Sold His Agency, Found His Calling: Steve Guberman’s Story

Episode Overview

Steve Guberman joins Jessica for a wide-ranging conversation that goes far beyond business strategy. From an accidental agency exit to an unimaginable loss, to launching a coaching practice, Steve shares the real, unfiltered story behind his company, Agency Outsight, and why authentic human connection is at the heart of everything he does.

Key Topics Covered

The Accidental Exit

Steve never planned to sell his agency. After nine years of building it, burnout hit fast — triggered by losing a seven-figure anchor client and the painful layoffs that followed. On his brother's advice, he put together a pitch deck and ran a "biz dev blitz" to agency owner friends, ultimately receiving three offers and selling to a PR firm he'd known and trusted for years.

Life After the Sale

Steve stayed with the acquiring firm for five years total — two years on an earn-out, then three more because things were going well. He shares what it felt like to finally let go of payroll stress and operate as an employee rather than a founder.

A Season of Loss and Reinvention

After leaving the agency in January 2020, Steve joined a new company with a clear CMO-track vision — but three months in, he lost his teenage daughter. Shortly after, COVID hit. He opens up about how that season of grief ultimately redirected his path, and why he's grateful for the unexpected support he found in that otherwise toxic workplace.

Launching Agency Outsight

After leaving the toxic job, Steve spent time in his garden, reconnected with agency owner friends in his New Jersey network, and was pointed to agency coach Kelly Campbell by multiple people simultaneously. That conversation gave him the blueprint. He launched Agency Outsight in October 2020 and hasn't looked back.

Getting Coaching Clients: Then vs. Now

1. Early days: Personal network outreach, starting with a $600/month client
2. Today: The Agency Bytes podcast serves as a content library and shortest sales cycle Steve has ever experienced — prospects come in already sold
3. Also working well: Speaking, webinars, brand partnerships, and in-person events ("IRL over URL")

On Selling Without Selling

Steve completed Sandler sales training but says he no longer sells at all. If the fit isn't right, he'll refer prospects to five other agency coaches. He wants clients who are ready and willing — not regretful ones he had to convince.

Books & Resources Mentioned

1. Traction by Gino Wickman (EOS)
2. A Course in Miracles
3. The Surrender Experiment by Michael A. Singer
4. Eckhart Tolle on Lewis Howes' podcast

Connect with Steve Guberman

1. 🎙 Podcast: Agency Bytes
2. 💼 LinkedIn: @AgencyCoach
3. 🌐 Agency Outsight

Work with Jessica

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