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She Left Wall Street, Built A Brand, And Found Freedom In Small Business | Jessica Dennehy
Manage episode 522295063 series 2980277
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
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.
Chapters
1. Welcome To Small Business Safari (00:00:00)
2. Host Banter And Industry Events (00:02:30)
3. Meet Jessica Dennehy And Her Backstory (00:05:20)
4. From Debate Lover To Wall Street Attorney (00:06:55)
5. Kindness As Strategy In High-Stakes Law (00:10:40)
6. Why Start A Business While Pregnant (00:13:50)
7. Risk, Security, And The Leap (00:17:25)
8. The Reveal: Luxury Barbershops (00:21:55)
9. Building A Vibe Without A Plan (00:24:15)
10. Mad Men Aesthetic And Early Differentiation (00:27:45)
11. Roles, Strengths, And Creative-Operations Split (00:30:35)
12. Competition, Copycats, And COVID Shock (00:33:05)
13. Fight Back: Double Down On Brand (00:36:25)
14. Multi-Location Culture And Systems (00:38:15)
15. Social Media As Accountability And Story (00:41:05)
16. Writing Books To Process And Teach (00:44:05)
17. Women, Ambition, And Self-Prioritization (00:47:15)
18. Lightning Round And Personal Anecdotes (00:50:35)
19. Closing Thoughts And Sign-Off (00:57:35)
258 episodes
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