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.
(0:00) Introduction to Tracy Young
(0:04) Tracy Young's background and early career
(2:39) Lessons learned from construction industry
(5:33) Founding of PlanGrid
(8:03) Experience with Y Combinator and early product market fit
(13:18) Sales strategies and early adoption
(18:23) Fundraising advice and managing executive leadership
(22:42) Focus areas and executive relationship red flags as PlanGrid scaled
(25:11) Importance of firing quickly and Tracy stepping down
(26:46) M&A with Autodesk and growth challenges
(31:00) Board's perspective on acquisition and independence
(35:20) Leadership changes and maximizing M&A options
(41:40) Post-acquisition experience and transition to coaching
(44:12) Founding Tiger Eye and establishing core values
(47:36) Balancing work and family with wholeheartedness
(49:01) Adhering to core values during financial stress
(51:10) Future of TigerEye and AI's impact
(52:44) Reflections on leadership growth and redefining success
(55:13) Closing remarks
