Lessons from Donald Trump

Donald Trump, a figure known for his extensive career in real estate and business prior to his presidency, has authored several books and given numerous interviews sharing his philosophies on deal-making, management, and investment. His approach is often characterized by bold and direct strategies.

On Business

On Big Thinking: "I like thinking big. I always have. To me it’s very simple: if you’re going to be thinking anyway, you might as well think big." [1]
- Learning: This foundational principle encourages ambition and setting high goals from the outset.
On Passion: "Without passion, you don't have energy, without energy you have nothing." [2]
- Learning: Energy and passion are presented as essential drivers for achieving significant accomplishments in the business world. [2]
On Persistence: "Sometimes by losing a battle you find a new way to win the war." [3][4]
- Learning: Setbacks can provide valuable lessons and lead to alternative, ultimately successful, strategies. [3]
On Action: "Get going. Move forward. Aim High. Plan a takeoff. Don't just sit on the runway and hope someone will come along and push the airplane. It simply won't happen." [5]
- Learning: Proactive effort is non-negotiable for success; one must initiate action rather than waiting for opportunities to be presented.
On Winners and Losers: "What separates the winners from the losers is how a person reacts to each new twist of fate." [3][6]
- Learning: The ability to adapt and respond effectively to unforeseen circumstances is a key determinant of success. [2]
On Motivation: "Money was never a big motivation for me, except as a way to keep score. The real excitement is playing the game." [1][4]
- Learning: Viewing business as a game can be a powerful motivator, with money being a measure of success rather than the ultimate goal.
On Accomplishment: "In the end, you're measured not by how much you undertake, but by what you finally accomplish." [3][6]
- Learning: The focus should be on delivering results rather than simply being busy with numerous projects.
On Instinct: "Experience taught me a few things. One is to listen to your gut, no matter how good something sounds on paper." [7][8]
- Learning: Intuition, honed by experience, can be a more reliable guide than purely analytical assessments. [9]
On Knowledge: "Watch, listen and learn. You can't know it all yourself. Anyone who thinks they do is destined for mediocrity." [2][7]
- Learning: Continuous learning and humility are crucial for avoiding complacency and achieving excellence.
On Branding: "Your business, and your brand, must first let people know what you care about, and that you care about them." [3]
- Learning: A successful brand is built on a clear message of purpose and a connection with the customer. [10]
On Taking Risks: "Criticism is easier to take when you realize that the only people who aren't criticized are those who don't take risks." [2][3]
- Learning: Criticism is an inherent part of taking the risks necessary for significant achievements.
On Leadership: "Leaders, true leaders, take responsibility for the success of the team, and understand that they must also take responsibility for the failure." [3]
- Learning: True leadership involves accountability for both positive and negative outcomes.
On Perseverance: "Part of being a winner is knowing when enough is enough. Sometimes you have to give up the fight and walk away, and move on to something that's more productive." [7][8]
- Learning: Strategic retreat can be a winning move if it allows you to redirect your energy toward more fruitful endeavors.
On Delivering Value: "You can't con people, at least not for long. You can create excitement, you can do wonderful promotion and get all kinds of press, and you can throw in a little hyperbole. But if you don't deliver the goods, people will eventually catch on." [1]
- Learning: Substance and quality are paramount; marketing and hype are unsustainable without a solid product.
On Work-Life Balance: "If you're interested in 'balancing' work and pleasure, stop trying to balance them. Instead, make your work more pleasurable." [2][11]
- Learning: Finding enjoyment in your work can be a more effective strategy than trying to strictly separate and balance professional and personal life.
On Focus: "I like to think of the word FOCUS as Follow One Course Until Successful." [2]
- Learning: Sustained concentration on a single objective is a powerful path to achieving it.
On Ego: "Show me someone without an ego, and I'll show you a loser." [5]
- Learning: A healthy sense of self-esteem and ambition is presented as a prerequisite for success.
On Goals: "Remember, there's no such thing as an unrealistic goal–just unrealistic time frames." [3][4]
- Learning: Ambitious goals are achievable with a realistic and flexible approach to timing.
On Luck: "Everything in life is luck." [3][8]
- Learning: Acknowledging the role of chance can be a part of a business mindset.
On Cost Management: "I believe in spending what you have to. But I also believe in not spending more than you should." [1]
- Learning: Prudent financial management is key—invest where necessary but avoid unnecessary expenditures.

On Real Estate

On Location: "Perhaps the most misunderstood concept in all of real estate is that the key to success is location, location, location…First of all, you don't necessarily need the best location. What you need is the best deal." [1]
- Learning: A good deal can be more valuable than a prime location, challenging the traditional real estate mantra.
On the Nature of Real Estate: "It's tangible, it's solid, it's beautiful. It's artistic, from my standpoint, and I just love real estate." [7][12]
- Learning: A deep appreciation for the physical and aesthetic aspects of property can be a driving force in this industry.
On Buying Right: "you make your money in real estate when you buy it, not when you sell it." [13]
- Learning: The profit potential of a real estate investment is largely determined at the point of purchase.
On Investment Strategy: "Sometimes your best investments are the ones you don't make." [3][5]
- Learning: Prudence and the willingness to walk away from a seemingly good opportunity are crucial for long-term investment success.
On Market Knowledge: "I don't hire a lot of number-crunchers, and I don't trust fancy marketing surveys. I do my own surveys and draw my own conclusions." [1][3]
- Learning: Direct, personal market research can provide more valuable insights than relying solely on third-party data. [9]
On Buying at a Low Price: "I don't believe you can ever get hurt by buying a good location at a low price." [11]
- Learning: Securing a good property in a desirable area for a low price is a formula for minimizing risk.
On Sticking to What You Know: "you're generally better off sticking with what you know." [7][8]
- Learning: Specialization and deep knowledge in a particular area of the market can be a significant advantage.
On Enthusiasm in a Deal: "I couldn't sell him on my experience or my accomplishment, so instead I sold him on my energy and enthusiasm." [8]
- Learning: When lacking a track record, passion and drive can be persuasive assets in convincing others to invest in your vision.
On the Art of Real Estate: "Business is an art, whether it's real estate or anything else. Treat it that way by developing your technique, being tenacious and remaining passionate." [11]
- Learning: Viewing real estate as a craft encourages a focus on skill development, persistence, and passion.
On Wasting Time in Real Estate: "Real estate is all about wasting time. The more time you waste, the more money you make." [14]
- Learning: This counterintuitive advice suggests that patience and careful deliberation before making a move in real estate can lead to better financial outcomes.

On Negotiation

On 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." [1][9]
- Learning: Never appear desperate. Strength in negotiation comes from having options and being willing to walk away. [15]
On Creating Leverage: "Leverage is having something the other guy wants. Or better yet, needs. Or best of all, simply can't do without." [9]
- Learning: The key to leverage is identifying and controlling something that is of high value to the other party.
Plan for the Worst: "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." [1]
- Learning: A defensive strategy that prepares for the worst-case scenario provides a strong foundation for a negotiation. [16]
On Flexibility: "I never get too attached to one deal or one approach… I keep a lot of balls in the air, because most deals fall out, no matter how promising they seem at first." [1][9]
- Learning: Pursuing multiple opportunities simultaneously prevents over-investment in any single deal and provides fallback options.
On Fighting Back: "When somebody challenges you, fight back. Be brutal, be tough." [2][4]
- Learning: A willingness to be confrontational and stand your ground is presented as a necessary tactic in competitive situations.
On the Art of the Deal: "Deals are my art form. Other people paint beautifully on canvas or write wonderful poetry. I like making deals, preferably big deals." [17][18]
- Learning: Approaching deal-making as a creative pursuit can foster a passion for the process.
On High Aims: "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." [8][19]
- Learning: Start with an ambitious goal and be relentless in your pursuit of it.
On Deprecating the Asset: "If you want to buy something, it's obviously in your best interest to convince the seller that what he's got isn't worth very much." [11][17]
- Learning: A negotiation tactic for buyers is to downplay the value of the asset to lower the seller's price expectation.
On Going to the Top: "You always do business with the very top, the best in the business, the richest, not the wasters at the bottom... Everyone under the top guy is just an employee. You need to go to the top guy and negotiate with him." [20]
- Learning: Deal directly with the ultimate decision-maker to avoid wasting time with intermediaries who lack authority.
On Being Outrageous: "If you are a little different, or a little outrageous, or if you do things that are bold or controversial, the press is going to write about you." [1][3]
- Learning: Unconventional tactics can generate media attention, which can be used as a form of leverage.
On Knowing When to Walk Away: "I am not afraid to walk away from a deal." [16]
- Learning: The willingness to abandon a negotiation is a powerful tool that gives you control. [16]
On Creating Urgency: By creating an artificial sense of urgency, you can compel the other side to act quickly, often leading them to make concessions to avoid losing the deal. [21]
- Learning: Time pressure can be a strategic element in negotiations.
On Anchoring with Extreme Offers: Starting negotiations with a bold, high-stakes proposal can shift the conversation toward your terms. [21]
- Learning: Your initial offer can frame the entire negotiation, so it's important to be strategic with it.
On Trust: "Never trust anyone in business. Nobody." [20]
- Learning: A skeptical and self-reliant approach is advised in business dealings.
On Information Gathering: "I am a great believer in asking everyone for an opinion before I make a decision. I ask, I ask, I ask until I begin get a gut feeling about something. And that's when I make a decision." [8]
- Learning: Gather extensive information from various sources to inform your intuition before making a final call.
On Denigrating Competition: "Sometimes, part of making a deal is denigrating your competition." [9]
- Learning: In a competitive environment, highlighting the weaknesses of your rivals can be a tactic to gain an advantage.
On Being Unpredictable: Unpredictability can keep negotiators on their toes, making it difficult for them to anticipate your next move and undermining their preparation. [21]
- Learning: Being strategically erratic can be a source of strength in a negotiation.
On Framing Outcomes: Consistently framing outcomes as "wins" or "losses" can motivate a team and align them behind a clear goal. [21]
- Learning: The language used to describe the goals of a negotiation can be a powerful motivational tool.
On the Genetic Component of Deal-Making: "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." [9]
- Learning: Trump's perspective is that the core talent for negotiation is innate rather than learned.
On the Importance of Personal Meetings: "No matter how tight your schedule or your clients' time, do your best to have face-to-face meetings. It is much easier to kill a 'faceless deal.'" [13]
- Learning: Personal interaction builds rapport and makes it more difficult for the other party to back out of a deal.

Learn more:

Lessons from Donald Trump

On Business

On Real Estate

On Negotiation

Written by Antoine Buteau

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