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