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The Big Story: How to Use Gen AI to Argue with Yourself

I spotted this tweet back on Liberation Day, which honestly feels like a lifetime and approximately 5 Apple market capitalizations ago, but it stopped me in my tracks.

Now, before I continue, I will say that the aim of this post is not to advance this particular (conspiracy) theory. On the contrary, I want to show you how I used tools that are notorious for promoting confirmation bias to, in fact, do the opposite.

If you know me, you’ll know that this take didn’t read as all that outlandish to me, at least not at a glance. But I am a bit of a “digger” when it comes to getting intel — as my friends would say, I am quite Southern Italian 🤌 — so, jumped at the chance to see if ChatGPT would corroborate such a brazen claim, if prompted.

Almost immediately, the tool started spewing out concepts that felt eerily familiar to the contemporary environment. It provided nine total actions this so-called “compromised President” might take, including some familiar topics like disparagement of the Federal Reserve and general interference in monetary policy.

A few of these resonated somewhat, but this little bit about “weaponizing trade” seemed a little too timely.

In a more detailed description, the tool mentioned that one could “announce unpredictable tariffs and sanctions, especially against allies … driving volatility and encouraging companies to decouple from U.S. trade.” 

Well, sh*t.

Alright, my worldview was confirmed so time to shut it down, right? Wrong. That seemed easy. Way too easy. So I kept pushing.

I realized I couldn’t articulate the counterposition to this particular claim, which I think is something that many of us can relate to but few of us will admit — on a whole host of issues! So, I prodded: what would a rational person who disagrees with my established political leanings say?

This follow-on prompt emulates a painstaking exercise that I have been doing for years, which is — when I see a major piece of news break, I read about it from one of my preferred sources, and then I purposely seek out “what the haters would say.” That is, I want to know how someone with a completely opposing worldview, or even slightly differing opinion, would look at this very same topic. Now, this used to involve referencing my favorite chart in the world (The Media Bias Chart!) and viewing sources opposite my side of the spectrum. But now, ChatGPT can do this step for me.

Time to make Chat GPT fight … itself. 🥊

I’ll link s summary of the mock debate text here, but for the purpose of this newsletter — and the fact that there’s a LOT of market news to cover further down — here’s a condensed version:

Here’s why I like this exercise (AKA, what works fairly well): 

• It forces you to get outside of your own bias and empathize with what a rational actor on the other side of an issue might say. I used a political example here because it’s timely, but consider its applications within work settings, disagreements with friends, and the like.

• It’s a relatively quick way to distill counterclaims in an easy-to-follow format. I think this is super helpful during a time when a lot of heated arguments begin with one person pointing to topic A and the other pointing to topic B in response (e.g., “OK, but what about _____?!”).

• The tenor, when prompted correctly, is relatively devoid of emotion and hyperbole. My heart rate didn’t spike as I was reading it.

And here’s why this isn’t a fool-proof method (AKA, why Gen AI can assist EQ, but cannot replace it):

• No matter how much coaching is provided to the tool, prompts may be inherently leading or biased, depending on the author.

• This approach naturally puts each point “on balance,” when that just might not be the reality of the situation. Since the tool is being asked to follow a simple point/counterpoint format, the results tend to weigh the impacts of each bullet point similarly. For example, it may be the case that you believe — or the data may even show — that the magnitude of impact for one point outweighs the counterpoint. While there is rarely one “right” answer to hot-button issues, the tool necessitates a balance in the argument, which creates a “false equivalency.”

• Finally, while stripping the arguments of emotion is a nice respite from the chaos of the world, this approach can sterilize serious issues to the point where impacts or harms are diminished.

Bottom line: Stating the obvious, ChatGPT should not be used to outsource our decisions or shortcut our understanding of complex and important topics that affect our livelihoods and those of the people around us. Gen AI tools know a scary amount about us, but they couldn’t possibly encapsulate the nuances of our lived experiences and worldviews in such a sophisticated fashion — at least not yet!

But that said, we each have at our disposal unprecedented resources for searching for surfacing information from thousands, if not millions of sources, in literal seconds. AI isn’t just a shortcut to get to where you may intellectually want to go. In fact, it can be a multiplier of ideas that allows us to expand and grow our understanding of others and the world around us.

Daily Rip Live Recap: Hello and Goodbye to One of the Craziest Days in Stock Market History

Every weekday, Shay Boloor and I run down the biggest market news and events on Stocktwits’ morning show, The Daily Rip Live. Here’s what we covered during Wednesday’s show — but keep in mind, things went completely off the rails around midday, so I am including some of those updates, too.

From the morning show:

• 6:30 | My co-host Shay Boloor went on CNN earlier this week, and things got real. He voices his frustration around the policy whiplash. Watch the clip!

• 11:45 | Rand Paul and others in GOP are pushing back on the tariffs. This is neither here nor there, but Rep. Paul’s hair absolutely confounds me, and I admit I am a little bit obsessed with it. Moving on…

• 14:10 | Is the bond market broken? Who is offloading all those T-bills? $TLT ( ▲ 0.74% )  

• 20:50 | Macro factors are now completely dominating retail investor conversations. In the chat, some of our listeners lamented that we weren’t focusing enough on single stocks. Kind of hard to do when everything is being impacted by one person!

• 🚨 25:05 | Breaking news: EU confirms counter-tariffs on select goods.

• 27:55 | Robinhood CEO Vlad Tenev gives an interview to CNBC, which was interesting seeing as he’s sort of the voice of retail investors these days. At one point, he dodges a question about how long he wants to “personally” endure the financial pain caused by tariff threats. Another W in the books for his personal stylist. $HOOD ( ▲ 2.7% )  

• 33:00 | We discuss stocks making moves in the pre-market: Nvidia, Palantir, and Pfizer. Potential tariffs on international pharma are absolutely rocking some stocks in the sector. $NVDA ( ▲ 4.3% )  $PLTR ( ▲ 4.64% )  $PFE ( ▲ 0.62% )  

• 🚨 44:00 | Breaking news: POTUS pumps DJT on Truth Social mid-stream, telling people to “buy the dip.” — Huh? (This would all make a lot of sense in a few hours.) $DJT ( ▼ 0.04% )  

Of course, after we wrapped the show and got on with our lives, a 90-day pause on tariffs was announced, and the market began to rip at the first sign of relief. The Dow shot up nearly 3,000 points for the highest intraday gain ever. And while Sec. Treasury Bessent claimed market volatility had nothing to do with the decision, the President later admitted that the market was spooked and people were getting “yippy.”

Hear Shay and I yap about the markets every weekday at 9 a.m. ET on X (@stocktwits), YouTube, LinkedIn, or in your Stocktwits app. Follow me there — I’m @stocktwitsKP!

Now Here’s a Chart

How did they know? Here’s a chart showing an enormous amount of $QQQ ( ▲ 1.12% ) options volume ahead of yesterday’s announcement of a 90-day tariff pause. The Nasdaq ended up rallying 2,000% in a matter of minutes. I don’t think this is the last we’ll be hearing about this kind of thing…

Reading List

• Surprising China news sends Nvidia stock surging (The Street) $NVDA ( ▲ 4.3% )  

• Bond Breakdown: 10-Year Treasury yields fall after Trump’s tariff reprieve (CNBC)

• Why the C-Suite is embracing AI agents (Fortune)

• Trump reveals the next industry that will face imminent 'major' tariffs: pharma (Fox Business)

• Airlines’ Dreams of a Banner Year Are Clouded by Trade Battle (WSJ) $DAL ( ▼ 1.05% )  

• Wayve’s self-driving tech is headed to Nissan vehicles (Tech Crunch) $NSANY ( ▲ 4.72% )  

• Senators raise questions about insider trading around Trump tariff announcements (NBC News)

• Fore Rent: Augusta’s $20M Masters Short-Term Home Market (Front Office Sports)

• Why creators are now a boardroom priority (Fast Company)

🎧 Now playing: “Frank Sinatra” - Cake

Tuesday Thursday Saturday is written by Katie Perry, owner of Ursa Major Media, which provides fractional marketing services and strategy in software, tech, consumer products, professional services, and other industries. She is also the co-host of Stocktwits’ Daily Rip Live show.

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Disclaimer: The contents here reflect recaps and summaries of pre-reported or published data, news, and trends. I have cited sources and context for the information provided to the best of my ability. The purpose of the newsletter is to inform and educate on larger trends shaping business and culture — this is NOT investment advice. As an investor, you should always do your own research before making any decisions about your money or your portfolio.