After Selling Company for $875M, Repeat Founder Emerges from Stealth & Shares Every Mistake She Made

This week, Tracy Young launched her second startup, TigerEye, from stealth mode. After selling PlanGrid to Autodesk for $875 million and working with YC for a couple of years, Tracy and her husband/co-founder decided to build the software they wished they’d had while building PlanGrid. In our conversation, Tracy unmasks her vision for TigerEye and shares everything she learned as a first time CEO that she’s bringing into her second company. (00:00) Intro (01:39) The Shift in Market Dynamics and PlanGrid's Response (07:07) The Importance of Addressing Multiple Stakeholders in Product Development (09:08) From PlanGrid to TigerEye: Tracy Young's New Venture (11:39) The Significance of Organizational Structure and Team Dynamics (15:03) The Evolution of Sales Strategy and Team Structure (17:28) The Decision to Sell PlanGrid and Its Aftermath (24:17) The Genesis of TigerEye and Its Mission (31:09) Cultivating a Purposeful Company Culture at TigerEye (39:29) Recruitment Strategies and the Value of Reference Calls (45:42) Product Development Insights and Market Focus (49:39) The Importance of Customer Tracking for Startups (49:57) The Challenges of Scaling with CRM and ERP Systems (51:55) Navigating the Tough Decisions of Firing Employees (57:08) The Journey from Construction Engineering to Tech Entrepreneurship (57:42) The Birth and Growth of PlanGrid (01:01:24) Navigating Personal and Professional Growth (01:05:50) The Emotional Journey of Losing a Co-Founder (01:17:34) From Stealth Mode to Market Impact with Tiger Eye (01:18:31) Embracing Remote Work and Building a Diverse Team (01:30:15) Reflections on Fundraising and Board Meetings (01:34:28) Finding Work-Life Balance in Startup Culture Produced: Rashad Assir & Leah Clapper Mixed and edited: Justin Hrabovsky Executive Producer: Josh Machiz Check out Unsupervised Learning, Redpoint's AI Podcast:    / @redpointai   🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast... Spotify: https://open.spotify.com/show/5WqBqDb... Google Podcasts: https://podcasts.google.com/feed/aHR0... 🎥 Subscribe on YouTube:    / @theloganbartlettshow   Follow on Socials 📸 Instagram -   / theloganbartlettshow   🐦 Twitter -   / loganbartshow   🎬 Clips on TikTok -   / theloganbartlettshow   About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.