Professional athlete turned successful solopreneur: here's how.
Another solopreneur success story and profile on a former pro basketball player and how he used content to grow his business.
Another week, another profile on a successful solopreneur.
This one is especially exciting for me because 1) as you’re about to read, content creation was a huge part of his strategy (and I’m super bullish on content creation), and 2) this is a really great guy who actually guested on my old Solopreneur Grind podcast years ago when I was still doing it.
Might even dust off the podcast and start recording interviews again too…
Anyway, here are some amazing business tips and a link to our podcast at the end too:
Who are you and what is your business?
Dre Baldwin, owner of Work On Your Game Inc.
How did you get into the business originally?
It all began when I started uploading basketball videos to YouTube back in 2005.
As players watched my content, they started reaching out with questions about my mindset. They were curious about the thought process behind someone who kept pushing forward despite having an underwhelming athletic background.
I began sharing ideas about discipline, mental toughness, confidence, and personal initiative. Interestingly, non-athletes started finding those videos and reaching out to me as well. They explained that, even though my message was geared toward athletes, it resonated with them just the same.
That made me realize that there was a much larger audience I could serve with my philosophy, far beyond just athletes.
So, when I retired from professional sports in 2015, I already had a following of people who were interested in my insights on mindset, many of whom weren’t athletes themselves.
The big advantage for me was that I had been building an online presence while still playing sports. I started sharing content in 2005 but continued my athletic career until 2015, giving me 10 years of momentum by the time I transitioned into entrepreneurship. Because of that, my shift from sports to business was much smoother than it typically is for most athletes.
How big is the business right now and do you see a lot of room for growth in the industry?
We’ve built a solid foundation with Work On Your Game Inc., with 2 team members other than myself and we’re consistently delivering value through our coaching programs, courses, books, and content.
The growth potential is huge because what we offer — a focus on high performance, mindset, strategy, systems, and accountability — applies across industries and professions. The need for people to perform at their best, consistently, is universal, and we’ve just scratched the surface in terms of reach.
There’s always room for growth, especially as more people recognize the importance of not just working hard but having the right mindset and strategies to reach that top 2% of performers in any field.
We’re constantly expanding into new spaces, and the goal is to scale this to a level where the Work On Your Game philosophy becomes a cornerstone for anyone serious about achieving high-level success. There's a lot more ground to cover, and we're just getting started.
What are 5 key steps someone could take right now to build a similar business?
Here are five key steps someone could take right now to build a similar business to Work On Your Game:
1. Find Your Core Message: Get clear on the core philosophy or expertise you want to share with the world. For me, it’s about mindset, discipline, confidence, and high performance. Figure out what you can offer that’s both authentic to you and valuable to your target audience.
2. Start Creating Consistently: Begin publishing content that reflects your message. Whether it’s videos, podcasts, articles, or social media posts, you need to consistently put yourself out there. I started with YouTube videos in 2005, and that built momentum over time. Focus on creating value that resonates with your audience.
3. Engage with Your Audience: Pay attention to the questions, comments, and feedback you get from your audience. That’s how I discovered people were interested in mindset, not just basketball. You’ll start to learn what your audience wants and how you can serve them better.
4. Offer High-Value Solutions: Build products and services that solve specific problems for your audience. This could be coaching programs, courses, books, or memberships. Focus on quality and make sure the solutions you offer are aligned with your audience's needs and goals.
5. Leverage Systems and Scale: To grow beyond a one-person operation, you need systems that allow you to scale your efforts. This includes automating processes, building a team, and creating replicable strategies that help you reach more people while maintaining quality.
These steps help you build a foundation, gain traction, and eventually position to scale your business.
What's 1 key piece of advice you'd give to other solopreneurs out there?
One key piece of advice I’d give to solopreneurs is to systematize everything as early as possible. When you’re running a business by yourself, it’s easy to get caught up in the day-to-day grind and end up doing everything manually. But if you can build systems for how things get done—whether it’s content creation, lead generation, customer service, or even following up on emails—you’ll free up your time and energy to focus on growth.
Systems allow you to scale your efforts, delegate effectively when the time comes, and ultimately create a business that runs smoothly even when you’re not involved in every detail. It’s the difference between just working hard and building something that can grow beyond you.
If people want to learn more about your or your business, where should they go?
If people want to learn more about me or my business, the best place to start is my website, WorkOnYourGameUniversity.com. That’s where you’ll find everything about my coaching programs, courses, and what we offer.
You can also check out my daily podcast, Work On Your Game, where I dive deep into mindset, strategy, systems, and accountability for high-performance individuals. For social media, I’m active on Instagram and YouTube, where I share a lot of content related to personal and professional development. My YouTube channel is YouTube.com/dreupt and on Instagram, you can find me at @DreBaldwin.
A huge thanks to Dre for doing this, and if you want to hear more about his story and advice, you can actually check out an old podcast I recorded with him here:
And if you have any questions or need any help on email list/social media growth, let me know.
Have a great day,
- Josh Schachnow
Canadian immigration lawyer, CEO at Visto.ai