Retained Trust

About Retained Trust

Want to know what it takes to build, scale, and sell your agency? Retained Trust is a weekly podcast where host Karl Hughes goes deep with digital service business owners to uncover the habits, tactics, and strategies they’ve learned to grow successful companies. Along the way, you’ll hear about Karl’s journey running and acquiring niche digital agencies as he learns from guests with a variety of backgrounds and experience levels.

Publisher

Karl Hughes

Category

business · business · business

Language

en

Explicit

No

First episode

28 Oct 2024

Latest episode

3 Nov 2026

Latest episodes

71 episodes in the feed.

1. 

   3 Nov 2026

   Beyond Organic Growth: Tristan Pelligrino on Buying Agencies and Building Sustainable Businesses

   In this episode of Retained Trust, host Karl Hughes speaks with Tristan Pelligrino, co-founder of Aragon Holdings, about building and acquiring marketing agencies. Tristan shares his journey from launching 522 Productions to founding Motion and expanding through acquisitions. They explore why strong leadership, recurring revenue, and operational systems matter when evaluating agencies, along with the challenges of cultural integration and founder dependency. Karl and Tristan also discuss SBA financing, creative deal structures, and the importance of maintaining relationships with potential sellers and investors. Tune in to learn how agency owners can prepare for an exit and how buyers can build sustainable businesses through strategic acquisitions. Key Points From This Episode: [00:00:00] Introduction and Karl welcomes Tristan to the show [00:01:02] Introduction to Aragon Holdings and its agency acquisition strategy [00:02:43] Tristan's entrepreneurial journey with 522 Productions and his eventual exit [00:05:38] How differing long-term visions led to a partner buyout [00:09:31] Operational challenges of running a video production agency [00:11:02] Founding Motion and expanding from corporate video into motion graphics [00:13:05] Transitioning to remote production, recurring content programs, and video podcasting [00:15:57] Why podcasts remain valuable for businesses in an AI-driven content environment [00:18:51] Exploring acquisitions as an alternative to rapid organic agency growth [00:23:13] Prioritizing strong leadership teams when evaluating acquisition opportunities [00:25:58] The importance of recurring revenue, healthy client relationships, and profitability [00:27:33] Assessing founder dependency and whether an agency can operate without its owner [00:29:31] How operational systems and EOS support accountability and business continuity [00:31:23] Challenges of assessing company culture during acquisition due diligence [00:35:01] Balancing cultural compatibility with necessary organizational changes [00:37:00] Integrating company values while making difficult decisions to protect business sustainability [00:39:19] Why maintaining financial reserves matters when agencies lose clients [00:40:30] Financial transparency and helping employees understand business sustainability [00:42:17] Comparing SBA financing, growth capital, and creative acquisition structures [00:45:42] Using seller financing, earnouts, and personal capital to fund smaller agency acquisitions [00:47:54] Why smaller agencies rarely receive fully cash-funded acquisition offers [00:50:19] Building a CRM-driven relationship network with agency owners, lenders, and investors [00:53:19] Where to connect with Tristan and learn more about Aragon Holdings Links: Tristan Pelligrino on LinkedIn: https://www.linkedin.com/in/tristanpelligrino/ (https://www.linkedin.com/in/tristanpelligrino/) Aragon Holdings: https://aragon-holdings.com/ (https://aragon-holdings.com/) Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes (https://www.linkedin.com/in/karllhughes) Production and editing by The Podcast Consultant: https://thepodcastconsultant.com (https://thepodcastconsultant.com)

2. 

   27 Oct 2026

   Building Eight-Figure Agencies: John Ghiorso on Venture Studios, Market Timing, and AI

   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 roles must evolve, and how founders can position their businesses for an AI-driven future. Key Points From This Episode: [00:00:00] Introduction [00:00:33] John Ghiorso's entrepreneurial background and journey from agency founder to launching VantaFive [00:01:48] How John turned an early Amazon sales opportunity into a successful agency business [00:04:20] The importance of continuous learning, reading, and connecting ideas to accelerate entrepreneurial growth [00:08:41] Transitioning Orca Pacific from a profitable lifestyle business into an eight-figure agency built to sell [00:11:38] Reinvesting profits into sales and marketing through a measured, incremental growth strategy [00:14:17] Using customer lifetime value, acquisition costs, and retention metrics to drive sustainable agency growth [00:17:13] The inspiration behind VantaFive and John's decision to build specialized agencies instead of pursuing traditional acquisitions [00:21:56] Why identifying emerging market trends and anticipating technological shifts are critical entrepreneurial skills [00:23:56] How VantaFive's venture studio model recruits entrepreneurs to launch and scale niche marketing agencies [00:25:56] VantaFive's goal of building agencies capable of reaching eight-figure revenue within three years [00:26:45] Identifying entrepreneurial leaders who can transition from scrappy startup founders to executives managing larger teams [00:28:55] How VantaFive reduces entrepreneurial risk through shared resources, compensation, and accelerated growth opportunities [00:30:20] Equity ownership, compensation, and incentives for entrepreneurs partnering with VantaFive [00:32:32] Inside VantaFive's studio and accelerator models and its portfolio of TikTok Shop, Reddit, LinkedIn, and short-form creative agencies [00:34:37] John's "comet theory" and how technological disruption creates opportunities for specialized agencies [00:39:33] Why strong market demand can make scaling a specialized agency significantly easier [00:40:24] How niche agencies can win Fortune 500 clients despite competition from established agencies of record [00:43:53] Rethinking agency operations around AI-powered production and human-led strategy, creativity, and client relationships [00:43:53] Why agency employees must develop management and delegation skills to effectively direct AI systems [00:50:37] How AI adoption could divide the agency industry between businesses that thrive and those that struggle to compete [00:51:34] Connecting with John through VantaFive's newsletter, LinkedIn, and agency partnership opportunities Links: John Ghiorso on LinkedIn: https://www.linkedin.com/in/johnghiorso/ (https://www.linkedin.com/in/johnghiorso/) VantaFive: https://www.vantafive.com/ (https://www.vantafive.com/) Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes (https://www.linkedin.com/in/karllhughes) Production and editing by The Podcast Consultant: https://thepodcastconsultant.com (https://thepodcastconsultant.com)

3. 

   20 Oct 2026

   Beyond the Sales Playbook: Christina Brady on AI, Sales Training, and Leadership

   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 hosting her podcast, Taking the Lead, and the importance of giving people opportunities to share their expertise. Key Points From This Episode: [00:00:00] Introduction and Karl welcomes Christina to the show [00:00:38] Christina Brady introduces herself and her journey from sales operator to CEO and Co-Founder of Luster.ai [00:01:59] How Christina entered sales through the insurance industry during the financial crisis [00:06:03] Why salespeople don't have to love their products but should care about the problems they solve [00:08:22] Christina's transition from financial services to technology sales at Groupon [00:12:45] How launching a challenging sales territory at Groupon led to Christina's first management opportunity [00:15:56] The difficulties of managing 35 employees without leadership training and the importance of coaching [00:19:38] Why no single sales methodology works for every organization or customer-facing team [00:23:49] Understanding the difference between sales processes and methodologies to improve team performance [00:27:42] The recurring revenue performance challenges that inspired Christina to create Luster [00:30:04] How Luster uses predictive enablement to identify and address skill gaps before they impact revenue [00:33:26] Measuring the right sales skills and using existing data to create personalized training [00:36:49] Applying AI-powered coaching across sales, customer success, support, and management roles [00:39:15] The challenges of introducing a new software category and positioning Luster alongside existing sales tools [00:42:20] How leadership responsibilities evolve from managing individual contributors to leading other leaders [00:44:51] Why effective leaders should help employees grow beyond their own positions [00:47:05] Recognizing that employees have different career ambitions and personal motivations [00:48:19] Lessons from hosting Taking the Lead and helping guests overcome self-doubt to share their knowledge [00:50:22] Karl's observations on creating better podcast conversations and helping guests feel comfortable Links: Christina Brady on LinkedIn: https://www.linkedin.com/in/christinapbrady/ (https://www.linkedin.com/in/christinapbrady/) Luster: https://www.luster.ai/ (https://www.luster.ai/) Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes (https://www.linkedin.com/in/karllhughes) Production and editing by The Podcast Consultant: https://thepodcastconsultant.com (https://thepodcastconsultant.com)

Who has been a guest on Retained Trust

Names identified in recent episode analyses. Showing up to five guests.

• Mark Bealin
• Dan Andrews
• Kurt Schnakenberg
• Chris Gwinn
• Jon Schroeder

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

31,553

Score snapshot 15 Sept 2025

Apple Podcasts (US)

5.0 / 5

1 ratings

Spotify

5.0 / 5

7 ratings

Podcast Authority Score: 46 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

50

Social presence

0

YouTube

72

Engagement

32