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From Factory Worker to $300K Realtor | Milena Simsic
Description
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: https://www.windsorrealestateinsider.comInstagram / LinkedIn / Facebook / YouTube: search 'Milena Simsic'
Chapters
00:00: Introduction and Cold Open
01:20: Milena's background: factory worker, nursing, COVID, Windsor
03:00: Breaking news: brokerage switch from EXP to Real
04:00: Windsor Real Estate Insider magazine, 9,000 subscribers
05:30: Windsor market conditions: what is holding and what is not
07:00: The Gordy Howe Bridge delay
08:30: EV plant, population growth, downtown development
09:30: What investors are doing in Windsor right now
13:00: $300K first year off TikTok and Instagram
17:00: Building Windsor REI Social to 3,000 members
22:00: AI adoption gap: top agents vs. everyone else
28:00: Replacing a virtual assistant with Claude
31:00: How many hours per week to run the business
33:30: Teaching other realtors AI-powered marketing
38:00: The Windsor pageant: why she entered, first runner up
41:00: The autoimmune condition, the health pivot, business doubling
45:00: Salsa dancing as the one thing that started everything
48:00: Business owner loneliness and why dance helps
51:00: EXP vs. Real: why the switch and what Real is doing differently
58:00: AI tools, Fiverr comparison, what Claude does that nobody else can match
01:01:00: Advice for young people: build your skill set, buy a business, zero excuses
01:03:00: Wrap up and where to find Milena