Episodes

In this episode of Retained Trust, host Karl Hughes speaks with Kimley Cox, founder of Drive Talent, a retained search firm specializing in precision manufacturing. Kimley shares her journey from decades in recruiting to launching her own firm and refining a niche focus. The conversation examines how specialization builds trust, why many founders struggle to hire senior leaders, and how to evaluate candidates beyond resumes. Kimley also outlines practical hiring strategies, from proactive recrui...

In this special episode of Retained Trust, host Karl Hughes distills lessons from dozens of conversations with agency founders, consultants, and acquirers into a focused breakdown of what drives agency growth. The discussion covers the importance of maintaining a consistent sales pipeline, the impact of niching down, and why founders must take ownership of sales early on. Karl also examines the realities of inbound and outbound marketing, the risks of relying too heavily on referrals, and how pr...

In this episode of Retained Trust, host Karl Hughes speaks with Greg Heilers, co-founder of Jolly SEO, an agency focused on earned link building and media placements. Greg shares his unconventional entrepreneurial journey, from volunteering around the world to launching multiple agencies and eventually building Jolly SEO into a productized service. The conversation examines lessons learned from early business failures, the value of partnerships, and the challenges of running service businesses t...

In this episode of Retained Trust, host Karl Hughes speaks with Grant Hensel, founder of Nonprofit Megaphone and managing partner at Entrepreneur Capital. Grant shares how he built a highly specialized agency serving nonprofits through the Google Ad Grant program, why niche focus and EOS transformed the business, and how he transitioned into acquiring and investing in small, enduring companies. They examine entrepreneurship through acquisition, common mistakes buyers make, and what agency owners...

In this episode of Retained Trust, host Karl Hughes speaks with Peter Kang, co-founder of Barrel and Barrel Holdings. Peter shares his 18-year journey in building a digital agency from the ground up, navigating the shift from generalist to e-commerce specialist, and eventually stepping away from daily operations. The conversation explores strategies behind launching new agencies, acquiring others, and managing leadership transitions. Peter offers grounded insights on financial structure, long-te...

In this episode of Retained Trust, host Karl Hughes chats with Will Smith, host of Acquiring Minds and partner at Minds Capital. Will shares how his frustration with startup ideas led him to entrepreneurship through acquisition (ETA), and how a niche podcast turned into a full-time business and investment platform. The conversation explores the realities of buying and running small businesses, including the balance of humility and hubris, the hidden risks of acquisition, and the power of simply ...

In this episode of Retained Trust, host Karl Hughes talks with Mushfiq Sarker, an experienced entrepreneur and founder of webacquisition.com. Mushfiq shares how he transitioned from flipping content websites to acquiring agencies and other online businesses. He reflects on lessons learned from managing over 200 acquisitions, the operational differences between flipping and holding, and how he identifies distressed agency assets with untapped potential. The conversation covers his approach to dea...

In this episode of Retained Trust, host Karl Hughes talks with Mark Bealin, founder of SearchLab, a Chicago-based digital marketing agency specializing in local SEO and PPC. Mark recounts his journey from side-hustle entrepreneur to leading a 50-person agency and dives into the pivotal decisions that shaped his company’s growth. He shares lessons learned from early failures, the power of niche specialization, the value of hiring for fit, and how becoming a father sparked a deeper entrepreneurial...

In this episode of Retained Trust, host Karl Hughes speaks with Dan Andrews—entrepreneur, podcaster, and co-creator of the Tropical MBA and Dynamite Circle. Dan recounts his entrepreneurial journey from corporate frustration to building and selling a successful business, and shares candid thoughts on passive income, business exits, and sustaining long-term value as a founder. They also explore the true leverage behind podcasting, building community, and why selling a business might not always br...

In this episode of Retained Trust, host Karl Hughes sits down with his co-founder Manuel Weiss for their quarterly update. They open up about recent challenges and wins across their portfolio, especially the contrasting trajectories of The Podcast Consultant and Draft.dev. From stepping back into the trenches of sales to refining product-market fit and repositioning offerings, Karl and Manuel dissect what’s working, what’s not, and how they’re adapting. They also share their personal reflections...

In this episode of Retained Trust, host Karl Hughes reconnects with Kurt Schnakenberg, founder of adbm.agency, to reflect on the agency’s growth, challenges, and pivotal lessons from its first 1.4 years. Kurt discusses the reality behind setting ambitious goals, reaching 300% growth, and shifting from founder-led sales to building a structured sales team. They explore the evolving product strategy, team dynamics, and the delicate balance of expansion and focus. Kurt also shares why reducing chur...

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...