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

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 Background00:00:14 - Early Career and Venture Capital Experience00:00:35 - Turnaround CEO and Homey Experience00:00:56 - Sabbatical and Joining Amplio00:01:17 - Amplio's History and Services00:01:55 - Impact of AI on Business00:02:11 - AI in Board Meetings and Strategy00:02:42 - AI Adoption in Small to Mid-Sized Businesses00:03:04 - Early Adoption of ChatGPT and Custom GPTs00:03:47 - AI in Professional Services00:04:50 - M&A Strategy and AI Integration00:05:11 - Value of Executive Experience vs. AI00:06:04 - Identifying AI-Disruptable Verticals00:07:10 - Preference for Claude and Co-Work Over ChatGPT00:07:39 - Use of Various AI Tools for Content Creation00:08:54 - Automating Daily Work Life with AI00:09:47 - Typical Workday Routine00:10:20 - Use of ClickUp and AI for Team Management00:11:54 - Reducing the Need for Meetings00:12:32 - Integration of Various SaaS Products00:13:04 - Future of SaaS and AI Integration00:14:56 - SaaS Market Trends and HubSpot's Position00:16:11 - Uncertainty in SaaS Platforms' Long-Term Position00:17:15 - Technology Adoption in SMBs00:18:08 - HubSpot's Market Penetration00:19:12 - Leadership Philosophy00:22:08 - Recommended Reading00:25:29 - Common Marketing Mistakes00:27:19 - Effectiveness of Billboards and Owned Media00:29:09 - Owned, Earned, and Paid Media Strategies00:31:02 - Experience with Homey and Billboards00:31:27 - Launching a Podcast on Failure00:34:55 - Mental Health and Entrepreneurship00:36:04 - The Fail Club Concept00:36:46 - Final Question: Who Gave You a Chance?00:39:02 - Junto Program and Early Entrepreneurship00:40:13 - Equity and Investment in Junto Program00:40:44 - 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.