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Man’s Marriage Begins with a Hefty Prenup and Hefty Debt, But When Crypto Bets Fail, No One Saw This Threat Emerging.

Dear Top Dollar,

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My name is Steve, a 30-year-old man from a humble background, married to a woman from an affluent family. When we tied the knot, her net worth was around 31 million dollars, while I had over $150k in student debt. Per her family’s insistence, we established a prenuptial agreement separating her inheritance from our mutual assets and nullifying my right to an “elective share.” This agreement was meticulously arranged and notarized by lawyers, hers significantly more costly than mine.

Initial Response

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At the start, I was fine with this arrangement. Believing in the virtues of self-reliance and hard work, I intended to pull myself up from my situation without tapping into my wife’s fortune. One advantage for me was that our incomes were also separate, and I earned slightly more than she did. So, despite her vast wealth and my minimal resources, I was comfortable with our financial disparity.

The Tides of Fortune

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Fast forward to eight years later, I still own a fraction of her current wealth, but her financial standing hasn’t been very rosy recently. Despite my caution against it, she invested heavily in cryptocurrencies and a sizable amount in one called “Monero,” which has plunged over 40 percent from her entry point. She also lost a significant chunk of her money when FTX, the exchange she used, went bankrupt. As of now, her net worth stands at approximately 18 million dollars.

The Unraveling

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Recently, she broke down over the financial losses, accusing me of being indifferent to her predicament. I reminded her that she still possesses significant wealth despite her poor investment choices and that she could stop the high-risk investments whenever she chooses. I further pointed out that it was her decision to separate our finances, so it seemed unfair that she would suddenly desire my involvement in her monetary issues.

Seeking Advice

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As I pen this letter, I’m seeking your advice on how best to handle this situation. How do I empathize with her financial loss without compromising my principles of self-reliance and financial independence? Is there a way I can assist her without merging our finances? Also, should I discuss with her about diversifying her investment portfolio, and if yes, how should I approach this sensitive subject?

Yours faithfully,

Bootstrap Believer

Dear Bootstrap Believer,

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Your situation is indeed complex. The first piece of advice is to be empathetic towards your wife. Despite the financial divide, it is essential to understand her emotions and concerns about her losses. Your marriage goes beyond mere financial arrangements, and her current state of distress needs emotional support, not just logical analysis.

Separation Isn’t Disconnection

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Just because your finances are separate does not mean you are isolated from each other’s financial realities. You can offer advice, help her strategize and even learn from her experiences. By doing so, you’re maintaining your self-reliance and financial independence while also being involved in her financial journey.

Money Talks

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Given your letter, it seems that you have a solid grasp of diversification and risk tolerance. I think your main challenge is to find a compassionate way to share this knowledge with your wife without acting judgmental or condescending.

Given the current state of affairs, it would be prudent to have an open and honest discussion about money. Encourage her to diversify her investments and make informed decisions. Approach this sensitive topic with care, ensuring she understands that your advice is for her financial well-being.

Her fortune is still extremely significant, putting her wealth in the top 0.01% of the country. Even with conservative investments, she should be able to produce a sizeable passive income return of over $500K per year. Perhaps you can discuss your future financial needs and goals and determine if it is necessary to take on ‘riskier’ assets given her still substantial net worth.

Remember, avoiding permanent capital loss and considering one’s individual risk tolerance should ALWAYS be contemplated before undertaking any investments. This is a key step to building a sound financial plan.

Standing by Your Principles

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While assisting her, it is crucial to uphold your principles of self-reliance and financial independence. You can help her without compromising these values. Remind her of the reason you chose to separate your finances initially and explain why it’s still important to you.

Seek Professional Assistance

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Lastly, if these discussions and actions don’t help improve the situation, consider seeking help from a professional financial advisor. They can provide neutral, objective advice and assist in creating a balanced, diversified portfolio, which may be more suitable for her needs and risk tolerance.

Although you seem to utilize a more ‘Do it Yourself’ style, which I commend, perhaps your wife needs an outside opinion to provide the necessary support for her to modify her investment behavior.

In your position, you can find an “advice only” advisor who would not take a percentage of your assets, which would be too considerable to give her $17 million. However, this advice could still offer support for the investment pillars you seem to embody on your own for a minimal cost.


Top Dollar

Who Is Top Dollar?

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Josh Dudick is a financial expert with almost two decades of experience as a professional money manager, investment strategist, and venture capital investor.

Josh has held several senior roles at prominent Wall Street institutions and now focuses on leveraging technology within finance. In 2019 he founded his own investment fund and launched Top Dollar Investor in 2022 to help spread financial literacy and insights he has used to build wealth.

Josh graduated from Cornell University and holds a degree in Applied Economics & Management from the Dyson School at the SC Johnson College of Business.

Have a Question For Top Dollar?

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Send a message to Top Dollar.

By sending us questions, you agree to have them published anonymously by Top Dollar Investor Inc.

Although Josh is a financial expert, his responses do not constitute an act as a fiduciary or financial advisor. The content provided by Top Dollar is provided for educational and informational purposes and does not constitute a recommendation for any particular security or investment strategy. Information should not be taken as professional financial, legal, or tax advice.

Josh Dudick

Josh is a financial expert with over 15 years of experience on Wall Street as a senior market strategist and trader. His career has spanned from working on the New York Stock Exchange floor to investment management and portfolio trading at Citibank, Chicago Trading Company, and Flow Traders.

Josh graduated from Cornell University with a degree from the Dyson School of Applied Economics & Management at the SC Johnson College of Business. He has held multiple professional licenses during his career, including FINRA Series 3, 7, 24, 55, Nasdaq OMX, Xetra & Eurex (German), and SIX (Swiss) trading licenses. Josh served as a senior trader and strategist, business partner, and head of futures in his former roles on Wall Street.

Josh's work and authoritative advice have appeared in major publications like Nasdaq, Forbes, The Sun, Yahoo! Finance, CBS News, Fortune, The Street, MSN Money, and Go Banking Rates. Josh currently holds areas of expertise in investing, wealth management, capital markets, taxes, real estate, cryptocurrencies, and personal finance.

Josh currently runs a wealth management business and investment firm. Additionally, he is the founder and CEO of Top Dollar, where he teaches others how to build 6-figure passive income with smart money strategies that he uses professionally.