@Vib G Yor Yeah I get that some questions aren't relevant to the post and series. But to your second paragraph and point about capital gains, all of that IS totally relevant to the post and series. I think this is the first person profiled whose income comes from capital gains, and yet it goes unremarked upon. That's all I mean -- there were opportunities to point out that he does pay lower taxes and ask questions about that, especially given the theme of the series. Again, it doesn't need to be confrontational; avoiding discussion of it is weirder, to me.
Where to start with this. Well, for one: I think that if you're going to include this interview as part of the Tax Month series, which makes a lot of sense, it strikes me as a missed opportunity to not ask why his tax rate is so, so low (like not even 30% of his adjusted income when it should be closer to 33% at the very least, though admittedly I'm not the best at this sort of math so I'm totally open to having this explained to me). I'd be curious to know how he feels to be paying a similar rate to someone making around 40k a year. I mean I knew what I was getting when he said "Having a high tax bill is always good news for me, because it means I had high income," and while I don't need him to say that he loves to pay taxes because it's the right thing to do, I do want the person interviewing him to ask more probing questions. Maybe that's not fair, but I'm always curious to know if people as rich as him feel like they're paying their fair share, especially when they have so many ways to get out of even paying the bare minimum of that. And that doesn't have to be a confrontational question! But this interview just kinda reads like the interviewer was so impressed by the high numbers that every question is some version of "What's that like?" Also, I appreciate the last line about him not feeling qualified to give readers of this site advice. Especially when it's not at all clear how he made his money and why he was able to retire at such a young age. If it's family money I certainly don't know what advice he could give a Billfold reader about making or managing money (although I've been surprised how many readers of this site talk about inheritances). I don't know why I'm so annoyed! But reading this article felt like walking in on the end of a conversation after missing relevant details, so I'm left feeling like "wait, what?"
@Vib G Yor This is fascinating. I want you to write an article about it!
@Ester Bloom Nah, Goofus always seemed way more fun (and way less smug) than Gallant. Cheap just sounds like a huge pill.
This really is so interesting. I'm also curious about the emotional side of things. Like, did you feel like you were doing what your dad wanted by hanging in there for as long as you had? Did it make you understand your dad better in a way you hadn't before? I have tons more of the same type of question, because in my own mind I'd wonder if he'd be proud, or maybe a little sad that it represented such a drastic change of career course (or some combination of the two) and whether I'd done "right" by him (whatever that even means).
@jfruh Is it too late? I want you to see your sister in DC. I feel like 6 months from now you'll remember the time you had with her more than you'll remember the exact amount you saved on a flight. And, yeah, setting foot in NYC means setting your money on fire, so I truly believe you'll come out ahead by shortening your stay.
My Gen X is showing, but I really wanted this story to end with you taking the Singles DVD.
@jmdj I had a moment like that with Eshakti the other day. I had a coupon and there was a sale, but after spending so much of the day visiting the page and navigating away from it, I realized that I was forcing the issue for the sake of "saving" and finally closed the tab. It was kind of liberating to come to that realization though, and I need to remember it throughout the year.
@Jake Reinhardt It kind of sounds like you're using your anecdote about riding the subway to challenge this actual person's lived experience of being black in NYC. She's not naive to NYC's problems, given that she literally cites some of them in her piece. But as she also points out in her piece, there are a lot of comforts in NY that are absent in Madison/the midwest. So, given that, I wonder what's at stake for you in nitpicking her about her own reality and saying that New York is no better than the world she left behind? Also, what's productive about saying "the same problems exist everywhere" when she's talking about a specific set of experiences in a specific place? It reads as condescending and dismissive, as though you wouldn't want her to have the wrong impression of her own experience or the last word about it here.
This was hilarious and charming and I want to read more, please.