In this episode, Terresa Zimmerman sits down with Brian Lipstein, founder and CEO of Henry A. Davidsen, a Philadelphia-based custom menswear company known for delivering more than just great suits. Over the creation of a perfectly formed, ice ball for a glass of Macallan, Brian shares the unique experience his clients enjoy—complete with a personalized whiskey bar—and the journey he took to build his business from a University of Pennsylvania venture program to nearly 20 years of success.

Brian’s story is filled with passion, from learning the art of tailoring to providing men with an unmatched customer experience, grounded in education and authenticity. He explains how his father, who once celebrated the rise of business casual, became his first test subject for a custom suit and the surprising transformation that followed. Brian talked about the philosophy behind his proven process, the power of a well-fitted garment, and how custom clothing can boost confidence, performance, and trust.

The conversation touches on everything from business growth challenges to the importance of building genuine client relationships, and the future of Henry A. Davidsen, including plans for expansion and creating a scalable yet personalized client experience across multiple locations.

Brian also shared Henry A. Davidsen’s core values and are represented by the acronym R.E.A.L.:

1. Be Reputable: Uphold integrity, credibility, respect, and trustworthiness in every action. It’s about being reliable and maintaining a strong reputation through every client interaction.

2. Be Extraordinary: Focus on creating exceptional, high-touch experiences that go beyond the ordinary. Every detail matters in delivering a personalized and memorable experience for clients.

3. Be Authentic: Encourage clients to be their true selves and reflect that authenticity through their clothing. Henry A. Davidsen aims to help people feel comfortable in their skin and align their outward appearance with who they truly are.

4. Be Learned: Continuously seek knowledge and education, both for the team and clients. This value is about growing, learning from experiences, and using that knowledge to improve services and educate others.

Key Takeaways:

-Brian’s journey from college incubator program to 19 years of tailoring excellence.

-How Henry A. Davidsen delivers a luxury experience with custom whiskey bars and personalized consultations.

-Why fit, fabric, and personal style matter beyond the brand label.

-Brian’s approach to scaling his business without losing its core values of authenticity and client experience.

Whether you're interested in custom menswear, entrepreneurship, or the importance of community-driven business, this episode is full of valuable insights.

Featured in this episode:

Henry A. Davidsen

Website: https://henrydavidsen.com/

Instagram: @henrydavidsen

Blog: https://henrydavidsen.com/blog/

Connect with Brian Lipstein:

LinkedIn: https://www.linkedin.com/in/brianlipstein/

Other Mentions:
Entrepreneur’s Organization -
https://hub.eonetwork.org/

(BOOK) Unreasonable Hospitality - Link

(BOOK) Know What Matters: Lessons from a Lifetime of Transformations by Ron Shaick - Link

Connect with Us:

Main Street Matters Podcast:

Website: www.mainstreetmatters.co

Instagram: https://www.instagram.com/mainstreetmatters1

LinkedIn: https://www.linkedin.com/company/main-street-matters

YouTube: http://www.youtube.com/@MainStreetMatters_MSM

Host - Terresa Zimmerman:

https://www.linkedin.com/in/terresachristensonzimmerman