Most companies talk about becoming “AI-first.” Very few actually stop the business to make it real.

Wes Schroll — Founder & CEO of Fetch — joins Wade to unpack what it actually takes to scale a consumer platform, evolve a decade-old company, and integrate AI without losing focus, culture, or trust. From building his first business at 14 to leading a loyalty platform that now influences more consumer spend than nearly anyone outside Walmart and Amazon, Wes shares the behind-the-scenes decisions that shaped Fetch’s growth.

They dig into Fetch’s unconventional business model, how Wes’s perspective on AI shifted from skepticism to urgency, and why leadership had to get hands-on — not delegate AI exploration to a task force. Wes breaks down the decision to shut down the company for a full week so 1,000+ employees could participate in an AI hackathon, the hard lessons learned from early automation missteps, and why simple, readable AI guidelines matter more than fear-based policy.

The conversation also explores how AI is changing founder–engineering dynamics, reshaping what counts as a competitive advantage, and lowering the barrier for non-technical leaders to communicate, prototype, and collaborate more effectively.

In this episode, you’ll hear:

• Why Fetch resisted calling itself a “well-oiled machine” — and what sustained scale really looks like.
• How a founder’s personal AI “aha moment” sparked a company-wide shift.
• Why task forces fail and hands-on leadership creates real momentum.
• What Fetch learned from shutting down the company for a week-long AI hackathon.
• How to evaluate AI aptitude, scalability, and vendor promises realistically.
• Why short, human-readable AI guidelines outperform long, punitive policies.
• How AI reduces expertise asymmetry between founders, product, and engineering teams.
• Lessons on resilience, responsibility, and surviving the emotional highs and lows of entrepreneurship.
• Why using AI isn’t “cheating” — and how leaders must reset that narrative.

Guest: Wes Schroll—Founder & CEO, Fetch

Most security playbooks weren’t built for an era where AI moves faster than policy. Rob T. Lee says the default answer of “no” is creating a far bigger problem: shadow AI — widespread, unsanctioned usage that quietly exposes organizations to risk.

Rob T. Lee — Chief of Research & Chief AI Officer at the SANS Institute — joins Wade to unpack pragmatic ways leaders can move forward without breaking things. From the “tinker/hacker” mindset that helps teams learn, to treating security like a lifeguard (not a chokehold), Rob lays out the short, repeatable moves that actually get enterprises experimenting safely: enable small experiments, create accountability partners (not mythical “AI champions”), red-team your integrations, and make governance part of the daily routine.

In this episode you’ll hear:

• Why a blanket “no” to AI creates shadow AI and greater risk.
• How to flip policy toward a cautious “yes” and act like a lifeguard, not a jailer.
• Practical training tactics: 30 minutes a day, micro-projects, and hackathons.
• What good AI governance looks like — rules of acceptable use, vendor checks, red teams, and regulatory thinking.
• Why executives and boards need to be hands-on learners, not just hire an “expert.”
• The origins and purpose of the SANS Secure AI Blueprint and how to use it to align strategy, governance, and operations.

Guest: Rob T. Lee — Chief of Research & Chief AI Officer, SANS Institute

Most enterprise AI talk sounds great in theory—until you try to make it work across 40 disconnected systems. Jason Cottrell says that’s exactly where the real wins are hiding.

As CEO of Orium (and the new president of the MACH Alliance), Jason has seen what happens when companies stop chasing one big AI solution and start stacking small, composable ones. The result? For one retailer, a 9-month transformation that led to 5x digital growth—and a repeatable roadmap any enterprise can follow.

In this episode, Jason and Wade unpack why “many agents, many jobs” beats the mythical all-knowing AI, how interoperability is quietly rewriting retail, and the cultural shifts that make automation actually stick.