Tracy Young, co-founder of PlanGrid, shares how her background in construction led to building one of the most successful startups in the space—culminating in an $875M acquisition by Autodesk. She dives into lessons learned on product-market fit, go-to-market strategy, and navigating founder relationships as the company scaled. Tracy also reflects on her time at Y Combinator, the fundraising process, and the emotional challenges of selling a company. Post-acquisition, she transitioned into coaching before founding her new startup, TigerEye. She discusses how AI, core values, and leadership growth are shaping this next chapter—and what she wishes more founders knew about resilience and reinvention.