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What happens when a regulatory attorney trades Wall Street stress for barber-chair swagger? Jessica shows how instinct, culture, and system design built a luxury grooming brand that outlasted the copycats.

Summary:

Jessica, founder of Mad Men Barbershop, shares how she turned gut calls, culture, and brand discipline into a multi-location grooming experience that grew stronger through competition and COVID. We unpack instinct-based decision-making, the split between creative vision and operational discipline, scaling culture across shops, and how social media keeps both clients and staff accountable. Jessica also opens up about writing Pivot And Slay and Selfish Is A Superpower, and speaks candidly about ambition, parenting, identity, and the practical hiring and vibe-setting tactics that keep her team aligned. This episode is all about building a lifestyle brand that stands the test of time—no matter who tries to copy it.

🎥 Watch the full episode on YouTube:
https://www.youtube.com/@TheSmallBusinessSafari

💡 GOLD NUGGETS 

• Founding Mad Men Barbershop as a lifestyle brand, not a commodity
 • Why instinct often beats perfect plans in early entrepreneurship
 • How Jessica handled copycats—and why doubling down on culture works
 • COVID shutdown survival decisions and reopening timing
 • Scaling vibe, expectations, and accountability across multiple locations
 • Writing Pivot And Slay and Selfish Is A Superpower
• How ambitious women navigate identity, parenting, and business growth
• Hiring, training, and culture-setting that keeps standards high

🔗 Guest Links

• Website: https://pivotandslay.com

https://www.madmenbarbershop.com
 • Instagram: @pivotandslay
 • LinkedIn: linkedin.com/in/thejessicadennehy-7b629a201
• Books: Pivot And Slay & Selfish Is A Superpower (Amazon)

🌍 Follow The Small Business Safari

• Instagram | @smallbusinesssafaripodcast
 • LinkedIn | linkedin.com/in/chrislalomia
• Website | https://chrislalomia.com

thetrustedtoolbox.com 

From the Zoo to Wild is a book for entrepreneurs passionate about home services, looking to move away from corporate jobs. Chris Lalomia, a former executive, shares his path, discoveries, and tools to succeed as a small business owner in home improvement retail. The book provides the mindset, habits, leadership style, and customer-oriented processes necessary to succeed as a small business owner in home services.