July 22, 2025

EP. 39 - Diving Deep with Lana Rafaela

EP. 39 - Diving Deep with Lana Rafaela
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Season 1

In this episode of Retained Trust, Karl Hughes speaks with Lana Rafaela, founder at Cherry Red Content, a boutique agency focused on tailored content marketing solutions for early-stage, bootstrapped startups. Lana shares her experiences transitioning from freelancing and marketplace management at Contently to starting her own agency, highlighting the benefits of personalized client relationships. They explore the evolving landscape of product marketing, the critical role content plays within it, and why founders should embrace their unique perspectives when marketing their companies. Lana offers practical guidance for startups struggling with pre-product-market fit marketing strategies and discusses the impact and role of AI in modern agency operations. 

Key Points From This Episode: 

[00:00:27] Lana's memorable dive into a WWII bomber wreck near Croatia. 

[00:02:18] Overview of Cherry Red Content and its specialized approach. 

[00:03:27] Ideal clients: Bootstrapped startups seeking targeted growth. 

[00:04:12] Benefits and challenges of working with hands-on founders. 

[00:06:40] Understanding product marketing and its role in SaaS. 

[00:09:27] The relationship between product marketing and content. 

[00:10:07] Lana’s insights from working at Contently and transitioning to entrepreneurship. 

[00:13:40] Acquiring clients through LinkedIn, referrals, and community engagement. 

[00:14:50] Challenges and shortcomings of using Google Ads for client acquisition. 

[00:16:45] Cherry Red’s sales approach: consultative and strategic. 

[00:18:22] Advice for early-stage founders hesitant about marketing. 

[00:19:53] Key lessons from the book "The Mom Test" about validating startup ideas. 

[00:21:58] Differences between generating and capturing market demand. 

[00:23:25] Coaching founders through marketing fears and mental roadblocks. 

[00:26:18] Lana’s involvement and her team's structure at Cherry Red. 

[00:28:00] How AI tools are used effectively within Cherry Red’s workflows. 

[00:31:08] Moving toward entertainment-driven, engaging B2B content. 

[00:32:26] Challenges in harnessing founders' insights and keeping up with trends. 

[00:34:12] Hiring strategy: prioritizing entrepreneurial experience over specific hard skills. 

[00:36:34] Lana’s satisfaction in solving client problems and creating positive impact. 

[00:37:47] Challenges of entrepreneurship: constant context switching and prioritizing tasks. 

[00:39:30] Book recommendation: "The McDonaldization of Society" and its implications for agency work. 

[00:41:32] Finding a balance between standardization and creative flexibility. 

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