Hi everyone! Welcome back to another episode of The Chai on Life Podcast. I’m Alex Segal and today, we have Debbie Sassen, business coach, money mentor and host of the Jewish Entrepreneur Podcast joining us. She helps established entrepreneurs scale from six to seven figures with high-ticket offers, leveraged business models, and smart CEO strategies—all in alignment with Jewish values.

Debbie is the go-to expert for business owners ready to charge more, raise their prices, and sell high-ticket offers with confidence—without feeling pushy or sleazy. She believes that money is intimately woven into every part of business, and that clearing money blocks makes growth, marketing, and sales infinitely easier.

Her signature coaching program, Wired for Wealth, helps entrepreneurs scale sustainably with her 10-step leverage plan, Power of 1 method, and Sacred Sales Conversation process. Through her coaching, clients master their CEO mindset, leverage their time, and implement simple systems to create consistent $20K-$50K months—without sacrificing their faith, family, or freedom.

Debbie believes that no woman - or man - should undercharge, undersell, or dim their light to build financial sustainability for their family.

She is also, the mother of eight children bli ayin hara, so she has a LOT to share with us. I was really excited to dig into a conversation about money because I feel like it’s a topic not often discussed. Even with close friends it can be awkward or weird to go into let alone people you know less well yet it’s such an important and vital part of our lives. It’s also one that a lot of people have a lot of feelings around. We all have attachment styles to money the same way we do with relationships and it’s something we have to manage and encounter multiple times a day.

In the Jewish world, there are extra expenses — Shabbos, kosher food, Pesach of course which is rapidly on its way, two sets of dishes, tuition, generally having more kids and of course so much more.

In this episode we speak about:

-The relationship Debbie had growing up to money and how that has developed and changed into how it is now

-Women taking time off of a career for motherhood and how that impacts her involvement in household finances

-Re-entering the workforce during motherhood and how so many women often underestimate themselves and their skills

-Money and marriage — how to speak about it with your husband, designate certain roles if you would like to and maintain and gauge that trust and partnership in the relationship

-We talk about spirituality within all of this — how Hashem comes into the picture with work, money and giving and how that all can contribute to a more secure attachment with our finances

…and SO MUCH MORE

Debbie is a wealth of knowledge — pun intended — and honestly, we cover so much and also just skimmed the surface. She has a ton of additional resources available which are all included in the show notes if you’d like to learn more or get in touch with her.

Website: https://debbiesassen.com/

Podcast: The Jewish Entrepreneur Podcast https://debbiesassen.com/podcast/

Book, The $1K Investor: Simple Smart Steps to Start Investing with $1K or Less https://debbiesassen.com/book (links to Amazon)

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

Instagram: @debbiesassen

Facebook: https://www.facebook.com/debbiesassencoaching

 Free resource: Your Money Mindset Workbook: https://debbiesassen.com/mindset/