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OH SH*T! What if I die? Worries of multi-millionaire founders of business and the solutions that wil

It has been said, and proven to be true time and again, that the two groups of people who worry the most about money are the poorest of the poor and the richest of the rich. Both ends of the continuum place families in positions that exacerbate and amplify the same daily challenges faced by everyone. Obviously being a “have” certainly provides more security and comfort in life, generally. However when you’re wealthy, the amplification of trouble happens quickly and sometimes famously. It is often public and spectacular. The opportunities and challenges before you layer on top of one another and everything you do is done with larger scale. Even your hobbies need infrastructure.

In over twenty two years of guiding millionaire families to realize their bigger impact in their lifetimes and beyond, I have had hundreds of confidential closed door conversations about the biggest fears and challenges facing people and their wealth. As an adviser, consultant and coach, I have had the privilege to work alongside affluent entrepreneurs struggling with everything from taxation and investment planning, to preparing their next generation for success while stemming the biggest threats to a family’s wealth. No two situations are exactly the same.

There comes a time in a business owner’s life where they look ahead and behind at once. Their past a series of successes and failures, of lessons learned and lives impacted. Most look back with gratitude and appreciation of the accomplishments in their lives. What they see in the future is their possible life without work, pursuing their most coveted pastimes and passions full time. They see a long life ahead of them and the world is their oyster. Yet they are concerned about funding that life – yes that is right – those with the most actually do fear they might not have enough. This is not logical, from an empirical standpoint, but it is an incredibly strong emotional belief that somehow they won’t have enough to live the life they desire, leave the legacy they hope to and never, ever, slide into the darkest, hardest times they’ve experienced as entrepreneurs building their own empires. In many cases of big success, these people have risked everything and nearly lost everything – multiple times. Going from covering payroll on credit cards to big profits. This life experience is something they loathe to repeat. When they look backwards, they see lessons learned, missed opportunities and incredible successes. Their identity is wrapped up in their business and their business is wrapped in their identity. For decades it has been one in the same.

When they arrive at this point in life it is monumental. I call it the “OH SH*T!” moment. It is the realization that you might finally move beyond your business. This could be on your own terms, but it is quite possible your health or other outside factors could dictate it. So often the case, the wealthiest entrepreneurs are not prepared for what the future might bring, the risks that face them and their wealth, and preparation of their families for their own affluence.

This point of self-realization is regularly met with relief by all those people in the entrepreneur’s inner circle. They have been hoping, urging and imploring the owner to take care of some important planning for this eventuality. They have been frustrated and will be relieved you found the motivation to move forward. Their motivations of concern for your well-being are real. Their own life outcomes have been largely dependent upon your decisions and actions. Self-preservation has been on their minds, but out of their control as they serve you and the business. What they ultimately don’t understand is that, until this point, you never had to do anything at anyone else’s pace – at least from your perspective – because you are wealthy and in control. No one has or will dictate to you when you act. You can buy what you want, invest when you want and travel where you want at your pace. Very few things, events or people can change that. People without the self-made affluence you have do not understand this.

They also don’t understand that you really truly don’t know how to think about your money. No one has taught you. You were excellent at creating wealth and growing a business with your unique vision. You have learned the language of your business and industry, but you don’t know all the language of trusts, estate, liabilities, investment, insurance or taxes that threaten your hard earned wealth.

Now, the one thing that will bring you to action that you did not plan on is the stark realization of your own mortality. The sudden, ominous realization that you are mortal, that you’re are not finished doing whatever it is you intended to accomplish and the people around you who you love, would not be prepared or protected in the event your number was up…or if you were incapacitated. Once your health is in jeopardy, your family, your business, your wealth – all would be at risk. It is this moment that will change everything.

Do not hesitate or procrastinate. Great coaching takes time, great planning is sequential and implementation moves at its own pace. Your solutions might be easily and quickly implemented or they could take months or a year to be completed. Even if you start tomorrow, that is one day too many to delay. Don’t hesitate to reach out to those who can help. Start today.

Mike Skrypnek,

3 Time Author, International Speaker and


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