Aug. 19, 2025

EP.43 - Freelancer to Multi-Brand Agency Leader with Greg Henry

EP.43 - Freelancer to Multi-Brand Agency Leader with Greg Henry
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Season 1

In this episode of Retained Trust, host Karl Hughes talks with Greg Henry, founder of Push10, about his evolution from solo freelancer to leading multiple specialized agency brands. Greg shares how a focus on higher-quality clients and strong branding work helped him scale, the lessons learned from targeting mission-driven organizations, and how splitting into niche sub-agencies opened new growth paths. They explore challenges in balancing resources across brands, navigating client budgets, and building recurring revenue. Greg also discusses the role of SEO in client acquisition, the importance of maintaining strategic partnerships with existing clients, and his long-term vision for a holding company structure. 

Key Points From This Episode: 

[00:00:00] Introduction to Greg Henry and Push10’s focus on nonprofits and social good organizations. 

[00:01:26] Moving from small clients to enterprise-level work by focusing on quality and strategy.  

[00:02:36] Lessons from adapting to disruptive tools like Squarespace and AI. 

[00:06:37] Greg’s early career path from mass communications to founding an agency. 

[00:09:31] Decision to hire, specialize, and expand into mission-driven branding. 

[00:11:43] Launching two additional niche brands for food & beverage and AEC clients. 

[00:13:40] Advantages of diversification across industries during downturns. 

[00:15:45] Pre-qualifying nonprofit leads to ensure budget alignment. 

[00:18:22] Narrowing niches within the mission-driven space to find higher-budget clients. 

[00:21:29] Starting with targeted landing pages before launching full niche brands. 

[00:22:26] Marketing challenges of running three agencies with shared resources. 

[00:24:47] Leveraging the parent agency’s scale alongside niche expertise in sales. 

[00:26:26] Early client acquisition via direct mail to agencies and using “we” instead of  

“I.” 

[00:28:42] Using SEO to dominate search terms in specialized niches. 

[00:30:53] How to identify and choose a niche based on data from past projects. 

[00:33:57] Retaining branding/web clients with maintenance packages and strategic check-ins. 

[00:37:50] Using six-month strategy reviews to reduce churn and upsell projects.

[00:39:53] Splitting business development focus between new clients and upselling existing ones. 

[00:42:16] Encouraging the whole team to help with sales and brand promotion. 

[00:44:25] Greg’s long-term vision of a holding company with multiple specialized agencies. 

[00:47:41] Equity-based managing partners as a solution for scaling multiple brands. 

[00:48:28] Book recommendation: Profit First by Mike Michalowicz. 

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