From Inner City Chicago Survival to $430M Captive Leadership: Larissa Akrawi's 27-Year Insurance Journey
Larissa Akrawi, senior vice president and captive executive at Captive Resources, shares her journey from inner-city Chicago toxic volatile environment where 12-year-old realized only way out was working (babysitting then waitressing 16, out on own 17 taking bus job to job), through answering phones at insurance agency reading everything during batch printing delivery asking inquisitive questions getting mentors' time, paying junior college on credit card because "needed that piece of paper," to running 32-year-old workers comp captive serving 151 staffing companies nationwide managing $430M assets through member-owned group model.
✨ Key Insights You'll Learn:
Inner city Chicago survivor: toxic environment age 12 realized only way out was working—babysitting then waitressing 16, moved out 17 taking bus job-to-job never thought career just survival
Receptionist reading everything: answering phones filing batch printing asked inquisitive questions, marketing manager needed assistant taught ton—licensed insurance broker taking classes stepwise progression
Junior college credit card: couldn't afford university paid two years on credit card needed "piece of paper," learned more working world than classroom pursued insurance over finishing degree
Member-owned group captives
Expense overhead 35% versus 50%: captives no offices no employees all service providers keeping costs low, other 65% goes member investment account—outperform actuary get dividend back unused claims money
Frequency versus severity model: zero-to-125K frequency everyday bumps bruises controllable through prevention
Staffing captive $430M assets: 151 companies nationwide minimum $250K premium average $900K
Data mining loss trends: identify specific client sites causing most pain—recycling facility continuous cuts buy better gloves
🌟 Larissa's Key Mentors & Influences:
Early Insurance Agency Team: Gave time explaining things when answering phones filing printing delivery—people willing teach foundational knowledge curiosity met with investment created foundation
Marketing Manager First Agency: Recommended taking insurance classes getting licensed broker taught about carriers markets submissions proposals—opened eyes possibilities stepping stones didn't realize where leading
Captive Resources Two Founding Owners: 40-employee company 1998 good culture good vibe energy drew her in—sink-or-swim training environment perfect match thrived learning figure-it-out-as-go style
Staffing Captive Members Since 1995: A-type personality grind hustle entrepreneurs built companies daily stuff coming Larissa solve problems—smart people respect needing something fills confidence bucket
Husband 30 Years Married: Iraqi father-in-law Puerto Rican father American melting pot family—supported through self-doubt promotion freak-out "what was I thinking over my head can't do this"
👉 Don't miss this conversation about 12-year-old knowing only way out was working, paying junior college on credit card because needed piece of paper, and overcoming self-doubt "kid from Chicago no MBA" by having difficult conversations smart people coming solve problems.
🔗 Connect with Larissa Akrawi:
LinkedIn: Larissa Akrawi
Company: Captive Resources
Website: captiveresources.com
Staffing Captive: tempsinsurance.com
📄 Transcript Available: Larissa Akrawi on Member-Owned Group Captives and Betting on Yourself
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📄 Special Thanks to Anthony Codispoti & AddBack Benefits Agency: AddBack Benefits Agency - Providing innovative employee benefits solutions that improve employee well-being while optimizing your bottom line Website: addbackbenefits.com