Moving to Israel? This Is the Mindset You Need to Thrive | Eli Freedman, Founder of Cork & Cellar

From Shtark Tank with Yaakov Wolff by Yaakov Wolff.

• Published: Mon, 01 Dec 2025 05:15:00 GMT
• Duration: 00:44:12
• Audio: https://anchor.fm/s/e45c8048/podcast/play/111928961/https%3A%2F%2Fd3ctxlq1ktw2nl.cloudfront.net%2Fstaging%2F2025-10-30%2F413474749-44100-2-fdfcd9c81be9d.mp3
• Page: https://podcasters.spotify.com/pod/show/yaakov-wolff/episodes/Moving-to-Israel--This-Is-the-Mindset-You-Need-to-Thrive--Eli-Freedman--Founder-of-Cork--Cellar-e3bma61
• TorahApp: https://torahapp.org/share/p/3P_shtark_tank/e/00278204-3670-4779-93f0-24e44f030d85

Aliyah isn’t just a flight and a moving truck.
It’s a total reset of how you think about parnassah, gashmiyus, bitachon, and what “quality of life” actually means.

In this episode, I sit down with Eli Freedman, founder of Cork & Cellar Wine Club, to talk about what it really takes to move to Israel and stay – spiritually, emotionally, and financially.

Eli shares how he:

• Went from Boston → Wall Street → Montreal → Beit Shemesh

• Had zero interest in Aliyah… until COVID, a grandchild in Israel, and a breaking point in Canada

• Sold his house and business with no Plan B so he couldn’t run back

• Went through the “Eretz Yisrael car wash” – a painful but powerful reset of his gashmiyus and bitachon

• Rebuilt his career from scratch, launching Cork & Cellar, a boutique Israeli wine club for U.S. customers

• Found a real rav and kehillah after years of feeling disconnected

• Built a serious morning learning seder and finished Shas multiple times while running a business

We also talk about:

• Why you must come with a realistic parnassah plan – and still expect it to break

• The mindset shift from “keeping up with the Joneses” to “being happy with less but living with more”

• How living in Eretz Yisrael forces you to actually use your emunah and bitachon, not just talk about them

• The balance between enjoying good wine and not turning gashmiyus into your ikar

About our guest:
Eli Freedman is the founder of Cork & Cellar Wine Club, connecting small Israeli wineries with wine lovers in the U.S., and helping boutique winemakers who would never make it to American shelves. He lives in Beit Shemesh with his family.

Check out https://www.corkandcellar.net/club

If this episode gave you chizuk or clarity about Aliyah and mindset,
please follow Shtark Tank, leave a rating, and share it with a friend who’s thinking about moving to Israel.