UNLOCK THE 13 SYSTEMS EVERY AGENCY OWNER NEEDS TO REACH 8 FIGURES:

https://bit.ly/41Sm05N

In this episode, Jordan Ross sits down with Jason Hennessey, founder of Hennessey Digital, to unpack what it really takes to scale a digital agency to multi–eight figures and successfully exit to private equity—without burning out or losing your life in the process.

Jason shares his 24-year “overnight success” journey, from running a standard SEO agency to intentionally building the “Lamborghini dealership of legal marketing.” He breaks down the mindset, systems, people strategy, and long-term intentionality required to move from six figures → seven figures → eight figures → exit.

This is not a hype-filled growth story. It’s a deep, honest masterclass on:

Why most agencies fail to scale past $10M

How to hire and retain true A-players

The hidden dangers of fast growth

The role of personal brand in enterprise-level deal flow

How intention, accountability, and resilience shape long-term success

If you’re an agency owner trying to break through the next revenue ceiling—or thinking about a future exit—this episode delivers real-world lessons from someone who’s done it twice.

Chapters

– Why Multi–Eight-Figure Agency Exits Are Rare

– Jason Hennessey’s 24-Year “Overnight Success”

– The Second Bite of the Apple (Private Equity Strategy)

– Running Multiple Successful Businesses Without Burnout

– Replacing Yourself to Scale Past $10M

– The Real Phases of Agency Growth (6 → 7 → 8 Figures)

– Cash Flow Stress at Scale (More Money, More Problems)

– Seeing the Game Like an Executive Strategist

– Product Obsession vs. Sales-Led Agencies

– Personal Brand as a Long-Term Growth Engine

– Designing the Agency You Actually Want to Run

– KPI-Driven Growth & Department Accountability

– Hiring A-Players and Accepting Lower Margins

– Why Most Agencies Can’t Retain Talent

– Paying Above Market & Retaining Rockstars

– Creating a Future That Didn’t Exist

– Running a Business for Profitability Before Exit

– Staying Grounded When Life Disrupts Business

– Learning from Failure Instead of Avoiding It

– Accountability Systems That Keep Founders on Track

– Designing a Life Beyond the Business

– Daily Habits & Creative Focus for Founders

To learn more go to 8figureagency.co

To reach Jason - https://www.linkedin.com/in/jhennessey/

- jasonhennessey.com

UNLOCK THE 13 SYSTEMS EVERY AGENCY OWNER NEEDS TO REACH 8 FIGURES:

https://bit.ly/41Sm05N

In this episode, Jordan Ross sits down with Eddie Maalouf, founder of Bad Marketing, to unpack how he scaled his digital marketing agency from his mom’s basement to $20M in revenue.

Eddie breaks down the real challenges agency owners face when growing past the early stages — including hiring the right people, building systems that scale, and avoiding founder burnout.

He shares how implementing a profit-sharing model transformed team performance, accountability, and retention, while allowing him to step back from day-to-day execution.

The conversation also dives deep into personal branding as a growth lever, why most agencies struggle to attract top-tier talent, and why sustainable agency growth comes down to mastering two core acquisitions: talent and clients.

This episode is a must-listen for:

Digital marketing agency owners stuck at a growth ceiling

Founders hiring their first leadership team

Agencies exploring profit sharing or incentive structures

Operators building long-term, scalable businesses

⏱️ Podcast Chapters

– From Zero to $20M: Eddie’s Agency Origin Story

– Building a Scalable Agency Structure

– Profit Sharing, Talent Acquisition & Client Growth

Eddie's LinkedIn - https://www.linkedin.com/in/eddie-maalouf/

Eddie's website - http://www.badmarketing.com/home-li

To learn more go to 8figureagency.co

UNLOCK THE 13 SYSTEMS EVERY AGENCY OWNER NEEDS TO REACH 8 FIGURES:

https://bit.ly/41Sm05N

In this episode, Jordan Ross breaks down the most important signal of 2026 for marketing agencies: Y Combinator, the world’s top startup accelerator, is now investing in AI-native agencies.

This episode unpacks why YC’s move into the agency world is not just surprising but a clear signal that the industry is about to be fundamentally reshaped.

Jordan walks through:

- What it means to be an AI-native agency (not just using AI tools)

- Why AI-native agencies will dominate the next 3–5 years

- The difference between AI-enhanced and AI-powered service models

- How VC-backed founders with deep engineering talent will outscale traditional operators

- Why custom internal IP (not public tools) will define the next 8- and 9-figure agency brands

He also explores why most current agencies, despite using ChatGPT or automation tools, aren’t anywhere near “AI-native,” and why those who ignore this shift may not survive the next wave of innovation.

Whether you're at $1M ARR or already at 8 figures, this is a must-listen if you care about margins, scale, and defensibility in the AI era.

Chapters:

— Intro: Why YC’s Latest Move Matters

— Who YC Has Funded (and Why That’s Relevant Now)

— What “AI-Native” Really Means (and Why You’re Probably Not One)

— Why This Will Reshape the Entire Marketing Services Industry

— How VC-Backed Agencies Will Outspend and Outbuild Everyone

— What You Must Build If You Want to Compete in 2026–2028

— The New Playbook: Custom IP, Internal Tools, and Service-as-Software

— Closing: What You Need to Do Right Now to Avoid Getting Left Behind

To learn more go to 8figureagency.co

UNLOCK THE 13 SYSTEMS EVERY AGENCY OWNER NEEDS TO REACH 8 FIGURES:

https://bit.ly/41Sm05N

In this episode, Jordan Ross sits down with Azim Nagree, Head of M&A at Herringbone, to break down how digital marketing agencies can scale, exit, and thrive through strategic acquisitions.

They unpack how Herringbone evaluates agencies, why some founders choose to join a platform instead of selling outright, and what happens after an acquisition. Azim shares candid insights into the most common challenges agency owners face—burnout, growth ceilings, and operational complexity—and how the right M&A structure can unlock long-term upside instead of a short-term exit.

The conversation also explores the future of agency platforms, including how AI will be integrated into agency operations, why specialisation by vertical matters, and what founders should be thinking about now if they want to be acquisition-ready in the next 12–36 months.

This episode is a must-listen for:

Digital marketing agency owners considering an exit

Founders curious about roll-ups and platform models

Operators thinking about AI, scale, and long-term leverage

⏱ Podcast Chapters

– Introduction to M&A in Digital Marketing

– Herringbone’s Focus and Acquisition Strategy

– Why Agencies Choose to Join a Platform

– What Happens After an Acquisition

– The Team and Resources Behind the Platform

– Long-Term Vision for Agency Platforms

– The Role of AI in Agency Operations

– Closing Thoughts and What’s Next

To learn more go to 8figureagency.co

Azim's LinkedIn: https://www.linkedin.com/in/azimnagree/

Azim's company: https://www.herringbonedigital.com/

UNLOCK THE 13 SYSTEMS EVERY AGENCY OWNER NEEDS TO REACH 8 FIGURES:

https://bit.ly/41Sm05N

In this episode, Jordan Ross sits down with M&A leaders Matt Bodnar and Tom Shipley to unpack how digital marketing agencies can use mergers and acquisitions as a true force multiplier for growth.

They discuss why agencies should operate like holding companies to boost valuation, how multiple expansion accelerates wealth creation by acquiring businesses at lower multiples and rolling them into a higher-multiple entity, and the foundational principles behind successful M&A—from resourcefulness and smart leverage to risk mitigation and the power of strong networks.

Matt and Tom also break down the “Buy Then Build” playbook, sharing practical strategies for sourcing targets, structuring deals, and uncovering hidden value within smaller service businesses.

The episode wraps with an inside look at DealCon, their upcoming event designed to help founders master deal sourcing, offer structuring, and acquisition-driven scaling.

A must-listen for agency owners ready to grow beyond services and build scalable, acquisition-powered companies.

Chapters:

— Introduction: Why M&A Matters for Agency Growth

— Understanding M&A Philosophy & Real Use Cases

— The Power of Multiple Expansion

— The M&A Playbook & DealCon Overview

— Risk Mitigation & Smart Deal Structuring

— Closing Thoughts & Where to Learn More

To learn more go to 8figureagency.co

Reach Tom @ tshipley.com

Reach Matt @ mattbodnar.com

UNLOCK THE 13 SYSTEMS EVERY AGENCY OWNER NEEDS TO REACH 8 FIGURES:

https://bit.ly/41Sm05N

In this episode, Jordan Ross sits down with Jason Shafton, founder of Winston Francois, to unpack how to build a modern marketing agency holding company in the age of AI. From automating agency operations to diversifying revenue through holding structures, they break down what it takes to lead in a world where AI is no longer optional — it's the new baseline.

Jason shares how he went from leading growth at Google to building a future-ready consultancy using AI-powered systems, automation strategies, and multi-agency scaling models. If you're a PE-backed founder, agency operator, or just AI-curious, this episode dives into tactical, financial, and strategic shifts needed to stay competitive over the next 3–5 years.

Whether you're searching for insights on AI for agency growth, automation in client delivery, or diversification through holding companies, this episode is a blueprint for the next generation of agency leadership.

Chapters:

1. Jason Shafton’s Journey: Google to AI Consultancy
2. Evolving Winston Francois: From Strategy to Automation
3. Marketing Agency Holding Companies: Structures & Diversification
4. AI Systems for Operational Efficiency
5. Tactical Upgrades for Agency Ops
6. What the Future of Agencies Looks Like in an AI-Driven World
7. Long-Term Thinking: Legacy & Financial Strategy

To learn more go to 8figureagency.co

Reach Jason at :

Linkedin - https://www.linkedin.com/in/jasonshafton

Winston Francois - https://wf.team/pod

Frank Growth - https://frankgrowth.com

UNLOCK THE 13 SYSTEMS EVERY AGENCY OWNER NEEDS TO REACH 8 FIGURES:

https://bit.ly/41Sm05N

In this episode, Jordan Ross sits down with Andy Sulhoff, founder of Lodestone Collective, to break down how custom AI systems (not just “vibe-coded” zaps and tools) are becoming the core competitive advantage for performance agencies.

Andy shares why he bet early on custom AI development with 8 Figure Agency, how they’re building an internal “AI brain” on top of their data using an MCP server, and how that’s already saving 2–3 hours per client, per week across each pod.

They dig into the difference between stacking brittle automations vs. building on a proper data layer, how Lodestone is using AI to power Slack-based reporting, Google Ads performance monitoring, discussion guides, and follow-up workflows, and why Andy believes agencies only have a 1–3 year window to build real IP before the market catches up.

If you run a digital marketing or media-buying agency and you’re serious about capacity, margins, and defensible IP going into 2027–2028, this is the blueprint.

Chapters & Timestamps

— Why Custom AI Will Decide Which Agencies Survive

— What Lodestone Collective Does & Why AI Was a No-Brainer

— Vibe-Coded AI vs. Real Data Foundations

— Capacity, Not Just Productivity: Handling 50 Clients Instead of 15

— Inside Lodestone’s AI-Powered Reporting & Slack Performance Hub

— Profit, Flexibility, and Keeping Talent Happy

— The AI Product Roadmap: Reporting, SEO, CRO & Conversion Gains

— People, Process, (Silent) IP: Building a Real Moat With AI

— The Innovator’s Curve & Why Waiting Is Dangerous

— Final Advice & Where to Find Andy

To learn more go to 8figureagency.co

Reach Andy on - https://golodestone.com/

SYSTEMS EVERY AGENCY OWNER NEEDS TO REACH 8 FIGURES:

https://bit.ly/41Sm05N

In this episode, Jordan Ross sits down with Jeff Shannon, co-founder of Pilothouse, an eight-figure performance digital marketing agency serving e-commerce and DTC brands.

Jeff breaks down how they went from affiliate media buyers to building one of the most influential DTC media engines in the space—combining an agency, a newsletter, and a podcast into a single growth flywheel.

If you run a digital marketing agency and you’re thinking about newsletters, media, performance-based pricing, or how to position for AI without burning millions on tools, this conversation is a blueprint.

⏱ Chapters

Chapters & Timestamps

– Cold Open & Intro

– Who Is Jeff & What Is Pilothouse?

– From Affiliate Arbitrage to Content-Led Growth

– Proving the Newsletter & Going All-In

– 150K Subs & Negative CAC for the Agency

– Would Jeff Start a Newsletter in 2025?

– Jordan’s Newsletter & Monetization Strategy

– When Sponsorships Make Sense (and When They Don’t)

– Multiple Legs on the Stool: Beyond Newsletters

– The Three Biggest Growth Levers to 8 Figures

– Performance-Based Pricing & Paying Talent Big Upside

– Risk-Reward Models & the New Agency Standard

– Life as a Non-Day-to-Day Founder

– Founders vs Operators: Knowing Your Seat

– How Pilothouse Is Positioning for AI (2026–2027 View)

– Move Fast or Get Left Behind

– Where to Find Pilot House, DTC, and Join Agency

– Outro & Event Plug

To learn more go to 8figureagency.co

To reach Jeff - https://www.pilothouse.co/

UNLOCK THE 13 SYSTEMS EVERY AGENCY OWNER NEEDS TO REACH 8 FIGURES:

https://bit.ly/41Sm05N

In this episode, Jordan Ross sits down with Mark Mei, founder of DAHAS Digital, to break down one of the hardest challenges in scaling an agency — maintaining quality while growing fast.

They unpack why quality tends to drop as agencies expand, how leaders can structure workflows for accountability, and what systems help ensure client satisfaction at scale. Mark shares how his team at DAHAS Digital uses layered QA checks, feedback loops, and clear ownership across each stage of client work to maintain excellence without slowing down growth.

Whether you’re leading a 5-person boutique or managing a 50-person team, this episode gives you a roadmap for building operational resilience without losing creative edge or client trust.

🕒 Chapters

– Introduction to Mark Mei and DAHAS Digital

– Ad Spend and Marketing Funnel Insights

– Future Plans and Aspirations

– The Biggest Challenge: Maintaining Quality as You Scale

– Building a Workflow Where Everyone Owns QA

– Creating Feedback Loops and Training for Quality

– Why Quality Assurance Protects Client Retention

– The Client-Centric Growth Mindset

– Closing Thoughts and Key Lessons

To learn more go to 8figureagency.co

To reach Mark Mei go to www.dahausdigital.com

In this end-of-year recap episode, I break down one of the most intense and defining years of my life and business.

I cover the lessons learned from losing my home, what that experience forced me to reevaluate about life and business, and why it accelerated a full rebrand of our agency into what we believe will become the world’s leading AI consulting firm for agencies.

I also share early details about our 2026 live event, what it’s designed to solve for agency owners, and why the next phase of agency growth will be driven by AI, systems, and leverage—not more people, more clients, or more chaos.

This episode is about resilience, reinvention, and where agencies must evolve next.

What We Cover in This Episode

My honest end-of-year business and life recap

What losing my home taught me about risk, leverage, and priorities

Why adversity forced a faster, clearer rebrand

The decision to reposition into AI consulting for agencies

How AI will change agency operations, margins, and team structure

Why most agencies will fall behind in the next 12–24 months

The vision and intent behind our 2026 live event

What agency owners actually need now (and what they don’t)

Building a business that survives chaos, shocks, and volatility