A Deceptively Simple Healthcare Puzzle (Image Credits: Pixabay)
Phoebe Gates recently disclosed a distinctive question she directs at every job applicant for her AI startup Phia during an appearance on the Opening Bid Unfiltered podcast.
A Deceptively Simple Healthcare Puzzle
Prospective hires at Phia face an immediate test: estimate California’s state healthcare spending and outline a bottoms-up calculation to support the figure.
Gates borrowed the query from another founder and deploys it universally, regardless of the position. She posed it to sales prospects, marketing specialists, and engineers alike. The goal extends beyond factual recall. Instead, it reveals a candidate’s methodical reasoning process under uncertainty. Gates explained this approach during her conversation with Yahoo Finance executive editor Brian Sozzi on the podcast.
Why Logic Trumps Trivia in Hiring
Gates emphasized that no one needs the precise answer memorized. The exercise spotlights structured thinking and adaptability. Such curveballs have long appealed to tech leaders seeking standout talent amid fierce competition. Researchers, however, have debated their effectiveness compared to standardized evaluations.
Phia cofounder Sophia Kianni, Gates’ former Stanford roommate, helped launch the AI shopping agent in April 2025. The company secured a $35 million Series A round soon after. User numbers surpassed 1 million, while revenue expanded elevenfold. Valuation now stands near $185 million, as detailed in a recent Inc. profile.
Tech Titans’ Favorite Brain-Teasers
Gates joins a lineage of founders favoring unconventional probes. Microsoft interviewers once queried why manhole covers are round. Elon Musk posed a riddle: walk one mile south, one mile west, one mile north, and return to the start – where are you?
- The North Pole solves Musk’s puzzle, testing spatial logic.
- Manhole covers’ round shape prevents them from falling through, per Microsoft lore.
- Gates adds a sales-specific twist: recount the wildest action taken to seal a deal, gauging grit and commitment.
These tactics persist as entry-level opportunities dwindle and AI reshapes roles.
Family Wisdom Shapes Her Approach
Gates rejected funding from her parents, Bill Gates and Melinda French Gates, to prove her venture’s merit. She carries a “chip on her shoulder” about independence. Yet she absorbed key entrepreneurial insights from her father.
“From my dad, I’ve really learned that your team is the core of what you’re building,” Gates stated. “You can’t do anything without an incredible team.” This philosophy underpins Phia’s expansion and her rigorous hiring.
Key Takeaways
- Gates’ healthcare question evaluates reasoning for all roles, not rote knowledge.
- Phia achieved $185 million valuation through rapid user growth and revenue gains.
- Team-building remains paramount, echoing Bill Gates’ advice amid family-backed independence.
Phoebe Gates’ method underscores a timeless hiring truth: raw problem-solving often outshines polished resumes in high-stakes startups. What interview question would you pose to top talent? Share your thoughts in the comments.