Real stories. Real people. Real lessons.
Welcome to The Journey : In Conversation—a special series where we sit down with founders, builders, and big thinkers to explore the highs, lows, pivots, and lightbulb moments that define their entrepreneurial or intrapreneurial journey. These unscripted conversations go beyond surface-level success stories. We dig into motivation, failure, resilience, and… execution—so you can absorb lessons by osmosis and apply them to your own journey.
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Prefer watching on YouTube? This podcast episode was filmed live and published on August 14, 2025.
Episode Description
In this episode, Paul interviews John Kennelly, the founder of I Hate Sales, about the journey from uninspired consultant, to revved-up founder, to sales coach for first-time founders. John talks candidly about making every mistake in the book, navigating early failures, and why being honest about what you’re really good at is the key to building momentum. The conversation touches on founder-led sales, overcoming imposter syndrome, learning from failure, and how to validate ideas quickly instead of building in the dark.
Summary of Insights
Why cold outreach is unavoidable—and how to get better at it
The imposter syndrome trap, and how to break out of it
Why naming your offer clearly is half the battle
Validating (or invalidating!) your idea as fast as possible
How to use helping others as fuel for motivation
The power of asking better questions—in business and in life
About the Guest
John Kennelly is a 3x Founder who has seen every peak and valley of the founder journey over the past 14 years. Having been part of successful acquisitions to Google and Apple while also growing a business to $20m ARR and later having to shut it down, he has faced just about every challenge one can face when looking to turn an idea into a fundable, scalable business. John is currently the Founder of I Hate Sales where he helps awesome founders fall in love with sales.
Connect with John Kennelly :
Linkedin : https://www.linkedin.com/in/johnkennellyjr/
Website : https://ihatesales.co
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