Honest, real-world conversations about what it actually takes to lead, grow, and protect a successful business — no corporate jargon, just clear insight from experts who've been in the room.
Start with the latest episode and dive into honest, real-world conversations about what it actually takes to lead, grow, and protect a successful business in today’s rapidly changing workplace.
From HR challenges and compliance risks to AI, leadership, culture, employee performance, and operational growth, each episode explores the issues business leaders are actively navigating every day — with practical insight from experts who have been in the room solving these problems firsthand.
No corporate jargon. No surface-level advice. Just clear, actionable conversations designed to help leaders make smarter decisions, support their people, and move their businesses forward with confidence. Because the best business conversations are the ones that actually help you do business better

Six episodes. Six expert perspectives. Real conversations with the leaders helping businesses navigate HR, growth, AI, operations, compliance, and the changing workplace.
Employment law expert helping businesses navigate compliance, risk, and HR liability.
🎙️What HR Mistakes Can Actually Get Your Company Sued?
HR and operations leader focused on helping growing businesses build smarter people strategies.
🎙️Do You Really Need HR, or Are You Fine Without It?
HR consultant specializing in compliance, employee relations, and reducing organizational risk.
🎙️What Happens If You Fire Someone the Wrong Way?
Helping businesses navigate outsourced HR solutions with a people-first approach.
🎙️When Is It Time to Outsource HR — and Is It Worth It?
AI and technology leader focused on practical innovation, operational efficiency, and the future of work.
🎙️AI in HR — What It Means for Your Business (and Your People)
Operations executive focused on scalable systems, accountability, and organizational performance.
🎙️What Does a PEO Actually Do — and Do You Need One?Jason Randall currently serves as Chief Growth Officer of Questco, and previously served as Questco's CEO for eight years. Questco is a national leader in the PEO/HR Support industry.
On Up In Your Business, Jason explores the real challenges small business leaders face every day — balancing people, performance, compliance, culture, and growth.