The Founder Dating Playbook: Here's the Process I Used to Find My Co-Founder

TL;DR: Gloria Lin, former head of product at Flipboard and first PM at Stripe, spent a year 'dating' six potential co-founders before finding Joel Poloney for Siteline. Her process treats co-founder search with executive-hiring rigor: find candidates through networks and entrepreneurial communities, have initial coffee chats to surface dealbreakers, spend 2 weeks prototyping together, complete a detailed compatibility questionnaire separately, then commit or part ways. The 50-question questionnaire covers six categories: how you operate, roles, corporate structure and funding, personal motivation, team culture, and the co-founder relationship itself. Key topics include equity splits, fundraising philosophy, exit scenarios, and working styles. Lin recommends filling it out independently to avoid groupthink, then spending 6-10 hours discussing answers. The prototyping phase is where most 'breakups' happen - it reveals both idea viability and working compatibility. Lin suggests different approaches for consumer (build crappy MVPs quickly) vs enterprise (focus on customer discovery interviews). The goal is to gather data on collaboration fit while making progress on ideas.