“”, With Douglas Brown and Dre Baldwin of ‘Work On Your Game’

This is a SALES business. When I first started looking for speaking gigs, a seasoned event planner who saw that i was new told me that this game was all about selling. He told me that the speakers are hustlers, and getting booked in the speaking business was a hustle in itself. His words were […]

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This is a SALES business. When I first started looking for speaking gigs, a seasoned event planner who saw that i was new told me that this game was all about selling. He told me that the speakers are hustlers, and getting booked in the speaking business was a hustle in itself. His words were very true. No matter how good you are at your thing, if you can’t sell yourself, no one will ever know.

As a part of my series called “Five Things I Wish Someone Told Me Before I Started My Consulting Business ”, I had the pleasure of interviewing Dre Baldwin.

In just 5 years, Dre Baldwin went from his high school team’s bench to a 9-year professional basketball career. At the same time, Dre built a content publishing empire.

Blogging since 2005 and publishing videos to YouTube starting in 2006, Dre has published over 7,000 videos with his content being viewed over 73 million times. Dre’s daily Work On Your Game Podcast has over 3 million listeners.

Dre has given 4 TED Talks and authored 27 books.

Link to Dre’s Free Book:

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

Thanks for having me!

I took a much different path to the consulting industry than most people have taken.

My background is as a professional athlete; I played basketball overseas for 9 years after walking on at an NCAA division 3 school, what is a level that most athletes do not make it pro from. That same year (2005), I started publishing content to this brand new website called “YouTube.” . This was not a normal thing to do at the time, as you probably know. After a few years of posting videos while still playing professional basketball overseas, the players who were watching me on YouTube started asking me questions about my approach — thing like why I kept coming to the gym every day to work out, how could how they can learn to have the same confidence in a game or in front of a crowd that they had in practice, or what it was that pushed me to keep trying to make it in basketball despite the fact that I had come from very humble basketball background (I got cut from my high school team 3 times!).

I started creating content answering these questions that players were asking me, and unbeknownst to me I was laying the foundation for a philosophy that I now teach on purpose. That philosophy is called work on your game. It’s four principles:

  1. Discipline: show up day after day and do the work
  2. Confidence: put yourself out there boldly and authentically
  3. Mental Toughness: continue to show up do you want to work putting yourself out there even when the success you expected to achieve has yet to be achieved
  4. Personal Initiative: be a go-getter — make things happen instead of waiting for things to happen.

These principles were the exact tools that I had used to become a professional basketball player, and to become an influencer on the internet long before being an influencer with a normal thing to be. When I started talking about these “Mental Game” tools, people who were not even athletes all of a sudden started finding my content. They started telling me that they followed me not because they were trying to learn how to dunk a basketball, but because The stuff I was talking about applied not only in sports, but also in business, at school, and in life. This is how I knew how I learned the value of this work on your game philosophy that I was created. It also planted a seed in my head for what I could do and who I could serve outside of the realm of Just Sports, and I had always seen myself as doing a lot more in life than just playing sports and just being in the Sports World. I’ve always been a business person at heart.

When I stopped playing professional basketball in 2015, I already knew what I was going to do: get into the world that we now know as thought leadership, and share this work on your game philosophy with business professionals, entrepreneurs, and of course athletes. That’s how I got into this line of work.

Can you share the most interesting story that happened to you since you began at your company?

The most interesting thing that happened was learning from a mentor of mine that my experience as a professional athlete could be directly translated to value for business professionals and entrepreneurs.

Learning that the mental toughness, discipline, and confidence necessary to succeed in sports could be valuable in the business world was huge for me, and is why I even started a consulting business: sports was my background and the thing that I had to offer. Business people love to hear stories from athletes, as we come from a different background that few ever experience, and a career in sports is a dream job: you play a game for a living! This is not to say there wasn’t work involved; I had to create a framework that made my athletic experience make sense for the business people I’d be serving.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I met my business mentor through being involved in Toastmasters, actually.

I’d joined Toastmasters based on a tip from a friend who told me that it was a good place to learn about the speaking business. The funny thing is that although this was not actually true, I stuck around at Toastmasters as I’d met people who are still friends of mine to this day.

The first time I spoke at Toastmasters, I shared that I had joined because I was looking to learn how to get into the professional speaking world. Someone in the room that day happened to have the same goal, and also happened to be a former athlete himself, coincidentally — albeit in football, not basketball. He told me that he was on his way to a professional speaking convention, and he would pass to me anyone any contacts he met who might be useful. The one person he met and told me about became a mentor of mine.

She taught me the ropes of the consulting industry as far as the speaking business, coaching, and selling myself in the thought leadership world.

The most important thing I tell people about that mentorship is that I acted upon everything that I was told. I wasn’t just passively taking in information and doing nothing with it — which is what many people do when they claim to be seeking help. It was the fact that I implemented what I learned that made mentorship worthwhile.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Work On Your Game”! — Dre Baldwin

That’s a phrase that I started using over a decade ago when I was making content mostly for basketball players. Players always asked me for help, advice, and tips on their basketball game. I noticed the players were always watching me on video, instead of being in the gym actually practicing — which is what I was doing, which is why they were watching me in the first place. So I use that phrase to let players know that they need to spend less time watching and thinking and talking about getting better, and spend more time actually doing the WORK to get better.

The great thing about the “Work On Your Game” phrase is that it is not limited to sports — it can be applied anywhere in life. The phrase itself is easily understood by everyone who sees or hears it without any explanation. As a speaker / thought leader / consultant, it has just as much relevance as it did with athletes.

Ok super. Thank you for all that. Let’s now shift to the main focus of our interview. We’d love to learn a bit about your company. What is the pain point that your company is helping to address?

As a company, work on your game Incorporated. Helps people do three things:

  1. Work On Your Game
  2. Show Your Game
  3. Get Paid For Your Game

This is the process that anyone must follow, whether athlete, entrepreneur, teacher, student, or business professional, in order to create value, share that value with the world, and receive the return on investment for the value they have created.

We help people who have nay of the following pain points —

  1. Need more “Game”
  2. Need to better display their “Game” when it matters
  3. Need more people to know about and appreciate their “Game”

What do you think makes your company stand out? Can you share a story?

What makes our company stand out is the fact that I come from a background that is different from most consultants, having played professional sports. Also the fact that my professional sports career was not a yellow brick road; I played at a division 3 college that had never produced a professional player before I became the first to make it. The fact that I succeeded against tall odds to even make my sports career happen allows many people to relate to me when they feel they are coming from an underdog background, even outside of sports.

The second thing is that I built my business on the back of the internet and social media, long before it became a common thing to do. I was publishing content online back in 2005, way before it was cool, and before there were paved roads to making money through publishing content. I first got known on the internet just for giving value to people, not trying to chase a dollar. So when the opportunity came to make money from content, I was already established. I saw opportunities in it even before they existed.

Another thing is that I am always real, raw, and honest with people, telling them what they need to hear and not what they want to hear. When I speak to my clients, it is the number one attribute they most appreciate about me and the number one thing that separates me from others in the space.

When you first started the business, what drove you, what was your primary motivation?

Coming from a sports background, many athletes have no idea who they will be or what value they can offer the world outside of playing sports. Even those who do, go into traditional routes of TV analysis, coaching, or training. I always wanted to go into entrepreneurship, and the great timing of my career was that the internet came along at the time that it did, offering platforms that gave me space to hone my skills.

My main motivation was to take the value that I was already giving to athletes in terms of mindset, and translate that value to something useful for entrepreneurs and business professionals, which is what we do now. My overall motivation was always to find ways to improve myself through helping improve others, and never become a “has been” who had done great things in the past, but wasn’t doing anything useful today.

That is still my drive now: continuous improvement.

What drives you now? Is it the same? Did it change? Can you explain what you mean?

Yes! it is still the same as it was back then.

Growing up as a kid, I would see adults who seemed to have hit a plateau in life: they had advanced to a certain level, but didn’t seem to be getting any better from that point forward. I abhorred the idea of becoming that myself.

One thing I tell my audience all the time is that after puberty, any growth must be voluntary. You must want to grow, and you must take intentional action to do so. I have always been personally focused on growth, advancement, and getting better with time. Unfortunately, not everyone is interested in that, as evidenced by the many people we can see who seem to have gotten to a certain point and stop advancing in life.

My goal is to help the people who want to advance, and give them the tools they need to do so — starting with the way we think.

Are you working on any exciting new projects now? How do you think that will help people?


I am working on two new books that I will release in a bundle later this year. They will help people because they will build on the philosophies and foundation I have already established through the material I’ve created for the past 16 years.

All the while, we focus on making sure we get the workout about our materials to the people who need it, since it can’t help them if they don’t know about it.

Does your company have a sales team? If yes, do you have any advice about how companies can create very high performing sales teams?

I am the main architect of how we do sales, and we create processes to make sure we get our materials into the hands of the people who need it.

How a company can create a high-performing sales team:

  1. Give them good things that they will be proud to sell.
  2. Keep everyone sharp and on-point mentally.
  3. Create a process, test it and tweak it to make sure it works. Then make sure you follow it.

In your specific industry what methods have you found to be most effective in order to find and attract the right customers? Can you share any stories or examples?

One thing is to get yourself in front of audiences that are already filled with the right customers. For example, we are doing this interview right now because I know your publication has an audience of people that I want to be in front of.

Another thing anyone can do is to make sure that your marketing materials — which is anything and everything you share — is targeted towards the type of people that you would ideally want to be working with.

Based on your experience, can you share a few strategies to give your customers the best possible user experience and customer service?

  1. Treat your customers as your boss, because they are. Without them, you have no business. Everyone in your company should know this both logically and emotionally.
  2. Aim to give people a remarkable experience — something they will want to tell a friend about. \
  3. Make sure you are delivering results! That’s what customers pay for, and if you deliver, they will keep coming back.

Thank you for all that. Here is the main question of our interview. What are your “Five Things I Wish Someone Told Me Before I Started My Consulting Business”. Please share a story or an example for each.

  1. This is a SALES business. When I first started looking for speaking gigs, a seasoned event planner who saw that i was new told me that this game was all about selling. He told me that the speakers are hustlers, and getting booked in the speaking business was a hustle in itself. His words were very true. No matter how good you are at your thing, if you can’t sell yourself, no one will ever know.
  2. The value you offer doesn’t matter if nobody knows who you are. My best experiences have come when I’ve appeared on stages that are hard for others to get on, as far as keynote speaking gigs and media appearances. They all happened because I was willing to sell myself and garner attention. Drawing attention to yourself and your work is uncomfortable for some people. Many people feel as if their work should speak for itself, and (unconsciously) feel that the world should come to them just because of how good they are. This couldn’t be further from the truth. If you believe in the value of what you’re offering, have no shame in promoting it and you! The world needs to know about it, and it’s your job to let them know.
  3. Relationships and connections matter more than skill. Though I have skill, the only reasons I’ve been able to turn that skill into money is because I’ve aligned myself and made connections with the right people and got in front of the right audiences. It’s only after I’m in front of the right people that my skills matter — because now I have people’s attention. The last thing you wanna be is a secret whose value remains undiscovered. I met my mentor because of a loose connection to a guy who I didn’t really know. I’ve landed keynote speaking contracts because I was willing to speak for free at first and proved myself, creating a relationship.
  4. Your unique style matters more than being “better” than others. How do you quantify “better”? You can’t. I see people who I think I’m better than all the time. But we as consumers don’t make choices based on who’s better — we choose what we like. Often what we like is the unique blend someone brings to the table. No one has ever hired me because I was “the best” option — it’s always because of the blend of skills and uniqueness I bring.
  5. Find a topic / aspect that you can OWN. “Work On Your Game” is a brand and topic that I own. Google it and you can see. I started it in 2009 and it has taken off ever since. When you look around at other well-known consultants, they all own a brand in the same way: A specific topic or angle that their name is forever associated with.

Wonderful. We are nearly done. Here are the final “meaty” questions of our discussion. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

We already have that movement going!

Work On Your Game. Even if I didn’t explain what it means, you know what it means to you. It speaks for itself. It’s the very essence of my life and my career in sports, online and in the professional world. If everyone followed it, we’d all be building condominiums on the moon right now.

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

Sean Combs. I’d talk to him about his branding and marketing mindset and how he got the whole world to follow his lead in the entertainment industry. Even though we work in distinct fields, I think some of what he did in entertainment could translate to consulting. Even if we never meet, I will eventually figure it out and use it.

Thank you so much for this. This was very inspirational, and we wish you only continued success!

Thanks for having me!

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