Dre Baldwin: “Solve Bigger Problems”

by Jerome Knyszewski
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Dre Baldwin Work on Your Game

Dre Baldwin is a former pro basketball player turned into hit podcast host. He hosts the popular daily Work on Your Game Podcast, which has more than 3 million listeners.

His journey to the professional leagues started in high school when Dre Baldwin rode his team’s bench. In just 5 years, he rose from the bench and played pro ball for 9 years. At the same time, he “built a content publishing empire.”

Since 2005, Dre Baldwin has been blogging. He has also been uploading videos to YouTube since 2006.

Since then, Dre Baldwin has uploaded more than 7,000 videos. Those videos have also been watched more than 73 million times.

Dre Baldwin has also given 4 TEDxtalks. He has also written 27 books.

As a child, Dre Baldwin has always been a sports fan. He played a lot of sports: “kickball, touch football, backyard basketball.” Then he moved on to football, his first team sport. At 14, he started basketball.

At the same time, Dre Baldwin was also “immediately drawn to computers and the internet the first time I saw it.” His family got their first computer when he was 12, and he has been “glued to computers ever since.”

Around 2008-2010, Dre Baldwin launched his business, “creating and selling training programs to athletes.” He was still playing pro ball in overseas leagues at this time.

Check out more interviews with successful content creators here. You can also grab Dre Baldwin’s book here.

I started my business around 2008–10, creating and selling training programs to athletes while still playing basketball overseas.

Jerome Knyszewski: 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?

Dre Baldwin: 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.

Jerome Knyszewski: 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?

Dre Baldwin: 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.

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

Jerome Knyszewski: 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?

Dre Baldwin: 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.

Jerome Knyszewski: 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.

Dre Baldwin:

  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.

Jerome Knyszewski: 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?

Dre Baldwin: 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.

Jerome Knyszewski: 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?

Dre Baldwin: 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.

You can pay attention to what is working, doing more of that, and less of the things that are not working.

Jerome Knyszewski: 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?

Dre Baldwin: 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.

Jerome Knyszewski: How can our readers further follow you online?

Dre Baldwin: Here are my social media:






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

Dre Baldwin: I appreciate the opportunity!


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