes and keep your hair in check. Know the audience you are meeting and dress to look the best, without showing much effort went into it. 

Stone accurately states, “An impression is made based on how you are dressed.”


Roger Stone’s latest book, Stone’s Rules: How to Win at Politics, Business and Style is a light but informative reminder of how politics and business work, and the nuances that get results. Whether you align with Stone’s political opinions or not, it’s a worthwhile read for any entrepreneur with a penchant for the inner-workings of politics. 

Stay hungry,





P.S. Politics and business go hand in hand in today’s economy. Subscribe to my free newsletter below to see how the latest political happenings could affect your investments and business. Stay informed.