One of my favorite things about being the host of  The School of Greatness is that I get to learn from the best minds in the world about stuff I am fascinated by.

Yes, it's as awesome as it sounds.

There are few things I geek out about as much as smart ways to make money and build successful businesses.

So when I got the chance to sit down with

If you don't know him already,

He started his first business when he was 6 years old, selling pencils at his school, and hasn't let up since.

Overcoming any and all odds most entrepreneurs face,

He was recently appointed to a national entrepreneurial position which took him to the White House, and he is a current entrepreneurial advisor on the hit show Shark Tank.

He also just came out with a new book, The Power of Broke, in which he tells the truth about the importance of earning your way to the top.

That's right, hustle is the way to the top (my favorite).

Daymond and I talked about all parts of entrepreneurship, the ins and outs of building a successful startup, and the lessons he's learned on his own journey.

I especially wanted to know what the biggest challenge was once his business took off. Since he didn't have a formal business background, he said scalability, financing, customer support, shipping, and all the other business operations were all a big challenge. The way he overcame those leaks in his business was by building strategic relationships with people who were strong in these areas. "I had to plug the dam," he explained.

While he was building those relationships, however, he was still broke and trying to get his T-shirts in the public eye.

Here's what he learned in getting his shirts into over 30 rap music videos without paying for the opportunity:

"The Power of Broke"

When you have to do everything yourself, you learn every process because you can't afford to hire anyone. This is invaluable later, when you are successful and do have people to delegate to. No one can tell you lies about how they're doing their job. You know exactly what their job requires, so you can tell if they're not doing a good job.

Being short on cash and opportunities means you focus on the only thing you can do. Oftentimes that means you just focus on selling, which creates cash flow. You don't drown in opportunities because you can focus on one at a time.

You learn the character of the people around you. When you don't have much to offer people, you learn who you can count on, who you can trust, and who you want to share your big opportunities with later.

As a result of these lessons, he explained, he has been able to successfully create and grow multiple businesses in several industries over decades.

Since he is such a fan of the power of broke, I asked him how he taps into it currently, since he's no longer struggling financially. He gave me a powerful example of how he is marketing his new book.

Instead of letting publicists and professional marketers do the work, he has been hustling daily to create opportunities (like my podcast) to market the book himself. He reaches out personally to contacts, acknowledges them, and sees how he can support them.

Daymond also gave an example from his current business. Instead of paying the average $75K - $150K to get a new clothing line off the ground, when he has an idea for a new design, he pays $1500 to a seamstress to get some samples made, pays $1000 - $2000 to an Instagram influencer to wear and post about it, and then waits to see the feedback. If orders start coming in, he moves ahead with another piece from that line. If not, he scraps it and moves on.

As Daymond put it, "You're going to fail more than you're going to succeed." So make your failures cheap and channel all your money into what is succeeding.

To hear our whole conversation, listen to this episode at