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Dre Baldwin of ‘Work On Your Game’: “Have a growth strategy”

Have a growth strategy. Know what the next step is for your business to grow and advance. When you have multiple things to be done, a solid strategy prioritizes everything that is to be done. I worked for years in my business with no strategy whatsoever — it was only when figuring things out as I went […]

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Have a growth strategy. Know what the next step is for your business to grow and advance. When you have multiple things to be done, a solid strategy prioritizes everything that is to be done. I worked for years in my business with no strategy whatsoever — it was only when figuring things out as I went along stopped working that I noticed and paid attention to my lack of strategy.


As part of my series about the “How To Take Your Company From Good To Great”, 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 TEDxTalks and authored 27 books.

Link to Dre’s Free Book (just cover shipping): http://MirrorOfMotivation.com


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Thanks for having me! I’m excited to be here.

I was always into sports as a kid, and played all the normal inner-city kid sports — kickball, touch football, backyard basketball. Football was the first team sport I tried, then baseball and finally basketball at age 14.

Outside of sports, I was immediately drawn to computers and the internet the first time I saw it. My family got our first computer when I was 12, and I’ve been glued to computers ever since. When I saw the internet, I knew it was for me.

I started my business around 2008–10, creating and selling training programs to athletes while still playing basketball overseas. Many athletes were asking me about my mental approach to the game, and my answers to those questions became the foundation of the Work On Your Game philosophy and brand. I stopped playing pro in 2015, and my business now is all about taking the “mental game” tools that we utilize in sports and translating those tools to the professional and business world.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

There was never a time I considered giving up, because one thing I was clear about was what I did not want!

Growing up, the adults around me all worked regular jobs, and none of them ever seemed too excited or happy about those jobs. On top of that, none of them ever had much free time or money. So, being that these were the only adults I knew and could see, this was my view of what regular job life was like — and I knew that’s what I did not want. So, my mind was always set on entrepreneurship. Reading Rich Dad, Poor Dad by Robert Kiyosaki in college was my introduction to the concept of entrepreneurship, and I knew it was for me.

While there were and are challenging times for anyone building and running a company, I never considered the alternative of not running a company. If anything, I might shut down one business to start another, but I will always be an entrepreneur.

As far as my drive, I would have to credit my background in sports, where I had to push myself and hustle my way into even making it as an amateur player, let alone a professional player. I took that same internal drive with me to the business world.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

The funniest mistake I made was the fact that I was good enough to create products, sell them and make money without ever strategizing about or considering an actual plan for my business!

The reason this was a mistake was because the more success I created without a plan, the less I felt like I needed a plan — until it got to the point where I couldn’t go any further without a plan. That’s when I realized that I could not just rely on my talent, and would need to have some actual structure to my business if I wanted to be a real CEO and have a real, stable company that would stand the test of time.

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

What makes our company stand out is the fact that we help people develop their game from the inside out.

And that “game” is anything that the person is involved in: sports, business, professional development, advancing to a new position, growing in your current position, student, or a person who is looking for their place in life.

Our philosophy applies to anyone who is looking to either get better, get better at showing their abilities, or get better at drawing attention to their abilities.

Those are the same things that I needed to do as an athlete and as an entrepreneur, and now we help people solve the same problems that I needed to solve myself.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Number one would be to stop trying to do everything by yourself.

When we first get started, we all have to do everything on our own; the challenge is that many of us get to a certain point where we could offload some work, yet we keep doing everything by ourselves.

Outsourcing work and delegating tasks can be hard, and actually takes more time and effort at the beginning then it would take to just do everything on your own — which is the reason why many people continue doing everything by themselves forever. This is probably the number one thing that burns out entrepreneurs.

Another tip: create a strategy for yourself and for your business.

While your strategy or plan will probably be faulty and far from accurate at first, the time and attention that you give to even making a plan is well worth the investment. Many business people, myself included, just head into business doing random things, and hope that something works. The gift and the curse of that is that if you are talented enough, and the market and timing are on your side, you will actually create success — it’s only when that luck and talent has taken you as far as it can that you realize your mistake.

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?

I would have to credit the many virtual mentors I have had over the years, mostly through books and videos that I have consumed.

I understood the power of having a team and utilizing the knowledge and strength of other people, and not doing everything by myself, even when I was still doing everything by myself. I knew I would eventually need to build a team and have always been open to offloading work from me to others so I could focus on what I do best, my zone of genius.

As for specific people, I would cite Napoleon Hill, Jack Canfield, Jim Rohn, Tony Robbins, Sean Combs, Shawn Carter, and Curtis Jackson.

Ok thank you for all that. Now let’s shift to the main focus of this interview. The title of this series is “How to take your company from good to great”. Let’s start with defining our terms. How would you define a “good” company, what does that look like? How would you define a “great” company, what does that look like?

Great question.

I would say a good company is one that is earning enough revenue to stay afloat, serve its clients, and pay its staff. At the same time, a good company is not necessarily growing from its current position.

A great company is one that is doing all of the above, save for one difference: it is growing, advancing, and taking on more and bigger problems to help even more people. In the process, the people within that company are enjoying even more and better rewards as a result of the more people they are able to serve and help.

Based on your experience and success, what are the five most important things one should know in order to lead a company from Good to Great? Please share a story or an example for each.

  1. Solve bigger problems. When Apple solved the problem (that no one knew they had) of the non-existent smartphone, Apple took off — and to this day, they make the majority of their revenue from the iPhone.
  2. Know your audience. There are new apps and products coming to market every day. When you don’t know what your audience is and how they think, every new shiny object will look like an opportunity.
  3. Have a growth strategy. Know what the next step is for your business to grow and advance. When you have multiple things to be done, a solid strategy prioritizes everything that is to be done. I worked for years in my business with no strategy whatsoever — it was only when figuring things out as I went along stopped working that I noticed and paid attention to my lack of strategy.
  4. Do what you do best. On a sports team, every player has a role. From the star players to the coaches to the players on the bench who don’t get into the games, every role matters, and when anyone doesn’t do their job, the entire team suffers. As an entrepreneur, I know what I do best: Speaking, writing and recording. I aim to eventually offload any work that isn’t one of these three things.
  5. Adjust as necessary. I’ve started and killed off many products over the years when they simply were not working or landing the right way with my audience. While it does take courage to start something as an entrepreneur, it takes even more courage to end things that are not working! If you try enough things, some of them won’t hit the right way — don’t compound the situation by trying to force it where it’s simply not working.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. Can you help articulate for our readers a few reasons why a business should consider becoming a purpose driven business, or consider having a social impact angle?

A business without a purpose will not survive or go far!

Purpose is defined as “the reason for which something is done or created or for which something exists.” And no rational human being does something for nothing, at least not for long, and not very well. So of course every business should have a purpose, and every person working in that business, even if they’re not the owner, should have some purpose behind why they’re showing up to work everyday. Because if they don’t, eventually they will stop showing up, or they won’t be showing up all the way, not bringing their full selves to work.

As far as social impact goes, there are many ways that phrase can be defined. But if your business is successfully serving your clients and helping them get what they want, that in itself is a social impact. Social impact does not have to be giving to charity, or being involved in politics, religion, or anything along those lines. If you are helping people get what they want, and they are happy with the exchange they’re making with your company, that in itself is social impact.

What would you advise to a business leader who initially went through years of successive growth, but has now reached a standstill. From your experience do you have any general advice about how to boost growth and “restart their engines”?

  1. Reconnect with your purpose. Why did you get into business in the first place? What is it that you want to bring to the world? Are you still connected to this purpose? These questions will probably take you back to when you first started, or the spark that first led to the idea that led to your business. What I’ve found is that many entrepreneurs get too far away from this purpose the further they go in business, distracted by their everyday needs. It’s a good idea to remind ourselves from time to time why we even began.
  2. Reconnect with your audience. Who is the person that you ideally want to help? And why? Where are they now, as opposed to where they were when you first started — is it the same place? Maybe not! Make sure you are staying in touch with, and are accessible to, your core audience. If you allow your ideal audience to drift apart, you may not actually notice this until it is too late.
  3. Get active. Both of the above require you to get active — both mentally and physically. Do not just sit around feeling sorry for yourself, or mad at yourself for not being as motivated or inspired as you used to be. Your company is at a standstill because you are at a standstill. Get moving and get active, and your business will follow.

Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

When the economy is difficult for a business owner, the economy may also be difficult for its clients.

What that means: you should find out what challenges your audience is having, and see what you can do to help face down those challenges.

While there is never a guarantee that you will be able to continue growing during a difficult economy, you can always keep your eyes and ears open for new opportunities to better serve your audience. I think that is the best that you can ask of yourself as a business since we cannot always predict what will happen with the rest of the world, and none of us ever stays on a continuous winning streak; life happens.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

Yes — having a plan for where you’re going, what you’re doing, and what needs to be done next.

In starting my company, one of my biggest challenges was that I had a lot of ideas, a lot of energy, and only two hands, two eyes, and one brain. I couldn’t do it all at once! One of my biggest challenges was deciding what to do first, what to do next, and what the priorities were. Figuring that out has helped settle things down in my business a lot. And I know for a fact that many companies still have not addressed this challenge.

As you know, “conversion” means to convert a visit into a sale. In your experience what are the best strategies a business should use to increase conversion rates?

You can pay attention to what is working, doing more of that, and less of the things that are not working. That, in a nutshell, is what increases conversions.

Another thing any business can do is nail down who exactly your ideal customer is. Your marketing efforts will draw in more of those ideal clients, thus you have a higher probability of converting those people: you are offering exactly what those ideal clients want. If your marketing is bringing in a bunch of people who you don’t really want to serve, then it makes sense that you are not converting at the rate that you would want to convert at.

Lastly, look at your offering: is this what your ideal customer wants? This is a question that is easy to answer, because you can ask the customer themselves whether you are giving them what they actually want — and if not, they can help you design what they do want. When you give people what they want, they will give you what you want. Business is simple in that way.

Of course, the main way to increase conversion rates is to create a trusted and beloved brand. Can you share a few ways that a business can earn a reputation as a trusted and beloved brand?

Similar to what was said above, make sure you are targeting your ideal client, so that what you are offering and what they want are in perfect alignment. This takes time to nail down, but it is worth the investment.

Another thing you can do is be honest and authentic about who exactly you are as a company, so that your clients know exactly who and what they are dealing with, and can decide for themselves whether they want to be involved with you or not.

Not every client is even worth the dollars that they bring to your business, if they are not the ideal client with whom you want to work, and if you are not the ideal company with whom they want to be involved. Finding the right match is worth it.

Great customer service and great customer experience are essential to build a beloved brand and essential to be successful in general. In your experience what are a few of the most important things a business leader should know in order to create a Wow! Customer Experience?

Have a staff of people who actually care about the job and care about the clients they serve in the company they represent, and are not there only for the paycheck!

All of us have gone into businesses where we dealt with employees who were there just to get paid. They didn’t really care about the job, the company, nor did they care about the clients that the company was serving. This is a failure of the company and management, since they hired mercenaries who weren’t True Believers. Employers who get lazy in hiring end up with these subpar individuals representing them, who are not perfect matches for their company nor for the company’s clients.

That laziness ends up hurting the business in the long run, because the company indirectly turns away many of their ideal clients through interactions with these mediocre staff members.

What are your thoughts about how a company should be engaged on Social Media? For example, the advisory firm EisnerAmper conducted 6 yearly surveys of United States corporate boards, and directors reported that one of their most pressing concerns was reputational risk as a result of social media. Do you share this concern? We’d love to hear your thoughts about this.

Everyone, especially our ideal clients, is on social media these days. And when they have a question, concern, or comments, they will probably look to social media first to see if you’re present, before they use any other means of connecting with you.

It’s easiest, and it’s where people already are.

Therefore, every company should have a presence on social media, and be responsive to clients and or prospects on social media.

The only way a company can hurt its reputation on social media is by being on social media, yet not unresponsive, or something that the company does that happens to make its way to social media. But social media itself doesn’t hurt any company without the company’s participation.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

  1. Not knowing who you wish to serve. Some people start businesses by creating a product or service offer, but they don’t really know who it’s for, or exactly what it will do for those people. These offers don’t really land with anyone, even though the offer or product may be great in itself. Know who exactly you are making your materials for.
  2. Having a weak idea (or no idea at all) about the wants and needs of your ideal clients. To further the first point, here I refer to CEOs and Founders who don’t fully understand the mentality of the people they want to serve — they are more focused on what they want to give their clients, rather than asking their clients what the client actually wants. This seems like a tall task, but is not really as hard as it sounds. Have conversations with your ideal clients and ask them what their biggest challenges, needs, and frustrations are — one thing you will learn very quickly is that people are very willing to talk about their challenges in life, simply because very few people are willing to listen! You can fill that need by then the person who is going to listen, and you will know exactly what is going on in the minds of your ideal clients. This will put you ahead of 98% of your competition.

Thank you for all of that. We are nearly done. You are a person of great influence. If you could start 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. 🙂

The Work On Your Game movement, which is all about helping people develop their game, show their game to the world, and get paid for their game. Which is exactly what we all do in business.

How can our readers further follow you online?

Here are my social media:

http://LinkedIn.com/in/DreAllDay

http://Facebook.com/WorkOnYourGame

http://Twitter.com/DreAllDay

http://Instagram.com/DreBaldwin

http://YouTube.com/Dreupt

This was very inspiring. Thank you so much for the time you spent with this!

I appreciate the opportunity!

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