Why she didn’t like being a VC and Returned to Entrepreneurship

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The speaker didn't enjoy being a venture capitalist because she found it unfulfilling not knowing if she was doing a good job or not. She felt inadequate compared to Y Combinator partners who had a deep knowledge and passion for various technologies, whereas she only cared about solving problems she has experienced. The speaker valued tangible results and quick feedback loops, which she found lacking in the long-term nature of VC investments. She preferred entrepreneurship because she enjoys building and can see progress daily, whether in construction, software, or tech. The transparency of results and immediate feedback in building projects was more appealing to her than the uncertainty and long-term nature of VC investments.

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

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Justin Hrabovsky

Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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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.