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Radio Programming Services - About Hole In the Wall Media

Steve Cannon standing by a tree with Indiana theater in the background.

Programmer. Coach. On‑Air Talent. Champion of Real‑World Radio.

Radio Is a Craft — And Steve Has Spent His Life Honoring It


Steve Cannon has spent more than three decades in radio, from the Lehigh Valley to Philadelphia, Milwaukee, Austin, Little Rock, Memphis, Raleigh‑Durham, Indianapolis, and now the Wabash Valley. He’s been an on‑air personality, a programmer, a brand builder, and a leader who knows how to take stations from “good enough” to “consistently winning.”

Steve’s philosophy is simple: radio should sound alive, local, and intentional — no matter the market size or the budget.

That belief is the foundation of Hole In the Wall Media.

A Career Built on Real‑World Results

Steve’s track record includes:

• Leading and coaching teams in major and mid‑major markets

• Developing and launching Classic Hits WJJK in Indianapolis — the first station to dethrone longtime market leader WFBQ

• Programming and guiding Marconi‑nominated stations

• Building brands that dominate ratings and earn listener loyalty

• Coaching talent at every level, from new board ops to seasoned morning shows

He’s known for blending big‑market discipline with small‑market practicality, giving stations the structure they need without the complexity they don’t.

Why Steve Founded Hole In the Wall Media

After decades inside corporate radio, Steve saw a gap:

small‑market stations deserve professional programming, coaching, and consistency — but rarely have the staff or budget to get it.

Hole In the Wall Media was created to fix that.

Today, Steve helps stations:

• Tighten their clocks and music flow

• Build stronger, more confident talent

• Improve ratings execution

• Sound live, local, and connected

• Stay consistent even with small staffs

It’s radio consulting built for the real world — affordable, actionable, and rooted in experience.

Two podcasters having a lively conversation in a professional studio.

Steve’s Approach

Every station is different, but Steve’s approach is always the same:

• Listen first

• Understand the brand

• Identify the simplest path to improvement

• Build systems that last

• Coach talent with clarity and respect

No jargon. No theory. Just practical steps that make your station better today.

Beyond the Studio

Steve is based in the Wabash Valley of Indiana, where he serves as Operations Manager and Brand Leader for multiple stations — including the Marconi‑nominated Country powerhouse HI‑99. He’s also an active on‑air personality who stays connected to the craft every day.

When he’s not programming or coaching, he’s writing Inside the Log, The Monthly Log, and building tools that help small‑market stations sound bigger and more competitive.

Close-up of two people shaking hands in agreement.

Let’s Build Something Great Together

If you want your station to sound cleaner, more consistent, and more confident — without adding payroll — Steve is ready to help.

Schedule a free 15‑minute strategy call and see what’s possible.

Schedule Your FREE STRATEGY SESSION

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