Keys to a Successful Pivot | 2min snip from Lenny's Podcast: Product | Growth

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Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)

Lenny's Podcast: Product | Growth | Career

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Keys to a Successful Pivot

A key aspect of a successful pivot is building upon what you already know and have experience in rather than venturing into unfamiliar territory. Pivoting towards a warmer direction, where you have expertise and knowledge, tends to yield positive results. It is crucial to leverage your existing skills and background to pivot effectively. Overcoming mental barriers and biases against working on ideas you are familiar with is essential for a successful pivot.

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Dalton Caldwell is Managing Director and Group Partner at Y Combinator. Prior to YC, he was the co-founder and CEO of imeem (acquired by MySpace in 2009) and the co-founder and CEO of App.net. During his time at YC, he’s advised more than 35 YC unicorns, including DoorDash, Amplitude, Webflow, and Retool, and has worked across 21 different YC batches. He’s also racked up more than 6,500 office hours with founders. In our conversation, we discuss:

• Why founders need to adopt the mindset “Just don’t die”

• The most common reason startups fail

• When to pivot, and characteristics of a good pivot

• The concept of “tar pit ideas” and examples of bad startup ideas

• Why investors say no to startups

• The importance of market size in investment decisions

• The pitfalls of founders over-delegating

• Effective ways to talk to customers

• 20 ideas Dalton is looking to fund

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