Latest / The Liquidity Event | Money and Finance with Shane and Ally Jane / AI, Money, and Modern Dating - Episode 156

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AI, Money, and Modern Dating - Episode 156 · The Liquidity Event | Money and Finance with Shane and Ally Jane

• 0:00
  AJ: I am Allie Jane, AJ.
• 0:10
  Shane: And this is episode 156, being recorded on August 27th and airing on August 28th. You can email us your finance questions at liquidityevent@brooklynfi.com. If you don’t, we’ll pull them from Reddit. If you do, we’ll answer them live on the air. AJ, how are we doing this week? Where are you in the world?
• 0:20
  AJ: I’m doing great. I am in Palm Springs, California. It’s 7:00 AM, and I’ve been up since four getting things done. I’ve been on a walk. This is my happy place. For those of you that don’t know, I often retreat to the desert because I am, in fact, a lizard in human form.
• 0:30
  Shane: Is that when lizards wake up? 4:00 AM, when the sun cracks over the edge?
• 0:40
  AJ: Exactly. Lizards follow the heat. During the day they sit on hot rocks to warm themselves up. I love the ultra-dry, ultra-hot desert air. That’s the lizard quality I’m referencing.
• 0:50
  Shane: Love to see it. Where in the world are you?
• 1:00
  Shane: I am back in Greenpoint after a week away at camp. Counselor Shane was in full swing—“Can I have a Starburst? Can I go over there by myself?” The answer was always no. It was my fourth year at camp. Pretty wild.
• 1:10
  AJ: Can we get 30 seconds on what type of camp this is?
• 1:20
  Shane: It’s tough to answer without sounding like I’m virtue signaling, but it’s a grief camp where I volunteer. It’s for kids who’ve lost one or both parents, or whose primary caregiver might be a grandparent, sibling, or cousin. It’s 95% camp—free for the kids, great facilities—but 5% therapy. Clinicians are on-site, so there’s space for crying, anger, and healing. For the 13-year-olds I had this year, it was more fart jokes and testing boundaries than tears, but that’s part of it too.
• 1:30
  AJ: How did your experience at grief camp compare to our Brooklyn FI retreat two weeks ago?
• 1:40
  Shane: Honestly, there was more crying at the BKFI retreat than at grief camp this year.
• 1:50
  AJ: That’s really awesome. I love that you do this, especially since you’ve also lost a parent. It’s such a powerful way to connect with those kids. They get to step out of tough situations, just be kids, but also have support from therapists and volunteers like you.
• 2:00
  Shane: Exactly. What we need most is more counselors. If anyone listening knows someone between the ages of 20 and 80 who can spend a week with kids, that’s the biggest need. The clinicians handle therapy, we handle the rest.
• 2:10
  AJ: And you’ve said you’ve made great friendships with the other counselors too—people who care deeply about the world. It’s such an interesting opportunity to meet like-minded adults.
• 2:20
  Shane: Absolutely. Some even fly internationally, using vacation days to spend a week volunteering. It’s really admirable.
• 2:30
  AJ: Yeah, the UK folks practically treat it like a bank holiday. Speaking of which, what even is a bank holiday?
• 2:40
  Shane: Apparently just a day when banks close, and everyone else gets a day off. Powerful bankers once decided, “We’re not working today,” and here we are.
• 2:50
  AJ: Sounds about right. Anyway, let’s get into the episode.
• 3:00
  Shane: On this week’s episode, we have young people putting off relationships until they’re making more money. OpenAI is warning that AGI will make money useless. We’ve got updates on the IRS, how they’re handling the big bill. A 401k company being sued for deceptive sales practices. And then a couple of Reddit questions about how to be a good billionaire and how often you should rebalance. AJ, what’s going on with you? You’ve got some notes here about AI.
• 3:10
  AJ: Yeah, I added this while you were at camp. I thought it’d be fun to talk about how we’re actually using AI in our daily lives. For me, I’ve been tracking what I eat. When I’m in California, surrounded by good food, I just graze all day. ChatGPT is great for accountability—it helps me log calories, reminds me of limits, and even stopped me from having that second margarita the other night.
• 3:20
  Shane: Nice. I use it every day without thinking about it. Recently I asked it to help me build a running program like Orange Theory, but for the track near me. It suggested gear, apps, and routines. I also asked for book recs about partnership decisions I’m working through. And the new GitHub integration is amazing—it can analyze my personal projects. Oh, and I sold my boat last week—it even helped me draft a bill of sale.
• 3:30
  AJ: Wow, RIP boat. Congrats though. I love hearing all these ways you’re using it. Instead of worrying about Sam Altman and Elon Musk dueling like Harry Potter characters, we can just talk about how we’re actually using it in daily life. For me, it’s been helpful but not life changing yet.
• 3:40
  Shane: Same here. I even tried having an AI agent scrape a sailing website for opportunities, but it got stuck at the “I’m not a robot” screen. So yeah, AGI isn’t here just yet.
• 3:50
  AJ: Exactly. It’s a fun tool, not a revolution. Let’s move on.
• 4:00
  Shane: First article—the New York Times reports people are putting off relationships until they earn enough money. Basically, money talk has moved from taboo to table stakes in modern dating. AJ, do you think this makes relationships more transparent or more transactional?
• 4:10
  AJ: I think people are afraid of relationships failing during their prime. Our generation wants to feel whole before partnering—whether that’s money, fitness, or family planning. Transparency and trust are key. Maybe not on the first date, but by the fourth or fifth you should be talking about expectations and lifestyle. But people also change phases in life—you and I both had ramen years and then things got better. So don’t write people off too soon.
• 4:20
  Shane: Yeah, though this article feels very coastal-elite. Someone in San Francisco making six figures but only having $500 left after rent—it’s not exactly a middle-America problem. Still, it highlights shifting gender roles and financial expectations in relationships.
• 4:30
  AJ: Exactly. A lot of this goes back to childhood too. If money was scarce or stressful when you grew up, you’re going to prioritize stability in a partner.
• 4:40
  Shane: Next up, Business Insider: OpenAI warns investors that AGI may make money obsolete—while raising billions of dollars. AJ, bold honesty or marketing ploy?
• 4:50
  AJ: Marketing. Money will still matter in the future—you can quote me on that. There’s so much hype, but most firms report little measurable return from AI so far. Altman may say the market is saturated, but he’s still raising billions for the next release.
• 5:00
  Shane: Agreed. AI researchers don’t necessarily understand finance. This feels more like overconfidence. Sure, revolutions can upend wealth, but mostly hoarded wealth persists. I think it’s marketing. And while some young researchers are going doomsday-prepper mode, I think we need to pump the brakes. These are smart kids, but not exactly seasoned philosophers.
• 5:10
  AJ: Right. I feel empathy for young people who’ve lost faith in humanity, but also—we don’t need to build bunkers yet.
• 5:20
  Shane: Moving on—the IRS has announced no changes to individual withholding tables for 2025 under the new bill. But there are new provisions: no tax on tips, no tax on overtime (for some incomes), deductions for auto loan interest, and a senior deduction. AJ, what do you think?
• 5:30
  AJ: I think people misunderstand tax code so badly. Once again, these updates mostly benefit the ultra-wealthy or very poor, not the middle class. People in the “living wage” bracket are excluded. And yes, I think our clients will be most affected by the Qualified Small Business Stock (QSBS) updates—potentially shortening the holding period from five years to three. That’s huge. If you work at a startup, do your tax planning now.
• 5:40
  Shane: Absolutely. We’ll run webinars once IRS clarifies enforcement.
• 5:50
  Shane: Final Reddit question—would you rather be a public billionaire or a secret billionaire?
• 6:00
  AJ: I’d pick a third option. We need positive role models who use wealth for good. Think Taylor Swift or Mackenzie Scott—giving generously, showing what’s possible. But anonymity is also appealing because you stay grounded and connected to real people. Fame isolates you from everyday experiences. If you’re wealthy, you need to make sure you still meet real people who don’t know who you are.
• 6:10
  Shane: I agree. Taking chips off the table is smart, but you can still do good. I’d probably lean toward being known for giving it away, like Mackenzie Scott. And yes—if I were rich, I wouldn’t be taking my shoes off at TSA either.
• 6:20
  AJ: That’s a great place to wrap up. Thanks for listening to episode 156 of The Liquidity Event. You can email us your financial questions at liquidityevent@brooklynfi.com. And if you feel like being weird, leave us a review.
• 6:30
  Shane: Thanks everyone.
• 6:40
  AJ: See you next week. Bye.