📲 Rosaki Hilt's IG: https://www.instagram.com/rosakihilt/
🌐 Level Up Workshops: https://levelupworkshops.info/
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In this episode, we sit down with Rosaki Hill, a former foster care kid turned serial entrepreneur and founder of Level Up Workshops. Rosaki grew up bouncing through the foster care system, lost his foster mom and ended up in a group home with 12 other kids in Compton and used football as his only way out of poverty. When a lost scholarship forced him into the Army, military discipline became the foundation of the leadership philosophy he still lives by today. From six figures in network marketing to losing everything at 33 after a business collapse and online attacks, this is a raw, unfiltered story about rebuilding and why imperfect action beats waiting for perfect.
💬 What We Cover:
• Growing up in foster care and the mindset it forced him to build early
• Losing his foster mom and being sent into the group home system
• Moving to Compton with 12 kids under one roof
• Football as his only path out of poverty — and losing the scholarship that changed everything
• Enlisting in the Army and how military discipline shaped his leadership style
• How Think and Grow Rich and Rich Dad Poor Dad shifted his entire trajectory
• Earning six figures through network marketing in his early twenties
• Why sales became his vehicle to financial freedom, and the story of his first sale
• Six months of failure before his first real breakthrough
• Going from zero to six figures in six months through referrals
• Why Level Up Workshops starts with goal setting and clarity
• Leaving network marketing for home improvement sales, then starting his own sales training company
• The three qualities every great salesperson needs
• Why imperfect action has defined his entire career
• Building multiple businesses while raising six kids
• Losing everything at 33 — business collapse, online attacks, and rock bottom
• Swallowing his pride, getting a job, and starting over from scratch
Follow Us:
📲 Omar's IG: https://www.instagram.com/omar_therockstar/
🌐 Level Up Workshops: https://levelupworkshops.info/
Timestamps:
0:00:00 – Intro – Rosaki's journey from foster care to serial entrepreneur
0:00:49 – Growing Up in Foster Care
0:01:43 – Losing His Foster Mom
0:02:22 – Moving to Compton with 12 Kids Under One Roof
0:03:47 – Football: His Only Path Out of Poverty
0:04:33 – Losing His Scholarship & Enlisting in the Army
0:06:40 – How Military Discipline Shaped His Leadership
0:09:07 – Think and Grow Rich & Rich Dad Poor Dad
0:09:53 – Six Figures in Network Marketing
0:13:10 – The Story of His First Sale
0:15:00 – Six Months of Failure Before the Breakthrough
0:17:41 – Zero to Six Figures in Six Months
0:20:24 – Leaving Network Marketing for Home Improvement Sales
0:23:30 – Starting His Own Sales Training Company
0:23:51 – Three Qualities Every Great Salesperson Needs
0:25:40 – Why Imperfect Action Has Defined His Career
0:27:40 – Six Kids, Multiple Businesses
0:30:18 – Losing Everything at 33
0:35:48 – Lessons From Failure & Rebuilding
0:38:54 – Swallowing His Pride & Starting Over
39:25 – Getting Rejected Before Going Door-to-Door
40:23 – Calling William Turner & Starting From Zero
41:05 – Missing a Flight, Then Getting a Second Chance
43:06 – What Door-to-Door Sales Blitzes Actually Look Like
44:35 – Omar's Own Door-to-Door Sales Story
46:19 – Off the Doors in 3 Months by Building Skills
47:10 – Turning Down a Promotion for Sweat Equity
48:40 – Becoming a Business Partner After 7 Unpaid Months
49:14 – Writing "The Broke CEO"
51:19 – Rock Bottom: Asking His Sister for Diaper Money at 33
52:47 – The Toll on His Wife & Family
54:30 – His Wife's Unwavering Support
55:00 – Recognizing a Pattern of Self-Destruction
56:16 – Taking Responsibility & Rebuilding Trust
58:28 – The Suicide Note That Changed His Mission
58:57 – A Student's Story of Abuse & Exploitation
59:18 – Building Emotional Wellbeing Tech for Kids
1:00:15 – Creating an AI Homework Assistant for Kids
1:02:21 – Why Kids Struggle: Lack of Parental Guidance
1:02:37 – Why Schools Aren't Teaching What Kids Need
1:04:18 – How AI Lets Kids Skip the Traditional Path
1:04:45 – Bringing AI, Sales & Marketing Electives to Schools
1:05:15 – Why Lived Experience Beats ChatGPT
1:05:50 – Finding the Purpose Behind His Foster Care Story
1:07:12 – From Door-to-Door & AI Tech to Level Up
1:07:46 – The Vision: An AI App in Every School
1:08:31 – Where to Find Level Up Workshops
1:09:32 – 60 Seconds of Advice to His Younger Self
1:10:22 – Redefining Success Beyond Money
1:11:55 – Word Association Game
1:13:30 – What Legacy He Wants to Leave
1:14:56 – Final Words of Wisdom
1:16:38 – Closing Remarks & Outro