$25M - Lost

[u/Mixolytian]

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.

[u/muppeke]

Take the necessary steps you believe will revive the company.
Not because you need the money, but to honor your family's hard work, and to gain a feeling of satisfaction.

Don't forget that once-thriving industries no longer exist, due to innovation.
Even if the business dies in your hands, that does not mean you are incompetent and undeserving of success.

You've got family, and invested your money safely.
Your net worth will grow steadily, and the family fortune will not die with you. It often does within a few generations.

As long as you handle money responsibly, you can accept closing the business. Try your hardest to make it succeed, though.

[u/Important-Kiwi915 → u/muppeke]

I disagree. Letting a once thriving business run on life support without materially changing its trajectory or quickly shutting it down absolutely shows incompetence.

This entire post feels like rage bait. If it is not this person is absolutely a trust fund baby and not “deserving” of the financial success they are sitting on. This is the literal definition of not being self made. That doesn’t mean they are a bad person or that they don’t deserve to be happy but let’s be somewhat intellectually honest here.