In this episode, we sit down with Cassidy Clemmer to talk about the real side of building a creative career and why consistency matters more than chasing perfect content.

From photography school to brand campaigns, Cass shares how shadowing other photographers, building relationships, and staying authentic has helped her grow her business. We dive into imposter syndrome, the pressure creators feel to show up online, and the challenge of balancing personal identity with professional content.

This conversation is packed with insight for small businesses, brands, and creators trying to build stronger content without feeling forced or fake.

Inside this episode:

• why consistency always wins over perfection
• what brands actually look for when hiring creators
• how spec work and passion projects open doors
• building trust through content instead of chasing trends
• navigating imposter syndrome while growing your business

If you’re creating content, hiring creatives, or trying to show up online in a more honest way, this episode will give you practical takeaways you can actually use.

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A podcast about what really goes on behind the scenes of building brands, businesses, and personal platforms.

We talk marketing, content, branding, community, and the uncomfortable middle between idea and execution.
Built for founders, creators, and business owners who want honest conversations, not recycled advice.


Hosted by Matt and Olivia. Audio-only for now. New episodes regularly.

Listen & subscribe
→ Apple Podcasts
→ Spotify

Follow along
→ Instagram:
@Mattortlieb_
@oliviamckerrow
@ortliebmedia