In this compelling episode, we explore the remarkable 29-year journey of Michael Shapiro, who founded Ketubah.com in 1996 and has successfully navigated the ever-changing landscape of e-commerce. From his early career setbacks to building a thriving business around the ancient Jewish tradition of the Ketubah (marriage contract), Michael shares invaluable insights about resilience, innovation, and the art of adapting traditional businesses for the digital age.

Guest Bio

Michael Shapiro is the founder and visionary behind Ketubah.com, one of the oldest continuously operating e-commerce sites, launched in 1996. With a background in history, political science, and brand management at Procter & Gamble, Michael left the corporate world to build a business that bridges ancient Jewish traditions with modern technology. He leads a team of nine and has recently authored "Ketubah Renaissance," a coffee table book chronicling the modern revival of Jewish marriage contracts.

Business Evolution & Technology

• Platform Journey: HTML → ColdFusion → WordPress/WooCommerce
• AI Integration:
  • HebrewNamer.com: AI-powered Hebrew name suggestion tool
  • AI Ketubah text writing assistant with multiple styles (traditional to Shakespearean)
  • Behind-the-scenes order processing automation
• Building custom functionality on standardized platforms

Leadership & Team Building

• Transitioning from hands-on founder to visionary leader
• Building a team of 9 that brings their own innovative ideas
• Working with a Director of Operations (EOS-style integrator role)
• The joy of having team members contribute creative solutions

Creative Projects

• "Ketubah Renaissance" Book: Coffee table book documenting 60+ years of modern Ketubah artistry
• 12-year journey from initial idea to publication
• Working with demanding editors and the growth process
• Publishing with Jewish Publication Society, releasing August 1st

Notable Quotes

"It's not just they're implementing my ideas, they're bringing their ideas. And that's something that has been a long-term goal for me."

"I have a very well-developed creative side... connecting the dots in ways that perhaps other people haven't."

"Writing the book was a labor of love and sometimes a labor of hate."

Connect with Michael Shapiro

• Website: Ketubah.com
• Email: info@ketubah.com
• Instagram: @Ketubah.com
• LinkedIn: Michael Shapiro
• Book Pre-order: "Ketubah Renaissance" on Amazon

Chapters

00:00
Introduction to Michael Shapiro and Ketubah

02:24
Michael's Journey to Entrepreneurship

07:43
Understanding Ketubah: The Jewish Marriage Contract

09:33
The Creative Vision Behind Ketubah

13:15
Leveraging AI in Ketubah and Hebrew Namer

14:39
Seasonality and Trends in the Ketubah Business

15:42
Exploring EOS and Business Strategies

16:44
The Ketubah Renaissance Book Project

19:06
E-commerce Evolution and Platform Migration

21:53
Closing Thoughts and Shameless Plug

This has been produced in cooperation with Talk Commerce

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