Not That Good of a Mom: May Habib on Kids, VCs and Grit
Key points
Key takeaways from Upstarts Media interview with Writer CEO May Habib (September 2026):
Kids versus billionaire status. Habib recalls that a Sequoia rejection during her Series A included a line praising how inspiring it was that she had two young children at home while pitching — a framing she finds disappointing; everyone expects founders to claim nothing matters more than being a billionaire, whereas her kids genuinely matter more.
Who will you back? Asked whether a VC writing only two or three cheques a year would back a founder with kids or one who lives at the office, Habib argues having a family is not innately anti-capitalist,and hopes a standout founder gets backed regardless of circumstance.
Gender and founder–VC relationships. Habib says she has never done anything social or personal with a male VC over her whole career — while she has spent time at women VCs homes and boats — because male VCs feel far more uncomfortable bringing a woman founder into their life across a decade-long relationship.
Brutal working hours. Habib has always worked 15–16 hours a day, even before startups,and currently works 80–90 hours a week every week, saying she does not know anyone in AI who does not work insane hours.
The good mom posture. When investors ask about her children, her instinct is to reassure them that her in-laws take care of them and that she is not that good of a mom — a posture she finds sad, though she credits the team extreme effort with getting Writer where it is today.
Room to grow. Habib says Writer is just getting started and not anywhere near where the team wants its terminal valuation to be, pointing to a massive future ahead.
Harder as a woman. Asked whether her success might make it easier for the next generation of women founders, Habib hopes so but says there is no question it remains much harder to do it as a woman.
Read more: YouTube · Upstarts Media
