Deciding What You Actually Want — Steve Guberman

Show notes

Steve Guberman is the founder of Agency Outsight, where he helps agency owners build the business of their dreams—with clarity, purpose, and profit. A former agency founder who successfully exited his own firm, Steve now guides creative, marketing, and digital leaders through growth, positioning, and the complex decisions that come with scaling or selling an agency. Drawing on his experience as both a coach and M&A advisor, he helps owners understand what truly drives long-term value—financially and personally. As host of the Agency Bytes podcast, Steve shares real stories and lessons from top agency leaders to help others grow with intention.

Steve and I talk about what happens when agency owners chase what he calls "copycat goals"—revenue milestones and lifestyle markers borrowed from other people's social media feeds—instead of deciding what they actually want their business to give them. That question turns out to matter whether or not you ever plan to sell: the same work that makes a business sellable (reducing owner dependency, diversifying client concentration, building real systems) is often the same work that gives an owner back their time, their confidence, and a life that doesn't revolve around a business they secretly resent. Steve is candid about building himself a "job" rather than a business early in his career, and about the client concentration crisis and personal upheaval that eventually pushed him to sell.

Steve and I discuss:

• [02:17] – How Steve defines "agency," and why specificity matters when describing what you do
• [04:07] – What led him to start his own agency after working in-house and at other firms
• [05:03] – Winning an outsized contract, doubling in size, and the client concentration problem that followed
• [05:45] – How a divorce and losing his largest client collided in the same week
• [06:08] – How he approached selling the agency without any M&A experience, and why he chose the offer he did
• [07:28] – Why he now advises other agency owners going through the same journey
• [07:52] – Why so many owners have built a job with little market value rather than a sellable business
• [08:26] – The trap of building a new boss for yourself that you can't fire
• [10:13] – How long it typically takes to make a business valuable to a buyer
• [11:00] – Why Steve is at peace with his own current business not being sellable
• [11:48] – The main "discount factors" buyers look at: owner dependency, client concentration, and cash flow
• [14:05] – "Copycat goals," and why adopting someone else's milestones can work against you
• [15:01] – Optionality as the real payoff of optimizing a business, whether or not you sell
• [16:30] – Why business size isn't the real obstacle to delegating
• [17:26] – The owner's audit: identifying what you shouldn't be doing yourself
• [18:37] – Using freelancers, offshore talent, and AI to delegate affordably at any stage
• [19:00] – The mindset shift—letting go of control—that has to happen before delegation works
• [20:17] – How peer support and community help owners follow through on delegation and mindset shifts

Learn more about Steve at:

agencyoutsight.com

agencyoutsight.com/podcast

www.linkedin.com/in/agencycoach

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Smashing the Plateau features candid conversations with experienced professionals who are building businesses around their expertise and creating greater control over their work and their lives.

Each episode explores the decisions, challenges, and opportunities that come with independent work, drawing on the experiences and perspectives of people who have navigated them firsthand.

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