DiscoverSecond Bite PodcastBootstrapped to Boardroom: How Jason Hennessey & Trinity Hunt Will Impact Legal Marketing
Bootstrapped to Boardroom: How Jason Hennessey & Trinity Hunt Will Impact Legal Marketing

Bootstrapped to Boardroom: How Jason Hennessey & Trinity Hunt Will Impact Legal Marketing

Update: 2025-06-19
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Jason Hennessey is the CEO of Hennessey Digital, a digital marketing agency specializing in legal marketing using a holistic approach. In his role, he grew the small consultancy to a multimillion-dollar business that made the Inc. 5000 list for six consecutive years. As an entrepreneur, internationally recognized SEO expert, author, speaker, podcast host, and business coach, Jason has scaled and sold multiple businesses. He has been reverse-engineering the Google algorithm since 2001. 

In this episode…

When considering outside capital to kickstart growth, founders often turn to private equity. How can you evaluate private equity opportunities while protecting your company’s culture, team, and long-term vision?

Jason Hennessey, CEO of Hennessey Digital, shares how he scaled his legal SEO agency by partnering with private equity. With host Todd Taskey, Jason explains why he partnered with Trinity Hunt, the importance of assembling a strong leadership team, and how he adapted the company’s culture.

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Bootstrapped to Boardroom: How Jason Hennessey & Trinity Hunt Will Impact Legal Marketing

Bootstrapped to Boardroom: How Jason Hennessey & Trinity Hunt Will Impact Legal Marketing

Todd Taskey, Jason Hennessey