Three Questions from Ray Dalio that Will Help Determine Your Entrepreneurial Success

Jordan Gross

2. To what extent are you radically truthful and transparent?

One major thing separated Ray Dalio from the rest of the keynote speakers I heard at a recent event. Instead of focusing on providing us with the best answers, the billionaire investor focused on asking us the best possible questions. He shared the questions he asks himself and other entrepreneurs when pursuing any exciting endeavor, which of course includes building your business.

On this particular day, a day in which I listened to online seminars from the founder of Charity Water, the leader of Hint, and various other founders of successful startups and non-profits, the greatest differentiator was Ray’s ability to ask unique questions. These were questions that many are too afraid to ask. These were questions that really made you dig deep into where you were and where you wanted to be. These were questions Ray used to assess whether or not an entrepreneur would have what it takes to achieve Ray Dalio level success. Ask yourself these questions as you build and grow your business.

1. How do you deal with not knowing?

Ray Dalio believes that more than half of the entrepreneurial battle is how you respond to uncertainty. During his talk, he mentioned how especially in his world of financial markets with such high levels of volatility, being comfortable with the unknown separates the winners from the losers. Those who are confident with not knowing are able to carefully and methodically respond to certain situations, while those who are uncomfortable impulsively react to extraneous events according to Ray.

Ray gave a simple but specific example about a time in which his company was on the verge of bankruptcy. If they did not close this one particular deal they were negotiating, Ray believes they would have had to close up shop. He attributed the ability to push through this situation to his principle of simply being okay with his life no matter what happened next. He did not attach too much significance to whether they won the business or not. Because of this, he was able to more calmly approach the situation and get the deal completed.

How do you handle your not knowing? Do you worry about the future and make panic decisions? Or, are you okay with whatever happens? Do you stay optimistic? Or do you drown in negativity? Think about some times in your life when you didn’t know the answers or what was going to happen, and assess your responses.

2. To what extent are you radically truthful and transparent?

Ray thinks that part of his company’s success was because everybody knew everything that was going on. From the maintenance team to the CFO, every employee was involved, valued, and informed about whatever was happening at the company. For instance, during the same bankruptcy example as before, Ray had a choice. He could either not tell his team they were on the verge of bankruptcy and hope he’d never have to, or he could let them know what the situation could be so they could plan accordingly. Because he told them the full truth, he believes he developed a sense of trust that trickled into every interaction and deal they made.

To further support his point, he presented a counterexample. Elizabeth Holmes of the infamous Theranos decided to lean on the other side of transparency. She created a company culture that was rooted in secrets. Nobody really knew what was going on, which led to lying, cheating, a lack of trust between employees, and eventually, complete and utter chaos. Elizabeth Holmes lost her company because she lost control of her people. She lost control of her people because she didn’t create a system in which they could believe anything that was going on.

To what extent are you radically truthful and transparent? Do you always tell the 100% truth? Or do you tell white lies to help the situation seem more favorable? Do you create an environment where people know, like, and trust one another? Or is there a lingering sense of tension because only some people know what’s going on? If you want to be like Ray Dalio and live according to his principles, make sure that transparency and truthfulness are at the forefront of your company values.

3. Do you intend to worry about appearing good or doing good?

Too much focus on perception can be a company killer according to Ray. When an entrepreneur is in it to achieve some sort of external validation or to appear like a hero or a savior to the outside world, then they are doomed for failure. In actuality, it is those entrepreneurs who just do good for good’s sake that actually change the world.

People who worry about appearing good end up chasing instant gratification. They chase the next high, the media interview, the award ceremony. But people who focus on doing good have a more long-term goal in mind. They do anything it takes to show up for their team and ensure their companies success in accordance with their mission.

In Sam Walker’s book, The Captain Class, he calls these individuals the water cooler carriers. Are you somebody who will carry the entire jug of water to practice for your team just because you know the team will go thirsty otherwise? Or are you a showboat? Are you somebody who has to show off their flashy ideas, wins, or money in order to feel a sense of pride?

Final Question

Just like with all advice, the most important question you have to answer after reading this article is what are you going to do now? Take some time to reflect upon these questions. Think about situations in which there was something unknown. Judge whether or not you are truly transparent. Think about if you actually want to do good or if you just want to appear good.

Entrepreneur or not, you must ask yourself questions like this in order to understand the type of person you are at your core. The more honest and reflective you can be, the sooner you can make changes to end up being the person you’ve always wished to become. Asking yourself the right questions is how you ultimately separate yourself, just like Ray Dalio.

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