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20VC: Segment Founder Peter Reinhardt on His Learning Process, How Great Leaders Listen and Encourage Debate within Their Organisation & How To Use Data Intelligently To Improve Decision-Making

Apr 22, 2021

Peter Reinhardt, Founder and CEO of Segment, shares his remarkable journey from skepticism to success, with Segment's $3.2 billion acquisition by Twilio. He emphasizes the importance of data in learning frameworks and how many falter in constructing theirs. Reinhardt also discusses the art of active listening in leadership, revealing how to create a safe environment for debate. Additionally, he explores the balance between thoughtful discussion and decisive action, along with insights on problem-solving and fostering adaptability within organizations.

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ANECDOTE

Segment's Unintentional Success

Peter Reinhardt tried to "kill" his co-founder's idea for Segment, an open-source library.
By testing it rigorously, he unintentionally proved its value, leading to its success.

INSIGHT

The Airbnb Myth

The Airbnb story of persistence without initial product-market fit can be misleading.
Founders should prioritize understanding market needs over clinging to their vision.

ADVICE

Depth-First Learning

Go deep in learning, focusing on a narrow area of interest.
Explore specific details to gain a more nuanced understanding than most.

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Peter Reinhardt is the Founder and CEO @ Segment, the leading customer data platform with over 20,000 companies using Segment to collect, clean, and control their customer data. Prior to their $3.2BN acquisition by Twilio in 2020, Peter raised over $283M for Segment from Accel, Thrive, Meritech, GV, General Catalyst and Kleiner Perkins to name a few. Peter is also an active angel investor having made investments in the likes of Retool, Newfront, Pilot and more.

In Today’s Episode with Peter Reinhardt You Will Learn:

1.) How Peter made his way into the world of startups and how he came to found a company, Segment, by actively trying to prove to his co-founder that it would not work? Why does Peter believe the Airbnb story is the most destructive myth for founders to follow?

2.) Learning: How does Peter think about learning frameworks for new topics? How does he construct his? How does Peter use data within this learning process to increase his rate of learning? Where do the majority of people go wrong in constructing their framework for learning?

3.) Listening and Debate: What does Peter believe is required to be "a good listener"? What questions do the best listeners ask? What tone do they use to ask these questions? How does Peter create an environment of safety internally where people feel they can debate? How does one balance between debate and thinking vs putting those thoughts into action?

4.) Problem-solving: How does Peter breakdown problems into their component parts? Through what mechanism does he determine what to prioritise first? How would Peter describe his decision-making process? How does he determine between head vs heart in decisions? In what way does Peter use data to further inform the decisions he makes?

5.) How would Peter describe his management style today? Has it changed over time? In what way has working with a coach changed the way Peter thinks about leadership? What elements do they focus on? How often does he see his coach? What have been some of his biggest takeaways?

Item’s Mentioned In Today’s Episode with Peter Reinhardt

Peter’s Favourite Book: The Chalice and the Blade, Crucial Conversations

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