Tired of hearing about AI chatbots and ready for the next evolution? In this episode, serial tech entrepreneur Bradley Younge pulls back the curtain on Agentic AI—the future of business automation. Bradley, who helped scale his last company (SkyKick) to over $45 million in ARR, explains why he’s betting his next chapter on building an autonomous AI workforce for small businesses. He shares how his new company, Outermind, is giving entrepreneurs an "unfair advantage" by deploying AI agents directly inside Microsoft 365 to handle operations, sales, and content. This episode is a masterclass in how to stop using AI as a simple tool and start deploying it as a proactive team member that drives real business growth.

💡 What You'll Take Away For YOUR Business

  • The crucial difference between assistive AI (like ChatGPT) and a proactive, autonomous AI workforce that accomplishes goals without constant prompting.
  • How small businesses can leverage their agility to adopt AI agents faster and more effectively than slow-moving, billion-dollar companies.
  • A practical framework for implementing your first "AI Chief of Staff" to oversee business goals, manage tasks, and integrate tools like QuickBooks and HubSpot.
  • Real-world examples of how AI agents can automate weekly reports, manage your sales pipeline from lead to invoice, and free you from mind-numbing administrative work.
  • How to build trust with AI by implementing critical guardrails, controls, and human-in-the-loop oversight so your agents work for you, safely.
  • Why the future of competitive advantage lies not in working harder, but in building a business that intelligently delegates to an AI workforce.

📝 About Bradley Younge

Bradley Younge is the founder and CEO of Outermind, a company building an AI agentic workforce to help small and mid-sized businesses automate their most critical functions. A seasoned technology leader with a history of being at the forefront of innovation, Bradley’s journey includes being the third employee at drugstore.com during the dot-com boom and co-founding Skykick, a SaaS company he helped grow to over $45 million in annual recurring revenue. His deep experience in both the startup and enterprise worlds gives him a unique perspective on how small businesses can leverage cutting-edge technology to compete and win.

🎯 Brad's BEST Piece of Advice for Wantrepreneurs and Entrepreneurs

"Jump on the AI wagon... Don't let this pass you by. You've just got to start using it because it's going to be the way the business world is working in the near future. So don't let it pass you by and don't get behind."

📢 Memorable Quotes

  • “Small businesses, if they could be given the right tools… could move a lot, lot faster and hopefully start really taking it to the enterprise and competing with them.” – Bradley Younge
  • “We can move so fast and we can get such high-quality stuff done by using AI in the proper mechanism... it's really exciting to be able to try to take that out to the small businesses and give them kind of an unfair advantage against the enterprises.” – Bradley Younge
  • “You're really just using [AI] as a tool. And that was kind of the other aspect of the vision, was to really make these agents—to create an agent workforce that is proactive.” – Bradley Younge

💡 Actionable Takeaways

  • ✅ Audit your "busy work" now. Identify 1-2 repetitive weekly tasks (like summarizing industry news, following up on invoices, or updating your CRM) that an AI agent could automate immediately.
  • ✅ Frame your first AI hire. Conceptualize an "AI Chief of Staff." What are the core business goals, risks, and worries you would delegate to this role if it existed?
  • ✅ Think integration, not isolation. Look for AI platforms that connect with the systems you already use (like Microsoft 365, QuickBooks, and HubSpot) to unlock true, seamless automation.
  • ✅ Prioritize governance and safety. When exploring AI solutions, ask about controls, auditing, and "human-in-the-loop" approvals for critical actions like external communications or financial transactions.

🔗 Links & Resources

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