Retained Trust

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 Episode:

[00:00:00] Karl introduces the solo episode and why he’s tackling the topic of selling a digital agency.

[00:00:49] The emotional complexity of selling a business and how common seller regret is.

[00:02:07] Overview of how buyers value agencies and what comps are.

[00:03:02] Definitions of EBITDA and SDE, and why they matter.

[00:04:06] Why larger agencies command higher multiples—autonomy and management depth.

[00:06:18] Key drivers of higher valuations: owner independence and recurring revenue.

[00:08:07] Client concentration risk and how it can lower your offer.

[00:09:22] How margins and growth rate influence what buyers are willing to pay.

[00:10:56] Understanding the landscape of potential buyers—from competitors to private equity.

[00:12:39] Building relationships with competitors years in advance of selling.

[00:13:48] The role of private equity and individual buyers in different deal sizes.

[00:15:32] Deal structures explained: cash at close, earnouts, seller financing, equity rollovers.

[00:19:59] What happens during the LOI and due diligence phases of a sale.

[00:22:48] Asset purchase structures and why they’re common in agency sales.

[00:23:45] Why legal counsel is essential at multiple stages in the sale process.

[00:24:57] Common seller mistakes: misunderstanding valuation and not seeking multiple offers.

[00:26:29] Post-sale responsibilities, expectations, and the risk of regret.

[00:27:59] Planning your next chapter and the importance of knowing your “what’s next.”

Links:

Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes

Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

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 of AI in modern agency operations. 

Key Points From This Episode: 

[00:00:27] Lana's memorable dive into a WWII bomber wreck near Croatia. 

[00:02:18] Overview of Cherry Red Content and its specialized approach. 

[00:03:27] Ideal clients: Bootstrapped startups seeking targeted growth. 

[00:04:12] Benefits and challenges of working with hands-on founders. 

[00:06:40] Understanding product marketing and its role in SaaS. 

[00:09:27] The relationship between product marketing and content. 

[00:10:07] Lana’s insights from working at Contently and transitioning to entrepreneurship. 

[00:13:40] Acquiring clients through LinkedIn, referrals, and community engagement. 

[00:14:50] Challenges and shortcomings of using Google Ads for client acquisition. 

[00:16:45] Cherry Red’s sales approach: consultative and strategic. 

[00:18:22] Advice for early-stage founders hesitant about marketing. 

[00:19:53] Key lessons from the book "The Mom Test" about validating startup ideas. 

[00:21:58] Differences between generating and capturing market demand. 

[00:23:25] Coaching founders through marketing fears and mental roadblocks. 

[00:26:18] Lana’s involvement and her team's structure at Cherry Red. 

[00:28:00] How AI tools are used effectively within Cherry Red’s workflows. 

[00:31:08] Moving toward entertainment-driven, engaging B2B content. 

[00:32:26] Challenges in harnessing founders' insights and keeping up with trends. 

[00:34:12] Hiring strategy: prioritizing entrepreneurial experience over specific hard skills. 

[00:36:34] Lana’s satisfaction in solving client problems and creating positive impact. 

[00:37:47] Challenges of entrepreneurship: constant context switching and prioritizing tasks. 

[00:39:30] Book recommendation: "The McDonaldization of Society" and its implications for agency work. 

[00:41:32] Finding a balance between standardization and creative flexibility. 

Links: 

• Lana Rafaela on LinkedIn: https://www.linkedin.com/in/lana-rafaela-326b5b211/?originalSubdomain=hr 
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes 
• Cherry Red: https://cherryredcontent.com/ 
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com  

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 episode and introduces Manny, highlighting their in-person workshop. 

[00:01:29] Manny shares podcast consultant’s 11% growth and how the team drives it forward. 

[00:02:47] Discussion on raising prices, improving contracts, and filtering ideal clients. 

[00:04:34] Doubling sales calls, better lead quality, and SEO’s long-term value. 

[00:05:11] How referrals and show notes discounts boost deal flow. 

[00:06:09] Bringing in salespeople and upselling existing clients. 

[00:07:48] New pricing for podcast launch programs to align incentives. 

[00:08:15] Code of conduct and walking away from controversial shows. 

[00:10:33] Moving upmarket at Draft.dev and signing larger clients. 

[00:11:09] Building a work-life balance that allows Manny to spend time with family. 

[00:13:02] Maintaining flexibility for employees and high client satisfaction. 

[00:13:57] Emphasizing accountability alongside flexibility. 

[00:14:36] Recent acquisition through long-term relationship building. 

[00:16:04] The importance of consistent follow-up for deals and sales. 

[00:18:24] Setback: SBA policy changes impact their acquisition strategy. 

[00:20:32] Adapting to new realities and focusing on building internal playbooks. 

[00:28:11] Standardizing sales, marketing, and operational systems. 

[00:32:20] Leadership transition at Draft.dev and training the next CEO. 

[00:35:01] Keeping opportunistic acquisitions on the radar. 

[00:37:15] How AI impacts agency owners and why some are exiting. 

[00:39:20] Adapting to AI-driven changes in SEO and service delivery. 

[00:44:03] Staying up to date to guide clients through generative AI changes. 

[00:49:13] Early results of content refresh efforts and AI citations. 

[00:55:01] Why industry knowledge and trust still matter despite AI tools. 

[00:56:07] Manny reflects on balancing fatherhood and business leadership. 

Links: 

• Manuel Weiss on LinkedIn: https://www.linkedin.com/in/manuelweiss1986/?originalSubdomain=at 
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes 
• Draft.dev: https://draft.dev/ 
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com  

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 onto a business you love.

Key Points From This Episode:

[00:00:00] Karl introduces JD and the Retained Trust podcast’s focus on agency owners.

[00:00:40] JD shares his woodshop hobby and working from his backyard “little slice of Farmerville.”

[00:05:06] JD’s start with Simple Focus and the shift from web design to usability and UX.

[00:08:43] Buying Pulse and how JD grew it by leveraging Simple Focus’s spare cycles.

[00:10:07] Acquiring Ballpark from MetaLab’s Andrew Wilkinson and how that shaped JD’s portfolio approach.

[00:12:48] Additional acquisitions: Sifter, Temper, Pop Survey, and operating a portfolio of small SaaS.

[00:13:53] How JD’s dev team structure keeps SaaS overhead lean and returns high.

[00:16:09] Why the small SaaS acquisition market has changed and what JD looks for now.

[00:21:56] JD’s current focus: sharpening Simple Focus’s brand and client relationships.

[00:25:19] The difference between running an agency vs. a SaaS portfolio — people vs. products.

[00:28:16] Lessons learned from merging agencies and why culture fit makes or breaks it.

[00:31:09] On not everyone wanting to be an entrepreneur — and why that’s okay.

[00:33:41] JD’s approach to delegating and staying in his zone of genius.

[00:38:44] Managing stressful clients by matching them to the right team member.

[00:39:37] Staying close to sales and work to keep the agency competitive and relevant.

[00:42:08] The balance between stepping back and staying connected as an owner.

[00:45:14] JD’s reading picks and closing thoughts on success and staying humble.

[00:46:05] Where to connect with JD online.

Links:

• JD Gaffam on LinkedIn: https://www.linkedin.com/in/jdgraffam
• Simple Focus: https://simplefocus.com/
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

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 purpose.

Key Points From This Episode:

[00:00:00] Louis explains how his podcast-based YouTube channel grew to 13,000 subscribers.

[00:03:19] How viral clips of famous entrepreneurs drove thousands of new followers.

[00:04:34] Why Louis had to take those clips down—and what came next.

[00:05:15] What keeps Louis interested in podcasting after several years.

[00:06:51] How podcasting serves as a tool to learn directly from domain experts.

[00:09:56] Overview of Orbit’s three branches: Marketing, Metrics, and Flows.

[00:13:55] How their AI tool for newsletter automation came to life.

[00:15:07] Why newsletters were chosen as Orbit Marketing’s first major offer.

[00:16:58] The internal evolution from services to scalable software.

[00:17:43] Louis reflects on his personal motivations and the broader vision.

[00:20:50] How Orbit ties into co-founder Sean’s goal of self-funded space R&D.

[00:23:08] Why the path is “services → software → space.”

[00:24:56] The threshold for stepping back from services to focus on product.

[00:26:38] Value in following through instead of chasing shiny new projects.

[00:28:23] Louis shares why newsletters remain an ideal medium.

[00:31:41] Personal story of how Louis built newsletter habits in college.

[00:33:32] Using a newsletter as a long-term nurture tool for leads.

[00:35:35] Lessons learned from early mistakes in outsourcing sales.

[00:38:01] How Orbit used relationship-based outreach and pricing strategy to grow.

[00:42:41] Behind-the-scenes: how Orbit’s ops team delivers dozens of newsletters weekly.

[00:47:40] Tech stack and internal tools that make Orbit’s workflow scalable.

[00:49:35] The hidden tradeoffs of location freedom and flexible schedules.

[00:52:34] Managing psychology as a founder through highs and lows.

Links:

Louis Shulman on LinkedIn: https://www.linkedin.com/in/louisshulman/

Orbit: https://www.orbitmarketing.io/

Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes

Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

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 sell in three years or ten, this conversation outlines how to ensure your business is truly built to exit.

Key Points From This Episode:

[00:01:07] Len's early exposure to business through his family's funeral home

[00:03:21] First client story that sparked Len’s focus on exit planning

[00:04:32] The high-impact, multi-year process of selling a business

[00:05:46] Why exit planning is just business planning with an end date

[00:06:36] Common mistakes business owners make before selling

[00:08:28] The underestimated timeline of getting a business ready to sell

[00:10:25] Why clean books and recurring revenue matter to buyers

[00:12:33] The risk of having most of your net worth tied to your business

[00:14:54] Three-legged stool of exit readiness: business, financial, and personal

[00:16:04] What buyers actually value beyond financials

[00:17:18] Breaking down intangible capital: structural, customer, social, human

[00:20:24] How risk lowers business valuation

[00:24:20] The challenge with revenue-based valuations

[00:27:00] Advice on intermingling personal expenses in business

[00:31:10] The different types of buyers and their motivations

[00:34:57] Importance of aligning exit terms with personal goals

[00:38:42] Understanding cash at close, seller notes, and earnouts

[00:43:32] The emotional toll and regret of unplanned exits

[00:46:07] Why entrepreneurs struggle with life post-exit

[00:49:48] Book recommendations: Built to Sell and The E-Myth

[00:50:56] Where to find Len and access his free business valuation tool

Links:

• Len Bruskiewitz on LinkedIn: https://www.linkedin.com/in/lbruski/
• Greater Heights Coaching: https://greaterheightscoaching.com/
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

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 digital agency.

Key Points From This Episode:

[00:00:00] Rebecca shares how Maximize Partners 10x’d revenue in four months.

[00:02:06] Her background at DigitalOcean and MongoDB and how it shaped her approach.

[00:05:21] Origin and evolution of Sponsored, a marketplace for developer content creators.

[00:08:27] Transitioning from a marketplace model to a full-service agency.

[00:11:58] Educating technical founders on the value of marketing.

[00:14:04] Marketing’s role in standing out in the crowded dev tools landscape.

[00:15:51] Why Maximize avoids long-term enterprise engagements.

[00:21:00] Leveraging VCs, networks, and reciprocity for client acquisition.

[00:24:23] Using non-spammy BDR outreach to grow pipeline via LinkedIn.

[00:27:56] Maintaining hands-on delivery and scaling via a vetted expert network.

[00:32:27] Long-term strategy for hiring and expanding the partner model.

[00:35:55] Rebecca on what keeps her motivated: great clients and a great team.

[00:39:44] The hardest parts: dealing with uncertainty and market timing.

[00:43:58] Books and media that shape Rebecca’s perspective (and what doesn’t).

[00:46:24] Goals for next year: hiring, scaling, and investing more in clients.

Links:

• Rebecca Mosner on LinkedIn: https://www.linkedin.com/in/rebecca-mosner/
• Maximize: https://maximize.partners/
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

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 and aggressive goals.

Key Points From This Episode:

[00:00:00] Garrett's passion for the complexity and human challenges of agency work

[00:04:01] Why the idea of “elevating out” of your business is a myth

[00:06:08] Garrett’s executive structure and leadership style at Directive

[00:08:12] How he sets pace and alignment through strategic initiative planning

[00:12:14] The need for constant service reinvention in marketing agencies

[00:14:35] How Garrett tested and scaled paid channels with gift card demos

[00:17:46] Why proper contracting and LTV shape agency scalability

[00:20:56] The value of tightly focusing on one service for one persona

[00:23:17] Smart cross-selling: building services based on client delivery pain points

[00:24:14] Why Garrett launched Abe, a LinkedIn-only ads agency

[00:26:53] Directive vs. Abe: how focus improves clarity and execution

[00:28:23] The logic behind pre-hiring and betting big once a year

[00:29:11] Shifting from mid-market to extremes: startups and incumbents

[00:32:45] Garrett’s take on the myth of “passive income” from agency ownership

[00:34:22] Using acquisitions to gain capabilities and reduce CAC

[00:36:55] What makes an agency acquisition worthwhile (and what doesn’t)

[00:38:10] Lessons from failed expansions and why he'd buy instead of build

[00:41:20] Why coaching other agency founders is Garrett’s favorite work

[00:44:05] How most growth challenges tie back to leadership and structure

[00:47:47] Book recommendations on professional services, hiring, and strategy

Links:

• Garrett Mehrguth on LinkedIn: https://www.linkedin.com/in/garrettmehrguth/
• Directive: https://directiveconsulting.com/
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

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 inbound pipeline.

Key Points From This Episode:

[00:00:00] Aman reflects on transitioning from number two to starting his own agency.

[00:02:31] Insights gained from leading inside someone else’s business.

[00:04:41] Why personal branding is the overlooked growth channel.

[00:07:28] LinkedIn as a golden opportunity for impressions and inbound leads.

[00:09:20] Why most agency owners don’t commit to personal branding.

[00:13:17] The changing landscape and difficulty of cold email.

[00:17:27] LinkedIn spam detection and outreach effectiveness.

[00:20:24] Balancing long-term strategy with chasing growth hacks.

[00:25:26] Aman’s lead magnet strategy for driving inbound leads on LinkedIn.

[00:29:40] Creating problem-aware audiences and converting them to clients.

[00:31:01] Why unclear ideal client profiles hold agencies back.

[00:36:58] Experimenting with niche messaging without changing your whole business.

[00:40:15] Incorporating AI in content production and agency workflows.

[00:43:23] Why larger companies outsource risk as much as output.

[00:47:33] Using AI to generate content faster without compromising quality.

[00:49:03] Revisiting “The E-Myth” and applying it to agency growth.

Links:

• Aman Ghataura on LinkedIn: https://www.linkedin.com/in/amangrowth/?originalSubdomain=uk
• The Media Engine: https://www.themediaengine.co/
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com

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:

[00:00:00] John Doherty explains why he sold a marketplace business to focus on EditorNinja.

[00:01:48] The early days and first revenue from Credo’s lead generation model.

[00:04:57] Why marketplaces are hard to scale and how the pandemic disrupted a promising trajectory.

[00:07:12] Quality control and margin challenges in marketplace models.

[00:09:27] Building a managed service first as a strategic choice for long-term marketplace potential.

[00:11:25] The power of unfair advantages when launching a new business.

[00:13:02] How EditorNinja built an early talent pool of professional editors.

[00:15:27] The real value agencies add for both clients and freelancers.

[00:18:45] Why productization improves delivery and simplifies operations.

[00:21:38] Flexibility within a productized service—balancing standard offerings with custom needs.

[00:25:20] How productization makes sales more straightforward and scalable.

[00:29:06] Hiring and capacity planning when working with flexible, fractional talent.

[00:31:29] Incentivizing availability with minimum guaranteed payments.

[00:33:08] Why early-stage agencies shouldn’t start fully productized.

[00:36:34] Scaling requires expanding either services or target markets.

[00:38:08] Aligning opportunity vehicles with your skills and ambitions.

[00:41:32] Decoupling personal happiness from business outcomes.

[00:45:30] Reframing interruptions as privileges of entrepreneurship.

[00:47:05] Building an internal and external support network as a founder.

[00:48:59] John’s go-to book: The 4-Hour Workweek by Tim Ferriss.

Links:

• John Doherty on LinkedIn: https://www.linkedin.com/in/johnfdoherty/
• EditorNinja: https://editorninja.com/
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com