Introduction

A hard thing about business is minding your own.

—Unknown

I come from a family of competitors. Whether it’s a game of Monopoly on Thanksgiving or early mornings on the basketball court, we’re bonded not just by blood, but by the drive to win.

From the time we could walk, my brother and I were out on the field or the court playing whatever sport we could: basketball, football, baseball, or even games that we invented ourselves; you name it. We’d stay out sunup to sundown, playing until our mother rang the bell for us to come home. We didn’t know theater and we weren’t big readers, but boy, did we love playing any kind of ball.

Over the years, the more I’ve thought about it, the more I’ve realized that everything I know about life, I learned from sports.

Growing up, our coaches instilled in us the pursuit of excellence. Their methods were simple—they made sure we worked harder than everyone else, and they drilled into us the importance of not only mastering the fundamentals, but building an athlete’s mindset. We learned to develop a quiet confidence, a belief that we could compete against anyone and persevere through anything. Most importantly, my coaches believed in teaching us not only how to win—but how to lose.

When you understand losing, the sensation of pain and disappointment never leaves you. To be a competitor, and to play to win, you must commit yourself wholeheartedly to avoiding a loss at all costs. You have to live with tough emotions. You have to be able to rebound from a setback and better yourself for the next battle. More than anything, you have to keep going. You can’t quit. You can’t abandon your purpose.

I believe that the strength to recover from loss requires, above all else, personal fortitude: the resolve to stay true to your fundamental beliefs, no matter what life throws at you.

As an adult, I looked back on my childhood of sports with incredible gratitude. I wasn’t facing a countdown clock or an opposing defense anymore, but my problems as a professional seemed just as high-stakes as a shot to beat the buzzer. Thanks to the years I’d spent honing my fortitude as an athlete, I was always able to tackle big problems with determination and see them through to the end.

When I became a financial planner, I was suddenly on the other side of the desk watching clients face the biggest problem of their lives: how to plan their retirement. I was now the coach, trying to instill the same principles I’d learned playing sports.

Make no mistake—planning a retirement is a mountainous task. Add on the ambition many of my clients have to pass down wealth through multiple generations, and they find themselves staring down a goal they have no idea how to accomplish. They don’t even know where to start.

If you’ve faced the same problems and uncertainties, or if you’re facing them right now, then you are the person for whom I wrote this book.

Success Begins with Fundamentals

As a budding athlete, I sweated through early morning practices nearly every single day. We always started with the same thing: drills. Our coaches would run us through the fundamentals of the movements we needed to master over and over. We practiced these drills so consistently that they took root in our instincts. We didn’t know it at the time, but we were building life skills that meant more than almost anything we learned in school: that success is even more difficult without unwavering fundamentals and discipline.

As a wealth manager, this is where I start. If my clients don’t understand and practice the fundamentals, then no amount of advice and planning will bring them satisfaction and security.

Please understand that finding success and financial independence is a marathon, not a sprint. You must wake up every single day and know inside and out the goals you want to achieve. You need to design a clear playbook with your endgame in your mind, with full color and intricate detail. No matter what that goal looks like, making it a reality takes the personal conviction to stay the course.

Put more simply, you must first determine where you are today. Then determine where you want to go. Finally, you need someone to help you fill in the gaps and guide you along the way.

Like any sport, you can’t win with a team of one; and when it comes to planning multigenerational wealth, you’re playing a long game. People are living longer lives these days, and the ten- or twenty-year retirement of your parents’ generation has become a thirty- or even forty-year stretch. That’s a long playing field, and you’ll need enough money to get you all the way to the end. Additionally, you’ll face considerable obstacles—like inflation, for instance, which is no friend to a four-decade retirement. Planning your retirement is possibly the biggest problem you’ll face at this point in your life. There is no boilerplate template to solve it.

That’s my aim with this book. You will see what a vivid picture of multigenerational wealth looks like and how you build the mindset necessary to achieve it.

By the time you’re done reading this playbook, you’ll know the drills you need to practice to master the fundamentals. You will know the enemies you face and how you should approach them. You will also know how to assemble your team of coaches, who will help you get all the way down the field with the ball.

You’ll gain a stronger grasp of the questions you need to ask yourself and your professional advisors in order to reach your goals, and you’ll finish with a better understanding of how to approach your planning and the various facets of multigenerational wealth that need to be addressed.

Even more importantly, you will feel more confident that you can make smart decisions for yourself and your family and that there are solutions within your grasp. Confidence typically translates into better decisions, and better decisions result in better outcomes.

The Goose, the Gold, and You

A friend of mine who’s been very successful in business once admitted to me, “Every day, I wake up and go to work out of nothing more than fear.” His fear was not being able to take care of his family or not being able to maintain his family’s lifestyle.

At first, his comment seemed unusual. Why would he be scared? I wondered.

Then, I quickly realized that I felt the same way. I, too, felt the fear of failure. The same feeling is true for most people, and especially so for entrepreneurs. When you own a business, it’s all on you—the successes, the disappointments, the possibility of multigenerational wealth, and the potential for crushing loss. On a fundamental level, your goals for your business are simple. You want to provide for your family. You want to have the money to feed, clothe, and shelter them. You want to pay for their education and spend quality time with them on a vacation every once in a while. The possibility that your business might not do well enough to provide for those goals—the fear of failure—is understandably a source of pressure.

Here’s the bottom line: the stress you’re feeling is perfectly normal. In all honesty, this fear of failure is probably responsible in no small way for your success.

But Paul, you’re thinking, I don’t want to go to work afraid every day.

Understood. Let’s try thinking about your business differently. For you, it’s more than just a company; it’s your livelihood. Your business is your own personal goose that lays golden eggs—figuratively, of course, like the fairy-tale creature. You’ve nurtured your goose over the years, in good times and bad. As it has grown and will continue to grow, it’s laid eggs of different sizes and quantities. It’s up to you to watch over your goose and ensure that it stays healthy, all the while realizing that nothing in the future is certain.

Your goose might fall ill or the goose might grow old, resulting in fewer eggs. Your business may hit a rough patch, the market may shift, trends might change. There may come a time when you, the caretaker of the goose—the person whose heart and soul is ingrained in your company—get sick or become incapacitated. What then? Who will care for your business?

The truth is that the care and management of your business is encompassed in all the different facets of wealth management planning.

Yes, wealth is about your company, but it’s about taking care of yourself and your family as well. Without you, who will be left to keep things going? Many of our clients admit they’ve never thought about their business and its care in this way, but it’s been helpful for them to understand how many contingencies they need to plan for.

Business owners face three main financial concerns.

1. The first involves taking care of the goose, making sure your company stays healthy, so it will continue to lay golden eggs.
2. The second...