Podcast Overview
You start as a freelancer. Just you, a laptop, and a search ranking obsession. Fast-forward a few years: your agency is pulling in $10 million a year. Offices in LA, Vegas, the Philippines. A 100-person global team.
Sounds like a dream, right?
Jason Hennessey
Jason shares his incredible journey from early freelance SEO gigs to building Hennessey Digital, a powerhouse agency serving major U.S. law firms and generating millions in revenue.
In this episode of eCom@One with Richard Hill, Richard interviews Jason Hennessey—entrepreneur, SEO strategist, author, and speaker. They dive into how Jason scaled his business organically, starting with a Craigslist ad and eventually building a distributed team across continents.
He breaks down how to hire for creative freedom, why personal branding can open doors faster than cold emails, and how SEO is really just a form of storytelling—done with strategy.
Jason also opens up about burnout, starting over, and the mindset shifts that took him from six figures to eight. Whether you’re an agency owner, SEO nerd, or just love a good business build-up story—this one’s for you.
The episode is packed with smart, honest insights on growth, team-building, niching down, and trusting the long game.
Topics Covered
Topics Covered:
00:00 Scaling Agencies: Insights from Jason Hennessey
03:29 Leading Law SEO Agency Insights
08:30 Scaling Business by Hiring Experts
12:22 Documenting Time and Task Management
15:04 Hiring and Business Culture Insight
17:05 “Building a Team-First Culture”
19:59 Hackathon Innovation: HD Translate
25:24 Adapting SEO with AI Innovation
26:32 “Personal Branding for Agency Success”
29:45 “Book as Unique Selling Point”
33:01 Navigating Burnout and Business Challenges
36:29 Balancing Work and Personal Life
39:43 Email Management and Availability
43:07 “My Grandfather, My Greatest Mentor”
46:26 “Balancing Growth and Risk”