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June 16, 2025 30 mins
Featuring: Courtney Jason Hennessey, Hennessey Digital

In episode 115, I sit down with Jason Hennessey, internationally recognized SEO expert and CEO of Hennessey Digital. Jason shares the story of how a single talk at a legal mastermind sparked his first agency, and how he’s since scaled a powerhouse SEO firm serving top-tier law firms. We talk about niching down, the power of building a personal brand, and why delegation was key to scaling without burning out. Jason opens up about leadership, team culture, and how stepping back actually helped his agency grow faster. Plus, we dive into strategies like direct mail, personal outreach, and even outsourcing genius to level up results.

Key Bytes

• Jason Hennessy has been in SEO since 2001 and started his first agency in 2008. • He transitioned from his first agency to Hennessy Digital in 2015, focusing on law firms. • Innovative marketing strategies, like sending personalized books, helped him secure clients. • Hennessy Digital primarily serves personal injury lawyers but sees potential in other legal niches. • Building a personal brand has significantly increased response rates to his outreach. • Delegation and outsourcing are key to scaling an agency effectively. • Jason emphasizes the importance of investing in leadership and team development. • He still engages with SEO on a personal level, leveraging external expertise. • Agency culture is a priority, fostering support and recognition among team members. • Asking for help and seeking coaching is crucial for agency owners.

Chapters

00:00 Introduction to Agency Bites and Guest Background 01:04 Jason Hennessy's Journey in SEO and Agency Growth 03:55 Transitioning from First Agency to Hennessy Digital 07:00 Innovative Marketing Strategies for Law Firms 10:06 Market Potential and Niche Focus in Legal SEO 11:58 Building a Personal Brand and Leadership Structure 16:01 Scaling the Agency and Delegating Responsibilities 20:03 Passion for SEO and Outsourcing Expertise 23:05 Expanding Services Beyond SEO 24:54 Agency Culture and Team Dynamics 27:04 Personal Insights and Advice for Agency Owners

Jason Hennessey is an entrepreneur, internationally recognized SEO expert, author, speaker, podcast host, and business coach. Since 2001, Jason has been reverse-engineering the Google algorithm as a self-taught student and practitioner of SEO and search marketing.

Jason's expertise has fueled the growth and successful sale of multiple businesses, starting with a pioneering dot-com venture in the wedding industry. Serving as the CEO of Hennessey Digital since 2015, Jason's leadership has transformed a modest consultancy into a thriving eight-figure agency, earning a place on the prestigious Inc. 5000 list for five consecutive years. He is also the author of two Amazon bestsellers, titled Law Firm SEO and Honest SEO.

As a sought-after keynote speaker and a frequent guest on podcasts and webinars, Jason shares his wealth of knowledge. He contributes as a columnist to respected publications such as the Washington Post and is a regular contributor to Entrepreneur, Forbes, Inc., Newsweek, and Rolling Stone Magazine. Jason's accomplishments extend to being honored with the Gold TITAN Business Award in the Entrepreneurship, Branding, Advertising, & Marketing category, as well as being recognized as a National Law Review Go-To Thought Leader.

Jason's journey has been enriched by his experience as a United States Air Force veteran and his attainment of a Bachelor of Arts degree in Marketing from the University of Nevada, Las Vegas. Commencing his SEO career in Las Vegas and later establishing a strong presence in the legal industry in Atlanta, Jason now resides in the Los Angeles area with his wife, Bridget, and their three children.

Contact Jason on his personal website, his agency website,

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