It was another Thursday at Madera—technically “Cougar Night,” but lately the crowd skewed toward Series A founders pretending to be emotionally available. Mr. X and I had arrived early, nursing Negronis while a group at the next table debated whether “romantic compatibility” should be treated as a measurable KPI.
“Have you heard of HeartFund?” asked Brandon, a seed-stage investor whose personal brand revolved around “radical transparency.” He said it like one might mention a new productivity app. “It’s like Robinhood meets Raya.”
Mr. X raised an eyebrow. “Another dating startup?”
“Not quite. Think of it as a personal futures exchange. You invest in someone’s projected earnings—salary, equity, personal brand—basically their Series A potential. If they get promoted, launch a startup, or land an influencer partnership, you get a return. If they stagnate, you can exercise your early-exit clause.”
“Like shorting your ex,” said Lilly, the fashion-tech founder. She was half-joking, but Brandon nodded seriously.
“Exactly. It solves the problem of asymmetrical emotional labor. The app’s built on blockchain—every relationship milestone is tokenized. Breakup settlements happen automatically via smart contract.”
Across the bar, a couple in Patagonia vests clinked glasses. “They’re one of the early pilot users,” Brandon said. “He’s a Stripe PM, she’s a Substack writer. They did a six-month term sheet with mutual equity clauses. If she hits 10,000 subscribers before he gets his next promotion, he owes her 5% of his bonus.”
Mr. X swirled his drink. “So basically love, but fully liquid.”
I asked what happens if one partner… underperforms.
“They have a portfolio review,” Brandon said. “If the algorithm predicts a long-term dip in earning potential—burnout, missed IPO window, brand fatigue—the partner can trigger an ‘early exit.’”
Lilly frowned. “Isn’t that just… breaking up?”
“Not exactly,” Brandon said. “There’s an offboarding process. You can either divest quietly or transfer your equity to a new relationship via rollover credit.”
Mr. X chuckled. “Romance-as-asset-class. Finally something my accountant can understand.”
Brandon grinned, clearly proud. “The tagline is Love, but Optimized. It’s designed to protect emotional investors from sunk cost fallacy.”
He showed us the app—sleek interface, pastel charts plotting “emotional ROI” against “career volatility.” A dashboard displayed your partner’s “growth potential” and “influence index,” both color-coded like stock heat maps.
“People are already building portfolios,” Brandon continued. “Diversifying between stable earners and moonshot creatives. One of our beta users is dating three UX designers and a crypto musician—it’s basically an ETF for intimacy.”
Lilly stared at her drink. “What happens when everyone starts thinking that way?”
Mr. X didn’t look up. “What happens when they don’t?”
By closing time, the conversation had shifted to whether prenups should include vesting schedules. Someone floated the idea of “founder equity in children.” Another suggested tax incentives for polyamorous liquidity pools. Brandon just kept smiling.
On the way out, Mr. X turned to me. “You realize what this means?”
“What?”
“Love finally has a business model.”
He paused, eyes scanning the Tesla lineup outside. “And like every other startup in this town—it’ll probably fail upward.”
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