Sales Psychology That Built a $35M Brand

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From Boston streets to building a $35M+ brand, Isakar Jean Simon shares the real story behind his journey as Head of Onboarding and top closer for a multi-million-dollar funding and credit business.
In this conversation, we cover everything from growing up in a strict Haitian household, learning adaptability in sales, the power of MLMs as a foundation, and mastering the psychology of closing.
If you’ve ever wondered how high-performing closers shape-shift their style, run onboarding at scale, and help build 8-figure businesses—this is your blueprint.

You’ll learn:

How to adapt your sales style to any personality type

Why culture, mindset, and self-awareness matter in business

The financial pitfalls that kill early success—and how to avoid them

How to transition from the streets to legitimate, scalable income

Where to find, hire, and train high-performing closers

00:00 – From $70K gone to finding the right closing style
01:10 – Guest intro: Haitian roots & Boston upbringing
02:43 – Growing up strict in a Haitian household
04:16 – Inner city vs suburbs: shifting perspectives
05:47 – Early ambitions & sports dreams
07:48 – First jobs and entrepreneurial sparks
09:38 – No pressure from parents, just figuring life out
11:10 – College journey, football, and financial reality
14:14 – Early hustles & MLM lessons
17:07 – How MLMs build a sales foundation
18:22 – Clothing lines, hustles, and setbacks
21:10 – Lessons from street smarts applied to business
24:18 – Building a network with Darius
27:29 – First mentorship investment
29:29 – The mindset shift into sales
32:16 – Sneaker flipping and creative marketing
36:22 – Darius discovers credit funding
38:08 – The digital product boom & skepticism
42:13 – Becoming a tax broker & learning money flow
44:24 – Losing $70K through mismanagement
46:46 – Communication, relationships & money stress
48:54 – Identity, shadow work & staying “him”
50:53 – Relationships: partner or solo in business?
55:39 – Becoming Head of Onboarding
56:57 – Where to find and hire closers
59:12 – Commission structures & pay models
1:02:08 – Learning from controversial figures
1:05:02 – The “Shape-Shifter” closing style
1:11:06 – Running onboarding & program qualifications
1:18:47 – Inner Circle qualifications & events
1:23:51 – Dream future: acquisitions & scaling
1:25:22 – Business brotherhood with Darius
1:27:06 – Teaching sales to kids in real time
1:31:11 – Attractive Mindset’s mission & free classes
1:33:42 – Authenticity, image & breaking stereotypes

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