You might know Draymond Green, NBA superstar: Three-time NBA Champion. Three-time NBA All-Star. 2017 Defensive Player of the Year. Recently signed a four-year, $100 million contract extension with the Golden State Warriors.

But you probably don't know Draymond Green, entrepreneur: Early investor in SmileDirectClub, whose recent IPO values the online dentistry company at nearly $9 billion.

Co-owner of 20 Blink Fitness franchises opening soon in Michigan and Illinois. Investor in businesses like Performance Inspired, Mark Wahlberg's supplement line, Rumble, a boxing-based fitness startup, and UNINTERRUPTED, a multimedia platform for athletes founded by LeBron James.

Founding member of 100K Ventures, a Flint, Michigan-based accelerator group that invests in early-stage companies.

As you'll see from my conversation with Draymond, all of that serves as a great example of how the fundamentals of achieving success in one field -- drive, persistence, humility, lifelong learning, etc. -- definitely applies to achieving success in another. 

Your entry into business is different from most. You didn't have to work your way up the ladder to be able to get in front of successful people. That jump-started the process... but also means you dove straight into the deep end. 

It doesn't really matter where you start. It always comes down to building relationships with smart people... with good people you can trust. That's where it all started with me: First you build relationships, and then business may take off from there. 

I did get access to people that I may not if I wasn't in the position I'm in, but at the same time with that access comes the need to understand that whatever business opportunities those relationships can lead to... that doesn't mean you blindly think, "Because this person had success with that, I'm going to listen to them." 

You still have to take the time to learn for yourself, understand the business you might get involved with, and then go from there. 

Because it's still up to you -- it's always up to you -- to decide for yourself.

You have tremendous name recognition, so that can get you into a lot of rooms... but there are plenty of athletes (and celebrities) whose business ventures are more like vanity projects. How do you get past the assumption you might be more sizzle than steak?

One, what type of conversation can you have? What type of knowledge do you have about the person or the business? 

And if you don't have much knowledge -- which is okay, by the way -- are you going to sit there and pretend? Or be humble enough to ask questions, to make it known you don't have the knowledge... but you have the curiosity to go after the knowledge. 

I'm extremely curious. And I don't mind being the dumbest person in the world. I enjoy when I'm in a room and I'm the dumbest person.

That means you've put yourself in the right room.

That absolutely means you're in the right room. 

Very often I am the dumbest person in the room. I seek that. If I'm anywhere close to smartest person in the room... how much will I learn from being there?

Does your basketball success help you feel more confident in situations where you might feel less accomplished? Sometimes confidence from success in one area is at least partly transferrable... 

I think it unconsciously helps... but I never go in as "Draymond Green, basketball player." I go in showing I'm there to learn, to build relationships... that's all that is important.

The smartest people in the world know what they don't know -- and then figure out who can help them with the things they don't know.

People who are humble enough to admit what they don't know are the smartest people in the world, and that's the kind of person I strive to be. 

I will never be the smartest person in the world... but what I can do is get smarter every day.

Speaking of knowing what you don't know: Many of your investments are in fitness and health, which clearly you know a lot about. What drew you to SmileDirectClub?

A lot of my investments are in that area because those are spaces that I really understand.

When I was a kid I had braces from 8th grade to 12th grade. I wish SmileDirect had been around. It would have been a lot better for my mom, who was struggling to pay $7,000 for braces... making it more affordable -- while producing the same result -- would have been much easier on her and much better for our family.

When I first got to college I broke my retainers and my teeth shifted back, and that was that. So when I was thinking about getting my teeth fixed, what drew me to SmileDirect is that friends had started the business... and the product was something I was already in the market for.

Alex Fenkell, a close friend of mine, was in the early stages of starting SmileDirect. The first couple trials for me were a failure because they didn't have impression frames big enough for my mouth. (Laughs.) 

But I had so much success with it, and wound up being such a happy customer... so when the opportunity came to invest, it was a no brainer because I had been a happy customer. 

With hindsight, SmileDirectClub seems almost "can't miss" because it leverages several of major trends: Direct-to-consumer, beauty, growing public acceptance of healthcare delivery innovations...

Hindsight is 20/20, but at the time it was a no-brainer, too. One thing I've learned is that you don't follow ideas, no matter how great they might sound. It's all about execution.

And execution takes special people. The company was being run by David Katzman, who had already proven a couple times that he was one of best in the business at building direct-to-consumer companies, even before direct-to-consumer was really a "thing."

You followed that guy. Because that guy clearly has it figured out.

Credit to Alex and Jordan (Katzman) for coming up with a great idea. Those guys had to come up with the idea, they had to stick with it, come up with a business plan, make David feel it was something worth putting his time into... and then stick it out and work hard and make SmileDirect what it is today.

Ideas are kind of easy. It's a cliche, but execution really is everything. 

That's a big thing for me: You follow people. Not so much ideas. 

Great person with a decent idea, follow that person. A very smart, hardworking person with a decent idea? Follow that person.

Someone with a brilliant idea but who doesn't put in the work, doesn't execute... run as far away as you possibly can. (Laughs.)

Let's take that broader. What else do you look for in a pitch?

Lots of things. How much skin do you have in the game? You work a lot harder when you have something to lose.

What is the person's track record? You may not have much of a track record if you're just getting started, but still: You can get a feel for people pretty fast. 

Who else is backing this person? That says a lot to you. Again, I'm not the smartest person in the world, and there are really smart people who invest in companies... if they're not getting behind a company, am I the genius to say, "No, this works." (Laughs.) That's not a space where all of my time is dedicated on a daily basis. So understanding who else is supporting this person matters.

What's the competition like? What will make you different? How can I trust that you're the person to beat the competition?

With 100K Ventures, you're focusing on early-stage investments. Is it hard to not have a soft spot for people struggling to get an opportunity... and make an investment decision based more on emotion? 

No. And here's why: At that point, you're acting as a crutch. If their "stuff" isn't up to par, you're setting them up for failure.

Instead, tell them the truth: Their idea isn't up to par, their business plan isn't good enough... whatever the shortcomings are, be honest. Tell them the things you think they should know. 

They may not get the funding right then, but you may be setting them up for lifelong success by being honest: By showing them the level they need to reach in order to have an investor, in order to have a sustainable business or business plan that represents a sustainable business.

But don't be a crutch and lie to someone because you feel bad. Because you're only setting them up for failure.

That's something every athlete I've talked to says they valued most in a coach: Honesty. Don't tell me what you think I want to hear. Tell me what I need to hear. No matter how hard it might be to hear.

100 percent. That's how coach (Tom) Izzo (Michigan State head coach) was with me.

I'll never forget. I was on an unofficial (recruiting) visit and he asked me the things I was looking for in a school. Graduating, going to the pros, family atmosphere, playing time... I had a list of about eight things. He named seven of them off and said, "This many first-round picks, this many Final Fours..."

He went through them all, and then got to playing time. He said, "I can't guarantee you playing time. I don't know how hard you're going to work. I don't know who is going to outwork you. If I guaranteed you playing time, I'd be lying to you."

I respected that. That's one of the reasons I went to Michigan State. And sure enough he was never a guy to lie: Honest, truthful, and that is something -- and someone -- I truly appreciate.

How hard you're going to work is on you.

What was the first investment you made? 

Admiral Capital, David Robinson's venture firm.

Then SmileDirect, which was also the largest investment I had made.

I'm sure you were nervous about those investments. How long did it take you to grow more comfortable with making investment decisions... that you felt confident in what you are doing?

I still haven't turned that corner. (Laughs.) 

There's a lot I don't know. I'm not too proud to ask for advice. Or to change my mind if someone tells me I'm about to make a bad decision. 

I still lean on a lot of people. I'm not comfortable just saying, "Oh, yeah, I know what I'm doing."

And to be quite frank I don't think I ever want to reach that point in my life.

What drives you more? Hating to lose, or loving to win?

Hate. To. Lose.

Does that affect how you make investment decisions?

Here's the thing. In any investment you have to go in with the understanding that you might lose. I go into very investment assuming I'm going to lose.  If you're going to take the risk, you have to prepare yourself to lose.

When it comes to investing, risk is always a factor. So in that space, if you hate to lose... you're probably playing the wrong game. (Laughs.)

Project forward: Ten years from now, what are your goals? Where would you like to be? 

Ten years from now I'd like to be retired from the NBA, engaged in a number of business ventures.

And well on my way to my goal of becoming a billionaire.

Billionaire? That's your goal?

Absolutely. 

I've asked every athlete who has won a championship this question. First moments after winning your first NBA Championship: Did you feel happy... or relieved?

When I won my first championship it was relief. I felt like a weight lifted off my shoulders. For eight weeks, I felt like I had a clamp on my lungs and I couldn't breathe. Once they threw that ball up in the air... it was a dream come true.

But that pressure is like a gift, because it means you have the opportunity to do something special.

Published on: Sep 12, 2019
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