Agency Confidential

Jeff Shannon
  • 5.0 (1)
  • Entrepreneurship
  • Updated Biweekly

Hosted by Jeff Shannon, Agency Confidential pulls back the curtain on what it really takes to build, scale, and survive in the agency world. Each episode features unguarded conversations with the operators, founders, and dealmakers shaping the modern agency landscape — from creative shop trailblazers to M&A insiders to growth strategists rewriting the rules. These are the lessons, missteps, mindset shifts, and battle-tested playbooks that built the agencies you admire… and the ones still in the making.

Episodes

  1. 2d ago

    Ep 8: What Breaks on the Way to $50M: Joseph Leon on Scaling an Agency

    Joseph Leon has seen agency growth from almost every angle: founding team member at Essence, senior leader at Plus Company, and now Managing Partner & Owner at GFL Ventures. In this episode of Agency Confidential, Joseph joins Jeff Shannon to break down what actually happens as an agency scales from a handful of people to hundreds. They get into the early days of Essence and its climb from four people to 200, the hires and operating systems that made that growth possible, and why so many founder-led agencies eventually hit a ceiling. Joseph explains what changes when an agency needs to move beyond founder instinct, why a clear North Star becomes critical as headcount grows, and how reinvesting during periods of rapid growth can compound an agency’s advantage. They also dig into the next major shift facing agencies: AI. Joseph shares why he sees the current moment as comparable to the early internet era, where agencies can still create meaningful differentiation, and why trust, relationships, experimentation, and reinvestment will matter even more as traditional agency work becomes increasingly automated. Key Timestamps 00:00 - What made early Essence different 06:02 - Scaling from 4 people to 200 11:36 - Why practitioner-led agencies hit a ceiling 17:44 - Moving from building to transforming an agency 22:53 - Why growing agencies need a North Star 29:35 - Using market tailwinds to build long-term advantage 33:14 - What happens to agencies in the AI era 35:43 - Where agencies can still create differentiation Links & Resources: Agency (peer network): https://www.joinagency.co/?utm_source=podcast Pilothouse: https://www.pilothouse.co/ Subscribe to the DTC Newsletter: https://www.directtoconsumer.co/

    Ep 8: What Breaks on the Way to $50M: Joseph Leon on Scaling an Agency

  2. Aug 14

    Ep 7: Hiring for the Agency of the Future

    Most agency founders know the work itself is changing fast. The harder question is what an agency has to become as execution gets increasingly commoditized. In this episode of Agency Confidential, Jeff Shannon sits down with Dee Dang, founder of Right Hook Digital, to talk about nearly a decade of building an ecommerce growth agency through multiple versions of the agency game. Dee shares how Right Hook grew from two founders taking almost any client they could get to a 120+ person agency, including the unexpected pre-revenue client that became a nine-figure luggage brand. He also breaks down why content and reputation became such powerful growth levers, how his approach to hiring has evolved, and what he looks for during an employee’s first 30, 60 and 90 days. Then Jeff and Dee get into the question every agency is working through right now: what happens to agency teams when AI can handle more of the execution? They talk about the rise of high-leverage strategists and problem solvers, what Jeff has learned from putting an AI agent in charge of a real ad account, and why agency founders need firsthand experience with the tools reshaping their businesses. What you’ll learn: How Right Hook Digital grew from two people to more than 120 at its peak How July Luggage became the lighthouse client that helped accelerate Right Hook’s growth Why consistent content can change the quality of clients and employees an agency attracts How Dee hires for culture, experience and “spongeability” Why the first 30, 60 and 90 days are the real job interview How Right Hook uses controlled pressure to evaluate new hires Where Dee looks for experienced agency talent Why problem-solving ability becomes more valuable as AI handles more execution What Jeff learned from letting an AI agent manage a live ad account How Dee is using AI as a second brain across meetings, management and decision-making Chapters: 00:00 How July Luggage found Right Hook before it had revenue 01:20 Dee Dang and the evolution of Right Hook Digital 03:35 From film production to Facebook ads 07:53 Building the agency from scratch 12:01 Finding the lighthouse client that changed everything 14:25 Why content became table stakes for agency growth 20:38 Hiring for culture, experience and problem solving 24:03 Why the first 90 days are the real interview 32:45 A surprising place to recruit experienced agency talent 34:08 What AI means for the future of agency teams 36:30 Jeff’s experiment with an AI-managed ad account 40:18 Building a team of better problem solvers 42:36 Why agency founders need to get hands-on with AI 44:30 Dee’s AI-powered second brain

    Ep 7: Hiring for the Agency of the Future

  3. Jul 31

    Ep 6: Why the Future Agency Runs on Systems

    “AI is really about proper operations.” In this episode of Agency Confidential, Jeff Shannon sits down with Jordan Ross, founder of Eight Figure Agency, to break down what AI adoption actually looks like inside agencies, from building agents and internal tools to fixing the operational foundations they depend on. Jordan shares what he’s learned working with more than 1,000 agencies, why the top 1% are already running highly automated closed-loop systems, and how his background managing 2,500 people at Amazon shaped the way he thinks about processes, SOPs, ownership, and scale. If you’re an agency founder or operator figuring out where AI fits into your business, this episode gets into where agencies are finding real leverage today, how to build infrastructure that can survive a rapidly changing AI stack, and what the agency team of the future could look like. What you’ll learn: Why strong operations are the foundation for effective AI adoptionWhere agencies are getting the most leverage from agents and automationWhy AI systems built by engineers require less ongoing maintenanceHow to identify which workflows are worth automating firstHow Amazon approached SOP ownership and process documentationThe difference between AI-forward and AI-compliant organizationsWhy decentralized AI adoption can create infrastructure problems at scaleHow skills, agents, and closed loops could reshape agency teamsWhy future agency strategists may manage far more clients and execution with AI Chapters: 00:00 The Core Operations Principles Agencies Need for AI 00:28 Meet Jordan Ross and Eight Figure Agency 01:25 From Amazon to Agency Operations 03:17 What Jordan Got Wrong Building a HoldCo 07:36 What Agencies Are Actually Doing With AI 10:46 Building vs Maintaining AI Systems 13:40 Where AI Creates the Most Agency Leverage 16:29 Why AI Adoption Starts With Operations 17:50 When Agencies Should Start Documenting Processes 19:44 How Amazon Handles SOP Ownership 22:05 The Operational Foundation for AI 24:29 Centralized vs Decentralized AI Adoption 25:52 The Problem With Building an Internal AI “Brain” 27:47 Building AI Infrastructure That Can Keep Changing 30:09 What the Agency of the Future Looks Like 32:34 The Strategist Agencies Will Need Next Links & Resources: Agency (peer network): https://www.joinagency.co/?utm_source=podcast Pilothouse: https://www.pilothouse.co/ Subscribe to the DTC Newsletter: https://www.directtoconsumer.co/

    Ep 6: Why the Future Agency Runs on Systems

  4. Jul 17

    Ep 5: How Brands Really Choose Agencies

    In this episode of Agency Confidential, Jeff Shannon sits down with Dan Gray, founder of Vendry, to unpack how brands actually search for, evaluate, and choose agency partners. Dan spent a decade working brand-side in growth and performance marketing before building Vendry, a platform that helps brands navigate more than 200,000 agencies. With thousands of agency relationships, 60,000 case studies, and direct visibility into why agencies win, lose, and get replaced, Dan sees the selection process from a perspective most agency owners rarely hear. What you'll learn: How Vendry narrows thousands of agencies down to the strongest three candidates Why agency selection requires both objective evidence and human judgment What makes a case study useful during an active agency search How brands use referrals, references, and AI to evaluate potential partners The red flags that quietly eliminate agencies from consideration Why brands want access to the team that will actually manage their account How specialization is changing the way brands divide agency work Where generalist agencies and AOR relationships still have an advantage How freelancers, consultants, SaaS, and in-house teams are reshaping the competitive landscape Why agencies should build their acquisition strategy around their strongest internal skill 00:00 - How brands find the right agency partner 00:30 - Introducing Dan Gray and Vendry 01:22 - Why Vendry was built from a brand-side perspective 04:13 - The hidden workload behind an agency search 06:37 - The science and judgment involved in agency matchmaking 08:57 - How Vendry vets and recommends agencies 12:14 - How Vendry's referral model works 13:40 - RFPs, RFIs, and how brands are using AI to make decisions 17:45 - Why case studies remain one of the strongest sales assets 20:37 - The value of anonymized case studies 22:01 - The red flags brands notice during the sales process 25:12 - The current agency market and growing competition 26:11 - Why agency specialization continues to accelerate 29:19 - In-housing, AI, and the flexibility advantage of agencies 30:49 - How the agency model could evolve over the next five years 32:12 - Where agencies can find leads in 2026 34:31 - Founder-led growth and finding the right acquisition channel 37:18 - Where to find Dan and Vendry Links & Resources: Agency (peer network): https://www.joinagency.co/?utm_source=podcast Pilothouse: https://www.pilothouse.co/ Subscribe to the DTC Newsletter: https://www.directtoconsumer.co/

    Ep 5: How Brands Really Choose Agencies

  5. Jul 3

    Ep 4: A conversation with the man who is everywhere with Nick Shackelford

    In Episode 4 of Agency Confidential, Jeff Shannon sits down with Nick Shackelford to unpack how he's built and run multiple agencies and brands at once, and why AI is changing what an agency report looks like. Nick has been in digital for 11 years, starting as a media buyer and building into a multi-agency, multi-brand operator. His team is adopting AI differently across paid media and retention, working through centralized versus decentralized AI infrastructure. He's also been publicly documenting his career for a decade, and is now seeing that content history show up inside the LLMs themselves. What you'll learn: AI's role as an input in the creative and reporting processThe WWW Framework: what had happened, what are you doing, and what you expect to happen nextWhy in-account adjustments matter less than creative learnings and offer iteration todayThe tradeoffs between centralized and decentralized AI adoption across departmentsHow being a public, consistent face has shaped Nick's deal flow and partnerships for a decadeHow new internal ventures get funded through "new money makes more money"Why the agency space is heading back toward fragmentation instead of consolidationThe tradeoffs of elevating employees into public-facing roles Links & Resources: Agency (peer network): https://www.joinagency.co/?utm_source=podcast Pilothouse: https://www.pilothouse.co/ Subscribe to the DTC Newsletter: https://www.directtoconsumer.co/

    Ep 4: A conversation with the man who is everywhere with Nick Shackelford

  6. Jun 26

    Ep 3: Building the Self-Driving Agency

    "It's the most exciting and daunting time to be an agency." In Episode 3 of Agency Confidential, Jeff Shannon sits down with Steve Krueger - founder of Jive, a commerce-focused technology agency with 17 years in the business - to dig into what building a self-driving agency actually looks like in practice. Steve is one of the earliest agency operators to implement AI across the full lifecycle of his business, from sales and proposals to project management and software development. He built Atlas, Jive's internal AI operating system, and is actively restructuring how his team runs projects around agentic execution. He's not theorizing about the future - he's already living in it. If you're an agency owner trying to figure out where AI fits, what to build, what to buy, and how to keep your team from just copy-pasting ChatGPT output into client deliverables - this episode gives you the clearest operational picture we've seen yet. What you'll learn: Why cheap execution is a fallacy and expensive mistakes are the real riskHow Atlas works as Jive's internal operational brain across the full client lifecycleWhy people are busier than ever despite more automationThe shift from time-and-materials billing to value-based pricing — and why AI is forcing itWhat "forward deployed engineers" are and why that role is explodingHow to build AI adoption inside an agency without blowing up what's workingWhy critical thinking is now the scarcest and most valuable skill on any teamWhat a six-person, $50M agency actually looks like — and why headcount is becoming a false metricHow to think about build vs. buy when every tool has a 12-month shelf life 00:00 - Why cheap execution is a fallacy and expensive mistakes are the real risk 00:58 - What Jive does and the "better life brands" philosophy 06:11 - How AI is changing the quality of client briefs and exposing weak critical thinking 09:32 - The "dentist" role: what agency leadership becomes in an AI-first org 12:50 - How Atlas works as Jive's internal operating system 24:42 - The death of time-and-materials and the rise of value-based pricing 30:06 - What forward deployed engineers are and why that role is exploding 33:24 - How to build AI adoption inside a team without burning the org down Links & Resources: Agency (peer network): https://www.joinagency.co/?utm_source=podcast Pilothouse: https://www.pilothouse.co/ Subscribe to the DTC Newsletter: https://www.directtoconsumer.co/

    Ep 3: Building the Self-Driving Agency

  7. Feb 13

    Ep 2: From $2,500 Retainers to $1B in Billings: The Story Behind Jon Bond

    “We started with a $2,500 retainer and a beach chair.” In Episode 2 of Agency Confidential, Jeff Shannon and Eric Dyck sit down with advertising legend Jon Bond—co-founder of Kirshenbaum Bond & Partners, which grew from a $2,500/month retainer to over $1 billion in annual billings before being sold in 2009. Jon pioneered guerrilla marketing in the '80s, built one of the largest independent agencies in the US, and maintained 27% profit margins year after year. Now an investor and consultant through Bond World, he shares the unfiltered truth about building, scaling, and sustaining a legendary agency. If you're an agency founder struggling with hiring, culture, positioning, or profitability—this episode breaks down the frameworks that actually work, from someone who's been there and done it at the highest level. What you'll learn: Why culture (specifically acceptance) was the secret to billion-dollar growthThe "near future" framework for staying ahead in a changing industryHow to achieve 27% margins (and why most agencies stay stuck at 5%)Why word of mouth still drives 95% of business (and how to engineer it)The hiring filter that predicts top performersHow to stop "picking up pennies" and land whale clientsWhy your agency should be your most important clientThe positioning mistake that keeps agencies smallHow to scale horizontally without losing focus Chapters: 00:00 The Secret to Building a Billion-Dollar Agency 00:30 From $2,500 Retainer to Industry Legend 04:12 How PR Made the Agency Instantly Famous 10:28 Culture as Competitive Advantage 15:14 The Word of Mouth Formula 20:24 Scaling to $100M+ Revenue with 27% Margins 27:11 Stop Chasing Small Clients 31:06 The "Near Future" Strategy for Staying Ahead Links & Resources: Bond World: https://bondworld.com Pilothouse: https://www.pilothouse.co/ Agency (peer network): https://www.joinagency.co/?utm_source=podcast Subscribe to the DTC Newsletter: https://www.directtoconsumer.co/

    Ep 2: From $2,500 Retainers to $1B in Billings: The Story Behind Jon Bond

  8. Jan 30

    Ep 1: Tom Shipley on Buying Growth: Scaling Your Agency Through Acquisitions

    “Any business problem can be solved with an acquisition.” In Episode 1 of Agency Confidential, Jeff Shannon sits down with investor and operator Tom Shipley to break down how agencies actually use M&A as a growth lever—from buying businesses with limited capital to structuring deals that reduce risk. Tom shares the stories behind his first acquisitions, the criteria he uses to identify potential deals, and why he sees growing opportunity for agency acquisitions amid AI disruption and market uncertainty. If you’re an agency founder, operator, or leader thinking about growth beyond organic sales, this episode explores the mental models, deal structures, and real-world mechanics behind acquisition-led growth. What you’ll learn: Why acquisition can outperform organic growth at scaleHow to define a “buy box” for acquisition targetsWhy volume of seller conversations mattersThe real purpose of due diligenceWhat integration looks like after an acquisitionHow AI and uncertainty are influencing agency exits and deals Chapters: 00:00 Any Business Problem Can Be Solved With an Acquisition 00:31 Meet Tom Shipley and His M&A Journey 01:57 Buying a Business When You’re Out of Cash 05:17 Using Acquisitions to Add Capability (Agency Examples) 08:03 Organic Growth vs Acquisition Growth (The Math) 12:18 Motivated Sellers and Creative Deal Structures 20:50 Due Diligence and Risk in Agency Acquisitions 24:33 Integration: What Actually Breaks Deals 30:11 AI, Market Uncertainty, and the Future of Agency M&A Links & Resources: DealCon: https://dealconlive.com Pilothouse: https://www.pilothouse.co/ Agency (peer network): https://www.joinagency.co/?utm_source=podcast Subscribe to the DTC Newsletter: https://www.directtoconsumer.co/

    Ep 1: Tom Shipley on Buying Growth: Scaling Your Agency Through Acquisitions
  • 8 Episodes

About

Hosted by Jeff Shannon, Agency Confidential pulls back the curtain on what it really takes to build, scale, and survive in the agency world. Each episode features unguarded conversations with the operators, founders, and dealmakers shaping the modern agency landscape — from creative shop trailblazers to M&A insiders to growth strategists rewriting the rules. These are the lessons, missteps, mindset shifts, and battle-tested playbooks that built the agencies you admire… and the ones still in the making.

Information

  • Creator
    Jeff Shannon
  • Years Active
    2026
  • Episodes
    8
  • Rating
    Explicit
  • Copyright
    © Jeff Shannon
  • Show Website
    Agency Confidential