Jason Hennessey’s entrepreneurial journey began when he shared his impressive results in e-commerce and affiliate marketing during a presentation. The audience—mostly lawyers—were so impressed that several approached him afterward, asking if he could help them achieve similar success. Though he hadn’t considered starting an agency before, he left the room that day with seven business cards and the beginnings of $30,000 per month in recurring revenue. That single, 45-minute presentation marked the start of his agency and set him on the path to building a thriving business.

In today’s episode, Richard and Jason explore Jason’s journey from his early days as a self-taught SEO freelancer to building a global team of over 130 people. Along the way, you’ll hear insights on the power of niching down, the importance of agency culture, and how to transition from a lifestyle business to a scalable operation. Jason also shares advice on hiring key leadership roles, leveraging executive assistants to maximize impact, and integrating AI and innovation into agency processes.

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"