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Riding the Customer Obsession Wave to Venture Success | Inside Success VP with John Gleeson | Alone Together Ep. 9
What happens when a snowboarding VC does a podcast with a surfing VC?
I don’t have a good punchline, but it sure was an amazing conversation.
I’ve admired John Gleeson, founder of Success VP, for a long while. He has taken an overlooked part of the ecosystem—founder-led customer success—and turned it into a powerful competitive edge. Just as I am obsessed with coaching, John is dedicated to empowering customer-obsessed founders. Customer success, according to John, isn't merely a department; it's a foundational mindset essential for deeply understanding markets, products, and founders themselves.
Throughout this episode, John and I explore:
How the rhythm and intuition required in surfing mirror the unpredictability of markets and startups.
Why genuine empathy and obsessive attention to customer needs must be driven directly by founders.
The vulnerability and self-awareness required to pivot gracefully, whether on a board or in business.
His insights on building a solo GP fund anchored firmly in relentless customer focus and authenticity.
John openly shares his unconventional journey, embracing risks and uncertainty as opportunities for growth—like when he chose to drop out of business school to chase waves around the world. Like surfing, venture demands courage, intuition, and the humility to accept when you've misread a wave.
This isn't just a conversation about surfing and customer success—it's about how we navigate life's unpredictability with resilience, humility, and curiosity.
I hope you listen with an open heart and an adventurous spirit.
Chapters
00:00 Introduction to John Gleeson and His Journey
02:53 The Impact of Surfing on Business Philosophy
05:53 The Lean Startup Methodology and Its Influence
08:48 Understanding Market Positioning and Product-Market Fit
11:52 The Importance of Founder-Led Customer Success
14:48 Navigating the AI Technology Shift
17:48 Assessing Founders: The Diligence Process
21:03 The Artisan vs. Algorithmic Approach in Venture Capital
33:20 Hiring for Greatness: Insights from Experience
35:36 The Journey to Becoming a Solo GP
39:04 Finding Your Value Proposition in Venture Capital
44:15 Resilience and the Highlight Reel: Keys to Success
48:18 Language Market Fit: Navigating the VC Landscape
49:51 Celebrating Wins: The Best Days as an Investor
53:21 Lessons from Rejection: The Worst Days in VC
57:49 Legacy and Family: How to Be Remembered
View all episodes
By Sidecut VenturesWhat happens when a snowboarding VC does a podcast with a surfing VC?
I don’t have a good punchline, but it sure was an amazing conversation.
I’ve admired John Gleeson, founder of Success VP, for a long while. He has taken an overlooked part of the ecosystem—founder-led customer success—and turned it into a powerful competitive edge. Just as I am obsessed with coaching, John is dedicated to empowering customer-obsessed founders. Customer success, according to John, isn't merely a department; it's a foundational mindset essential for deeply understanding markets, products, and founders themselves.
Throughout this episode, John and I explore:
How the rhythm and intuition required in surfing mirror the unpredictability of markets and startups.
Why genuine empathy and obsessive attention to customer needs must be driven directly by founders.
The vulnerability and self-awareness required to pivot gracefully, whether on a board or in business.
His insights on building a solo GP fund anchored firmly in relentless customer focus and authenticity.
John openly shares his unconventional journey, embracing risks and uncertainty as opportunities for growth—like when he chose to drop out of business school to chase waves around the world. Like surfing, venture demands courage, intuition, and the humility to accept when you've misread a wave.
This isn't just a conversation about surfing and customer success—it's about how we navigate life's unpredictability with resilience, humility, and curiosity.
I hope you listen with an open heart and an adventurous spirit.
Chapters
00:00 Introduction to John Gleeson and His Journey
02:53 The Impact of Surfing on Business Philosophy
05:53 The Lean Startup Methodology and Its Influence
08:48 Understanding Market Positioning and Product-Market Fit
11:52 The Importance of Founder-Led Customer Success
14:48 Navigating the AI Technology Shift
17:48 Assessing Founders: The Diligence Process
21:03 The Artisan vs. Algorithmic Approach in Venture Capital
33:20 Hiring for Greatness: Insights from Experience
35:36 The Journey to Becoming a Solo GP
39:04 Finding Your Value Proposition in Venture Capital
44:15 Resilience and the Highlight Reel: Keys to Success
48:18 Language Market Fit: Navigating the VC Landscape
49:51 Celebrating Wins: The Best Days as an Investor
53:21 Lessons from Rejection: The Worst Days in VC
57:49 Legacy and Family: How to Be Remembered