What if your intellectual knowledge isn’t enough anymore? As traditional expertise loses value, the real differentiators are wisdom, intuition, and emotional connection.

In this episode, Mike Grinberg, founder and CEO of Proofpoint Marketing, joins JR Lay to explore why thought leadership isn’t something you do—it’s an outcome you earn.

Most entrepreneurs dream about building a billion-dollar business—but the idea of giving things away for free feels counterintuitive. The truth is, some of today’s most successful companies like Zoom, Dropbox, and Canva were built on this exact model. If you’re still clinging to outdated go-to-market strategies, you’re leaving exponential growth on the table.

In this episode, JR Lay sits down with Dave Boyce, Executive Chairperson and EVP of Product at Winning by Design, to unpack his new book Freemium. With five SaaS exits under his belt, Dave reveals the 3-step formula behind freemium success: empathy, generosity, and metrics. Together, they explore how B2B entrepreneurs can harness these principles to win in an AI-driven, self-service economy.

If you’re ready to create value first, monetize second, and future-proof your business, this conversation will give you the clarity and confidence to level up.

One of the biggest challenges entrepreneurs face isn’t finding the next opportunity — it’s protecting their confidence while juggling it all. Over time, many founders get stuck on autopilot, doing the same things, talking to the same people, and slowly losing the perspective that once gave them their edge.

Jeremy Clark has found a different path. As a CEO who’s built and acquired businesses in financial services, he’s also chaired the Calgary Philharmonic Orchestra, served on McGill University’s science board, and even stepped on stage as a standup comic. His secret? Staying curious, building authentic relationships that span generations, and constantly putting himself in situations that stretch his perspective.

In this episode of the Level Up Business Podcast, Jeremy and host JR Lay explore how entrepreneurs can protect their confidence, expand their perspective, and adapt in ways that create growth both in life and in business. If you’ve been feeling stuck, stagnant, or burned out — this conversation will give you fresh energy and a practical playbook to level up.