Retained Trust

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 opportunities, partners with entrepreneurs, and builds specialized agencies targeting rapid growth. The conversation also examines how artificial intelligence is transforming agency operations, why traditional production...

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 conversation also covers personalized coaching, building effective sales processes, and creating a culture where employees can grow beyond their leaders. Christina closes by sharing lessons from...

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, and hiring adaptable early employees. The episode offers a practical framework for building an agency that can consistently deliver value without requiring the founder to handle every...

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 targeted distribution through Audience Lift, while Adam and Karl examine the metrics that matter most for B2B shows, from watch-through...

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 margins, and why bigger is not always better. Rachael also explains why she wants to build a company she would...

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 sales, the rise of video podcasting, shifting client needs, and why agency owners should understand the difference between mastering a craft and bu...

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 strategic partnerships. Jeremy also explains his systems for staying in touch with contacts, choosing podcast guests, and using every episode as an intentional follow-up tool.

<...

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 how their roles are changing as they focus more on acquisitions, culture, delegation, and building repeatable integration systems...

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 tested them, and what they learned along the way.

If you’re building a business, thinking about starting one, or simp...

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 recruiting to structured assessments, while emphasizing culture fit, adaptability, and self-awareness as critical traits for long-term success.

Key Points From This Episode:<...

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 pricing decisions affect profitability. The episode highlights practical approaches to building momentum, standing out in a crowded market, and creating a business...

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 through rapid technological change. Karl and Greg also analyze how generative AI is reshaping SEO, content marketing, and outreach—affecting workflows, team structures, and the broader digital marketing ec...

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 often overlook when scaling or preparing for a sale.

Key Points From This Episode:

[00:00:00] Grant’s entrepreneurial journey and building Nonprofit Megaphone in...

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-term sales planning, and why he believes in both holding and exiting businesses. Tune in for a tactical and honest discussion on what it takes to scale service businesses in...

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 “getting in the game.” Will offers grounded advice for agency owners considering their next move—whether that's growth, sale, or acquisition. 

 <...

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 deal structuring, outsourcing, team management, and why high revenue but low margin businesses catch his attention. Mushfiq also dives into his preference for niche agencies, the importance of diversified revenue...

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 drive. The conversation wraps with Mark’s personal transformation, tackling health challenges through endurance training and building resilience. 

Key Point...

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 bring fulfillment. From lifestyle design to strategic business thinking, Dan delivers a grounded and practical conversation for anyone running a company.

Key Points From Th...

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 on identity, control, and emotional resilience in entrepreneurship—all while balancing travel, family, and a few good books. This episode offers a raw, b...

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 churn became a top priority—and how the sales flywheel reshaped his thinking. Tune in for a candid look at what it takes to grow an e...

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 outlines how he's scaling the business and reflects on personal growth through parenting and reading.

Key Points From This Episode

[00:01:16] Chris...

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 corporate and entrepreneurial leadership, managing decision fatigue, and the power of focus. Tune in for a candid, grounded look at what it...

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 industry engagement. Jake also introduces "experience operations"—a strategic framework to reduce friction and increase value across user interactions.

Key Points From This Episode

...

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 DotYeti to thrive in an evolving creative market. A must-listen for agency operators and aspiring business buyers a...

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 build predictable deal flow, what it means to niche intentionally, and why long-term business development strategies outperform quick wins. Tune in for...

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 is essential. Jesse also opens up about building his team, recovering from personal loss, and staying aligned with a long-term purpose.

...

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...

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 also breaks down the pitfalls of chasing scale without intention and why YouTube became his content platform of choice.

Key Points From This E...

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 development practices. Ross also reflects on his own journey into consulting and the mindset shift required to build a business that supports your personal goals.<...

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 now, this episode provides a practical roadmap to getting the exit you actually want.

Key Points From This...

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, and why founders should embrace their unique perspectives when marketing their companies. Lana offers practical guidance for startups struggling with pre-product-market fit marketing strategies and discusses the impact and role...

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 means to build systems that outlast any single founder. 

Key Points From This Episode: 

[00:00:00] Karl opens the ep...

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 entrepreneurial itch. Tune in for an honest look at what it really takes to build, run, and hold...

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 acquisition, operational workflows, and the deeper motivations that fuel his entrepreneurial journey. Tune in for a real-time view of what it means to scale smart—and with purp...

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 poor planning, how buyers actually evaluate businesses, and the critical role of independence from the owner. Whether you plan to...

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, and how Maximize balances hands-on delivery with scalable growth. Tune in for a candid, detailed look at what it takes to grow a specialized digi...

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, and how Maximize balances hands-on delivery with scalable growth. Tune in for a candid, detailed look at what it takes to grow a specialized digi...

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, reinvesting profit, and knowing when to acquire versus build, Garrett brings candid, high-energy insight for founders navigating uncertain markets an...

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 growing role in agency operations. Tune in for a practical breakdown of long-term marketing strategy, client targeting, and building a consistent inboun...

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 entrepreneurial growth. Whether you're scaling an agency or considering productized services, this episode is packed with grounded wisdom.

Key Points From This Episode:

...