Haim Dabah is a serial entrepreneur who’s built and sold billion-dollar companies across fashion, venture capital, real estate, and healthcare.

In this episode, we break down the rise and fall of his billion-dollar brand Gitano, how he pioneered designer collaborations with mass retailers, and the mindset that’s kept him building ever since.

Help us build the Sephardic Mikveh of Gravesend: https://raisethon.com/gravesend

Book your free Pivot & Prosper strategy call with Jeff Sitt: https://jeffsitt.com

Check out Joe Shamie on Momentum: https://open.spotify.com/episode/08I7cEj8hFAjNS5ApHCWn5?si=gjSeTcwST0GctCBi96Bzog

00:00 Intro

02:14 Growing up in Israel

05:38 How the 6 Day War affected Haim’s childhood

06:40 Going to Yeshivah after moving to America

08:09 Haim’s 1st job in America

10:21 His father started a wholesale business

12:15 Stories of working with his father

14:05 Launching Gitano

14:43 “Gitano University”

16:12 “I wasn’t a good dad.”

16:36 Working With Walmart

16:51 Working for Sam Walton undercover

18:28 Sephardic Mikveh of Gravesend

19:20 Gitano’s wide-ranging wholesale approach

20:48 How Gitano set itself apart

21:37 Gitano’s unique selling points

22:42 Expanding Gitano’s product types

23:16 Challenges of surpassing $1 billion in sales

24:29 Haim’s thoughts about college

25:12 Company fails when Haim is 40 years old: what now?

26:09 Starting a new business: Regatta

28:46 Bringing Vera Wang to Kohl’s

29:44 Buying out his partner in Regatta

30:03 Selling Regatta to a $20B conglomerate

31:48 Having a boss for the first time in his life

33:48 Book a call with Jeff Sitt

34:50 Support the Morris I. Franco Cancer Center

35:44 The insane grind of building a company

36:22 Not dedicating enough time to his family

37:25 Beginning to prioritize family over work

39:08 Leaving the wholesale business after selling his company

41:03 Finding fulfillment in investing

41:48 How to identify great founders as an investor

43:26 Getting into industrial real estate

46:22 A unique approach to law

46:40 Launching Box Equities with his sons

49:51 Getting into the mental health space

51:00 Haim’s farm

53:31 Taking a PARTIAL step back from business

54:31 Haim’s philanthropic activities

55:22 Serving as president of PROPEL

56:44 Recapping Haim’s journey

57:56 Momentum Moment

1:00:06 Closing thoughts - success is the only option

1:01:38 Outro