Riding the Customer Obsession Wave to Venture Success | Inside Success VP with John Gleeson

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Alone Together: The Story of Solo Venture Capitalists

Sidecut Ventures

12 episodes

5 hours ago

Alone Together reveals the personal journeys of today’s solo General Partners—investors who dare to go it alone. Hosted by Mike Ma, founder of Sidecut Ventures, each episode dives into the triumphs, challenges, and camaraderie that shape these emerging one-person firms. Far from lone wolves, solo GPs are forging a dynamic community—driving innovation for founders, limited partners, and other venture investors. Tune in to discover how these independent fund managers are reshaping the venture ecosystem—and why going solo doesn’t mean going it alone.

Investing

Business

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All content for Alone Together: The Story of Solo Venture Capitalists is the property of Sidecut Ventures and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

Investing

Business

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Riding the Customer Obsession Wave to Venture Success | Inside Success VP with John Gleeson | Alone Together Ep. 9

Alone Together: The Story of Solo Venture Capitalists

58 minutes 52 seconds

5 months ago

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