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Weekly Roundup 10/09/26 (Going Bunker Mode, classical ECC breaks, AI's math discoveries) artwork

Weekly Roundup 10/09/26 (Going Bunker Mode, classical ECC breaks, AI's math discoveries)

On The Brink with Castle Island

October 9, 2026

Matt and Nic are back with more deals and news. In this episode: Is it appropriate to have AI manage your fantasy league? Quant firms are hiring "quals" Justin Drake scares everyone in crypto Did AI destroy math?

Speakers Matt Walsh, Nic Carter

TopicsInvestingBusinessTechnology

SPEAKER_1 (0:01)

Matt Walsh and Nic Carter are partners at Castle Island Ventures. All of these expressed by them or the guests on this podcast are solely their opinions and do not reflect the opinions of Castle Island Ventures. Guests and hosts may maintain positions in the assets discussed in this podcast. You should not treat any opinion expressed by anyone on this podcast as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of their personal opinion. This podcast is for informational purposes only.

SPEAKER_2 (0:22)

Brought down by Bad Mortgage Investments, Lehman, which has 25,000 employees, will be liquidated.

SPEAKER_3 (0:28)

Federal government loans American International Group, AIG, $85 billion. This is a different kind of market and the Fed is asleep.

SPEAKER_4 (0:35)

The federal government is stepping in to stabilize Fannie Mae and Freddie Mac, the two mortgage giants that have been threatened by the housing crisis.

Matt Walsh (0:42)

The Bank of England has pumped $75 billion more into Britain's ailing economy with a new round of quantitative easing.

SPEAKER_1 (0:47)

You print a couple trillion dollars and all of a sudden people start to worry. So out of this worry, we have something called the Bitcoin.

Matt Walsh (0:54)

Welcome to On The Brink, I'm Matt Walsh.

Nic Carter (0:56)

And I'm Nic Carter.

Matt Walsh (0:57)

And the AI people are really mad at you. I guess the anti AI people are really mad at you. Something about, are you automating your fantasy football league? Yeah, people are coming out of the woodwork and saying, how is Nic actually automating his fantasy football?

Nic Carter (1:12)

They really didn't like that.

Matt Walsh (1:14)

The spirit.

Nic Carter (1:14)

They didn't like that. To be clear, all of my co league mates are aware of this. I told them from the start, that's what I was going to do, because I'm not, as you know, from listening to me talk on this podcast, I don't know anything about football.

I don't have time to check waivers and keep track of hundreds of different guys. I can barely remember the name of my own team's starting quarterback.

Matt Walsh (1:38)

Well, it's Drake May, you just told me, right?

Nic Carter (1:40)

Yeah, it's Drake May. So both of my leagues are automated, fully automated, by the way. I don't have to do anything ever. The AI handles everything. I think people don't know how good AI is now.

Matt Walsh (1:49)

Do you screenshot or do you have some sort of a more elaborate integration?

Nic Carter (1:52)

I have Codex with standing instructions to periodically open browser instances of the leagues and then click around because they don't really have API access. So Codex just opens the browser.

So it's much more automated than just taking screenshots. And yeah, people are like, well, why would you automate your hobby? That's against the point of the hobby. It's not my hobby. I don't like playing fantasy.

Matt Walsh (2:17)

You just do it out of you feel like you need to.

Nic Carter (2:19)

It's a social obligation.

Matt Walsh (2:21)

Yeah.

Nic Carter (2:22)

So I think everybody wins, you know, I get more into it because now I have a semi functioning team thanks to AI.

I don't have to worry about if someone broke his rib or has a sprained toenail or whatever. And I can spend all my time doing banter with the rest of the league.

Matt Walsh (2:39)

All right.

I don't hate it. I will say I think I'm outperforming you doing it conventionally. So I'm not convinced that the AI can do a better job than a human at this task.

Nic Carter (2:49)

As of right now, the results are dismal, I would say. So I think across my two leagues, my collective record is one in seven.

Matt Walsh (2:56)

That would support the idea of not doing this.

Nic Carter (2:58)

It's not a strong start, but I think over time the AI advantage will compound as we get into the season. And I think I'm going to make the playoffs in both leagues.

Matt Walsh (3:07)

Do you know the name Bill James at all?

Nic Carter (3:10)

No.

Matt Walsh (3:10)

So Bill James was this guy in the 70s and 80s that was pretty dialed into just data for baseball.

And he wrote these big books that I used to get as a kid just with baseball stats and interesting tidbits and eventually he got hired by the Boston Red Sox. And this was pre-Moneyball as Moneyball started to become a thing. So I wonder if AI is going to have a big impact on just the front office and how people put together teams for these leagues.

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