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Startups are a "band of pirates": tech investment leader Garry Tan’s interview with Parker Conrad

Nathaniel BrewsterMar 30, 2022

Garry Tan met Parker Conrad long before he cut Rippling its first check, back when Tan was still a partner at Y Combinator and Conrad had founded his second startup. 

Garry and Parker sat down for a conversation on what it takes to build a successful compound startup, Rippling’s unique approach to customer support, how Parker’s history as a writer for The Harvard Crimson is not unlike those early days bootstrapping a startup—and much more.

It’s inside baseball—or, more accurately, inside-early-stage-high-growth-SaaS-startups. 

Watch the conversation below or on Garry’s YouTube channel here

The highlights:

  • Rippling’s key insight: Employee data is far more distributed across companies than most people realize. Almost every business system a company uses is full of employee information. This data becomes more nuanced and intertwined as a company grows, creating a management headache as well as a business opportunity. 
  • Single-solution startups are saturating the market. It’s becoming clear that deep systems integration and bundled contracting and pricing will begin to dominate the market. Salesforce did this two decades ago and Rippling is doing it now. 
  • Facebook has the social graph. Salesforce has the customer graph. Rippling has the employee graph. These are far more than directories—they are interconnected webs of identities. And that makes them incredibly powerful. 
  • Rippling improved its customer support engagements overnight by looking at the 90th percentile of cases instead of the median. As Parker elaborates, “We discovered the 90th percentile was way worse than the median. I said, ‘The only thing that anyone's allowed to look at is the 90th percentile,’ which is a much more punishing statistic. It basically says, ‘What is the worst 10% of the support interactions that you have?’ We started reporting on that.” 
  • If you want to have great support as a company, you've got to focus relentlessly on the outliers. Editor’s note: Rippling publishes its full, real-time support stats here
  • From early on, Parker was drawn to taking on the incumbents—those with more resources and more power. Reflecting on his time at The Harvard Crimson, he notes, “It felt like we were this band of pirates taking on the administration…I spent a bunch of time after college looking for that experience again and found it in working at startups.”