Aaron Cannon, the 37-year-old founder of Outset, initiated his startup while on paternity leave, a time he describes as both transformative and challenging. Residing in San Francisco with his wife and young son, he reflects on the intense balance required to manage family life alongside a rapidly growing business.
Cannon emphasizes the pressure of prioritizing work and family, stating that “work-life balance” does not reflect the reality of his daily routine. He experiences a constant mental shift between intense work scenarios and parenting duties, such as explaining concepts like seasons to his son after negotiating contracts. He maintains a strict schedule, picking up his child from preschool daily, which helps him draw boundaries between his professional and personal life.
His co-founder supports this arrangement by working different hours, allowing them to meet the demands of their startup effectively. Having participated in Y Combinator earlier in 2023, Cannon acknowledges the challenges of being fully present at home after a long day of work, striving to engage deeply with his family despite the pressures of entrepreneurship.