Dad Starts $30M AI Startup Mid-Tantrum, Masters Seasons and Sanity

KEY POINTS

•Aaron Cannon co-founded Outset during his paternity leave, balancing newborn care with startup grind in San Francisco.
•Outset secured $30 million in Series B funding in December and is backed by the accelerator Y Combinator.
•Despite intense workdays and nightly parenting duties, Aaron prioritizes being present for his 3-year-old son's early childhood development.

In the frenetic heart of San Francisco, 37-year-old Aaron Cannon launched his AI startup Outset while entrenched in paternity leave with his 3-year-old, blending diapers and deal-making since 2023. Outset snagged a hefty $30 million in Series B funding last December, all while Aaron juggles explaining 'seasons' to a kid who doesn't yet grasp 'years.' Backed by Y Combinator — where, fun fact, Aaron felt like the 'grandpa' among twenty-somethings on Wednesday Night Speaker Series — his daily schedule is an adrenaline-fueled tightrope: intense work calls, preschool pickups, negotiating contracts, bedtime routines, then powering back to emails. Aaron admits, 'Everything gets deprioritized except family and work,' which roughly translates to living a chaotic myth of work-life balance. His cofounder has different hours, which at least means someone’s not explaining quantum AI to a cranky toddler at 5 pm. Overall, it's a murderer's row of 'intense' days punctuated by existential toddler questions and ruthless prioritization. Parenting and startups: both wildly oversubscribed, high-stress gigs starring a guy named Aaron Cannon.