In this Office Hours Live edition of Send This to Your CEO, Tyler Jacobson, Matt Gillespie, and Aaron Rosenbluth tackle a question that many B2B leaders wrestle with: When is it okay to rush a brand or rebrand?

From exploring the impact of AI and rapid market shifts to identifying when to prioritize strategy over visual identity, this energized discussion uncovers the nuances of building a brand at high speed without sacrificing authenticity or connection. The team debates the pros and cons of expedited branding in both B2B and B2C contexts — touching on public brand backlash (looking at you, Cracker Barrel) and the importance of tone, positioning, audience insight, and even booth design at trade shows.

Whether you’re a startup sprinting to market or an established brand navigating a merger or market shift, this episode offers sharp insights — along with a few laughs — to guide your next move.