3 Contradictory Personal Qualities to Help You Build a Billion-Dollar Brand
Dec 27, 2022
Along my journey of entrepreneurship, I have reflected a great deal on the personal qualitiesthat underlie success. I believe there are certain qualities that you see in nearly every successful entrepreneur, and I have tried to distill them, understand them and reflect on them along my own path to building a successful travel technology company. I recently discussed these rules of success in a speech at Cornell, my alma mater, and now I'd like to share just a few of them with other entrepreneurs.
You'll quickly notice something about these rules: They are paradoxes. They seem contradictory at first glance. But that's life. Just like entrepreneurship, life is messy, complicated and often full of contradictory lessons. The trick is to accept that two seemingly opposite things can be true at the same time. Once you accept that, you allow yourself to adapt as circumstances require.
1. Don't be boring, but fit in
As entrepreneurs, we need to realize that starting a business does not make us special by itself. There are millions upon millions of entrepreneurs. Our task is to stand out from the crowd and make people remember our companies. For this reason, we can't be boring.
Take Elon Musk for example. Why doesn't he spend a dime on advertising at Tesla? Because he doesn't have to. He attracts all the attention he needs for his brand just by captivating imaginations … and headlines.
If you aren't Musk, the easiest way to create spectacle is at your company's events. Whether it's the launch of a product or an annual holiday party for investors and employees, you need to create a magical event that keeps people talking.
At my company, we try to do that around our charity events. On one occasion, I put Ann Coulter and Waka Flocka in the same nightclub — and it made the tabloids the next day.
Becoming a spectacle makes you stand out from the crowd. But at the same time, you don't want to be arrogant, flashy or ridiculous. People want to see someone who is relatable to them, even if on a slightly elevated level. Similarity breeds liking. And for this reason, you must be humble and easy to approach.
Think of all the great leaders you admire. While they are undoubtedly special people with extraordinary qualities, you also see parts of yourself in them — as do millions of others. In this way, they are like a mirror. If they were so eccentric that people couldn't relate to them, then people wouldn't want to be around them.
One way to make yourself more relatable is through self-deprecating humor. If you aren't afraid to make fun of yourself, it projects confidence and relatability — while still providing that all-important entertainment value that makes you stand out.
2. Don't be slow, but don't rush
One of the first qualities I see in successful people is that they are never slow or late. Most wake up before dawn. Some mornings, I am up at 1:00 a.m. to start my day. I try to be 10 minutes early to every meeting because it is the ultimate show of respect to others. Under all circumstances, never be late or lazy.
But also, don't hurry. Seeming like you're rushed or frantic makes you look amateurish and out of control. The most successful entrepreneurs make it look like life is easy for them. Even though I get to a meeting 10 minutes early, I look like I just showed up on a leisurely stroll.
Just as this rule applies in your daily life as a founder, it also applies in your macro entrepreneurial journey. Don't be late or lazy in starting your business. I respect those who start a business without waiting for the "perfect time" because, of course, there is no perfect time. If you wait too long, someone will beat you to it.
You never want to be late when founding a company, but you also never want to rush your way through. Countless founders make this mistake — they mistake all growth for good growth. But in reality, not all growth is the same.
Easy growth is hardly ever profitable. There have been a lot of rewards for "blitz growth" in the tech industry in recent years. Companies were often valued on a multiple of revenues, but that changed in the last year with a big market correction.
In the summer of 2021, valuation formulas changed from a multiple of revenues — 5 or 10 times depending on your growth rate — to an EBITDA projection. EBITDA is complicated, but here's what you need to know: To create positive EBITDA, you need slower and more organic growth. And that's harder to create. It requires avoiding shortcuts like taking on piles and piles of venture capital money to force your way into the market.
3. Be disagreeable, but don't disparage others
Successful entrepreneurs are tough. Whether it's Steve Jobs or Elon Musk or Henry Ford, they aren't afraid to make enemies and be the "bad cop" once in a while.
Too often, entrepreneurs fall into the trap of wanting to be liked. But when the going gets tough, and you're the founder, you're the person everyone turns to. Usually, that means not being the nice guy. You have to accept that you can't make everyone happy all the time.
You also need to know your worth and fight for it. People will attack you if your margins are too high, but if you feel that those margins are reflective of the value you bring, then stand by them. Don't be afraid to disagree with your detractors. They have their view, you have yours. Let the market decide who's right.
That said, you should never disparage others, including your competition. If you're confident in what you offer, then competition is a good thing. It sharpens your sword. It makes you better. In the early days, I did not follow this rule. I was aggressive about speaking poorly of our competition. I don't do it anymore because I've matured and feel much more comfortable and confident in where we are as a company, so I don't have to anymore. And it shows.
Similarly, you don't have to take on every conflict. You must pick and choose your battles. Sometimes the best approach is to move away from a problem or conflict and pretend it doesn't exist. This is what the ancient stoics teach.
Stoicism is one of the qualities you see in great leaders throughout history. It's the ability to ignore a problem because you know the problem will resolve itself, and by giving it your attention, you would make it bigger than it needs to be.
Your time is valuable. When you put your attention into something, it will cause that thing, whether it's a problem or an opportunity, to expand. So, it's better to put your attention into the positive rather than the negative.
These are just three of many rules I have learned in my own life and by studying other great entrepreneurs. Do the rules contradict themselves? A little, but that's reality. As an entrepreneur, you have to be able to pivot between competing truths. Never be too strict or rigid on anything. Allow your life and style to be a paradox. At the very least, this will make you less predictable to your competitors and opponents.