The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving

566: Silicon Valley’s CEO Whisperer on Why Most Startup Founders Fail (with Rich Hagberg)

Jul 7, 2025

Rich Hagberg, known as Silicon Valley’s CEO Whisperer, has advised over 1,000 founders. He discusses why most startups fail, highlighting that many founders excel in vision but struggle with execution and relationship-building. Stress and impulsivity hamper decision-making and team trust. Hagberg stresses adaptability as crucial for success and advocates for developing specific behaviors like delegation and feedback seeking. He emphasizes the importance of self-awareness and meditation in navigating entrepreneurship challenges.

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INSIGHT

Founders Are Visionary but Poor Executors

Founders are typically visionary evangelists with high creativity but low execution skills.
Successful founders manage relationship building better and implement average execution systems, unlike unsuccessful ones.

INSIGHT

Why Most Founders Fail and How to Actually Succeed

Rich Hagberg reveals that most startup founders are "visionary evangelists"—high on vision but generally poor at execution. This is a key reason why many founders fail: they resist structure, delay essential hires, and struggle to implement their ideas effectively as their companies grow.

Successful founders tend to be average at relationship-building and slightly better at execution, while unsuccessful ones score low in both. Hagberg advises founders to focus on a few specific behaviors they can realistically improve, such as delegation, feedback seeking, and stress management.

He emphasizes the need to transition from being a doer to a facilitator, hiring complementary team members who excel at relationship-building and execution, and developing adaptability as a critical leadership skill. Openness to feedback and self-awareness are often more predictive of success than charisma or IQ.

ADVICE

Delegate and Seek Feedback

Founders should delegate, empower, and learn to work through others to scale their impact.
They must seek feedback, ask disconfirming questions, and run disciplined decision processes.

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Rich Hagberg, often referred to as “Silicon Valley’s CEO Whisperer, psychologist and co-author of Founders Keepers, has advised over 1,000 executives and founders. In this conversation, he outlines why most startup leaders fail, and what the data reveals about those who succeed. Some key insights include:

“Founders, overwhelmingly, are visionary evangelists… but they’re not particularly good at execution.” Hagberg’s research shows that unsuccessful founders often score low on execution and relationship-building. They resist structure, delay key hires, and react impulsively under stress.

“You can change your behavior to some degree, but it’s very hard to change your fundamental personality.” Hagberg encourages founders to identify three to four behaviors they can realistically improve, such as delegation, feedback seeking, and stress management.

“You need to go from being a doer to a facilitator of doing.” Scalable leadership requires building teams that complement the founder’s own gaps and letting go of tasks that dilute impact.

“Startups are almost a Darwinian survival of the fittest… the unsuccessful ones are more impulsive and reactive.” Stress and poor self-regulation directly impact team trust and decision quality. Founders who succeed tend to manage energy deliberately and maintain self-awareness.

“If we had to zero in on one thing that is the biggest differentiator, it’s adaptability. You never have permanent product-market fit.” Hagberg shares why openness to feedback and reflection is often more predictive of long-term success than IQ or charisma.

“I realized I was creating a culture that reflected my strengths and weaknesses. If I was going to make the company better, I had to grow as a leader.”

This conversation is for founders, investors, and operators who want to understand the behavioral patterns that quietly shape success or failure in startups. It delivers clear, evidence-based insights into what it takes to lead effectively as complexity scales.

Get Rich’s new book here: https://shorturl.at/YsQcl

Founders, Keepers: Why Founders Are Built to Fail, and What it Takes to Succeed

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