In this bold and honest conversation, Erik sits down with Jeremy Brady, National Sales Manager at G Adventures, to explore what it really takes to lead high-performing teams in 2025. They unpack why the old sales playbook doesn’t work anymore, how to build a values-driven hiring process, and why “culture fit” isn't just a buzzword—it’s a strategic advantage. Jeremy shares hard-earned insights from leading through COVID, reinventing hiring practices, and learning how to create psychological safety during interviews. It’s a masterclass in modern leadership, hiring with intention, and building cultures that last.

👤 About the Guest

Jeremy Brady is the National Sales Manager at G Adventures
, a global adventure travel company known for its commitment to community tourism and values-driven leadership. With a background in hustle culture sales and over a decade of experience, Jeremy now helps shape a future of leadership that prioritizes authenticity, alignment, and long-term impact.

🧭 Conversation Highlights

• From “boss to friend” tension: Jeremy’s journey becoming a leader among former peers
• The radical shift from hustle culture to intentionality in hiring
• How G Adventures uses a "G Factor" (now “Backstage Pass”) to detect culture alignment
• Designing interview processes that prioritize core values over credentials
• Leveraging “Working Genius” and hedgehog concepts to build balanced sales teams
• How COVID forced a rethink on team engagement, fulfillment, and purpose
• The power of letting top performers fail (and why you shouldn't rescue them too early)
• Turning travel sales into meaningful social impact work

💡 Key Takeaways

• Hire for alignment, not just performance: Core values are a better predictor of success than previous results.
• Disruption reveals truth: Swearing, surprises, or even a ball pit interview can surface real insights about a candidate.
• Let them fail forward: Growth comes from patterns of reflection, not perfection.
• Sales isn’t about closers: Balanced teams with varied strengths perform better long-term.
• Create psychological safety: The best interviews feel like conversations, not interrogations.

❓ Questions That Mattered

• How do you build trust with candidates while still vetting them honestly?
• What’s your process for uncovering a candidate’s core values?
• How can companies avoid hiring “brilliant jerks”?
• What signs reveal that someone is thriving—or just coasting on past wins?
• How do you push a top performer to grow without deflating them?

🗣️ Notable Quotes

“You're gonna f*** up—just don't do the same f*** up twice.”
—Jeremy Brady

“If we look the same five years from now, something's wrong.”
—Jeremy on constant reinvention at G Adventures

“The candidate isn’t applying to prove they’re good enough. We’re seeing if we’re a fit for them.”
—Jeremy Brady

“When you’re in charge, take charge. When you’re not, stop trying to be.”
—Erik Berglund

“Empathy is a superpower—but without the sword of accountability, it can become a crutch.”
—Erik Berglund

🔗 Links & Resources

• Follow Jeremy on LinkedIn
• Check out Jeremy's Instagram

In this timely and thought-provoking conversation, Erik and Alli explore what it means to lead in the age of AI. As team members start working with large language models, AI copilots, and digital assistants, leadership is no longer just about people—it’s about protocols. From new security risks and brain atrophy to digital clones and ChatGPT accountability, they map out the practical and ethical terrain of leading teams armed with supertools. If you lead a team (or will soon), this episode is your onboarding to the AI-powered workplace.

🧭 Conversation Highlights

• The two biggest risks of AI use: brain atrophy and data exposure
• Why quality control matters more in an AI-powered team
• Why leaders must create protocols for feedback and accountability—even with AI
• The difference between an algorithm and a large language model (and why it matters)
• How to teach your team to lead digital coworkers as effectively as human ones
• Wild but real scenarios: legal risks of cloning employees, sparring with AI board members, and managing chatbots that miss deadlines

💡 Key Takeaways

• AI doesn’t replace leadership—it raises the stakes. Tools can create speed, but humans still guide context, ethics, and accountability.
• If your team is using AI, talk about it. You can’t lead what you don’t understand or even know is happening.
• Data intimacy still matters. AI can generate insights, but only you can understand the story behind the numbers.
• Feedback isn’t just for people. You need to build clear “rules of engagement” with your AI tools—just like a new hire.
• Legal and ethical questions are coming. Who owns an AI clone of your employee? You might need to decide… soon.

❓ Questions That Mattered

• What does it actually mean to manage AI tools—not just people?
• How do you avoid letting your team’s strategic thinking atrophy?
• What conversations should leaders have about how AI is being used?
• When does generative content need more editing, not less?
• Who owns your digital avatar if you leave your job?

🗣️ Notable Quotes

“Generation is no longer the hard part. It’s quality and editing that are scarce now.” —Erik

“If you’re not using part of your brain anymore, you’re going to lose it. AI can atrophy our thinking.” —Alli

“You still need rules of engagement—just like with a real human.” —Alli

“You can’t run a report for the stories you didn’t ask your AI to tell.” —Erik

“This isn’t a reason not to use AI—but it is a reason to lead differently.” —Erik

🔗 Links & Resources

• Listen to other episodes co-hosted with Alli

🧠 Erik’s Take

In this reaction episode, Erik reflects on his conversation with Chase Damiano—COO turned systems thinker, father-first decision maker, and founder of Humans at Scale. What stood out most? Chase doesn’t just talk strategy—he tests it. Erik highlights how Chase treats business like a living lab, combining intention, iteration, and humanity into every decision. This episode zooms in on what it really means to lead with intentionality, how systems thinking plays out in the real world, and why experimentation might be the most underrated leadership muscle of all.

🎯 Top Insights from the Interview

• Treat your business like a laboratory — Chase runs experiments, not assumptions. Every major move, from coffee trikes to national distribution, was a test.
• Systems thinking as a leadership edge — With a background in systems engineering, Chase applied operational rigor to startups and service-based businesses alike.
• Intentionality isn’t just personal—it’s operational — Whether choosing where to live or what to launch, Chase methodically tests alignment with values.
• Values-driven decisions scale — From turning down a promising job to stay close to his son, to shaping his new company, Chase walks the talk.
• Even your best ideas are just hypotheses — From sales scripts to team culture, everything is a test—until feedback proves otherwise.

🧩 The Personal Layer

Erik shares how Chase’s lens of systems + intention got him thinking about his own decisions—especially around parenting, leadership, and product testing. There’s a quiet kind of boldness in how Chase lives: methodical, values-aligned, and open to pivoting. That balance between rigor and flexibility? Erik sees it as an antidote to stuck leadership.

🧰 From Insight to Action

• Ask yourself: “Am I treating this strategy like a test?”
• Revisit your personal or professional goals—are they aligned with your values or inherited assumptions?
• Design small feedback loops for your next big decision. What would it mean to test it before scaling it?
• Consider how empathy + systems thinking can coexist in your leadership style.
• Journal prompt: “Where am I stubborn where I should be curious?”

🗣️ Notable Quotes

“Our businesses are just experiments.”

“The more you can recognize you’re in the middle of a test, the easier it is to treat pushback as feedback.”

“You kind of have to know where you want to go in order to figure out the best path to get there.”

“Intentionality and systems thinking—what a deadly one-two punch.”
“Every interaction—product, sales, culture—it’s all a lab if you’re willing to see it that way.”

🔗 Links & Resources

• Listen to Chase Damiano's Episode