In this engaging conversation, Scott Kelly shares lessons from more than 30 years working on both sides of the startup world as an entrepreneur and as an investor.

As CEO of Black Dog Venture Partners and founder of VC Fast Pitch, Scott has helped raise billions for early-stage companies while supporting founders through the realities of growth, failure, and scale.

Scott speaks candidly about why most startups fail, the grind of entrepreneurship, and why resilience and execution matter more than ideas alone. He highlights sales as a “lost art” in today’s digital world and explains why strong relationships remain the foundation of sustainable business success.

The conversation also explores the evolving role of technology and AI in entrepreneurship. Scott shares how AI is transforming industries while emphasizing that human connection, humility, and solving real problems must remain central.

He reflects on legacy, balance, and redefining success beyond financial metrics, encouraging founders to build businesses and lives that feel meaningful as well as successful.

• Entrepreneurship is a long game that requires resilience
• Around 90% of startups fail in their early years
• Sales and relationship-building are still critical skills
• Execution matters more than ideas alone
• AI is a powerful tool, but human connection still wins
• Investors back people, not just products
• Strong teams are essential for scaling innovation
• Success takes many forms, beyond money

“Running a startup is just a grind.”
“Sales is a lost art.”
“Success takes many forms.”

00:00 Scott’s Journey from Founder to Investor
01:12 The Reality of Startup Failure
03:58 Why Sales Still Matters
09:44 Relationships as a Growth Strategy
11:38 Venture Capital Realities
15:05 Investment Returns & Risk
19:26 AI’s Impact on Entrepreneurship
24:50 Helping Startups Scale
30:18 Building, Exiting & Starting Again
35:10 Technology vs Human Roles
44:34 Defining Success Beyond Business
56:19 Legacy & Paying It Forward

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If you’re ready to reconnect with what matters most and move forward with clarity, confidence, and purpose, I’d love to support you.

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