In this episode of Retained Trust, host Karl Hughes speaks with Greg Heilers, co-founder of Jolly SEO, an agency focused on earned link building and media placements. Greg shares his unconventional entrepreneurial journey, from volunteering around the world to launching multiple agencies and eventually building Jolly SEO into a productized service. The conversation examines lessons learned from early business failures, the value of partnerships, and the challenges of running service businesses through rapid technological change. Karl and Greg also analyze how generative AI is reshaping SEO, content marketing, and outreach—affecting workflows, team structures, and the broader digital marketing ecosystem.

Key Points From This Episode:

[00:00:00] Introduction to the Retained Trust podcast and guest Greg Heilers of Jolly SEO.

[00:00:49] Greg explains Jolly SEO’s focus on earned link building and shares why he lives in China.

[00:01:38] Greg’s entrepreneurial origin story, including volunteering abroad and starting his first agency.

[00:03:43] Lessons from failed ventures, including attempts at software and early agency struggles.

[00:05:56] Why productizing services helped Jolly SEO manage client expectations and avoid revision-heavy work.

[00:07:45] How Jolly SEO connects clients with journalists and media outlets through earned media placements.

[00:09:50] Overview of link building, ghostwriting debates, and the role of media mentions in SEO.

[00:11:59] The volatility of marketing agencies and how external trends shape their growth cycles.

[00:13:02] Greg shares tactical and emotional strategies for managing the ups and downs of entrepreneurship.

[00:17:13] The benefits and challenges of running a company with a long-term business partner.

[00:20:18] Greg’s side projects, including a HARO course and exploring acquisitions of traditional businesses.

[00:24:52] How generative AI has changed workflows, delivery timelines, and pricing in agency services.

[00:25:38] Internal experimentation with AI at Jolly SEO and the cost savings achieved through automation.

[00:29:16] The leadership challenges of introducing AI to teams and helping employees adapt to new tools.

[00:32:28] The emotional difficulty of workforce reductions and the human side of running a business.

[00:36:17] How AI-generated content and mass outreach are making high-quality media placements harder.

[00:38:26] The ongoing arms race between spam filters and automated outreach tools.

[00:39:25] Discussion on AI detection tools, false positives, and challenges faced by non-native English writers.

[00:41:45] Whether AI writing has reached a plateau or will soon match high-quality human content.

[00:43:11] The future of long-form content and the rise of AI-generated summaries.

[00:45:45] Reflections on technology’s impact on attention spans and digital media consumption.

[00:47:09] Book recommendations including Think and Grow Rich, Who Not How, and Atomic Habits.

[00:49:06] Karl shares a recommendation: The Top Five Regrets of the Dying and its impact on perspective.

[00:51:43] Where to connect with Greg Heilers and learn more about Jolly SEO.

Links:

1. Greg Heilers on LinkedIn: https://www.linkedin.com/in/gregheilers/
2. Jolly SEO: https://jollyseo.com/
3. Karl Hughes on LinkedIn:https://www.linkedin.com/in/karllhughes
4. Production and editing by The Podcast Consultant:https://thepodcastconsultant.com