Richard Jenrette was a North Carolina boy who made good. 

Born in Raleigh in 1929 – just before the stock market crash that brought on the Great Depression – to an insurance salesman and his gardening wife, Jenrette went to the University of North Carolina at Chapel Hill, known then as Carolina. After a stint in counterintelligence during the Korean War, he headed to Harvard Business School, and the rest is both a stunning success story and American financial history. In 1959, he and two other Harvard Business School grads founded the first American brokerage firm to sprout since the Great Depression and took it into the financial stratosphere. 

Along the way, he collected, preserved and lavishly restored more than a dozen of our nation’s finest historic homes, including Ayr Mount outside Hillsborough, North Carolina, and the Roper House in Charleston, South Carolina, where he died earlier this year at 89. He was a meticulous and disciplined record-keeper and left behind a handwritten list of 24 rules of what he had learned about success and living a long and happy life. The rules were first shared with those who attended an intimate service for family and friends shortly after Jenrette’s death. 

    It is hard to argue about someone who apparently achieved both great success and happiness, goals deeply held by most human beings no matter our situations in life. Here are Jenrette’s rules, distilled through the lens of his well-lived life. 

1. Stay in the game. That’s often all you need to do – don’t quit. Stick around! Don’t be a quitter! 

2. Don’t burn bridges (behind you). 

3. Remember – Life has no blessing like a good friend! You can’t get enough of them. Don’t leave old friends behind – you may need them. 

4. Try to be nice. And say “thank you” a lot. 

5. Stay informed. Keep learning. 

6. Study – stay educated. Do your homework. Keep learning. 

7. Cultivate friends of all ages – especially younger. 

8. Run scared – overprepare. 

9. Be proud – no Uriah Heep for you – but not conceited. Know your own worth. 

10. Plan ahead but be prepared to allow for change when opportunity presents itself. 

11. Turn problems into opportunities. Very often it can be done. Problems create opportunities for change – people (should be) willing to consider change when there are problems. 

12. Present yourself well. Clean, clean-shaven, dress “classically” to age. Beware style trends. Look for charm. (Use) good grammar. Don’t swear so much – it’s not cute. 

13. But be open to change – don’t be stuck in the mud. Be willing to consider what’s new, but don’t blindly follow it. USE YOUR HEAD – COMMON SENSE. 

14. Have some fun – but not all the time! 

15. Be on the side of the angels. Wear the white hat. 

16. Have a fallback position. Heir and the spare. Don’t leave all your money in one place. 

17. Learn a foreign language. 

18. Travel a lot – around the world, if possible. 

19. Don’t criticize someone in front of others. 

20. Don’t forget to praise a job well done – but don’t praise a poor job. 

21. I don’t like to lose – but don’t be a poor loser if you do. 

22. It helps to have someone to love who loves you (not just sex). 

23. Keep your standards high in all you do. 

24. Look for the big picture, but don’t forget the small details. 

Dick Jenrette was not known as the “last gentleman of Wall Street” for no reason. 

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