Repeat Founder Emerges from Stealth and Shares Every Mistake She Made As A First-Time CEO
EP 96 of The Logan Bartlett Show: Untold stories from tech's inner circle
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, including…
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✉️ Episode Memo
Never sign a term sheet too fast
When scaling PlanGrid, Tracy recalls showing up on Sand Hill Road, collecting several term sheets, and signing the one with a heart on it just three days later, as she thought it signaled they cared more. In retrospect, Tracy says “ I shouldn't have signed a term sheet so fast - three days is crazy,” and she recognizes the importance of getting to know the partners who will be on a 10+ year journey with you.
Avoid assholes
Don’t let anyone break your core values. When building PlanGrid, one of the company core values was “no assholes" (amended to “no jerks”), but Tracy ended up keeping a handful of jerks around because of their high performance. By failing to fire them, it signaled to the team that you can get away with anything as long as you perform well, and the team started to believe the other core values could be bullshit too.
When building TigerEye, Tracy solidified their core values before picking the problem they’d solve, optimizing for a healthy productive culture where everyone can speak. With a written contract, there’s no more room for interpretation.
How to fire people with more compassion
Firing someone should rarely be a surprise, as you should previously have a conversation on job expectations and where someone is falling short. Warn the person that if there isn't drastic change, we’ll have to part ways. The upfront conversation leads to a few potential outcomes. Often, the person immediately checks out (due to lack of motivation, trust, belief in themselves, etc.) or actually self-selects out and decides to leave. In ~10% of the case, the conversation is the boost someone needs and you’ll see a full turnaround.
Why job titles actually matter
Tracy and her team proudly managed PlanGrid with a Star Trek-like approach: no job titles, just divisions into operations or engineering. While they saw it as a selling point for recruiting candidates, it actually caused confusion. Tracy soon realized that many of the most ambitious and best people care deeply about their career path. If you want to retain them, you have to care about their titles too.
More details on unique principles Tracy uses to run her company with wholeheartedness in the full episode.
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