Money at 30: “The Winning Playbook” Book Review

Earlier this summer, I opened my email to find an unsolicited PDF copy of an upcoming book in my inbox. Well, it was upcoming back then but, now, The Winning Playbook: Strategies For Life On And Off The Field by authors Rob Welsh and Jonathan Ray Scott is available to all. So, with the football season (and, in turn, my fantasy football season) now well underway, I decided to spend the weekend reading The Winning Playbook to see what it had to over.

Over the past few months, I’ve mentioned a few times that a book I’m reviewing wasn’t exactly meant for me. In the case of The Winning Playbook, that’s even more true. That’s because the book is aimed at professional athletes. Even more specifically, the authors tailor much of the details to the National Football League — which makes perfect sense seeing as Scott is a second-generation NFLer.

As someone who reads a lot of personal finance books, it turns out that the football elements were among the most fascinating to me. For example, I was surprised to realize that players need to pay taxes to multiple states since away games count as income earned elsewhere. Also, it turns out that NFL players can’t access or even rollover their league-sponsored 401(k)s until they’re at least 45 years old (so I guess Brady’s good, at least). While these types of specifics are merely interesting to me, they’re vital to the target audience.

In addition to these sports-centric revelations, there were a couple of personal finance elements that I’d either read little about before or was reminded about from The Winning Playbook. Among them were discussions about indexed universal life insurance policies, captive insurance policies, and more. Meanwhile, while I’m familiar with the argument for choosing a 30-year mortgage versus a 15-year or paying cash, I thought it was interesting the way the book laid out this suggestion and tied it into the life of a football pro.

Unfortunately, while The Winning Playbook gets granular on some issues, the book is thin in many other areas. It’s also quite literally thin, coming in at 142 pages. Because of this, I kept finding myself feeling as though I was being teed up for a deeper dive… only to be pulled back to the surface. Similarly, although I appreciated the sentiments behind such suggestions as “become an athletepreneur,” I thought there could have been a lot more material on making that happen or even highlighting some potential paths.

With that said, the book does feature some solid “personal finance 101” insights. Retirement accounts, types of investment options, budgeting, the reality of taxes, and more are all covered. But, once again, it’s rare that many of these topics get more than a few paragraphs, so readers who are just hearing about these concepts will likely want to do some additional research after the fact.

Closing out the book is a collection of interviews with a variety of athletes. Following the book’s focus, the majority of these are NFL alums, although baseball, soccer, and other sports are also represented. Yet, while there’s a mix of players, the questions asked remain the same throughout. Having such a format isn’t necessarily a bad thing but it would have been nice to dig a bit deeper with some of the interviewees. Nevertheless, I enjoyed this capper to book overall, and it built a bit on that “athletepreneur” concept at times.

Overall, for those in the presumably limited target market, The Winning Playbook: Strategies For Life On And Off The Field is definitely something I’d recommend reading. However, I’d also suggest that they follow it up with a more in-depth financial read. As for those who aren’t professional or aspiring athletes, while I wouldn’t discourage giving this book a read, I also don’t think it will be that impactful.


Kyle Burbank

Kyle is a freelance writer and author whose first book, "The E-Ticket Life" is now available on Amazon. In addition to his weekly "Money at 30" column on Dyer News, he is also the editorial director and a writer for the Disney fan site and has recently starting publsihing his own personal finance blog at

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