His Billion-Dollar Clothing Brand Collapsed...Now He's Shaping Tech, Healthcare, & Real Estate

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://youtu.be/VY_1fK8kZ80?si=Ygkkfc0vZq7zY-LR 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