In this episode of Retained Trust, host Karl Hughes speaks with Derek Delost, who shares his path from digital marketing burnout to agency ownership through the acquisition of DotYeti. Derek explains why starting from scratch wasn’t the right fit for him, how he navigated the risks of buying a business, and the realities of leading a team after a transition. He dives into the emotional and strategic challenges of the process—from deal structure to team restructuring—and how he’s positioning DotYeti to thrive in an evolving creative market. A must-listen for agency operators and aspiring business buyers alike.

Key Points From This Episode:

[00:00:50] Derek introduces DotYeti and its flat-rate graphic design model.

[00:02:02] Derek’s early career in digital marketing and creative collaboration.

[00:04:06] Burnout, tech transitions, and reevaluating life goals post-2020.

[00:05:07] How two books reshaped Derek’s view on entrepreneurship.

[00:07:53] Struggles with freelancing and why zero-to-one wasn’t appealing.

[00:10:14] The emotional cost of starting from scratch vs. buying a business.

[00:13:46] Why Derek originally didn’t want an agency—and what changed.

[00:15:18] Exploring “eternally profitable” service businesses.

[00:17:31] Why industry alignment and passion matter more than spreadsheets.

[00:19:24] Reframing the agency model as timeless, not obsolete.

[00:21:08] Building broker relationships that surfaced DotYeti early.

[00:23:03] LOIs, NDAs, and the initial deal structure.

[00:25:33] De-risking: financing, legal teams, and reputable intermediaries.

[00:28:06] The challenge of bank financing as a Canadian buyer.

[00:33:22] The importance of alignment with the selling founders.

[00:36:02] The risk of treating the transaction as purely transactional.

[00:37:39] “Burning the boats”: The emotional cliff of closing the deal.

[00:40:11] Breaking the news to a 40-person remote team.

[00:44:08] The CEO seat: urgency, decision fatigue, and communication.

[00:47:23] Navigating transparency and emotional weight in leadership.

[00:48:09] Strategic changes: moving away from “unlimited” design model.

[00:50:06] Restructuring the team to support higher-quality offerings.

[00:52:09] Finding DotYeti’s position in a saturated, AI-impacted market.

[00:54:10] Why service businesses can’t be truly passive income.

[00:55:06] AI isn’t a threat—it’s a tool in skilled hands.

[00:58:19] Book recommendation: How Brands Grow by Byron Sharp.

Links:

• Derek Delost on LinkedIn: https://www.linkedin.com/in/derekdelost
• DotYeti: https://www.dotyeti.com/book-demo
• Karl Hughes on LinkedIn: https://www.linkedin.com/in/karllhughes
• Production and editing by The Podcast Consultant: https://thepodcastconsultant.com