Aug 5, 2026 · 51 min · 12 segments
Keith Alpert spent most of his life with almost no view into his family's wealth — until a single conversation turned him into the full-time steward of his father's estate. Six years, and one $100…
Keith AlpertGuest
Ali KatzHost
And so, you know, a-as people are hearing this, and they may be in a situation where, um, they're thinking about how to approach their parents about it because, you know, there...

I think there was also a context where you said somebody approached somebody, and they were called a gold digger.

So this was, um, on the other side of the equation that the father, who again, my, my fiancée and her sister don't have a great close relationship, and, you know, even all their years growing up 'cause their parents got divorced very early on, and, you know, he's been a bit of an absentee father in a lot of ways.

Um, but, um, I don't know, a few years ago we went down, and we visited with him, and we had a really nice visit, and then after the visit, um, um, my fiancée and her sister decided to, you know, compose an email to the father knowing that I was very involved in, in this whole estate planning and getting the ducks in a row and all that.

They sent him, you know, um, which would be considered not really an aggressive email but just an email that's out of care saying, "Hey, you know, like, not sure if you thought about this, but just wanna make sure that you've got a will in place and the proper people."

And, like, he just totally took it the wrong way as if, you know, these people that don't even have a relationship with me want me to put this stuff in place, they can only want one thing.

... you know, the pushback on that, and things have not been great, um, since then.

I th-I think that there's a lesson that we can, that we can learn from that, which is that the connection has to be there first, right? We've got to create a connection, and that can be hard.

You know? It's like how do we create that connection when there isn't a connection before we even start talking about the money or the will.

And my sense is that it could happen through the lens of wanting to make sure that you're taken care of, and I think that might even be how we approached it with your dad to begin with.

And so, you know, a-as people are hearing this, and they may be in a situation where, um, they're thinking about how to approach their parents about it because, you know, there...

I think there was also a context where you said somebody approached somebody, and they were called a gold digger.

So this was, um, on the other side of the equation that the father, who again, my, my fiancée and her sister don't have a great close relationship, and, you know, even all their years growing up 'cause their parents got divorced very early on, and, you know, he's been a bit of an absentee father in a lot of ways.

Um, but, um, I don't know, a few years ago we went down, and we visited with him, and we had a really nice visit, and then after the visit, um, um, my fiancée and her sister decided to, you know, compose an email to the father knowing that I was very involved in, in this whole estate planning and getting the ducks in a row and all that.

They sent him, you know, um, which would be considered not really an aggressive email but just an email that's out of care saying, "Hey, you know, like, not sure if you thought about this, but just wanna make sure that you've got a will in place and the proper people."

And, like, he just totally took it the wrong way as if, you know, these people that don't even have a relationship with me want me to put this stuff in place, they can only want one thing.

... you know, the pushback on that, and things have not been great, um, since then.

I th-I think that there's a lesson that we can, that we can learn from that, which is that the connection has to be there first, right? We've got to create a connection, and that can be hard.

You know? It's like how do we create that connection when there isn't a connection before we even start talking about the money or the will.

And my sense is that it could happen through the lens of wanting to make sure that you're taken care of, and I think that might even be how we approached it with your dad to begin with.
The rest of this transcript — segmented and speaker-labeled, so you land on the exact moment something was said
Search every transcript — by keyword, by phrase, or by meaning, across every show Radar indexes
Trends — what is surging across podcasts, measured against its own baseline
Alerts — when a name you follow appears in a newly indexed episode
No account is needed to search Radar.