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Do You Have the ‘Street Smarts’ To Be Extremely Successful?

Do You Have the ‘Street Smarts’ To Be Extremely Successful?

January 05, 2024


  • The ability to read others and negotiate skillfully can have a major impact on your success.
  • Low cunning is one “street smart” technique to use when doing a deal or agreement.
  • Perspective, purpose, preparation and process drive your results.

There’s no question that a good education and ongoing learning can equate to greater success and wealth over time.

Consider that the average yearly salary for workers with a bachelor’s degree is $64,896, compared with $77,844 for master’s degree holders—and $96,772 for those with a professional degree, according to the U.S. Bureau of Labor Statistics. Some fields do ever better, of course. The average American with a newly minted PhD in engineering, math or science can expect to make slightly over $100,000 a year to start.

That said, if you want to generate significant wealth, you might consider spending as much time “reading people” as you do reading books and studies. In our experience working with the Super Rich—those with a net worth of at least $500 million—we find that their outsized success usually requires another ingredient: street smarts.

In most cases, we find the Super Rich weren’t the valedictorians of their schools—often they weren’t even the honor students. That’s not to say they’re not intelligent. They most certainly are. But they’re not typically the genius, rocket scientist types who use academic learning to get ahead.

Instead, it’s street smarts and common sense—which we find to be actually quite uncommon—that do the most to enable them to amass great fortunes. Indeed, quite a few of the self-made Super Rich are real-world-savvy people who earned C’s as students—or even dropped out.

The upshot: Don’t discount the power of street smarts on your journey toward significant success and wealth. Four key aspects of street smarts So what does it mean to be street-smart? The self-made Super Rich, through determination and practice, have a keen ability to understand people and leverage that understanding to achieve big results in business situations. For example:

  • They are adept at sizing up business situations accurately and quickly.
  • They listen well but have an independent point of view.
  • They are acutely aware of their goals and are evaluating ways to achieve them.
  • Most important, the self-made Super Rich recognize the angles and know how to adeptly work them.

For example, street-smart entrepreneurs have a keen understanding of what everyone involved in a business situation wants and is looking to achieve. Those goals and motivations might be different from what the various parties say they want as outcomes. In business dealings, the players don’t always say what they mean or mean what they say—and the self made Super Rich tend to see through any such facade.

That said, they know how to best use book smarts. They commonly see intellectual technocrats and professionals as highly useful partners and resources—people who serve a particular function by providing specialized expertise. The street-smart Super Rich credit book smarts for their mastery of a sophisticated topic, which is why they hire these experts. However, to the street-smart, book smarts are commodities and are interchangeable. There’s no single best mergers and acquisitions lawyer, for instance. There are many exceptional mergers and acquisitions lawyers. The same holds true for every type of book smart technocrat and professional.

If your goal is to create a significant personal fortune, cleverness and ingenuity usually form a big part of the equation. Understanding the strengths and weaknesses of the various individuals involved in any situation and—of critical importance—knowing how to operate in this environment are the ways to get seriously rich While there are always exceptions, street smarts and laser-focused motivation are pretty much essential to becoming seriously rich—and that’s even truer if you strive to join the ranks of the wealthiest entrepreneurs.

A smart way to use your street smarts

One way some self-made millionaires exercise their street smarts and “work the angles” is through low cunning. This is when the people with whom you do business make decisions that work beautifully for you even as they prove unproductive for them. Some examples:

  • During high-stakes negotiations, you use low cunning to get the other parties to see things your way and believe it’s in their—not your—best interests.
  • You get a competitor to believe that it will soon blow by you if it adopts a certain strategy— one that you know will send it over the cliff.

Self-made millionaires are often very capable at crafting scenarios so the businesspeople they’re dealing with ardently believe they’re getting the best of the deal—which turns out to be not at all the case. One top entrepreneur we know who is adept at low cunning explained it like this:

“It’s about getting inside your opponent’s head and feeding his or her fantasies, which when acted upon tend to benefit you.”

Being cunning entails being clever and crafty and, whenever possible, wrapping ingenuity in subtlety. Low cunning takes that up a few levels: You’re more guarded and wily, as well as much more imaginative. It’s all about gift-wrapping and presenting someone’s business fallacies and delusions—their heart’s desires—for your own benefit.

Note: When employing low cunning, you actually step back from the limelight and fade into the background—letting the fantasy, not you, take center stage. You avoid unfavorable repercussions—such as “getting credit” for sending your competition astray—so you can employ this approach again and again. Indeed, low cunning done well produces a virtuous cycle—usually with strong outcomes.

Ultimately, low cunning is all a matter of letting a foolish business decision gain traction and sometimes even facilitating that trend, hence depleting your opposition’s resources. Most important, it prevents your opponent from getting onto a more constructive track. In the end, low cunning is certainly not characteristic of all self-made millionaires—and most of those who use this approach do so very selectively. Indeed, it’s often more advantageous to take an approach where everyone involved in a situation walks away winning in some way—particularly if you expect to do more deals with a person or party down the road. But the fact is, the “high art” of low cunning characterizes some of the wealthiest self-made multimillionaires out there today.

Using high-caliber negotiation techniques

Another street-smart approach that self-made multimillionaires tend to be great at is negotiating. They consistently approach the process of hammering out a business deal in significantly different ways than people who don’t attain serious wealth. As a result, they radically increase their ability to get the terms and outcomes they want. These entrepreneurs’ bargaining brilliance can be summed up by the following negotiation formula:

Perspective + Purpose + Preparation + Process = Performance

1. Perspective is your negotiation mindset—being intensely focused on achieving your agenda.

2. Purpose is what you want from the negotiation—the results you expect and visualize.

3. Preparation is your prework going into the process. It’s how you evaluate the negotiation, the strategic approach you use, the formulation of your key arguments and how you see ways to gain the upper hand.

4. Process is the back-and-forth between you and the person across the table from you— how you leverage the relationship you create with someone who is, in some ways, your adversary.

Action steps

1. View the other party accurately—don’t assume. It’s easy to assume a person who is successful in one or two areas must be equally skillful in many other aspects of life—but that’s often not true. When sizing up and dealing with someone in business, acknowledge only the other person’s true qualities—not ones you think might be there. Example: If a person is very successful at running a manufacturing facility, you might immediately conclude he’s highly intelligent and financially savvy. Both of those assumptions could be inaccurate, however. The upshot: Don’t let the other party impress you more than is deserved. Look for proof of a person’s capabilities—and don’t attribute positive qualities to people beyond what they have actually demonstrated.

2. Learn all you can about the other party—and use that information at the negotiating table. Everyone has insecurities, personal quirks, interests and unique situations that can serve as strong bargaining tools for you. What’s more, there are multiple ways to gather that information—from actively listening to the person and showing empathy to simply “asking around” about a person. Example: One millionaire entrepreneur who wanted to buy out a competitor learned that person was filing for divorce soon. After talking to some people, he concluded that the seller probably needed a lot of cash, fast. During negotiations, the entrepreneur, while offering immediate cash, pushed hard for his terms—and got them.

3. Be aware of your own flaws and insecurities—and don’t let others exploit them. Be honest with yourself about your own challenges, weaknesses and dysfunctions. Self awareness of your vulnerabilities can essentially inoculate you against others’ efforts to use those vulnerabilities to their advantage.

4. Work with professionals who can help you hone your skills. When it comes to honing street-smart deal-making skills, practice makes perfect. Working with seasoned professionals who can help you navigate the world of negotiation and deal-making is a savvy move. Look for pros who will collaborate with you on deals and bring you into the process with them.


A strong ability to “read” other people and negotiate in savvy ways, using the resources available to you, can be a key driver of your success going forward. Adopting a mindset that values street smarts as well as intellectual insights can potentially make all the difference.

Securities offered through LPL Financial. Member FINRA / SIPC. Investment advisory services offered through NewEdge Advisors, LLC, a registered investment adviser. NewEdge Advisors, LLC and Congruent Wealth, LLC are separate entities from LPL Financial

VFO Inner Circle Special Report By John J. Bowen Jr. © Copyright 2023 by AES Nation, LLC. All rights reserved.

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