#364: From Poker Table to Boardroom Table: Casey Cavell on Lessons Learned After Leaving Poker & Turning a $9,000 Investment into a Business Portfolio of Over $40,000,000

In my interview today with Casey Cavell, we explore his journey transitioning from a professional poker player into a successful entrepreneur, real estate investor, and podcast host of the Dugout CEO podcast. He took a $9,000 investment and effectively used his poker skills to enter the real estate market, later launching baseball and softball academies and expanding them to five locations in Atlanta, and grossing over $40M between all his ventures. Casey faced significant challenges when he started to get burnt out. He was not living in his unique ability and was struggling with managing all the operations. Casey shares key lessons he learned on delegation, personal clarity, and aligning business goals with personal life. After reaching his personal and financial goals, he navigated the complex process of selling his stake in the ownership, transitioning from his W2 job, and most importantly, detaching his identity from the business. His story provides crucial insights into balancing perfection with acknowledging limitations, redefining self-worth, and drawing parallels between poker and business.

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Three Big Ideas From the Interview:

1. The Parallels Between Poker and Entrepreneurship: Casey's journey into entrepreneurship started at the poker table. The skills and strategies he honed in poker, such as understanding rules, money management, and self-assessment, were directly applicable to running a business. His initial investment of $9,000 into a six-unit apartment complex, made with poker earnings, demonstrated this overlap. It's a powerful reminder that often unconventional beginnings can provide unique, transferable skills that can be leveraged in entrepreneurship.

2. The Importance of Delegation and Focusing on Strengths: Despite his initial success, Casey learned the hard way that running a business was far more complex than he anticipated, leading to burnout. However, an investor's decision to help with managerial responsibilities allowed Casey to focus on his strengths, namely, creating efficient systems and scaling the business. This highlights the crucial nature of delegation, understanding personal strengths, and the need for effective partnerships in entrepreneurship.

3. Redefining Success Beyond Financial Prosperity: The story of Casey is also a tale of personal transformation. After battling feelings of inadequacy and a need to constantly prove his worth, he found contentment through his Christian faith. He then redefined his measure of success to include being a good father and husband, not just a successful businessman. This personal transformation underscores the importance of defining success beyond financial prosperity and the role of personal growth in entrepreneurship. His advocacy for clear goal setting, the use of an accountability coach, and living intentionally echo this sentiment, reiterating that business success involves having a clear vision for one's life and business.

Interview Quotes:

07:25 - “I realized that kind of working in my business rather than working on my business was me like playing poker because you can only make money if you played.” - Casey Cavell

20:04 - “Looking back at it, I probably wish I stayed in it [Real Estate]” - Casey Cavell

23:58 - “Yeah, and I think managing that amount of people when I myself was not a good manager is what led to my burnout.” - Casey Cavell

24:53 - “At least thought at the time, nobody could do it as good as me. And was it true? It probably was for a lot of the business, but for some of the business, it wasn't.” - Casey Cavell

25:10 - “I was worried about how do I take this business from 1.5 in revenue to 1.7 when I should have been thinking 1.5 is good if I don't have to be there anymore.” - Casey Cavell

38:57 - “If you’re doing [business] with people you don’t like to work with, or don’t really enjoy spending time with, it’s going to be brutal.” - Casey Cavell

43:57 - “I think a lot of people, they're so busy building their businesses, they're not building themselves.” - Casey Cavell