Episodes

In this episode of Retained Trust, host Karl Hughes reconnects with Chris Gwinn, founder of Midwest CFO, to explore what he's learned in the first year of building his fractional CFO firm. Chris shares how refining driver-based forecasting models and digging into operational KPIs have helped his clients make smarter strategic decisions. The conversation covers the evolution of his sales approach, challenges in bookkeeping, and the critical importance of accurate gross margins. Chris also outline...

In this episode of Retained Trust, host Karl Hughes speaks with Jon Schroeder, founder and CEO of Joy Fluent. Jon shares the journey behind BrewJoy, a new plant-based product designed to prevent coffee-related teeth stains, and digs into his broader mission of improving wellness through everyday habits. He reflects on lessons from past ventures in data privacy and elder care, his MBA experience at Kellogg, and the mental demands of entrepreneurship. The conversation probes the contrast between c...

In this episode of Retained Trust, host Karl Hughes speaks with Jake Ward, founder and CEO of Data Protocol, a platform supporting developer education and experience. Jake shares his path from public affairs to tech entrepreneurship, including lessons from founding a trade association and working with major players like Google, Meta, and Intel. The conversation explores the complexities of developer engagement, sales in enterprise environments, and how empathy-driven design can deliver 30x indus...

In this episode of Retained Trust, host Karl Hughes speaks with Derek Delost, who shares his path from digital marketing burnout to agency ownership through the acquisition of DotYeti. Derek explains why starting from scratch wasn’t the right fit for him, how he navigated the risks of buying a business, and the realities of leading a team after a transition. He dives into the emotional and strategic challenges of the process—from deal structure to team restructuring—and how he’s positioning DotY...

In this episode of Retained Trust, host Karl Hughes speaks with Christian Banach, a growth consultant for marketing agencies with a background that spans concert promotions, celebrity events, and enterprise sales. Christian shares how he started an events agency in high school and grew it into a 15-year business working with artists like Lady Gaga and Pitbull. He explains how those early lessons in relationship-building now inform his agency consulting work. The two explore how founders can buil...

In this episode of Retained Trust, host Karl Hughes speaks with Jesse Gilmore, founder of Niche in Control and author of The Agency Owner’s Guide to Freedom. Jesse shares his journey from hustle-heavy entrepreneurship to creating a structured program designed to help agency owners reclaim their time and build scalable, founder-independent businesses. They discuss the triggers that lead owners to rethink their roles, how to measure real freedom in business, and why defining success beyond revenue...

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 ...

In this episode of Retained Trust, host Karl Hughes speaks with Greg Hickman, founder of Alt Agency. Greg shares his journey from running a full-service marketing automation agency to building a lean education and consulting company focused on helping agencies productize their services. They explore why productizing isn’t the enemy of creativity, how agency owners can structure a “service ladder” to match different buyer types, and the importance of self-awareness when defining success. Greg als...

In this episode of Retained Trust, host Karl Hughes speaks with Ross Brown, founder of Flex Ops and former managing director of a fast-scaling influencer marketing agency. Ross shares lessons from helping agencies scale past early growth hurdles, revealing how fear, overcommitment, and lack of clarity often keep owners stuck below the $1 million mark. Together, they explore the emotional and operational challenges of niching down, letting go of difficult clients, and building consistent business...

In this solo episode of Retained Trust, host Karl Hughes walks through the real-world process of selling a digital marketing agency. Drawing on his experience as both a buyer and seller, Karl lays out the key financial concepts—like EBITDA and SDE—that shape valuations, and explains what makes an agency attractive to buyers. He covers everything from owner independence and recurring revenue to deal structures and post-sale regret. Whether you're years away from selling or ready to explore offers...

In this episode of Retained Trust, Karl Hughes speaks with Lana Rafaela, founder at Cherry Red Content, a boutique agency focused on tailored content marketing solutions for early-stage, bootstrapped startups. Lana shares her experiences transitioning from freelancing and marketplace management at Contently to starting her own agency, highlighting the benefits of personalized client relationships. They explore the evolving landscape of product marketing, the critical role content plays within it...

In this episode of Retained Trust, Karl reunites in person with partner Manny to break down how they’ve scaled their agencies and the lessons they’re carrying forward. They discuss real growth numbers, sales call improvements, and smart client filtering to boost quality leads. Karl and Manny share hard-earned insights about strategic patience, SEO, referrals, and balancing family life with business goals. They also open up about leadership transitions, the impact of AI on services, and what it m...

In this episode of Retained Trust, host Karl Hughes talks with JD Graffam, founder of Simple Focus and operator of a portfolio of SaaS companies. JD shares how he grew from a small-town agency owner to running multiple businesses, balancing a love of craft (and nail guns) with a sharp eye for buying SaaS that makes sense. They examine today’s small acquisition market, agency mergers, culture fit, staying competitive, and the lessons JD’s learned managing teams, clients, and his own entrepreneuri...

In this episode of Retained Trust, host Karl Hughes sits down with Louis Shulman, co-founder of Orbit, to explore how a content marketing agency evolved into a multi-pronged venture encompassing data analytics, automation thannel to launching Orbit Marketing, Metrics, and Flows—each built arools, and an ambitious software roadmap. Louis shares the path from growing a viral YouTube cound a thoughtful blend of automation, services, and long-term vision. He discusses early-stage customer acquisitio...

In this episode of Retained Trust, host Karl Hughes speaks with Len Bruskiewitz, founder of Greater Heights Coaching, about how small business owners can better prepare for a successful exit. With decades of experience in tech and a background rooted in a third-generation family business, Len shares what it takes to move from running a business to exiting with clarity and value. They break down the emotional, financial, and operational components of a strong exit strategy—including the risks of ...

In this episode of Retained Trust, host Karl Hughes talks with Rebecca Mosner, co-founder of Maximize Partners, about the agency’s journey from a developer-focused content marketplace to a high-touch consultancy. Rebecca shares how she and her team 10x’d revenue in just four months, the challenges of educating technical founders on marketing value, and why they prefer working with early-stage startups over enterprise clients. They also explore hiring strategies, building a strong team culture, a...

In this episode of Retained Trust, host Karl Hughes sits down with Garrett Mehrguth, founder of Directive and Abe, to unpack what it really takes to build, scale, and sustain a high-performing digital agency. Garrett shares why he's drawn to the constant reinvention required in agency life, how he structures leadership across multiple teams, and the bold bets he's making—like launching a new LinkedIn ads agency and buying others through his HoldCo, More Good Capital. From hiring to contracting, ...

In this episode of Retained Trust, host Karl Hughes speaks with Aman Ghataura, founder of The Media Engine, about his evolution from a number two in a digital agency to starting and scaling his own business. Aman shares how his early agency experiences shaped his understanding of growth, and why he believes personal branding—especially on LinkedIn—is the most undervalued opportunity for agency owners today. The conversation explores cold email challenges, leveraging lead magnets, and AI’s growin...

In this episode of Retained Trust, host Karl Hughes speaks with John Doherty, founder of EditorNinja. John recounts the winding path from running a marketplace agency to building a thriving productized editing service. The two dig into the challenges of scaling, lessons from running managed marketplaces, and the operational trade-offs of productization. John shares what makes EditorNinja’s model sustainable, why flexible staffing is crucial, and how personal contentment plays a role in entrepren...

In this episode of Retained Trust, host Karl Hughes speaks with Susan Tyson, a fractional CMO and author based in Chicago. Susan breaks down how small business owners can handle marketing strategy without fluff or jargon. With a direct and practical style, she shares lessons from a decade of consulting and decades more in marketing across industries. From the value of a one-page strategy to the power of consistent branding and effective SEO, Susan highlights what works—and what wastes your time....

In this episode of Retained Trust, host Karl Hughes sits down with leadership coach and entrepreneur Patty Campagna to explore what makes entrepreneurial leadership unique—and challenging. Patty shares her journey from corporate banking to founding Leading Teams Inc., offering grounded insights from decades of working with leaders in startups and Fortune 100 companies. They examine common pitfalls founders face when transitioning from doers to leaders, discuss ego, decision fatigue, and the need...

In this episode of Retained Trust , host Karl Hughes is joined by Michael Drew, founder of Book Retreat and a veteran of the publishing world with over 130 New York Times bestsellers under his belt. Michael opens up about his path from a high school dropout to a leader in book marketing, sharing lessons on influence, mentorship, and entrepreneurial growth. The conversation explores Michael’s innovative outlining system that demystifies book writing for non-authors, the structure and strategy beh...

In this episode of Retained Trust, host Karl Hughes speaks with Simon Severino, founder of Strategy Sprints, about building scalable and sustainable agencies. Simon shares insights from his 22-year journey in go-to-market strategies, offering practical advice on pricing power, ideal client selection, and creating repeatable sales systems. They explore how agency owners can balance high-ticket services with scalable offerings, leverage AI for pipeline management, and design a business around thei...

In this episode of Retained Trust, host Karl Hughes chats with David Sliman, founder of Sales Proformance Consulting and a veteran entrepreneur. David shares his journey from launching a direct mail franchise in 1999 to building and selling a multi-million-dollar marketing business. He and Karl explore lessons learned in sales leadership, product positioning, business acquisition, and finding the right growth model. The conversation also touches on mentorship, consistency, and the balancing act ...