Episodes

In this episode of Retained Trust, host Karl Hughes speaks with John Ghiorso, founder of VantaFive, a venture studio and accelerator focused on niche marketing agencies. John shares his journey from bootstrapping Orca Pacific into an eight-figure business to selling it in 2020 and launching a new model for agency growth. They explore the importance of market timing, building enterprise value, and using customer acquisition data to scale profitably. John explains how VantaFive identifies emerging...

In this episode of Retained Trust, host Karl Hughes speaks with Christina Brady, CEO and Co-Founder of Luster.ai, about her journey from sales representative to startup founder. Christina shares lessons from her time at MetLife and Groupon, including the challenges of managing teams without proper leadership training. They examine why traditional sales methodologies often fall short and how Luster uses AI-powered predictive enablement to identify skill gaps before they impact revenue. The conver...

In this solo episode of Retained Trust, host Karl Hughes breaks down how service businesses can grow to $1 million in annual revenue. Drawing from his experience building and acquiring seven-figure agencies, Karl explains how to calculate the client base and pricing needed to reach the milestone, find service-market fit through customer conversations, and focus on a narrow beachhead market. He also covers referrals, demand capture, pricing for healthy margins, identifying operational bottlenecks...

In this episode of Retained Trust, host Karl Hughes speaks with Robert Tuchman of Amaze Media Labs and Audience Lift, and Adam Hendricks of The Podcast Consultant, about what it takes to grow a podcast. They discuss who should start a podcast, why audience quality can matter more than raw download numbers, and the role of consistency, strong audio, compelling content, and host enthusiasm in organic growth. Robert explains the paid promotion options available to podcasters, including contextually...

In this episode of Retained Trust, host Karl Hughes speaks with Rachael King, founder and CEO of Pod People, about building a podcast production company over nearly a decade. Rachael shares how her background in social media and PR led her to podcasting, why audio is such an effective medium for building trust, and how Pod People grew steadily as a bootstrapped agency. They discuss creative excellence, paid podcast promotion, building the right leadership team, managing client concentration and ...

In this episode of Retained Trust, host Karl Hughes speaks with Jeff Large, founder of Come Alive Creative, about his path from teaching middle school to building a podcast-focused agency. Jeff explains how his company evolved from web development into audio production, why podcasts can create unusually strong trust and engagement, and how businesses can use audio to support authority, sales, education, and client relationships. They also discuss choosing the right clients, the founder’s role in...

In this episode of Retained Trust, host Karl Hughes speaks with Dr. Jeremy Weisz about using podcasting to build relationships, strengthen trust, and create business opportunities. Jeremy shares how his path from chiropractic to podcasting led to lasting professional relationships and eventually to building Rise25. They discuss why guest relationships can matter more than download numbers, how podcasts can shorten sales cycles, and ways businesses can use interviews to strengthen referral and st...

In this episode of Retained Trust, host Karl Hughes welcomes back his business partner, Manuel Weiss, for a personal and business update. Manuel shares his move from Vienna back to the U.S., while he and Karl explain why they are shifting their attention toward the podcasting industry. They discuss stepping back from Draft.dev, acquiring Sundial Media and Rise25, and their approach to integrating teams while preserving brands that serve distinct parts of the market. Karl and Manuel also examine ...

Building a company is rarely the clean success story you hear after the fact. On Retained Trust, Karl Hughes sits down with founders and entrepreneurs to unpack what actually happens behind the scenes — the breakthroughs, the mistakes, the uncertainty, the painful lows, and the lessons that only come from building something yourself. These are candid conversations about entrepreneurship without the highlight-reel filter. Guests share the decisions that shaped their companies, the moments that ...

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...