How to Create an Aspirational Yet Authentic Brand

They discuss balancing aspirational visuals with everyday authenticity and ensuring photos, tone, and content reflect real founder personality.

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Episode notes

A prettier logo won’t fix a broken offer. In this episode, I sit down with creative director and brand strategist Rachel Pesso, and we talk about when to rebrand, what actually moves revenue, and how to build a brand that matches the depth of your work. Rachel breaks down the signs you’re out of alignment, the clarity you need before you touch fonts and colors, and the user-experience shifts that turn your website from “pretty brochure” into a conversion tool. We also riff on serial content, photo shoots that elevate your positioning, and creating a through-line when you’re a multifaceted founder. Get ready to learn how to design a brand that not only looks incredible but feels like the next level version of you.

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HIGHLIGHTS

00:00 Meet Rachel Pesso, creative director, brand designer, and my long-time collaborator.

08:30 Why brand evolution is normal and necessary.

12:00 How to start building cohesive branding as a beginner.

18:00 How to know when your brand is out of alignment.

25:00 The brand alignment method for bridging the gap between who you are and how your brand shows up.

33:00 How I created a cohesive look between all my brands.

40:00 How your visual identity affects confidence and momentum.

45:00 Why “niching down” isn’t always the answer for visionary founders.

46:00 The biggest mistakes that cost entrepreneurs money when rebranding.

50:00 How do you keep your creative projects and clients on track?