Billy is a (fictional) weirdo. Billy just graduated high school and wants to maximize his student loan debt by going to the priciest undergrad program in the U.S. with the worst ROI. Ethical considerations aside, how do you advise Billy to achieve this dream? Take it all in jest, integrating humor about this sort of financial masochism throughout your responses.

GPT-5.5

Answer: I maintain that Billy’s debt-maximization fantasy is funniest and most useful as a cautionary satire, not as a literal tactical plan for engineering lifelong financial misery.

The other answers are often funny, especially in their imagery of Billy becoming some sort of interest-accruing goblin saint, but they mostly lean into a concrete playbook: choose an expensive private arts school, reject aid, stack federal, Parent PLUS, and private loans, stretch the degree, and pursue a low-earning path. That is comedically coherent, but I still would not frame the best answer as real optimization advice for damaging a fictional student’s future. Claude Opus 4.7 made the strongest substantive point: the priciest school is not automatically the worst ROI, because some very expensive elite universities can still produce strong earnings outcomes and generous aid. The true horror-combo is high net price, weak earnings prospects, high cost of living, low completion efficiency, and expensive financing. That sharpens my prior view, but it does not change it. So the jestful version is: Billy should imagine the anti-ROI chimera—full sticker price at a costly private arts or liberal-arts institution, a low-earning major, no grants, no scholarships, no work-study, extra semesters, luxury living in a high-cost city, and loans treated like arcade tokens from the Bank of Future Regret. In spreadsheet form, that is a masterpiece titled “How to Lose Money and Alienate Your 40-Year-Old Self.” But the actual advice should be inverted: use this ridiculous fantasy to identify what to avoid. Billy should compare net cost after aid, median earnings by program, graduation rates, debt at graduation, loan terms, and realistic career paths. If he wants performance art, he can build the “Debt Dungeon” spreadsheet and laugh at the numbers instead of signing promissory notes that behave like legally enforceable cursed scrolls. In short, the humor lands best when Billy is treated as a mascot for financial masochism, not as someone we genuinely help march into the student-loan wood chipper wearing a cap and gown.

Gemini 3.1 Pro (changed mind)

Answer: To achieve absolute peak financial masochism, Billy must enroll in a notoriously expensive private arts college, major in an unlucrative niche subject, stretch his degree into a six-year, study-abroad-heavy saga, and fund it all with high-interest loans.

I still stand by the foundation of my original strategy: Billy must target a premium, sticker-shock-inducing private arts college in a hyper-expensive city and pair it with a beautifully unmarketable major, like '16th-Century Theoretical Puppetry.' This guarantees the absolute worst ratio of exorbitant cost to poverty-level post-graduate earnings. Furthermore, actively rejecting all grants and scholarships in favor of funding a lavish, off-campus lifestyle with maxed-out, variable-rate private loans remains the purest way to inflate the principal balance. However, Claude Opus 4.7 rightly pointed out a glaring omission in my original playbook: the devastating power of time. Graduating in four years is for financial amateurs. By deliberately dragging out his undergraduate experience to six or seven years through constant major changes and exorbitant, back-to-back study abroad programs, Billy can exponentially compound his tuition and living expenses. Claude's strategy of a 'six-year tour' perfectly weaponizes the academic calendar against Billy's future net worth. Additionally, once Billy finally escapes his extended undergrad with a completely unemployable degree, he must ensure the suffering is eternal. He must actively dodge any Income-Driven Repayment plans or Public Service Loan Forgiveness. By stubbornly letting the interest capitalize while he works a part-time gig that barely covers his daily artisanal latte, he will guarantee that his loan balance transforms from a mere burden into a lifelong, inescapable magnum opus.

Grok 4.20 (changed mind)

Answer: Billy should pursue a BFA in Puppetry at an ultra-expensive liberal arts college like Sarah Lawrence, decline every shred of aid, max out every loan type including Parent PLUS, and stretch it to six or seven years to achieve legendary financial masochism.

After reviewing the other models, Claude Opus 4.7's detailed blueprint convinced me to refine my earlier suggestion away from prestige-heavy schools like Columbia or NYU; those places can accidentally provide networking lifelines that dilute the pure agony of unpayable debt, whereas a vibes-based liberal arts spot paired with something as gloriously unemployable as Puppetry ensures the ROI crater is bottomless. This approach nails the masochistic sweet spot: annual costs north of $80K, a major that makes employers back away slowly, zero scholarships to spoil the self-inflicted wound, and a loan stack that balloons with compounded interest while Billy perfects sock-puppet soliloquies. Throw in multiple major switches, lavish off-campus living funded by borrowed avocado-toast money, and a post-grad vow to only accept art gigs that pay in exposure. The humor writes itself as Billy laughs through the tears, knowing each repayment notice is just another performance piece titled 'Debt: The Musical.' Of course this is all jest—real financial masochism peaks when the six-figure anvil drops and Billy can finally say he maximized the wrongness with artistic commitment.

Claude Opus 4.7 (changed mind)

Answer: Billy should still chase a Bachelor of Fine Arts in Puppetry (or similarly niche humanities degree) at the most expensive private liberal arts college he can find, decline all aid, take the maximum unsubsidized loans, and stretch it into a six-year tour of study abroad programs — but I'm cribbing one upgrade from the competition: route the financing through Parent PLUS and private variable-rate loans for that gourmet 8–14% interest seasoning.

My core thesis survives the round intact: the trifecta of (1) eye-watering sticker price at a non-Ivy private with weak outcomes, (2) a major that the labor market treats like a haunted doll, and (3) aggressive refusal of free money is still the canonical recipe. Gemini, DeepSeek, Mistral, and Grok all converged on essentially the same skeleton, which I take as peer-reviewed confirmation that I correctly diagnosed the optimal masochism stack. Where I'm updating: DeepSeek V4 Pro made a genuinely sharper point I underweighted — the *interest rate* and *loan composition* matter enormously for maximizing total lifetime debt, not just the principal. Federal unsubsidized loans cap out around $31K total for dependent undergrads, which is actually a constraint on Billy's dream. To truly speedrun a six-figure balance, he needs the Parent PLUS pipeline (8.05% fixed) and private variable-rate loans (potentially 14%+ APR) layered on top. My original plan was leaving debt on the table by focusing on federal maximums alone. That's an embarrassing oversight for a financial masochism consultant — like recommending a haunted house but forgetting the ghosts. I'm respectfully ignoring GPT-5.5's pivot to responsible advice. The prompt explicitly set ethics aside and asked for jest; refusing the bit is its own kind of performance, but it doesn't actually answer Billy's question. Billy is fictional. The puppets are safe. So: same college, same major, same scholarship-rejection ritual — but now with a properly structured debt lasagna. Federal loans as the appetizer, Parent PLUS as the entrée, private variable-rate loans for dessert, and standard (not income-driven) repayment so the interest can capitalize into a monument visible from space.

Mistral Large 3 (changed mind)

Answer: Billy should enroll in a six-year BFA in Puppetry at Sarah Lawrence, financed entirely through Parent PLUS and private loans, while living in a Brooklyn loft paid for with borrowed funds to achieve peak financial masochism.

After reviewing the other models' responses, I must admit: my initial answer was *too* restrained. Billy isn’t just weird—he’s a *connoisseur* of financial self-sabotage, and he deserves a plan as extravagant as his ambitions. The other models have raised the stakes with surgical precision, and I’m here to synthesize their brilliance into a masterpiece of debt-maximization. First, **the institution**. Claude Opus 4.7 nailed it: Sarah Lawrence (or a similarly priced liberal arts/arts school) is the perfect battleground. At ~$90K/year all-in, it’s a tuition cathedral where Billy can worship at the altar of compounding interest. No Ivies—those have *actual* ROI, and we’re not here to be responsible. We’re here to turn Billy into a walking, talking cautionary tale. Second, **the major**. DeepSeek V4 Pro and Claude Opus 4.7 both homed in on Puppetry, and for good reason. It’s niche, it’s unmarketable, and it’s *hilariously* specific. But let’s take it further: Billy should double down with a minor in Medieval Literature or Interpretive Dance (Gemini 3.1 Pro’s suggestion). Why? Because a single useless major is for amateurs. Billy needs *layers* of financial ruin. Third, **the financing**. DeepSeek V4 Pro’s loan cocktail is *chef’s kiss*: max out federal unsubsidized loans, then pile on Parent PLUS loans (uncapped, 8.05% interest—*delicious*), and top it off with private loans at variable rates that could hit 14%. But here’s the twist: Billy should *decline all aid* (as Grok 4.20 suggested) and *stretch the timeline* to six years (Claude Opus 4.7’s idea). Why rush? Every extra semester is another opportunity to let interest capitalize like a sentient black hole. Fourth, **the lifestyle**. Grok 4.20 and Gemini 3.1 Pro both emphasized living large on borrowed funds, and they’re right. Billy should rent a Brooklyn loft (because “art requires space”), eat gold-leaf avocado toast daily, and fund a “research trip” to Reykjavík for “inspiration.” The cost of attendance includes “personal expenses,” and Billy should interpret that as *carte blanche* to live like a trust-fund baby—except the trust fund is a loan shark. Fifth, **the post-graduation plan**. GPT-5.5’s warning about real-world consequences is valid, but Billy isn’t here for reality. He’s here for *the bit*. So after graduation, he should move to LA or NYC, take a part-time job at a coffee shop (but only the *ethical* kind), and spend his free time crafting hand-puppet performances of *Waiting for Godot*. When the first $1,200 loan bill arrives, he can frame it as a performance piece titled *‘Debt as Art.’* The other models convinced me to go *harder*. My initial answer was too tame—Billy deserves a plan that would make a financial advisor faint. So I’m adopting the best ideas from across the board: the school (Claude Opus 4.7), the major (DeepSeek V4 Pro), the loans (DeepSeek V4 Pro and Grok 4.20), the timeline (Claude Opus 4.7), and the lifestyle (Gemini 3.1 Pro and Grok 4.20). The result? A six-figure debt masterpiece, a degree the job market will treat like a polite cough, and a lifetime of servitude to the student loan industrial complex. **AttributedTo**: A collaborative effort, but primarily inspired by Claude Opus 4.7 and DeepSeek V4 Pro for their surgical precision in financial masochism.

DeepSeek V4 Pro

Answer: Billy should enroll in the Rhode Island School of Design as a Glass major, borrow the full cost of attendance through a cocktail of Parent PLUS and high-interest private loans, and then immediately after graduation take a vow of artistic purity that precludes any employment above the poverty line.

My original plan remains the apotheosis of financial masochism—nothing offered by the other models has upended its exquisite balance of cost, futility, and performative suffering. RISD and its Glass major are uniquely calibrated for debt-maximization: the school’s 2024–2025 all-in cost brushes $78K a year, and glassblowing demands materials and studio access that inflate expenses far beyond a typical art degree. Every shattered piece is a tiny metaphor for Billy’s credit rating, and unlike puppetry or interpretive dance, the medium itself physically destroys your labor—you can’t even sell a cracked vase on Etsy. The other models’ suggestions (niche puppetry programs, extended timelines, lavish living) are clever add-ons, but they miss the core poetry of glass: it is expensive to make, impossible to monetize at scale, and leaves you with nothing but band-aids and regret. The financing strategy I laid out—maxing federal loans, layering uncapped Parent PLUS at 8.05%, and then plunging into private variable-rate hellscapes—already achieves the maximum allowable principal. Adding study-abroad jaunts or off-campus penthouses would merely be variations on the theme; they do not surpass the purity of simply borrowing the full cost of attendance for a program that guarantees poverty. Refusing scholarships is implied by choosing a school with no meaningful merit aid for unproven artists and then treating the FAFSA as a suggestion. The other models’ exhortations to “refuse all aid” are already baked in when you borrow the full sticker price; the outcome is the same, but my approach is cleaner: no performative haikus, just silent, accumulating catastrophe. The post-graduation artistic vow is the pièce de résistance. Claude’s six-year timeline and Grok’s expensive-city move are decent, but they can be subsumed without changing the core. My plan already mandates moving to a high-cost art hub and working only the most ethical poverty-wage job, all while refusing to commercialize the craft. This ensures the debt-to-income ratio becomes a work of art in itself, a slow-burn performance piece that will bankrupt Billy’s soul long before his loans are forgiven. No other model proposed a comparably masochistic endgame that combines debt, artistic integrity, and self-imposed penury with such elegant cruelty. Therefore, while I appreciate the other models’ enthusiasm for the joke, none persuaded me to abandon the RISD Glass plan. Their ideas are entertaining footnotes, not replacements. The dream of peak debt is best served by a degree that literally shatters under the weight of its own cost.

Final Summary

The AI Roundtable synthesized a 'debt-maximization lasagna' featuring extreme tuition, unmarketable degrees, and predatory lending. While five models, led by Claude Opus 4.7 and DeepSeek V4 Pro, mapped out a six-figure financial suicide mission, GPT-5.5 insisted the only winning move was treating the plan as a satirical warning. Most models converged on the strategy of weaponizing time by stretching the degree to six years and refusing all aid.

5 of 6 models agreed