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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this episode of The Money Mondays, host Dan Fleyshman sits down with Bradley Sugars, founder of ActionCOACH, one of the world's largest business coaching organizations operating in 85+ countries. (00:02) Brad shares decades of hard-earned wisdom on what truly separates struggling operators from successful business owners, from why most entrepreneurs stay stuck doing $20/hour tasks to how real wealth is built through systems, coaching, and accountability. The conversation explores the fundamental differences between being a great operator versus a true owner, why "how" kills most goals, and the psychology behind setting challenging versus "wimpy" goals. (09:19) They dive deep into investing strategies, the importance of having written investment rules, and why talking about money openly is essential for building wealth and strong relationships.
Australian entrepreneur, father of five, and founder of ActionCOACH, the world's largest business coaching organization operating in 85+ countries with over 1,100 offices worldwide. (00:47) Brad has authored 18 books on business and investing, several of which are international bestsellers, and his companies have generated billions in total revenue over the years. He teaches approximately 40 days per year and focuses on helping people understand and master money through systematic approaches to business growth and wealth building.
Host of The Money Mondays podcast and serial entrepreneur who became the youngest founder of a publicly traded company in history. Dan conducts high-level one-on-one coaching for charity at $100,000 per session, having raised $2.7 million for various charitable causes. (05:21) He's passionate about changing the narrative that talking about money is taboo and focuses on helping ambitious professionals learn how to make, invest, and give money away effectively.
The fundamental difference between successful and struggling entrepreneurs lies in their ability to evolve from being great operators to true business owners. (02:42) As Brad explains, "Too many great operators never learn how to be an owner and therefore they're still doing $20 an hour tasks rather than employing people to do all those tasks." This shift requires developing systems, hiring the right people, and focusing on strategy rather than daily operations. The key is building management teams that become experts at the job while you focus on leadership and growth. Many entrepreneurs get trapped in the operational details because it feels comfortable and familiar, but true wealth comes from stepping back and building scalable systems that don't depend on your constant involvement.
One of the biggest goal-killers is getting trapped in the "how" before committing to the goal itself. (10:15) Brad emphasizes that "most dreams die on the how table" and explains his success formula: "dream, goal, learn, plan, act." The goals should determine what you need to learn, not how to do it immediately. If you already know how to achieve something, it's not a goal—it's a to-do list item. (11:38) By definition, meaningful goals require growth and learning. This mindset shift allows you to set bigger, more challenging objectives that force innovation and personal development rather than limiting yourself to what you currently know how to accomplish.
Brad advocates for setting what he calls "crazy goals" that seem impossible at first glance because they lead to amazing innovations. (08:49) Using Elon Musk as an example, he shows how the goal of settling Mars led to breakthroughs in rocket ships, drilling technology, communication systems, and robotics. The problem with most business people is they don't challenge themselves with goals big enough to require significant innovation. (09:34) A billion-dollar business plan takes the same time to write as a million-dollar plan, but most people don't think a billion is normal. Setting massive goals disrupts your current business and life in positive ways, forcing you to develop new capabilities and think beyond incremental improvements.
The cardinal rule for successful investing is to focus on areas where you already have deep expertise and knowledge. (18:42) Brad's philosophy is simple: "Invest where you're an expert. Invest where you're dang good." If you've spent 20 years learning business, invest in businesses. If you understand accounting firms, buy more accounting firms. (20:14) Rather than trying to learn new investment categories like NFTs or cryptocurrency, leverage your existing knowledge base. Most people become gamblers instead of investors because they chase opportunities outside their expertise. The key is having written, documented investment rules and spending time learning before deploying capital. (17:53) As Brad notes, "you're not an investor unless you have a written documented set of rules."
Breaking the cultural taboo around money conversations is essential for building wealth and strong relationships. (22:48) Brad challenges the notion that it's rude to talk about money, asking, "If I don't talk about it with my kids, where are they getting their opinions from?" (23:36) He advocates for creating environments where money, politics, and other important topics can be discussed openly among friends and family. Brad even started a group called "Handsome Men's Club" to facilitate these conversations among men, recognizing that we live in one of the loneliest periods in history despite being more connected than ever. The practical application includes setting up wealth accounts with trusted friends or family as co-signers to maintain accountability in investment decisions.