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“Good enough isn’t.”
In this episode, host Myles Biggs and Patrick sit down with Level Agency’s newest executive, Chief Revenue Officer, Howard Diamond, to talk about growth, leadership, and why strategy (not hype) should lead your AI adoption.

Howard shares lessons from 16+ years helping build a high‑growth agency, the poker‑player mindset he brings to decision making, and how Level’s no‑markup, fully transparent approach to media sets clients up for epic wins. You’ll hear why Level doesn’t have “an AI strategy”, we have a strategy enabled by AI, and what that means for marketers who don’t want to hand their competitive edge to the ad platforms.

In this episode, you’ll learn:

• How to turn AI into an advantage through orchestration (not inventing LLMs)
• Why transparency in media buying beats short‑term “cheaper” models
• The culture behind “good enough isn’t” and aiming for epic wins
• A CRO’s real job: amplify innovation for new and existing clients
• “Briefs on steroids”: using AI to show up radically prepared for pitches
• Guardrails for growth: data, creativity, and your own optimization levers
• Sales philosophy: lead with curiosity, problem‑solve, and serve the truth
• Early‑career advice: patience over virality, own your learning, and ship work
• Leadership that scales: mentorship, feedback, and one conversation at a time

Guest

Howard Diamond — Chief Revenue Officer, Level Agency

Hosts

Myles Biggs with Patrick

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Episode 1 – ChatGPT-5 and Monetizing LLMs
 

AI is moving fast, and not always in the way we expect. In this episode of Good Enough Isn’t, host Patrick Patterson (CEO) and co-host Myles Biggs sit down with Howard Diamond (CRO) of Level Agency about the launch of ChatGPT-5 and what it means for both power users and everyday professionals.

They dig into:

• Why ChatGPT-5 underwhelmed some heavy users
• OpenAI's agent mode potential (and its limits)
• The rise of competitors like Gemini, Claude, and Grok
• How Grok is testing ads inside AI responses
• Perplexity’s $34.5B bid for Google Chrome
• Meta’s AI ad suite that can build campaigns automatically

The conversation also looks at the bigger picture, trust, privacy, creative disruption, and why old-school tactics like direct mail might resurface in an AI-driven world.

If you want a candid, no-ego look at where large language models are headed, and how they’ll reshape marketing and innovation, this episode delivers insights you can’t miss.