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The Art of the Deal by Donald Trump with Tony Schwartz

The Rabbit Hole is written by Blas Moros. To support, sign up for the newsletter, become a patron, and/or join The Latticework. Original Design by Thilo Konzok.

Key Takeaways
  1. Deals are my art form. Other people paint beautifully on canvas or write wonderful poetry. I like making deals, preferably big deals. That's how I get my kicks
  2. Most people are surprised by the way I work. I play it very loose. I don't carry a briefcase. I try not to schedule too many meetings. I leave my door open. You can't be too imaginative or entrepreneurial jd you've got too much structure. I prefer to come to work each day and just see what develops
  3. It never stops and I wouldn't have it any other way. I try to learn from the past, but I plan for the future by focusing exclusively on the pr sent. That's where the fun it. And if it can't be fun, what's the point?
  4. Sometimes it pays to be a little wild
  5. I don't hold it against people that have opposed me. I'm just looking to hire the best talent, whenever I can find it
  6. I hate la suits and depositions but the fact is that if you're right, you've got to take a stand, or people will walk all over you
  7. Sometimes - not often, but sometimes - less is more
  8. I always take calls from my kids, no matter what I'm doing
  9. I understand the game and while I don't like to play it, there is no graceful way out
  10. I'm not too big on parties because I can't stand small talk. Unfortunately they're a part of doing business so I find myself going to more than I'd like and then trying hard to leave early
  11. I like to keep as many options open as I can
  12. Ivana is one of the most organized people I know...she's almost as competitive as I am...I wouldn't bet against her
  13. I'm loyal to people who've done good work for me
  14. It just goes to show that it pays to move quickly and decisively when the time is right
  15. That experience taught me a few things. One is to listen to your gut, no matter how good something sounds on paper. The second is that you're generally better sticking with what you know. And the third is that sometimes your best investments are the ones you don't make
  16. My philosophy is to always hire the best from the best
  17. If the city won't approve something I think makes sense economically, I'll just wait for the next administration and try again
  18. Small details make all the difference in the look and ambiance of a building
  19. My style of deal making is quite simple and straightforward. I aim very high, and then I just keep pushing and pushing and pushing to get what I'm after. Sometimes I settle for less than I sought but in most cases I still end up with what I want
  20. More than anything else, I think Deal making is an ability you're born with. It's in the genes. I don't say that egotistically. It's not about being brilliant. It does take a certain intelligence, but mostly it's about instincts. Most people who do have the instincts will never recognize that they do because they don't have the courage or good fortune to discover their potential
  21. Trump Cards - deal making tips
    1. Think big - most people think small because most people are afraid of Success, afraid of making decisions, afraid of winning. And that gives people like me a great advantage. One of the keys to thinking big is total focus. I think of it almost as a controlled neurosis, which is a quality I've noticed in many highly successful entrepreneurs. They're obsessive, they're driven, they're single minded and sometimes they're almost maniacal, but it's all channeled into their work. Where other people are paralyzed by neurosis, the people in talking about are actually helped by it. I don't say this trait leads to a happier life, or a better life, but it's great when it comes to getting what you want
    2. Protect the downside and the upside will take care of itself - people think I'm a gambler. I've never gambled in my life. I happen to be very conservative in business I always go into the deal anticipating the worst. If you plan for the worst - if you can live with the worst - the good will always take care of itself. You can't be too greedy
    3. Maximize your options - never get too attached to one deal or one approach. Even if deals are made, I always come up with at least half a dozen approaches to making it work because anything can happen
    4. Know your market - I do my own surveys and draw my own conclusions. I don't hurt many number crunchers. I'm a great believer in asking everyone for an opinion before I make a decision. I ask and I ask and I ask until I begin to get a gut feeling about something. And that's when I make a decision. Another group I don't trust is critics as very few of them have any feeling for what the public wants
    5. Use your leverage - the worst thing you can possibly do in a deal is seem desperate to make it. That makes the other guy smell blood and then you're dead. The best thing you can do is deal from strength and leverage is the biggest strength you can have. Leverage is having something the other guy wants. Or better yet, needs. Or best of all, simply can't do without. It often takes salesmanship and imagination to come up with leverage
    6. Enhance your location - more than purely location, a great deal enhanced by promotion and marketing is the key
    7. Get the word out - hiring outside consultants is never as good as doing it yourself. Be straight with reporters, have bravado and play to peoples fantasies
    8. Fight back - if you believe in something deeply and people are obstructing you unjustly, fight back
    9. Deliver the goods - you can't con people, at least not for long. At some point you must deliver the goods
    10. Contain the costs - every dollar counts
    11. Have fun
  22. Father was a real estate developer as well and built low income and rent controlled housing in NY
  23. Almost boasts about the fact that he gave a teacher a black eye when he was in the second grade
  24. Learned to "finesse and manage" the drill instructor at the military academy
    1. Maybe shows some of the early innate manipulation or as Scott Adams says, hypnotic, powers that Trumpe exhibits
  25. His father was a great negotiator because he knew the price of everything and was always fair and reliable
  26. Clean and well maintained apartments are always worth the investment
  27. Finds ways to cleverly deal with people and situations - manager Irving great but stole so paid him a low salary and expected him to steal
    1. Seems like a temporary strategy which will only destroy cukture and hurt in the end
  28. You can't show fear. You have to stand your ground and whatever happens happens
  29. The simplest approach is often the most effective
  30. Early on I didn't have much but what I did have was the willingness to go after things that people even in a better position wouldn't consider seeking. I also couldn't sell people early on on my experience or accomplishments so I sold them on my energy and enthusiasm
  31. In the end, we won by wearing everyone else down. We never gave up and the opposition slowly began to melt away
  32. The city's desperate circumstances became my biggest weapon. I could act when others weren't willing and help the city get back on its feet
  33. If you're going to make a deal of any significance, you have to go to the top
  34. New manager at Grand Hyatt got Trump and his wife to leave them alone by being overly friendly and solicitous, asking for their opinion on every mundane decision
  35. Much more often than you'd think, sheer persistence is the difference between success and failure
  36. Regardless of industry, you want your customers to feel special
  37. I understand now that certain events can take on symbolic importance
  38. Controversy sells
  39. When you set the highest standards, they're expensive to maintain
  40. Good way to end a partnership on a classy note - "as with most things in life, time calls for change and it jd best to accept that fact. Nevertheless, I shall always be proud of my involvement in the creation of Trump Tower and finely remember how we worked to bring it about."
  41. I think it better to pay more for a sure thing
  42. There is always a buyer for the best
  43. I have a very simple rule when it comes to management: hire the best people from your competitors, pay them more than they were earning and give them bonuses and incentives based on their performance. That's how you build a first class operation
  44. You don't act on an impulse, even a charitable one, without considering the downside
  45. In any partnership, you're only as strong as your weakest link
  46. Committees and high priced consultants can't hold a candle to a group of guys with reasonable amount of common sense and their own money on the line
  47. My attitude is that you do your best and if it doesn't work, you move onto the next thing
  48. You're not measured by how much you undertake but by what you finally accomplish
  49. What I admire most are people who put themselves directly on the line
What I got out of it
  1. Some revealing insights from Trump how he thinks about business, life, competition. Some I thought were helpful but the vast majority show what I think is a "win/lose mindset" which isn't sustainable