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Podcast Episode

Ampleo Chief Growth Officer Joe Grover - Why Failure Is Every Entrepreneur’s Greatest Teacher

About this episode

Joe Grover, Chief Growth Officer at Ampleo, joins Clint Betts for a conversation on entrepreneurship, AI, leadership, acquisitions, marketing, and the lessons that come from failure.After building businesses, working in venture capital at Mercato Partners, leading marketing teams at venture-backed companies, serving as a turnaround CEO, and helping scale companies like Homie, Joe has spent decades helping businesses grow through both success and adversity.Today, Joe helps lead Ampleo, a firm providing fractional finance, marketing, HR, and executive leadership services to growing businesses. In this episode, he shares how AI is changing professional services, why trusted advisors still matter, and why entrepreneurs learn more from failure than success.The conversation also explores acquisitions, executive decision-making, startup leadership, productivity, and how AI is reshaping knowledge work. In this episode:00:00:00 - Introduction and Joe's Background 00:00:14 - Early Career and Venture Capital Experience 00:00:35 - Turnaround CEO and Homey Experience 00:00:56 - Sabbatical and Joining Amplio 00:01:17 - Amplio's History and Services 00:01:55 - Impact of AI on Business 00:02:11 - AI in Board Meetings and Strategy 00:02:42 - AI Adoption in Small to Mid-Sized Businesses 00:03:04 - Early Adoption of ChatGPT and Custom GPTs 00:03:47 - AI in Professional Services 00:04:50 - M&A Strategy and AI Integration 00:05:11 - Value of Executive Experience vs. AI 00:06:04 - Identifying AI-Disruptable Verticals 00:07:10 - Preference for Claude and Co-Work Over ChatGPT 00:07:39 - Use of Various AI Tools for Content Creation 00:08:54 - Automating Daily Work Life with AI 00:09:47 - Typical Workday Routine 00:10:20 - Use of ClickUp and AI for Team Management 00:11:54 - Reducing the Need for Meetings 00:12:32 - Integration of Various SaaS Products 00:13:04 - Future of SaaS and AI Integration 00:14:56 - SaaS Market Trends and HubSpot's Position 00:16:11 - Uncertainty in SaaS Platforms' Long-Term Position 00:17:15 - Technology Adoption in SMBs 00:18:08 - HubSpot's Market Penetration 00:19:12 - Leadership Philosophy 00:22:08 - Recommended Reading 00:25:29 - Common Marketing Mistakes 00:27:19 - Effectiveness of Billboards and Owned Media 00:29:09 - Owned, Earned, and Paid Media Strategies 00:31:02 - Experience with Homey and Billboards 00:31:27 - Launching a Podcast on Failure 00:34:55 - Mental Health and Entrepreneurship 00:36:04 - The Fail Club Concept 00:36:46 - Final Question: Who Gave You a Chance? 00:39:02 - Junto Program and Early Entrepreneurship 00:40:13 - Equity and Investment in Junto Program 00:40:44 - Closing Remarks and GratitudeIf you're interested in entrepreneurship, leadership, venture capital, AI, business growth, marketing, or executive decision-making, this conversation is packed with practical insights and hard-earned lessons.Subscribe for more conversations with founders, CEOs, and leaders shaping the future of business and technology.