Episode
From Factory Worker to $300K Realtor | Milena Simsic
- Published
- Jun 11, 2026
- Duration seconds
- 4317
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Summary
Milena Simsic made $300,000 in commissions in her first year as a realtor, without any prior real estate connections, using nothing but TikTok and Instagram. She had no social media presence before she got her license. She figured it out in public. Milena is the founder of WindSocial Realty in Windsor, Ontario, and the publisher of the Windsor Real Estate Insider, a newsletter and magazine that grew to 9,000 subscribers in under a year. She also runs Windsor REI Social, a 3,000-member community that fills events with 100 to 200 investors. She is currently switching brokerages from EXP to Real and building a community for realtors who want to learn AI-powered marketing. In this conversation, we cover: Why Windsor's single-family homes have held value while student rentals and investment properties have softened What the Gordy Howe Bridge delay and the EV plant mean for Windsor's growth trajectory How Milena made $300K her first year as a realtor off TikTok and Instagram alone Why she replaced her virtual assistant with Claude AI and built her CRM systems in an afternoon How the top agents implementing AI are going to absorb market share from those who are not Why she left EXP for Real, and what Real is getting right that most online brokerages are not The health crisis that doubled her business once she fixed it Why business owners are particularly vulnerable to loneliness and what she did about it How Windsor REI Social went from monthly to biannual events and why that made it bigger Milena's arc is the arc TAFI was rebranded to celebrate: a factory worker and ICU nurse who saw where the highest-leverage play was, went all in, and built a media brand and a business that works without grinding 60 hours a week. CONNECT WITH MILENA SIMSIC Windsor Real Estate Insider: http…