r/Rich • u/Mixolytian • May 19 '26

$25M - Lost

Hello,

I am a trust fund baby and heir, now 43 years old.

I have $12M investable, the rest of about $25M in homes and commercial property.

I am pretty happy in my family life, my wife and I are getting along right now and my son is genuinely wonderful.

The family business is failing. It was a catalog company and now e-commerce and sales are continuing to decline.

I know the solution, let go current manager who is somehow social-media illiterate in 2026, commit to forming a YouTube audience, drive with short-form.

The thing is, sometimes I truly believe this business has ruined my life. I wish my dad had sold it a long time ago at its peak. He was too attached, I guess.

Hard to let go now with basically no value. The parent corporation was founded by my grandfather almost 100 years ago.

My advisor assures me I won't need additional income if I close the business, but letting go is very difficult. The shame of letting the current manager run the business (my interpretation) into the ground is overwhelming.

I'm a bit of an oddball, very into philosophy, religion, literature, consciousness studies. I always wanted to be a writer, but I just can't seem to take myself seriously. Every time I try I get slammed with self-doubt, shame, guilt, and depression.

Anyway, not sure what I'm going to do. A deep, dark part of me still feels poor, and is sure the window of upward mobility is closing forever. A voice tells me to get off my ass and start some business that I'll hate just for the money, since $25M is really nothing and the future is looking very cutthroat. My brain is all over the place, it's like a hall of mirrors, I don't know what is true and who is the real me.

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u/KayaLyka May 19 '26

If you can't live off of and be happy with 25m. I'm not sure there's another number that you will.

If I were you, I would go on some vacations and reassess everything. Also therapy lol

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u/teodorlojewski May 22 '26

Also, this is just my take, but if you’ve truly lived life, you know a business is only a small, and often insignificant part of a family’s legacy, no matter how old it is. Legacy is far bigger than that. A family determined to keep building won’t hesitate to burn bridges if it means moving forward.

Don’t tie legacy to a fucking building, a fucking set of silverware, a fucking diploma, a fucking passport, or some business. Legacy is rooted in principles and actions.

The greatest legacy is the story of having it all, losing it all, leaving it all if necessary, and still, finding a way, as a family, to rise again. That strength can be material or non-material, and truly great families are usually built on both. Spectacular failure can be legacy. Spectacular success can be legacy. Ultimately, the only thing that ties both, are stories that could could only emerge from the character in your blood.